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july | august 2012

Canadian Chemical news | l’actualité chimique canadienne

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leveraging lignin water works

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Chemical Institute of Canada www.accn.ca


Table of Contents

July | August Vol.64, No./No7

Features CHEMICAL ENGINEERING

Lignol Innovations Ltd.

business

14

Leveraging Lignin

A company in B.C. is among few in the world finding new value in lignin. By Roberta Staley

chemistry

24

Water Works

Chemists are vital to addressing growing global demands on fresh water. By Alanna Mitchell

20

Big Data, Big Money

Multivariate statistical models can improve the ­bottom line for some of the world’s ­biggest  ­chemical companies. By Tyler Irving

Departments 5

From the Editor

7

Letters to the Editor

9

Guest Column By Russell Boyd

10

 hemical News C By Tyler Irving

28

Society News

30

ChemFusion By Joe Schwarcz

july | august 2012 CAnadian Chemical News   3


Call for papers now open! Submit your paper, panel or poster at bio.org/pacrim


FRom the editor

Executive Director

Roland Andersson, MCIC

Editor

Jodi Di Menna

news editor

Tyler Irving, MCIC

art direction & Graphic Design

Krista Leroux Kelly Turner

contributing editors

Peter Calamai Tyler Hamilton Tim Lougheed

Society NEws

Bobbijo Sawchyn, MCIC Gale Thirlwall

Marketing Manager

Bernadette Dacey, MCIC

Marketing Coordinator

Luke Andersson, MCIC

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

Editorial Office 130 Slater Street, Suite 550 Ottawa, ON K1P 6E2 T. 613-232-6252 | F. 613-232-5862 magazine@accn.ca | www.accn.ca

W

elcome to your summer issue! In these lazy days of July and August, we aren’t taking it too easy; for your patio or lakeside reading, we bring you three hard-hitting feature stories. In our business slot, Roberta Staley, former acting editor of this magazine, writes about how one British Columbian company is using lignin — that organic polymer ‘glue’ that binds cellulose together and notoriously complicates the refining of biomass — to its advantage by creating a whole new value stream. In our Q and A, we talk to John MacGregor, professor emeritus from McMaster University about how to make sense — and more dollars — out of the reams of data gathered from industrial processes. And if you find yourself wondering about water as you gaze out over your favourite lake or river this summer, you’ve come to the right magazine. Alanna Mitchell writes about how some key chemistry inventions could provide solutions to the escalating demands on fresh water, if only they could make the jump from the lab to the marketplace.

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Subscription Rates

Hope you enjoy the read!

Go to www.accn.ca to subscribe or to purchase single ­issues. The individual non-CIC member ­subscription price for 2012 is $100 CDN. The institutional subscription price for 2012 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.

Write to the editor at magazine@accn.ca

Change of Address

circulation@cheminst.ca Printed in Canada by Delta Printing and postage paid in Ottawa, Ont. Publications Mail Agreement Number: 40021620. (USPS# 0007–718) Indexed in the Canadian Business Index and available online in the Canadian Business and Current Affairs database. ISSN 0823-5228

Visit us at www.accn.ca july | AUGUST 2012 CAnadian Chemical News   5


Letters to the Editor Cross-culture connection I offer a few non-political comments based on experience of

industry-academic collaboration (Guest Column, ACCN, June 2012, p.9). Time and patience are the first ingredients for successful industry-academic collaborations (IACs). Time is a scarce and valuable resource for today’s academics, contrary to the “dreaming spire” stereotype of university life. Younger faculty are the busiest, while the older academics are under slightly less pressure and may have become disillusioned with the publishor-perish ethos. For such people, an IAC can give a sense of usefulness in a world beyond the confines of academia. The element of partnership is crucial. For a successful IAC, the industrial partner has to realize that his academic collaborator is not a corporate employee; moreover he should not expect immediate problem-solving success. Projects have to fit in with the academic’s skills and interests and the industrial partner has to have a “holistic” view of adding value. Does the academic partner produce students that the industrial partner wishes to hire? Does the academic partner ask questions and pursue topics that generate interest and new ideas among the industrial staff? Further, the industrial partner should recognize that the academic partner wants and needs to publish some papers, so publication should be supported and promoted as long as the commercially valuable intellectual property is protected. Another useful maxim for IAC partnership is to start with small projects and then work up to larger ones. Both sides of an IAC should be prepared to overcome their inherent cultural differences. The plea “only connect” was coined a century ago by the great English novelist E.M. Forster who was concerned about the gap between the humanist and the business cultures. His plea applies with equal force to the gap between our academic and industrial cultures. Malcolm Baird Emeritus professor of chemical engineering McMaster University, Hamilton, Ont. First is first I was interested to read the article titled “Chemical biology

program gets an ‘A’ ” in the May 2012 issue of ACCN (p. 8-9). I congratulate McMaster on their achievement, but would like to point out that theirs is not ‘Canada’s first undergraduate program in chemical biology.’

In fact, our institution, Thompson Rivers University (formerly University College of the Cariboo), established a chemical biology major degree in 2001 within our BSc program. We produced our first chemical biology graduate in 2002 and as of this June, we will have produced 90 graduates with a BSc in chemical biology. As the article noted, the interdisciplinary nature of such a program challenges students to solve complex problems and we have found that our graduates have reaped the benefits of the program’s rigour by being successful in professional careers and graduate schools. Thomas E. Dickinson Dean of Science Thompson Rivers University, Kamloops, B.C. Grid glitch

A point in an article in the June 2012 edition of ACCN (“Think Big”) causes me some serious concern. Page 15 displays a picture of a transmission tower and the suggestion that Canada create a national grid. Let us not forget that due to a relatively minor “glitch” in a small system in Michigan, the resulting cascade failure brought down the electrical supply to much of the northeastern portion of the U.S. and much of southeastern Ontario including Toronto. No, I do not trust the engineers and for-profit energy companies to bullet-proof a system. The expense to protect from that remaining one per cent or so of exposure that has a one in a million chance of occurring is still too much of a risk. Gordon A. Boyce Member, Chemical Institute of Canada Dartmouth, N.S. Corrections: The photo on page 17 of the June 2012 issue is of the Darlington nuclear plant in Clarington, Ont., rather than the Pickering, Ont. plant as implied. On page 28 of the June 2012 issue it was stated that the IUPAC International Conference on Chemical Education would be hosted in Canada “for the first time” in 2014. In fact, it was hosted in Canada once before, by the University of Waterloo in 1989.

Write to the editor at magazine@ accn.ca. Letters have been edited for length and clarity.

july | AUGUST 2012 CAnadian Chemical News   7


96th Canadian Chemistry Conference and Exhibition e Congrès 96 canadien May 26–30, 2013 de chimie et exposition

Chemistry without borders May 26–30, 2013 | du 26 au 30 mai 2013

Chemistry without borders | Chimie sans frontières

QUEBEC CITY QUéBEC Québec, Canada

www.csc2013.ca


guest column

Bright prospects for chemical job hunters

C

anadian Business magazine published an article in their April 30 issue entitled “Where the Jobs Are,” that struck a chord for me. The editors surveyed data on employment and wage levels for more than 600 occupations tracked by Statistics Canada. They selected jobs with at least 10,000 employed individuals and ones that experienced employment growth between 2006 and 2011. They eliminated jobs with median salaries below $60,000. The final list of the 50 best-paying, highest-demand career choices today is based on three criteria: job growth from 2006 to 2011, median compensation in 2011, and the change in the median compensation from 2006 to 2011. The weightings assigned to the three criteria were 50, 40 and 10 per cent, respectively. Of course, I immediately thought of the oil sands and sure enough number one on the list is petroleum engineer, the person who figures out how to get the oil out of the oil sands. According to Canadian Business, it is the fastestgrowing occupation in Canada, with employment increasing by 85 per cent between 2006 and 2011 and a median salary of $92,002 in 2011. I was not surprised to see that number two is nursing supervisor given our aging population. Employment in this category has increased by 46 per cent in the past five years and the median salary reached $74,880 in 2011. Electrical and telecommunications contractors are number three on the list with a 2011

median salary of $69,160, while data analysts are in the number four position at $66,040. The growth in these two categories — 67 per cent and 64 per cent, respectively — is not surprising given the importance of information and communications technology and the impact it has on our society. I was delighted to see that Canadian Business placed chemist and chemical engineer in the number five position with a five-year growth rate of 53 per cent and 2011 median salary of $67,330. Initially, I thought that the need might be tied to the oil sands and that the article would emphasize chemical engineering. (In fact, the story points out that the oil and gas, and metals and mining sectors pay chemical engineers better than other sectors, but they employ only about 7 per cent of the profession. About 70 per cent of chemical engineers work in manufacturing and related sectors as diverse as waste management, pharmaceuticals and food processing.) As a chemistry graduate, I was gratified to see that the article mentioned that chemists are needed for many reasons, including seeking out new sources of energy. The full range of opportunities for chemists was not outlined, but two areas of growing demand were noted: the environment and water-related fields, and workplace safety and health. I think this is very encouraging and it makes me optimistic about the future demand for chemists and chemical engineers. It is apparent that the formal

By Russell Boyd

education of chemists and chemical engineers prepares them to be problem solvers and leaders in many fields. (And if the stature of Angela Merkel — physical chemist and German chancellor — is any indication, this includes the elected leaders of G8 countries.) The CIC has an important role to play in serving these future leaders in the chemical sciences and engineering, and making sure their contributions are recognized and their potential maximized. One important thing for us to do is to continue to improve communications with CIC members and key stakeholders whose decisions have both direct and indirect impacts on our members and the CIC and its Constituent Societies. Much has been achieved in the area of communications in the recent past, but much remains to be done to engage and communicate with our younger members and the next generation of members. Also, we must continue to build stronger ties to industry and to make sure that the CIC does not miss out on opportunities in areas such as biotechnology and materials science. I thank all members of the CIC for the opportunity to be the Chair of your board. I will do my best to serve the interests of the CIC. Russell Boyd is the 2012-2013 Chair of the Board of Directors of the Chemical Institute of Canada and a professor in the Department of Chemistry at Dalhousie University.

july | AUGUST 2012 CAnadian Chemical News   9


Chemical News Polymers

Diblock copolymer creates stain-resistant fabrics Imagine a fabric that could simply shrug off even the worst stains, from red wine to ketchup. That’s exactly what’s been developed by researchers at Queen’s University, who have created a superamphiphobic coating for cotton textiles using a diblock copolymer. The key to increasing the repellency of cotton is to coat it with compounds that have low surface energy, usually fluorinated ones similar to polytetrafluoroethylene, or Teflon. In the past, small molecules with fluorinated tails and reactive heads have been used to form low-energy films attached to the hydroxyl groups on cotton surfaces. While they do increase water and oil repellency, normal use often exposes gaps in these films, and washing can remove the coating. Guojun Liu and Dean Xiong of Queen’s Department of Chemistry are experts in superamphiphobic coatings. In a paper recently published in Langmuir, they describe a diblock copolymer that consists of about 10 units of poly-3-(triisopropyloxysilyl)propyl methacrylate (PIPSMA) and 10 more of poly-2-(perfluorooctyl)ethyl methacrylate (PFOEMA). The PIPSMA block anchors the molecule to hydroxyl groups on the surface of the cotton, while the fluorinated PFOEMA

Diiodomethane

hexadecane

Cotton coated with a new diblock c­opolymer repels hydrophobic and ­hydrophilic substances alike; drops of liquid­can sit on the surface of the fabric­for over a year.

Biochemistry

Shedding light on charge separation Canadian researchers studying a light-capturing enzyme complex have caused it to retain a charge for a hundred thousand times longer than usual. The results could have important implications for the engineering of artificial solar harvesting materials. Laszlo Kalman and his team in the Department of Physics at Concordia University have been studying the light-harvesting apparatus of the purple bacterium Rhodobacter sphaeroides. The photosynthetic reaction centre (RC) of this organism is a trans-membrane protein incorporating various pigment molecules, including carotenoids and chlorophyll. When excited by a photon, an electron from one of these pigments is shuffled around to create a positive charge on one side of the membrane, and negative charge on the other. “Given the dielectric properties of the protein, the laws of physics require that the electron has to return to the original pigment within milliseconds,” says Kalman. In a study recently published in the Journal of the American Chemical Society, the team placed the R. sphaeroides RC in an artificial cell membrane made of phospholipids with shorter tails than those that make up the bacterial membrane in order to better examine its properties. The changes caused the membrane to stretch and the RC to be compressed. Using optical spectroscopy, the team determined that the amount of time it took for the transferred electron to return to its original place was increased from 0.1 seconds to over eight hours. Charge-separated proteins, which transfer charges within a complex, are very different from batteries which transfer charges over large distances from molecule to molecule, and it’s not clear that it would be possible to make them into a practical device. Still, the discovery has implications for those searching for new light-harvesting materials. “What I hope is that other researchers can utilize this information to make artificial photosynthetic reaction centres, which are not so sensitive to environmental conditions and which could exist in the solid state,” says Kalman.

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july | AUGUST 2012

Dean Xiong

water

group gives the desired low-energy surface. Experiments showed that the polymers pack very densely on the cotton surface, giving rise to a thick amphiphobic surface that is hard to breach with normal use. The large PIPSMA anchor resists removal during washing. Liu imagines many commercial applications, from stainrepellent lab coats to high-performance swimwear that could cut through the water by trapping a layer of air next to the fabric. If the cost is low enough, the coating could even be added to everyday clothing to prevent stains. “You’re not coating a lot of polymer, so I don’t think it would be too expensive,” says Liu, adding that the processes for making the polymers and coating the cotton are relatively straightforward and amenable to scale-up. Xiong and Liu have filed patent applications internationally and are working with Queen’s’ technology transfer office and an unnamed industrial partner to commercialize the innovation.


Canada's top stories in the chemical sciences and engineering

| Chemical News

Biotechnology

Improved stem cell production enables new applications The potential of stem cells to cure diseases can only be realized if they can be produced in large quantities with a high degree of control. Two Canadian groups of researchers recently demonstrated that suspended culture bioreactors can be used to do just that. Differentiated tissue cells (somatic cells) can be reprogrammed back into pluripotent stem cells by activating certain genes, known as Yamanaka factors, after their discoverer. The cells thus derived are called induced pluripotent stem cells (iPSCs) and are typically made from fibroblasts from skin. However, because fibroblasts can only grow when adhered to a solid substrate, to date iPSCs have been produced exclusively in petri dishes. Two papers published in the May issue of Nature Methods show that this isn’t strictly necessary; as cells transform from fibroblasts into stem cells, they lose their dependence on adherent conditions. Peter Zandstra of the University of Toronto’s Institute for Biomaterials and Biomedical Engineering and his team used a transgenic mouse cell line in which the Yamanaka factors are induced by

the antibiotic doxocycline. In contrast, Derrick Rancourt’s group at the University of Calgary used viral vectors to get ordinary mouse fibroblasts to express the Yamanaka factors. In both cases, transformed stem cells were able to grow and proliferate in suspended-culture bioreactors of the type that are widely used in biopharmaceutical production. “By forcing them to survive in a suspension environment, we’re creating a selection pressure which enhances the reprogramming process,” says Rancourt. In addition to allowing for scaled-up production, bioreactors offer consistent control over culture conditions. Large quantities of cells produced this way could be used for personalized medicine in humans; for example, tissues derived from a particular patient could be screened for the most effective drugs. Eventually, replacements for damaged or diseased tissues could be grown in the lab. Both Zandstra’s and Rancourt’s groups are extending the process to human stem cells. “We hope to take technologies like this and catalyze a cell manufacturing industry here in Canada,” says Zandstra.

Carbon Capture

New chemical combination could improve carbon capture

Jason Clyburne

Current methods for CO2 capture from flue gases are energy-intensive, and consequently too expensive for most applications. A new solvent/amine system developed at Saint Mary’s University could change that. The standard practice is to bubble the gas through a solution of about 20 per cent monoethanolamine (MEA) in water. CO2 dissolves and forms an adduct with the MEA — this releases a proton which must be accepted by a second MEA molecule. The solution is then heated to release gaseous CO2 and regenerate the MEA. “The problem with these MEA/water catch-and-release systems is that they have a very high heat capacity,” says Jason Clyburne, professor of chemistry at Saint Mary’s University. “The catch is very good, but the release is very costly.” As a result, it is currently only useful in high-value applications, such as purification of natural gas; for economical greenhouse gas mitigation the cost needs to be reduced significantly. Clyburne and his team surveyed many alternatives, both for the capture molecule and the solvents. In a paper published in Industrial and Engineering Chemistry Research, they point out that diethylenetriamine (DETA) is similar to MEA, but is much less volatile and contains multiple amine groups. This means it doesn’t require a second molecule to accept a proton, and can be used in a 1:1 ratio to capture CO 2, rather than the 2:1 ratio required by MEA. As for the solvent, the team tested various compounds that would be non-volatile, robust under process conditions, and have a lower heat capacity than water. Several ionic liquids were investigated, but in the end a similar performance at much lower cost could be obtained with a commercially-available polymeric solvent. The new solvent/amine system is undergoing testing, but so far indications are that it will release CO 2 at significantly lower energies than traditional MEA/water systems. Clyburne has filed a patent application and is collaborating with GreenCentre Canada, a green chemistry commercialization centre in Kingston, Ont., to bring the discovery to market. “My gut feeling is it won't take very long,” says Clyburne.

MEA

DETA

Monoethanolamine (MEA) (top, reactant) is the industry standard for carbon capture. It forms an adduct with CO2, but requires a second molecule to accept the proton generated, forming a carbamate salt. The ratio of MEA:CO2 must be 2:1. Diethylenetriamine (DETA) (bottom, reactant) contains multiple amine groups, and instead forms a zwitterionic CO2 adduct with positive and negative charges in different locations. Thus, DETA reacts at a 1:1 ratio, which could improve the efficiency of carbon capture from flue gases.

july | AUGUST 2012 CAnadian Chemical News   11


Chemical News Pharmaceuticals

Antipsychotic drug targets cancer stem cells Thioridazine, a drug normally prescribed as an antipsychotic, has been found by researchers­ at McMaster University to also target cancer stem cells. The finding led to the identification of new biomarkers that could lead to early cancer detection. Cancer stem cells are hard to identify ­because they look so much like normal stem cell counterparts. Their distinguishing ­characteristic is their ability to regenerate without differentiating into other tissues, which keeps tumours coming back even ­after radiation­or chemotherapy. Mickie Bhatia of McMaster’s Department of Biochemistry and Biomedical Sciences and his colleagues developed a high-throughput screen to compare the effect of a given drug on both pluripotent stem cells and cancer stem cells. “Previous screens looked at the ability of drugs to kill cancer stem cells,” Bhatia explains. “We were simply trying to make them differentiate like normal stem cells, something others hadn't done.” In a paper recently published in Cell, they tested 2,600 off-patent drugs of which only about one per cent showed activity. Thioridazine had one of the strongest and most selective effects­,

causing differentiation of cancer stem cells but leaving normal ones alone. Since differentiated cells eventually die, thioridazine could serve as an effective therapeutic against cancers like leukemia. Thioridazine is known to inhibit dopamine receptors. Further ­investigation showed that these receptors are indeed present in greater concentrations on the surface of cancer stem cells, indicating a potential new biomarker of cancer. “What’s so exciting about this work is the ability to use these chemicals beyond just drug response, as a way of probing signalling pathways that might be relevant to ­distinguishing cancer stem cells from normal ones,” says Bhatia.

The antipsychotic drug thioridazine, one ­enantiomer of which is shown here, can ­selectively target cancer stem cells and cause them to ­differentiate.

materials

Wheels on the MOF go round and round

To ‘spin one’s wheels’ usually means a failure to make progress, but last month a group of researchers from the University of Windsor spun themselves onto the ­cover of Nature Chemistry. They’ve created the first metal-organic framework (MOF) with rotating dynamic components; the innovation could bring us one step closer to ­molecular computing. Stephen Loeb’s group in Windsor’s Department of Chemistry specializes in rotaxanes, a type of mechanically interlocked molecule where a cyclical ‘wheel’ freely rotates around a straight ‘axle.’ Large functional groups on either end of the axle prevent the wheel from slipping off. The group has even created rotaxanes where a single wheel can jump between two discrete locations on an axle, acting as a molecular switch that could encode digital information. Until now such molecules had only been made in solution. “If you want to make random access memory using these things, then you’ve got to organize them in some way,” says Loeb. In the paper, the group describes a simple rotaxane in which the functional groups on the end have been modified into carboxylate groups. These groups interact with copper-based metal-organic complexes to form a solid-state, three-dimensional MOF. Experiments using NMR with deuterium labelling conducted by Robert Shurko’s group

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Canada's top stories in the chemical sciences and engineering

| Chemical News

earth chemistry

Department of Earth and Atmospheric Sciences, University of Alberta

Organic carbon on Mars is abiotic

The Tissint meteorite, a 58 gram sample of which is shown here, landed near Tata, Morocco in July of last year and was confirmed as martian in January. A new study shows that it and several other martian meteorites contain organic carbon of ­non-­biological origin.

Curiosity, NASA’s latest Mars rover, will begin its search for chemical evidence of past life on the red planet in early August. But according to a new paper in Science, the surface of Mars contains organic carbon generated by non-biological sources, which could make that search even harder. Very rarely, material ejected from the surface of Mars by cosmic impacts can make its way to Earth in the form of meteorites. Only about 60 martian meteorites are known, eleven of which were part of the study conducted by an international team of experts, including Chris Herd of the Department of Earth and Atmospheric Sciences at the University of Alberta. Inside the martian minerals, the team found particles of carbon. “What's interesting about this stuff is that it’s not just graphite, it's organic macromolecular carbon,” says Herd. Organic carbon is present in the dust from which the solar system formed, as evidenced by primitive meteorites which can contain anything from polycyclic aromatic hydrocarbons to amino acids. Similar material would have been incorporated into Mars as it formed, stored in its interior, and could later have reached the surface by means of lava flows. To test this theory, lead author Andrew Steele of the Carnegie Institution of Washington used confocal Raman spectroscopy, which allows for accurate determination of both the form and location of the carbon within a given meteorite’s crystal structure. In every case, the organic carbon particles were found in inclusions within igneous minerals. “The only way it could get there is if it was present in the original magma,” says Herd. “If it had been formed by some kind of biological process, you'd expect to find it associated with rust or material that formed through alteration by water, not with the igneous minerals.” Although the finding doesn’t completely rule out the possibility that Mars once harboured life, it serves as a reminder of just how hard Curiosity will have to work to prove otherwise.

in the same department demonstrated that the wheels were indeed spinning, at speeds above 10 MHz. Loeb’s group has made MOFs with switchable rotaxanes as well, but proving that the wheel can not only rotate but translate along Stephen Loeb

the axle has proven difficult. Another huge challenge lies in determining how to trigger individual molecular switches by either electrical or photochemical means, something that Loeb admits is still “science fiction.” Still, if it could be done it would yield a material with a density of switches over a billion times higher than today’s most advanced devices.

In the metal-organic framework developed by Stephen Loeb's group at the University of Windsor, circular crown ether 'wheels' (represented by yellow toruses) are able to spin around organic 'axles' connected by complexes of copper (brown spheres). This is the first time a rotating mechanically interlocked molecule has been synthesized in the solid state.

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june 2012


Business | LIGNIN

Leveraging British Columbia-based Lignol Innovation’s modest size belies its status as an emerging world leader in the development of fuelgrade­ethanol and multi-purpose­­renewable products from lignin. By Roberta Staley

Lignol Innovations Ltd.

A Tanya Souter and Brian Brittan attend to the fermenters at Lignol’s pilot plant. Inside the machinery, cellulose is converted to ethanol with enzymatic hydrolysis and yeast fermentation.

faint chemical odour, slightly astringent but not unpleasant, fills the laboratory air at Lignol Innovations Ltd. “That’s ethanol,” says Michael Rushton, Lignol’s Chief Operating Officer. “We love it,” he adds, striding past gleaming white metal and glass lab equipment, through a heavy door into a concrete labyrinth filled with fermenters, distillers, pipes and barrels. Lignol is a Burnaby, B.C.-based, 2,140 square-metre, pilot-scale biorefinery surrounded by fragrant woodland heralding a lush West Coast summer. Inside, the scent of ethanol proclaims its own bright promise: progress, innovation and hope for a renewable, low-carbon future. Lignol Innovation’s parent company is Lignol Energy Corp., a small, TSX Venture Exchange company. Lignol’s market capitalization is about $5 million, although “our true valuation is many times that,” Rushton says. Despite its modest stature on the stock exchange, Lignol is a global standard bearer — “perhaps not the world leader, but a world leader” — in the development of biorefining technologies to produce economically viable, fuel-grade ethanol and renewable chemicals from cellulosic biomass feedstocks such as woodchips. Created in 2001, its potential has been nurtured by various levels of government. This past February, Lignol received $2-million in funding from Sustainable Development Technology Canada (SDTC), a federally funded not-for-profit foundation. This bolsters the $4.72 million Lignol received earlier from the SDTC Tech Fund, which backs innovative technology, especially clean-technology projects.

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of such a biofuel. Natural gas is at its lowest price in a decade and the price of a barrel of oil is not yet high enough to instil real urgency among governments or the public to push for greater biofuel innovation and adoption. There is some progress, however. Since September 2010, the Canadian government has mandated that refiners blend a minimum of five per cent renewable fuels into gasoline; in B.C., gasoline

Biomass

Hardwoods, Softwoods, Agri-Residues

Cellulose

AlcellPlusTM Organosolv Biomass Extraction Hemicellulose derivatives

Cellulose derivatives Sugars • Dissolving pulp • Cellulose chemicals • Fibre ingredients

Lignol Innovations Ltd. uses a patented organosolv biomass extraction process called AlcellPlus™ to produce three value streams from hardwood, softwood and agri-residue feedstocks.

Mixed sugars (C5+C6) and chemicals Xylose, xylitol Furan chemicals • Furfural • Furfuryl alcohol • HMF Biofuels • Ethanol • Drop-in fuels • Bio-butanol Fermentation-based biochemicals

contains 10 per cent ethanol. B.C.’s ethanol is imported from the United States or Ontario, where it is made from corn, or Alberta, where it is made from wheat, Rushton says. Lignol is adapting cellulosic ethanol production from wood for the 21st century. In the past, this process has been complicated by the presence of lignin, an organic polymer that acts like ‘glue,’ strengthening the long fibres of cellulose in plants and trees and binding the cellulose and hemicellulose. Lignol’s process for separating

July | August 2012

lignin from cellulose — known as Alcell ™ — is a technology pioneered by Kendall Pye of Philadelphia with General Electric; today Pye is Lignol’s septuagenarian Chief Scientific Officer. Alcell is an ethanol-based organic solvent system that, combined with heat and pressure, separates lignin from cellulose. This results in a much cleaner separation than traditional kraft pulping employed by most pulp

Lignin derivatives HP-LTM lignin Petrochemical substitution­ • Phenol • Isocyanates • Furans • Plastics • Coatings New functional products • Carbon fibre • Antioxidants • Adsorbents • Feed additives

and paper mills, which relies on strong bases to break down the lignin. Once the lignin is separated, cellulose and hemicellulose are converted to sugars and then to ethanol through enzymatic hydrolysis, fermentation and  distillation. Hydrolysis is typically limited by the efficiency of the enzymes as well as the presence of residual lignin, among other things. “What gives us a competitive edge is the fact that our cellulose is so easy to degrade using enzymes because it’s so clean — we’ve taken out the lignin,”

adapted from Lignol Innovations Ltd.

Such monies seed the ground of what Rushton says will be a “north of $100-million” integrated commercial biorefinery in the near future that produces cellulosic ethanol that is cost competitive with gasoline. Such a facility — blueprints have already been completed that promise an initial annual output of about 30 million litres of cellulosic ethanol — is dependent upon numerous factors: leveraging Lignol’s intellectual property portfolio and cultivating new relationships with corporate investors and partners, says Rushton. Just as exciting is the develop­ ment of lignin as a separate product stream and source of revenue. With two such key products, the end result of the commercial facility is a fully integrated biorefining process “with biomass coming in and a whole bunch of products coming out,” Rushton says. Lignocellulosic-based biorefineries that generate fuel, power and renewable products from biomass are likely to be an integral part of the future of sustainable energy. One of the holy grails of renewable energy is the development of fuel-grade ethanol from locally-sourced feedstocks. Brazil is a world leader in first-generation ethanol production, thanks largely to vast tracts of arable land and a bounteous supply of cheap sugar cane. Lignol is working to perfect second-generation cellulosic ethanol, using its pretreatment-process chips, straw or corn stover to create a pulp that, instead of being turned into paper, is converted into fuel with new unique enzymes. Perhaps surprisingly, says Rushton, who is a chemical engineer, there is very little cellulosic ethanol available anywhere today. In Canada, there are several factors slowing progress towards a more wholesale adoption


Lignol Innovations Ltd.

says Rushton. To further enhance hydrolysis, Lignol uses special enzymes supplied by research and development partner Novozymes, a global company specializing in enzyme innovation. The resulting sugars are fermented by yeast in a process similar to making beer, Rushton says. “In fact, we call it beer: it has a lot of water and a bit of yeast and about seven to 10 per cent ethanol.” Any similarities with beer end there. “It smells terrible.” This “beer” then undergoes a standard distillation process, turning it into fuel-grade ethanol. During the Alcell process, the lignin is extracted as a liquid, then washed and dried, resulting in chocolate-brown powder as fine as flour. Currently, in most pulp and paper mill operations, lignin is burned to produce process heat and recover pulping chemicals. Such conventional lignin also has been used to replace petroleum-based substances for making resins and dye dispersants. But Lignol has taken it a step further, finding numerous new applications for its lignin. The company has created “second-generation” lignin, High Purity Lignin or HP-L™, to distinguish it from conventional lignin obtained from the pulping process. HP-L is a step above both chemically and structurally, Rushton says. It has very few contaminants and only traces of sulphur and inorganic material. It also has a very narrow molecular weight profile and water repellent properties. This purity means that it performs differently when put into chemical systems, potentially displacing an even wider range of fossil fuel-derived products. Any remaining residues from the process are used for steam and electricity generation, thus

Samples are taken from the distillation system at Lignol’s pilot plant by operators Tanya Souter and Colin Braconnier. Distillation is one of the final steps in the ethanolmaking process, yielding 10 per cent alcohol as well as non-fermentable solids from the feedstock and yeast cells.

July | August 2012 CAnadian Chemical News   17


reducing Lignol’s dependence on natural gas to provide energy. “The trick is that you have to make these processes all work together and that is where the integration comes in — the chemical engineers have to figure out how to do this in an efficient way,” says Rushton, who is one of about 30 staff at Lignol. There are only a handful of companies in the world that are advancing lignin as a commercial multipurpose biomaterial. Two of the biggest players include the venerable Norwegian chemical specialty company Borregaard Industries Ltd. — its lignin goes into well-established end-uses. Another leader is Mead Westvaco of Virginia, which produces specialty papers and packaging as well as specialty chemicals. Lignol is one of just a few actors on the Canadian stage producing either cellulosic ethanol or lignin. A former bright light, Ottawa’s Iogen Energy Corp., owned by Royal Dutch Shell and Iogen Corp. announced this past April that it had quashed plans to build a larger scale cellulosic ethanol facility in southern Manitoba. Iogen was known for developing an enzyme-based process that broke down crop-waste cellulose, making the sugars easy to access for conversion into ethanol fuel. But a

18  CAnadian Chemical News

July | August 2012

companies as Kingspan Insulation, Huntsman Corp. and HA International LLC, an Illinois-based global producer of foundry resins. Lignol’s high-purity lignin was used by HA International to produce a new foundry resin used in the production of metal castings, replacing petrochemicals normally used in the resins. Lignol’s HP-L can displace other non-renewable resins used for manufacturing plywood, engineered wood composites and oriented strand board, which is used as a replacement for plywood. HP-L can also be used as an antioxidant in greases and lubricating oils and friction materials such as brake pads. Most interesting, perhaps, is the use of HP-L by Tennessee’s Oak Ridge National Laboratory in the manufacture of carbon fibre. To date, carbon fibre has been made from petroleum products. Light and strong, carbon fibre is used almost exclusively in the luxury car and aerospace industries due to its high price. HP-L will figure largely in the development of future materials, possibly even replacing steel for some applications, Rushton says. “It’s very exciting.” Some pundits have criticized Lignol for being too dependent for too long a time on the public purse — its potential being its main selling point, commercialization hovering just out of reach. Rushton says that patience is needed. The first oil well in Canada was drilled in 1859, resulting in a 153-year evolution to achieve “this very sophisticated integrated petrochemical industry that we have today. I think the substitution with renewable materials is a long path and we’re just at the beginning of that path,” says Rushton. “I think we’ve got time.” Roberta Staley is a freelance writer based in Vancouver.

Lignol Innovations Ltd.

Michael Rushton, Chief Operating Officer of Burnaby, B.C.'s Lignol ­Innovations Ltd.

promising new upstart is G2 BioChem, launched by GreenField Ethanol Inc. of Chatham, Ont. Backed by companies like Novozymes, G2 BioChem was created by Greenfield — Canada’s largest ethanol company — to accelerate the commercialization of its product. One of Lignol’s preferred sources of feedstock, says Rushton, is mountain pine beetle-killed lodgepole pine lumber, which forestry companies in B.C. are hurriedly harvesting to allow replanting of about 17.5 million hectares of affected forest. “These are very much the typical wood chips you would find being fed to a pulp mill.” Rushton says that the use of cellulose from B.C.’s vast feedstock resources — especially beetle-killed pine — is part of good forestry management. Firstly, the dead trees are extremely dry — tinder for forest fires. Secondly, the millions of hectares of dead trees must be removed to allow replanting, and it would be a waste not to use the wood. Although B.C. is regarded as one of the largest sources of raw material in Canada, Rushton muses that the 20- to 30-year gap needed for new trees to grow in pine beetle-killed forest tracts may have negative implications for feedstock sources down the road. As a research and development facility, Lignol collaborates with a number of companies to help develop new uses for its lignin that will help accelerate construction of a commercial biorefinery. Recently, Lignol delivered several tonnes of material to a major manufacturer that makes coatings for automobiles and industrial machinery for testing in its facility. (Rushton won’t name the company.) Lignol has also begun carving out its own niche for HP-L in collaboration with such


discount members for CIC/CSChE

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&

data Money

John MacGregor uses multivariate m ­ odels to i­ mprove the b ­ ottom line for some of the world’s biggest chemical­ ­companies.

Sophisticated online sensors and increasingly efficient computer storage banks have given chemical engineers access to more data about their processes than ever before. But more data does not necessarily equate to more knowledge, and few people understand that as well as John MacGregor. MacGregor, professor emeritus at McMaster University, has dedicated his career to making sense of the large and messy data sets generated by industrial processes. As president of ProSensus Inc., he has helped Fortune 500  companies reduce costs, increase yields, and improve the quality of products from polymers to potato chips. ACCN spoke with MacGregor to find out how engineers can make the most of industrial process data.

ACCN You have said that learning from data is “the engineer’s Achilles heel.” Why? JM During their undergraduate programs, scientists and engi-

neers are taught very simple statistical methods, aimed at analysing a small number of variables in a designed experiment, and where it is assumed that all process variables are independent. This is very different from the data we collect on industrial processes. Those data sets are huge, with hundreds or thousands of variables from various points in the system: temperatures, pressures, flow measurements and so on. Up to 20 per cent of the data is missing. Most importantly, this data is not independent: when certain things happen in the process, many variables move together. What that says is that the system is really moving in a much smaller space, maybe only five or six variables in dimension.

20  CAnadian Chemical News

July | August 2012

By Tyler Irving

ACCN These are the latent variables? JM Yes. Latent variables are just linear combinations of the original hundreds of variables which define the lowdimensional space in which the process moves. They are the underlying or hidden variables that characterize the process. In order to get at these latent variables, you need multivariate statistical methods. That means modelling not only the properties of the final product, but the process variables themselves. It may seem strange to model the inputs, but if you don’t, you can’t handle missing data, and you don’t get a unique model which you can use for optimization or control. That’s why it is the engineer’s Achilles heel; he’s never been prepared to handle this type of data, and yet these are the very processes that he has to deal with in his job. Modelling the process variables and the product variables (the x and y space) separately is not a totally new idea; the original concept goes back to the introduction of principal component analysis by a statistician called Pearson back in 1900. But without computers and big database systems, it wasn’t really possible to take advantage of these tools in order to predict and control the process.

ACCN What was the field like when you first started­ working in it? JM Until the late 1960s and early 1970s, process data was just

recorded with analog instruments; databases really didn’t exist. Even after computers came in and people began to store the data, there was no ability to extract, for example, a group of


Chemical Engineering | DAta 30 or 40 variables over a given time period. Even until the early 1990s, you would have needed someone to write special ­software. The main objective of databases was to display the data to the operators, not to analyse it. I came to McMaster in 1972 after working with Monsanto in Texas, and I accepted the position with the intention of doing a fair amount of consulting. I felt it was important to play research, teaching and industrial consulting off each other. So I would talk to the big petrochemical companies like ExxonMobil, British Petroleum, Shell and DuPont. I’d ask “How much money have you made off your databases this year?” and they’d just have a gentle laugh. By the mid 1980s, they stopped laughing. They realized that if they had spent this much money on databases, they should do something with the data they were collecting. ACCN What happened next?

a potato chip. In the late 1980s we started using colour digital cameras to extract information on product quality. Imaging companies of the time were mostly using ­black-and-white cameras to simply monitor the process, as operators do now. We looked at multi-spectral images and ­realized that instead of treating them as images, we could think of them as a source of data. We could use this data to extract information, just like we would use thermocouples or flow meters. Best of all, a good, robust industrial camera costs only a few thousand dollars; if the public didn’t use these things and you had to buy them as an industrial instrument, they would perhaps cost half a million dollars. ACCN So they’re the same as the digital cameras that everyone is familiar with now? JM Well, some are line-scan cameras that just capture the

JM We started getting some grants from companies. At that

time, very few academic researchers had grants from industry, and the grants we got were very small. Eventually, we put together something called the McMaster Advanced Control Consortium (MACC). We had six sponsors, big petrochemical companies like Shell, Dupont and Suncor. That eventually expanded to almost 20 big international companies, and the consortium is still running today, and greatly improving the operations of the plants around the world. ACCN One of your major innovations has been in  multivariate modelling of digital images; how did that come about?

image at multiple wavelengths along one line as the ­material passes underneath. But we can also use an area scan, more like a ­traditional camera. Many companies around the world do image analysis, but very few of them get into sophisticated analysis in the multi-spectral range. To do that you have to know how to take megapixels of data every second and extract useable ­information, which means you need multivariate methods. So our past experience, combined with the new technology, enabled us to help companies that couldn’t previously get this kind of online data. ACCN Can you give some examples? JM Frito-Lay was one of our member companies in the consor-

JM In the consortium we had a number of companies that made

ProSensus Inc.

Seasoning level

solid products, whether they were pulp and paper companies like Tembec, steel companies like Dofasco or food companies like Frito-Lay. It’s not easy to stick a thermocouple into

tium, so we started imaging snack food products such as Doritos, Cheetos and Tostitos as they passed by on moving belts. We used the cameras to extract estimates of the distribution of the seasoning applied to the chips and several other

Non-seasoned

Low-seasoned

By analysing the spectral data in digital images­of corn chips (top row) ProSensus Inc. is able to develop computer models that accurately predict seasoning levels (bottom row) and correlate them to particular process conditions that can be controlled. Systems like this are used for on-line feedback control in snack food plants around the world.

High-seasoned

July | August 2012 CAnadian Chemical News   21


ACCN Such as? Multivariate statistical methods can be applied to databases of raw materials, previous product formulations and ­processing conditions to ­design new ­products, such as  ­high-­performance cores for golf balls.

organoleptic properties such as texture. They were astounded at the information we were able to extract from the images. Within a couple of years, we had systems online in many of their plants in North America. They actually control parts of the plant operation off the cameras. Another project was with Dupont Canada. At their site in Maitland, Ont., they had a waste boiler to generate steam by burning many of their waste liquid streams. They had a camera which was used by the operators simply to ensure the flame was still lit. We decided to digitalize that flame image. They had a hard time believing we could do anything with that data, because the flame was bouncing all over the place. But we showed that regardless of the turbulence, the spectral data gave a consistent picture of the energy content in the feed stream, as well as what pollutants were going out the stack. So we could use multivariate analysis to predict and control that. We’ve used that same technique with Irving Pulp and Paper in monitoring lime kilns, and with steel companies in their oxygen furnaces. ACCN In 2004, you launched ProSensus Inc. Why was it the right time to do that? JM I had thought about doing it before, but it was mainly in

order to spin off the multivariate image analysis. One of my PhD students was graduating and wanted to continue working in this area. However, there was no company that really understood it well enough to continue. So we spun it off as a company, to open up job opportunities for graduates from our program, and to be able to advance these technologies further with member companies from the consortium. We quickly found that some companies weren’t quite ready to make a leap into the advanced imaging work. So we went back to multivariate methods for extracting data for other purposes. One area that we got into was rapid product development — how companies use all the data they’ve got on raw materials, formulations, processes and quality control to develop new products with desired properties.

22  CAnadian Chemical News

July | August 2012

JM An example of early success in this field was a project on

advanced polymeric materials, which we did in partnership with Mitsubishi. Some of these materials were for medical devices, while others were for specialized applications like golf balls. Golf balls contain multiple rubber cores to control the distance, spin and about a dozen other properties. We built statistical models that told them to use formulations containing raw materials that they had never used before, but that we predicted would have the desired properties. They tried it, and met the specifications almost right off the bat. Our methodology was used to develop all the core functional polymers in the Srixon golf ball; about 10 per cent of the world's touring pros now use that ball. A company like Mitsubishi would typically take two to four years to develop new products, but with our methods we can get that down to a couple of months. ACCN Should we approach statistics differently than we currently do? JM It’s coming, but very slowly. I think part of the problem is

that there are very few people trained in these multivariate methods. That's why ProSensus developed multivariate software, which we make available for free to the universities. McMaster has introduced some of this into the undergraduate courses, but most universities are using it at the graduate level. American universities are behind the Canadian ones; very few of the American engineering schools have statistics as a required course, even for undergraduates. A lot of that is because they are really gearing their students up for graduate work, not for dealing with industrial data or everyday problems. So while many companies do use this stuff, engineers more or less have to learn it after they graduate. ACCN What has kept you motivated about multivariate­ techniques all this time? JM For me, the interest — and the reason I formed ProSensus

even as I was getting close to retirement — was in seeing this stuff through and having it applied in industry at a more rapid pace. It’s exciting to do this research, but if you just publish a paper on it, and it never gets used, it’s not very satisfying. We’re taking it beyond the published literature, developing new products in a fraction of the time it used to take, and creating control systems to do things that nobody’s ever done before. It has taken off extremely well, and that’s been extremely ­satisfying to see.


the work of chemists in university labs across Canada will be vital to addressing growing global demands on fresh water. But only if their ideas can flow effectively into the marketplace.

By Alanna mitchell

F

ew of those browsing the web know that Google was created by university scientists. In fact, the Internet search giant, with market capitalization of $193 billion and a new-found appetite for smartphones, was invented by two grad students and started life at Stanford University in California. Across the world, universities are hotbeds of innovation. And in Canada, a growing amount of that Ivory Tower ingenuity involves a vital subject: water. Unfortunately, many of the great Canadian solutions to water issues stay locked away in labs, never making it to the market. That’s happening despite the fact that the need for marketable, environmentally friendly water inventions — a.k.a. the Blue Economy — is more pressing as climate patterns change, the population increases and people all over the world strive for a higher and more water-rich standard of living. The result, say some of those charged with bringing lab-born brainwaves to market, is that Canada has spent as much as $6 billion a year to fund academic scientists, but their discoveries aren’t making life better, greener or bluer for Canadian citizens. “There’s no shortage of discoveries,” says John Molloy, president and chief executive of PARTEQ Innovations, a Kingston, Ont.-based company set up to take inventions from Queen’s University to market. But, unlike the United States, Canada still lacks the suite of models necessary to push academic inventions into the marketplace, Molloy says.

24  CAnAdiAn ChemiCAl news

junE 2012


Chemistry| water

A report from the Conference Board of Canada in June 2011 ranking 17 developed countries on innovation placed Canada near the bottom of the heap — at 14th. The report said that while scientific output is strong and internationally respected, “Canada does not take the steps that other countries take to ensure science can be successfully commercialized and used as a source of advantage for innovative companies seeking global market share. Canadian companies are thus rarely at the leading edge of new technology and too often find themselves a generation or more behind the productivity growth achieved by global industry leaders.” Not only that, but while the scientific research on water is ripe for commercialization and the need for innovation is clear, the path to the market is not straightforward, says Bernadette Conant, executive director of the Canadian Water Network in Waterloo, Ont., which seeks to ensure that science shapes the water-management innovations that draw investments. Some of the advances that could help instead fall into a political vacuum. “The needs are clear,” says Conant. “What we lack is a single or clear clientapproval process.” And, in a trend Molloy sees as dangerous, more and more universities are shying away from available market mechanisms in favour of waiting for industry to front the cash. “I’d like to see it go the other way,” he says. An early triumph for Molloy’s group is a process developed by Stephen Brown from Queen’s Department of Chemistry and Peter Aston from the university’s Department of Biomedical and Molecular Sciences. They figured

out how to find E. coli and other disease-causing organisms in drinking water more quickly and reliably. Brown had been working on using fibre-optic sensors to detect aromatic compounds as part of a study of the impacts of contaminants on fish. By optimizing the fibre-optic sensors to detect aromatic metabolites of E. coli they were able to detect it and other coliform bacteria. Previously, those pathogens would have been detected by a lab technician performing a visual interpretation of samples. Brown and Aston’s automated test is not only faster and more accurate, but also works in highly coloured or

Many of the great Canadian­solutions to water issues stay locked away in labs, never making­it to the market. opaque samples. They were galvanized by the Walkerton, Ont., tragedy of May 2000 in which seven people died and thousands fell ill from the ­notorious bacteria. PARTEQ, which has about a dozen industry sponsors who pay to sit at the table and help decide what gets developed, helped license the Pathogen Detection Systems technology. It was eventually sold to the French multinational corporation Veolia, and spun off into its offshoot, ENDETEC. The new system is now being launched internationally and PARTEQ and the scientist inventors stand to make royalties once the upfront development costs are paid back.

One of the key organizations set up to commercialize academic inventions from all over the country is GreenCentre Canada, also based in Kingston. Established in 2009 with $22 million from the federal and Ontario governments, it aims to match start-up investment money with clean, energyefficient chemical processes — known as green chemistry. It does that both by buying licences to the technology and selling them to industry, and by creating new companies to house the innovations. “The idea is to get it beyond: ‘Gee, isn’t it a great idea!’ ” says Rui Resendes, its executive director. Resendes says in the three years since GreenCentre began, there’s been a spike in interest and investment around the world in Canadian inventions. “Water has become the new currency,” he says. He points to an invention by Rob Singer, a professor of chemistry at the Maritimes Centre for Green Chemistry at Saint Mary’s University in Halifax, which is still at the laboratory stage but has immense potential for commercialization. GreenCentre has done a market assessment and wants to license the invention with a consortium of industry partners. It involves low-temperature ionic liquids, meaning salts that are liquid at or below room temperature. These have unique chemical properties, Singer says, because they attract metals and don’t evaporate as easily as other solvents do. That means they can grab onto metals in water but not evaporate into the atmosphere. And in turn that means they can decontaminate water of metals, keep them from polluting the atmosphere and allow the metals to be harvested for reuse. It’s a blue benefit on all fronts.

July | August 2012 CAnadian Chemical News   25


Conceptually, the ionic liquids could replace toxic solvents in hydrometallurgical metal refining, suck the valuable metals out of discarded electronics for resale and even clean up tailings ponds. Singer is still trying to figure out how toxic the ionic liquids are over time and is focusing research on making them both non-toxic and biodegradable. Perhaps the most famous recent success story is an invention by Don Mavinic, a civil engineer at the University of British Columbia in Vancouver, who figured out how to mine phosphorus from liquid sewage. Phosphorus is a precious element, mined in only five places in the world and poised to run out in a century. It is also crucial to feeding the global population because it stimulates plant growth, whether on land or in water. Left in wastewater, it can run into coastal waters and cause destructive algae blooms and low-oxygen zones as phytoplankton convert it to food. Mavinic figured out how to cause a chemical reaction in liquid sewage to extract most of the phosphorus and turn it into environmentally friendly, slow-release fertilizer. The process — which combines a nutrient rich feed stream with magnesium chloride and sodium hydroxide in a fluidized bed to precipitate struvite (MgNH4PO4.6H2O) in very pure crystalline pellets — is patented, licensed and managed out of the Vancouver company, Ostara Nutrient Recovery Technologies. It’s in use at Edmonton’s Gold Bar wastewater treatment plant, in Portland, Oregon, and in Virginia and Pennsylvania, and is being tested in Europe. The fertilizer is used in horticulture and on turf, marketed as CrystalGreen.

26  CAnadian Chemical News

“We see ourselves as a fertilizer company,” says Ahren Britton, Ostara’s chief technology officer, who helped develop the idea as a grad student of Mavinic’s in 2000. “We just happen to mine from wastewater instead of the ground.” Britton says the company reckons there are 200 to 300 plants in North America that could use the system to treat sewage and as many in Europe. China and Southeast Asia are also prospects. Ostara believes it will eventually mine as much as one million tonnes of fertilizer a year, reducing the amount needed to be taken out of the ground. Ostara, which has grown to 35 staff

“Water has become the new currency.” from just three in 2006, has won awards as a clean technology pioneer and was invited to the World Economic Forum in Davos, Switzerland, last year. The innovations aren’t only chemical, though; nor do they relate only to water quality. One of the globally significant water inventions under development in Canada is a project to harness tidal power in the Bay of Fundy. It’s a collaboration among academic and government scientists and industry, including Nova Scotia-based companies Nova Scotia Power, Minas Basin Pulp and Power, and Fundy Tidal; French company Alstom and U.K. company Atlantis Resources. The Bay is considered the prime site in the world for tidal speed and height, and the tidal power would replace some of the coal-fired electricity Nova Scotia uses now. It’s one of just two massive commercial tidal power turbines being developed

July | August 2012

in the world, along with another in the Orkneys in Scotland. A test turbine the size of a house went into the Bay’s Minas Basin in November 2009 and came out 13 months later, likely failing in the first few weeks because of the ferocious flow, says Anna Redden, a biologist with the newly launched Acadia Tidal Energy Institute and director of the Fundy Ocean Research Centre for Energy. Now, four sets of cables are going down in the Bay so that energy from four new test devices can feed straight to transmission lines this year. Redden says there are still unknowns about the direct effects on the environment and wildlife, but she’s helping design tests to figure that out. And although tidal power has gone in and out of vogue every few decades, Redden is sure it’s here to stay now. “I think we’ve come to the point where it’s never going away,” she says. “We have to harvest tidal energy.” While Redden and dozens of other academic scientists continue to piece together the complex puzzle of how to help society benefit from their water research, Conant of the Canadian Water Network has some provocative ideas about what the future will hold. Because water is integral to life and a shared commons, she posits that within a decade, patents and licences on water inventions may be passé. Instead, the new trend may be to break open the market, making patents openly accessible in the hopes that innovation will accelerate, and the Ivory Tower will be an even nimbler and more powerful driver of the Blue Economy. This story originally appeared in the September­ 2011 issue of Corporate Knights. Alanna Mitchell is an award winning freelance science writer. She is based in Toronto.


Society news | News from the Chemical Institute of Canada and its three Constituent Societies Conferences

Grapevine

Save the Date

André Bandrauk, chemistry profes-

August 28-30, 2012

sor at Université de Sherbrooke was

Oilsands 2012 Conference

named Officer of the Order of Canada

Edmonton, Alta.

on May 25, 2012. The honour was

www.ualberta.ca/OILSANDS2012

awarded for his groundbreaking work October 10-12, 2012

lecular photonics. He is a pioneer of

Pacific Rim Summit on Industrial

attosecond science - the time scale of

Biotechnology & Bioenergy

electron movement - and is currently

Vancouver, B.C.

researching laser control of electrons

www.bio.org/events

for future applications in chemistry, biology and even quantum informatics.

October 14-17, 2012 62nd Canadian Chemical Engineering

Terry McMahon was reappointed the

Conference (CSChE 2012)

University of Waterloo’s dean of science.

Vancouver, B.C.

Previously, McMahon had been a profes-

www.csche2012.ca

sor of chemistry at the University of New Brunswick and the University of Water-

October 26, 2012

loo, the director of the Guelph-Waterloo

24e Colloque Annuel de Chimie

Centre for Graduate Work in Chemistry

Sherbrooke, Que.

and Biochemistry and the chair of Wa-

www.pages.usherbrooke.ca/colloque-chimie

terloo’s department of chemistry. He

Over the course of four sunny days in Calgary this May, some 2,280 delegates gathered at the 95th ­Canadian Chemistry ­Conference and Exhibition. Above, panelists provide their insights on careers in industry for chemistry graduates at the CIC Chair’s Event (top). Simon Fraser University graduate student, Danielle Wilson, presents her poster at the evening reception. She won 1st place in the Materials Chemistry Division poster competition. The ­conference ­featured 582 posters and just over 1400 talks. For more from the ­Calgary ­conference, go to accn.ca/societynews

In Memoriam

The CIC wishes to extend its condolences to the families of W.M. Osborne, MCIC and T.L. Stubbs, MCIC.

was first appointed Waterloo’s dean of

May 27-29, 2013

science in 2007.

3rd Climate Change Technology ­Conference Montreal, Que.

Sudhir Abhyankar assumed the role of

www.cctc2013.ca

president of College Chemistry Canada (C3) in May. C3 is a non-profit organiza-

June 15-19, 2013

tion dedicated to excellence in chemis-

World Congress on Industrial ­Biotechnology

try education. Abhyankar is associate

& Bioprocessing

professor of chemistry and environmen-

Montreal, Que.

tal science at Memorial University’s

www.bio.org/events

Grenfell campus. August 18-23, 2013 Marie D’Iorio was named the new Ex-

9th World Congress of Chemical ­Engineering

ecutive Director of the National Institute

(WCCE9)

for Nanotechnology (NINT) on May 31,

Coex, Seoul, Korea

2012. D’Iorio is a physicist and expert in

www.wcce9.org

nano-electronics. NINT, founded in 2001, is a national research and technology development organization based in Alberta. To read more from the Grapevine go to accn.ca/societynews.

Find more news from the CIC at accn.ca/societynews. Is there something going on that you think we should write about in this section? Write to us at magazine@accn.ca and use the subject heading “Society News.”

28  CAnadian Chemical News

july | August 2012

Susie riegel (both)

in computational chemistry and mo-


Society news jOURNALS

Things to Know The CIC will now be providing video recordings of key presentations from our annual chemistry and chemical engineering­conferences. Recordings from this year’s Canadian Chemistry Conference and Exhibition in Calgary, Alta., can be viewed at http://cic.sclivelearningcenter.com The CIC launched a new monthly electronic newsletter in June that includes news about our societies’ activities­, career resources, updates from industry, trends in technology and international news. If you didn’t receive the newsletter and would like to be on the mailing list, send your email address to info@cheminst.ca with the subject line “send me the newsletter.” The program for the 62nd Canadian Chemical Engineering Conference in Vancouver, October 14-17, 2012, will be available on August 1 at www.csche2012.ca. cic members are invited to participate in a survey being conducted by the Canadian National Institute for the

Engineering Journal Jumps Up The Canadian Journal of Chemical Engineering is growing; Beginning January 2013, it will be published 12 times yearly instead of its current six, with 2,000 pages annually up from 1,200. A hike in the number of papers being submitted— the editors now get over 500 papers every year — and a desire to reduce publication time for the printed version are what sparked the change. “Online publication times are quite good now,” says editor-in-chief Joao Soares, “But it is taking too long to get in print.” There is also a backlog of articles accepted for publication but delayed for printing because of the current space limitation. A faster publishing time will mean the editors can invite more authors to submit papers and still efficiently handle the extra volume. “This will attract better papers and increase the impact factor of the journal,” says Soares. “This is a major, positive milestone.”  products + Services

Blind that seeks to better understand the incidence and nature of laboratory eye injuries in Canada. It is hoped that the information gained will help inform an awareness campaign and advocacy in order to minimize vision loss from chemical accidents in the laboratory. The survey can be accessed at www.surveymonkey.com/s/chemicaleyeinjury The International Union of Pure and Applied Chemistry (IUPAC) is seeking Canadians involved in the chemical sciences to serve as officers and committee members. These positions would encompass a two- to four-year term beginning in 2014. Interested and qualified individuals are asked to submit their curriculum vitae to the Canadian National Committee (CNC) for IUPAC no later than July 17, 2012. More information and a list of open positions can be found at www.iupac.org. The deadline for applications for the 2013 CNC/IUPAC Travel Awards is October 15, 2012. These awards are to help young Canadian scientists and engineers, who should be within 10 years of having earned their PhD, to present a paper at an IUPAC-sponsored conference outside Canada and the U.S.A. Find out more at www.cnc-iupac.ca/awards_e.html.

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Chemfusion

How beta blockers broke new ground

A

nyone who has had cardiac or hypertension issues is familiar with beta blockers, but less well known is the milestone they represent in pharmaceutical history. Beta blockers were the first class of drugs to be rationally designed based on molecular structure. Previously drugs came to light more or less through accidental discoveries. So what exactly do these drugs block? Beta blockers constitute one of the most important classes of medications because of their ability to block the action of noradrenalin or adrenalin, also referred to as norepinephrine and epinephrine. These two compounds play a critical role in controlling how our heart beats and how our lungs function. In the case of the heart, they stimulate the smooth muscle contractions that cause the heart to beat, while in the lungs they stimulate activity to relax the muscles that surround airways. Blocking the action of noradrenalin and adrenalin would therefore be expected to reduce the workload of the heart, but at the same time it would lead to the constriction of airways. Reducing the workload of the heart is advantageous after a heart attack, as well as when there is a need to control high blood pressure or an irregular heart beat. The pharmaceutical challenge is to block the stimulating effect on the heart without interfering with breathing. That is just what beta blockers can do. But how? Both norepinephrine and epinephrine are synthesized in the body from tyrosine, a commonly occurring amino acid in our food supply. They are termed ‘neurotransmitters’ because they are intimately involved in how messages

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get transmitted from one nerve cell to another. Noradrenalin and adrenalin exert their effects through the involuntary or autonomic nervous system, a network of nerves that govern body functions such as breathing and cardiac activity. We don’t have to think about making our heart beat, so the action is appropriately called ‘autonomic’, as opposed to walking or talking, activities that are controlled by the voluntary nervous system. That part of the nervous system uses acetylcholine as its prime neurotransmitter. Neurotransmitters are stored inside nerve cells and are released into the gap that separates nerve cells, known as the synapse. They then migrate towards neighbouring nerve cells where they can fit into receptors stimulating an electrical message to be sent down that nerve cell. This in turn triggers the release of neurotransmitters into the next synapse which then stimulate receptors in an adjacent nerve cell and so it goes on and on. Receptors are actually protein molecules that are configured in a specific shape to match the molecular structure of the neurotransmitter, much like a lock is designed to accept a key. But in the case of noradrenalin and adrenalin, the key can fit into two slightly different locks. Alpha receptors are the ones that cause relaxation of smooth muscles around bronchial tubes when stimulated, while stimulation of beta receptors increases heart activity. As the name implies, beta blockers can specifically block beta receptors without interfering with lung function. How they do this

july | August 2012

By Joe Schwarcz

comes down to the nuances of molecular structure. Morphine, digitalis, penicillin, nitrous oxide and even aspirin are classic examples of drugs that were “discovered.” Aspirin, for instance, is a synthetic modification of salicylic acid, a compound that occurs in nature. It would never have been made were it not for the empirical observation that an extract of willow bark was effective against pain. Beta blockers, on the other hand, were specifically designed to have molecular structures similar enough to noradrenalin and adrenalin to fit into receptors, but different enough not to stimulate these receptors. Sort of like having a key that fits a lock but doesn’t open it while preventing other keys from being inserted. By the 1950s researchers had shown that noradrenalin and adrenalin were neurotransmitters synthesized in the body and that they could stimulate two types of receptors which had been termed ‘alpha’ and ‘beta.’ Scottish pharmacologist James Black working for ICI Pharmaceuticals in Britain took on the challenge of constructing molecules that would preferentially block beta receptors. In 1962 he came up with propranolol (Inderal), the first clinically successful beta blocker. It has since been joined by an array of more refined, selective beta blockers but the planned synthesis of propranolol based on the structure of specific neurotransmitters represents the turning point between drug discovery and drug design. Joe Schwarcz is the director of McGill University’s Office for Science and Society. Read his blog at chemicallyspeaking.com.


62nd Canadian Chemical Engineering Conference

VAncouver British Columbia, Canada

October 14–17, 2012 Energy, Environment and Sustainability

www.csche2012.ca



ACCN, the Canadian Chemical News: July + August 2012