Apr 2004: ACCN, the Canadian Chemical News by Chemical Institute of Canada

L’Actualité chimique Chemical News Canadian

canadienne

April Avril

2004 Vol. 56, No./no 4

Advances in Green Chemistry and Engineering Pulp and Paper Pollution Prevention Success Stories … and more!

L’Actualité chimique canadienne

Canadian Chemical News

April Avril

2004 Vol. 56, No./no 4

Table of contents Table des matières

A publication of the CIC Une publication de l’ICC

Page 18

Page 20

• Guest Column/Chroniqueur invité Green Chemistry and Engineering Forum P. Sundararajan, FCIC

Page 30

Feature Articles/Articles de fond Waste Not—Want Not?

• Personals/Personalités

• News Briefs/Nouvelles en bref

• Chemputing Out-of-this-world Chemistry Marvin D. Silbert, FCIC

• Chemfusion Writing the Book—on Paper Joe Schwarcz, MCIC

• Chemical Shifts

Green chemistry’s current trends and future aspirations Chao-Jun Li, MCIC

Innovation Roadmap

Canada’s bioproducts industry’s report on bio-based feedstocks fuels, and industrial products J. E. Cunningham

Meet the Green Machines

What’s new? Who’s who? What’re they up to?

Developing Green Chemistry

Organometallic reactions in water and other alternative media

• CIC Bulletin ICC

• CSC Bulletin SCC

• CSChE Bulletin SCGCh

Tak Hang Chan, FCIC

Directed Evolution of Enzymes

Obtaining clean, efficient, and biodegradable catalysts Nicolas Doucet and Joelle N. Pelletier, MCIC

• Local Section News/ Nouvelles des sections locales

• Division News/Nouvelles des divisions

• Student News/Nouvelles des étudiants

• Careers/Carrières

You Get What You Pay For!

Energy supply and pricing for a sustainable future William E. Rees

New and (Already) Improved!

A report on the first IUPAC International Conference on Bio-based Polymers (ICBP 2003) Cover/Couverture What does it mean to be “green”? The field of green chemistry has diversified in widespread and progressive directions for the benefit of the economy and the environment. Canada and the world take note! Photo by Crissie Hardy

Robert H. Marchessault, FCIC, and Jumpei Kawada, MCIC

New Bleaching Agents for Mechanical Pulps

A discovery made possible by the pursuit of green chemistry Thomas Q. Hu, MCIC, and Brian R. James, FCIC

Pollution Prevention In the print and pulp and paper industries

Guest Column Chroniqueur invité Section head

Green Chemistry and Engineering Forum When it comes to waste production— prevention is better than a cure he Board of Directors of the Chemical Institute of Canada has recently created a Green Chemistry and Engineering Forum as part of the CIC’s new initiatives. As the national organization representing chemical professionals in Canada, it is essential that the CIC initiate and participate in activities related to green chemistry and engineering. This strategically places the CIC in its efforts in lobbying, taking public positions on issues, and communicating with the public. The green chemistry and engineering initiative has surged in various forms throughout the world during the past decade. The Green Chemistry Institute (GCI) is now a part of the American Chemical Society (ACS) and has chapters throughout the world. A Canadian Green Chemistry Institute Chapter (22nd) was formed in 2002 by a group of interested chemists and chemical engineers in academia, industry, and government laboratories in Canada. Its mission, activities, and other details are available at www.greenchemistry.ca. The basic premise of “Green Chemistry and Engineering” is that chemical processes should be developed to enable zero waste production, and that prevention is better than a cure. Research should be encouraged at the fundamental level to reach this goal. There have been several reviews recently on concepts such as “atom economy” (B. M. Trost, Acc. Chem Res. 35, 695. 2002), which simply means that all the material that is used to produce a product should be incorporated in the final product so that “no atom is wasted.” Green chemistry and engineering may be defined as the utilization of a set of 12 principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture, and applications of chemical products (Anastas, P.; Warner, J. Green Chemistry: Theory and

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

P. Sundararajan, FCIC

Practice, Oxford University Press: Oxford, 1998). Consequently, green chemistry focuses on the fundamentals of chemical research. It is interesting to note that a fourth-year level course is offered at McGill University on green chemistry (course 180–462A). As J. McKee, editor of Physics in Canada, noted (Physics in Canada, 59, 302, 2003), whatever role science may play in the creation of environmental problems, it is through science and engineering that green solutions to such problems can be achieved. While countries around the world are taking steps to curb the “throw away culture” of the plastics world (C&ENews, October 27, 2003, p. 28; Physics in Canada, 59, 302, 2003), the technology is also gearing up to devise “ever green plastics” (Nature, 426, 424, 2003). A proposal was made last year for the CIC to take a proactive role and participate in the activities related to green chemistry. Since the green chemistry and engineering (GCE) initiative is a “culture” and a “business practice,” it impacts all sub-disciplines of chemistry and chemical engineering. It was hence decided by the CIC Board that instead of forming a Division, we would create a Green Chemistry and Engineering Forum (GCEF), based on the model used by the American Physical Society for common themes of this nature. Any member of the CIC can take part in the activities of this Forum without any additional fee. Canada’s vast forest and agricultural resources coupled with its strong positioning in chemical and biological sciences and engineering, give us a green advantage to advance in this important area of worldwide growth. The GCEF plans to organize interdisciplinary discussion events related to GCE during the annual conferences. Of course, suggestions from members are welcome.

P. Sundararajan, FCIC, is the vice-chair of the CIC and is an NSERC-Xerox Industrial Research Chair and professor of chemistry at Carleton University, Ottawa, ON.

avril 2004

Publications Assistant/Adjoint aux publications Jim Bagrowicz Graphic Designer/Infographiste Krista Leroux Editorial Board/Conseil de la rédaction Terrance Rummery, FCIC, Chair/Président Catherine A. Cardy, MCIC Cathleen Crudden, MCIC Milena Sejnoha, MCIC Editorial Office/Bureau de la rédaction 130, rue Slater Street, Suite/bureau 550 Ottawa, ON K1P 6E2 613-232-6252 • Fax/Téléc. 613-232-5862 editorial@accn.ca • www.accn.ca Advertising/Publicité advertising@accn.ca Subscription Rates/Tarifs d’abonnement Non CIC members/Non-membres de l’ICC : in/au Canada CAN$50; outside/à l’extérieur du Canada CAN$75 or/ou US$60. Single copy/Un exemplaire CAN$8. Canadian Chemical New/L’Actualité chimique Canadienne (ACCN) is published 10 times a year by The Chemical Institute of Canada / est publié 10 fois par année par l’Institut de chimie du Canada. www.cheminst.ca Recommended by The Chemical Institute of Canada, The Canadian Society for Chemistry, the Canadian Society for Chemical Engineering, and the Canadian Society for Chemical Technology. Views expressed do not necessarily represent the official position of the Institute, or of the societies that recommend the magazine. Translation of any article into the other official language available upon request. / Recommandé par l’Institut de chimie du Canada, la Société canadienne de chimie, la Société canadienne de génie chimique et la Société canadienne de technologie chimique. Les opinions exprimées ne reflètent pas nécessairement la position officielle de l’Institut ou des sociétés constituantes qui soutiennent la revue. La traduction de tous les articles dans l’autre langue officielle est disponible sur demande. Change of Address/Changement d’adresse circulation@cheminst.ca Printed in Canada by Gilmore Printing Services Inc. and postage paid in Ottawa, ON./ Imprimé au Canada par Gilmore Printing Services Inc. et port payé à Ottawa, ON. Publications Mail Agreement Number/ No de convention de la Poste-publications : 40021620. (USPS# 0007-718) Indexed in the Canadian Business Index and available on-line in the Canadian Business and Current Affairs database. / Répertorié dans la Canadian Business Index et à votre disposition sur ligne dans la banque de données Canadian Business and Current Affairs. ISSN 0823-5228

Personals Personnalités Section head

Industry The Pulp and Paper Technical Association of Canada (PAPTAC) awarded the John S. Bates Memorial Gold Medal to Charles A. Sankey, FCIC, in recognition of his long-term contributions to the science and technology of the industry. Sankey’s career has spanned four decades and much of his work was dedicated to the development of the process for extracting vanillin and other valuable chemicals from sulphite liquor. Commercialization of these processes has created an economic benefit in useful by-products, and in alleviating effluent problems. PAPTAC recognized Bernard Bégin, ACIC, for his contribution to a paper entitled, “Effects of Wood and Pulp Quality on Linting Propensity.” The paper was a joint effort and awarded the I. H. Weldon Award. PAPTAC awarded the Douglas Atak Award to Yonghao Ni, MCIC, and Zhibin He of the University of New Brunswick, and Eric Zhang of Holmen Paper AB of Sweden. Their paper was entitled, “Mechanism of Sodium Borohydride-Assisted Peroxide Bleaching of Mechanical Pulp (The PR Process),” and was deemed the best paper presented at the mechanical pulping sessions of the previous PAPTAC Annual Meeting.

University Second-year Simon Fraser University science student, Karen Chan, won a prestigious Women in Engineering and Science (WES) award. Although always inclined towards “medicine and mathematics,” Chan says her decision to study science “was kind of arbitrary.” An accomplished pianist with a passion for drama

Distinction

Jean Lessard, FCIC

Karen Chan

and literature, the 19-year-old Vancouver native also entertained the idea of enrolling in an arts program. But last month, the second-year chemical physics student received news that confirmed she’d made the right decision: Chan was named a 2004 winner of the prestigious WES competition. There are 25 presented each year in recognition of the research potential of outstanding young Canadian female scientists. The honour affords winners the opportunity to work for several terms at national research institutes, for which they are paid up to a total of $33,000. This fall, Chan hopes to study nanoscience during a workterm at Montréal’s Industrial Materials Institute. It will not be her first time working in a lab: currently, she receives funding from the Natural Sciences and Engineering Research Council (NSERC) to assist SFU professor Zuo-Guang Ye, MCIC, in his solid state chemistry research. Chan appreciates that SFU’s relatively small size offers her “so much more direct contact with professors.” She says she has been given research opportunities much earlier than students at other larger campuses.

“Working as an NSERC student has really inspired me,” says Chan. “In school, you’re chasing after the ‘right’ answer. But in the research lab, there are a lot more possibilities. You get to ask more questions and be more creative. It’s satisfying to know that one day you may be able to contribute to the broader body of knowledge.” Although Chan has not yet clearly identified her career goals, she thinks it would be “very gratifying” to work as a researcher, and to “make an impact on human health” through biomedicine. She says the biggest challenge ahead will be focusing her area of interest. “At the moment, I’m into nanoscience, but I’m also interested in inorganic chemistry and physics. I’m considering all the possibilities.” She laughs: “I’m open to inspirational professors.” Reprinted with permission from Simon Fraser University

Pioneer of electrocatalytic hydrogenation (ECH) in Canada, Jean Lessard, FCIC, of the Université de Sherbrooke received the 2004 Murray Raney Award from the Organic Reactions Catalysis Society (ORC Society). The Raney Award is sponsored by W.R. Grace Co. and administered by the ORC Society. It is given to an individual who has made significant technical contributions to chemistry and the chemical industry via catalyst technology based on that originally developed by Murray Raney. This international prestigious prize, awarded every two years, is given to Lessard in recognition of his substantial contributions to the use of Raney type metals and to the understanding of factors which control their reactivity and the selectivity of the ECH of organic polyfunctional compounds. Lessard just recently presented his award address to the ORCS at the 20th Conference on Catalysis of Organic Reactions at Hilton Head Island, SC.

In Memoriam The CIC extends its condolences to the families of: Stanley Bywater, FCIC Frederick R. Richardson, MCIC Stuart M. Chapman, FCIC Walter R. Ruston, MCIC Dimitrio V. Favis, FCIC

April 2004

Canadian Chemical News 3

News Briefs Nouvelles en bref Section head

Shell Gets Nod U.S. Border For New Mine Concerns Keep Shell Canada has received Researchers conditional approval for Phase 1 of its Jackpine Mine from a joint Home

review panel established by the Alberta Energy and Utilities Board and the federal government. The Jackpine Mine, a second oil sands mine for Shell in the Athabasca oil sands region, was found to be in the public interest and unlikely to result in significant adverse environmental effects. The application is subject to 19 conditions and now has to be approved by the cabinets of both the provincial and federal governments. “This is a big step forward towards our long-term growth goal of producing 500,000 barrels/day from our Athabasca oil sands leases,” says Neil Camarta, senior VP, oil sands. The development consists of: • Expansion of the existing Muskeg River Mine to increase total production from the current design level of 155,000 barrels per day of bitumen up to approximately 225,000 barrels per day. This project would likely be completed before 2010; • A new stand-alone mining and extraction facility located on the eastern portion of lease 13 with a capacity of approximately 200,000 barrels/day of bitumen; • Mining of additional resources on leases 88 and 89 as an extension of the first phase of the Jackpine Mine, allowing for additional production of approximately 100,000 barrels per day. Shell is also looking at the integration of each of these mining developments with upgrading facilities. The exact timing of any of these developments will depend on a number of factors, including the outcome of the regulatory processes, project economics, and the ability to meet Shell’s sustainable development principles. Camford Chemical Report

Increased concerns about border security prevented two Chinese-born graduate students from presenting papers in the U.S. recently, an issue that has University of Toronto administrators ready to take action. The two environmental toxicology students, Yushan Su and Hang Xiao, were slated to make presentations about the movement of pollutant chemicals in the environment to their colleagues at the annual meeting of the Society of Environmental Toxicology and Chemistry, being held in Houston, TX. They applied early for visas, booked their hotel, purchased airplane tickets and prepared their posters and presentations. It was then the environmental toxicology students hit a brick wall at the U.S. consulate—the term toxicology was a red flag to consular officials. Su and Xiao were refused visas and told they would have to undergo background checks because officials were concerned they worked with toxic chemicals. A letter from the society’s president explaining the conference and its value in shaping U.S. public policy made no difference. The delay forced Su and Xiao to abandon their plans and to absorb more than $1,000 in registration fees

Ottawa Seeks Submissions for CO2 Projects A two-year initiative is expected to help develop a market for carbon dioxide capture and storage in Canada, as well as new uses

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and flight and accommodations costs. “We were surprised,” said the students’ supervisor, U of T chemistry professor, Frank Wania. “Both had been to the same meeting the year before and followed the very same procedures and there were no problems at all.” Faculty members from chemical engineering and chemistry were outraged by the incident, which impeded the flow of ideas across the border. Both department chairs were angry enough to fire off a memo to administrators seeking university action. “This is about free trade in the intellectual realms and I think that is extremely important,” said Douglas Reeve, FCIC, chair of chemical engineering and applied chemistry, and the Frank Dottori, professor of pulp and paper engineering. “I think it is extremely important to Canadian researchers in science and engineering that we should be able to have ready access to the American market and the American scene. We are also able to make significant contributions to the American scene and economy.” Scott Mabury, MCIC, chair of chemistry at U of T, said educating consular officials might make a difference. “I think it’s an individual thing down there on University Avenue (at the U.S. consulate),” he said. “I think it’s a real practical issue of border officials making fairly rash decisions without any knowledge about their impact on a career or

certainly on the freedom of inquiry aspect. “If we ignore it, it could spiral downward and next, it’s any physics students working with lasers—I mean, this could go anywhere. It’s not country based, it’s subject based, and subjects can drastically broaden.” Vivek Goel, deputy provost and vice-provost (faculty), understands the implications the border difficulties have, not only for the free flow of information but for the careers of aspiring scientists. “It’s something that’s affecting scholarship,” he said. “In a lot of disciplines people have to be present at these key North American meetings and they’re not able to do it, so it’s affecting people’s ability to explore questions they’re interested in. For junior faculty that really impacts on their progress because they need to get international recognition for their scholarship and in a lot of disciplines, many of the international meetings will be in the U.S.” Goel said the University of Toronto will be pursuing the issue with the U.S. government. “The president is planning to meet with U.S. officials to discuss visa and related issues. We hope we can convey an understanding of our concerns,” he said. “However, we recognize that the U.S. government’s security concerns are paramount and that their rights under international law must be respected.”

for CO2 from industrial emitters. Developed in consultation with industry and provinces in western Canada, this initiative complements provincial measures such as Alberta’s CO2 projects royalty credit program and is designed to reduce duplication of effort for applicants in the Alberta program. The Western Canada Sedimentary Basin is believed to be

the most promising location for such projects. “Storing CO2 in an innovative way will bring us closer to meeting our goals for reducing greenhouse gas (GHG) emissions and contributing to climate change solutions,” says R. John Efford, Minister of Natural Resources Canada (NRCan). “These projects will also help us maximize the benefits from our fossil fuel resources.”

Reprinted with permission from the University of Toronto Bulletin.

News Briefs Nouvelles en bref Section head

forest managers in late-2004. Even after testing is complete and the tool is released, the carbon accounting team will continue to update it as science and accounting rules evolve. Information on carbon accounting programs is available at: carbon.cfs.nrcan.gc.ca. The operational carbon-accounting tool tracks and predicts changing carbon stores in Canada’s forests.

Tracking carbon in Canada’s forests moved one step closer to reality this fall. Thirty analystsand partners from Canada’s Model Forest Network put Canada’s first operational level carbonaccounting tool through its paces. The tool, developed in partnership by the Canadian Forest Service’s carbon accounting team and the Model Forest Network, allows forest managers to assess how harvesting, thinning and planting trees, as well as disturbances due to fire, disease or insect infestation, contribute to changes in forest carbon stocks. The tool tracks carbon stored in the trees, leaf litter, woody debris, and soil that make up forest ecosystems. It can be used to analyze how past management decisions and forest disturbances have affected today’s carbon levels, and to predict how today’s forestmanagement decisions will impact future carbon stocks.

“Forest managers are increasingly being asked to understand and evaluate the consequences of their management actions in terms of their impacts on the atmosphere,” says Werner Kurz, senior research scientist at the Canadian Forest Service, Pacific Forestry Centre, and a leader of the carbon accounting team. “Trees are 50 percent carbon. As we grow or harvest trees, we either take up carbon from the atmosphere or release it back into the atmosphere. The effects we have on carbon levels in the atmosphere can be substantial.” The tool that measures such changes builds upon a decade of work by scientists at the Canadian Forest Service to develop a carbon budget model for research purposes. With policy-makers, trading partners and the public pressuring the forest industry to answer for how its activities affect global climate, the carbon accounting team and its Model Forest partners are now applying the research model to forest operations, thus allowing managers to include carbon as one of the criteria in the planning process. The team had to be sure the tool could incorporate the best available science about forest-

carbon stocks and processes as it becomes known, and comply with evolving international carbon-accounting rules. The scientists had to design it to be flexible to deal with the many scenarios and management questions that interest forest managers, and to address regional differences in climate and environmental conditions. It also had to be compatible with different inventory formats. “The message we received from different participants is, ‘You have to make it easy for us to use this.’” Kurz says. “The way to make it easy for them is by permitting them to build, to the greatest extent possible, on the data and data sources that they already have for other types of analysis. They’ve already done the hard part: getting the inventory, keeping it current, having the growth and yield data for each of the different strata within the inventory. We wanted to built on that.” “We look forward to the coming year when our partners begin to incorporate insights gained by using the model in sustainable forest management plans and practices,” says Jim Taylor, general manager of the Western Newfoundland Model Forest, one of the sites involved in the workshop. “There is a growing desire to understand the role of carbon as it relates to the practices of forest management.” The carbon-accounting operational tool will be available, free of charge, for use by provincial, territorial, industrial and private

Incentive funding will be used to support projects that demonstrate CO2-based enhanced resource recovery in small-scale commercial settings, and to help abate the costs of CO2 capture and storage. CO2 is collected during processes such as oil sands recovery, electricity generation and cement, petrochemical and fertilizer production. The captured CO2 can then be

processed, compressed, transported and injected into geological sites, such as oil and natural gas reservoirs, deep coal beds, or deep saline aquifers. Potential applicants for this incentive include any for-profit firm that will operate a project that injects CO2 from a Canadian industrial source into a geological formation for storage, enhanced oil and gas recovery or disposal

in Canada. Applicants must submit detailed economic data for the project. Only eligible recipients who sign contribution agreements with NRCan will receive incentive payments. This $15 million investment in CO2 capture and storage offers Canada significant longterm potential for addressing GHG emissions, while continuing the pursuit of our industrial

economic objectives. This initiative builds on the unique expertise Canada has developed from the Weyburn CO2 monitoring project.

Forest Managers Test Carbon Tracker

April 2004

Information Forestry, Canadian Forest Service, Pacific Forestry Centre

CFI Funds Research at SFU—and Beyond Canada’s research community will receive a major boost thanks to the $585.9 million investment from the Canada Foundation for Innovation (CFI). The money is intended to support 126 projects at 57 Canadian universities, colleges, hospitals and other non-profit research institutions. The CFI award to Simon Fraser University worth $9.5 million is the largest single grant ever received by SFU. It will help to fund a new centre for research in electronic materials at Simon Fraser University as well as SFU’s component of a regional laser facility. The $7.34 million has been awarded for the new centre, and

Camford Chemical Report

Canadian Chemical News 5

News Briefs Nouvelles en bref Section head

the remainder has been assigned to the University of British Columbia for a regional laser facility, called the Laboratory for Advanced Spectroscopy and Imaging Research (LASIR). “This award builds on SFU’s core strengths in material science and will enable our researchers to engage in truly transformative research in this very important field,” says Bruce Clayman, SFU vice-president, research. SFU’s share of the LASIR CFI award will pay for state-of-the-art laser equipment and the space to house it at SFU. Gary Leach, MCIC, the SFU chemistry professor who co-wrote the application for the LASIR award with SFU and UBC colleagues, says the joint facility will enable national and international researchers in academia and industry to pursue new science, including new frontiers in laser chemistry and spectroscopy, environmental science, materials chemistry and chemical and biological catalysis. Ross Hill, FCIC, past CSC treasurer, is currently a chemistry professor at SFU. He says that international researchers specializing in some of the newer forms of nanotechnology, such as molecular-based devices, will be coming to the centre. Simon Fraser University

Canada Commits $1.5 M to Great Lakes Cleanup The Honourable David Anderson, Minister of the Environment, announced funding of $1.5 million from the Great Lakes Sustainability Fund, to support 47 restoration projects in the Great Lakes Basin. The fund provides financial support to projects that improve the ecosystem health of Areas of Concern around the Great Lakes, which

CGPA Wants Change Canada’s generic pharmaceutical industry believes legislation reinstated in the House of Commons will not deliver Canadian-made generic drugs to people in developing countries. Since the introduction of Bill C-56 in November 2003, the Canadian Generic Pharmaceutical Association (CGPA) has consistently told Ottawa that the legislation needs major changes to be effective. Despite a January 23, 2004 letter to Prime Minister Paul Martin outlining obstacles to delivering on the bill’s intent, it was recently reinstated without amendment. “The government’s intention is laudable, but it is unlikely that any generic pharmaceutical company in Canada will use it unless substantial amendments are made,” says Jim Keon, president of the CGPA. “The government has allowed this landmark initiative to be hijacked by the multinational brand-name pharmaceutical industry.” The CGPA believes one of the most flawed sections of the bill is the provision that gives brandname drug makers a right of first refusal. This will allow brand-

have been identified as being environmentally degraded pursuant to the Canada–U.S. Great Lakes Water Quality Agreement. “Restoring the health and sustaining the integrity of the Great Lakes Basin Ecosystem is a priority for the Government of Canada, and we’re advancing through concrete action,” said Minister Anderson. “We must continue to protect and restore this precious resource, which serves as the primary source of drinking water for the millions of Canadians who live, work, and play in the Great Lakes Basin. Building on our success in the full restoration of Collingwood Harbour and Severn Sound, we’re working with our partners

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name drug makers 30 days to take over contracts already negotiated by generic companies. “The very existence of the right of first refusal will dissuade Canadian generic companies from pursuing agreements or bidding on contracts under this initiative. Generic drug companies will not invest time and millions of dollars if it could all be taken away,” notes Keon. Another industry concern is the restriction that the buyer must be a government, excluding non-governmental organizations that deliver health care in developing countries. The CGPA will seek substantial amendments to the legislation during the committee process. Camford Chemical Report

Canadian Subsidy Directory The new revised edition of the Canadian Subsidy Directory 2004 is now available. This publication contains descriptions of more than 2,600 direct and indirect financial subsidies, grants and loans offered by government departments and

toward ensuring a healthy and sustainable future for the Great Lakes.” Great Lakes Sustainability Fund projects, involving partnership with local government and community groups, focus on a range of restoration activities. These include improved practices in the treatment of wastewater by products, restoration of habitat for fish and wildlife, and preventing agricultural run-off from flowing into waterways that empty into the Great Lakes. The funding announced today is part of the Government of Canada’s Great Lakes Sustainability Fund, first announced by Minister Anderson

agencies, foundations, associations and organizations. The new edition is the most complete and affordable reference for anyone looking for financial support. It is deemed to be the perfect tool for new or existing businesses, individual ventures, foundations and associations. The Canadian Subsidy Directory is the most comprehensive tool to start a business, improve existent activities, set up a business plan, or obtain assistance from experts in fields such as: Industry, research and development, education, agriculture, communications, municipal infrastructure, the service sector, hi-tech industries, import-export, labour, and much more. It also offers assistance from and for foundations and associations, guidance to prepare a business plan, market surveys, and computers. The Canadian Subsidy Directory is sold for $69.95. To obtain your copy visit www.cbooks.biz. Canada Books

in July 2000. Through the fund, the Government of Canada is investing $30 million over five years to help restore the remaining Canadian Areas of Concern. This funding is a key component of the Government of Canada’s Great Lakes Basin 2020 Action Plan which is an inter governmental partnership between Health Canada, Fisheries and Oceans Canada, Canadian Heritage, Transport Canada, Natural Resources Canada, Agriculture and Agri-Food Canada, Public Works and Government Services Canada and Environment Canada. Environment Canada

Chemputing

Out-of-this-world Chemistry Marvin D. Silbert, FCIC here’s a new level of excitement on the Web. We can look at our computer monitors and watch an experimental program taking place on another planet. NASA have landed a pair of Rovers equipped with a collection of chemical instruments on two locations on the surface and the European Space Agency is orbiting the planet. We get to see all the new data as soon as it’s made available. The main sites are the Jet Propulsion Laboratory’s (JPL) Mars Rovers site (http://marsrovers.jpl.nasa.gov/home/index. html) and the European Space Agency’s (ESA) Mars Express site (http://www.esa.int/SPECIALS/Mars_ Express/). Both also give you several useful links. You can also find a vast collection of data and images from earlier visits on the Mars Pathfinder Project site (http://nssdc.gsfc.nasa.gov/planetary/mes ur.html). Whatever you do—have a good look at NASA’s compilation of images of all the planets and their satellites (http://pds.jpl.nasa.gov/planets/) plus some rather spectacular images from the Hubble space Telescope (http://heritage.stsci.edu/gallery/gallery. html). After you browse through these, you will probably toss out any old astronomy book that’s kicking around the house. The big search is for evidence that life may have existed on Mars. The Viking landers in 1976 included GC/MS equipment, but failed to come up with conclusive evidence for life. The Rovers are concentrating on searching for evidence that water is present now or was present in the past. You can’t have life as we know it, without water. If you find it, some form of life is or was possible. If you don’t find it, it’s unlikely that any form of life existed. Water, if it was present, should leave a geochemical trail. A mineral such as gypsum would have come into existence in an aqueous environment as would carbonate rocks. Mars is known as the red planet due to the presence of iron oxides, especially hematite. Another form of hematite, the grey hematite, can form in standing water where

it precipitates in layers. It can also form through volcanic activity. The crystalline forms will be different. The Rover, Opportunity, landed in an area where there is an abundance of hematite. It’s going to look at the crystal form and also look for other species. If it finds the layered hematite along with any carbonate species, we’ll know that water had been there. In the quest for water, there are two sets of tools. First, there is photographic evidence. The Rovers send them from the surface every day. The Mars Express sends them less frequently from orbit. As they arrive, the geologists jump into action and try to identify the land patterns which can be compared with those on earth where we know what happened. Those photos are on the website. They may be exciting, but just wait until you get to see the ones that are in 3D. These appear as two almost superimposed images, one with a preponderance of red tones and the others blue. To view them in 3D, you need a pair of glasses with a red left eye and a blue (NASA) or green (ESA) right eye. I know there’s a pair around the house, but they seemed to have disappeared. Fortunately I was on Highway 401 one day and remembered about EfsonScience (http://www.escience.ca/home.html) just a few blocks down from the Dufferin Street exit ramp. I got a red/blue pair for $3.95. When I got home, I fired up Internet Explorer and went to Mars. The depth was unbelievable. I seemed to be looking right into the guts of my monitor’s CRT. I’ve flown over the Grand Canyon and compared to this, the Grand Canyon was flat. The on-board instruments include: • A miniature thermal emission spectrometer (Mini-TES) to do a variety of spectroscopic tasks. Water and carbonates have well defined infrared absorption bands. If water is present, this instrument will confirm its presence; • A rock abrasion tool (RAT) to grind away the weathered surfaces of rocks to expose fresh surfaces without the contamination that comes from weathering;

• A Mössbauer Spectrometer (MB) to help in the identification of the mineralogy of the iron-based rocks and soils; • An alpha particle x-ray spectrometer (APXS) for elemental analysis. I once set up an alpha spectrometer near Wollaston Lake in Northern Saskatchewan. I thought that place was far out—but now there’s Mars; • A collection of magnets to collect magnetic dust particles either from the atmosphere or from the material ground up by the RAT for further MB or APXS analysis; • A microscopic imager (MI) for taking close-up pictures of the rocks and minerals from the surface or ground up by the RAT. If you want to be up with the latest about Mars and have a bit of fun while doing so, one of the links on the JPL site will take you to a page from which you can download a Mars screensaver. The one restriction in using this screensaver is that you must have an always-on Internet connection as it’s going to keep going to the JPL for updated information. Incidentally, they found water. When you look at those pictures and that unfriendly surface, it’s hard to believe that anybody lives nearby. I’m now hoping that some Martians will walk up to one of the Rover cameras and wave a cheerful greeting. If they are wearing Maple Leaf sweaters, that will prove once and for all that Toronto is the centre of the universe! You can reach our Chemputing editor, Marvin D. Silbert, FCIC, at Marvin Silbert and Associates, 23 Glenelia Avenue, Toronto, ON M2M 2K6; tel.: 416-225-0226; fax: 416-225-2227; e-mail: marvin@silbert.org; Web site: www.silbert.org.

April 2004

Canadian Chemical News 7

Chemfusion Section head

Writing the Book—on Paper Joe Schwarcz, MCIC t was a quasi religious moment. There in front of me, in a display case at the British Museum, lay the original copy of “The Adventure of the Missing Three Quarter” in Sir Arthur Conan Doyle’s own hand. Like any other Sherlock Holmes fan, I have read and reread the detective’s adventures numerous times, but never before had I gazed upon an original version. Unfortunately, the hallowed moment was a little tainted by the appearance of the manuscript. It was a brownish yellow in colour! Of course, one would expect a hundred-year-old piece of paper to show its age. That was no surprise—but the appearance of the Missing Three Quarter’s neighbour was. A Gutenberg Bible, produced over five hundred years earlier, looked as good as new! And it will likely be on display long after the Sherlock Holmes manuscript has crumbled away along with millions of other books stored in the British Library and other major libraries around the world. What is the difference? The type of paper that was used. Ah, paper. We don’t give it much thought, but our society would grind to a halt without it. Remember those promises that computers would provide a “paperless society?” Forget it. We use more paper than ever. Rough copies spew out of our printers and we use reams of paper to feed our Internet habit. Yet, most people have no idea of the complex chemistry involved in producing the marvellous product that gives us grocery bags, facial tissue, toilet paper, books, and a myriad of other products, including of course newsprint. The earliest forms of paper were not very complicated. Thousands of years ago, the Egyptians scraped out fibres from the inside of the bark of the papyrus plant and pressed them into sheets. Our word “paper” derives from “papyrus,” but papyrus wasn’t really paper. Not by our modern definition anyway: paper is the substance that forms when a slurry of disintegrated cellulose fibres is allowed to settle on a flat mould. When the water is drained away, the deposited layer can be dried into paper. The oldest surviving such piece, although

8 L’Actualité chimique canadienne

devoid of any markings, was discovered in 1957 in a Chinese tomb and dates roughly to 100 BC. The first paper with writing on it is also of Chinese origin, and can be traced to about 110 AD. Supposedly, this paper was made by a process developed by Ts’ai Lun, the “chief eunuch” in the Emperor’s court. Why the Emperor needed eunuchs isn’t exactly clear, but guarding the ladies of the court would be a good guess. In any case, Ts’ai Lun apparently had some time on his hands and discovered that macerating hemp fibres, old rags, and scrapings from the inner bark of mulberry trees with water, and then spreading the resulting pulp thinly on a drying frame, resulted in a material suitable for writing.

Amazingly, news of this discovery did not spread to the Western World for about a thousand years. Europeans recorded their history on parchment, laboriously made from animal skins. When word finally reached Europe through the Arabs who had learned about paper making from the Chinese, one would have expected the Church to jump on the new technology. Such was not the case. Parchment was the only material fit to carry the Sacred Word, the Church maintained, and called paper making a “pagan art.” Initially, there was not much opposition to this curious view because paper making was not an easy task for Europeans. There were no mulberry trees,

avril 2004

which seemed to be the key to Chinese paper. Finally, the Europeans turned to hemp fibres along with cotton and linen rags as raw materials. These were boiled in water to a point of disintegration and were then pounded into a pulp before pouring into drying trays. Treatment with animal gelatin usually followed to prevent water absorption and to reduce the spreading of the ink. Each sheet had to be made by hand, but the paper was of remarkably good quality, as witnessed by the spectacular condition of manuscripts such as the Gutenberg Bible. (Gutenberg printed bibles both on parchment and on paper and thus his work represents the transition from the old to the new.) Soon though, as more and more people learned to read, and the Industrial Revolution began to pick up steam, rags were no longer able to meet the demand for paper manufacture. This forced the English to pass a law that all burial garments had to be made of wool, a substance that could not be used to make paper. By the mid-19th century the shortage was so severe that America actually imported linen wrappings from Egyptian mummies to make paper. And then came a breakthrough. Friedrich Keller in Germany devised a method of making paper from trees by chipping wood and beating the chips into pulp. The pulp could be mixed with water, and the resulting slurry poured through a fine screen. Drying the residue from this “mechanical pulping” yielded sheets of paper. The same stuff we rely on so heavily—and take for granted—today.

Popular science writer, Joe Schwarcz, MCIC, is the director of McGill University’s Office for Science and Society. He hosts the “Dr. Joe Show” every Sunday 3–4 p.m. on Montréal’s radio station CJAD. The broadcast is available on the Web at www.CJAD.com. You can contact him at joe.schwarcz@mcgill.ca.

Chemical Shifts

Chemical Shifts What’s new in chemistry research? Chemical Shifts offers a concentrated look at Canada’s latest developments.

Super-cool and superfluid: how many helium atoms does it take? ne frequently thinks that properties of individual molecules and atoms are governed by quantum-mechanics, whereas large assemblies of molecules are described by classical/statistical physics. On the other hand, a variety of phenomena exist which demonstrate that even large ensembles of molecules can behave as quantum systems. As it turns out, the discovery and description of all of these phenomena have eventually resulted in Physics Nobel prizes, for example, in superconductivity (1913, 1972 and 2003), lasers (1964 and 1981), superfluidity (1962, 1978 and 2003), and most recently Bose-Einstein condensates (2001). Superfluidity describes the eerie property of liquid helium to flow without any trace of viscosity at below 2.18 K. This results in the spectacular observation of liquid helium climbing the walls of a beaker and being able to crawl through cracks so small that even helium gas would not be able to readily diffuse through them. But when exactly turns a handful of helium atoms into a superfluid liquid? An intriguing answer to that question has come from an unexpected direction. The research groups of Wolfgang Jaeger, MCIC, of the University of Alberta and Bob McKellar of the Steacie Institute, NRC, in Ottawa have used microwave spectroscopy and high-resolution infrared spectroscopy to look at just how much drag a molecule feels that is surrounded by 1, 2, 3 and up to 20 helium atoms. Both groups found unexpected trends in the drag (or rather the moment of inertia as determined from the rotational constants) as a function of the helium droplet size. In a paper on the molecule O=C=S surrounded by up to

20 helium atoms (Science 297, 2002, 2030) and more recently N2O-helium clusters (Phys. Rev. Lett., 91, 2003, 163401), it was shown that clusters with less than five helium atoms behave as would be expected from weakly bound van-der-Waals clusters, but that O=C=S embedded in clusters with more than eight or nine helium atoms

Cathleen Crudden, MCIC Hans-Peter Loock, MCIC

the cluster size at which helium exchange interactions become important. Chemistry professor Pierre-Nicholas Roy of the University of Alberta and S. Moroni of the University of Rome, Italy, have recently calculated rotational constants of the helium-OCS clusters with or without exchange interactions. They found that

Figure 1

actually rotates more freely as helium atoms are added! McKellar explains that this implies that even helium atoms in the first solvation shell show signatures of superfluidity. This “turn-around point” depends on the embedded molecule and is even less for N2O where only six to seven helium atoms are sufficient! The experimental work on doped helium clusters inspired a flurry of activity by theoretical chemists to determine the exact onset of superfluidity, which they define as

about 10 helium atoms were sufficient for superfluidity. This is a surprisingly small cluster size for an effect that is essentially a bulk phenomenon (J. Chem. Phys., 2004) in press. Not surprisingly, all researchers agree that “more work needs to be done” and continue to refine the quantum mechanical methodology used to calculate these systems as well as expand on the size of the cluster and complexity of the molecules embedded in the cluster.

April 2004

Canadian Chemical News 9

Chemical Shifts Section head

Figure 2

Solid evidence for the effect of oxygen on zeolite spectra eolites are very important naturally occurring and synthetic materials employed in petrochemical refining for the cracking, isomerization and synthesis of hydrocarbons. These processes are critical for the production of gasoline and other products. The well defined shapes of the cavities in zeolites makes them significantly more selective for hydrocarbon cracking reactions than the simple aluminosilicates they replaced. Zeolites are quite selective about the molecules they allow in their pores, which gives them applications in separating isomers of aromatic compounds or branched vs. straight-chain alkanes. Thus studying the interaction between adsorbed molecules and the silicon framework to determine the location and strength of these interactions is of considerable interest. Colin Fyfe, MCIC, and his research group at the University of British Columbia in Vancouver, BC have shown that 29Si-29Si INADEQUATE spectra of important zeolites like ZSM-5 can be used to assign the signals in high-resolution CP-MAS NMR spectra to the individual positions of the silicon atoms in the zeolite. urthermore, by examining the rate of

10 L’Actualité chimique canadienne

polarization transfer between the protons of the adsorbate and the silicon atoms of the zeolite, information can be obtained about the average location of the adsorbed molecule. As the thermal motions of the adsorbed molecule decrease with decreasing temperature, the spectra are generally recorded at as low a temperature as possible. Unfortunately, significant broadening occurs as the temperature is decreased as shown in Figure 2A. Dipolar coupling between 1H and 29Si is ruled out as the cause of this resolution loss, since increased decoupling power does not result in improved spectra. The slight increase in the resolution obtained at temperatures lower than 200 K suggests that the loss in resolution is not due to freezing out of the motion of the adsorbate. Interestingly, Fyfe and co-worker Darren Brouwer, MCIC, found that T2 relaxation was responsible for the decrease in resolution at lower temperature. Since T2 relaxation is often induced by paramagnetic oxygen present within the channels, Fyfe and Brouwer collected spectra in deoxygenated samples, using nitrogen as the bearing and drive gas instead of air to prevent contamination. The results of this experiment are remarkable. As shown in Figure 2B, the resolution of the spectrum is

avril 2004

dramatically improved. In addition, significant resolution is still observed at temperatures as low as 160 K. By examining the rate constants for relaxation of specific sites, Fyfe and Brouwer were able to conclude that oxygen resides primarily near the zig-zag channel of ZSM-5, while the adsorbate (p-dibromobenzene) is preferentially adsorbed in the large channel intersection. These findings have significant implications for the study of zeolites and other silicaceous materials by solid state NMR. For example, the presence of oxygen can shorten the 1H T1ρ relaxation time at low temperature, leading to inefficient 29Si{1H} cross polarization. If oxygen is displaced during long experiments with nitrogen as the drive gas, significant changes in the spectrum can result throughout the course of the experiment. Most importantly, this discovery means that in some cases, the very simple solution of deoxygenating your sample may lead to significant gains in low-temperature resolution. For the original publication, see the Journal of the American Chemical Society, 2004, 126, 1306.

Still the Stille, but what a remarkable change a charge makes! he Stille reaction, like other Pd catalyzed coupling reactions, generally requires an aryl or vinyl bromide as the electrophilic coupling partner (equation 1). Interesting, traditional electrophiles such as imines, ketones or aldehydes have remained unreactive under Pd-catalyzed coupling conditions. That is until chemistry professor Bruce Arndtsen, MCIC, and graduate students Jason Davis and Rajiv Dhawan, MCIC, at McGill University reasoned that the unreactivity of these substrates was due to the unfavourable charge that would develop on the nitrogen atom of the imine during the putative oxidative addition (equation 2). They further reasoned that beginning the reaction with an iminium ion instead of an imine would prevent the buildup of negative charge on the nitrogen (equation 3), and the amide substituent would stabilize the positive charge on Pd. In fact, the coupling reaction shown in equation 3 is even easier

Chemical Shifts

than this. The iminium ion doesn’t need to be preformed: the addition of benzoyl chloride to the reaction mixture is sufficient to activate a variety of imines toward Pd-catalyzed coupling reactions with vinyl stannanes. Remarkably, even imines containing aryl iodides undergo oxidative addition preferentially at the imine, rather than at the halide (equation 4). Other advantages of this new reaction is that it can be expanded to include the incorporation of other reagents such as carbon monoxide (equation 5). Considering the importance of highly functionalized alpha-substituted amines and amides such as 5, this reaction promises to see widespread application. For the full account of this work see the original report in Angewandte Chemie International Edition, 2004, 43, 590. Cathleen Crudden, MCIC, is an associate professor at Queen’s University in Kingston, ON.

PdLn + Ar–Br

(eq. 1)

LnPd Br R

R PdLn + H

difficult oxidative N addition LnPd R' 1 2

R O

PdLn +

facile oxidative addition

LnPd

(eq. 3)

R' (eq. 2)

Ph R

Equations 1–3

MeO

Et +

SnBu3

MeO

Hans-Peter Loock, MCIC, is a physical chemist and assistant professor at Queen’s. His research interests are in laser spectroscopy and sensing.

facile oxidative addition

MeO

PhCOCl 2.5% Pd2dba3•CHCl3 RT, 16 hr CH3CN/CH2Cl2

N Bn

+ Cl

MeO

+ PhSnBu3 OBn

Ph (eq. 4)

Ph O

Pd2dba3•CHCl3 CO

(eq. 5) Ar

N 5

OBn

Equations 4–5

April 2004

Canadian Chemical News 11

Waste Not—Want Not? Green chemistry’s current trends and future aspirations

onsider this: what do pulp and paper, lumber, petrochemicals, textiles, transportation, health care and pharmaceuticals, architecture, mining and steel, food and agriculture, plastic/ rubber/coatings, and electronics have in common or a new product with the same fudctions but without harm? Together they define modern civilization, constitute the world economy, and all involve chemistry. They all generate certain waste that results in environmental and social concerns. Historically, industries have been established by scientific expeditions that have resulted in new industrial territories. Traditionally, those expeditions fostered the creation of foundations and further improvements that were then carried out by polishing the production processes and by recycling the waste—both for economical and environmental reasons. Studies were performed to determine the effect of the waste on the environment (often after an environmental disaster). The gradual improvements to the original foundation became the industrial standard. While those initial expeditions allowed for the realization of new products, they were very often not the more efficient or effective methods of production. In the early 1990s, the field of green chemistry emerged.1 The term “Green Chemistry” was coined by Paul Anastas in 1991 and defined as “the design of chemical products and processes that reduce or eliminate the use or generation of hazardous substances.” In contrast to the traditional wisdom, green chemistry adopts a totally new philosophical approach to address the delicate balance of economic development and environmental protection by creating a new science that eventually will enable industry to produce the same products in the most direct, economical, and socially/environmentally responsible

12 L’Actualité chimique canadienne

Chao-Jun Li, MCIC

manner possible. It also designs the chemistry so it is less hazardous. It ensures minimized hazard is a performance criterion in the feedstock, reagents, solvents, transformations, and products that we make. Green chemistry results in the reduction and/or elimination of hazardous substances. There are several misperceptions related to the field of green chemistry:

• “Green chemistry has nothing to do with my industry.” An industry is defined by the production of useful products. Regardless of the material product, some method of chemistry is used to produce that product. Green chemistry is aimed at identifying and perfecting the most efficient industrial methods of production.

• Green chemistry is environmental chemistry. This is the most common misperception. Although they are related to each other, environmental chemistry focuses primarily on studying the effect of environmental pollutants, whereas green chemistry is dedicated to the invention of new sciences and technologies to prevent the formation of any waste in the first place.

In its early stages, green chemistry has been primarily related to the chemical industry. In a new trend, it has now evolved into various industrial sectors since all industrial processes involve one or more of the following basics: raw materials, chemical reactions, solvents, and separation/purifications. Industrial raw materials are often artificial chemicals produced by manufacturers. However, the green chemistry approach starts directly with the natural materials. In terms of the chemical reactions, they often remain unchanged for long periods of time and industry has dealt with the resulting waste by finding methods of recycling. Alternatively, green chemistry invents new reactions that both use readily available raw materials and are atom-economical— which maximizes production and minimizes waste-production. Various organic solvents or water are used as traditional industrial solvents. The current research on green solvents include liquid and supercritical CO2, ionic liquids, as well as water and hot water being used in new ways. The new uses of water and hot water include catalyst recycling (watersoluble catalyst), product isolation, and increased/unprecented new chemical reactivities. Traditional purification methods in industry include adding acids/bases and using crystallization, chromatography, and distillation. These separation methods have been the norm and have remained in use

• Pursuing green chemistry is not cost effective. Green chemistry’s objective is to minimize waste, and thus will allow for increased profits by saving reagents, solvents, energy, waste disposal costs, personnel costs, and increasing production. More importantly, it creates new businss opportunites by scientific innovations. • Green chemistry has to be perfect. Green chemistry endeavours to perfect industrial production. However, like any other scientific discipline, it recognizes that the prototypes (of academic research) may have their shortcomings and will progress to perfection through self-correction. In addition, different chemistry may be “greener” in one situation than in others. A perfectly green process may not be so green if it hasn’t been applied in the right situations.

avril 2004

for the last few centuries. They both generate large amounts of acid, base, and solvent wastes, and are often energy intensive related to heating for crystallization and distillation, and evaporation of solvent for chromatography. New trends in separations bypass these processes by using techniques such as CO2 extraction-phase separationevaporation, membrane separation, and reforming by-products into new products. In addition, green chemistry adds value by developing new products, new chemistries, and enhanced performance in everything from plastics, to pesticides, to pharmaceuticals. The current trends in green chemistry in specific industrial sectors are listed below: • Pulp paper/textile: trends in this industrial sector focus on developing new methods for cellulose purification (other than strong base washing) such as CO2, ionic liquids, high temperature water extraction of lignins. Alternative bleaching methods (such as new high efficiency and non-polluting oxidants), new ways of dying (such as by using liquid CO2 techniques), and new ways of cleaning (such as CO2-based dry cleaning) are emerging. • Petrochemicals/fine chemicals: current trends in petrochemicals are directed at developing new low temperature catalytic refinery, molecular-engineered membrane separation, direct conversion of petroleum to high-valued products, new engineering concept (use flow-bed reactors instead of batch reactors), new media such as ionic liquids, and new analytical techniques (such as sensors) to control chemical reactions. In addition, fine and commodity chemicals are focusing on biomass-based polymer materials, biodegradable polymer materials, enzyme and other biocatalysts, high-efficiency catalytic processes (both high catalytic activity and recycling ability), chemistry to eliminate unnecessary repetitions such as protection/deprotection and strong acids/strong bases utilizations, as well as cleaner reaction media. • Fuel/transportation: trends in this industrial sector are on developing more efficient catalytic converters for fuel cell research, biomass-based hydrogen and alkane production (by using biological and chemical methods), biofuel from biomass, and reforming of green house gases (methane and CO2) into alcohols.

• Pharmaceuticals/personal care: current trends in pharmaceuticals focus on inventing new reactions (catalytic, atomeconomical, tandem, cascade) that will be produced more rapidly in fewer steps, the development of array reactions, direct conversion of biomass into pharmaceutical products, new reaction conditions (cleaner solvents, biological processes, etc.), and new energy input methods (such as ultrasound, microwave). There has also been interest in developing skin care products based on biodegradable biomass.

industry through scientific innovaitons. What more could we ask for? Green chemistry defines the industrial ideal for future generations.

Endnote 1. Anastas, P. Warner, J. C. Green Chemistry, Theory and Practice, Oxford University Press, New York, 1998.

• Mining: direct extraction and processing of target metals (such as using designer ionic liquids). • Food industry: there is an ongoing (although still controversial) interest in developing genetically engineered crops to avoid using pesticides and fertilizers. Other trends in this industrial sector are on developing biodegradable pesticides, smart fertilizers for controlled release, biomass utilization technologies, new food preservation methods, new pasteurization methods, and Cl2 alternatives for drinking water sanitization. • Electronic industry: new chips-making methods are based on high efficiency and low waste. CO2-based chip-cleaning processes use green chemistry to make nanomaterials for electronic applications. Canada is an opportune place to make use of developing biomass technologies. Biomass has a broadening range of sources of waste including sewage, crops, municipal waste, plants (forest/grass), and pulp and paper. The organic matter in the biomass is mostly cellulose, lignins, and fatty acids. This matter can be converted into a variety of products including fuel, fine chemicals, pharmaceuticals, polymers, and personal care products. In just a decade, the concept of green chemistry has fundamentally changed scientists’ ways of thinking about reconciling production, economy, and environmental issues. It’s a new philosophical approach—studying and creating new scientific foundations based on the principles of sustainability and efficiency. Green chemistry’s ultimate goal is to attain the most economical return, the most social benefits, the least environmental impact of all industrial sectors. and to create new

C. J. Li, MCIC, is a professor of organic chemistry and a Canada Research Chair (Tier I) in green chemistry at McGill University in Montréal, QC. He received the 2001 Presidential Green Chemistry Challenge Award (Academic) in the U.S.

April 2004

Canadian Chemical News 13

Innovation Roadmap Canada’s bioproducts industry’s report on bio-based feedstocks fuels, and industrial products

network of business people, academics, government personnel and consultants with expertise in the bio-based economy and a strong interest in “thinking green” have developed the Innovation Roadmap on Bio-Based Fuels and Industrial Products. Its objective is to identify bio-based opportunites for utilizing Canada’s abundant bioresources to grow the economy while protecting the environment and our quality of life. The roadmap report is available …. It covers a number of chemical and bioconversion technologies and identifies both immediate and future markets for the bio-based economy. The roadmap deals with the transformation biomass from the agriculture, forests, marine and municipalities into fuels, chemicals and materials. It addresses the process of mapping of inventories, harvesting, transformation, separation and upgrading technologies.

The vision The overarching vision is to make Canada a leader in environmental and sustainable technologies through its “Natural Advantage” and to grow the economy while improving our environment and quality of life through the development and commercialization of industrial bioproducts and processes from our abundant biomass resources. Biofuels and bioproducts are potentially cleaner and cheaper than fossil-based products. They are also renewable, unlike fossil-based products. Biofuels and industrial bioproducts contribute to sustainability and growth in meeting burgeoning world demands for energy, chemicals and materials. This trend is already happening among member countries of the Organization for Economic Co-operation and Development, where highly educated populations and advanced communications accelerate global adoption.

14 L’Actualité chimique canadienne

The objective of the innovation roadmap is to identify technology-based opportunities for utilizing Canada's abundant bioresources in order to grow the economy while protecting the environment and our quality of life. The roadmap report covers a number of chemical and bioconversion technologies, and identifies both immediate and future markets for the biobased economy. As stated in the body of this document, one of the main themes is that new biotechnologies have the potential to capture economically viable materials and energy from biomass residues inclusive of both underutilized materials from what is now harvested and land that is not currently utilized. Another recurring theme is “your waste is my feedstock.”

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

avril 2004

J. E. Cunningham

efficient energy systems such as fuel cells, small- to medium-scale distributed cogeneration systems and biofuels (biogases, biodiesel, bio-oils and alcohol) including many novel, high, value chemicals and materials. Biofuels and bioproducts are strategically important to Canada. There are several successful Canadian companies actively engaged in this field. Canada is in an excellent position to benefit with its resource base, expertise and developing community-based eco-industrial clusters. The biomass opportunity will provide new revenue streams for the traditional agricultural, forestry and marine resource sectors and communities. Major benefits can be derived from Canada’s exceptionally large biomass resource—Canada’s “Natural Advantage.” For instance, the BIOCAP Foundation estimates that our standing forests has an energy content that is equal to 69 years of Canada's current energy demand that is met by fossil fuels. Action must be taken now. Substantial biofuel opportunities both now and in the near-term future are ours to lose despite our abundant biomass resources and strong competitive advantages, especially in the physical, chemical and thermal conversion of waste and residue biomass to bio-based energy and industrial products. A theme running though this roadmap is the potential for new biotechnologies to capture economically-viable materials and energy from residues including biomass from underutilized materials and land. The production of high-value by-products can be an incentive to recover and recycle waste energy and organic residues. At the same time, there is strong potential for greater synergy and resource conversion efficiencies in production through effective use of co-products. The business case for future biofuel and bioproduct developments, however, needs

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

Green Chemistry Goals in Canada • Exploit Canada’s green advantage for the production of bio-based chemicals and fuels;

“The Stone Age did not end for a lack of stones,

• Invent reactions that reduce the production of greenhouse gases;

and the oil age will end not for a lack of oil.” Bjørn Lomborg, The Skeptical Environmentalist

“We stopped using stone because bronze and iron were superior materials,

• Adapt to work in environmentally benign solvents such as supercritical CO2 or ionic liquids; • Harvest electricity, a renewable energy, for chemical synthesis; • Evolve enzymes for chemical synthesis of fine chemicals and pharmaceuticals;

and likewise we will stop using oil when other energy technologies provide superior benefits.” Sheik Yamani, Saudi oil minister, 1973

• Convert biomass (e.g. lignin) to synthetic intermediates and fuels; • Develop manufacturing methods using biocatalysis; • Convert complex ligno cellulosics to homogeneous thermoplastics;

Acknowledgement Rick Smith, president and CEO of Dow AgroScience Canada, Inc. is Industry Champion for the Innovation Roadmap on Bio-based Feedstocks, Fuels, and Industrial Products.

• Evaluate whether new processes really are green.

Canadian Green Chemistry Network www.greenchemistry.ca

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

April 2004

Canadian Chemical News 15

Green Machines

Meet the What’s new? Who’s who? What’re they up to?

The field of green chemistry and engineering is only a decade old— but branching out in exciting directions! Canadian trailblazers report on the paths their research is taking: R. H. Ma rchessau lt, FCIC E.B. Eddy professor Departm ent of ch emistry McGill U niversity Montréal, QC

n Marsa imie Benoît ur t bioch e e i e s m i l Profes t de ch c à Montréa temen lDépar té du Québe nic po rsi d orga n a i Unive l, QC a ic t ob n gan éa of inor models to n Montr io trot a -oxid w elec Synthesis nin o e g r i t n l c a le f f e and scale o o n -up of ch hydroxya pment rking o dation emically lkanoates I’m wo electro-oxi , and develo m o a d s macrom ified bacte and block ts s, on rial polycopolyme lutant ded produc cell. rs. Our ob omers for convers d a ic a e lt u o l io jective is n to graft va tov Joelle Pelletier, M clinical a al pho CIC ic m pplication e h c Professeure adjo s. inte Département de chimie CIC M r, e Université de Mon g D. Sin tréal r o Robert s s Montréal, QC nd profe emistry Chair a h c My research grou ent of p is involved in th Departm ’s University s e modification of a y zy r h mes for use as en a c u M s t ents in n a vironmentally be S solve r n S fo nign catalysts, by e ap e N pl r ica , g ts tio x n f n of e o “d t lv ire n o ct Halifa e ed s evolution” metho m s computer-assisted dologies and develop s (RTILs) a urrently molecular modell id d in the . This c u te is s iq s w e e L ing. e r n th te n ic d in y n n s a e Io r ic n a n ow ga We ature se of kn ents ed in or Temper ents us n, and u bimetallic reag of g o a ti Room e a r iz r ic ll te f e c o ta s e ra s u a n m e h o d th sis, c reacti organo Group h ates an s. e synthe d in addition, tr s th b ead, bioc s u e s lv e invo onversio ts, an mplex turated n o a e c s Pete lv n ic o u ll n and su s ta s to e a ) s m 3 o e IL n stainable r C. K. Lau a iM RT g S r n o S y 3 b u developm d B e s E z nvironm ataly ent (such a ental scie ctions c a B e io r te nce secto in c h nology R RTILs r esearch National Institute Research Research Council Canada interests y encompa CIC hemistr ability to Montréa M , f s c s a o m l ls f l, QC ; ic o h u ro s c e of enz -organism bioreage ssor el S y ymes, su s as envir nts; mic Marc ant profe hemistr c h o ro a n sB mental a be expressio c st nd susta a, n and bio s as a biomass fo aeyer-Villiger m Assi tment of elph inalph ono-oxy process r o b u s r t a o s u a e G s rc fo l p d e f genases, r d o o e n o th f v y b e a e l De lo io y a o t p c d a m i v p ta a s e n n ly r n r c t; b s e io a e ts o m developm process, ; gene clo as ug ati Univ h, ON and appli ent of pollution ent of a ning, ant s ydrogen d n s c p tr c o l a u o n ti ng know trol tech ons in su f ab nic h Gue o le n s o dge ta lo n in g o able dev y, green io rsi elopmen chemistr Venkatesh M onve hrough c t. y c ed i a t t ly s. Assistant pro Cata -diols ction fe a ss e or r a g Bioprocess ome genolysis engineering o College of E hydr ngineering University of Saskatchew CIC an uclair, M Karine A t of chemistry Saskatoon, SK My research en areas includ Departm e post-harve of natural p niversity U l st thermal p roducts and McGil in ro ce ex ss tr microwave action of pla ing l, QC be used assisted en nt materials Montréa es can re m lt y a ergy efficien z l n u si ta e enhanced ch n n g t methods. P450 onme t ir emical appli a v n s th e a M h re w ic rowave cations are sho new process a mo s suc rapidly expan /product d e try to reaction thesis as r n W y fo s . n e is d o v s in ev g into elopment fo herbs/spices taly enati electi r functional and neutrac chiral ca r even dehalog enantios foods, euticals. hemical ,o c s n to o ti e a v nati epoxid lations, hydroxy 16 L’Actualité chimique canadienne

avril 2004

Thierry Ollevi er, MCIC anics h c e ll e m ic Professeur d e N . li p A p a Jim Département ssor and de chimie te profe il engineering Associa iv c f o Université La t n e tm r val Depa ity es Québec, QC Univers e enzym v ti a McGill id x s go Our research nd al, QC program deal compou r nds usin Montré s with synthe e compou ses), and target ch c th emistry, and it o ti a f tic organic o m o ty r a a ie id involves the de r s x a u o v o l e o e u g n e r e q th a h m la velopment of et p f f a ho o o ly do d o n n lo n p o gi o a ti es d ti new based on bism Oxida ases an s, dyes, sforma Catalytic asym uth(III) cataly peroxid es tran solution c amine metric synthe sts. (such as enols, aromati on accomplish nt changes in si s using new bi chemistry is al ti olour. ta ph a c r e o id sm d d p x so n ut a h pa O lu im , c rt of our program in g ts. vity . pollutan while achievin disrupting acti priority e nd crin compou y, endo parent g toxicit in d lu c in quality C. J. Li, MCIC Professor of organic chemistry Canada Research Chair (Tier I) in green chemistry McGill University Aichen g Chen Montréal, QC Assista nt prof e Depar ssor tm Our research is on green chemistry for fine chemical and pharmaceutical synthesis Lakeh ent of chem is ead Un by developing new catalytic organic reactions in water, ionic liquids, and liquid CO2. iversit try Thund y er Bay We are also interested in direct functionalization of hydrocarbons and biomass into , ON value-added products. At Lak eh Forest ead, we are collabo Pr ra lignin, oducts Inc. to inve ting with Bo a wast stigate water e prod valueCanad u added b Jonathan Gagnon ia produc ct of the pulp iomass con versio n ts. and pa Professeur n of per ind et sciences de la santé ustry, ent de biologie, chimie tem par Dé to à Rimouski Université du Québec Rimouski, QC itzer, MCIC Andreea Schm te in jo ad ation of biopolyProfesseure works on the transform up gro ie ch im ear ch res in de My t s asymmetric catalysts Départemen ir use as homogeneou éal the tr for s on rs thi M me gh de ou thr ité Univers knowledge acquired be ll aqueous media. The wi Montréal, QC ses ces pro er transformation research on biopolym s fields of applications. rou p me is to develo transposed to nu m ra og pr ch ar ive of our rese ls containing The main object for bio-materia ds ho ur et m gn ecific needs. O rational desi Laborato s adapted to sp tie ds vi ar ca w ire de chim to ed Jean Less liz ed functiona ches, direct ard, ie et élec oa pr ap ar ul e ec th ol e tr lv o am vo c pr in himie org FCIC su , ls n ia er at moder m lid aniques so d Départem synthesis of ar recognition an ent de ch ul the design and ec ol m in es imie Universit miw principl é de Sherb eparation of se use of brand ne rooke try for the pr is em ch s er Sherbroo Electroch biopolym ke, QC emical/so mes. noelectro sion in gre synthetic enzy c h emical sy en media nthesis a (aqueous liquids, a nd media/m nd super J. R. Jocelyn Paré icroemuls convercritical fl biomass io u ns, ionic id c s o ) n using ren Head Science – M version; chemose AP Division ewable e electroca lective nergy: ta ly Environment Cana tic electrohy organom da drogenati hydrogenation fo etallic rea Ottawa, ON o r ns; elec ctions. trocataly tic Development of Environment Cana da’s energy-effic Microwave-Assiste ient patented d Processes (MAPTM ) for the synthesis industries in Cana and extraction da, to provide thes e Canadian sectors energy-efficient in with a unique dustrial process th at will offer health, environmental be economic and nefits by reducing gr een houses gases co nt am ina nt ll s. a an d criteria air h rs . Ma William D nce Food Scie iversity n U l il G c M , QC l, sediment) Montréa edia (soil/ m m te iu la d u e ic Collected with help from Philip G. Jessop, rt as a m tion of pa exploited e remedia MCIC, Canadian Research Chair c and/or has been ti e a id m x During th ro io a d of poly carbon l n a o c ti ti a in green chemistry. ri ic rc if e ! list sup detox ame to the n ntinuous r o u c o e y d th s. d r n A fo rbo isit d hydroca formation, v chlorinate For more in enChemistry

re ueensu.ca/G www.chem.q

April 2004

Canadian Chemical News 17

Developing Green Chemistry Organometallic reactions in water and other alternative media

rganic solvents are used extensively in the chemical industry, and their release into the environment has been a matter of great concern. Because of the wide range of hazards that can be associated with these volatile organic compounds (VOC), a number of regulations are in place to govern their production, use, or disposal.1 Most regulations are concerned with overall VOC reduction. A major application of organic solvents is to serve as the reaction medium in which other compounds react. Using the precepts of green chemistry, researchers in industry and academia are developing new alternative solvent systems for chemical synthesis that may minimize hazards associated with traditional solvents.2 Currently, the most extensively examined alternative reaction media are: water,3 ionic liquids,3a supercritical carbon dioxide4 and ultimately, the solvent-free conditions. A number of excellent monographs have been written on the use of these alternative solvent media for chemical reactions and processes.2–4 A critical question is: what if these solvents react with the intended reagents? This question is especially relevant in the case of reactive organometallic compounds such as the Grignard or organolithium reagents. These compounds are very useful in chemical synthesis, but they are well known to react with water or carbon dioxide and likely with many common ionic liquids as well. In order to overcome this critical problem, alternative organometallic reagents and reactions, compatible with water or other alternative media have recently been developed.

product alcohols (2) under the Barbier conditions (Scheme 1).6 These metals include In, Zn, Sn, Bi, Sb, Mn, Ga and Mg. The experimental set-up for these reactions is usually simple as there is generally no need for moisture exclusion or inert atmosphere. Depending on the metal used, they show different chemoselectivity in mediating the coupling between allyl halides and carbonyl compounds: In and Sn allylate both aldehydes and ketones; Bi allylates aldehydes and selected ketones; Sb allyates only aldehydes and Mn only aryl aldehydes.6 When substituted allyl halides are used, conditions can be found to give regioselectively the a- (3) or the y-regioisomers (4). Similarly, depending on the

Tak Hang Chan, FCIC nature of the substituent, reactions with substituted propargyl halides can give either the homopropargyl adducts 5 or the allenyl adducts 6.7 Equally impressive is the stereoselectivity of some of these reactions. Examples of high 1,2- (compound 7),1,3- (compound 8) and even 1,6- (compound 9) diastereoselection are known. An example of asymmetric synthesis is the generation of allylglcine 10 and other unnatural ∝-aminoacids via zinc mediated allylation in aqueous media with diastereomeric excess (de) as high as 99:1.9 Indium mediated enantioselective allylation of aldehydes in an aqueous medium can also be achieved with 34 percent to 92 percent enantioselectivity.10

Organometallic reactions in aqueous media In the last decade, it has been found that a number of metals can mediate the reactions of carbonyl compounds (1) with organic halides in aqueous media to give the Scheme 1

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Photo by Matt Bowden

Advantages and limitations of organometallic reactions in aqueous media Organometallic reactions in aqueous media offer some advantages over their conventional counterparts in organic solvents. This is particularly true for reactions involving biomolecules such as carbohydrates, which are sparingly soluble in most organic solvents but soluble in water. An example is a concise synthesis of N-acetylneuraminic acid (12) from N-acetylmannosamine (11) as outlined in Scheme 2.11 The noteworthy features of the synthesis are: the hydroxyl and the carboxylic acid functions in the reactants do not require protection-deprotection chemistry; the C-C bond formation step provides useful synselectivity giving the desired diastereomer. There are limitations in using aqueous media for organometallic reactions. Currently, most of the metal-mediated reactions involve allylation or propargylation, and more recently, secondary alkyl halides. However, the reactions did not work well with primary alkyl or aryl halides. A second inherent limitation is that water sensitive substrates, such as imines12 or a-alkoxyalkyl chloride cannot be used. Finally, highly hydrophobic compounds insoluble in water tend to present difficulties in these reactions.

Another possible reaction medium is liquid carbon dioxide under super- or subcritical conditions.4 Using liquid CO2 as a solvent has the advantage that hydrophobic substrates can be easily dissolved, and the waste disposal problems associated with organic solvents can be avoided. Various aldehydes were cleanly allylated with indium and allyl bromide in liquid carbon dioxide.14 The limitation of liquid CO2 is exactly the opposite to that of water, in that polar compounds are not soluble in carbon dioxide. Ionic liquids have been advocated as the green solvents for the future.3a This is due to some intriguing properties of ionic liquids: high thermal and chemical stability, no measurable vapour pressure, non-flammability, and high loading capacity. The ionic liquids can be recycled easily and leave little environmental footprint. An attractive feature of ionic liquids is that their solubilities can be tuned readily so that they can phase separate from organic as well as aqueous media depending on the choice of cations and anions. Numerous chemical reactions, including some enzymatic reactions, can be carried out in ionic liquids.3a However, relatively few organometallic reactions in ionic liquids have been investigated thus far. Recently, it has been reported15 that indium, tin, and zinc can effectively mediate the allylation of carbonyl compounds

to replace these classical reactions in alternative media. It is hoped that the chemistry described in this article has helped pave the way for meeting the challenges ahead.

Endnotes 1 D. A. Sullivan, Kirk-Othmer Encyclopedia of Chemical Technology, v. 22, Wiley, New York, 1997, pp. 529–571. 2 W. M. Nelson, Green Solvents for Chemistry, Perspective and Practice, Oxford University Press, Oxford, 2003. 3 C. J. Li and T. H. Chan, Organic Reactions in Aqueous Media, Wiley, New York, 1997. 3 (a) R. D. Rogers and K. R. Seddon, Ed., Ionic Liquids. Industrial Applications to Green Chemistry, ACS Symposium Series 818, Washington, 2002. (b) P. Wasserscheid and T, Welton, Ionic Liquids in Synthesis; Wiley-VCH, 2003. 4 W. Leitner and P.G. Jessop, Chemical Synthesis using Supercritical Fluids, Wiley-VCH, Weinheim, 1999. 5 Selected references: (a) C. J. Li and T. H. Chan, Tetrahedron, 55, 11149, 1999; (b) Z. Wang and G. B. Hammond, J. Org. Chem. 65, 6547, 2000; (c) T. M. Mitzel, C. Paomo and K. Jendza, J. Org. Chem., 67, 136, 2002; (d) C. C. K. Keh, C. Wei and C.J. Li, J. Am. Chem. Soc. 125, 4062, 2003. 6 T. H. Chan, L. Li, Y. Yang and W. Lu, Clean Solvents, Alternative Media for Chemical Reactions and Processing, M. A. Abraham, L. Moens, Eds., ACS Symposium Series 819, American Chemical Society, Washington, 2002, p. 166. 7 K.-T. Tan, S.-S. Chng, H.-S. Cheng and T.-P. Loh, J. Am. Chem. Soc, 125, 2958, 2003. 8 (a) L. A. Paquette and R. R. Rothhaar, J. Org. Chem, 64, 217, 1999; (b) W. Miao, W. Lu and T. H. Chan, J. Am. Chem. Soc. 125, 2412, 2003.

Scheme 2

9 S. Hanessian and R.-Y. Yang, Tetrahedron Lett, 37, 5273, 1996. 10 T.-P. Loh and J.-R. Zhou, Tetrahedron Lett, 40, 9115, 1999. 11 T. H. Chan and M.-C. Lee, J. Org. Chem, 60, 4228, 1995. 12 W. Lu and T. H. Chan, J. Org. Chem, 65, 8589, 2000.

Scheme 3

Beyond aqueous media Of course, using no solvent at all could be the “ultimate” solution to minimizing solvent-associated hazards. Indium, zinc, bismuth and tin can mediate the allylation of carbonyl compounds under solvent-free conditions.13 Sonication was required for some of the reactions, and the reaction conditions had to be carefully monitored to prevent decomposition of the starting materials or products. In solvent-free conditions, solid substrates often failed to give satisfactory reaction.

in the ionic liquid [bmim][BF4] to give the homoallylic alcohols in high yields (Scheme 3). It is likely that with the appropriate choice of ionic liquid, more reactive organometallic reactions can also be performed with various halide and carbonyl substrates.

13 (a) X. H. Li, J. X. Haberman and C. J. Li, Synth. Commnu, 28, 2999, 1998; (b) P. C. Andrews, A. C. Peatt and C. L. Raston, Tetrahedron Lett, 43, 7541, 2002. 14 J. X. Haberman, G. C. Irvin, V. T. John and C. J. Li, Green Chem, 1, 265, 1999. 15 (a) C. M. Gordon and C. Ritchie, Green Chem. 4, 124, 2002; (b) M. C. Law, K.-Y. Wong and T. H. Chan, Green Chem. 4, 161, 2002.

Epilogue The Grignard-Barbier and related organometallic reactions in organic solvents have served as important methods for carboncarbon bond formation. Innovative chemistry and reactions must be discovered

T. H. Chan, FCIC, is the Tomlinson professor of chemistry at McGill University. His research interest is in organic synthesis and the development of new reactions in environmentally clean solvents.

April 2004

Canadian Chemical News 19

Directed Evolution of Enzymes Obtaining clean, efficient, and biodegradable catalysts Nicolas Doucet and Joelle N. Pelletier, MCIC Abstract his brief technological report presents an overview of techniques and applications in the field of directed evolution of enzyme catalysts. These techniques allow for the creation of modified enzymes that are better adapted to many industrial contexts. Recent applications in organic synthesis as well as commercial, biomedical, and environmental usage of these modified catalysts will be presented.

Résumé Cette brève fiche technologique présente en survol les techniques d’évolution dirigée permettant la génération de mutants enzymatiques pouvant être par la suite utilisés comme catalyseurs dans un contexte d’intérêt prédéfini. Quelques applications de ces catalyseurs modifiés sont présentées touchant des domaines aussi divers que la synthèse chimique, l’utilisation industrielle et commerciale, la recherche biomédicale et l’environnement. Le lecteur désirant une version française détaillée et en profondeur de ce domaine de recherche est invité à se référer à la fiche BIOTECHNO, vol. 2, n° 2 publiée par le Centre québécois de valorisation des biotechnologies du gouvernement du Québec www.cqvb.qc.ca/publications_ home.htm. Enzymes are among the most powerful catalytic molecules we know, accelerating chemical reactions at a rate of 106 to 1,017 times faster than the same uncatalyzed reactions. Moreover, they are often stereo-, regio- and chemoselective as well as being entirely biodegradable and environmentally friendly. On the other hand, reactions catalyzed by enzymes are generally confined to mild temperature conditions in aqueous solutions at pH 7. Because of these constraints, it is difficult to integrate

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enzymatic catalysts into industrial processes where they are prone to denaturation as a result of harsher prevailing conditions. Enzymatic engineering now offers the possibility of improving the robustness as well as the catalytic efficiencies of enzymes by techniques commonly known as “directed evolution.” This approach mimics natural evolution in a test tube by introducing randomly distributed mutations on the gene encoding the enzyme of interest. The resulting “library” of mutants is screened for a desired characteristic to attempt to identify a mutant enzyme that exhibits the characteristic of interest. Successful reports published in the last ten years teach us that the introduction of a small number of mutations on a given enzyme is often sufficient to drastically modify its properties. The possibilities of applications are almost endless and have been amply demonstrated in improvement of catalytic efficiency and robustness, modification of optimal temperature and pH, among others. These

Mutated enzymes recognize and degrade many stable chemical pollutants modified enzymes are now used in a considerable number of chemical fields ranging from chemical synthesis, pharmaceutical and biomedical applications to environmental detoxification and numerous other industrial purposes. A few examples will be presented here. References [1–4] contain detailed examples and thorough investigations of the methods used for directed evolution of biocatalysts.

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Green chemistry and the environment Directed evolution of enzymes has found many applications in the fields of environmental protection and green chemistry. Soil detoxification and degradation of toxic chemicals are particularly amenable to enzymatic treatments because their elimination by classical means often generates chemical byproducts that are environmentally noxious. Furukawa and collaborators applied the combined approaches of site-directed mutagenesis and Family Shuffling™ of genes to broaden the recognition spectrum of biphenyl dioxygenases [5]. The resulting mutated enzymes recognize and degrade many stable chemical pollutants, notably PCBs but also aromatic hydrocarbons such as benzene and toluene. Modified enzymes are also increasingly used toward industrial purposes that exploit their clean and environmentally friendly usage compared to other catalysts that are damaging to the environment. Thus, enzymes are perfectly adapted to green chemistry applications. A convincing industrial application in this field is the use of proteases in laundry detergents. Proteases such as subtilisin are constantly improved in order to adapt them to the constantly changing and harsh reaction environments of washing machines. Ness et al. have modified subtilisin by Family Shuffling™ using the commercial enzyme Savinase™ as well as other members of the same family of proteases. By creating 654 different random mutants, they selected modified enzymes that displayed up to four times the activity of the native parent with respect to thermostability, pH dependence and the presence of different solvents [6]. This work demonstrates the capacity for directed evolution studies to produce environmentally friendly catalysts with improved catalytic efficiency, a characteristic that strongly influences their industrial profitability.

Conclusion The examples presented here provide a glimpse of the numerous applications where enzymes have been adapted to industrial purposes. Originally confined to biological systems, enzymes are now efficiently modified by directed evolution, which makes them an interesting alternative for environmentally clean industrial processes and green chemistry. Considered of marginal industrial utility even ten years ago, enzyme applications are now growing exponentially because of directed evolution, which makes their application much more flexible, profitable and efficient.

Acknowledgement Figure 1. General strategy for the directed evolution of enzymes (adapted from ref 10)

Pulp and paper, food, and other industrial applications

Organic synthesis and pharmaceutical applications

The pulp and paper industry also benefits from enzymatic catalysts, especially in the bleaching and delignification processes undertaken with the fungal enzyme laccase. Laccase expression in systems more practical than fungi is inefficient, hampering its production and its industrial profitability. Nevertheless, using directed evolution studies, Bulter et al. [8] expressed laccase in yeast at levels 8-fold higher than had been previously obtained. Moreover, under the conditions tested, they isolated mutants with a 170-fold increase in specific activity with respect to the native enzyme. Since laccase is also useful in the food industry for fruit juice clarification and may be useful for environmental applications in the degradation of polycyclic aromatic hydrocarbons, this progress may prove important for many industrial purposes. Enzymes such as α-amylase, glucoamylase and isomerase are heavily used to convert starch into fructose for the production of corn syrup. However, the necessary steps for this conversion require temperature and pH changes that are not well supported by a-amylase. Directed evolution successfully improved its stability at pH 4.85, a pH so acidic for the native enzyme that its denaturation rate in these conditions is not even accurately measurable [7]. The capacity to create or modify a specific characteristic of an enzyme demonstrates the power of directed evolution techniques for modulating the properties of these catalysts toward different requirements.

To date, organic synthesis has been refractory to use of enzyme catalysts, particularly because of their lack of robustness in presence of organic solvents. Nevertheless, Chen and Arnold [9] have adapted enzymes to these environments by improving the activity of Subtilisin E by three cycles of error-prone PCR to obtain an enzyme that is 256 times more efficient than the native parent in a solution containing 60 percent DMF. This highlights the efficiency of directed evolution in the modification of enzymes for use in reaction media that are considerably different from their natural environment. Modified enzymes can also be applied to organic synthesis for the resolution of racemic mixes, which is very attractive for synthesis of biologically-active compounds in the pharmaceutical and biomedical industries. Reetz and collaborators modified the selectivity of a bacterial lipase for 2-methyldecanoic acid p-nitrophenyl ester using the combined methods of Error-prone PCR and saturation mutagenesis [10]. While the native enzyme gives a two percent enantiomeric excess in favour of the (S)-isomer, one of their mutated enzymes provided a 93 percent enantiomeric excess in favour of the same enantiomer. These two examples highlight the fact that directed evolution of enzymes is paving the way toward their use in organic synthesis. Mutated enzymes might eventually be used to catalyze reactions that are currently hard to perform or simply inaccessible using classical synthesis approaches.

The authors thank Michel Lachance of the CQVB for his helpful suggestions.

References 1 Arnold, F. H., 1998. Accounts of Chemical

Research 31, 125–131. 2 Brakmann, S., 2001. Chembiochem 2, 865–71. 3 Tao, H. and Cornish, V. W., 2002. Curr Opin Chem Biol 6, 858–64. 4 Bull, A. T., Bunch, A. W. and Robinson, G. K., 1999. Curr Opin Microbiol 2, 246–51. 5 Kumamaru, T., Suenaga, H., Mitsuoka, M., Watanabe, T. and Furukawa, K., 1998. Nat Biotechnol 16, 663–6. 6 Ness, J. E., Welch, M., Giver, L., Bueno, M., Cherry, J. R., Borchert, T. V., Stemmer, W. P. and Minshull, J., 1999. Nat Biotechnol 17, 893–6. 7 Shaw, A., Bott, R. and Day, A. G., 1999. Curr Opin Biotechnol 10, 349-52. 8 Bulter, T., Alcalde, M., Sieber, V., Meinhold, P., Schlachtbauer, C. and Arnold, F. H., 2003. Appl Environ Microbiol 69, 987–95. 9 Chen, K. and Arnold, F. H., 1993. Proc Natl Acad Sci U S A 90, 5618–22. 10 Reetz, M. T. and Jaeger, K. E., 2000 Chemistry-A European Journal 6, 407–412. Nicolas Doucet is a PhD student in the département de biochimie of the faculté de médecine. Joelle N. Pelletier, MCIC, is assistant professor in the département de chimie of the faculté des arts et des sciences at the Université de Montréal.

April 2004

Canadian Chemical News 21

You Get What You Pay For! Energy supply and pricing for a sustainable future

anadians enjoy one of the most energy-intensive economies on Earth. This makes life very pleasant indeed in what would otherwise be a cold, dark country for half the year. Much of the country depends, directly or indirectly, on fossil fuel for heat in winter and for air conditioning in summer. The Canadian way of life feeds on mainly fossil-fuelled modes of transportation that move everything people need over vast distances within the country, and connects the nation materially to the rest of the world. Thanks to production agriculture and industrial food processing, our daily bread now “embodies” more fossil energy than solar energy. The reality is, that for all the paper wealth being generated by the so-called knowledge-based economy, the country’s entire post-industrial economy still floats on an “old economy” pool of oil and gas. It’s no wonder that in recent years Canadians have been taken aback by wild swings in the market supply and pricing of gasoline, diesel fuel, heating oil, and natural gas. The Canadian—and U.S.—governments have generally responded to this instability with interventions designed to restore stable low prices for conventional fossil fuels. Even while ratifying the Kyoto accord (which is designed to reduce CO2 emissions), Ottawa is doing everything it can, including ruling out a carbon tax, and exempting the auto industry, to ensure that the oil and gas and automotive industries are minimally affected. While this may be good short-term politics, it is bad economics and lousy environmental policy. And it won’t prevent even steeper price increases in the near future. To avoid a serious energy crisis in coming decades, citizens in the industrial countries should actually be urging their governments to come to international agreement on a persistent, orderly, predictable, and steepening series of oil and natural gas price hikes over the next two decades. The present world energy market

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obscures the true price of hydrocarbon fuels and inhibits the development of alternatives. This argument comes in two parts. The first is neatly summarized in a 1998 report by the Washington-based International Centre for Technology Assessment on “The Real Price of Gas.” The purpose of this report was to quantify the numerous external costs associated with the use of fossilfuelled motor vehicles that are not reflected in U.S. consumer prices. Such hidden costs range from various tax and direct subsidies

The present world energy market obscures the true price of hydrocarbon fuels and inhibits the development of alternatives to the oil industry from governments, through publicly funded infrastructure costs, to the health and environmental costs associated with burning fossil fuels (such as breathing second-hand exhaust). These direct and indirect subsidies seriously distort energy markets, burden the economy with rampant inefficiencies, and in the process, are helping to destabilize the world’s climate. Depending on the range of subsidies included and the quality of available data, the total unaccounted cost of fossil fuel use

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William E. Rees in the U.S. was found to lie between $559 billion and $1.7 trillion dollars annually. A fuller social cost accounting for the use of fossil fuel would therefore result in a gasoline price per gallon of between US$5.60 and US$15.14. In Canadian terms, this would be roughly equivalent to a price per litre of between CAN$2.20 and CAN$5.95, or three to nine times the recent Vancouver prices. In other words, even with the burden of existing taxes, prevailing energy prices do not “tell the truth” about the costs of using fossil energy. North Americans pay a fraction of the price they would pay for gas in a perfectly functioning market. In fact, U.S. consumers enjoy the most under-priced fuel available in any major industrialized country and Canadians are really not that far behind—with predictable results. As every economist knows, the invariable consequence of under-pricing is overuse. Wealthy and middle-class North Americans live in ever-larger energy-inefficient houses, drive ever-bigger and less fuel-efficient vehicles and are therefore squandering in a few decades a non-renewable resource that took tens of millions of years to accumulate. Even if there were no other issues at hand, it would be economically rational and ecologically beneficial for our federal governments to intervene in today’s energy market to correct at least the best-documented and non-controversial market imperfections. For example, priceinduced lower consumption would help Canada meet its Kyoto commitment. We should be paying significantly greater prices and taxes at the pump. But there is another issue at hand. The world is running out of cheap oil and North America is looking at dwindling reserves of gas. Recent price hikes may be mere tremors heralding the real price shock to come. Surely this is not the time to be discouraging the development of alternative energy sources and deepening our dependence on fossil fuel.

The evidence? Oil production (or extraction) peaked in the U.S. around 1970 and in North America as a whole in 1984. Extraction from North Sea fields peaked in 2000 (only 25 years after peak discovery) and is now also in decline. More than 50 other oil“producing” countries have already gone through this cycle of discovery, peak extraction and decline so that non-OPEC production is approaching its aggregate peak even as this is being written. Indeed, several recent studies project global conventional oil production to peak as early as 2010. Harry J. Longwell, executive vicepresident of Exxon Mobil, made an unprecedented admission recently when he wrote, “To put a number on it, we expect that by 2010 about half the daily volume needed to meet projected demand is not on production today—and that’s the challenge facing producers” (Longwell 2002). Even the necessarily conservative International Energy Agency (IEA) in its World Energy Outlook, (1998) concurred for the first time that global output could top out between 2009 and 2012 and decline rapidly thereafter. Indeed, the IEA projected a nearly 20 percent shortfall of supply relative to demand by 2020 that will have to be made up of from “unidentified unconventional” sources. Known oil-sands deposits such as those being developed in Alberta have already been taken into account. Other studies show that by 2040 total oil and natural gas liquid output from all sources may fall to 60 percent of today’s 25 billion barrels of oil equivalents per year. And running out of oil is not running out of just oil. Oil is the means by which industrial society obtains (and exploits) all other resources. The world’s fishing fleets, its forest sector, its mines, and its agriculture all are powered by liquid portable fossil fuels. Seventeen percent of the U.S. energy budget, and most of it oil, is used just to grow, process, and transport food alone. Physicist Albert Bartlett of the University of Colorado has called modern agriculture “the use of land to convert oil into food.” Keep in mind, too, that petroleum is not just a fuel. Oil and natural gas are the raw material for thousands of products from medicines, paints, and plastics to agricultural fertilizers and pesticides. Since oil is directly or indirectly a part of everything else the coming scarcity of oil and the attendant price shock may mean higher prices for everything else as well. Many analysts will agree with energy economist M. A. Adelman that rising prices will stimulate “... a stream of investment

[creating] additions to proved reserves, a very large in-ground inventory, constantly renewed as it is extracted.” Unfortunately, this argument is dangerously misleading. The physical stock of exploitable oil is not being “renewed” and while higher prices have stimulated more drilling, they have not “added to proved reserves” in net terms since the early 1980s. To complicate matters, improved technology does make dwindling finite reserves more accessible

Running out of oil is not running out of just oil thus increasing short-term market supply. Unfortunately, this effectively short-circuits the price increases that would otherwise signal impending real scarcity, even as finite stocks are depleted. Adelman’s argument also ignores the fact that oil exploration is subject to diminishing material returns. Despite increasing effort, we typically discover only six to eight billion barrels of new oil per year, or between a quarter and a third of present consumption. A few decades ago, oil extractors in the U.S. would discover 50 barrels of oil for every barrel consumed in drilling and pumping. In the mid-1990s the ratio fell as low as five to one. While the ratio fluctuates, the trend in older oil producing regions is downward. At some point, there will no point in extracting oil with oil at any price even though there will still be plenty left in the ground. What about substitutes? Concerns over climate change have already stimulated a growing interest in alternative energy sources. However, there are problems on the supply side. A recent summary article on energy engineering in Science cautioned that most renewable alternative sources of energy suffer from low aerial power densities, intermittent supply, and other severe deficiencies that limit their ability to replace fossil fuels. Biomass, wind power, and solar, for example, produce relatively few watts of power per unit area compared to the chemical energy concentrated in fossil fuel. For these and other reasons, a recent issue of The Energy Advocate argued rather bleakly that, “The renewable sources of energy— direct sunlight, wind, hydropower, biomass—are all solar in origin and are in toto inadequate for running anything that

passes for civilization. “They have” no chance whatsoever of sustaining the present world’s population.” While not all analysts agree with that grim prognosis, it has yet to be confidently refuted and there are still other problems. We sometimes forget that qualitative differences among energy types make them imperfectly substitutable. Wind-generated and photovoltaic electricity may be able to substitute for most of the electricity currently generated by fossil fuels (nuclear fission is still in disrepute and commercial fusion reactors are decades in the future). However, electricity cannot replace the direct use of petroleum derivatives as fuel nor overcome their clear advantages in energy storage. While there may be promise in fuel-cells if we can discover a way to produce hydrogen efficiently, the fact is that no suitable substitutes are yet in sight for the fossil fuels used in heavy farm machinery, construction and mining equipment, diesel trains and trucks, and ocean-going freighters. Jet aircraft cannot be powered by electricity, whatever its source. Nothing can replace hydrocarbons as feedstocks in the manufacture of myriad industrial and agricultural products. Finally, it is no small irony that we need high-intensity fossil fuel to produce the machinery and infrastructure required for most alternative forms of energy. Sunlight is simply too “dilute” (remember, “low energy density per unit area”) to use in manufacturing the hightech devices and equipment required for its own conversion to heat and electricity. Industrial civilization faces a paradox: we need oil to move beyond the age of oil. The human population has grown sixfold in less than 200 years. The global economy has quintupled in less than 50. No factor has played a greater role in this recent explosive growth of the human enterprise than abundant cheap fossil fuel. No other resource has changed the structure of economies, the nature of technologies, the balance of geopolitics, and the quality of human life as much as petroleum. Little wonder that some scientists believe that passing the peak of world oil production will be a shock to the human enterprise like no other event in history. Population and consumption are still on a steep trajectory but the rocket is running out of fuel. The problem is solvable, but not without positive action and wide-ranging policy innovation. Certainly universities should be leading the way in performing the research required to make alternative energy work and in on-campus energy-conservation

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Canadian Chemical News 23

demonstration projects. Meanwhile informed ordinary citizens and public service organizations in Canada and the U.S. should be urging governments to get real about energy policy, including pricing. As a first step, all direct and indirect subsidies to conventional oil and gas producers must be eliminated. Subsidies keep fossil fuel prices artificially low, encouraging excess consumption and inhibiting the development of alternatives. Secondly, we should be moving closer to full social cost pricing of fossil energy through carbon taxes or resource depletion taxes—as noted, significant price increases for conventional fuels are long overdue. Eventually, if alternative energy development continues to lag, it may be necessary to implement a quota system for remaining fossil reserves. This would slow the pace of fossil energy consumption to ensure there is sufficient conventional energy supply to bridge the transition to the post-petroleum era. Government agencies would determine the annual allowable quota for crude oil and raw gas based on the best available science and analyses; competitive bidding among resource companies would then set a fair and efficient market price for the available supply. More realistic prices for traditional fuels are needed to induce conservation of our remaining fossil fuel reserves, to encourage the private sector to develop more energyefficient technologies (particularly in the auto and transportation sector generally, building technologies and appliances), and to make inherently more expensive but necessary alternatives more competitive. Keep in mind too that more realistic pricing would help make the entire economy more

Tell us what YOU think! Send your comments on this article to

editorial@accn.ca

24 L’Actualité chimique canadienne

efficient and competitive as the world energy market tightens up. It could be argued that higher energy costs would impose an unfair burden on low-income families. Certainly any such inequity must be avoided but without abandoning the overall energy policy objective. (Failure to act now might mean an even greater future burden on the poor.) On the positive side, note that this potential problem might be relatively short-lived if the policy changes are phased in properly, according to a predictable schedule. Both producers and consumers respond to higher costs and prices. People would not object too much about gasoline costing twice as much if their cars were twice as fuel-efficient (and they’d have to become more fuel efficient if their manufacturers hope to retain market share). In any event, changes to energy pricing policy would be part of a broader program of ecological fiscal reform. Even income taxes rates could be adjusted to compensate for any residual inequity resulting from rising energy and material costs (dare we discuss a negative income tax?). Finally, keep in mind that many advanced European countries already have much higher energy costs than we do in Canada. They have already made many efficiency adjustments with no appreciable negative distributional impacts. The data and trends in the energy sector are no secret. Governments have known about the deteriorating conventional supply situation for years yet tend to sacrifice the public interest to the interests of the oil and gas and automotive industries who lobby for the status quo. Or they remain in the thrall of conventional economists who still argue— against the evidence of recent decades—that rising prices will automatically lead to adequate new discoveries. All this creates a political climate in which the looming crisis remains invisible and corrective action (with the possible exception of an oil-related war in Iraq) is impossible. The point is that higher energy prices are needed now to signal the real scarcity to come. Without higher prices we will not invest in the technologies needed for a smooth transition to the postpetroleum age. Without higher prices we will not conserve the fossil energy needed to manufacture those alternative technologies. As energy analyst Richard Duncan has frequently argued, without higher prices, the remaining life expectancy of industrial society may well be less than 40 years!

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Acknowledgement An earlier version of this article appeared in the CCPA Monitor, June 2003.

References and additional reading Adelman, M. A. 1993. The Economics of Petroleum Supply. Cambridge, MA: MIT Press. Campbell, C. C. 1999. The Imminent Peak\of World Oil Production. www.hubbertpeak.com/campbell/ commons.htm. Duncan R. C. 1993. “The Life-expectancy of Industrial Civilization: The Decline to General Equilibrium,” Population and Environment 14: 325–357. Duncan R. C. and W. Youngquist. 1999. “Encircling the Peak of World Oil Production,” Natural Resources Research 8 (3) 219–232. The Energy Advocate, August 1996. Fleming, D. 1999. “Decoding a Message About the Market for Oil,” European Environment 9: 125–134. Hoffert, M. I., et al. 1992. “Advanced Technology Paths to Global Climate stability: Energy for a Greenhouse Planet,” Science 298: 981–987, November 2002. International Energy Agency.1998. World Energy Outlook. Laherrere, J. 2003. “Forecast of oil and gas supply to 2050,” Paper presented to “Petrotech 2003,” New Delhi. Longwell, H. J. 2002. “The Future of the Oil and Gas Industry: Past Approaches, New Challenges,” World Energy 5: 3: 102–105. Youngquist, W. 1997. GeoDestinies. Portland: National Book Company. Youngquist, W. 1999. “The Post-Petroleum Paradigm—and Population,” Population and Environment 20(4): 297–315.

William E. Rees is an ecologist and ecological economist and professor in the University of British Columbia’s School of Community and Regional Planning.

New and (Already) Improved! A report on the first IUPAC International Conference on Bio-based Polymers (ICBP 2003) Robert H. Marchessault, FCIC, and Jumpei Kawada, MCIC early ten years ago, Canadian Chemical News/L’actualité chimique canadienne (ACCN) carried a report on the ISBP 1994 International Symposium on Bacterial Polyhydroxyalkanoates, PHAs. The headline read, “International Conference Discusses the Future of Biodegradable Thermoplastics.” While the objective has not changed and the same players are involved—biodegradable products are greatly expanded and now include many synthetic biodegradables. Yoshiharu Doi, the conference chair, opened the first IUPAC International Conference on Bio-based Polymers with this statement: “Bio-based polymers include various synthetic polymers derived from renewable resources and CO2, biopolymers (nucleic acids, polyamides, polysaccharides, polyesters, polyisoprenoids and polyphenols), their derivatives, and their blends and composites. Fossil resources are limited, while renewable resources are sustainable. In the last few years, science and technology on bio-based polymers have experienced a tremendous rise in significance. The biobased polymers have become important at both the academic and industrial research centres.” The biodegradability target has expanded from microbial polyesters to include all types of plastics as long as they are friendly to the environment. The recent book by E. S. Stevens, Green Plastics, published in 2002 by Princeton University Press is a good layperson’s primer on this subject, although most of the 240 registrants (2/3 from Asia) were already “green plastics” enthusiasts.

Life cycle of PHAs Microbial polyesters are part of the natural biosynthesis/biodegradation cycle, hence they respond to present requirements for biodegradable materials as shown below.

These biopolyesters have been a model system for learning about biodegradable thermoplastics but have failed to satisfy all possible needs and especially large scale production’s requirements. The January 2004 issue of Canadian Chemical News / L’Actualité chimique canadienne (ACCN)

Bacteria can accumulate PHAs, such as poly(3-hydroxybutyrate-co-3-hydroxyvalerate), as carbon reserve. The PHAs are extracted from the cell and are utilized for commodities, such as shampoo bottles, golf tees, fibres, plastic bags, and so on. These items are quickly and easily degraded by soil enzymes when they are thrown away to nature. The enzymes can break them down into small molecules which are the very food for bacteria to produce the PHAs, again.

had a lead article on the Cargill-Dow Nature WorksTM poly(lactic acid), PLA, a synthetic biodegradable derived from fermentation of starch to lactic acid, its production by ringopening polymerization of the lactide, recycling, etc. Large scale production of PLA leaves the bacterial polyesters on the starting blocks, at least for now. However, the storehouse of microbial knowledge concerning this manner of bioplastics production will probably see its future in production using transgenic plants.

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Canadian Chemical News 25

Biodegradable synthetic plastics

Polymer trade name

In Japan, companies such as Toyota Automotive, Mitsui Chemicals, and others are committed to the PLA technology and not PHA. The reason being is the natural fibre or clay/polylactide biocomposite that is a major development in Europe, Asia, and the U.S. to replace the non-sustainable polyolefins in automobile parts. Along with this effort goes the “biorefinery” that implies cracking of natural raw materials to make valuable chemicals, many of which are not possible with present day petroleum refining. Both fundamental and focused research on polylactides is replacing the former effort on PHA. For the automotives, the specific objective is to fabricate some of the 200 or more compression molded components inside the cabin of an automobile with sustainable biodegradable plastics. Biodegradability is not the exclusive feature of natural polymers. An increasing number of synthetic plastics mimic this “green chemistry” characteristic. It is not only the source of the polymer that confers biodegradability, equally important are texture, conformation, and the aliphatic ester or amide comonomers. The latter seems to be the trigger for initiating biodegradation in synthetic biodegradables. Thus, BASF’s EcoflexTM, a synthetic biodegradable halfaromatic polyester, is a random copolymer based on 1,4-butanediol and a mix of terephthalic acid and adipic acid. The aliphatic components, reminiscent of PHA biopolyesters, are prominent in the successful synthetic biodegradables. For example, BionolleTM, a product of the Showa High Polymer Company is poly (tetramethylene succinate) with biodegradability characteristics comparable to the microbial polyesters. Other successful synthetic biodegradable thermoplastics are listed in the table. Thus, the meaning of “bio-based” in the title of this article refers to a chemical class of polymers that mimic nature’s biopolymers. The mature chemical processing of the synthetic polymer industry will often use biomass fermentation to ensure a sustainable plastics industry. The Biosynthesis-Biodegradation Cycle of PHA is a model where fermentation is the source of the biodegradable plastics. PLA products are based on a combined agro-fermentationchemistry paradigm. Bio-based polymers for value-added applications such as drug delivery or compatible bone cement can be synthesized/biosynthesized with comb-like

26 L’Actualité chimique canadienne

Ecoflex (BASF)

Biomax (DuPont)

CelGreen PH (Daicel Chemical Industry Ltd.)

Composition Biodegradable aliphatic- aromatic copolyester: Terephthalic acid (22%), 1,4-butanediol (50%) and adipic acid (28%) Hydro/biodegradable aliphatic-aromatic copolyester: ethylene glycol, diethylene glycol 85% terephthalic acid ~ 15% adipic acid sulfo isophthalic acid Homopolyester: Poly (ε-caprolactone)

LACEA/Nature WorksPLA (Mitsui Chem. Corp/Cargill Dow Polymer)

Homopolyester: Poly(L-lactic acid)

Bionolle (Showa Highpolymer Co.)

Biodegradable aliphatic polyester: Poly(tetramethylene succinate)

or block-like textures. New blends and copolymer compositions of PHAs such as Procter and Gamble’s NodaxTM, a copolymer of butyrate/hexanoate repeat units [poly(3-hydroxybutyrate-co-3-hydroxyhexanoate)], were described at the conference.

Conclusions Of the six classes of biopolymers mentioned by Doi in his opening statement only polyesters were prominent in the program. This is in keeping with the ease of chemical synthesis of commercial polyesters. Polyolefins were only present as blends with starch; in spite of the natural abundance of polyisoprenoids, natural rubber was not mentioned. Polyphenols (which can be called lignins) are equally abundant, but their variable structure is too much of a challenge for controlled polymer synthesis. The oral presentations will be published in a special issue of Macromolecular Bioscience later in 2004. The final lectures of the meeting were dedicated to presentations by organizations such as the Biodegradable Plastics Society of Japan (BPS). They have a trademark “GreenPla” that has guidelines for product approval and wide industrial membership. In the U.S., the Biodegradable Products Institute (BPI) is the equivalent. Products such as “starch loose fill, raincoats from unwoven poly lactic acid, PLA microwaveable

avril 2004

trays, etc.” are blazing the publicity trail. Life cycle analyses were prominent in these lectures. This was an outstanding meeting, a rallying cry for much broader biopolymer perspective than was provided by ISBP meetings alone. The research activities in polylactide seem to have a distinct edge for commercial development. The most prominent PHA “push” was for Procter and Gamble’s P(3-hydroxybutyrate-co-6mol%-3-hydroxyhexanoate) from vegetable oil fermentation. Many academic researchers at the conference believe PHAs are the best candidate for the thermoplastic due to the sustainability—in other words— the ideal biosynthesis-biodegradation cycle. However cost and productivity problems are still formidable compared with PLA or other synthetic biodegradables. In contrast, industrial researchers favour PLA in terms of availability and price. At the 1994 ISBP meeting, the PLA success was not anticipated. Technology advances have allowed large scale production. Will the next decade bring the same success for PHAs and other bio-based materials? Robert H. Marchessault, FCIC, is the E.B. Eddy professor, and Jumpei Kawada, MCIC, is a postdoctoral fellow. They both hail from the department of chemistry at McGill University.

New Bleaching Agents for Mechanical Pulps A discovery made possible by the pursuit of green chemistry

In 2000, the Canadian pulp and paper industry contributed over $21 billion to Canada’s $54 billion merchandise trade balance and directly employed about 67,000 people. Technical innovation in processes used for the production of pulp and paper will have a significant impact on the Canadian economy.

Canada— the world’s biggest producer of mechanical pulp To make paper, wood (in the form of wood chips or sawmill residue) is first converted to chemical or mechanical pulp by a pulping process. Chemical pulp is produced in a yield of 45 to 55 percent through the dissolution of wood lignin by pulping chemicals, for example, NaOH and Na2S, at elevated temperatures (> 160 °C). Mechanical pulp is formed with retention of lignin in a yield of 90 to 98 percent mainly through the action of mechanical forces on wood. Canada is the biggest manufacturer and exporter of mechanical pulp in the world, producing ~ 11 million metric tons per year, or one-third of the total world production of such pulps.

Bleaching of mechanical pulp Mechanical pulp has a pale-yellow colour similar to that of natural wood due to the presence of lignin chromophores such as coniferaldehyde (see Scheme 1). Removal or modification of these chromphores (i.e. bleaching of the pulp) is often needed prior to papermaking. Two bleaching agents, alkaline hydrogen peroxide (HOO-) and sodium dithionite (Na2S2O4) have been used by the industry for over half a century. The former, in the presence of the peroxide stabilizers sodium silicate and magnesium sulfate, removes most of the lignin

Thomas Q. Hu, MCIC, and Brian R. James, FCIC Discovery of a new class of bleaching agents

chromophores and bleaches the pulp to high brightness. However, peroxide also degrades the cellulose and hemicelluloses, thus reducing the pulp yield by 2 to 5 percent and producing effluent with a high content of dissolved organics. The latter is a more selective bleaching agent because of its reductive nature. However, dithionite is less effective and generates various sulfur-containing chemicals including thiosulfate that is corrosive to paper machines. Neither of these two bleaching agents in terms of modern parlance is “atom efficient” or “green.”

Among the many catalysts we have synthesized and studied over the past few years, the most promising one was a H2O-soluble, ruthenium (Ru)-phosphine complex prepared from the reaction of RuCl3. 3H2O and tris(hydroxymethyl)phosphine (THP), P(CH2OH)3. An in-situ prepared Ru-P(CH2OH)3 complex with a P/Ru molar ratio of 3.0 catalyzed the H2-reduction of the -CH=CH-CHO group in coniferaldehyde (O-Lignin = OH, Scheme 1) to mainly the CH2-CH2-CH2OH group under 500 psi H2 at 80 °C in aqueous media. More importantly, when an in-situ prepared Ru-P(CH2OH)3 complex with a P/Ru molar ratio of > 5.0 was applied to the hydrogenation of mechanical pulp, bleaching of the pulp was achieved. Encouraged by these results, THP complexes of cheaper metals such as copper (Cu) were studied. When mechanical pulp were treated with 340 psi H2 in the presence of the zwitterionic Cu(I)-THP complex, [Cu{P(CH2OH)3}3{P(CH2OH)2(CH2O-)}], and THP at 80 °C, bleaching of the pulp was obtained. Subsequently we found by control experiments that neither H2 nor Cu was needed for the bleaching effect, and

Our green chemistry approach Supported earlier (1995 to 2000) by NSERC via the NCE Mechanical and Chemimechanical pulp Network, and funded recently (2001 to present) by an NSERC Strategic Project Grant, we have pursued actively the catalytic H2-hydrogenation of lignin chromophores such as coniferaldehyde (Scheme 1) as a reductive and “green” bleaching and brightness stabilizing method for mechanical and chemical pulps. The biggest challenge of our work has been the development of a H2O-soluble, recyclable and robust catalyst capable of affecting the hydrogenation in aqueous media.

H H

O H

H H2

H H

O H

H H H

H H

OH H H H H

Catalyst OMe O

OMe

Lignin

OMe

O Lignin

OH H H H H H H H H H H H OMe H O Lignin H

H H

Lignin coniferaldehyde

Scheme 1

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Canadian Chemical News 27

discovered that the phosphine itself was an effective bleaching agent! We also discovered that tetrakis(hydroxymethyl) phosphonium salts such as [P(CH2OH)4]Cl (THPC) and [P(CH2OH)4]2SO4 (THPS) (see Scheme 2) were equally effective. Furthermore, pulp bleached with these simple, H2O-soluble P-containing compounds showed improved brightness stability when exposed to heat and high moisture. The P-compounds could also be applied to the surface of paper made from mechanical pulp to provide the paper with improved light-stability.

pulp and water mixture. Such a temperature, consistency and pH tolerance is unprecedented in the field of pulp bleaching, and very attractive to pulp mills where it is often difficult, for example, to control the bleaching of pulp with Na2S2O4 at an optimal pH of 5.5 to 6.5, because of the pH changes caused by the hydrolysis or oxidation of Na2S2O4, and because of the increasing recycling of mill process water with high contaminant levels. We have also identified derivatives of THP and THPS with a bleaching power higher than that of Na2S2O4 and approaching that of alkaline hydrogen peroxide. The derivatives

OH HO

P OH (THP)

Cl-

SO422

(THPS)

(THPC)

Scheme 2

Characteristics and potential of the new bleaching agents THP, THPC and THPS have a bleaching power similar to that of Na2S2O4. However, they can be used over a much wider range of temperature (20 - 130 oC), consistency (e.g. 1.5 percent to 40 percent) and pH (4.5 to 9.5). “Consistency” is the weight percentage of pulp in a

28 L’Actualité chimique canadienne

can bleach pulp that are difficult to bleach with Na2S2O4, and they can substitute ~ 70 percent of the alkaline hydrogen peroxide needed to bleach mechanical pulp to high brightness. Preliminary studies by UV-visible spectrometry show that the new bleaching agents are effective in reducing/removing the C=O groups in lignin model chromophores.

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THPC and THPS are commercially available in large quantities (> 103 tons/annum) and are produced in one-step from the commodity chemicals, phosphine (PH3), formaldehyde and sulfuric acid. THP salts have been used for decades as a basic chemical to make flameretardants for cotton, cellulose and cellulose-blend fabrics. The use of THPS as an environmentally benign biocide for sulfatereducing bacteria in non-food papermaking has also been approved by U.S. EPA. We have filed PCT and U.S. patent applications on the use of the various P-compounds and issued a Paprican-University Research report to Paprican’s Member Companies. The response from these companies has been overwhelmingly positive. We are currently trying to illustrate the bleaching chemistry of the P-compounds, identify additional values they can bring to a pulp mill, and determine their commercial feasibility. We are optimistic that a new and greener bleaching technology for mechanical pulp will develop from our discovery of the unique bleaching abilities of THP, THPC and THPS. Thomas Q. Hu, MCIC, is a scientist at the Pulp and Paper Research Institute of Canada (Paprican) and an adjunct professor in the chemistry department at the University of British Columbia. Brian R. James, FCIC, is an emeritus professor in the chemistry department at the University of British Columbia. They can be reached at thu@paprican.ca and brj@chem.ubc.ca.

N O I T N U O L I L O P EVENT PR

in the PRINT and PULP and PAPER INDUSTRIES

The three Ps go “green” and clean up their acts! CleanPrint Canada leanPrint Canada is a non-profit partnership comprised of representatives from all aspects of the printing industry including printers, suppliers, associations and government. Participation and implementation of projects is completely voluntary. The web site provides an opportunity to distribute and publish information to inform other printers on different opportunities to reduce pollution and often save money. The various representatives work together and support one another to: • identify and implement various types of pollution prevention projects; • test and operate new technologies or systems (environmental management systems); share successes and discuss issues and challenges; • improve energy efficiency; • increase recycling and reuse of materials; • reduce water consumption; and • to reduce both hazardous and nonhazardous waste generated. Ontario and British Columbia have the two most active regional committees in Canada, however, most provinces have had some level of involvement in a printing and graphics sector pollution prevention project. In Ontario, the current focus is on reducing volatile organic compound emissions from the screenprinting facilities. An Environmental Performance Agreement was recently been signed between Environment Canada and the Specialty Graphic Imaging Association (www.sgia.org) to reduce volatile organic compound emissions by 20 percent and carbon dioxide emissions by 3 percent from the screenprinting plants throughout Ontario. Additional details and other reduction goals regarding this agreement can be found on Environment Canada’s Web site www.ec.gc.ca/CEPARegistry/documents/agree/sgia_agree/index_sgia.cfm. The screenprinters participating in the project will be implementing an integrated environmental management system at their facilities to help them identify opportunities for reduction in waste and energy consumption.

The environmental management system can easily be incorporated in the practices and procedures already coordinated by the Health and Safety Committee. The environmental benefits often improve the work conditions for the employees. Several companies are already in the process of converting from a solvent based ink system to an ultra violet technology and demonstrating significant VOC reductions and improved employee moral due to the reduced amount of fumes inhaled. In previous years the pollution prevention printing project in Ontario focused on lithographic sector. As a result of this past project, many success stories describing how reductions in the use of toxic materials and reduced emissions were achieved have been described and are available from the CleanPrint web site www.cleanprint.org. The British Columbia Regional Committee has developed several useful tools that are available for free from the CleanPrint web site including: best management practices posters and checklists, and a how-to guide for preparing an environmental management plan which can be used by flexographic, screenprinters and offset printers. Environment Canada Ontario Region has developed procurement guidelines for purchasing paper and printing services. Currently there is a requirement that paper purchased must contain a minimum of 30 percent post consumer waste. Printing services which are contracted to print government documents must meet the environmental criteria described by the Environmental Choice Program www.environmentalchoice.ca. The criteria is intended to encourage companies to reduce their environmental impact and outline the performance characteristics that a printing company should achieve. Companies have the option of participating in the environmental certification program but it is not mandatory requirement for securing print contracts but they must prove they do meet the standards. The standards describe the use of inks containing a reduced quantity of harmful ingredients (heavy metals and VOCs), the process must minimize its use of water and ensure that wastewater is directed to sewage treatment facilities that meet strict quality requirements. For further information on CleanPrint Canada contact: Sheelagh Hysenaj, Pollution Prevention Officer at Environment Canada at 416-739-5910.

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Canadian Chemical News 29

Environment Canada’s Pollution Prevention Success Stories Web Site Go to www.ec.gc.ca/ppto see examples of pollution prevention stories in action. The success stories are designed to recognize Canadian organizations, companies, and individuals who are making a difference in pollution prevention. The site shows the economic benefits of industry’s efforts to “Keep Clean” as well! It provides an incentive for Canadians to adopt practices similar to those featured in the stories. Take a look at these two Pollution Prevention Success Stories from Canada’s pulp and paper industry:

Millar Western Pulp (Meadow Lake) Ltd. he start-up of Millar Western’s Meadow Lake bleached chemi-thermo-mechanical pulp (BCTMP) mill in Edmonton, AB in 1992 marked the world’s first successful implementation of zero-liquid-effluent-discharge technology at a market pulp facility. A totally chlorine-free operation, the Meadow Lake mill generates no chlorinated dioxins, chlorinated furans or other chlorinated organics. Millar Western monitors each pulp run to find ways to decrease both chemical and electricity use. According to the Canada Pulp and Paper Association’s 1997 Energy Monitoring Report, Millar Western had the lowest purchased-energy rates of all mechanical pulp mills in Canada. Work is also being done on recovering the fibre that is lost through various processes (such as the debarking of logs) in order to maximize fibre usage.

Benefits Environmental Millar Western’s Meadow Lake mill uses approximately 10 times less fresh water than conventional BCTMP mills and 40 times less than conventional kraft mills. This mill produces 60 to 100 percent more pulp per tree than kraft mills, resulting in fewer trees being harvested per tonne of pulp. Hydrogen peroxide is used to bleach the pulp, avoiding the generation of chlorinated dioxins, chlorinated furans or other chlorinated organics.

Economic Decreased production costs have resulted from efforts to reduce and reuse solid wastes and minimize energy and chemical use. Production costs from this zero-liquid-effluent-discharge pulp mill are comparable with those of conventional BCTMP mills.

Recognition In 1993, the Meadow Lake mill was awarded the Saskatchewan Achievement for Business Excellence Award for the Physical Environment. In 1998 Meadow Lake achieved ISO 14001 certification of its environmental management system. To learn more about Millar, visit www.millarwestern.com

The totally chlorine-free Millar Western Pulp (Meadow Lake) mill is the world’s first successful zero-effluent-discharge market pulp mill.

30 L’Actualité chimique canadienne

avril 2004

World of difference. Many improvements distinguish the Tembec Mill of 1927 shown at left and the new Mill shown above in 2002.

Tembec Paper Groupâ&#x20AC;&#x201D; Pine Falls Operations embec-Pine Falls Operations in Pine Falls, MB produces newsprint for major newspapers in Canada and the U.S. Tembec is Manitobaâ&#x20AC;&#x2122;s only newsprint mill and is the largest recycler of old newspapers and magazines in the province. The installation of a deink facility in 1995, allows Tembec to use 100 tonnes per day of old newspapers and magazines in the pulping process. From 1927 to 2001, the Pine Falls mill produced pulp for its newsprint operation using a mix of stone groundwood and sulfite processes. Groundwood pulping uses large stone grinders to grind logs into pulp while the sulfite process essentially digests the wood fibres into pulp using a cooking liquor. Pine Falls was one of very few pulp and paper mills left in North America using such technology. In March 2001, the mill underwent a major change in the pulp production process to improve the quality characteristics of the newsprint sheet, reduce operating costs and improve environmental performance of the mill. The two older pulping technologies were shut down and a new, and state of the art $124 million theromechanical pulp (TMP) mill was commissioned. The new facility uses heat and pressure to break down wood fibre into pulp. The heart of the process involves 35,000 horsepower motors to drive refiners, which break up the fibre in wood chips into pulp. The process generates a significant amount of heat, which is captured by a sophisticated heat recovery unit. This heat is then used to generate steam for use in other parts of the mill.

Benefits Environmental The shutdown of the sulfite pulping department has eliminated the generation of sulfur odours and greatly reduced SO2 emissions from the mill facility. The heat recovery unit has reduced coal use in the powerboilers by more than 50 percent, thereby reducing air emissions significantly. This will allow the company to attain a 50 percent reduction in greenhouse gas emissions below the 1990 baseline. The use of wood waste generated from the TMP and log chipping operation as a biomass fuel in the boilers also contributes to the reduction of greenhouse gas emissions. TMP-related effluent improvements include a 63 percent reduction in Biochemical Oxygen Demand, 84 percent reduction in Total Suspended Solids and a 90 percent reduction in Chemical Oxygen Demand. The use of old newspapers and magazines has reduced the need to harvest the forest by almost 25 percent.

Economic The automated nature of the new TMP plant has resulted in a significant cost savings to the company. The TMP will substantially reduce production costs, thereby securing the long-term future of the mill in Pine Falls. The TMP will put Tembec-Pine Falls into the top 10 percent among low-cost newsprint producers in North American by reducing costs by an estimated $80/tonne. In addition, the TMP will greatly improve the quality characteristics of the newsprint sheet that is produced. To learn more about Tembec, visit www.tembec.com

Does your company or institution practice

POLLUTION PREVENTION? Submit your own story to info@c2p2ponline.com. See the Web site for desired criteria. Printed with permission from Environment Canada. April 2004

Canadian Chemical News 31

CIC Bulletin ICC Section head

Announcing the 2004 CIC Fellowships The nine members of The Chemical Institute of Canada profiled below were elected to the Fellowship in 2004 by the CIC Board of Directors. They will receive their Fellowship certificates either at the CIC Annual General Meeting (AGM) in London, ON, on May 31, 2004, or at the CSChE AGM to be held in Calgary, AB, this October. A reception will be held in honour of the new Fellows immediately following the CIC and CSChE AGMs. These Fellowship recipients now carry the designation FCIC on their name, replacing MCIC. Congratulations are extended to the following new members:

Thomas A. Duever Professor and chair of chemical engineering, University of Waterloo, Waterloo, ON PhD, University of Waterloo, 1987 Member of the CIC since 1988 Nominated by Alexander Penlidis, FCIC, University of Waterloo

Philip R. Bunker Principal research officer, National Research Council Canada, Ottawa, ON PhD, Cambridge University, 1965 Member of the CIC since 1996 Nominated by Tucker Carrington, FCIC, Université de Montréal

Mississauga, ON PhD, University of Western Ontario, 1972 Member of the CIC since 1979 Nominated by P. R. Sundararajan, FCIC, Carleton University

Molecular Symmetry and Spectroscopy, co-authored with Per Jensen and Computational Molecular Spectroscopy, co-edited with Jensen.

Thomas Duever is distinguished for research on the application of statistical methods for chemical process analysis, which has resulted in models and estimation of parameters for predicting polymer process behaviour, and in the calculation of reactivity ratios in polymer reaction systems. He has also made important contributions to the CIC through his activities in the CSChE and in the teaching of chemical engineering.

Philip Bunker has made outstanding contributions to research in theoretical spectroscopy for 40 years, specifically in the breakdown of the BornOppenheimer approximation, the dynamics of highly flexible molecules and in the discovery and analysis of spectra of triplet and singlet methylene, as described in 165 papers. He has had a major impact on spectroscopy through his books

32 L’Actualité chimique canadienne

Edward P. C. Lai Professor of chemistry, Carleton University, Ottawa, ON PhD, University of Florida, 1982 Member of the CIC since 1985 Nominated by Jean-François Legault, MCIC, National Defence and president of the CSChE Board of Directors Edward Lai has made substantial contributions to the analytical chemistry of biochemical and environmental materials by using such novel techniques as nonasecond laser spectroscopy, surface plasmon resonance, time-of-flight spectrometry and electrochromatography, resulting in new photochemical, electrochemical, optical, and molecular recognition phenomena. His achievements in teaching and in CIC and CSC activities at local and national levels are also noteworthy.

Rafik Loutfy Corporate vice-president, Xerox Corporation,

avril 2004

Rafik Loutfy has been outstanding in research on photochemistry, electrochemistry, and pigment science and technology, as applied to solar cells, photoreceptors, and xerography, all described in 165 papers and 43 patents. His CIC and CSC activities, fostering industry-university interactions and management of science and technology have been exemplary.

Derek C. G. Muir Research scientist, Environment Canada, Burlington, ON PhD, McGill University, 1977 Member of the CIC since 1980 Nominated by James Maguire, FCIC, Environment Canada Derek Muir is an international expert on environmental chemistry, including the bioaccumulation and bioavailability of persistent organic pollutants in the aquatic environment, especially of Northern Canada. His research work, described in over 200 publications, is having a major impact on national and international initiatives to identify and control these pollutants.

CIC Bulletin ICC Section head

University of British Columbia, Vancouver, BC ScD, Massachusetts Institute of Technology, 1989 Member of the CIC since 1989 Nominated by Paul Watkinson, FCIC, University of British Columbia

Flora T. T. Ng Professor of chemical engineering, University of Waterloo, Waterloo, ON PhD, University of British Columbia, 1970 Member of the CIC since 1990 Nominated by Thomas Fahidy, FCIC, University of Waterloo Flora Ng is making significant contributions to fundamental and applied aspects of both homogeneous and heterogeneous catalysis. Her world-class research on catalytic distillation has made a major impact in the field of green reaction engineering and process intensification. Ng has contributed to BP Chemicals, (U.K.) award-winning process for the production of ethyl acetate on a huge scale. She is an excellent mentor and a role model to many female students.

James M. Piret Professor of biotechnology laboratory and chemical and biological engineering,

James Piret is distinguished for major achievements in stem cell research, hollow fibre bioreactors for monoclonal antibody production, recombinant protein production, and the development of an acoustic filter for retention of cells from bioreactors. He has been a leader in the Biotechnology Subject Division and an inspiration to students and researchers in biotechnology.

Campbell W. Robinson Professor emeritus, University of Waterloo, Vancouver, BC PhD, University of California, Berkeley, 1971 Member of the CIC since 1971 Nominated by Norman Epstein, HFCIC, University of British Columbia Campbell Robinson has enjoyed a highly productive career for over forty 40 in chemical and biochemical engineering, both in industry and academia, by being outstanding in research, teaching, mentoring, editing, and administrating. A special issue of The Canadian Journal of Chemical Engineering (CJChE), Volume 77, October 1999, was dedicated to him for his exemplary

achievements as a chemical engineer and associate editor of the CJChE from 1980–1984, and as editor from 1990–1996.

Announcement CSC/CIC AGM Date Change CSC/CIC members are advised that the Annual General Meetings (AGM) date has been changed to Monday, May 31, 2004 in London, ON. The AGMs are being held in conjunction with the Canadian Chemistry Conference and Exhibition. A sandwich lunch will be served at both the 12:00–12:30 CSC AGM and the 12:30–13:00 CIC AGM. Please refer to the conference Web site at www.csc2004.ca/home.html for the actual room location.

Kevin James Smith Head of chemical and biological engineering, University of British Columbia, Vancouver, BC PhD, McMaster University, 1983 Member of the CIC since 1988 Nominated by Paul Watkinson, FCIC, University of British Columbia

Annonce Changement de date des assemblées générales annuelles pour l’ICC et la SCC Avis aux membres de l’ICC et de la SCC : la date des assemblées générales annuelles sera le lundi 31 mai 2004 à London (Ontario). Les réunions générales annuelles sont organisées conjointement avec le Congrès et exposition canadiens de chimie. Un déjeuner de sandwiches sera servi à l’assemblée générale de la SCC de 12 h à 12 h 30 et de l’ICC de 12 h 30 à 13 h. Veuillez consulter le site Web du congrès au www.csc2004.ca/home_fr.html pour l’emplacement de la salle.

Kevin Smith has made significant contributions to chemical engineering in Canada through his outstanding research on catalytic processes for heavy oil upgrading and for natural gas conversion, involving hydrocracking, hydrodenitrogenation, and desulphurization. He has served the Catalysis Subject Division with distinction and is an award-winning teacher.

2003 Financial Statements By mid-April 2004, copies of the complete audited financial statements of the CIC, CSC, and CSChE will be available (in both official languages) on our Web site and on request from the executive director. The statements will also be available at the annual general meetings of the Institute and the consituent Societies.

États financiers 2003 Dès la mi-avril 2004, des copies des états financiers vérifiés de l’ICC, de la SCC et de la SCGCh seront disponibles dans les deux langues officielles sur notre site Web et sur demande du directeur exécutif. Les états seront aussi disponibles aux assemblées générales annuelles de l’Institut et de ses sociétés constituantes.

April 2004

Canadian Chemical News 33

CSC Bulletin SCC Section head

CNC/IUPAC Travel Awards Bourses de Voyage du CNC/UICPA he Canadian National Committee for IUPAC (CNC/IUPAC) established a program of Travel Awards for young Canadian scientists in 1982. These awards are financed jointly by the Canadian Society for Chemistry’s Gendron Fund and by CNC/IUPAC’s Company Associates. (Boehringer Ingelheim (Canada) Inc. Mark Frosst Canada Inc.) The purpose of these awards is to help young Canadian scientists and engineers, who should be within 10 years of gaining their PhD, present a paper at an IUPAC-sponsored conference outside Canada and the U.S.A. Deadline for receipt of applications: October 15, 2004. Details of the applications procedures can be found at: www.cnc-iupac.org.

Winners for 2004

and Langmuir-Blodgett methods. Her work is directed towards understanding and manipulating molecular assembly and surface interactions in applications of these films as model biomimetic interfaces and surface nanopatterning materials.

Antonella Badia, MCIC, is an assistant professor of chemistry at the Université de Montréal. She received her PhD from McGill University (1996), where she investigated the structure and dynamics of self-assembled monolayers on gold surfaces under the supervision of R. Bruce Lennox, MCIC. She was an NSERC postdoctoral fellow at the Max-Planck Institute for

Polymer Research (1997) and the McGill Centre for the Physics of Materials (1998). Her current research is focused on atomic force microscopy investigations of the structure, interfacial properties, and phase behaviour of two-dimensional assemblies of organic surfactant molecules that serve as model biomimetic systems or surface nanopatterning materials. Badia is the recipient of a Strategic Faculty Award (2000–2004) from the Fonds de recherche sur la nature et les technologies and a Cottrell Scholar (2002) of the Research Corporation. She will use her CNC-IUPAC Travel Award to attend the Ian Wark Research Institute International Conference and Workshop on Physical Chemistry of Bio-Interfaces in South Australia in May 2004. Badia’s research involves structure/interfacial property investigations of ultrathin organic films formed by self-assembly

34 L’Actualité chimique canadienne

avril 2004

e Comité national canadien de l’Union internationale de chimie pure et appliquée (CNC/UICPA) remet des bourses de voyage aux jeunes scientifiques canadiens depuis 1982. Ces bourses sont subventionées par le Fonds Gendron (administré par la Société canadienne de chimie) et par les compagnies associées au CNC/UICPA. (Boehringer Ingelheim (Canada) Inc. Mark Frosst Canada Inc.) L’objectif de ces bourses est de venir en aide aux jeunes scientifiques et ingénieurs canadiens, qui sont à moins de 10 ans de l’obtention de leur doctorat, afin de leur permettre de présenter leurs travaux lors d’une conférence commanditée par l’UICPA à l’extérieur du Canada et des États-Unis. Date limite pour postuler : le 15 octobre 2004. Renseignments supplementaires : www.cnc-iupac.org.

Louis Barriault, MCIC, was born in 1970, in Armagh, QC. In 1993, he obtained his BSc in chemistry from the Université de Sherbrooke. He pursued his

PhD at the same institution under the guidance of Pierre Deslongchamps, FCIC. After completing his doctorate in 1997, he joined the group of Leo A. Paquette at the OSU as a FCAR postdoctoral fellow where he completed the total synthesis of (-)-polycarvernoside A. In May 1999, he accepted a position as assistant professor at the University of Ottawa where he has been promoted to associate professor (2003). Barriault’s research involves the development of novel strategies using tandem pericyclic reactions to construct complex bio-active natural products. Recently, Barriault received the John Polanyi Award in Chemistry (2000), Ontario Innovation Trust Award (2000), Premier’s Research Excellence Award (2002), Ottawa Life Science Michael Smith Award (2002), and the Boehringer Ingelheim Young Investigator Award (2002).

CSC Bulletin SCC Section head

Barriault’s research involves the development of novel and effective synthetic strategies to construct complex bio-active natural products.

Eric Fillion, MCIC, joined the department of chemistry at the University of Waterloo in August 2000. His research interests centre on the design and development of catalytic carboncarbon bond forming reactions for the enantio- and stereocontrolled synthesis of bioactive carbocycles and heterocycles. Fillion received his BSc from the Université de Sherbrooke. After completing his MSc at the Université de Montréal with Denis Gravel, FCIC, he pursued his doctoral studies at the University of Toronto under the supervision of Mark Lautens, FCIC. From 1998 to 2000, he was an NSERC postdoctoral Fellow at the University of California, Irvine, in the laboratories of Larry Overman. The CNC/IUPAC Travel Award will allow him to attend the 15th International Conference on Organic Synthesis in Nagoya, Japan in August 2004. Fillion’s research interests centre on the design and development of Lewis acid- and transition metal-catalyzed carbon-carbon bond forming reactions.

Deryn Fogg, MCIC, is an associate professor in the department of chemistry at the University of Ottawa. Her research interests lie in transition metal organometallic chemistry and catalysis, with a particular focus on tandem catalysis, on the design of robust, long-lived, and selective catalysts for olefin metathesis, and on the development of MALDI-MS as a tool for structural elucidation of air-sensitive organometallics. Fogg obtained her doctorate from UBC in 1994, working with Brian James, FCIC, on imine hydrogenation, and subsequently held a postdoctoral appointment with Richard Schrock at MIT, where she developed polymer-quantum dot composites for device applications. She joined the faculty at the University of Ottawa as an assistant professor in 1997, and in 2001 received accelerated tenure and promotion to associate professor. Fogg will use her CNC-IUPAC Travel Award to attend the 36th International Conference on Coordination Chemistry, in Merida, Mexico, in July 2004. Fogg’s research in transition metal chemistry and catalysis focuses on tandem catalysis, and the design of robust, long-lived, and selective catalysts for olefin metathesis. Her group is also pioneering the development of MALDI-MS as a tool for structural elucidation of air-sensitive organometallics.

George Shimizu’s, MCIC, research falls under the umbrella of supramolecular inorganic chemistry. The group has synthesized numerous examples of metal-organic frameworks that function as sorbants and ion exchange materials. The group has focused its efforts on the chemistry of the sulfonate group, which offers interesting binding properties with metals both in the primary and the secondary coordination spheres. A highly unique aspect of this research is the ability of the solids to be structurally dynamic, as compared to zeolite-like solids, while still retaining order and function. Targeted applications of the solids vary from highly selective separations agents, porous solids for gas storage, compounds with second order non-linear optical activity, and the formation of highly ordered proton conducting solids. Shimizu, uses inorganic supramolecular chemistry to synthesize new materials. Target compounds have properties ranging from highly selective separations agents, porous solids for gas storage, compounds with second order non-linear optical activity, and the formation of highly ordered proton conducting solids.

Robert Hudson, MCIC, is currently a faculty member in the department of chemistry at the University of Western Ontario. He holds a cross-appointment to the department of biochemistry, Faculty of medicine and dentistry. He arrived at UWO in 1997 by way of the California Institute of Technology where he tenured a NSERC postdoctoral fellowship studying minor groove-binding polyamides with Peter Dervan. Hudson obtained his MSc in the field of inorganic chemistry with Anthony Poë, FCIC, and his PhD studying nucleic acids with Masad Damha, FCIC, both at the University of Toronto. Hudson’s research at UWO is focused on synthetic and bio-organic chemistry of nucleic acids and peptides, with emphasis on the nucleic acid mimic known as PNA or peptide nucleic acid. He will present his group’s work on the synthesis and properties of nucleobase-modified peptide nucleic acids at the 7th International Symposium on Biomolecular Chemistry (ISBOC-7) held at the University of Sheffield, U.K. Hudson’s research at UWO is focused on synthetic and bio-organic chemistry of nucleic acids and peptides, with emphasis on the nucleic acid mimic known as PNA or peptide nucleic acid.

April 2004

Canadian Chemical News 35

CSChE Bulletin SCGCh Section head

Canadian Society for Chemical Engineering Board of Directors Nominations (2004–2005) Présentation des candidats pour le conseil d’administration de la Société canadienne de génie chimique (2004-2005) he Canadian Society for Chemical Engineers (CSChE) Nominating Committee, appointed under the terms of CSChE bylaws Article 8, Section k, has proposed the candidates listed below to serve as CSChE officers for 2004–2005. Andrew Hart, MCIC, CSChE, past-president and chair of the Nominating Committee, is pleased to announce the candidates for the 2004–2005 election of the CSChE. Additional nominations for candidates may be submitted by members to be received at National Office no later than Tuesday, May 18, 2004. Ten or more voting members must support additional nominations in writing. Those elected, whether by ballot or acclamation, will take office immediately following the AGM of the Society in Calgary on October 5, 2004.

Président, 2004-2005

President 2004–2005 Gerry Phillips, MCIC, a native of Saskatoon, SK, received degrees in chemical engineering and chemistry in 1970 and 1971 from the University of Saskatchewan. Following graduation, he worked with DuPont of Canada in North Bay, ON and Sarnia, ON as a project and plant engineer. In 1979, he obtained his MASc in chemical engineering from the University of Waterloo. Phillips joined NOVA Chemicals in 1979 as a process engineer prior to startup of the first ethylene plant. He later worked as an operations supervisor before taking on the role of site safety engineer. This two-year assignment turned into a career when the disaster in Bhopal, India, changed the context of Process Safety Management (PSM). Phillips is presently NOVA Chemicals’ senior loss prevention engineer and has spent the majority of his career developing and advancing the concepts of PSM in North America and Europe. He has served on national and international committees dealing with process safety and risk assessment and assisted in development of several products related to risk assessment and public safety. When the Major Industrial Accidents Council of Canada dissolved, he led the establishment of the CSChE PSM Subject Division. He has presented papers and chaired sessions at conferences and workshops in North America and Europe. Phillips has been an active member of the CSChE since 1967. He served on the executive of the Sarnia Local Section and on the organizing committee for the 1979 Sarnia conference. He was the Industrial Liaison on the CSChE Board from 1999 to 2002, and served as the first chair of the PSM Subject Division. He is the current CSChE vice-president.

36 L’Actualité chimique canadienne

e comité des candidatures de la Société canadienne de génie chimique (SCGCh), nommé aux termes de l’article k de la section 8 des règlements de la SCGCh, propose les candidats suivants aux postes d’administrateurs de la SCGCh pour l’exercice 2004-2005. Andrew Hart, MICC, président sortant de la SCGCh et président du comité des candidatures, est heureux de présenter les candidats aux élections pour l’exercice 2004-2005. Les membres peuvent présenter d’autres candidats au plus tard le mardi 18 mai 2004. Les mises en candidature supplémentaires doivent être appuyées par écrit par au moins dix membres votants. Les personnes élues, au scrutin ou sans concurrent, entreront en fonction immédiatement après l’AGA de la Société qui se tiendra le 5 octobre 2004.

avril 2004

Originaire de Saskatoon, dans la Saskatchewan, Gerry Phillips, MICC, a étudié le génie chimique et la chimie à la University of Saskatchewan. Après l’obtention de ses diplômes, en 1970 et 1971, il a travaillé chez DuPont Canada à North Bay et à Sarnia, dans l’Ontario, en tant qu’ingénieur de projet et d’usine. En 1979, Gerry a obtenu une maîtrise en génie chimique de la University of Waterloo. M. Phillips s’est joint à NOVA Chemicals en 1979 à titre d’ingénieur des procédés, avant le démarrage de la première usine d’éthylène. Il a ensuite assuré les fonctions de chef d’exploitation, puis celles d’ingénieur spécialiste de la sécurité. Ce dernier mandat, qui devait durer deux ans, a pris les allures d’une carrière lorsque le désastre de Bhopal, en Inde, a transformé le contexte de la gestion de la sécurité des procédés (GSP). M. Phillips est actuellement ingénieur principal, prévention des sinistres, chez NOVA Chemicals, après avoir consacré la plus grande partie de sa carrière au développement et à l’avancement des concepts liés à la GSP en Amérique du Nord et en Europe. Il a siégé dans des comités nationaux et internationaux sur la sûreté des procédés et l’évaluation des risques et a contribué à la mise au point de plusieurs produits reliés à l’évaluation des risques et à la sécurité publique. Après la dissolution du Conseil canadien des accidents industriels majeurs, M. Phillips a dirigé l’établissement de la division de la gestion de la sûreté des procédés de la SCGCh. Il a en outre présenté des communications et présidé des sessions lors de congrès et d’ateliers en Amérique du Nord et en Europe. M. Phillips a été un membre actif de la SCGCh depuis 1967. Il a fait partie du bureau de la section locale de Sarnia ainsi que du comité organisateur du congrès de Sarnia en 1979. M. Phillips a siégé au conseil d’administration de la SCGCh à titre de représentant des relations avec les entreprises, de 1999 à 2002, et a été le premier président de la division de la gestion de la sûreté des procédés. En ce moment, il est le vice-président de la SCGCh.

CSChE Bulletin SCGCh Section head

Vice-President 2004–2005

Vice-président, 2004-2005

Paul Stuart, MCIC, is a professor in the department of chemical engineering at École Polytechnique, and the Chairholder of an NSERC Environmental Design Engineering Chair whose theme is Process Integration in the Pulp and Paper Industry. He received his PhD in chemical engineering from McGill University in 1992—he was the last student of the late William Gauvin, a founding member of the CSChE and its president in 1966–1967. Prior to joining École Polytechnique in 2000, Stuart was a process engineer for 12 years serving the pulp and paper industry including as company associate and manager of process engineering at Beak Consultants Limited, as partner and manager of environmental services at Simons Environmental Group, and as director of the Montréal process and environmental engineering group of H.A. Simons Limited. Stuart is active on many committees related to his field of research including currently as a member of the NRCan Advisory Board on Energy Science and Technology (NABEST), vice-chair of the Canadian Design Engineering Network (CDEN), and he is on the NSERC Strategic Grants panel. He is a professional engineer in the Province of Quebec and continues to consult to the pulp and paper industry through his company, Processys Inc. Stuart has been an active member of the CSChE since 1982. He served in various capacities with the Montréal Local Section during the 1980s including a term as chair, technical program co-chair of the Canadian Chemical Engineering Conference held in Montréal in 2000, and more recently was director of conferences on the CSChE Board from 2000–2003. He has co-chaired the Symposium in Process Integration at the CSChE conference for the last four years.

Paul Stuart, MCIC, enseigne au sein du département de génie chimique de l’École polytechnique et est titulaire d’une Chaire CRSNG en génie de conception environnementale dont le thème est l’intégration des procédés pour l’industrie papetière. Il a obtenu son doctorat en génie chimique de l’Université McGill en 1992 – il a d’ailleurs été le dernier étudiant de feu William Gauvin, un membre fondateur de la SCGCh dont il fut président en 1966-1967. Avant de se joindre à l’équipe de l’École polytechnique en 2000, M. Stuart a travaillé comme ingénieur des procédés durant 12 ans au service de l’industrie des pâtes et papiers, notamment à titre d’associé et gestionnaire des procédés opérationnels de Beak Consultants Limited, de partenaire et directeur des services de l’environnement du Simons Environmental Group et en tant que directeur du groupe de génie des procédés et de l’environnement de Montréal de H.A. Simons Limited. M. Stuart est membre actif de plusieurs comités liés à son domaine de recherche. En effet, il est présentement membre du Comité consultatif de RNCan sur les sciences et les technologies énergétiques (CCRSTE), vice-président du Réseau canadien de la conception en ingénierie (RCCI) et membre du comité des subventions stratégiques du CRSNG. Il travaille toujours comme ingénieur professionnel dans la province de Québec et continue d’apporter ses services d’expert-conseil à l’industrie des pâtes et papiers par l’entremise de son entreprise, Processys Inc. M. Stuart est membre de la SCGCh depuis 1982. Il a occupé plusieurs fonctions au sein de la division locale de Montréal durant les années 1980, notamment celles de président, de coprésident du programme technique du Congrès canadien de génie chimique qui a eu lieu à Montréal en 2000 et, plus récemment, de directeur des congrès au sein du conseil d’administration de la SCGCh de 2000 à 2003. Il a également coprésidé le Symposium sur l’Intégration des procédés lors des quatre derniers congrès de la SCGCh.

Statement of Policy The CSChE was created in 1966, and has evolved along with the Canadian chemical engineering community over nearly four decades. We can be proud of its role as a technical association serving the interests of chemical engineers in industry, academia, and government. The Society should continue to build on its existing programs and strengths, and create new initiatives to increase its visibility nationally and internationally in the coming years. I will work hard to focus on this overall vision. First and foremost, the CSChE must have a strong balance sheet in order to achieve its goals. The Society should follow through on the measures that have been outlined and executed over the past few years to ensure a balanced budget. We should focus on our existing program strengths, continuing to increase membership as we have over the last several years. Certain programs should be evaluated, and possibly modified to enhance their impact on our overall financial position. Canada will host the 2009 Chemical Engineering World Congress. As we approach this exciting event, it is appropriate that we distinguish ourselves relative to other chemical engineering societies around the world, including when appropriate, taking a position on important issues where chemical engineering knowledge is pertinent to the debate. We should identify opportunities within existing programs to celebrate our evolution as a Canadian engineering community, our successes in research and innovation, and our traditions as an open and inclusive community. Our annual conference has a unique and informal format. It effectively captures Canadian research activities, and has an increasingly strong international reputation. We can also be proud of The Canadian Journal for Chemical Engineering. We need to examine these two vehicles, and as 2009 approaches, develop initiatives that raise the visibility of Canada’s chemical engineering community and thereby further strengthen our Society. Canadian chemical engineers have a lot to be proud of. The CSChE needs to collaborate with Canadian chemical engineering departments and Canadian industry to prepare for 2009, which should provide a great forum to celebrate successes with our peers from around the world.

Énoncé de politique La Société canadienne de génie chimique (SCGCh) a été créée en 1966. Depuis près de 40 ans, elle évolue de pair avec la communauté canadienne de génie chimique. Nous pouvons être fiers de son rôle en tant qu’association technique représentant les intérêts des ingénieurs chimistes de l’industrie, du monde de l’enseignement et des gouvernements. La Société devrait continuer de miser sur ses programmes actuels et ses forces ainsi qu’amorcer de nouvelles initiatives pour accroître sa visibilité aux niveaux national et international au cours des prochaines années. Je vais déployer des efforts soutenus pour atteindre cet objectif. D’abord et avant tout, la SCGCh doit afficher un solide bilan afin de pouvoir atteindre ses objectifs. Elle devrait donner suite aux mesures définies et mises en oeuvre ces dernières années pour assurer un budget équilibré. Nous devrions nous concentrer sur les points forts de nos programmes et continuer d’accroître le nombre de nos membres comme nous avons réussi à le faire au cours des dernières années. Certains programmes devraient être évalués et éventuellement modifiés pour accroître leur impact sur notre situation financière générale. Le Canada accueillera le Congrès mondial des ingénieurs chimistes en 2009. Au moment où nous approchons de cet événement d’importance, il faut se distinguer des autres sociétés de génie chimique du monde entier, y compris, le cas échéant, se prononcer sur des questions importantes lorsqu’elles font appel à des connaissances en génie chimique pertinentes pour le débat. Nous devrions relever au sein des programmes existants les possibilités de célébrer notre évolution en tant que communauté canadienne de génie, nos réussites dans le domaine de la recherche et des innovations ainsi que nos traditions en tant que communauté ouverte et favorisant l’intégration.a formule de notre congrès annuel est unique et informelle. Elle intègre efficacement les activités canadiennes de recherche et, de plus en plus, elle acquiert une solide réputation au niveau international. Nous pouvons aussi être fiers de la revue The Canadian Journal for Chemical Engineering. Nous devons examiner ces deux moyens de diffusion et, à l’approche de 2009, créer des initiatives qui augmentent la visibilité de la communauté canadienne de génie chimique et, par le fait même, renforcent davantage notre position. Les ingénieurs chimistes canadiens ont beaucoup de raisons d’être fiers. La SCGCh doit collaborer avec les départements de génie chimique et l’industrie canadienne pour se préparer au congrès de 2009, qui devrait assurer une tribune privilégiée pour célébrer nos réussites avec nos pairs du monde entier.

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Canadian Chemical News 37

CSChE Bulletin SCGCh Section head

Secretary/Treasurer 2004–2005

Secrétaire-trésorier, 2004-2005

Souheil Afara, MCIC, is a lab supervisor for the department of chemical and biochemical engineering at the University of Western Ontario in London, ON. He received his BESc degree from the University of Western Ontario in 1982, and remained at Western as a research assistant from 1982–1988. In 1988, Afara worked as research engineer for the Chemical Reactor Engineering Centre (CREC) at Western’s faculty of engineering until 1999. He then returned to Western’s chemical and biochemical engineering department from 1999 to present. Afara has been a member of the CSChE since 1982. He was treasurer of the 48th CSChE conference in 1998, and has served as treasurer of the CSChE Board from 1999 to present. Since 1988, Afara has also been a member of Professional Engineers Ontario and was the recipient of Western’s Outstanding Achievement Staff Award in 2001

Souheil Afara, MICC, est responsable de laboratoire pour le département de génie chimique et biochimique de la University of Western Ontario, à London, en Ontario. Souheil a reçu son baccalauréat en ingénierie à la University of Western Ontario en 1982 et a occupé le poste d’adjoint à la recherche de 1982 à 1988, dans ce même établissement. En 1988, M. Afara a travaillé en tant qu’ingénieur de recherche pour le Chemical Reactor Engineering Centre (CREC) de la faculté de génie de Western jusqu’en 1999. Depuis 1999, il est rattaché au département de génie chimique et biochimique de cette même université. M. Afara est membre de la SCGCh depuis 1982. En 1998, il a assuré les fonctions de trésorier du 48e congrès de la SCGCh et il occupe depuis 1999 le poste de trésorier du conseil d’administration de la SCGCh. M. Afara est en outre membre de l’association Professional Engineers Ontario et a reçu le prix pour contribution exceptionnelle des employés de la University of Western Ontario en 2001.

Director 2004–2007

Administrateur, 2004-2005

Allan Gilbert, MCIC, graduated with a BASc in chemical engineering from the University of Toronto in 1970. Specializing in pulp and paper research, he continued to his MASc and PhD, also at Toronto. In 1978 he accepted a professorial position in the department of chemical engineering at Lakehead University in Thunder Bay. After a leave in 1982–1983 to develop paper machine control code for Great Lakes Forest Products in Dryden, his research interests shifted to sensor development and control of pulp and paper processes. He was a participant in the control group of the NCE Network on Mechanical and Chemi-Mechanical Pulps from 1990–1999. Gilbert has served as chair of the department of chemical engineering at Lakehead since 1996. He is a father of three engineering sons, although one strayed from the fold into mechanical engineering.

Allan Gilbert, MCIC, a obtenu son BScA en génie chimique de la University of Toronto en 1970. C’est dans le cadre de sa maîtrise et de son doctorat, également effectués à Toronto, qu’il s’est spécialisé dans la recherche sur les pâtes et papiers. En 1978, il a accepté un poste de professeur au sein du département de génie chimique à la Lakehead University de Thunder Bay. Après une brève absence en 1982-1983, période au cours de laquelle il se vouait au développement de codes de commande pour les machines à papier de l'entreprise Great Lakes Forest Products à Dryden, ses intérêts de recherches se sont orientés vers le développement de capteurs permettant le contrôle des procédés dans l’industrie des pâtes et papiers. Il a également fait partie du groupe de contrôle du Réseau sur les pâtes mécaniques et chimico-mécaniques du RCE de 1990 à 1999. M. Gilbert occupe le poste de président du département de génie chimique de la Lakehead University depuis 1996. Ses trois fils sont également ingénieurs, bien que l’un d’eux ait bifurqué vers le génie mécanique.

The Ottawa Chemistry Olympiad An on-site competition at the Science and Engineering Olympics The Ottawa CIC Local Section was once again involved in the Science and Engineering Olympics that were held at the Canada Science and Technology Museum on February 24 2004. Students in Grades 7 to 12 from 15 schools were involved in the on-site Chemistry Quiz run by the Ottawa CIC Local Section. Two students from each school answered a series of questions of increasing difficulty, as read by Helen P. Graves Smith, MCIC, and marked by Savita Pall, MCIC. The winners of the contest for Grade 7 and 8 students were determined from the preliminary rounds. T-shirts were awarded to the top team: Cassandra Cao and Véronique Gingras-Gauthier from École secondaire publique De La Salle. The top three teams from the high school contest, for Grade 9 to 12 students, had to work a little harder! After the preliminary rounds they were invited onto the stage to compete head-to-head in front of a full auditorium of students, teachers, and judges. With some encouragement from the crowd, the students answered more challenging questions.

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T-shirts were given to the top three winning teams:

1st place:

Collège catholique Samuel-Genest Eric Pelot and Marlène Mansour

2nd place:

Colonel By Secondary School Hoan Nguyen and George Huang

3rd place:

Merivale High School Sheng Li and Pam Zhang Pall and Graves Smith were on hand to present the T-shirts to the winners of this competition and to present the trophy, which Local Section provided in 2003, to the winning school in the Grade 7 and 8 category for the whole Science and Engineering Olympics. This year that school was École secondaire catholique Béatrice-Desloges. Congratulations to everybody! Helen P. Graves Smith, MCIC

CIC News ICC Section head

Annual General Meeting and Dinner Assemblée générale annuelle et dîner

Hear Ye! Hear Ye!

May 5 mai 2004 18:00–22:00

The Chemical Institute of Canada 2005 Awards

Algonquin College, Woodroffe Campus, Building D Édifice D, Collège Algonquin, campus Woodroffe With a special presentation from / Avec une présentation spéciale de Sgt. Carl McDiarmid, RCMP Forensic Identification Research Services “Chemical Aspects of Forensics” Agenda / Ordre du jour 18:00 Cocktails, cash bar / Apéritifs, bar payant 18:30 Dinner / Dîner 20:00 Local Section business / Affaires de la section locale 20:30 Guest speaker presentation / Présentation du conférencier invité Cost is $20 person, payable at the door. If you plan to attend or have any special dietary needs, please contact Fred Scaffidi at 613-990-2300 or SCAFFIF@tc.gc.ca.ca by April 23, 2004. Please visit our Web site at www.cheminst.ca/sections/ottawa for more details. Le coût est de 20 $ la personne, payable à l’entrée. Si vous désirez être présent ou avez un besoin alimentaire spécifique, veuillez communiquer avec Fred Scaffidi au (613) 990-2300 ou SCAFFIF@tc.gc.ca d’ici le 23 avril 2004. Pour plus de renseignements, visitez notre site Web à www.cheminst.ca/sections/ottawa. Parking is free (Lot 9 or 12) / Le stationnement est gratuit (terrain 9 ou 12).

The Union Carbide Award is presented to a person who has made an outstanding contribution in Canada to education at any level in the field of chemistry or chemical engineering. Award: A framed scroll, a cash prize of $1,000 and travel expenses Deadline: The deadline for this CIC award is July 1, 2004 for the 2005 selection. Please submit your nominations to: Awards Program, The Chemical Institute of Canada, 130 Slater Street, Suite 550, Ottawa, ON K1P 6E2; tel.: 613-232-6252, fax: 613-232-5862; awards@cheminst.ca Nomination forms and the full Terms of Reference for these awards are available at www.cheminst.ca.

Peterborough Local Section Salutes Trent University Chemistry Students The Peterborough CIC Local Section participated in an awards ceremony to recognize chemistry students at Trent University on January 30, 2004. The Section also hosted a brief reception following the ceremony. The 2002-2003 prize recipients were as follows: The Robert Annett Scholarship: Danielle Dusome CRC Handbook Prize: Sandra Rutherford Graham Hartley Prize (1st year): Ina Koseva and Julie Metcalf (this is a Peterborough Section sponsored award) Graham Hartley Prize (2nd year): Sarah Nienhuis (this is a Peterborough Section sponsored award) The David Sutherland Irwin Prize: Ursula Meier The Makhija Prize in Chemistry: Danielle Dusome The Organic Chemistry Prize: Lambert Ampong Professional Engineers Wives’ Prize: Sarah Nienhuis The R&R Laboratory Prize in Analytical Chemistry: Meghan Woods The Society of Chemical Industry Student Merit Awards: • Biochemistry: Kerry Presley • Chemistry: Mark Robinson The Chemistry Undergraduate Society Improvement Award: Pearl Signaporia

April 2004

Canadian Chemical News 39

Division News Nouvelles deshead divisions Section

CCC Conference 2004 College Chemistry Canada’s 31st conference will be hosted by Okanagan University College in Kelowna, BC, June 10–13, 2004. The conference, entitled a “Taste of Chemistry” will look at the wine industry in the Okanagan Valley, which is fast becoming a world-class producer of truly great wines. The conference begins Thursday evening with a wine and cheese reception. On Friday and Saturday they will present speakers knowledgeable in the wine industry, including a presentation about the analysis and characterization of aroma precursor compounds in wine by members of Nigel Egger’s research group at Okanagan University College. The Eggers group carries out collaborative studies with the Pacific Agri-Food Research Centre (PARC). We plan to offer a wine-tasting workshop. The conference will also present topics related to the teaching of chemistry. The CCC Banquet Saturday evening will be held on the patio overlooking Okanagan Lake at Gray Monk Estate Winery. For Sunday, we are planning a day of local fun/activity. You can chose one of two activities: a scenic bicycle ride on the famous Kettle Valley railway through the hills above Okaganan Lake with lunch at Hillside Estate Winery; or a tour of Summerhill Estate Winery and lunch while cruising Okanaga Lake on the Fintry Queen, Kelowna’s historic paddle wheel boat. For more information, contact Pat Baird at pbaird@OUC.bc.ca or telephone 250-762-5445, ext. 2239. Anyone wishing to present a paper can contact Stephen McNeil at smcneil@ouc.bc.ca or telephone 250-762-5445, ext. 7573.

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Student News Nouvelles deshead étudiants Section

Silver Medalists Honoured The CIC is proud to announce the 2002 Silver Medal winners. The medals are awarded on behalf of each Society.

CSC Silver Medal Winners Gagnants de médailles d’argent de la SCC The Canadian Society for Chemistry encourages undergraduate students in chemistry and related subjects by offering an award to the student with the highest marks, entering his or her final year of studies at each chemistry and/or biochemistry department in Canada. The CSC Medal consists of an engraved medal and a certificate of merit. The Society offers its congratulations to those students who received the CSC Medal.

La SCC souligne les efforts des étudiants de premier cycle en chimie ou autres matières connexes en décernant un prix à l’étudiant(e) qui aura obtenu(e) les meilleures résultats scolaires à son avant-dernière année d’études dans un programme conduissant à l’obtention d’un diplôme en chimie ou en biochimie. Le prix de la SCC comprend une médaille gravée, accompagnée d’un certificat de mérite. La Société tient à féliciter les étudiants suivants qui ont mérité cette médaille :

Bishop’s University Trevor Taylor

Ryerson University Paula Brown

University of Calgary Jeffrey Francis Van Humbeck

Brandon University Christa Miriam Homenick

Simon Fraser University Mathieu Bohemier-Bernard

University of Guelph Judith Cirulis

Carleton University Chris Rowley

Sir Wilfred Grenfell College Christina Smeaton

University of Manitoba Meghan Nicole Gallant

Dalhousie University David Herbert

Université de Moncton Stéphane Bourque (Biochimie) Mike Doucette (Chimie)

University of New Brunswick Crystal Craig

Laurentan University Natalie Lefort

Université du Québec à Chimie François Simard

McGill University Suzanne Hulme (Chemistry) Ramzy Wahhab (Biochemistry)

Université Laval Francis Cronier

McMaster University Dana Nyholt (Biochemistry) Cathy Wong (Biologicial Chemistry)

University College of Cape Breton Jason Kenneth Pearson (Chemical Science) Kristin Marie Power (Chemical Science)

Memorial University Timothy Kelly

University College of the Cariboo Stuart D. Chambers

Queen’s University Genevieve Gavigan (Engineering Chemistry) Yoonjung Huh (Chemistry)

University College of the Fraser Valley Lori Thiele University of Alberta Jonathan Ailon University of British Columbia Bryan Ka Ip Chan

University of Regina Steven Hepperle University of Saskatchewan Heather Lynn Filson University of Toronto Eugene Kwan University of Toronto – Mississauga Mohamed Alarakhia University of Toronto – Scarborough Amber Asad University of Windsor Ben Johnson (Biochemistry) Alexis Taylor (Chemistry) York University Boris Zevin

Tom Sutton, FCIC, with the CSC silver medallists from McMaster University: Dana Nyholt (left) and Cathy Wong (right).

April 2004

Canadian Chemical News 41

Student News Nouvelles deshead étudiants Section

CSChE Medal Winners Gagnants de médailles de la SCGCh In addition to the medal and certificate of merit offered by all the societies, the Canadian society for Chemical Engineering awards an additional prize of $50 and a two-year subscription to The Canadian Journal of Chemical Engineering. Winners have achieved top marks in their third year of a chemical engineering program. The Society wishes to congratulate those students who received the CSChE Medal.

La SCGCh décerne comme toutes les autres sociétés des médailles et certificats de mérite. Cependant, elle désire accorder un prix additionel de 50 $ et un abonnement de deux ans au Canadian Journal of Chemical Engineering, aux étudiants qui auront obtenu les meilleurs résultats scolaires à leur avant-dernière année d’études dans un programme approuvé de génie chimique. La Société désire féliciter les étudiants suivants qui ont mérité la Médaille de la SCGCh :

Dalhousie University David Castagné

Ryerson University Melody Johnson

University of New Brunswick Sarah Harvie

McMaster University Sara Yonson

Université de Sherbrooke Nicole Desnoyers

University of Ottawa Jason Gaudette

Queen’s University Jordan Pohn

University of Alberta Patricia Taylor

University of Saskatchewan Danielle Meyer

Royal Military College Chelsea Anne Braybrook

University of Calgary Sarah Harvie

University of Toronto Rafael Mattos Dos Santos

RMC’s Officer Cadet Chelsea Anne Braybrook receives her silver medal for chemical engineering.

Matthew Stevens of the University of Waterloo, department of chemical engineering.

University of Waterloo Matthew Stevens

Professional Directory Répertoire professionnel Section head

Employment Wanted Demandes d’emploi

Chemical Engineer (Bachelors) with six years of experience in Chemical Process Design, Project Coordination and Safety Studies is looking for a similar position in GTA and surrounding area. Has experience in simulation software such as ChemCAD, HTRI and PHAST. Has worked on projects for Pharmaceutical and Chemical Industries. Contact Meghal at 905-874-4090 or meghal@rogers.com. Chemical Group

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C. Lloyd Sarginson B.Sc. (Chem. Eng.), LL.B. Philip C. Mendes da Costa B.Sc. (Chem. Eng.), LL.B. Michael E. Charles B.Eng.Sci. (Chem. Eng.), LL.B. Micheline Gravelle B.Sc., M.Sc. (Immunology) Andrew I. McIntosh B.Sc. (Chem.), J.D., LL.B. Anita Nador B.A. (Molec. Biophys./Biochem.), LL.B. Noel Courage B.Sc. (Biochem.), LL.B. Patricia Power B.Sc., Ph.D. (Chem.) Meredith Brill B.Sc., (Chem. Eng.), LL.B.

Practice Restricted to Intellectual Property Law Scotia Plaza, 40 King Street West, 40th Floor Toronto, Ontario Canada M5H 3Y2 416 364 7311 fax: 416 361 1398

2000 Argentia Road, Plaza 4, Suite 430 Mississauga, Ontario Canada L5N 1W1 905 812 3600 fax: 905 814 0031 www.bereskinparr.com

Student News Nouvelles deshead étudiants Section

CSCT Medal Winners Gagnants de médailles de la SCTC The Canadian Society for Chemical Technology extends congratulations to those students attending a college or a CEGEP, who received the Society’s medal. The students listed have achieved top marks in a CSCT accredited Chemical, Biochemical , or Chemical Engineering Technology program.

British Columbia Institute of Technology Sheri Watson Centennial College Kawsalya Ponnampalam (Biotechnology)

La SCTC tient à féliciter les étudiants suivants qui se sont vu décerner la médaille de la Société. Ces étudiants des Collèges ou des cégeps ont obtenu les meiulleurs résultats scolaires tout au cours de leur programme de technologie chimique, biochimique ou technologie génie chimique, approuvé par la Société.

Durham College John Dwinnell (Chemical Engineering Technology) Shane Wood (Environmental Technology) Humber College Jurgen Kola (Chemical Technician) Nameeta Darshani (Chemical Technology)

Collège Ahuntsic Annie Vachon Aynet Pérez Gomez Dawson College Mathieu Charbonneau Durham College Kim Elder (Food and Drug Technology)

Mohawk College Christine Di Sapio (Chemical Engineering Technology – Environmental) Brandon Djukic (Chemical Engineering Technology)

Northern Alberta Institute. Of Technology Amanda Carlton Sheridan College Kevin Elliott (Chemical Engineering Technology – Environmental) Bindu Gupta (Chemical Engineering Technology) Southern Alberta Institute of Technology Martin Niemiec University College of Cape Breton Blair Jason Mombourquette

New Brunswick Community College Heather Best

www.chemistry.mcmaster.ca

NEW FACILITIES FOR TEACHING AND GRADUATE RESEARCH

Analytical & Environmental Chemistry Biological Chemistry Inorganic Chemistry Materials Chemistry Organic Chemistry Physical & Theoretical Chemistry

April 2004

Canadian Chemical News 43

Meetings/Réunions Section head

Canada

U.S. and Overseas

Seminars and courses

April 25–29, 2004. AIChE Spring National Meeting, New Orleans, LA; Tel.: 212-591-7330; Web site: www.aiche.org.

April 26–28, 2004. 8th Annual Process Control Applications for Industry Workshop (APC 2004), Vancouver, BC. Web site: www.ieee-ias.org/apc2004/index/html. May 20–21, 2004. U.S.–Canada Joint Workshop on Innovative Chemistry in Cleaner Media, Montréal, QC. Tel.: 504-398-8457; E-mail: cj.li@mcgill.ca. October 4–5, 2004. ICPES—Inductively Coupled Plasma Emission Spectroscopy, Canadian Society for Chemical Technology, Calgary, AB. Tel.: 888-542-2242; Web site: www.cheminst.ca/prof/dev. October 4–5, 2004, Laboratory Safety, Canadian Society for Chemical Technology, Calgary, AB. Tel.: 888-542-2242; Web site: www.cheminst.ca/prof/dev. November 5–7, 2004. The 15th Quebec–Ontario Mini-Symposium in Synthesis and Bio-Organic Chemistry (QOMSBOC), Ottawa, ON. Contact: Louis Barriault or William Ogilvie; Tel.: 613-562-5800.

May 11–14, 2004. The Global Analysis Fair – Analytica 2004, Munich-, Germany. Web site: www.canada-unlimited.com. August 22–26, 2004. ACS Fall Meeting (2287th), Philadelphia, PA; Tel.: 800-227-5558; E-mail: natlmtgs@acs.org; Web site: www.acs.org. November 7–12, 2004. AIChE Annual Meeting, Austin, TX; Tel.: 212-591-7330; Web site: www.aiche.org. July 10–15, 2005. 7th World Congress on Chemical Engineering (WCCE7), IchemE and the European Federation, Glasgow, Scotland-. Contact: Sarah Fitzpatrick; E-mail: sarah.fitzpatrick@concorde-uk.com. August 13–21, 2005. IUPAC 43rd General Assembly, Beijing, China. Contact: IUPAC Secretariat; Tel.: +1 919-485-8700; Fax: +1 919-485-8706; E-mail: secretariat@iupac.org.

Conferences April 28–29, 2004. 8th Canadian Pollution Prevention Roundtable (CPPR), Canadian Centre for Pollution Prevention, Ottawa, ON. Contact: Sue McKinlay; Tel.: 519-337-3425; E-mail: sue@c2p2online.com; Web site: www.c2p2online.com. May 16–19, 2004. Biannual Canadian Surface Science Conference: Surface Canada 2004, Vancouver, BC. Web site: www.chem.ubc.ca/surfacecanada. May 16–19, 2004. 18th Canadian Symposium on Catalysis, Montréal. QC. Contact: Jitka Kirchnerova; Tel.: 514-340-4711; E-mail: jitka.kirchnerova@polymtl.ca; Web site: www.polymtl.ca/18CSC2004. May 29–June 2, 2004. Strong Roots/New Branches—87th Canadian- Society for Chemistry Conference and Exhibition, London-, ON. Web site: www.csc2004.ca. June 9–11, 2004. CACD 17th Annual Meeting and NACD Region IV Meeting, Québec, QC. Contact: Cathy Campbell; Tel.: 905-844-9140; Web site: www.cacd.ca. July 10–14, 2004. 15th Canadian Symposium on Theoretical Chemistry (CSTC 2004), Sainte-Adèle, QC. Web site: www.chem.queensu.ca/cstc2004. October 3–6, 2004. Energy for the Future—54th Canadian Chemical Engineering Conference, Calgary, AB, Canadian Society for Chemical Engineering (CSChE); Tel.: 613-232-6252; Web site: www.csche2004.ca.

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Available at no charge: Bound copies of Analytical Chemistry, 1937–1984 E-mail cgilmore@dawsoncollege. qc.ca for further information

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