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September | septembre 2011

Canadian Chemical News | L’Actualité chimique canadienne A Magazine of the Chemical Institute of Canada and its Constituent Societies | Une magazine de l’institut de chimie du canada et ses sociétés constituantes

Methane

MAchine Harnessing the power of manure



The Tao of Tau Coal Cleans Up in Saskatchewan

www.accn.ca

Chemica


Table of Contents

Features

September | septembre Vol.63, No./No 8

Chemical Engineering

Chemistry

14

20

Coal Comes Clean

A billion-dollar retrofit will prevent ­carbon and sulphur from spewing into the atmosphere from SaskPower’s ­largest coal plant. By Tim Lougheed

Business

24

Glycobiology Guru

A class of biomolecules called glycans is finally beginning to give up its secrets. By Tyler Irving Pour obtenir la version française de cet article, écrivez-nous à magazine@accn.ca

Departments

Fuelling Clean Energy

Advances in biogas technology are making farm manure a valued resource for generating electricity. By Tyler Hamilton

5

From the Editor

7

Guest Column By Jan Kwak and John McIntosh

8

 hemical News C By Tyler Irving

29

Society News

30

Chemfusion By Joe Schwarcz

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FRom the editor

Executive Director

Roland Andersson, MCIC

ACTING EDITOR

Roberta Staley

G

as — such a small word for a state of matter that has had such a profound influence on scientific discovery. In this issue, we herald several new advances involving this ethereal substance. Science writer Tyler Hamilton, in his excellent feature “Fuelling Clean Energy,” looks at Ontario’s biogas sector, which is making advances in renewable energy thanks to a most-modest source — cow manure. Gas also permeates contributing editor Tim Lougheed’s story “Coal Comes Clean” about SaskPower’s ambitious project to divert one million tonnes of CO2 out of the atmosphere. With two-thirds of Saskatchewan’s electricity derived from coal, the province realized it had to devote considerable effort to cleaning up CO2 emissions. This initiative by SaskPower will net the province not only the green stamp of approval but a new multi-million dollar revenue stream. In the rest of ACCN, news editor Tyler Irving chats with Simon Fraser University’s David Vocadlo about the exciting potential that chemical glycobiology holds for afflictions like Alzheimer’s disease and diabetes. In “Chemical News,” ACCN offers up a cornucopia of cutting-edge ­scientific discoveries that include the superiority of lithium-sulphur batteries, a ­meteorite’s microscopic hitchhikers, the nurturing of stem cells and a facelift for the Canadian greenback. Finally, to our university readership: chemistry students, researchers and ­professors, welcome back to a new fall semester — hope this one’s, well, a gas.

Editor (on leave)

Jodi Di Menna

news editor

Tyler Irving, MCIC

contributing editor

Tim Lougheed

art direction & Graphic Design

Krista Leroux Kelly Turner

Society NEws

Bobbijo Sawchyn, MCIC Gale Thirlwall

Marketing Manager

Bernadette Dacey

Marketing Coordinator

Luke Andersson

Circulation

Michelle Moulton

Finance and Administration Director

Joan Kingston

Membership Services Coordinator

Angie Moulton

Editorial Board

Joe Schwarcz, MCIC, chair Milena Sejnoha, MCIC Bernard West, MCIC

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Subscription Rates Go to www.accn.ca to subscribe or to purchase single ­issues. The individual non-CIC member s­ ubscription price for 2011 is $100 CDN. The institutional subscription price for 2011 is $150 CDN. Single copies can be ­purchased for $10. ACCN (Canadian Chemical News/ L’Actualité chimique canadienne) is published 10 times a year by the ­Chemical Institute of Canada, www.cheminst.ca Recommended by the Chemical Institute of Canada (CIC), the Canadian Society for Chemistry (CSC), the Canadian Society for Chemical Engineering (CSChE), and the Canadian Society for Chemical Technology (CSCT). Views expressed do not necessarily represent the official position of the Institute or of the Societies that recommend the magazine.

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guest column

Women play key role in Middle Eastern chemistry programs

E

ver since its inception in the early 1980s, the guidelines of the Canadian Society for Chemistry (CSC) accreditation system for undergraduate chemistry programs have been based on three distinct objectives: to prepare graduates to practice their profession in a scientifically competent manner; to provide a broad basis for the recognition of ­acceptable degree programs; and to foster cooperation between educational institutions, industry and other employers of chemistry graduates. Some years ago, several universities in the Middle East were looking for ways to benchmark their educational programs against the standards of leading Western institutions. When the CSC was approached by Kuwait University in 2003, it was decided to use this as a first experiment in international outreach. After having prepared for a site visit in the same way as required from Canadian universities, the Kuwait University’s Department of Chemistry received a CSC site visit team in 2005. The visit resulted in a five-year, first-cycle CSC accreditation. Close connections between universities in the Arab Gulf quickly led to requests for site visits and subsequent full accreditation for the BSc chemistry programs of United Emirates University (UAE) in 2007, Qatar University and Bahrain University in 2009 and King Abdulaziz University (KAU) in Jeddah, Saudi Arabia in 2010, all for five-year, first-cycle accreditation. There are both similarities and differences between Canadian and Middle Eastern universities. While the chemistry programs in most cases are remarkably similar, there are key cultural differences. The Middle Eastern universities use mainly North American textbooks and instruction is in English. Modern instrumentation is widely available, often more so than at Canadian universities. What may have been the biggest surprise to site visit teams is the important role of women, who hold the positions of university presidents and vice-presidents, deans and department heads. There is also a high proportion of female students — 75 per cent at Qatar University, for example — and more than half the faculty is female. At Bahrain University and Kuwait University courses and labs are largely co-educational. However, UAE and Qatar University have duplicate labs and instrumentation in male and female buildings on separated campuses and even different libraries. Yet at the four Gulf universities male and female faculty and laboratory instructors

By Jan Kwak and John McIntosh

teach both genders. One can see a pattern of increased culturally acceptable integration slowly finding its way. The sharpest difference as observed by the site visit team is at KAU in Jeddah. Even though Jeddah, with its many international relations, is often considered the most liberal of Saudi cities by Western standards, at KAU male and female campuses are strictly separated and male faculty cannot teach female students (although at the graduate and research level there is limited mixing of the sexes). As a result, the Canadian site visit team for KAU had to have two male and two female members who compared notes to reach their conclusions about the two programs. Thus, while at the other Gulf universities there was no need to make any distinction between the male and female students and their courses and exams, it is hoped that the site visit report and its recommendations will lead to a strengthening of the role of female faculty at KAU. There are also significant administrative differences. Canadian departments are largely autonomous in deciding on programs and curriculum, but at the Middle Eastern universities we visited there is a strong ‘top-down’ administrative culture, leading to delays in program changes and heavy administrative procedures especially for ordering of supplies and equipment. While administrative accountability might be a burden on the department head, the much higher supplies and equipment budgets would make Canadian departments envious. In the past six years, the CSC accreditation committee has already made some adjustments to its process and guidelines for international accreditations. The process now requires a preliminary visit about a year before the site visit and a completely new assessment is required after five years. With the experience gained, the CSC can consider expanding its international role to other areas of the globe and it may decide to accept applications from universities where English is not the language of instruction. At the same time, our accreditation system provides significant international exposure for the CSC and it has certainly led to an increased mutual understanding and opportunities for collaboration. Jan Kwak, FCIC, is professor emeritus at Dalhousie ­ niversity and professor of physical chemistry and Head of the U ­Department of Chemistry and Earth Sciences at Qatar University. John  ­McIntosh, FCIC, is professor emeritus at the University of Windsor and Chair of the CSC Accreditation Committee.

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Chemical News Earth Chemistry

Asteroid nurtured ­life-giving chemicals

This fall, the Bank of Canada will begin rollout of its new polymer-based banknotes. The notes are made of a clear biaxially oriented polypropylene film with multiple layers of specialised coatings that contain added security features. They will be harder to counterfeit and are expected to last more than twice as long as the current, ­cotton-based variety.

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Michael Holly, Creative Services, University of Alberta / Bank of Canada

Amino acids, the building blocks of proteins, are easy enough to find on the surface of the earth - just look inside any organism. But a recent study from the University of Alberta provides evidence that these ­molecules can also form inside asteroids. In January 2000, a meteorite crashed through the atmosphere and into the ­frozen surface of Tagish Lake in the ­British ­Columbia Interior. Eventually, some of the fragments were acquired by a team ­headed by Chris Herd, associate professor in the ­Department of Earth and Atmospheric Sciences at U of A. The meteorite turned out to be unlike any other. Not only did it contain organic molecules like amino acids - rare but not ­unheard of - but the ­composition of the organic matter in its fragments was highly varied. The ­differences were so draA 10 centimetre-long fragment of the Tagish Lake meteorite contains evidence that matic it was as if the ­meteor was composed the organic ­molecules within it have been altered by the presence of liquid water. of parts from ­entirely ­different meteorites. “Our best ­explanation for this is that water percolating through the asteroid caused changes to the organic matter,” says Herd. The team was able to arrange four fragments in order from most altered to least altered. Surprisingly, the level of amino acids rose from the least altered to the second least altered fragment. That suggests that water inside the asteroid, formed either by impact or ­radioactive heating, provided the right environment to generate amino acids from precursor molecules like aldehydes and ketones. Although organic molecules can form in the void of interstellar space, the theory that asteroids provide a kind of nursery for them explains why some meteorites are chock full of amino acids. It may also explain how these molecules first arrived on Earth. “You can produce amino acids in hot water environments on the Earth,” says Herd, “but meteorites almost certainly provide an important component of ready-made amino acids that would have rained down at the right time.” That time was about 3.9 billion years ago, just before the first evidence of living organisms on Earth, he adds. The research was published in a June edition of Science.


Canada's top stories in the chemical sciences and engineering By Tyler Irving Pharmaceuticals

Post-traumatic stress sufferers get help For sufferers of post-traumatic stress ­disorder (PTSD), painful memories can be crippling. But research from the ­Université de Montréal shows that it may be possible to chemically influence the brain’s ability to recall the ­details of negative events, even after the memory is formed. Low levels of the hormone cortisol are known to have a negative impact on memory, but that effect was previously thought to be limited to their initial formation. “For a very long time, we thought that once a memory was stabilized in the brain, it was not possible to modify it once again,” says Marie-France

Marin, one of the study’s co-authors. “However, there was animal research at the beginning of 2000 that challenged that ­theory.” The team hypothesized that the drug metryapone, which prevents synthesis of cortisol, might have an effect on human memories even after they were formed. In the study, 33 test subjects were shown a slide show that told a story with both neutral and negative emotional elements. A few days later, they were divided into three groups, one of which received a placebo and the other two various doses of metryapone. When asked to recount the story, those treated

with the drug showed less recall of the story’s negative elements. This effect was still noticeable days later, after the effect of metryapone had worn off. Marin cautions that more work needs to be done before the effect can be ­developed into a therapeutic. “We still need to establish whether the same ­effects could be attained with personal, ­autobiographical memory. Then we could move with a clinical population to see whether we could apply the same paradigm to post-traumatic stress disorder victims.” The work is published in the Journal of Clinical ­Endocrinology & Metabolism.

Jerôme Waldispuhl

Biochemistry

Researcher develops faster software for folding proteins The process of folding a linear polypeptide into a complete ­protein with a specialized shape and function is one of nature’s miracles. Computers can model this process using molecular ­dynamics (MD) but it’s still an enormous task - determining the folding pathway for a single protein can take thousands of hours of processing time. Now a researcher at McGill University has ­developed a program that could greatly speed up this process. Jerôme Waldispuhl is an assistant professor in the Department of Computer Science at McGill and has been working in the field of bioinformatics for more than a decade. He’s developed a program called tFolder, which is able to give a rough estimate of the structure for a particular protein in about half an hour. While traditional MD techniques use classical physics laws to compute a sequence of 3D structures, detailing each possible step along the folding pathway, tFolder takes a ‘birds-eye view’ approach. The program uses a coarse-grained energy landscape model that treats each amino acid as a discrete unit, which enables it to quickly enumerate all possible structures and calculate which ones are most likely. “It doesn’t aim to substitute for molecular

tFolder looks at a peptide sequence and enumerates all ­possible ­positions for structures known as beta sheets, which are  represented by ­coloured arrows. The color gradient indicates the sequence ­position: yellow arrows are toward the beginning of the sequence, followed by green, blue and purple. The most likely structure is the largest one displayed. dynamics, it’s a completely different approach,” says ­Waldispuhl. “The idea is to sacrifice some precision but, on the other hand, we have a huge gain in terms of calculability.” Waldispuhl has already tested the model on a polypeptide called protein G, one of the few proteins for which ­information about the folding pathway is available. He hopes that in the future it could be used to narrow down the list of ­possible structures for other folding simulations, saving thousands of hours in processing time. The research is published in the ­Journal of Computational Biology and the software is at http://csb.cs.mcgill.ca/tfolder/.

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Chemical News Materials Science

Buzz about new ­batteries

Although still in the experimental stages, lithium-sulphur (Li-S) ­batteries could offer three to five times more energy density than lithium-ion, the current industry standard for ­personal electronics and electric vehicles. Now, a discovery at the ­University of ­Waterloo has brought Li-S batteries one step closer to ­commercial viability. Li-S batteries depend on a reversible reaction that converts elemental lithium and sulphur to Li2S. The problem is that the reaction has a number of intermediate species — a series of ­polysulphide ions — which are soluble in the electrolyte. If these species dissolve and are lost from the positive electrode, they can no longer do useful work, reducing the capacity of the battery.

In 2009, Linda Nazar and her team at the University of Waterloo came partway toward a solution by ­embedding the sulphur in a polymer-coated mesoporous conductive ­carbon matrix. This material creates an environment that delivers the electrons ­required for the electrochemical ­reaction, but also holds in most of the ­soluble ­polysulphides. Now, Nazar’s team has gone one step further by adding silica particles with a very high surface area and pore volume into the same ­carbon matrix. The silica particles have a weak affinity for the ­soluble ­polysulphides, which ­physically absorb within their pores ­instead of leaving the matrix. ­Although the ­polysulphides can’t ­undergo ­further ­electrochemical ­reaction within the silica, the weak binding means that they are gradually released later in the charge cycle to form ­insoluble Li2S and complete the reaction. Importantly, this ­process is reversible. The ability to hold the polysulphides in silica particles allows the carbon matrix itself to have larger pores. This increases the rate of discharge­up to 10-fold while maintaining energy ­density. “We’re hanging on to 82 per cent of the polysulphides over 30 ­cycles, but you can tune the pore size and the surface area of this additive to really improve upon that process,” says Nazar. The work was published this past May in ­Nature Communications.

Biotechnology

microfluidic ­device nurtures stem cells

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cells in parallel while monitoring their growth in real time using automated microscopy. This level of detail makes it ­possible to look for the tiny changes in growth cycles that can distinguish ­sub-­populations of HSCs. As a proof of the concept, HSCs in the ­device were exposed to a reduced concentration of a certain growth factor (steel factor, or SF) for various periods to see how long they could survive under these conditions before being rescued. The crucial time turned out to be between 16 and 24 hours, when the cells exit from a quiescent state to enter cell cycle. “This is an example of an experiment that just could not have been done otherwise; we could not have answered this question with the current techniques,” says ­Veronique Lecault, lead author of the study and

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Veronique Lecault

Hematopoietic stem cells (HSCs) have the unique ability to give rise to all possible types of blood cells. Despite this, they are hard to distinguish from other cells of the bone marrow, which makes studying them in v­itro an enormous challenge. This could soon change thanks to a new microfluidic device developed at the University of British Columbia. The device is made of ­transparent polydimethylsiloxane (PDMS) and could comfortably fit inside a matchbox. Inside, there are ­hundreds of parallel channels studded with thousands of chambers, each about four nanolitres in size. The chambers are ­surrounded by an iso-osmotic bath which prevents dehydration and keeps finicky HSCs in their ideal growth conditions. The unique setup allows researchers to grow hundreds of bone marrow

False colour image of the microfluidic array showing the arrangement of channels and chambers. The matchbox-sized device contains 1600 chambers. Each chamber is 160 µm along each side. a graduate student in the Department of Chemical and Biological ­Engineering at UBC. The technique could be applied in any situation where heterogeneous cell populations need to be examined, which includes fields like cancer research and drug ­development. The work is published in the July issue of Nature Methods.


Canada's top stories in the chemical sciences and engineering By Tyler Irving Policy and Law

Standoff in Pesticide c ­ hallenge Both sides are claiming victory in a settlement regarding ­Quebec’s ban on the cosmetic use of pesticides containing the chemical 2,4-­Dichlorophenoxyacetic acid (2,4-D). 2,4-D is one of the world’s most widely used pesticides, but debate over its possible carcinogenicity continues. In 2006 it was banned for cosmetic use in Quebec. In 2008, a review by Canada’s Pest Management Regulatory Agency (PMRA) concluded that products containing 2,4-D “do not pose an unacceptable risk to human health or the environment, provided that the instructions on their label are followed.” In 2009, Dow AgroSciences, which makes 2,4-D, ­challenged Quebec’s ban under the North American Free Trade Agreement (NAFTA), seeking $2 million in damages. This past May, Dow agreed to withdraw the challenge with no compensation, provided that the Quebec government ­acknowledge and agree with the

conclusion of the PMRA. The ban, however, will remain in place. In a media release, Jim Wispinski, president and CEO of Dow AgroSciences Canada, characterized the settlement as positive, saying that “Quebec has agreed with the federal government’s findings as to the safety of our product when used correctly.” However, Theresa McClenaghan, executive director of the Canadian Environmental Law Association says that the challenge was never about the damages. “Most of us felt at the time that bringing the challenge under Chapter 11 of NAFTA was a rhetorical and advocacy device by Dow,” ­McClenaghan says. “The associations representing the producers did a pretty thorough round of litigation twice and the Supreme Court has already ruled definitively on it.” McClenaghan notes that the settlement says nothing about the use of pesticides in agriculture and ­forestry - markets many times larger than that for cosmetic use.

Climate Change

More trees won’t solve ­climate change It seems logical enough: if deforestation raises CO2 emissions, then afforestation — planting more trees — should be an effective way of combating climate change. But a new Canadian climate model shows that while this is true, the effect is smaller than you might expect. Previous climate models have been somewhat unrealistic when it comes to afforestation, says Alvaro Montenegro of St. Francis Xavier University, one of the co-authors of the study, which is based on a computer simulation called the Canadian Earth System Model (CanESM1). Unlike previous models, CanESM1 accounted for the dynamics of forest growth, a slow process that can take decades. It also accounted for the fact that in areas like the Prairies, low rainfall precludes forest growth, even if agriculture were to cease. Finally, while forests do reduce atmospheric carbon, they are also darker than most cropland. This means that they absorb more sunlight and thus generate more heat than open fields. According to the model, global average temperatures will have increased between 1850 and 2100 by about 3 C. Replacing 100 per cent of the world’s cropland with forest — an unrealistic scenario — would only reduce this by 0.45 C. Montenegro cautions that this is only one study, but says that the results point to the importance of decreasing emissions, rather than trying to compensate for them. “What the paper says is that if we continue to emit the way we are, planting trees, even over a very large fraction of our present day crop land, will do very little to reduce global temperature.” The study is published in the June issue of Nature Geoscience.

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SaskPower is backing a new, billion-dollar carbon and sulphur ­sequestration initiative that will - almost - turn coal into clean energy. By Tim Lougheed

ong before most of us were worried about climate change, various industries had developed an interest in capturing carbon dioxide. The gas would prove invaluable to such venerable 19th-century innovations as bubbly soft drinks or fire extinguishers that starve flames of oxygen. By the end of the 20th century, the oil and gas industry had nurtured its own appetite for CO2, which can be injected into mature wells to extract more of their contents. The latest priority is simply preventing the gas from making its way into the atmosphere, thereby eliminating its contribution to the greenhouse effect that is blamed for altering the world’s climatic patterns. Major sources like industrial smokestacks are therefore being targeted for the collection of CO2, which is then put into a form of storage known as sequestration. The fundamental process of extracting this material from flue gases has been in place for decades, along with reliable technology that can be scaled up to meet this new environmental challenge. Now a project in Saskatchewan is tackling that challenge in an even more ambitious way. About one million tonnes of CO2 will be diverted annually from SaskPower’s coal-fired Boundary Dam generating station in the southern end of the province, near Estevan. It will take $1.24 billion to outfit the plant over the next few years, an outlay that the provincial government approved last April.

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Dubbed the Boundary Dam Integrated Carbon Capture and Sequestration Demonstration Project, it is one of the largest construction ventures Saskatchewan has ever seen. SaskPower has a lot riding on it, since almost two-thirds of the province’s electricity comes from coal, which is burned in plants that are more than 40 years old. “We had to answer the question for ourselves: can we rely on coal as a fuel source for electrical generation?” says Mike Monea, the project’s vice-president. “We felt that if we could clean up the emissions, then we knew that we could keep coal.” Monea points out that this option was compared directly with the prospect of converting generating stations to run on natural gas. Efficient carbon capture allows coal to compete with that alternative, especially if the costs of this process can be recovered by selling the CO2 to oil well operators. “We have 300 years of coal here, at a very low cost,” he says. “We now have a fuel supply that we can predict for 30 years, which we can’t do for natural gas.” In fact, the redesigned plant will run much more cleanly than it could on natural gas. All of its sulphur dioxide (SO2) emissions and 90 per cent of its carbon dioxide emissions will be recovered and sold, thanks to a system developed by Montreal-based Cansolv Technologies Inc. That firm was founded in 1997 to commercialize SO2-scrubbing technology originally acquired from Union Carbide. Cansolv’s R&D activities subsequently expanded its capabilities to


Chemical Engineering | co 2 capture use in more benign environments. PTRC regularly hosts delegations from Europe or Asia, who are curious about how well a carbon capture strategy copes with Saskatchewan’s extreme climate. Wilson anticipates even more of these visits as the Boundary Dam project proceeds. According to the Paris-based International Energy Agency (IEA), power generation represents the single greatest energy-related human contribution to CO2 in the earth’s atmosphere. In 1990, it made up 36 per cent of the total, jumping to 41  per  cent by 2007. By 2030, IEA predicts this will rise to 44 per cent, as well as accounting for more than half of the increase in overall CO2 emissions. As in Saskatchewan, a majority of that increase will come from coal. China is expected to be another place where coal will continue to play this dominant role. Cansolv has already been testing its SO2-scrubbing technology on commercially operating facilities all over that country. SaskPower’s Mike Monea says that track record made the company an attractive contender for the Boundary Dam project. “They’re one of the few companies that could demonstrate the efficiencies of their process,”

Petroleum Technology Research Centre Regina / SaskPower

CO2-scrubbing and in 2008 the company became a subsidiary of Shell Global Solutions International. Cansolv’s system employs the organic compounds known as amines, consisting of ammonia derivatives in which hydrogen has been replaced by some member of a hydrocarbon group. In this case, a unique class of diamine absorbents capture and regenerate SO2 and CO2. More specifically, gas going up the power plant’s chimney will be cooled and diverted to an absorber tower, where it will interact with the amine, which collects the pollutants. The amine stream is subsequently re-heated and its contents returned to a gaseous phase, so it can be dehydrated and compressed for storage. According to Malcolm Wilson, CEO of the Petroleum Technology Research Centre (PTRC) in Regina, the approach is reliable and proven. “Right now, if you are going to want to be successful in developing a capture project, amines are the only way to go,” says Wilson, who notes that these agents have long since demonstrated their effectiveness in cleaning up flue gases. What remains to be seen is the level of efficiency that can ultimately be obtained. “We know the technology will work,” he adds. “We just don’t know how well it will work.” Wilson is referring to the fact that the Cansolv hardware [LEFT] CO2 ­purchased will be driven by the Boundary Dam station itself, creating a from ­Dakota parasitic power loss. The amount could be considerable, with ­Gasification ­completes a joursome estimates suggesting that this 150 MW plant might ney of more than 300 kilometres to only yield a net load of 110-115 MW once the clean-up arrive at the end equipment is running. However, this drop could be miniof this pipeline in ­Weyburn, where mized by modifying and improving the design, says Wilson. it will help oil The exact placement of heat exchangers, for instance, could companies restore production on turn out to offer great gains. Such tweaking can be planned ­depleted wells. in advance, through simulations or pilot plants, but the [RIGHT] actual impact can only be assessed by trying it out in a full­SaskPower’s ­coal-fired scale installation, Wilson adds. ­Boundary Dam SaskPower will also be gauging the influence of weather, which Power Station, located in southern on the prairies can go from -40 C to 40 C over the course of a ­Saskatchewan near year. The region is thus a perfect place to try out equipment for Estevan.

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the environmental impact of their power generating systems without sacrificing access to the country’s rich coal resources. “All eyes are going to stay on Saskatchewan,” says Wilson. The interior of Unit 3 of SaskPower’s Boundary Dam Power Station, site of the utility’s Integrated Carbon Capture and Sequestration Demonstration Project.

A new ­rationale for carbon capture The market for CO2 is more than a century old, but the business model associated with the gas has evolved rapidly in recent years. When it was being used primarily for beverage carbonation, food preservation or refrigeration, the emphasis was on creating a highly purified product that would meet government inspection agency standards. Cost was a secondary consideration, as was the need for mass quantities. Today’s carbon capture regime is much more of a numbers game. Buyers now want lots of the stuff and at the cheapest possible price. “The paradigm shift here is that we’re less worried about the quality and more worried about the cost,” says Malcolm Wilson, CEO of the Petroleum Technology Research Centre (PTRC), based in Regina. “We’re now engineering to maximize energy efficiency and minimize the cost of the product,” Wilson says. He has helped turn this paradigm into a practical reality. The PTRC, a not-for-profit research and development agency that was ­established in 1998, belongs to a group of organizations that is currently wrapping up 11 years’ worth of work on a major effort that has used CO2 to breathe new life into some 250 sq. kilometres of depleted oil fields. Since 2000, this $85 million international project has studied the sequestration of CO2 received from a large coal ­gasification plant in North Dakota. That CO2 is piped 320 kilometres to the ­Weyburn-Midale region of southeastern Saskatchewan and injected into two depleted oil fields. For the American firm, Dakota Gasification, the initiative has been nothing less than a life saver. By investing in the necessary infrastructure to capture CO2 that would otherwise have gone up a chimney, the company created an entirely new revenue stream worth tens of millions of dollars annually. That cash helped Dakota withstand major drops in the price of natural gas that were threatening to put it out of business. Near the beginning of 2011, managers proudly marked delivery of the 20 millionth metric ton of CO2 through the pipeline.

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SaskPower

he says, adding that the deal was further sweetened by the ­expertise of SNC Lavalin to carry out the ­installation. “Combining Cansolv with SNC Lavalin made for a tight package, which also went along with well defined costs.” Monea insists that the move to retain coal-fired generation does not exclude the possibility of other sources of energy, including renewable options such as windmills. However, just as a Boundary Dam station model based on coal won out over a model based on natural gas, these alternatives will have to stand on their own merits. “The real message is that we need all forms of fuel for generating power,” he says. “Coal will be an option for us, and we’ll show through good engineering that we can have a business case that is positive.” People at the receiving end of the pipeline were just as pleased. By 2005, CO2-primed oil wells around Weyburn had returned to ­production levels that had not been seen since the 1970s, just in time for a spike in the price of this commodity. Above all, the outcome bolsters the business case for an undertaking that might be a tough sell: preventing CO2 today from contributing to changes in climate that may not occur for a century or more. The results also bolstered the case SaskPower could make for its own massive investment in infrastructure to capture both CO2 and SO2 at its Boundary Dam generating station. The scope of this project should set the standard for utilities around the world, especially in places like China, which are highly motivated to reduce


 Continuing

Education for Chemical Professionals

Laboratory Safety course September 19–20, 2011 Vancouver, BC October 24–25, 2011 London, ON

For → Chemists and chemical technologists whose responsibilities include managing, conducting safety audits or improving the operational safety of chemical laboratories, chemical plants and research facilities.

Registration Fees* CIC Members $550 Non-members $750 Student Members $150

*includes Laboratory Health and Safety Guidelines 4th ed.

For more information, visit www.cheminst.ca/profdev


 Canadian Society for Chemistry (CSC)

95th Canadian Chemistry Conference and Exhibition May 26–30, 2012 Calgary, alberta, Telus Convention Centre

Energizing Chemistry

The Three Sisters Mountains Alberta, Canada

www.csc2012.ca


Chemical Institute of Canada

The Catalysis Award Call for Nominations

The Catalysis Award, sponsored by the Canadian Catalysis ­Foundation, is ­awarded biannually to an individual who, while resident in Canada, has made a ­distinguished contribution to the field of catalysis. The recipient of the Award ­receives a ­rhodiumplated silver medal and travel expenses to ­present the Award Lecture at the ­Canadian Symposium on Catalysis or the annual ­conference of the Canadian ­Society for Chemistry or the Canadian Society for Chemical Engineering. Nominations for the 2012 Award must be submitted in writing to the Awards ­Manager by October 3, 2011, using the CIC n ­ omination form found at w ­ ww.cheminst.ca/awards. Previous winners of the Catalysis Award are R.J. Cvetanovic and Y. Amenomiya (1977), R.B. Anderson (1979), C.H. ­Amberg (1982), H. Alper (1984), H.W. ­Habgood (1986), J.B. Moffat (1988), B.R. James (1990), B. Wojciechowski (1992), I. Dalla Lana (1994), M. Ternan (1996), S. Kaliaguine (1998), G.L. Rempel (2000), M.C. Baird (2002), C.A. Fyfe (2004), S. Brown (2006), Flora T.T. Ng (2008) and R.­Stanley Brown (2010). For more information, please contact: Division Vice-Chair, ­William Epling ­Department of Chemical Engineering University of Waterloo Waterloo, ON N2L 3G1; Tel: (519) 888-4567, ext. 37048, Fax: (519) 888-4347, E-mail: wepling@uwaterloo.ca or Gale Thirlwall, Awards Manager Chemical Institute of C ­ anada 130 Slater Street, Suite 550 Ottawa, ON K1P 6E2 Tel: (613) 232-6252, ext 223; Fax: (613) 232-5862, E-mail: gthirlwall@cheminst.ca.

CIC


QA Glycobiology Guru &

David Vocadlo’s insights into glycans may lead to therapeutics for c­ancer and Alzheimer’s disease.

By Tyler Irving

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hile the study of DNA and proteins has become almost routine, another important class of biomolecules — glycans — is just beginning to give up its secrets. David Vocadlo of Simon Fraser University in Burnaby, British Columbia is a researcher at the frontiers of chemical glycobiology. ACCN spoke to Vocadlo to find out how the study of glycans is changing our view of biochemical processes and why they may be key to treating diseases like diabetes, Alzheimer’s and cancer.

ACCN What is a glycan? DV Glycans are one of the key classes of biological molecules.

You have nucleic acids like DNA and RNA, proteins, lipids and carbohydrates, which are also called glycans. The other biomolecules are quite heavily studied, but glycans are more difficult to study for a number of different reasons, so the field hasn’t advanced as far. Simply put, glycans are an assembly of different sugar units that form very specific structures. When someone ingests some sugar such as glucose, it gets converted within cells into other types of sugar building blocks. In humans there are essentially 10 different types of sugar units that are used to build up glycans. Glucose is just one of them, there are others such as mannose and galactose. In principle, the diversity of different structures is tremendous, there was recently a paper conservatively estimating that mammals have 7,000 different types of glycans. ACCN How do you study them? DV Our laboratory is mostly interested in chemical glyco-

biology. We study enzymes and other proteins that interact with carbohydrates and then develop chemical tools with which we can study those biological processes as well as the enzymes themselves. Ideally, we use these tools to look at them in cells or even in vivo to try to discern what their function is. It’s exciting because it’s a frontier area; there’s a lot

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to discover in the field of glycobiology. And it’s turning out that these glycans are very important in a number of different diverse biological processes. ACCN Can you give some examples? DV Every animal cell has a carbohydrate coating around it,

known as the glycocalyx. The glycocalyx extends out from the cell surface and is the first line of contact between the cell and other cells or, alternatively, viruses or bacteria. It’s what the other cells see and they use it to communicate with each other. Some beautiful work has shown how some glycans on the cell surface are essential for organisms to develop in an appropriate way. An older example that people can relate to is the ABO blood group antigens, which are glycans. The differences between them are simply the presence or absence of different sugar units within the glycan structure. For example, the O-type glycan has one less sugar unit than the A-type or the B-type. These blood group antigens are interesting: we know that they exist and we know that they’re important for transfusion, but it’s not known what their precise biological functions actually are or why there are different types. We speculate that this diversity has been important historically to make sure that populations are resistant to epidemics. Blood group antigens have a long history in Canada; Ray Lemieux, of the University of Alberta, was the first to synthesize them chemically, a fantastic feat at the time. ACCN Much of your work revolves around the O-GlcNAc post-translational modification. What is this? DV Proteins can be modified in many ways: they can be

phosphorylated, acetylated, methylated and of course glycosylated. O-GlcNAc is a form of glycosylation, a modification of proteins found inside the cell. It’s just a single saccharide unit, O-linked N-acetylglucosamine (O-GlcNAc)


Chemistry | Glycoscience

OGT OGA

simon fraser university

In the body, proteins (represented in red) are converted between their native form (left) and glycosylated form (right). The enzyme OGT adds the glycan O-GlcNAc (in black) onto the protein while the enzyme OGA removes it. David Vocadlo’s team has developed robust inhibitors of both OGA and OGT to probe the role of this modification in such biological processes as diabetes, cancer and ­Alzheimer’s disease.

that gets added on to proteins. There are two enzymes involved: one called O-GlcNAc transferase (OGT) that puts O-GlcNAc on the proteins and one that removes it, called O-GlcNAcase (OGA). We started off trying to understand how these enzymes (OGA and OGT) work at a mechanistic level and how they catalyze the reactions that they do. We then developed inhibitors that would target them in a specific way. We’ve developed very good inhibitors of both of them, so we’re now using those to understand what some of the biological roles of the O-GlcNAc modification are. The modification is interesting since it’s been implicated in both diabetes and Alzheimer’s disease. ACCN How so? DV It’s an elegant hypothesis. When glucose is taken up by

cells, a certain percentage of it is shunted into a biosynthetic pathway, the end result of which is the substrate for OGT. OGT takes that substrate, adds it on to proteins and the net result is increased O-GlcNAc levels. The second theory is that O-GlcNAc glycosylation and phosphorylation of proteins are sometimes reciprocal. This is important because insulin signaling depends on phorphorylation pathways. When you take those two ideas together, what you can see is that with increased blood glucose levels — one of the symptoms of diabetes — proteins within cells are going to have increased O-GlcNAc levels. If O-GlcNAc levels on proteins go up, they might compete with and impair phosphorylation and that might attenuate insulin signaling. It becomes a vicious cycle where increased blood glucose has toxic effects and impairs insulin signaling, which results in even higher blood glucose and more damage. So we started to develop selective compounds that would target OGA, the enzyme

that removes the sugar, in order to determine the involvement of O-GlcNAc in insulin resistance. What we found out by doing this was that you could increase O-GlcNAc levels dramatically, but it didn’t actually result in insulin resistance. ACCN Were you surprised that the results didn’t fit with the hypothesis? DV For us it was a very surprising observation. But that is the

nature of science and what makes it continually ­interesting to me — there are always surprises. In any case, the ­experiments we did suggest that the current proposal is not as simple as thought and offer some new approaches and ideas as to how the model might be refined. I think in the end our findings turned out to be quite important for other reasons as well. They show you can inhibit the enzyme and not cause serious problems like insulin resistance. Actually, that is what prompted us to consider looking at Alzheimer’s disease and the potential benefit of increasing O-GlcNAc levels; you obviously don’t want to cause insulin resistance while trying to improve Alzheimer’s.

september 2011 CAnadian Chemical News   21


ACCN How does Alzheimer’s come into it? DV One of the hallmarks of Alzheimer’s are these

neurofibrillary tangles in the brain, which contain a hyperphosphorylated form of a protein called Tau. A lot of people are interested in blocking the aggregation of Tau and its toxicity by blocking its phosphorylation. In addition to that, it’s known that in Alzheimer’s disease, one of the early symptoms is an inability of neurons to appropriately use glucose. So the idea there is that if you get decreased levels of O-GlcNAc within cells, this might enable hyperphosphorylation of Tau, which leads to its aggregation and downstream toxicity. We published a paper on using our inhibitors to block OGA, the enzyme that removes O-GlcNAc. It showed that if you increase O-GlcNAc levels dramatically with this inhibitor, you see decreases in phosphorylation of Tau at certain specific sites that are pathologically relevant. ACCN Are there other diseases where O-Glc-NAc is thought to play a role? DV Recently there have been a few papers published

i­ mplicating O-GlcNAc in cancer and there’s some fairly good data supporting that idea. The theory in that particular case is that somehow O-GlcNAc is involved in the ability of cancer cells to survive and proliferate. If you can decrease levels of O-GlcNAc in cells, you may be able to prevent the ­progression of cancer. That’s one of the really nice things about inhibitors — you can quickly deploy them in different experimental models. ACCN Tell us about your company, Alectos ­Therapeutics, formed in 2007 to commercialize these discoveries. DV A lot of the large pharmaceutical companies are very

interested in Alzheimer’s disease because there’s no therapeutic right now that will block its progression. Alectos Therapeutics contacted Merck about the possibility of establishing a research-collaboration and licensing agreement and they were very interested in the target as well as the technology. So Alectos is focusing on developing inhibitors of OGA for Alzheimer’s disease. The ones we have are a starting point; although they’re quite good in terms of specificity, there are always things that may need to be tweaked to generate compounds that have the most desirable properties in the body. Right now we’re looking at a number of different issues that have to be addressed for the program to progress.

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ACCN Why is it so much harder to study glycans than DNA or proteins? DV It’s been difficult to dissect the critical functions of glycans in biology because, in many cases, if you just knock out an enzyme that’s involved in building up a glycan, you can have developmental effects in the organism that you’re studying. It’s not comparable to changing the levels of glycans in an adult organism. Also, knocking out an enzyme is not the same thing as the enzyme being inhibited; if you knock out the enzyme the protein is gone and that can complicate issues. That’s why we’ve gone with an inhibitor-based approach. Another factor is that glycans are difficult to synthesize. If you want to synthesize a nucleic acid, you can use a nucleic acid synthesizer — you can just call up a company and get it delivered. For glycans that’s very difficult; it’s a tremendously laborious process. You have to use traditional chemical synthesis. It’s a really time-consuming process and there are people who specialize only in synthesizing different glycans. To make a glycan with just six units can take from six months to one year. ACCN Have there been any major advances in the past few years? DV There’s been some really tremendous efforts directed at

solid-phase synthesis of carbohydrates and there are a number of groups around the world that are working on that. Basically you use polymer beads as an anchor, just like with peptide synthesis and then you add to the glycan chain while it’s on the beads and cleave it off at the end. It’s not in the mainstream yet but there are now carbohydrate synthesizers that have been developed and they’re being prototype tested. Researchers have also been advancing the use of enzymes to rapidly build glycans and this has shown a lot of promise as well. ACCN What excites you about glycobiology? DV When you teach science, often you’re teaching people

about what is known, but the most exciting part of science is what’s not known. In the field of glycobiology and ­g lycoscience, there’s a tremendous amount that is not known and that’s the stuff that is really exciting. It’s pushing that limit of what we know, seeing what lies just over there. What will this study show about the role glycans are playing in biology? Can we manipulate this system for potentially therapeutic benefit? I think those are some of the really interesting questions in the field.


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Chemical Institute of Canada

Join the International Year of Chemistry Celebrations! This is a year long opportunity to educate the public on the wonders of chemistry. See planned activities and get involved now at www.iyc2011.ca

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fuelling clean energy

Water purification pioneer Andrew Benedek is leading a biogas ­revolution in Ontario. By Tyler Hamilton

T

rying to produce clean water from sewage? Then microorganisms are your enemy. Trying to produce clean energy instead? Then these disease-causing critters can be your closest ally. Andrew Benedek has made microorganisms his ally in a clean-energy venture that recently chose Ontario as the home of its future global headquarters, set to open in 2013. The company, Anaergia, specializes in the design and manufacture of biogas systems that rely on microorganisms to convert organic waste, such as sewage and animal manure, into renewable fuel. The process, called anaerobic digestion, is widely accepted in Europe but has been slow to catch on in North America. Benedek plans to change that. Six years ago, the 68-year-old Canadian water purification pioneer, who now lives in California, would have considered these microscopic bugs his enemy. Benedek spent most of his career trying to eliminate harmful microbes from the water

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that gets flushed down our toilets or ejected from industrial processes. As CEO of ZENON Environmental, the water innovation company he founded in 1980 in Oakville, Ont., Benedek developed a cost-effective membrane technology for wastewater facilities that could filter out the smallest and nastiest of microorganisms, from bacteria such as E. coli to pathogens such as Cryptosporidium. It worked so well that General Electric acquired ZENON in a 2006 deal valued at $760 million, making Benedek a rich man (he owned nearly 20 per cent of the company’s shares) and giving the former McMaster University chemistry professor a chance to re-enter academia after a 26-year hiatus. Indeed, within no time he became a semi-retired research associate at the Scripps Institute of Oceanography, a department within the University of California, San Diego. It was at the Scripps Institute that Benedek began seeing the microorganisms found in sewage in a different, more beneficial


Business | BioGas

light. Water purification was his lifelong passion, but increasingly he was concerned about climate change, energy security and the importance of weaning the world from fossil fuels. “I looked at the different ways I could do something about the energy problem, and in the end it came down to the fact that I understood anaerobic digestion,” Benedek says. Anaerobic digestion (AD) is a multi-staged process through which certain microbes break down organic matter in an oxygen-free environment. It can happen slowly and naturally, such as in a municipal landfill, or it can be dramatically accelerated in a special tank called a digester. “It’s basically a giant stomach being optimized to flatulate 24-seven,” said Dan Jones, a principal with biogas systems supplier European Power System in Mississauga, Ont. There are typically four stages. The process begins with hydrolytic bacteria, which secrete the enzymes necessary to break down complex organic molecules into soluble organic compounds like simple sugars, fatty acids and amino acids. Acidogenic bugs take over next, converting the soluble compounds into volatile fatty acids and alcohol, which acetogenic bacteria then turn into acetic acid, CO2 and hydrogen. Running the last leg of the race are the methanogens, which make methane out of acetic acid and hydrogen. To make sure there’s a healthy balance of the right microbes, manure is often mixed with oils — old restaurant grease works fine — and some kind of substrate, such as crop residue. “You have thousands of species in there, but as long as you consistently create the right conditions the species will sort themselves out,” said Chris Ferguson, managing director of biogas systems developer CCS-agriKomp, which is in the process of building its first facility in Millbrook, Ont. The end result is the production of a methane-rich biogas, which can be burned for its heat or to generate electricity. The renewable biogas can also be cleaned and upgraded for injection into natural gas pipelines. Upgrading is necessary because biogas has high levels of hydrogen sulphide and other contaminants compared to pipeline-quality gas. It also contains about 40 per cent less methane than natural gas, so methane content must be concentrated to similar levels. AD is an old idea that emerged in the late 1800s. The first patent for such a system was issued in 1907 in Germany, which along with France used the bacterial-driven process to treat manure during the Second World War. Facilities are

now deployed widely throughout Europe, but the hotbed for development remains Germany, where systems are used on more than 4,000 farms to produce biogas. Larger “district” systems that process high-volume organic waste streams from industry and municipalities are also plentiful. The technology, however, has gained relatively little traction in North America. In Ontario only about a dozen on-farm anaerobic digestion systems were operational by the end of 2010, representing 65 per cent of all installed systems across Canada. In the United States there are only 162 operational systems, according to the Environmental Protection Agency. It estimates that dairy and swine farms alone could justify deployment of more than 8,000 systems, which collectively could produce enough electricity each year for 1.3 million homes. Jennifer Green, executive coordinator of the Agri-Energy Producers Association of Ontario, says that the renewable energy that can be harnessed from AD systems is, in many ways, just the icing on the cake. For farmers, it’s an effective approach to waste management that mitigates odour (versus manure spread on an open field) and neutralizes pathogens that could contaminate ground water. The process also produces a safe, nutrient-rich “digestate” that can be used as a fertilizer for crops. For municipalities and industry, it’s a way to divert the amount of organic waste that goes to landfills, where the material would naturally decompose and slowly emit methane — a highly potent greenhouse gas — into the atmosphere. Green says the quality of energy AD systems produce is also superior. The biogas can be stored anytime and burned on demand to generate electricity, making it a more reliable source of power than wind or solar. “It’s an opportunity completely untapped,” Green says. That was Benedek’s thinking. He saw no clear technology leader in North America’s fledgling biogas market and felt it was time to create one, though without having to reinvent the wheel. “I decided I would invest in a European company and then bring the technology to North America, while also bringing improvements to the field,” he says. Within a year of selling ZENON Benedek travelled to Germany to research the technology landscape. One company that caught his eye was UTS Biogastechnik (formerly UTS Umwelt-Technik-Süd), which had supplied

september 2011 CAnadian Chemical News   25


[TOP]

­Andrew Benedek has allied with microorganisms to produce clean energy. [RIGHT]

Aron Hamm, biodigester manager at ­Ontario’s Delft Blue, ­explains that the manure from 2,700 veal calves undergoes a ­biochemical ­process that triggers ­biogas ­production, used to produce ­electricity to run the farm.

equipment to more than 1,500 biogas plants worldwide. Benedek saw huge growth potential in the company and in 2007 acquired majority control. Two years later, he cracked the U.S. market with the opening of a subsidiary, UTS BioEnergy, in Encinitas, Calif., and soon established a ­presence in Michigan and Idaho. Canada was next. Benedek discovered the UTS brand had already been trademarked by a publicly traded oil company in Calgary, so he devised the name Anaergia — a mix of “anaerobic” and “energy” — and announced plans this past May to establish the company’s global headquarters in Southern Ontario. It was a coup for the province, which agreed to contribute $16 million (half grant, half zero-interest loan) toward the $70 million project. The headquarters is expected

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to include R&D capacity, equipment manufacturing and create more than 200 jobs. Why pick Ontario? It helped that the government was willing to contribute 23 per cent of the new facility’s start-up costs, but Benedek also appreciated the province’s long-term support for renewable energy. It has progressive legislation such as the Green Energy and Green Economy Act 2009, and progressive energy policy, such as a comprehensive feed-in-tariff (FIT) program that was modelled after similar programs in Europe. The FIT program pays developers of green energy projects a generous rate for the power they produce over a period of 20 years. Developers that choose to produce biogas and then burn it to generate electricity, for example, can earn anywhere


Ross Blaine

from 10.4 cents per kilowatt-hour for the largest projects up to 19.5 cents per kilowatt-hour for the smallest. (For comparison, Ontarians pay between 5.9 cents to 10.7 cents per ­kilowatt-hour for the electricity they consume, depending on the time of day). The program is supposed to reduce risk and create stability in the market. Projects become more economical because of the premium paid for the electricity that’s produced. Investors, asked to pay upfront development and construction costs, are comforted knowing they have 20-year power purchase contracts that assure they’ll get a decent return on their investment. “I’ve seen this approach work very well in Europe, and Ontario is the only place in North American that has gone in this direction,” says Benedek. “I liked that the government was being ­intelligent in this area.” The program appears to be working. Cambridge, Ont.-based Delft Blue, one of Canada’s top suppliers of veal products, took advantage of the FIT program and now has one of the largest on-farm biogas systems in the province. Manure from its 2,700 calves drops through floor grates in its barns and is collected by gravity to a central location. To keep the process balanced, the manure is mixed with food waste from local grocery stores and locally sourced restaurant grease that is pasteurized on site. Inside Delft’s digester building the organic cocktail is heated to 38 C, sparking the biochemical processes that trigger biogas production. The biogas rises and collects inside an expandable membrane-lined roof. From there the gas is piped to a separate generator room where grid-ready electricity is produced for sale. Waste heat from the generators is recaptured and used on site to heat the stables and water tanks. “The heat cost on the farm is just astronomical, so if we can offset that, we’re looking at a 5½-year payback on the total system,” says Aron Hamm, biodigester manager

at Delft, a division of sustainable agriculture company Grober Green. This assumes one has the upfront capital. Many farmers lack such financial resources and Canadian banks haven’t proved eager to lend, even with the guarantees offered by the FIT program. If farmers do have the cash they often complain that it takes too long to get environmental approvals, or that local utilities won’t take their power because of grid constraints. Some even say the FIT rates for AD-system biogas aren’t high enough. Why, they ask, does a 400-kilowatt solar PV project get 65.5 cents per ­kilowatt-hour while a similarly sized biogas project only qualifies for 15 cents? After all, biogas systems can dispatch electricity when needed; with solar you have a half-day window and are at the mercy of clouds. Program numbers speak for themselves. As of June 10, there were only 42 major biogas projects registered to ­participate in the FIT program, according to the Ontario Power Authority, the provincial agency that issues powerpurchase contracts. Of those projects, only seven are currently operational. Hardly a booming market and well short of the province’s potential. Benedek doesn’t seem concerned — Ontario is part of a much larger opportunity. “We can sell from Ontario into the United States,” he says. As well, UTS’s initial focus will be on large municipal and industrial biogas projects that have better access to capital. The company will also focus on innovation. AD control and monitoring systems can be enhanced, equipment can be better integrated and construction and assembly methods can be improved, all with an eye to raising the bar on system efficiency and reliability. Benedek says the technology isn’t overly complicated, at least on the surface. Like anything, it can be built poorly or to the highest standards, and innovation can help raise those standards and lower costs. “A car isn’t all that complicated either, but over time you make them more sophisticated, reliable and design them for better gas consumption,” he says. “It’s the same with anaerobic digestion, when you have already built 1,600 systems you ultimately wind up learning a great deal about making it better, faster and more reliable.” That’s the edge Benedek hopes Anaergia will bring to Ontario — and beyond.

september 2011 CAnadian Chemical News   27


Society news RECOGNITION

Student Chapters Get an ‘A’ This year’s Canadian Society for Chemistry winner of the Student Chapter Merit Award is the University of Toronto at Mississauga’s Erindale Society of Chemical and Physical Sciences. Canadian Society for Chemical Engineering winners are: the University of Western Ontario, which took first place, and University of Toronto’s Student Chapter, which received honorable mention. The annual awards are given out in recognition of student chapters at universities and colleges across Canada that engage undergraduates both academically and socially. Merit Awards are presented for each society and recognize and encourage initiative and originality in student chapter programming in chemistry, chemical engineering or chemical technology.

Order of Ontario for Shoichet Molly Shoichet, MCIC, University of Toronto’s world-renowned biomedical researcher of regenerative medicine, is among 30 new appointees to the Order of Ontario. Shoichet, who holds the Canada research chair in tissue engineering, is one of 30 appointees to Ontario’s highest honour who were chosen for their contributions to the arts, justice, science, medicine, history, politics, philanthropy and the environment.

Faculty advisor accolade King’s University College’s Kristopher Ooms, MCIC, won the 2011 Canadian Society for Chemistry Faculty Advisor Award. This award is based on a nomination submitted by the Student Chapter recognizing the exceptional performance of their faculty advisor to the planning and implementation of Student Chapter activities.

New President for UPEI Alaa Abd-El Aziz, FCIC, has been appointed president of the University of Prince Edward Island. Abd-El Aziz was formerly provost at University of British Columbia Okanagan.

OUTREACH

Chemistry Fun on YouTube Middle and high school students nabbed cash prizes in the first-ever Chemical Institute of Canada-sponsored YouTube video contest held in honour of the International Year of Chemistry and sponsored by Esso-Imperial Oil. Students submitted three-minute videos based on the theme, “Chemistry — our life, our future.” Each submission was judged on creativity, educational value and quality of video. First prize of $2,500 in scholarship funding went to Pascal Turmel and Jonathan Kwok of Vancouver for their video “Combustion’s Not Always Destruction.” Elisha Walker of Vancouver took second place and $1,000 while third prize of $500 for creativity went to students from Monterey Middle School in Victoria for the video “Chemical Girl,” a parody of Madonna’s 1985 hit “Material Girl.”

H2O under global microscope

As part of the International Year of Chemistry, IUPAC has launched the Global Water Experiment, where students from around the world explore properties of the planet’s most crucial resource — water — and submit their findings to a global database. Four experiments have been designed using common household or classroom materials such as pop bottles and coffee filters. In Canada, students will submit their findings to the database during National Chemistry  Week,  Oct. 15–22. The experiments include determining the pH and salinity of water and constructing water filters and solar stills.

High school chemistry winners Christopher Dee of St. George’s School in Vancouver is the winner of this year’s Canadian  Chemistry Contest for high school and cégep students, organized by the Chemical Institute of Canada’s Chemical Education Division. Dee was chosen from among the first-place finishers representing six regions across Canada. The other winners include: Saba B. Balvardi, Halifax West High School, Atlantic Region; Étienne Lantagne-Hurtubise, Cégep de Trois-Rivières, Région de Québec; Melody (Yun Jia) Guan, University of Toronto Schools, Ontario Region; Kaien Gu, St. John's Ravenscourt School, Manitoba, Saskatchewan and Nunavut Region; and Justine Zhang, Sir Winston Churchill High School, Alberta and North West Territories. Contestants, who took home cash prizes and a certificate, were drawn from the top 10 per cent of high school chemistry students.

Cupcake caper The chemistry department at Memorial University of Newfoundland recreated a famous 1907 event where Ida Freund, Britain’s first woman chemistry lecturer, tested her students on the periodic table by preparing small cakes representing each element. The event was held to celebrate the International Year of Chemistry. In Memoriam

Emmanuel Somers, FCIC, has died in London, Ont. at the age of 85. ACCN extends ­condolences to the family.

september 2011 CAnadian Chemical News   29


Chemfusion

The culinary delights of meat glue he idea of eating a steak made from pieces of meat scraps glued together is likely to stick in the craw for most people. But there are also those who are ready to shell out a small fortune at New York’s uppity WD-50 restaurant for a chance to sink their teeth into shrimp noodles concocted with the same ‘meat glue.’ Rest assured that no horses were condemned to the glue factory to produce transglutaminase, ­colloquially known as meat glue. This enzyme catalyzes a reaction between lysine and glutamine and therefore can link protein strands that include these amino acids. If these proteins are located on the surface of adjacent pieces of meat, the pieces get stuck together almost like magic. The joint then looks just like one of the white streaks of gristle or fat commonly seen in meat. It’s so strong that the meat doesn’t even tear along the ‘fault line.’ Transglutaminase is not foreign to the human body. It is endogenously produced to aid in blood clotting, a process that requires protein molecules to form interlinked complex ­structures. Skin and hair are also composed of proteins that have been bound together and transglutaminase plays a role here as well. In the 1990s, the food industry ­discovered that this enzyme can be isolated in good yield from the bacterium Streptoverticillium mobaraense and that it can be used to restructure meat, fish and poultry. For example, artificial crab legs and shrimp can be made by sticking together ground pieces of cheaper

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seafoods such as pollock. While the taste of such artificial foods can be criticized, there is no health issue associated with consuming transglutaminase. As with any other protein, it is readily broken down into its component amino acids in the digestive tract. Meat glue is produced for the food industry under the name Activa by the Japanese company Ajinomoto, which also markets monosodium glutamate (MSG). Celebrity chef Heston Blumenthal brought transglutaminase out of the shadows at the Fat Duck, the restaurant outside London that some consider the best in the world. Blumenthal’s enthusiasm for creating novel dishes with this enzyme rubbed off on Wylie Dufresne of New York’s famed WD-50 restaurant, who managed to grind shrimp into noodles with the help of transglutaminase and served it on a bed of smoked yogurt. Other chefs who pursue ­molecular gastronomy, defined as the ­application of scientific principles to the creation of new dishes, are pushing the ­transglutaminase envelope. Around the corner are filet mignon with strips of bacon glued to its surface, fish coated with chicken skin to enhance flavour and shrimp burgers held together by cross-linked proteins. How about chicken fat stuck to steak to add a new dimension to chicken fried steak? Just in case your cholesterol isn’t high enough. Unfortunately, transglutaminase also lends itself to some less-savoury applications. Some producers or butchers use it to bind meat scraps into ­expensive prime cuts like filet that they price

septembre 2011

By Joe Schwarcz

accordingly. Any butcher engaging in such a clandestine practice may pay a price. While ingesting transglutaminase is no problem, inhaling the powder can damage the lungs. Consumers don’t have to worry about this, but there is an issue with cooking glued meat. The surface of meat is always covered with bacteria that are killed by cooking. However, with structured meat, some of the outside becomes the inside and if the meat is served rare — as many people prefer — bacteria on the inside may survive. This is the reason why hamburger meat has to be cooked thoroughly. What if meat glue gets on the hands? No sticky fingers here, contact time is not long enough to do anything. The only sticky fingers are the ones involved in extracting money from people by passing off glued scraps as prime cuts. There are other issues as well. Transglutaminase can be isolated from blood, with bovine and pig blood being used commercially, creating a problem for people adhering to religious dietary laws. Meat glue is not allowed in Europe, but can be used in Canada as long as it is declared on the label like any other additive. Finally, one wonders if Lady Gaga’s famous meat dress was held together with transglutaminase. Only her butcher knows for sure. Joe Schwarcz is the director of McGill University’s Office for Science and Society. Read his blog at chemicallyspeaking.com.


Canadian Society for Chemical Engineering

Nominations are now open for the

Canadian Society for Chemical Engineering

2012AWARDS

Do you know an outstanding person who deserves to be recognized?

Bantrel Award in Design and Industrial Practice D. G. Fisher Award Process Safety Management Award R. S. Jane Memorial Award The Syncrude Canada Innovation Award

Act now!

Deadlines The deadline for all CIC awards is December 1, 2011 for the 2012 selection.

Nomination Procedure Submit your nominations electronically to: awards@cheminst.ca Nomination forms and the full terms of rweference for these awards are available at www.chemeng.ca/awards.


Canadian Society for Chemical Engineering

Société canadienne de génie chimique

Innovation, Industry and Internationalization

Innovation, industrie et internationalisation

61st Canadian Chemical Engineering Conference

61e Congrès canadien de génie chimique

London, Ontario, Canada

London (Ontario) Canada

October 23—26, 2011

Du 23 au 26 octobre 2011

CSChE

SCGCh

www.csche2011.ca

ACCN, the Canadian Chemical News: September 2011  

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

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