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l’actualité chimique canadienne canadian chemical news FEBRUARY FÉVRIER • 2005 • Vol. 57, No./no 2




FEBRUARY FÉVRIER • 2005 • Vol. 57, No./no 2

A publication of the CIC/Une publication de l’ICC

Ta ble of Contents/Ta ble des matièr es

Guest Column/ Chroniqueur invité . . . . . . . . . 2 Dream Jobs on the Web Mark Gregory Personals/Personnalités . . . . . . 3

Feature Ar ticles/Ar ticles de fond Roadmap on Bio-Based Feedstocks 13 Innovation for Fuels and Industrial Products Capturing Canada’s natural advantage

News Briefs/ Nouvelles en bref . . . . . . . . . . 4 Chemputing . . . . . . . . . . . . 9 Acrobatic Archiving Marvin D. Silbert, FCIC Chemfusion . . . . . . . . . . . .10 The Gene Scene Joe Schwarcz, MCIC Chemical Shifts . . . . . . . . . . .11 Cathleen Crudden, MCIC, and Hans-Peter Loock, MCIC

J. E. Cunningham


CSCT Bulletin SCTC . . . . . . . 28


Careers/Carrières . . . . . . . . . 34

A Changed Link

The Ontario Chemistry Value Chain Initiative forms non-traditional alliances to re-invent the Ontario chemical industry Bernard West, FCIC, and Joanne West

20 French Fries Fuel the Future

Visualize french fries as a solution to the energy crisis … a hands-on look at the development and implementation of biodiesel fuel

Local Section News/ Nouvelles des sections locales . . . 29 Student News/ Nouvelles des étudiants . . . . . . 29

Turning sugar polyols into a new and renewable resource base for the petrochemical industry Marcel Schlaf, MCIC

CIC Bulletin ICC . . . . . . . . . 24 CSChE Bulletin SCGCh . . . . . . 24

The Deoxygenation Challenge

Katie Eliot



Events/Événements. . . . . . . . 37

Cover/Couver ture

Professional Directory/ Répertoire professionnel . . . . . . . .37

Bioproducts. How is the chemical community maximizing Canada’s natural resources toward a global advantage?


Dream Jobs on the Web

Mark Gregory

Editor-in-Chief/Rédactrice en chef Michelle Piquette Managing Editor/Directrice de la rédaction Heather Dana Munroe


confess. I am a middle-aged baby boomer who envies the many Canadian engineers, chemists, and technologists who are just coming into the field and are interested in the bioproducts area. Finding that dream job is a lot easier than it was just a few years ago. Gone are the days of that trek to the library to hunt through the “Help Wanted” and “Careers” sections of newspapers in local and sometimes exotic locales. Today, technology has produced two superb tools for job seekers to find the best jobs, fast and effectively. A beautiful marriage has occurred between the Internet, which puts the world’s information resources at our fingertips, and software that creates on-line, Web-based career sites. This evolution now enables companies, institutions, and those looking for work or to advance in their careers to find each other with a few strokes of the keyboard. The CIC has a decent career site. Consider it a starting point. Powerful search engines like Google will help you find more. At last count, there is something like 10,000 or more such sites on the Internet. But, more or big are not necessarily best. The really great on-line career sites are called niche sites. Unlike the huge sites owned by newspaper chains, ad agencies, or multinational HR conglomerates, these career sites have a specific industry focus. I am most familiar with It is aimed at the Canadian life sciences sector including the biotechnology, pharmaceutical, medical device, and healthcare fields. Here are ten tips to finding the right career site and how to make it work for you: 1. Check out the types of jobs on the site. Do they reflect an appealing range in your field and your future? Look for a good cross-section of technical, scientific, and professional jobs at a variety of levels. 2. Find out if the site has real people you can call toll free when you have a question about your résumé or a job they post. Don’t bother with the ones you have to e-mail, and wait and hope for a response. 3. Check out company career sites. Many of today’s “Employers of Choice” like


Merck Frosst, Sanofi Pasteur, and Pfizer Canada in the pharmaceutical field have sites that enable you to review their postings and apply on-line. 4. Look at the site’s partners and links. If the site is an active member of local and national industry associations, there’s a good chance they have the kind of credibility and industry knowledge that attracts good candidates and employers. 5. Make sure the site offers you anonymity. Under Canada’s privacy law, job seekers have a right to keep their personal information confidential. 6. Look for a site that has a regular and useful on-line or e-mail newsletter about industry trends and jobs. It’s an easy way to stay abreast of a world of opportunity. 7. Keep track of the sites where you register, as well as the information or passwords you need to access your personal profiles. Then, make it a habit to check these sites often, and keep your profile up-to-date. 8. If you are a student, use the time before graduation to find the best sites. Polish your résumé and on graduation, when you are ready and available for work, register on the sites with jobs that seem to match your credentials. 9. Select a career site that offers you a personal “job agent” that will diligently alert you to new opportunities. 10. Develop a relationship with a site with a range of industry training in such key areas as regulatory affairs, GMP, supervisory and management skills, and soft skills from communications to dealing with difficult people. No university chemistry degree qualifies or trains one adequately for any of these topics. The next time you turn on your computer remember, your dream job in bioproducts may await, just a few mouse clicks away. Happy hunting!

Mark Gregory is VP of Pharmahorizons and associate editor of BioBusiness magazine.

Graphic Designer/Infographiste Krista Leroux Editorial Board/Conseil de la rédaction Terrance Rummery, FCIC, chair/président Catherine A. Cardy, MCIC Cathleen Crudden, MCIC John Margeson, MCIC Milena Sejnoha, MCIC Bernard West, MCIC Editorial Office/Bureau de la rédaction 130, rue Slater Street, Suite/bureau 550 Ottawa, ON K1P 6E2 613-232-6252 • Fax/Téléc. 613-232-5862 • Advertising/Publicité Subscription Rates/Tarifs d’abonnement Non CIC members/Non-membres de l’ICC : in/au Canada CAN$55; outside/à l’extérieur du Canada US$50. Single copy/Un exemplaire CAN$8 or US$7. L’Actualité chimique canadienne/Canadian Chemical News (ACCN) is published 10 times a year by The Chemical Institute of Canada / est publié 10 fois par année par l’Institut de chimie du Canada. Recommended by The Chemical Institute of Canada, the Canadian Society for Chemistry, the Canadian Society for Chemical Engineering, and the Canadian Society for Chemical Technology. Views expressed do not necessarily represent the official position of the Institute, or of the societies that recommend the magazine. Recommandé par l’Institut de chimie du Canada, la Société canadienne de chimie, la Société canadienne de génie chimique et la Société canadienne de technologie chimique. Les opinions exprimées ne reflètent pas nécessairement la position officielle de l’Institut ou des sociétés constituantes qui soutiennent la revue. Change of Address/Changement d’adresse Printed in Canada by Gilmore Printing Services Inc. and postage paid in Ottawa, ON./ Imprimé au Canada par Gilmore Printing Services Inc. et port payé à Ottawa, ON. Publications Mail Agreement Number/ No de convention de la Poste-publications : 40021620. (USPS# 0007-718) Indexed in the Canadian Business Index and available on-line in the Canadian Business and Current Affairs database. / Répertorié dans la Canadian Business Index et à votre disposition sur ligne dans la banque de données Canadian Business and Current Affairs. ISSN 0823-5228


University Fa t h i H a b a s h i , M C I C , i s professor emeritus at the department of mining, metallurgical, and materials engineering at Université Laval in Québec, QC. He has created a research unit called “Mining and Metallurgical Heritage.” The unit is planning to host the Cultural Heritage in Geology, Mining, and Metallurgy in 2007. The unit will collect , classify, safeguard, and make known documents pertaining Fathi Habashi, MCIC to th e Can adian hi s t or y of mining and metallurgy—including old books, magazines, journal articles, personal correspondence, photographs, etc., that may help trace the history of a process, a person, or an establishment related to mining and metallurgy, nationally or internationally. The unit will rely on donations of material that should be saved from loss or destruction, that could be useful for future generations. A permanent exhibit on the history of mining and metallurgy in Canada is also planned. Workshops for students and secondary school teachers will be held to discuss the history of the Canadian mineral industry and its importance to society. The unit is also planning to create a biographical dictionary for mining and metallurgy to record the contributions of Canadians involved in this industry. It will be updated in the future by publishing supplements. In addition to moral support, Habashi’s research unit is soliciting financial support from individuals, industry, the government. Contact for further information on the project and donations.

Chao-Jun Li, MCIC

David Boocock, FCIC, former chair of the department of applied chemistry and chemical engineering at the University of Toronto was recently honoured by the Canadian Renewable Fuels Association at an event showcasing renewable fuels. More on page 8. Robie MacDonald, FCIC, has been inducted into the Royal Society of Canada. He describes David Boocock, FCIC himself as an aquatic pathways specialist and notes that his studies have reference to both contaminants and climate change.

In Memoriam

The CIC extends its condolences to the family of Albert Stoessl, FCIC.

Erratum CSC president 2005–2006, Yves Deslandes, FCIC, was mistakenly featured with the CIC Board of Directors in ACCN Vol. 56, No. 10. He belongs with the CSC Board of Directors on p. 24 of that issue.

Chao-Jun Li, MCIC, Canada Research Chair (Tier I) in green chemistry at McGill University, has been appointed associate editor of Green Chemistry, a journal published by the Royal Society of Chemistry in the U.K. He will be responsible for handling manuscripts from North America.

Distinction Robert Ackman, FCIC, has received the Lifetime Achievement Award from the Canadian Section of the American Oil Chemists’ Society for his distinguished contribution to the field of lipids. He has an international reputation for his seminal work on lipid analytical chemistry, particularly in the capillary gas liquid chromatography of fatty acids and the chemistry and biochemistry of marinelipids.


More Bounce for Your Buck Sunflowers and lettuce are proving to be more than just pleasing to the eye and the palate. They’re both being cited as promising alternative sources of rubber. More than 40,000 industrial products and 400 medical devices are currently made from rubber. But production problems such as a lack of genetic diversity, uncertainty of supply, and latex allergies have prompted researchers to investigate new ways to produce rubber. John Vederas, FCIC, is a chemistry professor at the University of Alberta and a Canada Research Chair in bio-organic and medicinal chemistry. He has been working extensively with U.S. collaborators to develop industrial-quality rubber from Canadian-grown crops. “This technology could utilize Canada’s vast agricultural industry in a whole new way by doubling the role of native plants,” he says.


The key is to produce an alternative source with “long” rubber molecules. These produce a higher-quality, stronger rubber because there is more attraction, and therefore more strength, between longer rubber molecules than between shorter ones. Sunflowers were the springboard to this project. They’re among the 2,500 plants worldwide that are known to naturally produce small quantities of rubber, but can’t generate sufficiently high-quality rubber to satisfy the annual U.S. $28-billion demand for rubber-derived finished goods. So Vederas plans to identify the genes responsible for making rubber in the Canadian sunflower and replace them with rubber-producing genes from the rubber tree. He hopes the rubber produced in the sunflower, unlike that from the rubber tree, will not inflame latex allergies. Another point of focus is lettuce. It produces extremely high-quality rubber because its rubber molecule is long and resembles that of the rubber tree. But, further study is needed to determine its quality and protein make-up.

Rubber prices are currently controlled by cartels, and the rubber tree grows only in tropical climates. Both sunflowers and lettuce would make excellent substitutes for rubber because they grow naturally in Canada, which means they can withstand colder climates and can be cultivated on a mass scale. The potential impact this could have on the Canadian agricultural industry is huge, Vederas says. Excerpted from Kate Roberts’ article printed in Advance magazine.

Last year, the Advanced Foods and Materials Network (AFMNet), employed students from the University of Guelph’s Students Promoting Awareness of Research to coordinate and write a national research magazine. That magazine highlights AFMNet research activity across the country. The finished product, Advance, features news articles about some of the network’s 87 researchers from 24 universities across Canada who specialize in physics, food science, nutrition, biochemistry, engineering, health, law, and society.

Photo by Sorin Brinzei


Smart Materials = Fresher Food

Science Confirms Chamomile’s Curative Qualiteas A recent study conducted in England confirmed that drinking chamomile tea might help relieve a range of ailments including colds and menstrual cramps. The plant used in the study was German chamomile (Matricaria ecutila), known also as manzannilla. The flowers and leaves were brewed to make a fragrant tea. Fourteen volunteers drank five cups of the tea daily for two consecutive weeks. Urine samples were tested daily before and after drinking chamomile tea. The study found that drinking the tea was associated with a significant increase of hippurate in urine. Hippurate is a breakdown product of certain plant compounds called phenolics, some of which possess antibacterial activity. This may explain why chamomile tea as an herbal medicine helps relieve colds. It was also found in the study that drinking the tea was linked to an increase of urinary glycine, an amino acid and muscle relaxant. Glycine has been shown to relieve muscle spasms. This may explain why chamomile tea relieves menstrual cramps in women. The study appeared in the January 26, 2005 issue of Journal of Agricultural and Food Chemistry. Food Ingredients First

Photo by Olivia Castells

“Intelligent” product packaging that controls its own passage of air and water is just one example of new small-scale materials being developed by an Advanced Food and Materials Networks’ research group. Robert Prud’homme, FCIC, professor in the department of chemistry at the Université de Montréal, is leading a collaborative project to produce what are called “smart” materials. These include packaging that can keep food fresh, depending on the surrounding conditions such as temperature, humidity, and light. To create these materials, Prud’homme and his colleagues have to start small—at the microscopic scale. They’ll consider the molecular properties of nanostructures on the surfaces of polymers, which are impossible to see and difficult to manipulate. But Prud’homme believes these nanostructures can be chemically fine-tuned, so they can keep food fresh under different conditions on the larger scale. “We’re trying to control the small-scale nature of these surfaces precisely,” he says. “In principle, it’s possible to create materials that would react differently depending on the environment.” Here’s how these nanostructures work. Researchers choose two different types of polymers, carbon-based molecular chains made up of many identical links carefully chosen for their chemical properties. Then, the individual polymers are stitched end on end to form new, longer chains that contain both polymers in specific sequences. These new chains, called “block copolymers,” assemble themselves under appropriate conditions to create a film or coating. Prud’homme’s group can perform chemical reactions to selectively modify certain groups of polymers, fine-tuning the surface’s interaction with molecules such as oxygen and water, so it’s dependent on external conditions. This principle allows smart packaging to keep food dry in moist conditions, for example, or let water escape when it’s hot—simply by changing the surface of the material, without the packaging opening or closing. More intelligent packaging materials made from such processes may lead to fresher food down the line.

This project is in its infancy, but Prud’homme says biodegradable polymers may eventually be used in this process, making packaging both intelligent and environmentally friendly. He also foresees using new materials to fine-tune interactions between cells and polymers, which would open the door to new nanostructure coatings that would allow better drug delivery. Such coatings would encapsulate drugs, preventing blood proteins from binding to them and inactivating them, allowing the drugs to reach a target site and be released at an appropriate rate. “This project is just beginning,” says Prud’homme, “but if we succeed in controlling the surfaces, this work could continue for many years to come, with many different applications.” Other researchers involved in this project include Geraldine Bazuin, FCIC, and Alexis Laforgue, Université de Montréal, and John Dutcher, ACIC, University of Guelph. This work is sponsored by AFMNet, the Natural Sciences and Engineering Research Council, and le Fonds québécois de la recherche sur la nature et les technologies. By Robert Fieldhouse. Reprinted with permission from Advance magazine.

Computer visualization of a block copolymer used to deliver a drug to the human body. Two molecular chains are joined together end to end. Red represents hydrophilic regions. Green represents the hydrophilic copolymer surfaces. Blue represents water and bright areas represent the drug.


Undying Colour Researchers in the Mechanical Wood-Pulps Network have unravelled the complex chemistry responsible for one of the paper industry’s most serious problems—paper that turns yellow only a few weeks after it is made. The new understanding achieved by the Network should provide the basis for improving a low grade of paper, and for helping Canadian manufacturers to increase their competitiveness by making mechanical pulps more suitable for an expanded range of higher-value grades of paper. Both industry and academic researchers specializing in wood chemistry have been wrestling with the problem of yellowing for more than 40 years. Network researcher Jeffrey Wan, FCIC, of Queen’s University, was able to bring a new approach to the problem through his work on the behaviour of free radicals, groups of atoms that are generally highly reactive. In pulp and paper processing, these free radicals often persist in the finished product, where they interact with light and turn the white page yellow.


The technical name for this chemical reaction is reversion, because it reverses the effect of the bleaching that is meant to make the wood pulp as white as possible. While previous research has focused on ways of treating paper to counteract reversion, Wan and his team of researchers at Queen’s found that a more comprehensive bleaching technique could make reversion all but impossible. It was while searching for evidence of the cause of yellowing, that Wan discovered how bleaching itself generates both “good” radicals, which preserve the paper’s integrity, and “bad” radicals, which lead to yellowing. He saw that a post-bleach treatment would have to maximize the good radicals, and eliminate the bad. The team developed a treatment system that protects paper against the yellowing radicals, while preserving those radicals that can repair any yellowing damage that does occur. The system, now being patented, has been dubbed the protect-repair mechanism. This is an important step towards broadening the market for mechanical pulps, at present the basis for Canada’s economically vital newsprint industry.

An additional advantage is that the process is environmentally friendly. Unlike chemical pulping processes that require chemicals to break wood down into its constituent fibres, mechanical pulping is largely a matter of grinding up the wood into basic components. It is cheaper and less polluting, but the problem of yellowing has limited its potential market. “The Network has given us vital access to people who are at the forefront of important techniques, not only in instrumentation, but also in the specialized chemistry,” notes one of the Network’s industrial researchers, John Schmidt, MCIC, of the Pulp and Paper Research Institute of Canada (Paprican). Schmidt’s work was instrumental in the bleaching technology. Pulp and paper production is Canada’s major manufacturing industry. The pulp and paper industry accounts for approximately $12 billion worth of the country’s net exports. This is approximately equivalent to that of mining, petroleum, electricity, and fisheries combined. It alone accounts for nearly all of Canada’s net trade balance. Government of Canada

Art by Heather Dana Munroe


Paper Research Partnership NSERC announced funding of $1.5 million for two new Industrial Research Chairs in the department of chemistry at McGill University. The industry partner in the initiative is the Pulp and Paper Research Institute of Canada (Paprican). The research aims to improve the papermaking process, thereby enhancing the competitiveness of the industry and further reducing its environmental impact. “Pulp and paper is a vital sector of the Canadian economy. It contributes more than any other industry to Canada’s trade surplus. But to stay competitive, this industry must constantly innovate, and design processes and products that are marketable and environmentally sustainable. These Industrial Research Chairs will provide the foundation of new knowledge that can open doors for us,” said David L. Emerson, minister of Industry. “The partnership between McGill University and Paprican is an excellent example of how Canadian universities and industry are collaborating for the benefit of the economy and society,” added Lucienne Robillard, president of the Privy Council and minister of Intergovernmental Affairs. The federal funding is being provided over five years through NSERC’s Industrial Research Chairs program. Paprican will also contribute $1.5 million in direct funding, along with significant in-kind resources for both the research and the dissemination of results. The chairs will support the training of some 20 master’s and doctoral students. One of the two new chairs, Theo van de Ven, MCIC, will look at the chemistry of paper while the paper is being formed and still wet. “The ‘wet’ end of the process is of growing importance in papermaking due to increased emphasis on recycling and reduction in water usage,” he said. “It’s a field that has direct industrial applications and provides challenging research topics for students.” The other new chair, Derek G. Gray, will examine novel properties and uses of wood pulp fibres. “The goal of our research will be to better understand how the cellulose fibres bond together in paper sheets. We will also work on new value-added products based on the unique properties of the fibres,” he said.

Canadian Chemicals Productivity Top Ranked The Conference Board of Canada has released its “Performances and Potential” report. The report includes the latest productivity data showing that the level for Canadian chemical manufacturing continues to exceed its U.S. competitors. Moreover, the recent productivity growth rate for basic chemicals is over five percent per year—almost four times its U.S. counterparts. Copies of the report can be accessed through the Conference Board of Canada Web site at

depletion. However, biofuels are in general more expensive to produce. Given competing land use and biomass usage, biofuels from agricultural biomass can probably only substitute a small portion of fossil fuels. Production of innovative biofuels will require new technologies. For more information on the study, visit Camford Chemical Report

Chemical Sales Rise to $24 Billion in 2004

Canadian Chemical Producers’ Association

Biofuel Pros and Cons A major review of literature on biofuels has been released by the Research Association for Combustion Engines (FVV) under the title CO 2 Mitigation Through Biofuels in the Transport Sector—Status and Perspectives. The FVV commissioned the Institute for Energy and Environmental Research Heidelberg (IFEU) to analyze and compare all publicly accessible publications on biofuels worldwide, starting with biodiesel and bioethanol and extending to synthetic fuels made of biomass. The IFEU checked several hundred publications. In the end, the institute evaluated 63 studies on about 30 different biofuels and over 100 energy and climatic gas balances. As expected, the results of the energy and greenhouse gas balances—and the cost estimates of biofuels—vary widely in the individual studies. However, the variances mainly result from different assumptions regarding cultivation and conversion of valuation of coproducts. The study concluded that biofuels for transportation offer ecological advantages over fossil fuels in resource conservation and climate protection. These advantages outweigh disadvantages in contributing to acidification, eutrophiciation, and ozone

Overall sales of Canadian basic chemicals and resins increased by 14 percent in 2004, when compared to 2003. Operating profits almost tripled in 2004 to $2.1 billion. The 2004 estimates are based on Statistics Canada data for the first nine months of 2004. Growth is strong, but profitability continues to be threatened. “This is a case of good news/bad news,” said Steve Griffiths, chair of the Canadian Chemical Producers’ Association (CCPA). “It is tremendous to see 14 percent growth, but new factors like high energy prices and a strong Canadian dollar could erode these gains very quickly.” “Chemical producers, who make plastics, textiles, and thousands of products possible, rely heavily on energy and natural gas as a feedstock. We’re urging Canada’s governments to make energy a national priority,” said CCPA president and CEO, Richard Paton. Looking ahead, survey respondents expect sales value to grow by six percent and volumes to grow by another two percent in 2005. Exports are predicted to grow by seven percent, led by an increase of 21 percent in exports to the U.S. Operating profit is expected to grow by a further eight percent to $2.3 billion in 2005. Fixed capital investment is forecast to increase by 32 percent from 2004’s low level to $1.2 billion in 2005. For a copy of the complete year-end survey, please see “Year End Survey of Business Conditions” at Canadian Chemical Producers’ Association




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Preliminary findings suggest that PSP94 Serum-based immunoassay may be of clinical utility for the detection and prognosis of prostate cancer. Montréal-based company, Procyon Biopharma Inc. has reached an important milestone in identifying the Prostate Secretory Protein of 94 amino acids (PSP94) binding protein. This is a crucial part of Procyon’s assay development technology for prostate cancer diagnosis and prognosis. Many scientists have shown that there is a clinical need within prostate cancer management to identify new diagnostic and prognostic markers that are more accurate than the existing tests. In a previous peerreviewed publication, Procyon’s collaborating scientists demonstrated that pre-treatment blood measurements of bound and free PSP94 can accurately separate prostate cancer patients treated with curative intent radiotherapy into “good” and “bad” prognostic groups. Recent findings at Procyon have been accepted for publication in the Biochemical Journal and are currently available online. In the article entitled, “Identification, Purification and Characterization of a Novel Human Blood Protein with Binding Affinity for Prostate Secretory Protein of 94 Amino Acids,” Procyon scientists show that PSP94 binds to a novel protein, known as PSPBP, in the serum. The identification of the PSP binding protein has enabled Procyon scientists to develop new simple blood tests that specifically measure the free form of PSP94 (unbound to binding proteins) and the total form of PSP94 (bound and unbound to binding proteins) as well as the total PSP94 binding protein. The determination of the ratio of free PSP94 and PSP94 bound to PSPBP is believed to be correlated with the prognosis of prostate cancer. Procyon Biopharma Inc

The president and CEO of Sustainable Development Technology Canada, Vicky J. Sharpe, joined University of Toronto (U of T) researchers at an event to showcase renewable fuel research and to unveil plans for Canada’s first demonstration biodiesel plant. A six- by six-foot paper plan of BIOX Corporation’s demonstration biodiesel plant was unveiled. The plant will be based in Hamilton, ON, and will use technology developed by U of T professor, David Boocock, FCIC. The event also highlighted other research into ethanol fuel, 21st-century vehicles, and pollution control. Boocock was also celebrated with an award presented by the Canadian Renewable Fuels Association. The new BIOX plant, slated to be in production in the summer of 2005, will be capable of producing 60-million litres of biodiesel fuel per annum. Biodiesel fuel—a renewable sulphur fuel made from a variety of feedstocks—can be used in any unmodified diesel engine and will greatly reduce harmful emissions compared to traditional fuel. Sustainable Development Technology Canada has approved in principle a $5 million contribution to the development and demonstration of the technology. Along with Sharpe, participants in the renewable fuels event included Peter Munsche, U of T’s assistant vice-president (technology transfer); Tas Venetsanopoulos, dean of U of T’s faculty of applied science and engineering; Tim Haig, president of BIOX Corporation; David Boocock, former chair of U of T’s department of applied chemistry and chemical engineering; and Kory Teneycke, executive director of Canadian Renewable Fuels Association. University of Toronto


Acrobatic Archiving


ssentially, all of today’s reports and scientific papers are prepared using a computer. It’s easy to forget that widespread access to computers is a new phenomenon. The bulk of the world’s documentation is on paper. While everybody talks about computerizing their old files, it can be a formidable task. I would like to pass on some of what I learned from my crude attempts. Even an inexpensive scanner can make good electronic copies. The challenge is to determine how to set up the scanner and then select the ideal file format to save that copy. The usual BMP or TIF file can be huge, especially if the scanner is not properly set up. Most documents are black and white with nothing in between. I set my Epson scanner to “Text/Line Art” and manually tweak the threshold level to make it look right. The same thing may be done with other scanners on a fax setting. Don’t choose a greyscale or colour setting unless the document includes photos or the file could be an order of magnitude larger. Another way to keep the file size down is to keep to the lowest legible resolution. I tend to go for 200 dpi. My archiving system revolves around Adobe Acrobat Pro version 6.0. That’s the expensive full-blown version with all the bells and whistles that are not included with the freebie Reader. This is one of the most useful pieces of software available today for handling paper. Select “Create PDF” and choose “From Scanner.” It will control everything including starting the scanner and saving the file. I found the PDFs to be about half the size of JPGs and as little as one tenth the size of TIFs. As it finishes scanning each page, it asks if I am done or if I want to append another page to the file. This keeps things rolling with multiplepage documents until it hits the default

with most scanners, which is to do a lowresolution preview before each scan. That’s a waste of time if all the pages are the same size and shape. Once I found how to untick the “Automatic Preview,” The scanner would remember the settings from the last page and keep using them until instructed otherwise. To OCR, or not to OCR: that is the question. The scanned image is a picture of the page. To get a small file size that can be computer searched, these graphics images should be converted into text files. Most scanners come with Optical Character Recognition (OCR) programs that attempt to read the files and convert them into text. The success rate varies from document to document. In many cases, you can end up spending a lot of time correcting the errors and formatting the text file into a meaningful document. Acrobat takes a different approach to making the scanned document searchable. Select “Document” and “Paper Capture.” When you “Start Capture,” you do an OCR on the document, but will never get to see it. At first, I couldn’t figure out what I did—or if I really did anything at all—as there was no change in the appearance of the document. I pressed <Ctrl>F and suddenly found that Acrobat could now search this picture of the page as if it were a text page and highlight the search words as it found them. There was no need to go to any effort correcting the OCR results and formatting the page. For my initial test, I chose two vastly different documents. The first was a fourpage article with several graphs and both B&W and colour photos. I scanned it as a colour document after adjusting the background to make the page a pure white. The file was 403 kB. After running Paper

Marvin D. Silbert, FCIC Capture, the size increased to 484 kB. The other document was a one-page fax received by my computer and printed as a PDF. The file was 34 kB before running Paper Capture and 46 kB afterwards. When I searched for a few key words, it seemed to catch them all in the paper, but missed a few in the fax. That’s what you would expect as the paper was scanned at 300 dpi and the fax appears to have been sent using the “Standard” mode. The ability of OCR software to read the text is highly dependent upon the quality of the text it encounters. Unfortunately, too few people seem to be aware that fax machines have a fine setting that transmits a clearer image. When you start archiving material, it is inevitable that you will end up with a plethora of files. Adobe offers another useful feature for consolidating them. By selecting “Create PDF” and “From Multiple Files,” I was able to integrate more than a hundred separate PDFs into a much-more-manageable single file that took up less memory than the original group. You are given the option to arrange them in any order. Bookmarks can also be added to aid in locating them. I have a home office that is crammed with paper. My objective for 2005 is to eliminate a metre of it. Doing so is going to be much simpler than I thought. What about the material that has never seen the light of day for decades? To scan or not to scan? To shred, or not to shred? Those are the questions.

You can reach our Chemputing editor, Marvin D. Silbert, FCIC, at Marvin Silbert and Associates, 23 Glenelia Avenue, Toronto, ON M2M 2K6; tel. 416-225-0226; fax: 416-225-2227; e-mail:; Web site:



The Gene Scene Generating interest in biotech


ow! Look at my DNA!” the exuberant little boy blurted out as he pulled the threadlike strands out of the test tube. Soon other excited voices chimed in as about two dozen children and a sprinkling of adults began to play with their own genetic material. We were all seated around tables in a laboratory at the American Museum of Natural History in New York, NY, having been attracted by signs pointing towards the “Gene Scene.” Our experiment started with everyone swirling salt water in their mouth for thirty seconds or so to collect some of the cells that are continuously sloughed off by our cheeks. We were then asked to spit the solution into a little cup (as cries of “yuck” filled the room) and then transfer it to a test tube containing some detergent. A couple of minutes of gentle shaking allowed the detergent to break down the cell membranes and liberate the DNA molecules that were then solidified by the addition of alcohol. We then dipped a stirring rod into the test tube and pulled out long filaments of DNA. As the session drew to a close, the children were asked what they had learned. There were some pretty good answers, but the one that really stuck in my mind was provided by the little boy who had cried out so enthusiastically when he first glimpsed his DNA. What he had learned, he said, was that when he grew up he wanted to study biotechnology and become a genetic engineer! Quite a refreshing comment given that so many people these days look warily on this area of science. The raised eyebrows can often be traced to a lack of clear understanding of what biotechnology is all about. Simply put, biotechnology is the provision of useful products and services from biological processes. It does not necessarily involve scientists in white lab coats hovering over


Petri dishes. In fact, biotechnology goes back thousands of years, probably to the first use of yeast to convert sugars and starches to alcohol. Yeast is a little living machine that takes in food and produces excrement. But don’t poopoo that excrement. Many humans like it. It’s called alcohol. Moulds are also neat little machines that produce a variety of by-products. When the ancient Egyptians put mouldy bread as a poultice on wounds, they were using biotechnology. The mould probably churned out penicillin, not recognized as such of course, and helped the wound heal. How these microbes convert raw materials into finished products was not elucidated until relatively recent times. The pivotal moment came in 1953 when Francis Crick and James Watson unravelled the molecular structure of DNA, the molecule that controls the inner workings of the living cell. The instructions for everything a cell does are encoded in genes that are specific fragments of DNA. Basically, genes tell the cell what proteins to produce. Proteins are needed as structural material and as enzymes, the catalysts that control all reactions in a cell. Once DNA’s role was clearly understood, it became obvious that if its structure could be modified, the proteins it produced could be altered. By the 1970s, such manipulation—known as genetic engineering—had become a possibility. Genes could be transferred from one organism to another, or could even be built from fundamental components using the modern version of the “Gene Machine,” invented by former McGill University chemistry professor, Kelvin Ogilvie, FCIC. These days, insulin for diabetics is cranked out by bacteria to which the human insulin gene has been transferred. Bacteria also have been engineered to produce tissue plasminogen activator (TPA), which has saved countless lives. It is commonly administered after a heart attack to dissolve blood clots. Unfortunately, bacterial fermentation cannot meet

Joe Schwarcz, MCIC the need for TPA and the drug ends up costing thousands of dollars per gram. Researchers have recently succeeded in introducing the gene that codes for TPA into the DNA of a goat with the result that the animal produces TPA that can be isolated from its milk. In this process, known as “pharming,” one goat can make as much TPA as a 1,000 litre bioreactor. Biotechnology may even prevent heart attacks from occurring in the first place. The little Italian hamlet of Limone Sur Grada has become famous because its inhabitants are free of heart disease in spite of having high blood cholesterol levels. They have inherited a gene that codes for Apolipoprotein A1, a special protein that scavenges cholesterol from the bloodstream. Injections of a genetically engineered form of this protein have dramatically reduced the clogging of rabbits’ coronary arteries, a treatment that may eventually be viable for humans as well. Perhaps our young biotechnologist-to-be may one day work on this problem. But for now, he was content to scrutinize a display about lysozyme, a natural milk enzyme with antimicrobial properties. Genetic engineering techniques can increase the levels of this enzyme in milk, reducing udder infections and the need for antibiotics. As the little guy wondered off, I noted that he stuffed his DNA sample into the back pocket of his jeans. Jeans that may have been dyed with indigo produced by recombinant DNA and made of cotton genetically engineered to repel insects without the need for pesticides.

Popular science writer, Joe Schwarcz, MCIC, is the director of McGill University’s Office for Science and Society. He hosts the Dr. Joe Show every Sunday from 3:00 to 4:00 p.m. on Montréal’s radio station CJAD and on CFRB in Toronto. The broadcast is available on the Web at

Chemical Shifts

What’s new in chemistry research? Chemical Shifts offers a concentrated look at Canada’s latest developments. Cathleen Crudden, MCIC, and Hans-Peter Loock, MCIC

Solid sensors for VOC’s based on polymorphic polymers Many solids exist in more than one crystallographic form, or polymorph, which can have significantly different physical properties. Pharmaceutical companies spend a considerable amount of time studying the polymorphic forms of drugs since differences in properties such as solubility can lead to large variations in bio-availability. Controlling polymorph formation can be a complicated black art, especially if the desired polymorph is the less stable one. This reporter has been told of instances where completely new buildings had to be constructed in order to prepare the less stable polymorph of a drug when all existing plants were producing the more stable, and less bio-available, polymorph! In a recent full paper in the Journal of the American Chemical Society (2004, 126, 16117), chemistry professor Daniel Leznoff, MCIC, along with graduate student Julie Lefebvre and crystallographer Raymond Batchelor at Simon Fraser University, have described a Cu-Au coordination polymer that can be isolated in one of two polymorphic forms depending on the synthesis conditions. More remarkably, the two polymorphs act as colourometric sensors for a variety of volatile organic compounds (VOC’s) and may have applications as sensors for these environmental pollutants. The materials are self-assembled co-polymers prepared by the reaction of Cu(II) salts with KAu(CN)2 in dimethyl sulfoxide (DMSO). Dilute solutions give a green polymorph (1), while rapid precipitation from a concentrated solution gives a blue solid (polymorph 2). The structures of the two polymorphs are significantly different. Please see colour figures 1a and 1b on p. 39. In 1, the Cu is 5-coordinate, bound to two DMSO molecules, and three CN groups, which hold the material together via Au bridges. Two of the Au units act as part of the main chain of the coordination polymer and the third is dangling. In polymorph 2, Cu is present in a distorted octahedral geometry,

with two DMSO molecules at approximately 95 degrees from each other instead of the 180 degrees separation characterizing 1. The overall structure of 2 is a herringbone-type arrangement of Cu and Au units, with the individual polymer chains held together by Au-Au interactions between the different chains. Thus the two polymorphs are different colours because of the different coordination numbers and geometries of Cu in the two materials. Please see the colour figures 1a and 1b on p. 39. Both polymorphs display vapochromic behaviour upon exposure to VOC’s and other solvents. In other words they change colour. When exposed to water vapour at room temperature, the coordinated DMSO molecules are replaced with water molecules resulting in a lime-green/yellow material. Interestingly, both 1 and 2 convert to the same structure and the displacement is mostly reversible—DMSO can be re-introduced by changing the atmosphere, but only polymorph 1 is produced indicating that it is likely the thermodynamically more favoured form. Compounds 1/2 also act as reversible sensors for dioxane, DMF and acetonitrile (Figure 2), however strongly coordinating solvents such as ammonia and pyridine are not easily displaced. In all cases the change in colour is caused by binding of the new solvent molecule to the central Cu, not by merely absorption of the Cu into pores in the structure (see Figure 3 for the structure of the pyridine-coordinated material). The cyanide region of the IR spectrum is also very sensitive to changes in bound solvent, providing another detection handle. Leznoff and coworkers attribute the variety of structures that can be accommodated by the coordination polymer to the high degree of flexibility imparted by the ability of Cu to support several coordination geometries and numbers, and the presence or absence of stabilizing Au-Au interactions. Please see the colour figures 2 and 3 on p. 39.

Chirality transfer in the Stille reaction In the Stille reaction, an organic group attached to tin is transferred to another organic group with formation of a carboncarbon bond using catalytic amounts of palladium. In general, the organic group is sp2-hybridized such as a vinyl or aryl group, such that the group to be transferred is easily differentiated from the other three groups on tin, which are generally butyl groups. In a recent issue of the Journal of the American Chemical Society, chemistry professor J. Michael Chong and graduate

Equation 1 student Kevin Kells from the University of Waterloo have reported conditions under which the Stille coupling occurs on an extremely interesting substrate. The Waterloo group demonstrated that a carefully designed alkyl group can be transferred specifically in the presence of the butyl groups on tin, and with no loss of stereochemistry. In order to prepare the chiral organostannane, the Chong group starts with an imine substituted with a sulfinyl group as a directing group (chiral auxiliary) such as 3. Reaction of 3 with lithium tributylstannane occurs with high levels of diastereoselectivity, such that only one isomer of 4 is observed. However, all attempts to react sulfinamides 4 directly in the Stille reaction failed. Remarkably, oxidation to the sulfonamide derivative 5 proved to activate the substrate toward the Stille reaction. In the presence of highly basic bulky aryl phosphine ligands, 5 reacts with acid chlorides to give coupling products 6 in high yields (up to 98 percent) (Equation 3). Chelating ligands such as DPPE, give substantial amounts of imine 7, which is produced by beta-hydride elimination at the intermediate Pd complex. In all


Equation 2 cases, the Stille coupling product 6 was isolated with >98 percent enantiomeric excess, indicating that the chirality was transferred completely from 5 during the reaction. Furthermore, the reaction proceeds with inversion of stereochemistry, implying that the reaction occurs via an SE2 type process for the transmetallation step, as originally proposed by Stille over 20 years ago. Since the sulfonyl group can be easily removed, the sequence described by the Chong group represents a useful preparation of chiral alphaamino ketones.

Nano-sized holes enhance Raman and SPR spectroscopy When light strikes a metal film that contains a regular array of nanometer sized holes, an interesting and counter-intuitive optical effect is observed. About five years ago it was shown that the amount of light that exits these tiny holes is about twice the amount of incident light. This implies that even light striking the metal film between the holes is transmitted by them! This enhanced transmission is strongly wavelength dependent and extends to wavelengths that are much larger than the hole diameters or even the spacing between holes (Nature 391,667,1998). It was shown that surface plasmons—the collective oscillation of free electrons in resonance with the electromagnetic field—are responsible for this remarkable enhancement.

In two recent publications, the research group of Alexandre G. Brolo (University of Victoria (UVic), chemistry) in collaboration with Reuven Gordon (UVic, electrical and computer engineering) and Karen L. Kavangh (Simon Fraser University (SFU), physics) has demonstrated that these arrays of nanoholes can be used to build chemical sensors. The nanoholes were fabricated by SFU’s graduate student Brain Leathem using a focused ion beam. In one design, it was shown that a chemical binding event that changes the dielectric constant of the metal surface causes a shift of the surface plasmon resonances (Langmuir, 20 (2004) 4813). This causes a considerable shift in the wavelengths of the light that are transmitted through the nanoholes (Figure 4). Although “conventional” surface plasmon resonance (SPR) spectroscopy is common in the characterization and quantification of chemical and biological binding events, “Chemical Shifts” has been told that in actuality SPR is notoriously sensitive to alignment, surface preparation, moon phases, and the amounts of coffee consumed prior to measurement. On the other hand Brolo states that the SPR sensor based on nanoholes is much more straightforward to use since the signal is measured in straight transmission. Also a much smaller area may be interrogated, leading to a much simpler and more compact instrument and a better spatial resolution for example in patterned biosensor arrays.

Figure 4. A nanohole SPR sensor showing red-shifts in the transmission resonance. The left-most curve is for bare gold, the middle curve is obtained after the absorption of an MUA monolayer, and the right curve is obtained after the absorption of proteins on top of the MUA monolayer. In a continuation of this work, Brolo and undergraduate student Erin Arctander with their collaborators have shown that Raman scattering is also enhanced by the tightly confined surface plasmons (Nanoletters, 2004; 4(10) 2015). It is particularly interesting that their surface-plasmon enhanced Raman sensor was able to distinguish between different molecules since the Raman enhancement is not only determined by the presence of the molecular electronic resonances, but also by the frequencies of the surface plasmon resonances. These SP resonances in turn can be changed by changing the periodicity and diameter of the nanoholes, providing a handle with which the sensor can be made selective for different molecules. Again, the Raman sensor is unusual because the signal is picked up in transmission and not in the more typical 90 degree geometry.

Cathleen Crudden, MCIC, is an associate professor at Queen’s University in Kingston, ON. Hans-Peter Loock, MCIC, is an assistant professor at Queen’s.



FOR FUELS AND INDUSTRIAL PRODUCTS Capturing Canada’s natural advantage

“Until the middle of the nineteenth century the demand for lubricants and illuminants was serviced by vegetable and animal oils . . . But through the invention of various distillation processes, oils suddenly became an interesting commodity.” Bjørn Lomborg, The Skeptical Environmentalist


ore than 300 Canadians from industry, academia, and government have participated in this industry-led exercise, championed by Rick Smith, CEO of Dow AgroSciences Canada Ltd.

The vision

J. E. Cunningham

of life through the development and commercialization of industrial bioproducts and processes from our abundant biomass resources. Biofuels and bioproducts are potentially cleaner and cheaper than fossil-based products. They are also renewable, unlike fossilbased products. Biofuels and industrial bioproducts contribute to sustainability and growth. A theme running through the roadmap is the potential of new biotechnologies to capture economically viable materials and energy from biomass such as underutilized materials now being harvested and those from land that is not currently being utilized. The report covers a number of chemical and bioconversion technologies, and identifies both immediate and future markets for the bio-based economy. Another recurring theme is “your waste is my feedstock.”

The overarching vision is to make Canada a leader in environmental and sustainable technologies through its “green advantage” and to grow the economy while improving our environment and quality


It makes sense for Canada! Canada has a natural advantage—it has rich resources of renewable biomass for the manufacture of fuels, chemicals, and materials.

The energy potential of Canada’s biomass carbon Energy is central to Canada’s sustained economic growth, and it is becoming progressively harder or more costly to extract from fossil sources. Demand for energy worldwide is expected to continue to grow rapidly in the foreseeable future as economic development and industrialization become more globally pervasive. The International Energy Agency (IEA) forecasts that the world will require 50 percent more energy over present consumption levels by 2020. Global pressure is building to allocate fossil fuels more wisely and to develop ways to diminish existing dependencies and vulnerabilities. As the amount of readily available oil is depleting, especially in OPEC countries, oil prices will increase, and spikes in energy prices will become even more pronounced. The conflict between price and availability could conceivably become more severe in the next 20 years, resulting in a major paradigm energy shift into future fuels and highly efficient energy systems such as fuel cells, small- to mediumscale distributed cogeneration systems and biofuels (biogases, biodiesel, bio-oils, and alcohol).

The bioenergy cycle Biofuels and bioproducts are strategically important to Canada. There are several successful Canadian companies actively engaged in this field. Canada is in an excellent position to benefit with its resource base, expertise, and developing community-based, eco-industrial clusters. The biomass opportunity will provide new revenue streams for the traditional agricultural, forestry, and marine resource sectors and communities. Major benefits can be derived from Canada’s exceptionally large biomass resource—Canada’s “green advantage.” For instance, the BIOCAP Foundation estimates that our standing forests have an energy content that is equal to 69 years of


Canada’s current energy demand that is met by fossil fuels. Due to a highly unstable energy market globally as well as large spikes in oil and natural gas prices, Canada is at a pivotal point regarding future fuel developments. Action must be taken now. Substantial biofuel opportunities both now and in the near-term future are ours to lose despite our abundant biomass resources and strong competitive advantages. This is the case especially in the physical, chemical, and thermal conversion and in the bio-processing of residue biomass to bio-based energy and industrial products.

The new biorefinery The business case for future biofuel and bioproduct developments, however, needs to be better developed and more widely communicated. The roadmap focuses on taking advantage of commercial opportunities, increasing biomass productivity, and capturing value from agriculture, forestry, marine industries, and municipal solid waste. Canadian companies are exceptionally well positioned to capture strong financial and economic returns from residue biomass material. The return on investment is healthy for many Canadian companies in this business. Industry research and development is close to the market and is, in many cases, at a strong commercialization phase. A transition is occurring in Canada from our current excellence in physical, chemical, and thermal conversion technologies to a greater longer-term emphasis on bioprocesses and “green” chemistry, which are much less energy intensive and less polluting. The body of this innovation roadmap discusses this transition and multidisciplinary approaches involving biotechnology, chemistry, nanotechnology, biology, physics, engineering, and mathematics in greater detail. This roadmap recommends several specific actions that should take place in order to grow the biofuels and bioproducts industries. The following key action items are elaborated in the main body of the report: • Community-based eco-industrial clusters projects; • Government procurement; • Creation of a Bioproducts Industry Council; • Greater capital availability;

• Greater migration of the technology platforms to market-driven commercialization initiatives; • Greater engagement and awareness of the public. This roadmap is a continuous “living” process that allows industry players to work with governments and academia to design their own longer-term plans. This report suggests various technology and market-driven pathways. It also suggests specific actions for both the short and the long term that could be followed. The production of this document is one point on the road in a long and uncompleted journey. New technologies and innovative uses of biomass will continue to evolve from the ongoing discussions that our network or community of practice has initiated. The roadmap has brought a group of individuals together representing a wide range of different interests comprising chemical conversions, combustion, bioprocesses, harvesting and distribution technologies, agriculture, forestry, municipalities, and marine life. The synergy developed through this roadmap needs to be continued and developed further through sustained interactions and networking among the participants, who have contributed an enormous amount of their time and resources to this effort. The roadmap is complete and was launched by National Science Advisor, Arthur J. Carty, HFCIC, as part of his Keynote Address, “Building a Globally Competitive Canada in Biotechnology,” at Bio-North 2004 on November 29–December 1, 2004 in Ottawa, ON. The roadmap is available on the these Web sites: • home_e.html •

J. E. Cunningham is the senior commerce officer at the Manufacturing Industries Branch of Industry Canada.

THE DEOXYGENATION CHALLENGE Turning sugar polyols into a new and renewable resource base for the petrochemical industry


ew homogeneous ionic hydrogenation and hydrogenolysis catalysts could offer a pathway for the efficient transformation of renewable naturally abundant sugar poly alcohols to polymer building blocks.

Sugar poly alcohols as a renewable resource Today practically all commodity chemicals and polymer components are synthesized from alkanes and arenes obtained from either crude oil or natural gas. Over the past century a vast and sophisticated body of knowledge has been developed that allows the efficient refining and chemical transformation of these underfunctionalized feedstocks to alcohols, aldehydes, carbonic acids, amines, nitriles, urethanes, etc. through various catalytic processes operating on a huge scale. The selective activation of C-H bonds is the core theme of all these processes. A possible alternative to fossil carbon resources are the C-3 to C-6 building blocks abundant in nature in the form of sugar poly alcohols of the general composition HOCH2(CH2)nCH2OH. Among these polyols, glycerol (n=1) and sorbitol (n=4) are already available cheaply and in pure form as either the by-product of bio-diesel production or by the hydrogenation of corn sugar, respectively. Erythritol (n=2) is accessible through the biofermentation of glucose and xylitol (n=3) through acid digestion or pyrolysis of hemi-cellulose containing materials, e.g. corn cobs. When considering these polyols as starting materials for large-scale non-fuel applications one is however immediately faced with a very different chemical challenge: in contrast to the traditional fossil carbon sources they are characterized by an abundance of hydroxyl functions, i.e. are in comparison to hydrocarbons overfunctionalized. Any attempt at integrating them into the existing industrial production chain must therefore begin with a controlled deoxygenation of these molecules. The economically most attractive and technically most useful deoxygenation is the selective

Marcel Schlaf, MCIC

replacement of all secondary hydroxyl functions with hydrogen yielding the corresponding α,ω-diols HOCH2(CH2)nCH2OH. As 1,3-propanediol (n=1) and 1,4-butanediol (n=2) they find direct use in the manufacture of polyesters and polyurethanes such as Sorona™/ Corterra™ and Lycra™, respectively. 1,5-pentanediol (n=3) is used in the synthesis of some specialty polyurethanes and 1,6-hexanediol (n=4) could find use in new polymer formulations or also serve as a potential precursor for Nylon-6,6™ production.

Strategy and challenges One strategy to achieving the conversion of polyols to α,ω-diols is the use of an (iterative) cascade of acid catalyzed dehydrations and transition metal catalyzed hydrogenations of the alkenes and carbonyls and/or hydrogenolysis of the oxygen-carbon bonds in the oxacycles resulting from the dehydration and condensation steps (Figure 1). The strategy hinges on the relatively higher reactivity of the secondary vs the primary hydroxyl functions under acidic conditions biasing the products towards the desired α,ω-diols or their corresponding oxacycles.

Figure 1. Strategy for the transformation of sugar poly alcohols to α,ω-diols.


There are multiple challenges associated with this approach, which are best discussed in the context of actual examples. Figure 2 outlines a pathway for the conversion of glycerol to 1,3-propanediol and its associated challenges. The reaction in Figure 2 is initiated by acid catalyzed loss of water from glycerol to give the highly reactive 3-hydroxy-propionaldehyde intermediate, which then requires a rapid hydrogenation of the carbonyl group to yield the desired 1,3-propanediol. The key challenge here is the competing pathway that through a fast second dehydration step leads to acrolein followed by either hydrogenation to the less valuable n-propanol or worse polymerization or decomposition of acrolein. The development of an economically viable process will therefore require a detailed knowledge of the response of the two (de)hydration equilibria Keq and K′eq to changes in the overall acid and water concentrations and a very fast catalyst

or enol ethers (bottom pathway) and in either case a hydrogenolysis of a secondary carbon-oxygen bond (first or second step in the top or bottom pathway, respectively). High-level quantum-mechanical calculations indicate that the hydrogenolysis steps are thermodynamically feasible and as with hydroxyl functions suggest a bias towards the cleavage of secondary carbon-oxygen rather than primary carbon-oxygen bonds again favouring the desired α,ω-diols as the ultimate reaction products. For any polyol to α,ω-diol conversion a final challenge is the minimization of further acid catalyzed dehydration of the remaining primary alcohol functions followed by hydrogenation to the corresponding alkanes. This again emphasizes the need to gain a detailed knowledge of all (de)hydration equilibria involved and their adjustment by controlling the overall acid and water concentration in the reaction mixture.

Figure 2. Pathways and challenges for the conversion of glycerol to 1,3-propanediol. that ideally would achieve a reaction rate to 1,3-diol that is at least comparable to that of the fast second dehydration step. At approximately equal catalyst and acid concentrations this implies kdiol >> k2 for the rate constants of these steps. The second and equally formidable challenge encountered in the polyol deoxygenations is the formation of oxacycles that have to be cleaved by hydrogenolysis in order to yield the desired α,ω-diols. Figure 3 illustrates this challenge showing potential pathways for the conversion of sorbitol to 1,6-hexanediol via the established isosorbide intermediate as the first condensation product. Depending on the actual (and presently unknown) pathway the reaction will require either a hydrogenation of carbonyl intermediates (second step of the top pathway—analogous to the pathway in Figure 2)


is that the only by-product of the reaction is water and since both the deoxygenated products and the water formed have much lower boiling points than the starting polyols, the process should allow direct reuse of the acidic catalyst solution and at least a semi-continuous operation, if an effective acid/transition metal catalyst system can be identified. The necessary acidic reaction environment immediately suggests the use of a new class of robust cationic electron-poor homogeneous ionic hydrogenation catalysts [1] whose development began with the discovery of non-classical dihydrogen transition metal complexes by Kubas [2] almost 20 years ago. Through a transient “side-on” coordination of H2(g), these complexes activate dihydrogen gas in a heterolytic fashion, i.e. cleave it into a proton and a metal bound hydride ligand. The proton and hydride are then sequentially transferred to an unsaturated bond effecting hydrogenation or—more challenging, but

Figure 3. Potential pathways and challenges for the conversion of glucose to 1,6-hexane diol.

Figure 4. Principles of ionic hydrogenation and hydrogenolysis.

Catalysts In order to be competitive the conversion of polyols to the corresponding α,ω-diols must operate in a single reactor without isolation of the intermediate condensation products. This automatically requires a catalyst stable to acid and water, a combination typically anathema to homogeneous transition metal catalysts. The great advantage of this approach however

thermochemically feasible—to an oxygen-carbon bond effecting hydrogenolysis. Figure 4 illustrates both reactions. Note that the ionic mechanism of either reaction is unique as it does not require the organic substrate to ever directly interact with the catalyst centre. The key feature of these catalysts is that they not only tolerate, but actually require, enhance, and maintain a highly acidic environment by

generating acid through a combination of the proton from H2(g) with a non-coordinating counterion, e.g. trifluoromethanesulfonate (OSO2CF3¯—generally abbreviated as triflate or OTf-) yielding the corresponding acid, in this case HOTf, which then serves as the proton source for both catalytic dehydrations and hydrogenation or hydrogenolysis reactions. Ruthenium and palladium based catalysts, e.g. {[Cp*Ru(CO)2]2(µ–H)}+OTf – (Cp* = η5-C5Me5) and (P-P)Pd(OAc)2, (P-P = bulky chelating diphosphine ligand) of this type being employed in polyol transformations have been reported in the academic [3] as well as the patent literature [4,5] in the past few years, but to date their successes have been limited to the hydrogenation of terminal diol model systems, while their effectiveness with glycerol and higher polyols has so far been marginal. More recently a set of guidelines has been formulated [6] that may aid in the rational and evolutionary design of more active ionic hydrogenation and hydrogenolysis catalysts that address the challenges discussed above. The development of such catalysts will be the key to turning sugar polyols into a new and renewable resource base for the petrochemical industry.

References 1) R. M. Bullock, Chem. Eur. J. 10, (2004), pp. 2366-2374. 2) G. Kubas, Metal Dihydrogen and s-Bond Complexes. Structure, Theory and Reactivity (New York: Kluwer Academic/ Plenum Publishers, 2001). 3) M. Schlaf, P. Gosh, P. J. Fagan, E. Hauptman, R. M. Bullock, Angew. Chem., Int. Ed. 40, (2001), pp. 3887–3890. 4) E. Drent, W. W. Jager, Hydrogenolysis of Glycerol; Shell Oil, Patent WO 09905085, (2000). 5) M. Schlaf, R.M. Bullock, P.J. Fagan, E. Hauptman, Dehydroxylation of Diols and Polyols; Brookhaven National Laboratory, The DuPont Company, Patent WO 0198241 (2001). 6) Z. Xie, M. Schlaf, J. Mol. Cat. A (2005), in press.

Marcel Schlaf, MCIC, is presently an assistant

Call for Nominations to the Canadian Science and Engineering Hall of Fame The Canadian Science and Engineering Hall of Fame was created in 1991 and is now part of the Canada Science and Technology Museum in Ottawa, ON. The objectives are to honour Canadians who have made outstanding contributions to society in developing science and engineering, and to promote role models that will help attract young Canadians to careers in science, engineering, and technology. Nominations for induction to this Hall of Fame can be made by individuals and organizations. Nominations of exceptional chemists, past or present, will be considered. Two or three inductees are selected every year. Inductees will join the ranks of Gerhard Herzberg, FCIC, J. C. Polanyi, FCIC, Raymond Lemieux, FCIC, and Mike Smith, MCIC. Nominations should include as much supporting documentation as possible. The Inductee Selection Committee consists of people from various disciplines, and hence the nomination should be prepared with utmost care and details. Details about the Hall of Fame and the nomination process are available at hallfame/u_main_e.cfm.

professor in the department of chemistry at the University of Guelph.



The Ontario Chemistry Value Chain Initiative forms non-traditional alliances to re-invent the Ontario chemical industry.


he objective of the Ontario Chemistry Value Chain Initiative (OCVCI) is nothing less than the re-invention of the Ontario chemical industry. The OCVCI vision is to make Ontario a global leader in innovation, environmental sustainability, chemical products, technologies, and processes. Its aim is to increase competitiveness of the industry by working together to identify common issues, and bridge the gap between biochemistry and synthetic chemistry. The approach is to scrutinize all the links in the value chain, from raw feedstocks to the end user, and take the opportunity to enhance each of them to grow the Ontario chemical industry in a sustainable way. Valueadding links may be added to the chain, both through the development of new products and the application of newly developed technologies. OCVCI is also focused on finding ways to introduce the use of biochemical feedstocks, in addition to synthetically produced feedstocks, to improve the quality and sustainability of production. This could also lead to reduced environmental impact up and down the chain. A driving issue of the OCVCI is the current limited commercialization of product and technology ideas developed in government and academic labs with government funding. There is almost no framework for delivering these ideas to market, and this homegrown resource goes untapped or is exported to other markets. OCVCI was created as a response to the huge changes in the structure and economics in the international chemical industry that have taken place in the last two decades. The U.S. industry has gone from a $20 billion trade surplus in the chemical sector to a $10 billion trade


Bernard West, MCIC, and Joanne West

deficit in just under two years. The Canadian industry has been radically changed and our infrastructure and demographics are aging; innovation is needed. The E.U. and U.S. have recognized these realities and are already developing initiatives to respond. Ontario and the rest of Canada must react quickly. Chemical products remain a keystone for almost all other manufacturing industries. However, in the Ontario market, the old chemical industry is eroding from the bottom up. Ontario facilities continue to close, and importation is on the increase. This erosion of the basis of the value chain stifles innovation, and this extends beyond the chemical industry to plastics and other manufacturing, such as auto, aerospace, housing, medical, etc.

Scrutinize all the links in the value chain … and take the opportunity to enhance each of them Through OCVCI’s initiatives, the industry is responding. OCVCI will build on the potential and synergy that currently exists in the value chain. It has identified some of the policy and systematic barriers and is developing ways to remove these impediments to sustainable growth. And it will identify and facilitate the specific means for sector growth and accelerated development.

Photo by Jason Smith

The results of OCVCI’s work have already begun to emerge. 1. OCVCI is forming partnerships with biobased industries, universities, and federal and provincial levels of government. We are also developing a self-sustaining business model for supporting university research, and accelerating commercialization. 2. A human resources champion committee has been established to ensure that the industry will have the highly trained workforce that it needs to grow in the future. Phase 1 of a GAP analysis has been completed and concluded that the industry will require 13,000 new operators, lab technicians, and maintenance staff over the next ten years. Phase 2 is about to begin with an emphasis on developing a ten-year labour force strategy and to identify how to meet the needs for training. 3. The regulatory and standards setting process should be objectives based, and based on good science. The approval process for products and processes should have a “one-stop” place to go to help prospective entrepreneurs commercialize their ideas. There is also a need for the development and support of a testing infrastructure so that innovative products

can be commercialized throughout the value chain. For example, new products should be introduced to the building code and then used. In conclusion, we have a strong industry, and we must answer together the questions of how to keep it and expand it. We must bring together agriculture, biology, and chemistry to build the future industry. There are many innovation opportunities, and we must bring together entrepreneurs and reliable funding for commercialization to realize them.

Bernard West, MCIC, holds a BSc and PhD in chemical engineering from the University of Manchester and has held leadership positions in the Canadian Chemical industry for over 40 years. He is currently owner and president of Westworks Consulting Limited. West has been on the boards of several industry associations in Canada and the U.S. He is currently vice-chair of the CIC and co-chair of the Ontario Chemistry Value Chain Initiative. Joanne West is a Toronto-based freelance writer.


There is a lesson to learn from the Ontario wine industry. Originally, a big commodity industry protected by a duty barrier, it was expected to be destroyed by free trade. Instead, the industry was able to tap into a growing demand for higher quality specialty products and boom. This transformation was accomplished with the adoption of new technology, entrepreneurial risk-taking and promotion, and active government support. The chemical industry must take similar advantage of new market demands—such as environmental demands, the new technologies being developed within Canada, and the fuel economy, etc. With government support, we must attract a new entrepreneurial spirit to the industry. The OCVCI supports building value chain delivery systems that involve all participants including primary chemical manufacturers, venture capital, the bio-based industry, research and educational institutions, and the provincial and federal governments. Non-traditional industrial alliances must be formed. Innovative technologies must be pulled from Canadian research labs and into commercialization, and there must be improved alignment between research and the needs of the market. Existing restraints to the commercialization of new technology need to be identified. There must be collaboration across the industry to eliminate them. A key constraint remains a lack of commercialization funding. Although R&D is well funded, the ideas stall, because there is no “bridge or transition” funding between the last stage of development and the product commercialization step. A renewed appreciation of the value of bioproduct must be part of the chemical industry’s renewal strategy. Historically the basis of all chemical production, bioproducts offer new opportunities today. They can be used as intermediate chemical feedstocks, provide renewable fuels, functional fibres,

and forestry opportunities. Bioproducts will be important to create the environmentally sustainable chemical industry we want for the future. OCVCI’s priorities to enhance business growth are threefold. 1. To improve the commercialization of innovative products and technologies through the establishment of a linked taskforce between industry and government to remove barriers to commercialization. There must be a one-stop, objective-based standards and regulatory approvals, and the development and support of a testing infrastructure for innovative products throughout the value chain; 2. To improve industry competitiveness. The industry needs to develop an “ESTAClike,” but self-sustaining, innovative delivery system. And it must support improvements in the environmental sustainability of products through government procurements and mandates; 3. To recognize and support our vision for the future of the Ontario chemical industry.

S H A R E YO U R M E M O R I E S !

Historically the basis of all chemical production, bioproducts offer new opportunities today

Share your CIC memories and memorabilia with ACCN. Send your materials to or mail them to the National Office. Please label each piece with your name, a caption, and your complete address to ensure its safe return to you.


FRENCH FRIES FUEL THE FUTURE Visualize french fries as a solution to the energy crisis … a hands-on look at the development and implementation of biodiesel fuel.


new project by environmentally aware students may change the way we fuel our cars, save us from the collapse of the oil industry, and clean up the air. All the while, ensuring good quality french fries. There’s something new in the air at the University of British Columbia (UBC). Strolling among the pine trees along West Mall road, you might catch a whiff of french fries where a campus vehicle is cutting the grass. No, you’re not breathing in the lunch-time waft from The Barn. What you detect is biodiesel fuel in action.

A van and a plan It all started one beautiful summer day a few years ago, when UBC science students Peter Doig, ACIC, and Geoff Hill headed out on their regular back-country excursion to find new rocks to climb. In the pristine beauty of their surroundings they noticed something was out of place. With windows open to let in the fresh air, they smelled the exhaust from their van. “This is not cool,” they thought. They decided to put their educations to work by producing a clean fuel and, in a eureka moment, committed to making biodiesel fuel. Geoff founded the biodiesel project in January 2002 and applied for grants from VanCity and HRDC to help start it up. In January 2003, Peter Doig set some wheels in motion by approaching Naoko Ellis, a professor in chemical and biological engineering at UBC who had sent out a call for fourth-year student projects on alternative fuels. She was very enthusiastic about this project and assisted with the start-up. Doig and Hill’s first order of business was to develop a methodology that would incorporate existing biodiesel production techniques to a scaled down project using waste cooking oil. When Rudolph Diesel developed his engine in the 1890s, he designed it to run on vegetable oil, so it was ideal for the project. Existing techniques for turning vegetable oil into a useable fuel are


Katie Eliot

huge in scale, and don’t normally utilize used oil, but the project had a virtually unlimited supply from UBC cafeterias. The oil is first put through a process that eliminates fatty acids, then is mixed with methanol (supplied by Methanex) by way of a catalyst (usually sodium or potassium hydroxide), then is purified and evaporated through a still. This results in an output of methyl ester (the biodiesel fuel), with small amounts of glycerine, alcohol, and fertilizer. Nothing is wasted in this process.

The biodiesel lab Once the project was approved by senior administration, it got underway in the summer of 2003. The initial phase involved Perrin Hayes, an operations worker at Simon Fraser University (SFU), who loaned his 60 litre biodiesel reactor for tests. This informal phase moved from a corner of the (appropriately named) Gas Gunn building to a 60 square foot storage shed in the lower mall research station. Adjacent space was gradually cleaned out and The Lab (as project members call it) expanded to three times its initial size. The container drums, distillation equipment, tubes, and a cooker were installed; the department of chemical engineering did safety inspections, then production began. This work-in-progress looks like a still you’d expect to see in some moonshiner’s back forty with its conglomeration of tubes, piping, and a huge vat to catch the distilled good stuff. The lab is now producing a clean and efficient fuel at a rate of 100 litres per week. The process was recently automated to reduce labour intensity, and the system can be controlled and monitored remotely. But it’s a hands-on process to collect the necessary bio-waste to produce the fuel. Two students, working with the Environmental Youth Alliance on campus, spend eight hours every two weeks collecting waste cooking oils from UBC cafeterias. Instead of paying an outside company to remove this waste, UBC Food Services benefits from free oil removal, straight to the biodiesel lab. The collectors get to see the chemical process as well as an

Photo by Ingrid Müller

understanding of the distribution process so that they can take this model to other communities. The saving is dramatic: fresh oil such as rapeseed, costs $.70/litre, while reduction companies charge $.50/litre for used oil. With UBC-supplied waste cooking oil, costs run at $.20/litre. The oil is free but costs include student wages, transportation, and other factors. UBC Plant Ops has agreed to run all campus lawn equipment with a 20 percent biodiesel blend for the next few months, to determine if long-term usage and an increase in infrastructure are viable options for this fuel switchover.

Norman Woo conducts a biodiesel experiment at the Quesnel fall fair.

The reality The UBC biodiesel project’s output could be increased to a maximum of 1,000 litres per week, according to Norman Woo, another key member of the project. He is completing his master’s degree in chemical and biological engineering at UBC and started working on biodiesel in June 2003. “I like the idea of recycling a waste stream into a useable commodity, not to mention a more environmentally clean fuel,” he says. As supervising facility engineer, he is involved with all facets of the project. Plans include running a test diesel engine, in partnership with the department of mechanical engineering, to determine running mixtures and injector clogging.

So, is less more? This would appear to be the case. A small-scale production facility for biodiesel fuel has large-scale implications. It’s a portable system: communities including Bowen Island and Quesnel hosted biodiesel project demonstrations by Woo and have called for feasibility studies. The City of Richmond fleet manager is committed to increasing its use of biodiesel fuel for city vehicles to 100 percent over the next few years. Hypothetically, UBC’s maximum biodiesel production of 1,000 litres per week could fuel 15 one-ton trucks to run 250 km each. Better still, this output could

fuel 60 cars with diesel engines, assuming 1,000 km per tank. At $.20/litre, you can do the math. You now have a clean-burning inexpensive recycled fuel. Somebody pinch me!

The perks Benefits go beyond cost and are equally appealing. We know that petroleum won’t last forever: one source (Harper, 2000) estimates viable stocks will all be used by 2059; another source (Heinberg, 2003) estimates that oil production will peak by 2015. Other fuel sources are not only desirable but imperative. Health benefits, estimated by the U.S. Department of Energy, include reduced exposure to emissions of carbon monoxide (43 percent reduction at

100 percent mix, or 13 percent reduction with a 20 percent mix); hydrocarbons (56 percent and 11 percent respectively); loosely defined air toxics (75 and 15 percent) and reduces cancer risk by 94 and 27 percent. The main components of smog are particulate matter and ground-level ozone. Using a 20 percent blend of biodiesel lowers these emissions by half, and CO 2 by nearly 20 percent, which would help Canada meet its Kyoto protocol commitment. In addition, biodiesel is 10 times less toxic than table salt, which means a major spill would be messy, but far less damaging to the environment than a major spill of petroleum. These are good numbers and with healthcare costs climbing, anything that promotes better health will be in demand. Going one step further, a major by-product of biodiesel production is glycerine, which Naoko Ellis, MCIC, is working to utilize. This complements her research on bio-oils. She recently was awarded an NSERC strategic grant for the Biocap Program (biomass fuels, specifically wood wastes) and stresses that a diversity of strategies for fuel sourcing is necessary. Fuel cells, such as those produced locally by Ballard Power, run on hydrogen and still rely on petroleum to supply it. Bio-oils and biodiesel are environmentally friendly sources of hydrogen for these new fuel cells. But her biggest turn-on with this project? “Talking with students who want to be involved. They get so excited about participating in research for this project.” Ellis hopes that projects such as biodiesel become a major part of the sustainability initiative that has garnered international recognition for UBC. Norman Woo cites the unique partnership this project fosters among UBC, private funders (Methanex), and a not-for-profit organization, the Environmental Youth Alliance. The federal department of transport has also contributed $50,000 for facility design and materials. This structure can concentrate on the work at hand and not be subject to shareholders and red tape that generally constrain larger companies. The UBC sustainability office has brought the necessary players together through its Social, Ecological, Economic Development Studies (SEEDS) program. SEEDS manager, Brenda Sawada, explains how citing the project on campus within an academic discipline, along with developing a business plan and starting the engine testing, have contributed to the project’s momentum and credibility.


The ripple effect


One of the most exciting parts of the biodiesel project is the ripple effect. Five Sauder School of Business students prepared a business development plan for the project in April 2003. They note this project is the first communitysized facility of its kind and would be ideal for universities. Harvard University has recently switched to running all of its diesel vehicles on biodiesel. As well, more UBC science and engineering students are taking courses on alternate fuel technologies. As Karun Koenig, head of the Environmental Youth Alliance on campus says, “Even if someone from this project goes to work in the petroleum industry, that person can introduce some change and bring a part of the biodiesel sustainability model to that other industry and benefit it.


Even if they go mainstream, they still carry the spirit of our work here.” Meanwhile Peter Doig and Geoff Hill are carrying their environmental commitments forward. Peter is completing his master’s degree in bio-resource engineering at UBC and is currently working with a local company on organic pesticides. Geoff is somewhere deep in the BC woods working on sustainable forestry practices. The biodiesel seeds they helped plant are beginning to yield a bumper crop here at UBC. Biodiesel fuel produced from waste oils is a huge paradigm shift that even the federal government is encouraging. With its renewed commitment to developing green power markets, producer support, and tax incentives, the feds may consider this biodiesel project an ideal candidate for partnering in

tech innovation as well. The future looks bright. And clear, too: no more black fumes spewing from the trucks on our streets, and our view of the surrounding mountains to the south and east would be restored. We can even start to catch up to Europe, where biodiesel is sold at more than 800 gas stations, or have California follow our lead here. Perhaps Silicon Valley will be giving way to Bio-Mass Valley (Biodiesel North) on the not-too-distant horizon. For more information go to www. or This article was reprinted courtesy of Trek Magazine, University of British Columbia.

Katie Eliot is a Vancouver poet and writer.



CIC Talks to Federal Government As an active member in both the Canadian Consortium for Research (CCR) and the Partnership Group for Science and Engineering (PAGSE), the CIC has met with federal MPs and senior bureaucrats for the past three months to voice concerns about the future of government funding for research. The Trisociety comprised of the CIC, the Canadian Association of Physicists (CAP), and the Canadian Federation of Biological Societies (CFBS) recently met with Arthur J. Carty, HFCIC, National Science Advisor to the Prime Minister. Clockwise starting from the left are Roland Andersson, MCIC, CIC executive director; Jean-Francois Legault, MCIC, CSChE past president; Arthur J. Carty; Don McDiarmid, CAP; Jim Cheetham, CFBS; Mike Morrow, CAP; Francine Ford, CAP executive director; and Bruce Sells, CFBS executive director. CSChE BULLETIN SCGCh

Report on the 54th Canadian Chemical Engineering Conference “ENERGY FOR THE FUTURE” The 54th Canadian Chemical Engineering Conference took place at the Calgary Marriott Hotel and Telus Convention Centre in beautiful Calgary, AB, October 3–6, 2004. Great weather, breathtaking views of the Rockies, stimulating symposia, and a large number of international participants made it a success. With the theme, “Energy for the Future,” the conference attracted over 850 delegates from Canada , the U.S., and a dozen other countries, including a large number from industry. The symposia included numerous technical sessions on oilsands production and upgrading, process systems engineering, new technologies, as well as biotechnology/biomedical, pulp and paper, and others. The student program was made up of competitions, industry tours at Lafarge, Spartan Controls, and the Calgary Centre for Innovative Technology (CCIT), in addition to talks and workshops such as salary negotiation, and multiphase flow and wellbore optimization in oil and gas wells. Over 230 undergraduate students and


close to 240 graduate students participated in these events. Details on competition winners are available in the Student News section on p. 31 of this issue. The conference awards luncheon was also well attended and several chemical engineering professionals and students were honoured for their great work and contributions. The culmination of the conference was of course the western-style blue jeans BBQ where everyone experienced good ol’ fashioned western hospitality and entertainment. The CSChE 2004 conference was another to remember—thanks to conference co-chairs Dan Motyka, MCIC, and John Wood, MCIC, and technical program co-chairs Bill Svrcek, FCIC, and Brent Young, MCIC, and their entire organizing team. The contribution of an important number of volunteers must also be emphasized. Without them, such a venture could not be undertaken. We hope to see you all in Toronto in October 2005 for the 55th Canadian Chemical Engineering Conference!



I’LL ÉTAIT UNE FOIS DANS L’OUEST Toute cette histoire a commencé un mercredi soir. Je reçois un appel d’une amie qui me propose d’aller à Calgary présenter un projet de design sur lequel j’ai travaillé en 2003 dans le cadre de mes études en génie chimique à l’Université de Sherbrooke. Cette présentation fait partie du concours de design offert par la grande firme de génie conseil SNC-Lavallin, et les frais de voyage seraient couverts par l’Université de Sherbrooke et la SCGCh! Il est certain que mes douze coéquipiers n’ont pas pu faire le voyage jusqu’à Calgary pour participer au concours puisque l’Université de Sherbrooke ne pouvait subventionner que trois personnes de l’équipe pour la représenter. C’était donc ceux qui ont su se libérer à temps qui ont participé, en l’occurrence deux de mes coéquipières Karine Bélanger et Catherine Dubreuil, ainsi que moi-même, Jean-Philippe De Serres. La colle c’était que les détails du projet s’étaient retirés dans un coin sombre de mon cerveau et que l’avion quittait trois jours plus tard. Donc, il fallait créer en un temps record une affiche comportant les différents volets du projet. Cependant, un manque de préparation n’étant pas une raison suffisante de voir filer la chance de visiter un coin de mon pays, je me lance dans les préparatifs. J’ai donc quitté Montréal le lendemain pour rejoindre mes deux coéquipières à l’Université de Sherbrooke, à une centaine de kilomètres de chez moi. Il s’ensuit deux jours de brainstorming intense, d’innombrables trous de mémoire et enfin, l’achèvement d’un poster à l’allure sublime et au contenu moins que parfait, mais tout à fait adapté et conforme aux exigences de la compétition. Nous pensions gagner puisque nous savions que notre projet était de loin le plus complet, surtout parce que nous étions treize à l’avoir créé, ce qui est beaucoup plus que les autres équipes. Nous avions entendu parler de la conférence de la SCGCh en 2003 alors que la majorité de notre promotion s’est déplacée à Hamilton en Ontario pour y assister. C’est au cours de cette conférence que l’Université de Sherbrooke a obtenu la première place du concours de design de SNC-Lavallin. Il nous revenait naturellement de défendre l’honneur de l’Université de Sherbrooke et sa première place dans le concours de design de 2004. En plus, le voyage était payé et j’allais prendre quelques jours après la conférence pour visiter les Rocheuses. Le projet soumis par l’équipe de l’Université de Sherbrooke traitait du design préliminaire d’une usine de production de biodiesel.

Cette étude comprenait plusieurs volets dont l’analyse économique, l’analyse d’impact environnemental, la simulation du procédé sur HYSYS, le coût des équipements et l’étude HAZOP. Il s’agissait d’une étude préliminaire très complète qui a plus que mérité sa place parmi les trois finalistes du concours de SNC-Lavallin. Le projet a débuté en janvier 2003 et faisait partie d’une étude effectuée par notre promotion et portant sur l’impact de carburants alternatifs sur l’environnement. Cette étude comprenait le design de l’usine de biodiesel en question, mais aussi le design d’une usine d’éthanol et d’une usine de méthanol. Une fois complété, le projet représentait l’effort cumulé de centaines d’heures de recherche par un groupe d’environ 42 étudiants. Les sujets nous ont été proposés par notre professeur de design, Maher Boulos, suite à une étude superficielle des émissions de GES par différents carburants. Le but était d’obtenir une étude pouvant comparer l’efficacité de ces trois carburants sur un plan économique, énergétique et environnemental. Le voyage en avion vers Calgary se fait dans une tornade de paquets d’amandes fumées miniatures et de pseudo révisions en vue de notre discours devant ce que nous espérions être un auditoire captivé par notre projet. Hélas, ceci n’allait pas être le cas. Enfin je pose les pieds à Calgary, la terre promise de mon père. C’est dans cette ville qu’il ne cesse de me suggérer d’aller faire ma vie. Il me dit que c’est dynamique et jeune comme endroit, alors voici ma chance de le constater de mes propres yeux. L’heure des présentations approche. Nous rencontrons les autres finalistes de la compétition qui nous expliquent alors les points forts de leurs projets. Ces derniers étaient tous de très haute qualité et, par ce fait même, très difficiles à apprécier d’un simple coup d’œil. Heureusement, nous avons eu la chance de dialoguer rapidement avec nos concurrents, ce qui nous a permis d’en savoir un peu plus sur leurs projets qui s’intitulaient Hydrocracking of Vacuum Gas Oil et Atmospheric Hydrochloric and Leach of Nickel Laterite Ore respectivement de la University of Western Ontario et l’Université McGill. La victoire des étudiants de l’Université McGill était bien méritée. Il était temps pour moi de quitter Calgary pour les Rocheuses, où les plus beaux paysages du monde m’attendaient. Jean-Philippe De Serres, ACIC











1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14.

Bill Svrcek, FCIC, technical program co-chair, and friends. The heart of downtown Calgary. The “trees” on Stephen Avenue Walk. Calgary skyline over the tree tops. Students strike a pose at the BBQ at Symon’s Valley Ranch. All smiles. The CIC national office staff takes a breather. Check out the view of the Rockies from the Calgary Tower. Checking the sunny, warm weather from CSChE 2004 headquarters, the Calgary Marriott Hotel. Students enjoy a break between sessions. Publications manager, Michelle Piquette, poses with Nigerian delegate, Victoria Akpomudge. National office student volunteer, Ian Nezier, sports the CSChE 2004 backpack. For sale now! What a shindig! The BBQ at Symon’s Valley Ranch. Cowpokes Bill Svrcek, FCIC, technical program co-chair, and Dan Motyka, MCIC, conference co-chair. Students strut their stuff. Line dancing at the conference BBQ.











CSCT Involved in Accreditation with CTAB

CSChE 2004 Conference Sponsors Patron Syncrude Canada University of Calgary

Elite Bantrel Inc. MEG Worley Limited

Leadership Manulife Financial Meloche Monnex Financial SNC-Lavallin Amec Americas Inc. APEGGA

Corporate John Wiley & Sons Ltd. Aspen Technologies APEGGA Imperial Oil – Products and Chemicals Division NOVA Chemicals Corporation

CSChE 2004 Student Program Sponsors Platinum Institute for Sustainable Energy, Environment and Economy (ISEEE) – University of Calgary Chemical and Petroleum Engineering – University of Calgary Faculty of Engineering – University of Calgary W.Y. Svrcek Engineering Ltd. XEROX Research Centre of Canada


Silver Physical, Theoretical and Computational Chemistry Division Environment Division

CSChE 2004 Exhibitors Bantrel Inc. Coanda Research and Development Corporation

Folio Instruments Inc


The Canadian Technology Accreditation Board (CTAB) is a standing committee of the Canadian Council of Technicians and Technologists (CCTT), created in 1982 from CCTT’s national standards committee. CTAB strives to provide a national accreditation program that enables educational agencies offering applied science and engineering technician and technologist programs to meet the challenges presented by technological change. CTAB is comprised of designates from each province, representing various disciplines in engineering and applied science technology. It also includes representatives from the Department of National Defence, the Canadian Society of Chemical Technologists (CSCT), and the National Council of Deans of Technology. Typical CTAB functions include: • responsibility for the development and management of the national accreditation program. CTAB, in partnership with CCTT’s provincial constituent member associations and societies, evaluates technician- and technologist-level programs across Canada; • partnership in the review and revision of the Canadian Technology Standards (CTS)—CTAB keeps CCTT informed of the evolution of the standards and recommends their use to the CCTT provincial constituent member associations and societies; • responsibility for a central registry of accredited programs, available on CCTT’s Web site; • liaison, through CCTT, with similar organizations in other countries; • promotion of life-long learning for the development and improvement of individual technicians and technologists. Since 1997, CSCT has had an MOU with CTAB, which includes a CSCT board member sitting on the CTAB board. Currently, CSCT has two of their board members train and act as lead assessors for chemical, environmental, and industrial programs. For more information, contact Cathy Cardy, MCIC, CCT, at



Forensic Tour in Ottawa


The Ottawa CIC Local Section held a tour of the RCMP Forensic Laboratory Services, 1200 Vanier Pkwy., Ottawa, on November 29, 2004. Interest was high with roughly 40 CIC members from diverse chemical backgrounds participating. Members toured facilities dealing with explosives, materials profiling, and forensic identification. They heard from experts and were given the opportunity to ask questions.

Reward your advisor’s efforts by nominating him or her for the Student Chapter Faculty Advisor Award. Each Constituent Society offers an award (i.e. three awards are given annually, judging is carried out by each Society). You can find the Terms of Reference below. Nominations are due by March 31, 2005.

den ions. d i b r re fo restrict e w ty os Phot to securi due This was a very successful event! Many thanks go to the RCMP staff who took time out from their very busy schedules to accommodate us, and to the CIC members who showed interest in the tour. The following link will take you to the RCMP Web site where you can find out more about Forensic Laboratory Services: www.rcmp. ca/fls/home_e.htm.

Edmonton Local Sections’ Activities Abound The Edmonton CIC and CSChE Local Sections were busy with activities at the conclusion of 2004. Following the E. Gordon Young Lectureship (see ACCN, January 2005) and the 2004 Boomer Lecture Series, Section members participated in lectures, the opening of facilities, and workshops. November and December 2004 activities included: • A lecture by S. Bergens, University of Alberta, “Towards Rechargeable Fuel Cells that Work on Rubbing Alcohol and Magnetic Resonance Imaging of Operating Hydrogen Fuel Cells”; • Grand opening of the undergraduate NRM at the University of Alberta, which included a tour of the NRM and facilities; • A lecture by Jim Kresta, Syncrude Research, Edmonton, “Lies, Damn Lies, and Statistics,” which was carried out in cooperation with the AIChE; • Nanotechnology Solutions and Opportunies for the Environment Industry Workshops.

Student Chapter Faculty Advisor Award Guidelines 1. The awards shall be presented on an annual basis to one faculty advisor from each Society who has demonstrated exceptional performance working with students to plan and implement Student Chapter activities. 2. The criteria for the awards shall include the following: • evidence of outstanding leadership by the faculty advisor in creating enthusiasm among Student Chapter members; • evidence of creating sustained interest in professional societies; • evidence of continuing involvement in Student Chapter affairs. 3. The awards will be presented at the annual CSC or CSChE conference or at a CSCT symposium. 4. The awards shall be commemorative plaques. 5. The award winners shall be selected from the teaching faculty at any Canadian university or college that has a Student Chapter in chemistry, chemical engineering, or chemical technology, which is registered in good standing with its Society. 6. Nominations for these awards shall be made by the Student Chapter at the university or college at which the faculty advisor teaches. 7. The nominations shall be made in writing and shall be signed by the president and one other member of the Student Chapter and by the head or chair of the department. The nomination forms shall be sent to the student affairs manager at the CIC. 8. Nominations shall be accompanied by supporting documentation, including: • a biographical sketch, curriculum vitae and other pertinent information about the nominee; • a summary of Student Chapter activities over the past three years, especially those attributable in whole or in part to the efforts of the faculty advisor; • a list of Student Chapter involvement in public or off-campus activities. 9. Previous winners of the awards shall not be eligible to receive the awards. 10. Faculty advisors currently serving as directors or officers of the CIC or any of its Constituent Societies shall not be eligible until they have completed their terms. 11. The nominations shall be submitted by March 31 of the year the award is presented. Each nomination shall remain in force for three years and will be considered annually by the Selection Committee. 12. There shall be a Selection Committee consisting of the student affairs Society director, who will chair the committee, plus two additional board members from the Society.



Soumettez la candidature de votre conseiller aux etudiants



Récompensez ses efforts en soumettant sa candidature pour le Prix du conseiller de l’année décerné par la section étudiante. Chaque société constituante offre un prix (c’est-à-dire que trois prix sont octroyés chaque année, chacune des sociétés jugeant ses propres candidats). Vous trouverez ci-dessous les conditions de mise en candidature. Les candidatures doivent nous être parvenues le 31 mars 2005. Directives concernant le Prix du conseiller ou de la conseillère de l’année décerné par la section étudiante 1. Les prix sont présentés annuellement à un conseiller ou une conseillère d’étudiants membre de chaque Société qui a fait preuve d’un rendement exceptionnel auprès des étudiants dans la planification et la mise en oeuvre d’activités conçues pour la section étudiante. 2. Les critères de remise des prix sont les suivants : • preuves que le leadership du conseiller ou de la conseillère a suscité l’enthousiasme chez les membres de la section étudiante; • preuve de la création d’un intérêt soutenu à l’égard des sociétés professionnelles; • preuve d’une participation continue aux affaires de la section étudiante. 3. Les prix sont présentés au congrès annuel de la SCC, la SCGCh ou au symposium de la SCTC. 4. Les prix ont la forme de plaques commémoratives. 5. Les gagnants et les gagnantes des prix sont sélectionnés parmi les membres du corps enseignant de n’importe quel université,


9. 10.



collège ou cégep canadien ayant une section étudiante en chimie, génie chimique ou chimie technologue dûment inscrite auprès de sa société respective. Les candidates et les candidats à ces prix doivent être choisis par la section étudiante de l’université, du collège ou du cégep où le conseiller ou la conseillère travaille. Les mises en candidatures doivent être faites par écrit, en utilisant le formulaire approprié, signé par le président ou la présidente ou un autre membre de la section étudiante, ainsi que par le chef/directeur ou la chef/directrice du département. Les formulaires de mise en candidature doivent être envoyés à la directrice des affaires étudiantes à l’ICC. Les formulaires de mise en candidature doivent être accompagnés d’une documentation appropriée comprenant : • une brève biographie, un curriculum vitae et d’autres renseignements pertinents concernant le candidat ou la candidate; • un résumé des activités des trois dernières années de la section étudiante, particulièrement de celles qui sont attribuables en tout ou en partie aux efforts du conseiller ou de la conseillère d’étudiants; • une liste des activités publiques ou hors-campus auxquelles la section étudiante a participé. Les personnes qui ont déjà remporté les prix ne sont pas admissibles à d’autres mises en candidatures. Les conseillers ou les conseillères d’étudiants assumant des fonctions d’administrateur ou d’administratrice ou d’autres fonctions officielles au sein de l’ICC ou de ses sociétés constituantes ne seront admissibles qu’à la fin de leur mandat. Les candidatures doivent être soumises avant le 31 mars de l’année précédant la remise du prix. Chaque candidature reste en vigueur pendant trois ans et est réexaminée chaque année par le comité de sélection. Le comité de sélection est présidé par l’administrateur de la société chargé des affaires étudiantes et comprend deux autres membres du conseil d’administration de la société.

Occasionally, our membership list is made

Respecting your privacy is important to us

available to reputable companies and organizations whose products and services may be of interest to you. If you prefer not to have your name made available, please contact us at the following address:

Membership Services The Chemical Institute of Canada 130 Slater Street, Suite 550 Ottawa, ON K1P 6E2 Fax: (613) 232-5862



Results of the 54th CCEC Student Competitions

csct western canadian student symposium


Undergraduate and graduate student competitions were held at the 54th Canadian Chemical Engineering Conference in Calgary, AB, in October 2004. Here are the final results of these competitions.

Undergraduate student competitions SNC-Lavalin Student Plant Design Competition • First place: McGill University team Beatriz Myra Alvarade, Ethan DeFord and Rima Manneh for their design “Atmospheric Hydrochloric Acid Leach of Nickel Laterite Ore” • Second place: Université de Sherbrooke team Karine Bélanger, Nathalie Camiré, Philippe Chouinard, Jean-Philippe De Serres, Nicole Desnoyers, Catherine Dubrueuil, Maxim Duchesne, Pierre-Luc Girard, Dragana Hann, Daniel Laflamme, François Laflamme, Odile Lamarche, and Julie Tremblay for their design, “Rapport d’ingénierie préliminaire pour la production de biodiesel” • Third place: University of Western Ontario team Khaled Abdel-Gawad, Mustafa Al-Sabawi, Wailan Chan and Derek Daniher for their design, “Hydrocracking of Vacuum Gas Oil” Robert G. Auld Student Paper Competition • First place: Tanya Hauk, University of Toronto • Second place: Karina Lorenzo, University of Toronto • Third place: Sarah Evangelista, McGill University Reg Friesen Oral Paper Competition • First place: Agnes Durlik, University of Toronto • Second place: Caroline Wilson, University of Alberta

Graduate student competition ISEEE Graduate Student Paper Competition • First prize: Babak Jajuee, University of Western Ontario, “A Mechanism of Surface Renewal-Stretch Theory: Application to Interface Mass Transfer” • Second prize: Maryam Jafari, University of Calgary, “Elasticity of a Model Oil/Water Interface” • Third place (tie): Tony Y. Wang, University of Calgary, “Dynamic Behaviour of Neurosphere Cells in Expanding Populations of Neural Stem and Progenitor Cells” Haslenda Hashim, University of Waterloo, “An Optimal Fleet-wide CO2 Emission Strategy for Ontario”

YOUR CHANCE TO BECOME THE EXPERT when: March 18 and 19, 2005 where: SIAST Kelsey Campus, Saskatoon, SK contacts:

Shauna Bulmer, MCIC Scott Sawyshyn Eric Mead, FCIC

$2,000 in prizes for top presenters!

CSC STUDENT CONFERENCES FOR 2005 march 19 – Southwestern Ontario Undergraduate Student

Chemistry Conference (SOUSCC), University of Toronto, Toronto, ON. Contact: may 5–7 – Western Undergraduate Student Chemistry

Conference, University of Victoria, Victoria, BC. Contact: Christine Tong at may 12–15 – ChemCon2005 (CIC-APICS Atlantic Student

Chemistry Conference), Memorial University of Newfoundland, St. John’s, NL. Contact: Skylar Stroud at or visit their Web site at october 28 – Colloque annuel des étudiants et étudiantes de 1er cycle en chimie, Université de Sherbrooke, Sherbrooke, QC. Contactez : Pierre Harvey a november 10–12 – 2nd Banff Symposium on Organic Chemistry, Banff, AB. Contact: BSOC organizing committee at or visit their Web site at november – Chemistry and Biochemistry Graduate Student Conference, Concordia University, Montréal, QC.


THEYâ&#x20AC;&#x2122;VE DONE IT AGAIN!

CHOOSE YOUR VALENTINE Order your copy of the zany, madcap, slightly overexposed and informative Chemistry Club Calendar 2005. Just $12.00! To order, send $12.00 plus tax to the University of Winnipeg Chemistry Students Association, 515 Portage Ave., Winnipeg, MB R3B 2E9.


A publication of the CIC/Une publication de l’ICC

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Send your reply to FEBRUARY 2005 CANADIAN CHEMICAL NEWS 33




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Canada Conferences May 9–11, 2005. 9th Annual Advanced Process Control Appliance for Industry Workshop: APC 2005, Vancouver, BC. Contact: Guy Dumont; Web site: July 31–August 4, 2005. 18th Biennial Chem Ed Conference, University of British Columbia, Vancouver, BC. Web site: August 19–26, 2005. 20th International Symposium on Polycyclic Aromatic Compounds (ISPAC 20), Toronto, ON. Contact: Chris Marvin; Tel.: 905-319-6919; E-mail: August 19–26, 2005. 25th International Symposium on Halogenated Environmental Organic Pollutants and POPs (Dioxin 2005), National Water Research Institute, Toronto, ON. Contact: Mehran Alaee; Tel.: 905-336-4752; E-mail: mehran.; Web site:

U.S. and Overseas June 20–24, 2005. 2nd International Conference on Green and Sustainable Chemistry and the 9th Annual Green Chemistry and Engineering Conference, Washington, DC. Contact: Robin Rogers; E-mail: July 10–15, 2005. 7th World Congress on Chemical Engineering (WCCE7), IchemE and the European Federation, Glasgow, Scotland. Contact: Sarah Fitzpatrick; E-mail: sarah. August 13–21, 2005. IUPAC 43rd General Assembly, Beijing, China. Contact: IUPAC Secretariat; Tel.: +1 919-485-8700; Fax: +1 919-485-8706; E-mail:


Department of Chemistry The Department of Chemistry, Memorial University of Newfoundland, invites applications for tenure stream appointments at the rank of Assistant Professor in the areas of Inorganic Chemistry and Experimental Physical Chemistry, effective on or after July 1, 2005. Memorial is a modern university with an undergraduate student enrolment of almost 18,000 and M.Sc. and Ph.D. programs in all the major areas of science. The Chemistry Department currently has 17 tenured faculty, about 45 graduate students and post-doctoral fellows in NSERC supported research programs, and is equipped with modern research instrumentation in all areas of chemistry. Applicants must possess a Ph.D. or its equivalent in Inorganic or Physical Chemistry, and have a strong academic and research background. The successful applicants will be expected to develop internationally recognized research programs, and contribute to teaching at both undergraduate and graduate levels. Research proposals will be evaluated on the basis of excellence, and contributions to the Department’s areas of strength (see and the University’s strategic plan. Salary will be commensurate with qualiÞcations and experience. Applicants should provide a curriculum vitae, a list of publications, a statement of research interests and a research proposal, and should arrange to send the names and addresses of at least three referees. Applications will be considered from March 1, 2005 until the positions are Þlled. Memorial University is part of a vibrant, local scientiÞc and engineering community. Partners of candidates for these positions are invited to include their resumes for possible matching with other job opportunities; the University maintains an inventory of available positions. Memorial University is committed to employment equity and encourages applications from qualiÞed women and men, visible minorities, aboriginal people and persons with disabilities. All qualiÞed candidates are encouraged to apply; however, Canadians and permanent residents will be given priority. Memorial University is the largest university in Atlantic Canada. As the province’s only university, Memorial plays an integral role in the educational and cultural life of Newfoundland and Labrador. Offering diverse undergraduate and graduate programs to almost 18,000 students, Memorial provides a distinctive and stimulating environment for learning in St. John’s, a very safe, friendly city with great historic charm, a vibrant cultural life, and easy access to a wide range of outdoor activities. Dr. Robert W. Davis, Head, Department of Chemistry Memorial University of Newfoundland St. John’s, Newfoundland, Canada, A1B 3X7 Telephone: (709) 737-8772; Fax: (709) 737-3702 E-mail:


Chemical Shifts

continued from page 12

Figure 1a (polymorph 1) Figure 2

Figure 3. Top: Extended structure of 4 showing a 2D layer. Bottom: Side view of 2D layer showing the pyridine ligands situated above and below the plane.

Figure 1b (polymorph 2)

88th CANADIAN CHEMISTRY CONFERENCE AND EXHIBITION Undergraduate Student Poster Competition Are you working on a research project and want to share your results? Do you have a paper to present at a Canadian Society for Chemistry Undergraduate Student Chemistry Conference and would like to present it again in poster format? Are you interested in presenting a poster for your Ă&#x17E;rst time? Here is an opportunity to show your peers and chemical professionals what you can do.


April 16, 2005 w w w. c s c 2 0 0 5 . c a



THE CANADIAN JOURNAL OF CHEMICAL ENGINEERING The Canadian Journal of Chemical Engineering (CJChE) publishes original research, new theoretical interpretations and critical reviews in the science or industrial practice of chemical and biochemical engineering or applied chemistry. The CJChE has an eighty-year successful history of producing high quality, cutting-edge research. It is peer-reviewed and has a prestigious list of international researchers. The CJChE is available in both hard copy and electronic versions.


Advertising in ACCN puts your message in front of 6,000

chemists, chemical engineers, and technologists every month at a very low cost. NEW FACILITIES FOR TEACHING AND GRADUATE RESEARCH

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View and pay your annual membership renewal notice on-line (Please note that this is only available if no changes are required on your renewal form. Should you need to make changes to your renewal, you will need to indicate them on a printed copy and mail or fax it in.)

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We want to help simplify your busy schedule with our on-line services, restricted to members only. Ensure your current e-mail address has been entered on your “Profile” page. To access on-line renewal and member services, click this link or type the URL in your browser. For the protection of your personal information, the on-line membership services are restricted to CIC members only, and you will be asked to logon your own personal secure account with a username and password. The “username” is composed of the first letter of your first name and the five (or less for short surnames) first letters of your surname. The middle name is not used (e.g. “John A. Dalton” would become: jdalto or “N. Stephen Bohr” would become: nbohr).

Canadian Society for Chemistry

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Feb 2005: ACCN, the Canadian Chemical News  

Canada’s leading magazine for the chemical sciences and engineering.

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