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

L’Actualité chimique Chemical News Canadian

canadienne

January janvier

2004 Vol. 56, No./no 1

Natural Products Nutraceuticals Biodegradable Polymers Fresh Ideas in Packaging … and so much more!

L’Actualité chimique canadienne

Canadian Chemical News

January janvier

2004 Vol. 56, No./no 1

Table of contents Table des matières

A publication of the CIC Une publication de l’ICC

Page 11

Page 16

• Guest Column/Chroniqueur invité Canadian Research Future Looks Promising Roland Andersson, MCIC

Feature Articles/Articles de fond

• Personals/Personnalités

That’s a Wrap

Page 28

Corn yields a natural solution for sustainable food packaging

• News Briefs/Nouvelles en bref

• Book Review/Critique littéraire

• Chemical Shifts Cathleen Crudden, MCIC

• Chemputing Fit to Print Marvin D. Silbert, FCIC

• Chemfusion The Natural Chemistry of Insects Joe Schwarcz, MCIC

• PAGSE Report/Rapport du PFST

• CIC Bulletin ICC

• Division News/Nouvelles des divisions

• Local Section News/ Nouvelles des sections locales

• Student News/Nouvelle des étudiants

• Careers/Carrières

• Events/Événements

Prepared exclusively for ACCN by Cargill Dow LLC

Au Naturel

Canadian industry looks toward a global opportunity in the functional food and natural health products market. Kelley Fitzpatrick

Seeds of Change The growing trend of producing biodegradable polymers from oilseed crops Suresh S. Narine

Cover/Couverture Nature’s Candy: JoEl Inc. candy company wraps each piece of its new College Farm organic hard candies in clear, corn-based film called NatureWorks PLA. See the story on p. 18. What’s Canada’s role in the promotion of environmentally sustainable, dietetically fortifying, homegrown, and globally marketable natural products?

Guest Column Chroniqueur invité Section head

Canadian Research Future Looks Promising On his first day—Paul Martin makes key changes to advance research and innovation Roland Andersson, MCIC ith the swearing in of Paul Martin as prime minister on December 12, 2003, the future of research and innovation in Canada looks very promising. Consider that Martin was in charge of federal finances and supported major initiatives over the past half-dozen years such as the Canadian Foundation for Innovation (CFI), the development of the Canadian Institutes for Health Research (CIHR), the Canada Graduate Scholarships, the Canada Research Chairs, the introduction of a program to financially support indirect costs of research, and the continued increases beyond inflation rates to both granting councils (Natural Sciences and Engineering (NSERC), Socials Sciences and Humanities Research (SSHRC)). In his first day as prime minister, Martin announced the realignment of the functions of departments and agencies and changes to the Cabinet committee system. Martin has committed to a new focus on science and technology with significant changes in government (such as new Ministers of State include New and Emerging Markets, Infrastructure) and key science advisory positions reporting to the prime minister. The appointment of Arthur Carty, HFCIC, in the newly created position of National Science Advisor to the prime minister is great news. He will work closely with the National Advisory Council on Science and Technology. Joe Fontana has been appointed Parliamentary Secretary to support the prime minister on science and technology. For the full news release please see: “Prime Minister Announces Appointment of Cabinet” at www.gc.ca/eng/news. Many of Martin’s changes reflect recommendations made by the Partnership Group for Science and Engineering

2 L’Actualité chimique canadienne

(PAGSE) over the past several years. PAGSE’s September 25, 2003 recommendations to the House of Commons Standing Committee on Finance (www.page.org/en/discussion_papers/sub 2003e.htm) were the creation of a PMO Office of Science and Innovation, Setting Priorities for Research, Commercialization of Research, International Dimensions, and continued support for the Granting Agencies and Cluster Development. Besides the support of the new Martin government, there are other reasons for the chemical sciences and engineering community to be optimistic for the future. I believe that Canadians have truly turned the corner from the days of branch plant/natural resources dependency mentality to a new state of quiet confidence as a knowledge-based economy. Young Canadians will feel more confident about the chemical sector, which has always been a leader in technology advancement. Canada has lead the G8 countries in economic growth for the past several years. With both the U.S. and world economies now at their strongest position since the September 11th tragedy, this will bode well for Canada. Despite my optimism, continued strong participation by the CIC in both PAGSE and the Canadian Consortium for Research (CCR) is important. We must work as hard in the good times as when the cycle of the economy is at its lowest point. The CIC/Societies board members must remain diligent in listening to members, developing policies and promoting these in briefs and at meetings with federal cabinet ministers, MPs, and senior bureaucrats. I encourage all members to support the CIC government relations work and to share your thoughts and ideas at chair@cheminst.ca. Or send us a letter to the editor at editorial@accn.ca.

Roland Andersson, MCIC, is executive director of The Chemical Institute of Canada and can be reached at randersson@cheminst.ca.

janvier 2004

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

Industry

scientists’ labour have led to the advancement of science in addition to having contributed to the well-being of patients,” said André Marcheterre, president of Merck Frosst.

University

Collins est natif de Val d’Or au Québec. Il a reçu son PhD de l’Université d’Ottawa en 2001 et a, par la suite, effectué un séjour postdoctoral à la University of California at Irvine, sous la direction du professeur Larry Overman. Sa spécialité est la

New York comme chercheur principal. Il se joint à l’Université de Montréal au groupe de recherche sur les nanomatériaux qui occupera un nouveau bâtiment sur le campus à partir de mai prochain. Il s’intéresse en particulier à la compréhension des propriétés électriques de structures de dimensions nanométriques, par ex. les nanotubes de carbone, via la fabrication de systèmes modèles.

Robert N. Young, FCIC

Andreea Schmitzer, MICC Robert J. Zamboni, MCIC

Robert N. Young, FCIC, and Robert J. Zamboni, MCIC, both vice-presidents of medicinal chemistry at the Merck Frosst Centre for Therapeutic Research, have been awarded the Heroes of Chemistry prize by the American Chemical Society (ACS). This year’s prestigious honour recognizes industrial chemists and chemical engineers who are improving children’s health and wellness by creating commercial products based on chemistry. The Merck Frosst scientists are recognized for their contribution to the discovery and development of a medical therapy to help control asthma in adults and children as young as two years old. The award was presented at the 226th national meeting of the ACS. “The drug discovery process is an extremely challenging one where thousands of molecules are tested over years of research. The fruits of the

Christina Smeaton (centre) is the 2003 recipient of the CSC Silver medal for excellence in third-year environmental chemistry at Sir Wilfred Grenfell College. The award was presented by Geoff RaynerCanham, FCIC, (left) on behalf of the CSC and Pierre Rouleau (right), Chair of Environmental Science, on behalf of Grenfell College.

chimie organique et ses travaux de recherche visent le développement de nouvelles stratégies pour la synthèse d’intermédiaires ou de produits chiraux qui sont traditionnellement difficiles à préparer en utilisant les méthodologies courantes.

Richard Martel, MICC

Shawn K. Collins, MICC

L’Université de Montréal est fière d’annoncer la venue au Département de chimie de Shawn K. Collins, MICC.

Richard Martel, MICC, est un diplômé de l’Université Laval sous la direction du professeur Peter H. McBreen. Il a par la suite œuvré au T.J. Watson Research Centre de la société IBM, à Yorktown dans l’état de January 2004

Après des études en Roumanie, son pays d’origine, Andreea Schmitzer, MICC, a obtenu son PhD de l’Université PaulSabatier de Toulouse en France et a effectué des études postdoctorales à l’Université de Montréal sous la direction de la professeure Joelle Pelletier. La spécialité de Schmitzer est la chimie bio-organique et elle s’intéresse, en particulier, à la mise au point de méthodes de conception rationnelle de matériaux possédant des cavités fonctionnalisées adaptées à des besoins spécifiques via les principes de la chimie supramoléculaire et de l’auto-assemblage.

Government The Governor General has presented G. Michael Bancroft, FCIC, with our country’s highest honour for lifetime achievement, The Order of Canada. The Order was established in 1967 to recognize outstanding achieve

Canadian Chemical News 3

Personals Personalités Section head

G. Michael Bancroft, FCIC

ment and service in various fields of human endeavour. Professor at the University of Western Ontario, Bancroft was one of the first chemists to promote the use of synchrotron radiation in research. A billion times brighter than the sun, this light source is used to probe the structure of matter. He was one of the key players in the development of Canada’s first synchrotron that is scheduled to be operational at the University of Saskatchewan in 2004. Thanks to his sustained efforts, this new technology offers the potential for significant breakthroughs in medical science and engineering and increased economic benefits for our country.

Arthur J. Carty, HFCIC

Paul Martin announced the appointment of NRC president Arthur J. Carty, HFCIC, as Canada's first National Science Advisor to the prime minister. Carty will work closely with the National Advisory Council on Science and Technology.

According to Carty, his "years at NRC have been very rewarding and fulfilling,” and they have allowed him “to identify issues at the national level relating to science, technology, and innovation that need to be addressed”. Carty hopes that his “new position will allow (him) to bring these issues directly to the attention of decision makers, and to ensure that the seminal role of R&D is understood and considered in the policy development processes of government.” In that context, his work will continue to involve NRC and he intends to be helpful to NRC as it charts its path in the future. Carty continued, saying that his excitement about the opportunities his new job presents “are coloured by (his) regret at having to leave NRC,” which he described as being the most rewarding years of his career. “I have had the honour to work with some of the brightest minds and the most dedicated people in Canada. Together I believe we have accomplished great things, and I am confident that NRC is well positioned to continue to have a significant impact on Canada and Canadians in the future.” NSERC has announced the winners of the 2003 NSERC Synergy Awards for Innovation. Among the seven partnerships out for national recognition were the CIC’s own: John MacGregor, MCIC, and Theodora Kourti, MCIC, and Tembec Inc. and Dofasco Inc. for statistical methods that recover valuable information from large data flows collected during manufacturing; Douglas Reeve, FCIC, and ERCO Worldwide for a 50-year partnership that has had enormous environmental and economic benefits for the pulp and paper and water treatment industries; Douglas Stephan, FCIC, and NOVA Chemicals Corporation, for new and cost-effective catalysts produce highperformance plastics.

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Distinction Madeleine Jacobs has been named the executive director and CEO of the world’s largest scientific society, the American Chemical Society (ACS). Jacobs was formerly editor-in-chief of the weekly ACS news magazine, Chemical & Engineering News. She heads the 128-year-old Society that has a membership of more than 160,000 chemists and chemical engineers and a staff of 1,900. A chemist and scientific journalist herself, Jacobs is well connected in the scientific and chemical communities at all levels, including the top leadership in industry, academe, and government. In addition to having received dozens of honours and awards in her career as a writer, editor, and innovator, she’s also been recognized for motivating young people with the ACS Award for Encouraging Women into Careers in the Chemical Sciences.

Michelle Piquette

The CIC welcomes the arrival of its new publications manager, Michelle Piquette. Piquette is fluently bilingual and has 20 years’ experience in the publishing industry. She most recently worked for a marketing and communications agency and prior to this in a university public affairs office. Piquette takes on the roles of both publishing editor of The Canadian Journal of Chemical Engineering (CJChE), in collaboration with graphic designer René Lalonde and publications

assistant Jim Bagrowicz, and as editor-in-chief of the Canadian Chemical News/L’Actualité chimique canadienne (ACCN) with managing editor Heather Dana Munroe.

Uttandaraman Sundararaj, MCIC

Uttandaraman Sundararaj, MCIC, is the recipient of the Polymer Processing Society’s prestigious Morand Lambla award, which recognizes originality, high achievement, and potential for continuing creativity among young researchers in the science and technology of polymer processing. He is currently associate professor in the department of chemical and materials engineering at the University of Alberta. He is also the associate Chair of chemical engineering within that department. Sundararaj’s main research interests are in processing of polymer blends and nanocomposites. He is particularly known for his work on blend morphology development during processing and for the effect of reaction and block copolymers on coalescence in polymer blends. He is also recognized for his work in miniature mixing equipment including the design of new processing equipment to melt-blend small amounts of material. His recent research includes visualization and modelling of blend structure generation in twin-screw extruders, and processing and properties of novel polymer nanocomposites.

Personals PersonalitĂŠs Section head

Obituaries Keith J. Laidler, FCIC, FRSC, passed away on August 26, 2003, at the age of 87. Professor emeritus at the University of Ottawa, Laidler taught in the department of chemistry from 1955 to 1981. From 1961 to 1966, he was Chair of the

Laidler was known for his annual Christmas Science Lectures that he started in 1956, only a year after he had joined the university. He was inspired by the Faraday Lectures from the Royal Society that took place once a year in his native England. The Christmas Science Lectures continue to this day, and have grown in popularity. Laidler was also a long-time actor with the Ottawa Little Theatre and a landscape painter. Submitted by the University of Ottawa

Keith J. Laidler, FCIC

department of chemistry and vice-dean of the Faculty of Science. In 1971, he was awarded the University of Ottawa Staff Research Lectureship. He also received The Chemical Institute of Canada Medal. In 1974, he was the recipient of the Chemical Education Award of The Chemical Institute of Canada.

David B. MacLean, FCIC, passed away in August 2003. He graduated from Acadia University with a BSc and received his PhD from McGill in 1945 at the age of 22. He began his career as a research chemist with Dominion Rubber Co. in Guelph, ON, in 1946 and moved on to his academic career at Nova Scotia Tech. in 1949. In 1954, he joined McMaster University and became a full professor in 1960. He later became professor emeritus at the same institution. He served two terms as Chair of the department of chemistry where he was integral in the

installation of the first highresolution mass spectrometer and the first high-pressure liquid chromatographic facility. He tirelessly worked to maintain nuclear magnetic resonance instrumentation that was the envy of Canadian organic chemists. During his lifetime, MacLean submitted over 100 manuscripts for publication journals including the Canadian Journal of Chemistry. Reprinted with permission from the Globe and Mail

Ernest James Wiggins, FCIC, passed away on August 10, 2003 at the age of 85. He received his BSc in chemical engineering from Queenâ&#x20AC;&#x2122;s University in 1938 and his PhD from McGill University in 1946 following active service in the Canadian Army. He became the first head of the Chalk River Atomic Energy Project and was subsequently employed with the Defence Research Board of Canada and with Stanford Research Institute in California. He returned to Canada in 1957 to join the newly activated Saskatchewan Research Council, and in 1962 was appointed director of research of the

January 2004

Alberta Research Council. He held that position until his retirement in 1977. During this period, he led a major expansion in the applied research for Alberta industries such as oil sands and forest products. He was a founder of the Petroleum Recovery Institute and other jointly funded activities with industry that have since helped Alberta become a world leader in oil and gas production technology. He also played a key role in establishing the Association of Provincial Research Organizations to gain greater recognition by the federal government of the importance of the provincial activities in technology and industrial development. Wiggins served as a member of the Alberta Oil Sands Technology and Research Authority and as a consultant on energy-related topics for over 20 years following his formal retirement. He was a lifetime member of the Association of Professional Engineers, Geologists, and Geophysicists of Alberta, and the recipient of an honorary doctorate from Athabasca University. Submitted by Karen Fletcher

Canadian Chemical News 5

News Briefs Nouvelles en bref Section head

Biotech Buddies SemBioSys Genetics Inc., a Canadian biotechnology company, has executed a development agreement with Martek Biosciences Corporation to co-develop value-added specialty oil products with potential pharmaceutical and nutraceutical applications. Under the terms of the multi-year agreement, SemBioSys will use its Safflower biotechnology capabilities to develop plant-based DHA products for Martek. “Martek had the opportunity to work with many other plant biotechnology companies. The fact that they selected SemBioSys as a partner is tremendous validation of our proprietary technology and development capabilities,” said Andrew Baum, president and CEO of SemBioSys. “We are pleased to have been chosen by Martek as a strategic partner and look forward to this exciting collaboration.” SemBioSys has developed a variety of proprietary genetic engineering technologies for recombinant protein production and metabolic engineering of oilseeds including Safflower. These technologies are ideally suited to the production of high-value lipids in oilseeds. The company has a fully integrated capacity to develop such products from gene through to pilot-scale manufacturing in the shortest possible time. Calgary, AB-based SemBioSys Genetics Inc. is a privately held biotechnology company focused on the development of high-value protein and oilbody-based products. These products implement its proprietary oilbody-based technology—the Stratosome™ Biologics System. Spun out of the University of Calgary in

1996, the company's products include: specialty nutritional oils for infant formula that aid in the development of the eyes and central nervous system in newborns; nutritional supplements and food ingredients that may play a beneficial role in promoting mental and cardiovascular health throughout life; and new, powerful fluorescent markers for diagnostics, rapid miniaturized screening, and gene and protein detection. SemBioSys Genetics Inc.

PetroCanada’s Kyoto Compromise Petro-Canada, one of Canada’s largest energy companies and a former Crown corporation, is involved in oil and natural gas production in Canada and internationally. Ron Brenneman, chief executive of Petro-Canada, said he hopes prime minister Paul Martin will slow Canada’s implementation of the Kyoto accord, a multinational agreement for reducing greenhouse gas emissions. Brenneman was encouraged by conversations he’s had with Martin on the matter. “Paul Martin is clearly committed to the environment and to action on climate change. But he also understands how critical it is to foster private-sector innovation here in Canada to address these daunting changes.” The Kyoto accord seeks to reduce emissions of gases that are caused by burning fossil fuels that are thought to cause global warming. The U.S. has refused to sign the accord, but the federal government has said it will support the

6 L’Actualité chimique canadienne

janvier 2004

agreement. Brenneman said the federal government, under Jean Chrétien, had adopted “a prescriptive approach” on Kyoto by forcing companies like Petro-Canada to reduce greenhouse gas emissions within a specific time frame. He believes the government should allow companies more time to come up with creative solutions, adding that oil companies have a record of producing cleaner fuels and being more energy efficient themselves to save costs. He elaborated by saying that he now has to turn down unproven ideas for reducing greenhouse gas emissions in case they won’t pay off in time for the Kyoto deadlines. The Canadian Press

New Rules— FDA Bioterrorism Act As of December 12, 2003, the American Food and Drug Administration (FDA) must receive advance notice of

shipments of food into the U.S. President George W. Bush’s Public Health and Security and Bioterrorism Preparedness and Response Act of 2002, commonly known as the Bioterrorism Act, includes a large number of provisions to help ensure the safety of the U.S. from terrorism. This translates into action for the Secretary of Health and Human Services (HHS). It is their duty to protect the nation’s food supply against the threat of international contamination. People who manufacture, process, pack, transport, distribute, receive, hold or import food will be required to create and maintain records that the FDA deems necessary to identify the immediate previous sources and the immediate subsequent recipients of food. This will allow the FDA to follow up on credible threats of serious adverse health consequences or death to humans or animals by tracing the food back to its source. Farms and restaurants are exempt from the requirement. For further information visit www.fda.gov/oc/bioterrorism/ bioact.html Agriculture and Agri-Food Canada

News Briefs Section head E Nouvelles en bref Section F Section head Sectionhead head

Organic Chemistry Directory On-Line Organicworldwide.net has just launched its new “Directory of Organic Chemistry Research.” This Web site collects all relevant information about organic chemistry research worldwide in order to facilitate collaborations in this field. Visit the site at www.organicworldwide.net/directory. EcoSynth

NSERC Bumps Up Stipends NSERC has increased the value of its stipends to graduate students and postdoctoral fellows. These increases were made possible by the additional funding provided to NSERC in the February 2003 budget and demonstrate the priority the Council places on support of the training of new researchers. • The Industrial Postgraduate Scholarship stipend was increased from $13,800 to $15,000. The required industrial contribution will increase from $5,500 to $6,000 as of May 1, 2004; • The doctoral-level postgraduate scholarship (PGS Doctoral formerly PGS B) was increased by $1,900 to $21,000 per year; • The Postdoctoral Fellowship was increased from $35,000 to $40,000 per year. The Council has also increased the amount that a professor can pay as a salary contribution or stipend to a doctoral student from an NSERC grant. The new maximum is $19,000 per student

per year, a $2,500 raise from the previous level. This amount does not include nondiscretionary benefits. Natural Sciences and Engineering Research Council ofCanada (NSERC)

Better Than Vitamin E Fat goes rancid over time if no antioxidants are added. Our bodies also contain fat molecules, called lipids, which are essential for our cell membranes. Lipids must also be protected from excessive peroxidation. Left unchecked, it can cause atherosclerosis or various autoimmune and neurodegenerative diseases, such as Alzheimer’s disease, to set in. Nature’s most important weapon in defence of lipid peroxidation is the a-tocopherol vitamin E. An international team of researchers has now developed a new class of antioxidants that are up to 100 times more effective than vitamin E.

The trouble with the peroxidation of lipids is that it is a chain reaction. In the first step, an oxygen radical—a molecule with an unpaired electron on an oxygen atom— removes a hydrogen atom from a lipid. This leaves behind a lipid radical, which has an unpaired electron on a carbon atom, which reacts with an oxygen molecule to form a lipid peroxyl radical. This is an oxygen radical that can then attack another lipid in turn— in order to steal a hydrogen atom—resulting in yet another lipid radical. The vicious circle starts all over again and is difficult to stop. This is where antioxidants like a-tocopherol come into the picture; they intercept the lipid peroxyl radicals. Radical scavengers like tocopherol are phenols. They consist of a six-membered aromatic carbon ring with an attached oxygen atom, and this oxygen atom carries a hydrogen atom. This hydrogen atom is stripped away by the peroxyl radical. In contrast to the lipid radicals, the resulting phenolic radical is relatively unreactive, and the chain reaction stops. In order to find an

January 2004

even better radical interceptor, the chemists searched for a phenolic compound, whose OH group gives up its hydrogen atom more easily than vitamin E. However, most of these super radical scavengers are much to readily attacked by oxygen in the air to be useful. Computer simulations enabled the developer Derek A. Pratt, and his co-workers to develop a new class of air-stable phenolic antioxidants. Subsequent experiments have demonstrated that two of these amino pyridinol compounds, as they are called, are particularly effective radical scavengers. They consist of a phenol ring, in which one of the carbon atoms has been replaced with a nitrogen atom. This aromatic ring is fused with another, aliphatic carbon ring, which also contains a nitrogen atom. “These amino pyridinols are, to the best of our knowledge, the fastest peroxyl-radicaltrapping antioxidants ever reported,” says Pratt. Angewandte Chemie International

Canadian Chemical News 7

Book Review Critique SectionlittĂŠraire head

Book Review While the main focus of this textbook is on the chemistry of the Alberta oil sands, bitumens, and heavy oils, it provides an excellent complement to the study of petroleum chemistry in general. This is not merely another book on crude oil chemistry. It is a major source of information on the manner in which modern fractionation and degradation techniques may be combined with the high resolving power of modern instrumentation to monitor the changes occurring at various stages in the processing of crude oils as well as those occurring in organic matter in sedimentary rocks over geologic time. The book is designed to provide the chemical foundation on which to build professional education training courses related to the needs of the Canadian petroleum industry and to supply the chemical background needed by the process engineer to consider in the development of new technology. It will also be of interest to environmental chemists dealing with organic discharges. A long chapter is devoted to the special role played by the asphaltene fraction in governing the physical and chemical properties of Alberta heavy oils and bitumens. The special issues related to oil sand processing arising from the combined trace minerals, dissolved gases, connate water, unrelated organic matter attached to the mineral matter are treated thoroughly. The work described on the determination of the biomarkers, their concentrations and ratios illustrates the power of this information in ranking the oils in order of the degree of the biodegration and to indicate the thermal maturity status of the oil. This information also suggests a hypersaline marine environment and carbonate source rock for the original oil. This will be of interest to the organic geochemist supporting exploration programs.

8 Lâ&#x20AC;&#x2122;ActualitĂŠ chimique canadienne

New information is presented on methods for the removal of the adsorbed resinous material from the asphaltene to produce a better chemically defined core. The chemistry of the core, revealed by thermal degradation, naphthalene anion, and by nickel boride reduction show the role played by the oxygen and sulfur linkages in holding major segments together. The size of these segments places an upper limit on the size of the aromatic The Chemistry of Alberta Oil Sands Bitumens and Heavy Oils clusters within them. by O. P. Strausz, FCIC, and Elizabeth M. Lown The oxidative degra- 695 pages, ISBN 0778530965 dation by ruthenium Published by The Alberta Energy Research Institute, Suite 2540, ions of the asphaltene Monenco Place, 801 6th Avenue SW, Calgary, AB T2P 3W2 core provides insights www.aeri.ab.ca. into the nature of the Price: $200. alkyl bridges linking the aromatic rings and the type of tural information necessary to undersubstitution on the rings. This unveils a stand the source of process difficulties unifying principle that the bulk of the and to provide geological insights. The chemical constituents of petroleum authors have gone to considerable asphaltene consists of normal alkanoic lengths to provide the appropriate chemical background and to interpret the derived hydrocarbons and heterocycles with minor amounts of pigments, results obtained by the chemical methods and instruments used. Copious references terpenoids and other biotic material. The attached biomarkers in the core are supplied with numerous appendices, are less biodegraded than those in the summaries, and an index to aid students. In essence, this book contains the basic associated maltene fraction. This point illustrates the capacity of the core to chemical knowledge of the oil resources to support the future protect the biomarkers from biodegrada- needed tion and the catalytic action of the clays. development of the oil sand and heavy The complexity of the inorganic and or- oil industry in Canada. ganic matter requires the application of many Douglas S. Montgomery, FCIC, different separation techniques. In some Former head of the Fuels Division of CANMET, cases, degradation methods supported by Energy Mines and Resources, Canada modern instrumental analytical equipment are required to gain the chemical struc-

janvier 2004

Chemical Shifts

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

What the Heck is Wrong with that Reaction?

X–

2 R

SnBu3

PhPdXLn

SnBu3 PdXLn

Ph 1 – XSnBu3

PdLn Ph 3

Scheme 1

find evidence for the Pd alkylidene, which had never been observed. The results of this study, co-authored by crystallographer Nicholas Taylor, appeared in the Journal of the American Chemical Society (2003, 125, 12700).

R Bu3Sn

SnBu3 PdHLn+

oupling reactions such as the Heck reaction and Stille reaction are often used for the construction of carbon-carbon bonds using catalytic amounts of palladium. In the Stille reaction, a stannylated alkene and an electrophile, such as an aromatic halide or triflate are reacted in the presence of a palladium catalyst. Loss of R3SnX drives the reaction. In some cases, particularly those in which the stannyl alkene has another substitutent on the carbon undergoing the reaction, a side product contaminates the reaction. This product is called the “cine” product and results from substitution on the carbon atom adjacent to the stannylated carbon (Equation 1). Since this product is difficult to separate from the desired product, studies directed towards the elimination of this compound would increase the utility of the Stille reaction for more highly substituted vinylstannanes.

Cathleen Crudden, MCIC

The ability to convert olefins into cyclopropanes is a typical reaction of metal alkylidenes. The Fillion group observed ethylene and formaldehyde as products of dimerization and oxidation of the metal alkylidene in the absence of norbornene, thus providing extremely strong evidence for the intermediacy of alkylidenes such as 6 or 3 in the Stille reaction.

Pd catalyst +

Pd(0)

N Sn

R "normal" Stille product Equation 1

Various mechanisms have been postulated to explain the production of the cine product. The key question relates to the reactivity of intermediate 1 (Scheme 1). This complex could react by beta-hydride elimination to yield 2, or by loss of XSnBu 3 to yield Pd alkylidene 3. Both products could ultimately yield the cine product. Eric Fillion, MCIC, and his group at the University of Waterloo set out to

"cine" product

In order to prove that compounds such as 1 can undergo XSnBu3 elimination and generate palladium alkylidenes, the Fillion group reacted stannatrane 4 with Pd(0). This unusual stannane was chosen because it undergoes facile oxidative addition with Pd, which is needed to generate the key beta stannyl species 5 (Scheme 2). In the presence of Pd(0), stannatrane 4 is converted into the iodo species 7 with concomitant transfer of the methylene group to norbornene 8.

8 H2C PdLn

N Sn PdLn 5

+ N Sn

I 7

Scheme 2

January 2004

Canadian Chemical News 9

Chemical Shifts Section head

Additions and Allylations at the University of Alberta Thankfully for chemists at the University of Alberta, mosquito season is over. Compound 9 (below), also known as (5R,6S)-6-acetoxy-5-hexadecanolide is the oviposition attractant pheromone of the female Culex mosquito, which is one of the species that transmits West Nile virus. Oviposition pheromones are released by female mosquitoes in order to attract other females to what is a prime spot for laying their eggs. Thus these types of pheromones could be used to trap female mosquitoes before they reproduce. Compound 9 has recently been synthesized by Dennis Hall, FCIC, and graduate student Xuri Gao, ACIC. Their synthesis, which appeared in the Journal of the American Chemical Society (2003, 125, 9308), employs a tandem Diels-Alder/allylboration strategy which installs both stereocentres and the heterocyclic ring rapidly and with high levels of enantiomeric control.

The synthesis begins with a Diels-Alder reaction between heterodiene 10 and vinyl ether 3 as the dienophile (Equation 2). This particular type of Diels-Alder reaction is called an inverse-electron demand Diels-Alder because the diene is electron poor and the dienophile is electron rich. This is the reverse of “normal” Diels-Alder reactions. The key to the efficiency of Hall’s synthesis is the boronate (B(OR) 2) substituent, which remains in the product (12) as an allyl boronate, which can react with an aldehyde as shown in Equation 3. The reactions of allylic boronates such as 12 with aldehydes proceed in a stereocontrolled fashion to set two new stereocentres remote from the initial one, with high levels of selectivity. Coordination of the aldehyde (R’CHO) to the boron atom in 12 results in a very ordered transition state called the Zimmerman-

C10H21

H OAc (9) Mosquito pheromone

O (10)

O O (12)

(11)

allylboration

Finally, the synthesis of mosquito pheromone 9 was accomplished starting with compound 5, in which R = Et and R’= C 10H 21. Hydrogenation in the presence of palladium on carbon catalyst removes the endocyclic olefin, and the stereochemistry at the alcohol was inverted by converting it into the mesylate, which was then displaced with cesium acetate. Finallly, oxidation with mCPBA/BF 3•OEt 2 yields the desired lactone as shown in Scheme 3.

O OR H OH (13)

Equation 3

mCPBA

1. H2, Pd/C R'

H OH 13

OEt 2. MsCl, NEt3, 18-C-6 3. CsOAc, 18-C-6 toluene, 100 °C

R' H OAc

R' = C10H21

Scheme 3

10 L’Actualité chimique canadienne

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OEt BF3•OEt2 NEt3

Jacobsen's Catalyst (14)

Equation 2

(12) + R'CHO

O Cr

Diels Alder Reaction

CH3

B(OR)2

Traxler structure, which is responsible for the high levels of stereocontrol. Interestingly, heterodiene 10 used in the synthesis of 12 is also an aldehyde, yet the allylborane product did not react a second time with 10. In order to make only one enantiomer of the final product, Hall and Gao employed chromium complex 14, a catalyst developed by Eric Jacobsen at Harvard University. Under optimized reaction conditions, the reaction proceeded with greater than 95 percent enantioselectivity using only 0.3 percent of 14. The second step (Equation 3) could then be carried out without purification leading to a single diastereomer.

Chemical Shifts

Peptides Used to Probe Sweet Spots on Antibodies Carbohydrates are found on the surfaces of all mammalian cells and control many of the biochemical processes carried out by the cell. Their role as cellular sensors is generally initiated by interaction of the carbohydrate with a protein outside the cell. This binding interaction acts as a light switch inside the cell and turns on various processes including immune defence, cell adhesion, fertilization, and metastasis. Within the cell, carbohydrates also play important roles in protein folding and transport. Oligosaccharides are also present on cancerous cells in a unique fashion, making them important targets in cancer treatment. Carbohydrates are also present on the surfaces of bacterial and viral cells. Thus, development of vaccines based on specific carbohydrates is an active area of research. However, the ubiquity of carbohydrates can make this a difficult task. Vaccines must be targeted to specific pathogens and cannot interfere with native carbohydrates that are so important for mammalian biochemistry. For this reason, carbohydrate mimics are being explored as agents to elicit more discriminating immune responses. Remarkably, peptides are proving to be effective carbohydrate mimetics despite the significant differences in their structure. This brings up the question of the nature of the mimicry: is it structural, functional, or completely different? These are some of the questions that Mario Pinto, David Bundle, FCIC, and their collaborators are attempting to answer. In a recent publication in the Proceedings of the National Academy of Science 2003, 100, 15023. the interaction of an octapeptide with the Fab fragment of the antibody SYA/J6, which is specific for the cell surface O-antigen polysaccharide of the pathogen Shigella flexneri Y, was determined by X-ray crystallography and solution calorimetry. Mario Pinto, from Simon Fraser University, David Bundle and Mary Chervenak from the University of Alberta, and Nand Vyas, Meenakshi Vyas and Florante Quiocho from Baylor College of Medicine in Houston, TX, have shown that the binding modes of the pentasaccharide that elicits the immune response in the first place are significantly

different from the synthetic octapeptide. The octapeptide (Met-Asp-Trp-Asn-Met-HisAla-Ala, Figure 1a) has a significantly larger number of contact points with the antibody (126), compared with only 74 in the case of the oligosaccharide. “(Figure 1b), but the peptide does not sit deeply in the pocket and thus its ability to mimic the oligosaccharide it compromised.” Despite the larger

number of contacts, the peptide only binds twice as strongly as the oligosaccharide. Part of the reason for this is the unfavourable entropy of binding of the peptide, which must adopt a significantly more ordered structure once bound in the active site. The incorporation of a large number of water molecules along with the binding is also entropically unfavourable.

Figure 1

Figure 2

Crystal structures of the Fab fragment of the SYA/J6 antibody with bound octapeptide and oligosaccharide. (a) The backbone trace with the bound octapeptide (VL and VH = light and heavy variable domains). For the peptide, carbon is shown in green, nitrogen in blue, oxygen in red, and sulfur in yellow. (b) The same structure with the electrostatic surface potential colour coded: –10 kT is shown in red; neutral in white; and +10 kT in blue. The binding of the peptide (c) is compared with the saccharide (d). The atom types for the sugar are: C, yellow; N, blue; O, red; and for the peptide, C is green, N blue, and O red. The three water molecules are shown as red spheres (c).

The crystal structure of the Fab fragment and the octapeptide is shown in Figure 2. This structure is refined to a resolution of 1.8 Å. The octapeptide fits into the combining site with the first four amino acids in an extended conformation and the last four as an alpha-helix. Direct hydrogen bonds are observed between the amino acids of the octapeptide, between the octapeptide and the Fab fragment, and certain interactions are also mediated by co-crystallized water. There are also a large number of van der Waals interactions. Unlike the oligosaccharide, the peptide does not bind deeply within a pocket in the groove-shaped binding site, and the excess space between the peptide and the bottom of the pocket is filled with three water molecules (compare Figures 2c and 2d). There are overall 14 water molecules associated with peptide binding and only two involved with carbohydrate binding in the respective crystal structures. Cathleen Crudden, MCIC, is an associate professor at Queen’s University in Kingston, ON

January 2004

Canadian Chemical News 11

Chemputing Section head

Don’t be duped! Your empty ink cartridges might still be …

Fit to Print

Marvin D. Silbert, FCIC

nk jet printers have revolutionized the way we use computers. We can produce a high-quality document with a machine that costs almost nothing. Unfortunately, we get hooked and it’s hard to believe, but a replacement set of colour and black ink cartridges can often cost more than the printer. Sure they have a built-in printed circuit board and ultraprecise printing nozzles, but how can it cost more than a few bucks to produce one. I learned many years ago when I bought my first HP DeskJet printer that all it took to re-ink those cartridges was a hypodermic syringe with a long needle and a bottle of Sheaffer Jet Black ink. Just put 10–15 mL in the syringe; stick the needle through the vent hole and push the plunger. Reinstall the cartridge and it’s back in business. If it’s in reasonable shape it might take half a dozen refills. Obviously, HP didn’t like this and they fought back with a new high-capacity cartridge. You filled these at your own peril as pushing the needle through the vent hole punctured a bladder and ink went everywhere. Not to be outdone, the next series of refilling kits included a rubber plug and told you where to drill a hole. Since then refilling kits have taken off with new ones appearing almost as fast as the printer and manufacturers could come out with new cartridge designs. Some are very good; others are not. I have had varying degrees of success. I always succeeded with black, but experienced several disasters with colour cartridges. If you plan to do any photo-quality colour printing you really want to be able to refill those colour cartridges as that photo mode sprays ink so fast you can almost see the level dropping in front of you. This time I decided to go for a quality kit from a reputable manufacturer. I chose Island Ink-Jet in British Columbia (www.islandinkjet.com), a Canadian company with kiosks across the country, including one in a neighbourhood plaza. My printer is a Lexmark Z35 that uses a 10N0016 black cartridge and a 10N0026 colour cartridge. I had recently purchased a Z33 on special for $39.95 just for the

12 L’Actualité chimique canadienne

cartridges and gave the printer away. That gave me a spare pair to fall back on if I went wrong. I started by re-inking the pair myself. My kits had enough ink for three refills and hypodermic syringes for each colour. The black kit also included a drill to expand the vent hole to accommodate the hypodermic needle. I started with the black cartridge and added 10 mL of black ink; wiped it clean with a damp paper towel and in a couple minutes it was reinstalled. It kept going for a few months until it needed another refill. It’s had five now and is working so well I bought a bigger bottle of ink. The colour is much more difficult as the top must come off. I used a box cutter. Be very careful as you can do some serious damage to yourself if that cutter slips. When you get it off,

… it’s hard to believe, but a replacement set of colour and black ink cartridges can often cost more than the printer there are six holes and the diagram shows which colour goes into which. I put 4 mL into each and reattached the top with some electrical tape. I got three more lives from it. When I installed the replacement, I decided I would take it to the kiosk for refilling just to see how the pros do it. The gentleman on duty was kind enough to let me watch and explain what he was doing. He sure got that top off a lot faster than I did. His filling method was essentially the same as mine. Instead of a bit of tape to hold the cover, he used a glue gun. It was a lot neater and the entire job took less than five minutes. Whether they did it or I did it, the print quality was as good as the original.

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The Island Ink-Jet kiosk was located between Canadian Tire and Grand & Toy. That day, Canadian Tire had a special on Lexmark Z35LE (watch the “LE” as it comes with the smaller cartridges) printers for $49.99 and Grand & Toy was selling Lexmark colour cartridges for $49.99. My refill cost $18.95, about 40 percent of the cost for a new cartridge. A DIY refill kit, capable of doing eight refills, is $39.95. That’s $5.00 a refill or 10 percent of the cost of a new one. You win either way. It costs more for the service and some of you may prefer to go that way. I’ll continue doing them myself and ending up with magenta, cyan and yellow stains all over my fingers. I’m a chemist. I know it comes off with a bit of hypochlorite. A few words of caution: Stop using the printer at the first sign of a cartridge going dry. Once they do, they’re garbage. If you plan to refill it yourself, don’t wait too long. If you are going to the kiosk, store it in a small sealed bag with a bit of moist paper towel. They’ll give you one, if you drop by. Try to print something every day. If you can’t, run the maintenance program occasionally to prevent the printhead from drying out. If the printhead looks all caked up with ink, wipe it carefully with a moist paper towel. If the jets are clogged, you can sometimes unclog them by soaking the printhead (not the whole cartridge) in water, or even better, the pros use 50:50 water and Windex. Don’t experiment with inks. Those 2400 dpi jets plug very easily. With a little care, you should be able to cut your ink costs by a factor of three or more. What about the warranty? Forget it. You’ve saved more than enough to toss it out and by a new one. 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.

Chemfusion

The Natural Chemistry of Insects Joe Schwarcz, MCIC love chemists. And right now I’m going to eat one. He’s fully cooked, but I expect would taste pretty bland without the added natural and artificial flavours. For my dining pleasure, he has been encased in hardened maltitol syrup and coloured with yellow #5 and blue #1. Rigor mortis has now set in, but in his heyday this guy was pretty adept at carrying out some amazing chemical reactions. Like converting plant extracts into aphrodisiacs. And no, if you’re wondering, I haven’t taken leave of my senses. Actually, I’m using them. I’m sucking on some “worm candy,” which looks like a regular lollipop except for the clearly visible “worm,” smack in the middle. In reality, it is about an inch-long insect larva that the candy-maker, exercising some literary license for shock value, has called a worm. And why am I doing this? Because it allows me to call attention to the remarkable chemistry of insects. Let’s start with the salt marsh moth. This is not the insect that dines on the woolies in your closet. The larvae of this moth prefer plants, especially those that contain naturally occurring pyrrolizidine alkaloids. Plants, of course, are veritable chemical factories and convert carbon dioxide, water, and nutrients from the soil into thousands of compounds. All the proteins, fats, carbohydrates, and vitamins we need to sustain life originate in plants, which we either eat directly or through animal intermediaries. Plants, however, are not always keen to sacrifice themselves as food for others and have evolved various protective mechanisms. Insects are among the most notorious plant predators and therefore it comes as no surprise that many plants produce a variety of natural insecticides. Have you ever wondered, for example, why tobacco plants produce nicotine, or why the coca plant synthesizes cocaine? Both chemicals deter insects. Nicotine is actually used as a commercial insecticide and researchers have shown that cocaine may be even more effective. They sprayed cocaine solution on the leaves of tomato plants and then put moth caterpillars on the leaves. The insects reared up, began to shake and turned away from the cocaine, apparently showing greater intelligence than some humans.

Pyrrolizidine alkaloids are a class of natural toxins that plants use to wage chemical warfare against insects. With a few exceptions, they are not found in plants normally consumed by humans—which is wise, since a sufficient dose of these

The development of resistance to toxins is quite common in the insect world … compounds are toxic to the liver. Comfrey is one of the plants that contains pyrrolizidines, and curiously, is sometimes recommended by herbalists in the form of a tea for improved health. Admittedly, it takes large amounts of comfrey to cause liver toxicity, but it has happened. So how is it then that the caterpillar of the salt marsh moth frolics on the leaves of pyrrolizidine alkaloid producing plants and even makes a meal of them? The development of resistance to toxins is quite common in the insect world, as farmers who routinely face this problem with commercial insecticides well know. It seems that salt marsh moths have not only developed a resistance to pyrrolizidine alkaloids, but have turned them to an evolutionary advantage. They convert the toxins to a compound called hydroxydanaidal, which has some truly fascinating effects and may well deserve to be called a “moth aphrodisiac.” The male salt marsh moth has little inflatable organs on its belly, called “coremata.” These tube-like appendages are covered with scent scales that project out like tiny hairs. Their purpose is to provide a large surface area through which the scent of hydroxydanaidal can be wafted into the air. When the female senses this chemical, she comes running, and mating ensues. The more effective this chemical release, the greater the chance that the suitor will attract a mate. And amazingly, the male can increase his chances of romance just by

eating right. When scientists put salt marsh moth larvae on diets with different amounts of pyrrolizidine alkaloids (believe it or not “salt marsh caterpillar diet” is commercially available from Bioserv, Inc. of Frenchtown, NJ) they were able to show that adult males fed the largest amounts of the hydroxydanaidal precursors developed the largest coremata. When fully erect, the coremata of the high-dose males reached an impressive two centimetres, whereas the pyrrolizidinedeprived moths barely managed to muster up half a centimetre. Just wait till those spam e-mailers get hold of this information! Not satisfied with the size of your coremata? We’ve got the answer! Pyrrolizidine alkaloids. All natural. Clinically proven! Now let’s turn to the scarlet-bodied wasp moth. He doesn’t use alkaloids to attract the female, but he does offer up a nuptial present of these chemicals that may save her life! Dog fennel is a plant eschewed by herbivores because of its pyrollizidine content. It makes it very bitter. But the scarlet-bodied wasp moth just loves it. He ingests the plant’s juices and stores some in tiny pouches under his abdomen. When the moth engages in amorous activities with the female, he transfers some of the juice to her, making her instantly taste awful to predators. When researchers mated virgin females with males that were bred on the alkaloids and with ones that were not, and then left the unfortunate moths at the mercy of a notorious moth predator, the golden silk spider, they found that the unprotected insects were quickly eaten. The noxious males and their chemically protected concubines escaped. Frankly, I don’t know what sort of caterpillar is in my lollipop. It is just identified as “insect larva.” You see what happens when you have poor labelling laws? But I’ve now consumed most of the candy and I’m almost down to the “worm.” OK. Here we go. Crunch! Not bitter at all. Not a hint of any pyrrolizidine alkaloids. Kind of tasty, actually. Best little chemist I’ve ever eaten. High in protein. Low in fat. You should try one. Joe Schwarcz, MCIC, is the director of McGill University’s Office for Science and Society. You can contact him at joe.schwarcz@mcgill.ca.

January 2004

Canadian Chemical News 13

PAGSE Report Rapport PFST Sectiondu head

CIC Recommendations to the Federal Government PAGSE prepares for the new Martin government by submitting its annual Brief to the House of Commons Standing Committee on Finance Foreword by Roland Andersson, MCIC Foreword hrough its active participation in both the Partnership Group for Science and Engineering (PAGSE) and the Canadian Consortium for Research (CCR), the CIC/Constituent Societies communicate key messages to the federal and provincial governments. The CIC/Constituent Society Boards and the CIC National Office are continuously involved in the development and delivery of key chemical science and engineering field

Research and innovation are of genuine value in enhancing our knowledge-based economy and in assuring Canada’s future competitiveness. related messages to federal MPs, senior government bureaucrats, and other relevant organizations on behalf of its membership. The PAGSE Brief below was delivered on September 25, 2003.

Introduction The Partnership Group for Science and Engineering (PAGSE) is a cooperative association of more than 20 national 14 L’Actualité chimique canadienne

organizations in Science and Engineering, formed in June 1995, at the invitation of the Academy of Science of the Royal Society of Canada. The national organizations that comprise PAGSE include thousands of individuals from industry, academia, and government sectors. PAGSE works together, and in partnership with, government to advance research and innovation for the benefit of Canadians. Organizations of PAGSE provide core support for its meetings and activities. These include defining the economic benefits of research in Canada and the effects of research budgets, analyzing intellectual property issues and other potential impediments to improving academic-industry symbiosis, showcasing the international dimensions of research projects and associations, and informing decision makers about science and engineering and their importance to Canada. PAGSE represents an extensive resource that, through contracts and agreements, can hold events and undertake studies and assessments of benefit to government departments and agencies, to nongovernment organizations, and to the general public. The Royal Society of Canada acts as the agent for PAGSE for any contracts or agreements involving PAGSE projects. PAGSE has the Committee to Advance Research, a university-industry committee, which addresses issues of considerable importance such as the study on “Setting Priorities for Research in Canada.” In addition, in partnership with NSERC, a monthly breakfast meeting is held on Parliament Hill known as “Bacon and Eggheads,” to inform parliamentarians about recent advances in science and engineering. There are also presentations co-hosted by Industry Canada and PAGSE, on trends in science and technology policy, by key decision makers from different countries. Each fall an event is organized on science and engineering issues—for 2003 it will spotlight our “Leaders of Tomorrow.”

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General Comments Research and innovation are of genuine value in enhancing our knowledge-based economy and in assuring Canada’s future competitiveness. Research is a continuum from basic to applied, with developmental work raising new issues, which need to be addressed by creative, basic research. The outcomes of these investigations stimulate economic development and health care, thus raising the quality of life for Canadians. PAGSE applauds the portfolio of Government of Canada programs established in the past six years including, amongst them, the Canada Foundation for Innovation, Canada Research Chairs, Genome Canada, Sustainable Development Technology Fund, Canada Graduate Scholarships, and the significant contributions to the coverage of Indirect Costs. We also appreciate the increased funding that was provided to the Granting Agencies.

Issues and Recommendations PAGSE considers the following to be important issues meriting consideration by the Government of Canada.

1. PMO Office of Science and Innovation Within the Prime Minister’s or President’s Offices of G8 (e.g. U.S., U.K., Japan) and other countries (e.g. Australia) is an office of Science and Innovation (or Technology). Such offices provide a coordinated and cohesive approach to issues relevant to research and innovation. The staff interact on an ongoing basis with Parliament, Diet, or Congress (such as in Canada, this would include the House of Commons Standing Committee on Industry, Science, and Technology). The office also takes responsibility for the coordination of “Big Science” projects, amongst other matters. Addressing this gap in governance in Canada would make a major impact on our society, and on increasing our global competitiveness.

PAGSE Report Rapport PFST Sectiondu head

2. Setting Priorities for Research Having created an impressive number of new tools (such as Canada Foundation for Innovation (CFI), Canada Research Chairs (CRC), Indirect Costs, Genome Canada, Canadian Foundation for Climate and Atmospheric Sciences, Canada Graduate Scholarships, and the Sustainable Development Technology Fund), and supported initiatives established by others (such as MaRS - Medicine and Related Sciences) in the past six years, it is now appropriate to

Given the foregoing, it is an ideal time in Canadian history, to determine what the priorities are for research in Canada for the next five to seven years. “take stock” and consider how these new instruments fit with existing programs (such as Granting Agencies, NCEs, NRC) in addressing research and innovation in Canada. In like manner, these organizations, in collaboration with government departments, have launched highly promising new initiatives that require full harmonization with existing support structures. Given the foregoing, it is an ideal time in Canadian history, to determine what the priorities are for research in Canada for the next five to seven years. Such an exercise would be of enormous value to our society. It would demonstrate a reinvigorated, coordinated, and cohesive approach across all sectors (academia, government, industry) of the research and innovation portfolio. To accomplish these tasks, it is recommended that Government create two panels, one to examine the relationship between the new tools summarized above and longer standing programs for

research and innovation support, and a second to deal with priorities. Regarding the latter, the panel should be provided with, amongst other material, the PAGSE study on “Setting Priorities for Research in Canada.” These panels could report to the proposed new PMO Office of Science and Innovation.

3. Commercialization of Research Technology transfer and business enterprise are now important elements of the outcomes of university-based research. Universities need to markedly build capacity for the commercialization of university research, including the training and employment of individuals with skill sets in intellectual property, contracts management, patents and licensing, venture capital negotiation and management. Likewise, the business sector urgently requires new instruments to assure greater success in transforming new inventions and discoveries into products and processes of substantial commercial value. Start-ups, and SMEs, need a markedly increased supply of venture capital. PAGSE recommends that the Canadian government allocate new resources to the different elements of the commercialization of university research (e.g. venture capital, early procurement of innovative products). Support could involve the creation of a Commercialization Office/Secretariat either reporting to Industry Canada, or created as a nongovernment organization. Such an entity would be responsible for working with universities, companies, and government on different elements in the commercialization process. In addition PAGSE highly recommends the creation of a Canadian analog of the U.S. policy directed to minimizing barriers to industry university partnerships. To accelerate the commercialization of research PAGSE also recommends that: • Government support research and innovation by graduate students and postdoctoral fellows working in SMEs. These researchers must be paid regular employee wages (not co-op or postdoctoral level stipends); • NRC’s Industrial Research Assistance Program (IRAP) provide support for personnel to SMEs; • Government increase the eligibility of the SR & ED Tax Credit Program to include funding to companies that have not attained profitability, in addition to those that are profitable.

4. International Dimension Research is global, and Canadians can profit significantly by collaborating with researchers in other countries. Canada contributes approximately 4 percent to the total global research capacity and thus, by engaging in collaborations, alliances, etc., with those elsewhere, researchers can build upon their own programs for maximum benefit to Canadians. Furthermore, access to facilities not available in Canada can lead to rapid accomplishments in research and innovation. PAGSE recommends that the Government of Canada create an International Innovation Fund (IIF) of thirty million dollars per year to support research partnerships, involving researchers in academia, industry, or government, in areas of priority to Canada. PAGSE recommends that the Royal Society of Canada (in collaboration with the Canadian Academy of Engineering and the Canadian Institute of Academic Medicine) administer the IIF program, an arrangement similar to that in the U.K. where the Royal Society has been, for many years, responsible for a considerable proportion of government supported international research programs.

5. Granting Agencies and Cluster Development The three Granting Agencies (NSERC, CIHR, SSHRC) have been the recipients of new investments by the Government of Canada in the last several years. PAGSE congratulates the Government on these investments. Major challenges exist for the three agencies. These include: a) The enormous pressure created by the unexpectedly large numbers of new applicants; and b) The requirement for appreciably higher levels of support, in order that our current trailblazers, and our “leaders of tomorrow,” can compete effectively on a global basis. The agencies, we believe, should have a valuable role, with industry in the lead (such as Chairs of committees) and NRC as a partner, in building new clusters to serve as springboards for economic development.

PAGSE recommends: • Government create a new industrydriven Triagency Cluster Development program; • In addition, that Government increase overall support to the three agencies, taking account of the genuine needs of each agency.

January 2004

Canadian Chemical News 15

Feature Article Article de fond

That’s a Wrap! Corn yields a natural solution for sustainable food packaging Prepared exclusively for ACCN by Cargill Dow LLC y combining the best of large-scale industrial biotechnology with chemical processing, Cargill Dow LLC is providing food companies the opportunity to offer the complete package with its 100 percent corn-based food packaging material. This new material is known as NatureWorks™ PLA. The technology used to create it allows abundant, annually renewable resources such as ordinary field corn to replace finite ones, such as petroleum. The technology is being used in food packaging, fibres, and many other applications.

Natural packaging gives food fresh appeal NatureWorks PLA is changing the way shoppers think about food packaging by offering all the convenience of traditional plastic packaging while helping reduce environmental impact. “NatureWorks PLA packaging looks, acts, and feels like the packaging we are accustomed to buying, but with the important difference of sustainability,” says Lisa Owen, global business leader for rigid packaging with Cargill Dow LLC. “This holds a special emotional appeal for consumers, especially among those already interested in natural or organic foods.” Owen sees the most immediate potential for NatureWorks PLA in rigid food containers such as berry packs, clamshells, drinking cups, and film applications like food wrap and container lids. Nature-based packaging offers great point-of-sale differentiation for fresh foods like produce, and deli and bakery items. Several leading grocery retailers in North America and Europe are currently using NatureWorks PLA to draw customer attention to their fresh food offerings. Natural foods retailer Wild Oats Natural Marketplace is using clear containers made from NatureWorks PLA in its deli and salad bar sections. Italian hypermarket chain IPER sells a broad range of foods packaged in NatureWorks PLA, 16 L’Actualité chimique canadienne

including produce, fresh pasta and salads, and deli meats and cheeses. IPER also uses paper bread bags with NatureWorks PLA film windows. With its favourable environmental qualities, NatureWorks PLA is also finding a fit with organics, as a way to extend these foods’ allnatural appeal to the entire product offering. Biorigin S.p.A., Italy’s leading organic pasta manufacturer, is packaging its fresh organic pasta specialties in containers and film from NatureWorks PLA. Pennsylvania candy company JoEl Inc. is also wrapping each piece of its new College Farm organic hard candies in clear film of NatureWorks PLA. In addition to food packaging, NatureWorks PLA can be used for other plastic packaging items, ranging from floral wrap to disposable service ware and cutlery.

Bringing NatureWorks PLA to market Cargill Dow’s proprietary process for creating PLA is based on the fermentation, distillation, and polymerization of a simple plant sugar, corn dextrose. The company essentially harvests the carbon stored in

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the sugars and makes a polymer with similar characteristics to traditional thermoplastics. The potential to make plastics from plant sugars was first discovered it in the 1920s by Wallace Corothers, the scientist who invented nylon. But it was only recently that a commercially viable method was developed to produce polymers with the cost and performance necessary to compete with traditional fibres and packaging materials. The breakthrough was the use of fermentation as a costeffective way to produce PLA on a large-scale basis. To produce PLA, the carbohydrates in corn are enzymatically hydrolyzed to sugar and then fermented to lactic acid. Lactic acid is polymerized through a condensation reaction to low molecular weight PLA, which is then depolymerized to form lactide, the cyclic dimer of lactic acid. High molecular weight linear PLA is produced by ring-opening polymerization. Lactic acid exists as d and l stero-isomers. The lactide dimers exist as three forms: D lactide (a dimer of two d-lactic acid units), L lactide (a dimer of two l-lactic acid units)

Feature Article Article de fond

and meso lactide (a dimer of one l- and one d- lactic acid units.) The d-lactic acid content is controlled to adjust the polymer properties. Most notably, the d-lactic acid content affects the crystallinity potential and the melting point. Cargill Dow operates a global-scale facility capable of producing more than 140,000 metric tons (300 million pounds) of NatureWorks PLA per year. The manufacturing plant requires 40,000 bushels of field corn per day and is making commercial-grade resin that is being shipped around the world for use in a wide range of consumer goods. Initially, Cargill Dow is using sugars derived from corn. While the process doesn’t distinguish between plant sugars, an abundant, cost-effective raw material is required to be economically viable. Today, corn is one of the best sources. In the future, NatureWorks PLA will likely be

made using other sources of cellulosic biomass, such as the stalks and leaves, as feedstock. Harnessing these plant parts as the raw material would essentially allow farmers to create a new revenue stream for their crops—one for the grain, and one for the waste. “What Cargill Dow is doing is taking a renewable, abundant crop (corn) and using it as the raw material for a range of consumer goods. This process is a step-change in environmental stewardship,” Owen says.

How NatureWorks™ PLA is Made … and Unmade Annually Renewable Resource (Unrefined dextrose)

A renewable resource such as corn is milled to separate starch from the raw material. Unrefined dextrose is processed from the starch. Future technology enhancements may eliminate the milling step and allow for utilization of even more abundant agricultural by-products.

Fermentation (Lactic acid)

Cargill Dow turns dextrose into lactic acid using a fermentation process similar to that used by beer and wine producers. This is the same lactic acid that’s used as a food additive and is found in muscle tissue in the human body.

Intermediate Production (Lactide)

Through a special condensation process, a cyclic intermediate dimer, referred to as a lactide, is formed.

Polymer Production (Polylactides)

This monomer lactide is purified through vacuum distillation. Ring-opening polymerization of the lactide is accomplished with a solvent-free melt process.

Polymer Modification for Customers.

A wide range of products that vary in molecular weight and crystallinity can be produced, allowing Cargill Dow to modify PLA for a large number of applications.

How it’s Unmade

NatureWorks PLA fits all disposal systems. It is compostable. Products made of NatureWorks PLA can be recycled back to a monomer and into polymers. It is inert in a landfill, producing no leachate or toxins. At the end of its lifecycle, a product made from NatureWorks PLA can be broken down into its simplest parts so that no sign of it remains.

Reduced Fossil Resource Use

Because NatureWorks PLA is derived from annually renewable resources, it uses 20 to 50 percent less fossil resources than comparable petroleum-based plastics.

Reduced CO2 Emissions

Because NatureWorks PLA recycles the earth’s carbon, it potentially reduces the carbon dioxide in the atmosphere. Carbon dioxide is removed from the atmosphere when growing the feed stock crop and is returned to the earth when NatureWorks PLA degrades.

The fact that NatureWorks PLA fits all disposal options differentiates the polymer from competitive materials is. It is fully compostable in industrial facilities, where it breaks down like other matter derived from plants. With the proper infrastructure, products made of NatureWorks PLA can be recycled back to a monomer and into polymers.

Performance without sacrifice While environmentally sound products are highly desired by consumers, performance is the ante for even being considered. What makes NatureWorks PLA such an attractive option is that it offers performance that is on par with existing packaging materials, such as cellophane or oriented plypropylene. Some of the inherent physical properties that the resin provides include high gloss, superior clarity, superb twist retention, excellent optics, strong deadfold, heat-seal ability, and flavour and aroma barrier. “NatureWorks PLA offers a more sustainable future,” says Owen. “It satisfies consumers’ needs to feel good about the entire product they purchase, not just the food. Consumers want to do their part in protecting the environment, and purchasing fresh food packaged in NatureWorks PLA gives them a way to contribute directly.” NatureWorks, the NatureWorks logo and the EcoPLA design are trademarks of Cargill Dow LLC.

January 2004

Canadian Chemical News 17

Feature Article Article de fond

Au Naturel Canadian industry looks toward a global opportunity in the functional food and natural health products market.

n 1998, Health Canada proposed the definition of a functional food to be similar in appearance to a conventional food, consumed as part of the usual diet, with demonstrated physiological benefits, and/or to reduce the risk of chronic disease beyond basic nutritional functions. In the same proposal, Health Canada defined “nutraceuticals” as products sold in dosage form and which have been shown to exhibit a physiological benefit or provide protection against chronic disease. Natural health products (NHP) in Canada include homeopathic preparations, substances used in traditional medicine, a mineral or trace element, a vitamin, an amino acid, an essential fatty acid or other botanical, animal or microorganism-derived substance. These products are generally sold in a medicinal or “dosage” form and have encompassed the product area of “nutraceuticals.” The functional foods and NHP industries have garnered a great deal of attention and enthusiasm on the part of governments, the agri-food sector, and the research community globally. Most recently, Canada has taken notice.

Canada has valuable expertise

Canadian production Canadian companies produce a wide range of functional food and NHP products. Canada’s prairie and forested regions offer an abundant source of wild plants and large areas of fertile land that make the country an ideal location for the cultivation of a wide variety of commodity, specialty and medicinal crops. Along with enhancing the nutritive value and functional properties of common crops, there has been a trend in Canada towards value-added processing and the extraction of nutritionally valuable constituents. Grains such as wheat, oats, and barley are mainstays of the North American diet. These products are high sources of dietary fibre, carbohydrate, and vitamins. Canadian companies such as Saskatoon-based InfraReady Products and Edmonton-based Cevean BioTech, 18 L’Actualité chimique canadienne

have developed specialized fractionation technologies for the processing of raw materials such as legumes, oats and other cereals into starch, protein and fibre, which are used as functional food additives. In addition, specialty crops such as fenugreek produced by Reginabased company Emerald Seed Products are increasingly being cultivated to meet the demands of manufacturers seeking specific raw materials for functional food and NHP products. The range of herbs produced by Canadian companies is diverse. Saskatchewan growers, for example, reported production of over 70 different herbs and spices, principally—echinacea, ginseng, garlic, milk thistle, feverfew, goldenseal, St. John's wort, valerian, ginseng, astragalus, and cayenne. Other herbs include seabuckthorn, anise, fireweed, senega root, sarsasparilla, milk thistle, chamomile, yarrow, calendula, and stinging nettle. These herbs are also common across

in several aspects of functional food and natural health products market Canada. Canadian companies specialize in the standardization of herb and plant extracts and have developed the extraction, isolation, and purification expertise necessary to manufacture herbal products to pharmaceutical standards. Also, companies have developed and refined analytical methods to verify the potency and bio-activity of herbal extracts and other compounds.

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Kelley Fitzpatrick Spice and fruit crops under production across the country include caraway, coriander, mustard, dill, peppermint, cumin, seabuckthorn, blueberry, Saskatoon berry, chokecherry, and buffalo berry. Canadian companies including New Bruswick’s Vaccinium Technologies Inc., have developed technologies and expertise in the extraction, characterization, stabilization, modification, and enhancement of the flavonoid constituents of fruits. Canadian companies such as Montréalbased Institut Rosell-Lallemand produce microorganisms for the dairy, meat, and brewing industries. Microorganisms are also being manufactured as sources of pre and probiotic supplements and food ingredients. NHP and cosmetics derived from elk antler such as elk velvet capsules, powders, and tinctures as well as emu oil, are produced and processed in various parts of Canada. Expertise in the formulation and manufacturing of single and complex vitamins, minerals, and antioxidants is available from a number of Canadian manufacturers. In addition to consumer brands, Canadian companies also offer full-service contract manufacturing of private label vitamin and mineral supplements as well as herbals, specialty, and combination products. The Canadian industry is a leader in the development and manufacturing of essential fatty acid (EFA) products from plant and marine sources including evening primrose oil, flaxseed, borage, hemp, and marine animal oils as well as herbal/EFA condition-specific combination products. Companies such as Saskatoon’s Bioriginal Food and Science Corp. and Halifax’s Ocean Nutrition are producing EFA oils for the global market. Further, Canadian companies have developed specialized encapsulation and other packaging technologies that preserve the integrity and bio-activity of EFA products. Canola, tall and soy sterols and stanols produced by Vancouverbased Forbes Medi-Tech, and flaxseed lignans from Winnipeg-based Pizzey’s Milling, are also sold into the health food

Feature Article Article dehead fond Section

market in the form of capsules, blended with oil or as part of foods. The advent of biotechnology has resulted in the development of innovative manufacturing technologies. Canadian companies manufacture recombinant proteins using both plant and animal transgenic expression systems. These systems are used to produce food processing enzymes, seed meal enhancers, and NHP. Recombinant protein technology offers significant potential for the future development of value-added functional food and NHP products. The food and food ingredient sector is also a very important part of the Canadian nutrition industry. The types of food and food ingredient products produced by Canadian companies are quite diverse and include milk and eggs with increased levels of omega-3 fatty acids, cereals and grains including wheat, oat, barley, and fenugreek products with enhanced amounts of dietary fibre (soluble and insoluble), modified fatty acid vegetable oils, vegetable proteins from soy, canola, hemp, legumes, and fruit products.

annually depending upon the product categories that are included in the statistics. In 2001, the U.S. industry journal Nutrition Business Journal (NBJ) estimated the global market to be approximately $150 billion U.S. NBJ has identified the primary markets for NHP and functional foods as the U.S., Europe, Japan, and Asia which represent 90 percent of global sales. These countries also represent the principal export markets for Canadian products. Since the U.S. is Canada’s largest trading partner, it is the easiest market for Canadian nutritional companies to penetrate. Generally, the largest markets for NHPs and functional foods are countries or regions with greater levels of economic development or more sophisticated economies. These areas are characterized by higher levels of education and greater personal wealth. But the traditional use of herbal remedies is also a factor that impacts consumption by region. Asian countries are large consumers of NHPs and functional foods for cultural reasons, and many of the products we use today have their roots in ancient Chinese medicine.

The Global market

The Canadian market

Current world consumption of NHPs (or dietary supplements in other jurisdictions) and functional foods is estimated to be between $70 and $250 billion

Canadian sales figures for functional foods and NHPs are difficult to interpret as much of it is extrapolated from U.S. sales and adjusted downwards. In addition, strict regulations have forced companies to label products either as foods or drugs. Functional food and NHPs may not be accounted for since they overlap into the food processing or pharmaceutical industries. Estimates are that Canadians purchased approximately US$4.2B worth of dietary supplements (defined as NHPs in Canada) and functional food products in 2001. This translates into nearly $140 per capita spending, a 130 percent increase in only four years. Additional data show that while functional food sales in the U.S. represent approximately 4.5 percent of total food sales, Canada’s portion of total food sales is only 2.2 percent, representing a significant growth potential for the domestic industry. In regard to dietary supplements, Canadian sales figures in 2001 were approximately US$0.8B. Whereas supplements account for almost half of the global nutrition industry, within Canada retails sales account for 21 percent of

total industry sales. Lower figures are believed to be due to stricter regulations that have historically been present in Canada. Compared to the U.S., Canada is

Nutraceuticals in a nutshell The term “nutraceutical” is used to describe medicinally or nutritionally functional foods. Nutraceuticals have also been called medical foods, designer foods, phytochemicals, functional foods, and nutritional supplements. They include such everyday products as “bio” yogurts and fortified breakfast cereals, as well as vitamins, herbal remedies, and even genetically modified foods and supplements. Many different terms and definitions are used in different countries—which can result in confusion. The term “nutraceutical” was coined in 1989 by Stephen De Felice, founder and Chair of the Foundation for Innovation in Medicine, an American organization that encourages medical health research. He defined a nutraceutical as a “food, or parts of a food, that provides medical or health benefits, including the prevention and treatment of disease.” In Canada, a nutraceutical is “a product produced from foods but sold in pills, powders (potions), and other medicinal forms not generally associated with food.” By comparison, a functional food has been defined as being “similar in appearance to conventional foods … consumed as part of a usual diet.” In Britain, the Ministry of Agriculture, Fisheries and Food has developed a definition of a functional food as “a food that has a component incorporated into it to give it a specific medical or physiological benefit, other than purely nutritional benefit.” Hence, in both Canada and in Britain, a functional food is essentially a food, but a nutraceutical is an isolated or concentrated form. In America, “medical foods” and “dietary supplements” are regulatory terms, however “nutraceuticals,” “functional foods,” and other such terms are determined by consultants and marketers, based on consumer trends. Many of these new products that are being promoted to treat various disease states find their origins in the plant kingdom. This is an obvious choice as many plants produce secondary compounds such as alkaloids to protect themselves from infection and these constituents may be useful in the treatment of human infection. There is also a long history of plant use in many cultures which can be used to identify plants with activity in the treatment of disease.

January 2004

Pharmaceutical Journal

Canadian Chemical News 19

Feature Feature Article Aticle Article de fond

Canadian opportunities

generally considered to be between 12 to 18 months behind in launching new NHP products, again believed to be due to a more restrictive regulatory climate.

The Canadian industry Globally, Canada’s participation in the functional food and NHP (including nutraceuticals) industry is growing and is demonstrated through: • Increasing agricultural crop production and development of varieties targeted at enhanced human health; • Development of new technologies that allow for the processing of supplements and ingredients that provide a health benefit; • The increasing emphasis on clinical validation of functional foods and NHPs; • The upsurge in entrepreneurial activity establishing new and innovative companies throughout Canada. The substantial growth of the Canadian functional food and NHP sector reflects the demand for nutritional products based on increasing scientific evidence linking diet to the quality of health. Consumer interest in self-care and alternative medicine is on the rise. According to a recent study conducted for Agriculture and Agri-Food Canada (AAFC), it is estimated that up to CAN1B of farm production value is devoted to supplying the functional foods and NHP sector. This estimate does not include the marine industry, which contributes to the sector through the production of omega-3 fatty acids and other marinebased products. A significant opportunity exists in Canada for functional food and NHP products to positively impact health care costs. In another study conducted for AAFC, it was noted that lifestyle-related chronic disorders are a major component of increasing health care expenditures in this country. The proportion of disease onset attributable to diet is estimated to be approximately 40 to 50 percent for cardiovascular disorders and diabetes, while 35 to 50 percent of all cancers are directly related to dietary factors. Approximately 20 percent of osteoporosis is diet-related. Strong evidence supports the role of functional foods and NHPs in reducing

20 L’Actualité chimique canadienne

the prevalence of chronic disease in Canada and providing impressive savings in health care costs without significant overall dietary changes. Based on the degree to which various chronic disorders are diet-related, and using the current direct medical costs of these disorders, the author estimated potential annual savings to the health care system could be in the magnitude of $20 billion per year. Canadian companies are focusing their product research and development, production and wholesaling in the areas of (by priority): general well-being; immune system; vascular and heart health; energy; diabetes and weight control. There is a growing trend towards marketing NHPs as ingredients in foods. Several recent studies have identified the rapid growth of the industry and the significant potential of functional foods and NHPs to enhance value-added agriculture in the Western Canadian provinces.

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The growing demand for functional foods and NHPs to meet consumers’ desire to lead healthier lifestyles present significant opportunities for Canadian agricultural and marine-based industries. Canada faces the ongoing challenge of having an abundance of natural resources, but a fragmented regionalized industry spread across a vast border with the U.S. Having the U.S. as our largest trading partner, and we theirs, is both a strength and a weakness when trying to develop more value-added opportunities and to sustain an economically viable industry, under free trade. The relatively high growth rate of various segments of the nutritional market is attracting pharmaceutical, chemical, and food processing companies, which increasingly require good sources of raw materials and ingredients. Global companies are interested in sourcing innovative products. Developing and supplying such products represents a significant opportunity for Canadian companies. Additionally, this country has valuable expertise in several aspects of functional food and NHP research, which provides a foundation to building an industry. In short, Canada has the potential of being recognized as a global leader in the production and exportation of functional food ands NHP ingredients and products as well as being a model to the world of a healthy nation driven by a philosophy that fosters health and nutrition. Kelley Fitzpatrick, MSc, is the marketing and research development manager for the Richardson Centre for Functional Foods and Nutraceuticals at the University of Manitoba. She is the founding president of the Saskatchewan Nutraceutical Network (SNN), an organization that she established in early 1998. Under her direction, the SNN, the first network of its kind in Canada, became recognized nationally and internationally as a superior information resource for the Canadian nutraceutical and functional food sector and a leader in industry representation. For more information specific to Canadian companies, visit ats-sea.agr.gc.ca/supply/e3312.htm.

Feature Feature Article Aticle Article de fond

Seeds of Change The growing trend of producing biodegradable polymers from oilseed crops s we begin the new year, as Canadians and citizens of the world, we are being buffeted by winds of change that are both wonderful and strange. The most notorious way in which the world has changed is of course the much clichéd September 11th atrocity, and as the threat of a prolonged war on terrorism looms on the horizon, other drivers of change in the world may go relatively unnoticed. Of course, the Kyoto Accord has received much opposition in Alberta, due to the threats that it may pose to our lucrative oil and gas industry. Clearly, people the world over are becoming more concerned about the environmental impact of our way of life and livelihood, and the European Union seems to be leading the way in endorsing such plans as the Kyoto Accord. Economies like ours which depend so heavily on oil and gas reserves are prudent to take a more measured, though not necessarily less environmentally sound, approach to such accords. At the same time, it is important for Alberta and Canada to begin to think about the fact that our fossil fuel reserves, while still comparatively vast, are finite. We will need to begin to lay foundational plans for the days ahead when these resources begin to dwindle. Based on recent usage trends versus the rate of discovery, the rate of utilization of fossil fuels will be greater than the rate of discovery by 2010. Figure 1 shows the changing sources of feedstock for the chemical industry. What is important for us to realize, is that by clever exploitation of our impressive infrastructure in the oil and gas and petrochemical industries, and our immense agricultural industry, we can begin to address issues of dwindling fossil resources, environmental impact, and economic sustainability. These are large, grandiose times, when the future, not just environmentally, but economically, may be written by the choices we make now. A not-so-small subset of the changes that can be made to our economic and environmental benefit is the production of plastics from renewable agricultural sources. Almost all of the plastics currently produced are from fossil fuel derived feedstock. Clearly, as oil and gas reserves dwindle, the cost and availability of such feed stock will be severely affected.

22 L’Actualité chimique canadienne

Furthermore, a very large percentage of the plastics produced from fossil fuel feedstock are non-biodegradable. Many potential plastics from agricultural feedstock have much more improved biodegradability properties. Consequently, much attention has been focused lately on the use of agricultural feedstock to produce plastics and other industrial materials. Perhaps the most visible of many efforts in this direction has been the Dow-Cargill joint venture to produce biodegradable plastics from Poly Lactic Acid (PLA). However, there has been a steady, growing increase in the amount of research and commercialization activities related to the production of industrial materials from vegetable oils. Given the space allocated for this short

Suresh S. Narine

stored … and some clever applications of physics and biotechnology, and chemistry.

Production of Agricultural Biomass Of the daily energy from sun of approximately 1.5 x 1022 J, only 4 x 1018 J are used to build up biomass. Only approximately 7 percent of the biomass is used by mankind. Furthermore, the buildup of biomass worldwide (~200 billion tons) is approximately 1000 larger than the amount of plastics produced worldwide (~180 million tons). Accepting that this biomass is renewable if sustainable agricultural methods are used, there exists an opportunity to substitute agricultural feedstock for that derived from petroleum, from an avail-

Figure 1

article, it is not possible to cover the use of oilseed fibres in industrial materials. It is important to realize that at the heart of energy and materials utilization by humans, is the humble carbon-carbon bond. The substitution of agricultural and forestry biomass for petroleum products is simply a difference of the amount of time the carbon-carbon bonds, generated ultimately out of photosynthesis, are

janvier 2004

ability perspective. The research challenge becomes the need to match both functionality and price targets set by petroleum-derived plastics. Of the farmed biomass, starch sources are by far the most utilized currently for the production of plastics. However, an exciting development that has occurred over the past few years is the rising utilization of oilseeds as a source for plastics. Figure 2 shows the average produc-

Feature Article Article de fond

tion of vegetable oils worldwide, and that projected for the near future. It is clear that vegetable oil production is on the increase. The exploitation of soybean oil for new industrial purposes has by far outstripped the similar utilization of canola and flaxseed oils (the majority of flaxseed oil that is processed in Canada goes towards

additional 3.987 million metric tonnes. Alberta alone could produce an additional 1.835 million metric tonnes. Flaxseed is the first oilseed to be widely grown in Western Canada. An ancient crop with a wide variety of uses, flax production is small compared to canola in Western Canada, with 20 percent of the area de-

Figure 2

industrial usage, particularly as a drying oil in paints, varnishes, etc.). However, this article also reports on work with canola and flaxseed oils that is taking place at the University of Alberta. More on these efforts appear below. Canola is Canada’s predominant oilseed crop. Saskatchewan produces approximately 50 percent of Canada’s canola production, with Alberta and Manitoba also being major production regions. Canada produces approximately 20 percent of the world’s edible oil supply. Net revenues per acre is the single largest factor in determining the amount of canola grown in Canada’s western provinces, and canola prices are at the mercy of a marketplace which is governed by world oilseed prices. Major increases in soybean oil production in Brazil and China, as well as similar increases in palm oil production in Malaysia, have depressed overall price levels. Consequently, the relative profitability of canola production in Western Canada has been adversely affected, resulting in significant reduction in canola production acreage since 2000. In a report prepared by the Alberta BioPlastics Network, an analysis of the 2002 canola area grown relative to the highest number of hectares grown within the previous 10 years suggests that Western Canada could easily produce an

voted to growing canola being devoted to growing flax. In addition, although in Europe a major use of Flax is in the utilization of its fibres, in Western Canada, the varieties normally grown are the short fibre oilseed varieties. Manitoba and Saskatchewan are by far the largest producers of flaxseed in Canada, with Alberta being a very minor producer. In the same report prepared by the Alberta BioPlastics Network, the 10 year production history of flax in Western Canada illustrates that the current cropping system is capable of considerably more production than what was the case in 2002. If flax cultivation return to peak historical levels, the total additional capacity relative to 2002 production is an additional 345,005 tonnes. What seems clear, however, from an analysis of the production patterns and pressures facing the Canadian oilseed industry, is that if a lucrative industrial alternative to edible utilization is developed, there is ample oilseed acreage that will be devoted to this demand. Clearly, increases in production of edible oils are not going to be fuelled by increases in the demand for edible oil, given the production capacity of countries like Brazil, China, Malaysia, and India. Furthermore, given the use of edible oils in vegetable shortenings and margarines, and

growing concerns over both trans fatty acid content as well as with high-carbohydrate diets in North America, edible uses of vegetable oils are currently being threatened.

Plastics It is interesting to contemplate what our winter holidays would have been like if suddenly all of the items made from plastic were absent. For plastics are so ubiquitous in our environment, it is nearly impossible to find a room in everyday life, much less during the holiday season, where some form of plastic is not contained. If you are like me and have small children who absolutely love having a tree and presents under it to tear apart, then a plastic-free holiday season is a significant challenge (we have 3-year-old triplets—try telling them that this year mom and dad decided plastic is not earthfriendly). If you have an artificial tree, it is made almost entirely of plastic. 99 percent of most toys are plastic. The carpet on which the tree sits is plastic. A significant percentage of the clothes we wear is plastic. Most homes are made from upwards of 75 percent plastic material, etc. In fact, the world consumes approximately 180 million tons of plastics every year. This is a staggering amount, and to put it in context of the oil reserves that are used to make this amount of plastic, it takes approximately 141 MJ/kg of energy to produce Nylon and 76 MJ/kg of energy to produce amorphous PET, so that millions of tons of fossil fuels are required to make the 180 million tons of plastic annually—and this accounts only for the primary processing of the plastic, not for the millions of tons of fossil fuel that are used to further process the plastics into toys, Christmas trees, carpets, house siding, insulation, car panels, and a host of other commonplace items that we take for granted. Primary plastic production consumes approximately 4 percent of the global production of petroleum—2 percent as feedstock for actual plastic production, and 2 percent as the energy source to fuel the process. There exists wonderful market opportunity here! If Canada is able to manufacture plastics which are competitive on a performance, price, and biodegradability basis, there is a great opportunity to marry our petrochemical expertise with our agricultural expertise to create an industry of agricultural plastics. It is important for readers to understand that despite the size of the opportunity, the state of art for producing plastics from agricultural sources

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Canadian Chemical News 23

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is not even close to being able to replace entirely the amount and range of plastics produced from petroleum—particularly from functionality and price perspectives. It is misleading to suggest that modern science has solved the problem of replacing polyethylene, with its various forms and their wide physical functionality, as it is to suggest that we are on the verge of replacing petroleum as a source for the range of modern plastics produced and utilized. The current solutions that have been offered up by researchers which can compete on a price and functionality basis represent an extremely small percentage of the volume of plastics produced annually. However, the opportunity does exist, is growing, and is increasingly being considered an alternative by petrochemical industries. For example, Dupont has indicated that they intend to derive 25 percent of their revenue from non-depletable resources by 2010. This goal will require that they search for novel and innovative methods that will produce chemicals that consumers demand from renewable resources. In addition to DuPont’s goals, other chemical companies such as Dow, Cargill, BASF have initiated programs that will improve the sustainability of the chemicals industry.

Plastics market Information from the American Plastics Council indicates that the overall production and sale of plastics within North America is in the order of 45 million tonnes. This may be broadly divided in to the sales shown in Table 1 below.

The opportunities for oil-based plastics lie mostly in the polyols and polyurethane segment of the market. This does not take into consideration the use of oils as drying oils, industrial solvents, biodiesel, etc. According to a market summary published by the United Soybean Board in February 2000, vegetable oil based polyurethanes are most suited to three markets: polyurethane foams, polyurethane binders, and agricultural film (the last not necessarily being a polyurethane). The total U.S. market size for polyurethane foams is currently approximately 3,000 million pounds, and for polyurethane binders and fillers, approximately 400 million pounds, per annum. Some of the more aggressive market segments include the transportation industry (automotive bumpers, moulded plastic parts like dashboards, etc.), packaging for both the food and retail industry, moulded plastic parts for appliances (including medical devices), the construction industry (with applications in insulation as well as in anything requiring rigid moulded plastic), in carpeting (applications include flexible foam carpet backing, and binders for carpet fibres), and applications related to tanks and pipes (insulation, sealants, etc.). Interesting work being done at the University of Alberta has also shown that elastomeric polyurethanes from vegetable oils may be suitable for medical and laboratory tubing, sealants, and other uses. The estimated market is believed to be greatly understated here, as only the areas where the market entrance should be relatively easy have been discussed. Vegetable oil polyurethanes can also be used as a binder in fibre-reinforced

Resin

Millions of tonnes sold in 2001

PP (Polypropylene)

7.5

PVC (Polyvinyl Chloride)

6.7

HDPE (High Density Polyethylene)

5.1

LLPDE (Linear Low Density Polyethylene)

4.9

LDPE (Low Density Polyethylene)

3.5

Total Thermosets:

3.4

Thermoplastic Polyester

3.2

Other Styrenics, Nylon, Polysuphone

4.4

All others (includes polyurethanes, polyols, isocyanates)

5.8

Total

44.6

Table 1

24 L’Actualité chimique canadienne

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composites. Utilization of fibre-reinforced, thermoset and thermoplastic, composites was 3.5 billion pounds in 1997. Vegetable oil derived binders would be suitable for thermoset resins, with major end markets in automotive panels and other moulded parts, deck planking and other construction uses such as laminates, etc. Currently, agricultural film consists mainly of low-density polyethylene. The total world demand for agricultural film is approximately 1.3 billion pounds per annum. This is an area where biodegradability is very important: it has been estimated that the removal and disposal of agricultural film can be as much as $125 per acre.

Biodegradability In cases where, as in agricultural films, biodegradability is important, it is difficult to use traditional plastics derived from petroleum, although plastics such as polycaprolactone are biodegradable. It is often misconstrued, however, that plastics from renewable sources are always biodegradable. This is certainly not the case, and in many instances, the end use demands that the plastic is not naturally biodegradable. Automotive panelling or construction materials are end uses which require the materials not to naturally biodegrade. In fact, the biodegradable plastics market is relatively small, and many of the opportunities for plastics from renewable sources are in the non-biodegradable plastics sector. In a report by the Alberta Bioplastics Network, the North American demand for biodegradable plastics in 2000 was estimated at 25 million pounds, and was forecasted to increase to 35 million pounds by 2005. The different market segments were loose fill packaging, compost bags, agricultural films, hygiene products, paper coatings, etc. In the same report, the medical plastics markets were estimated at 2 billion pounds in 2000, and was projected to increase at an annual rate of 6 percent to an estimated 2.6 billion pounds by the year 2006. It should be noted that in the case of the medical industry, in those instances where the plastic product must be discarded, biodegradability is required, but only on a “triggered” basis—that is, one does not want ones medical tubing to begin deteriorating while it is in use. In instances like these, polyurethanes from vegetable oils are well suited as an ingredient, for they are biodegradable once they are “triggered.”

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Chemistry The use of vegetable oils such as linseed (flaxseed), tung, lunaria, lesquerella, crambe, rapeseed, castor, veronia, etc., to produce polymers is not new. Plastics are created from these oils by exploiting naturally-occurring epoxide, hydroxyl, and double bond functionality. In cases where hydroxyl and epoxide functionality is required, the double bond has been exploited as a reactive site for chemical reactions to produce such functional groups. Among the oils that are exploited as drying oils due to their carbon-carbon double bond functionality, linseed and tung are the most significant. These oils are used mostly in paints and coatings, as well as in inks and resins. They have iodine values greater than or equal to 150. Soybean oil, sunflower oil and canola oil are semi-drying oils with iodine values between 110 and 150. The major constituents of linseed oil are linolenic acid, linoleic acid and oleic acid. The major constituent of tung oil is eleostearic acid, oleic acid, and linoleic acid. The structures of these major fatty acids of tung and linseed oils are shown in Figure 3.

surface is developed in a short amount of time. Figure 5 shows the relative rate of the drying process for non-conjugated oils. Some vegetable oils contain naturally occurring specialized functional groups, such as epoxy and hydroxyl groups, which make them candidates for crosslinking with various chemical cross-linkers, to form polymeric networks. Castor oil and lesquerella oil (also called pop weed) contain hydroxyl groups in addition to double bonds. Veronia oil contains naturally occurring epoxide functional groups. The structures of the dominant fatty acids of castor, lesquerella, and veronia are shown in Figure 6. Triacylglycerides of ricinoleic and lesquerellic acid both contain three hydroxyl functional groups, and are therefore referred to as triols. The presence of these hydroxyl groups permits cross-linking with such chemical cross-linkers as sebacic acid to form polyesters, or with diisocyanates to form polyurethanes. The epoxide functional group in veronia oil is

Figure 4

Figure 3

The drying power of these oils are directly related to the chemical reactivity conferred on the triglyceride molecules by the carbon-carbon double bonds of the unsaturated acids, which allows them to react with atmospheric oxygen, thus leading to the process of polymerization to form a network. Linseed oil is a non-conjugated oil, rich in polyunsaturated fatty acids (approximate linolenic acid content of 60 percent). These polyunsaturated fatty acids contain double bonds separated by at least two single bonds. These oils dry via a process of autoxidation followed by polymerization. A summary of this is shown in Figure 4.

Figure 5

For tung oil, with mostly conjugated double bonds from eleostearic acid (~77-82 percent eleostearic acid), the rate of autoxidation is much higher than that observed in linolenic acid, due to the conjugation. As a result, the polymerization products from tung oil are highly resistant to water and alkalis, and it dries so rapidly that often a highly wrinkled

typically cross-linked with such dibasic acids as sebacic acid, to form crosslinked polyesters. These groups can also be reacted with various acrylic acids in the presence of a tertiary amine, to create a variety of acrylates, the resulting ester being highly UV active, and therefore easily polymerized through acrylate vinyl moieties.

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Canadian Chemical News 25

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Research underway Research conducted at the University of Alberta has produced a number of elastomer and flexible, semi-rigid and rigid foams from canola and flaxseed oils. This research was performed by the Alberta BioPlastics Network, and significant efforts are currently underway to commercialize the technology that has been created.

Figure 6

In cases where hydroxyl and epoxide functionality do not naturally exist, but are desired, these functional groups can be created by exploiting the existence of double bond functionality. The double bonds can easily be epoxidized, and if hydroxyl groups are required, the epoxidation procedure is usually followed by alcoholysis to form the polyols. Alternatively, the double bonds can be first converted to aldehydes by hydroformylation with either rhodium or cobalt as the catalyst, followed by hydrogenation to hydroxyl groups by hydrogenation with nickel. An example of the double bonds in a soybean oil triacylglyceride being converted to hydroxyl groups is shown in Figure 7.

Acknowledgements The author would like to thank AVAC Ltd., the Alberta Crop Industry Development Fund, the Alberta Agricultural Research Institute, the Agriculture and Food Council, the Alberta Canola Producers Commission, and NSERC, for financial support for the Alberta BioPlastics Network’s research into vegetable oil based plastics. The aid of Dr. Peter Sporns in proofreading this manuscript is also gratefully acknowledged.

References Market Opportunity Summary, Soy-based Plastics, February 2000, United Soybean Board. Lynn Crandall, Bioplastics: A burgeoning industry, Inform, 13, 626–628, 2003. “Biodegradable Polymers from BASF,” a presentation on November 29, 2002, by Scherzer, Freyer, and Kunkel, BASF Plant, Mannheim, Germany. Assessment of Western oilseeds as a feedstock for a bioplastics industry, Jerry Bouma, Alberta BioPlastics Network, May 2003. Dharma Kodali, Biobased Lubricants, Inform, 14, 121–123, 2003 L.H. Sperling and J.H. Manson, J. Am. Oil Chem. Soc., 60, 1887–1892 (1983). L.W. Barrett, G.S. Ferguson and L.H. Sperling, J. Polym. Sci.(Polym. Chem.), 31, 1287–1299, 1993. L.W. Barrett, O.L. Shaffer, and L.H. Sperling, J. Appl. Polym. Sci., 48, 953–968, 1993. L.W. Barrett and L.H. Sperling, Polym. Eng. Sci., 33, 913–922, 1993.

Figure 7

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Z.S. Petrovic, A. Guo and I. Javni, U.S. Pat. 6,107,433, August 22, 2000. A.Guo, Y. Cho, and Z. S. Petrovic, J. Polym. Sci. (Polym. Chem.), 38, 3900–3910, 2000. A.Guo, I. Javni, and Z. Petrovic, J. Appl. Polym. Sci., 77, 467–473, 2000. To learn more about Dupont’s plans to utilize non-depletable resources, visit the discussions entitled, “Sustainability and Integrated Science for the 21st Century” at www.dupont.com/NASApp/dpuontglobal/ corp/index.jsp?page=/content/US/en_US/ news/releases/2003/nr02_17_03.html

Suresh S. Narine of the University of Alberta is the director of the Alberta Bioplastics Network and chair of the Fundamental Science focus area.

The Alberta BioPlastics Network (ABN) is a multi-institutional research network. Its mandate is to engage in activties to promote the use of Alberta's agricultural commodities as feedstock for the production of specialty chemicals and polymers, and significant efforts are currently underway to commercialize the technology that has been created. The institutions that participate in the ABN are: University of Alberta Alberta Agriculture, Food and Rural Development Alberta Research Council Agriculture and Agri-Food Canada Alberta Economic Development Environment Canada Alberta Canola Producers Commission For a full list of the members of the network, or for additional information, please contact business manager Rekha Singh at the Alberta Bioplastics Network, 410 Agriculture Forestry Centre, Agri-Food Materials Science Centre, University of Alberta, Edmonton, AB T6G 2P5. Or call 780-492-9081, or rekha.singh@ualberta.ca.

CIC Bulletin ICC

New ACCN Editorial Board Chair t their November 26, 2003 meeting, the CIC Board of Directors approved the three-year appointment of Terrance Rummery, FCIC, to serve as Chair of the ACCN Editorial Board, effective January 1, 2004. Retired now, Rummery was the former president of

Passing the torch. Former ACCN Editorial Board Chair, Nam F. Han, FCIC, (at right) welcomes Terrance E. Rummery, FCIC, to the helm.

AECL Research. He received both his BSc in engineering chemistry and his PhD in physical chemistry from Queen’s University. Rummery is a Fellow of The Chemical Institute of Canada, the Canadian Academy of Engineering and the Canadian Nuclear Society, and a member of the Association of Professional Engineers of Ontario. Rummery served for three years on the CIC Board of Directors including his 1998–1999 term as Chair.

An International Conference on the Periodic Table high standard of the lectures and the smooth way in which the topics meshed together. The speakers came from as far away as Japan, South Africa, Finland, Russia, Colombia, Hungary, and France. Many chemists seem to assume the periodic table is “carved in stone.” The introductory presentations provided the attendees with an overview of the richness of the history of the table and the fact that the common wall chart form was only devised in 1923. Photo by Fernando Dufour

The stunningly beautiful Kananaskis region of the Rocky Mountains, near Banff, AB, was the setting for an International Conference on the Periodic Table held from July 14 to 20, 2003. Titled “The Periodic Table: Into the 21st Century,” this week-long event focused on current challenges related to the table. The Conference was the second Harry Wiener International Memorial Conference, each conference taking a unique theme but with an emphasis on

Participants in the International Conference on the Periodic Table

quantitative aspects of chemistry. Presentations were almost all by invitation only, which accounted for the very

The next pair of presentations looked at some of the relationships other than groups and periods, such as the diagonal

relationship, the (n) and (n+10) relationship, the Knight’s move relationship, isoelectronic patterns, relationships among the lanthanoids and actinoids, and the concepts of “combo” and pseudo elements. Relativistic effects on the properties of the heavier elements and their compounds were described. These were followed by a detour into nuclear chemistry and the prospects for extending the number of known elements. The atom and its constituent particles were the focus of a pair of presentations on group theoretical approaches to the periodic table. The Madelung Rule for orbital filling was discussed. A discourse on chemical topology was generally agreed to be among the most exciting advances in the study of element relationships. In this particular presentation, physical and chemical data were compiled, relationship trees developed, and then matched to the periodic arrangement. Novel connections between elements in different groups became apparent, while other elements appeared to be “orphans.” Though we usually think of the periodic table as referring to the classification of elements, the term “periodic table” can be more broadly interpreted as an arrangement of chemical species such as to manifest regularities for a variety of properties of species. Using this broader definition, the patterns in diatomic molecules and in di-, tri-, and tetratomic species were discussed. The point was made that there is an astonishing lack of knowledge about many of the theoretically possible diatomic molecules.

January 2004

Canadian Chemical News 27

CSC Bulletin SCC

Photo by Christine Smeaton

The focus then turned to organic chemistry with discourses on a periodic table for alicyclic hydrocarbons. That section concluded with a discussion on the use of a periodic table to deduce a logical system of organic nomenclature.

Tree-mendous ingenuity. Fernando Dufour introduced his three-dimensional periodic table, ElemenTree.

An eclectic set of presentations concluded the forma presentations at the Conference. Canadian Fernando Dufour provided each of the attendees with a model of his three-dimensional periodic table. The conference closed with a session that focused on the future of the periodic table. The wide-ranging discussion included a lengthy debate on whether the table should be considered as a bearer of truth (whatever that may be) of one agreed format, or whether it should be designed for utilitarian purposes, in which case there should be a variety of designs depending upon the needs of the field of chemistry. The debate was not resolved even though it continued informally until departure time. Being in an isolated environment proved to be one of the great advantages of the Conference. The participants ate together and socialized between and after sessions. This enabled some fascinating insights to be developed by employing the combined knowledge bases of individuals from widely different specialties. The Proceedings of the Conference are to be published in 2004. To obtain at copy, contact conference co-organizer, R. Bruce King at rbking@sunchem.chem.uga.edu. Submitted by Geoff Rayner-Canham, FCIC

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Division News Nouvelles des divisions

Distinguished Visitor The president of the Société française de chimie, Armand Lattes, visited Canada in November 2003. His trip provided him with an occasion to meet with representatives of the CSC to discuss topics of common interest to both societies. During his visit, the emeritus professor from Université Paul Sabatier (Toulouse III) attended the 4th International Forum on Science and Society at Cégep Limoilou in Québec City, QC. The annual event, organized by ACFAS, the French-Canadian association for the advancement of sciences, brings together 250 youths with scientists from Europe and Canada. Lattes also presented a conference entitled, “The Chemical students of Stanislas College, a French QC during his stay.

Visiteur distingué

Le président de la Société française de chimie, Armand Lattes, a visité le Canada en novembre 2003. Ce voyage fut prétexte à une rencontre avec des représentants de la Société canadienne de chimie afin de discuter de sujets d’intérêt commun aux deux sociétés. Pendant sa visite, le professeur émérite de l’Université Paul Sabatier (Toulouse III) a participé au 4e Forum international Science et Société au Cégep de Limoilou dans la ville de Québec. L’événement annuel, organisé President of the Société française de chimie, Armand par l’Association canadienne-française Lattes, stands with René Fuchs, headmaster of pour l’avancement des sciences Collège Stanislas, a French lycée in Montréal, QC. (ACFAS) réunit 250 jeunes avec des scientifiques d’Europe et du Canada. Origins of Life” to the Le professeur Lattes a aussi présenté une conférence intitulée lycée located in Montréal, « L’origine chimique de la vie » aux étudiants du Collège Stanislas, un lycée français situé à Montréal, QC, pendant son séjour.

Watch for an article by Lattes in the March 2004 issue of ACCN.

Metal- and MetalloidContaining Macromolecules Symposium Organized by Alaa S. Abd-El-Aziz, FCIC, Ian Manners, FCIC, Hiroshi Nishihara, and Martel Zeldin. 39th IUPAC Congress and 86th CSC Conference in Ottawa This symposium was spread over four half-day sessions and generated great interest with numerous Canadian and international speakers. Based on their lectures, 30 presenters wrote reviews that were recently published in an issue of Macromolecular Symposia (2003, volume 196). The Monday morning program included presentations on supersized metallocenyl dendrimers, ferrocenyl-peptide-cystamines, the ring-opening of organoiron metallocycles, self-assembling watersoluble polyferrocenylsilanes (PFSs), the polymerization of neutral and cationic organoiron complexes, nanolithographic applications of PFS block copolymers, and the development of polychromic displays composed of silica microspheres in a PFS gel matrix. The Monday afternoon session focussed on chain extenders for polyesters and nylon-6, novel poly(methylenephosphine)s and poly(p-phenylenephosphaalkenes, fluorescent materials based on phosphaoligothiophenes, linear and hyperbranched polymers bearing 1,2,3,4,5-pentaphenylsilolyl groups, hybrid resins containing polyhedral oligomeric silsesquioxanes, the use of Wilkinson’s catalyst in silane dehydrocoupling reactions, Lewis acidic organoboron derivatives of polystyrene, and ruthenium macrocycles.

Annonce d’un article écrit par Lattes à paraître dans le numéro d’ACCN de mars 2004.

The Tuesday morning session covered ruthenium-based metallosupramolecular block copolymers, ring-opening routes to polymers containing precious metals, organophosphine dendrimers, superexchange interactions in conjugated metallopolymers, organometallic and nanoporous coordination polymers, and branched functional 3-D polymers. The Tuesday afternoon session focussed on π-conjugated poly metallacyclopentadienes, supramolecular organomanganese coordination polymers, cationic iron azobenzene-substituted polymers, highly metallized PFSs containing cobalt clusters as lithographic resists, the electrochemical behaviour of organoiron and ruthenium polymers, oligo-phenylazomethine derivatives as multidentate ligands, dizinc 1,3-dicarboxylate clusters with nitrogen coordinating ligands, conjugated metallopolymers as chemically tunable electrical conductors and luminescent materials and iridium polymers as oxygen sensors.

Submitted by Alaa S. Abd-El-Aziz, FCIC

January 2004

Canadian Chemical News 29

Division News Nouvelles des divisions

The Canadian

MSED Recognizes Students At the IUPAC/CSC 2003 conference in Ottawa, ON, the Macromolecular Science and Engineering Division (MSED) selected the poster entitled, “Structure and Mechanical Properties of Polyelectrolyte Multilayer Films Studied by AMF,” by Ozzy Mermut of McGill University (supervisor: Christopher J. Barrett, MCIC), for this year’s Xerox-CSC graduate Student Award ($500). Two MSED poster awards ($250 each) were given at the conference. One award was received by Xun Sun of Carleton University (supervisor: Wayne Z. Y, Wang, FCIC) for his work on “Organic Template-Based Soft Processing: A New Strategy for

Society for Chemical Technology offers certification as one of its membership benefits! To learn more, contact Membership Services at 1-888-542-2242.

Ozzy Mermut, winner of the Xerox-CSC graduate Student Award, in front of her poster with Tim Bender, MCIC, Xerox Research Centre of Canada, one of three award selection committee members.

Fabrication of Microstructured Metals on Substrates.” The second award went to the students from Mike Brook’s group at McMaster University: Stefanie Mortimer, an undergraduate student, who has completed year 3 and Amro Ragheb, a PhD student, who presented their work related to the interactions of silicones and proteins and the uses of these materials.

The MSED poster award winners with the award selection committee members. From left to right: Tim Bender, MCIC, Xerox Research Centre of Canada, Xun Sun, Stefanie Mortimer, Even J. Lemieux, FCIC, EJL Consulting, and Harald Stöver, MCIC, McMaster University.

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Local Section News Nouvelles des sections locales

Manitoba Student Awards Night Michael Eze, MCIC, Chair of the Manitoba Local Section, was master of ceremonies for the Manitoba CIC Student Awards Night, and introduced the guest speaker and Manitoba Chemist of the Year, Helene Perreault, MCIC. An audience of over 100 students and faculty from the University of Manitoba, University of Winnipeg, and University of Brandon, and members of the public attended this event at the University of Winnipeg. They listened intently to Perreault’s talk “Scanning M/Z from the FAB-3 to 2003”; a reflection on her career in, and love for, chemistry. Melissa Dowd, Jason Lamontage, Alison Foster, Christina Lang, Angela Paulson, Todd Kruk, and Christa Homenick travelled to the University of Winnipeg to receive recognition for their academic achievements during the 2002–2003 academic year.

Investing their Time Over 25 members of the Vancouver CIC Local Section enjoyed a presentation on “The Chemistry of Investing” by David Chalmers, a senior financial advisor with Rogers Financial Group. The seminar was accompanied by a wine-and-cheese buffet and was held at the Diamond University Centre at Simon Fraser University. The lecture first highlighted general themes of risk vs. reward in investing and covered the pros and cons of mutual funds, stocks, and fixed-income investments. He then focused on chemistry-related investments, particularly with regard to several high-tech companies in the Vancouver area. The issues of patent rights and insider trading were also raised in the discussion afterwards. Both investment neophytes and sophisticated market players gained some insight into their possible future activities. The lecture was generally informative and appreciated by all who attended.

Toronto Section Book Prizes The Toronto CIC Local Section hosted its annual Awards Night on October 24 at University of Toronto. Scott Mabury from the University of Toronto, department of chemistry was the speaker for the evening, speaking on “Finding Fluorine Fascinating.” The Section presented silver medals to students from local universities and colleges. (The list of 2003 medallists from across Canada will be published in the April 2004 issue of ACCN). The Toronto Local Section also sponsors book prizes, awarded to students who have shown the greatest improvement in their academic standing in a chemistry-related program. They are presented for work completed in the penultimate year of a four-year university program or the final year of a college program. The winners include: Julie Kang from Centennial College, biological technology program; Wesam Al-Baik, Durham College, chemical engineering technology; Amelia Deschamps, Durham College, environmental technology; Angella Ormsby, Durham College, food and drug technology; Melanie A. Fisher, Humber College, chemical technology; Andrew Rencius, Humber College, chemical laboratory technician; Aura Leah Balan, Ryerson University, chemical engineering; Kseniya Troyan, Ryerson University, chemistry and biology;

Prempal Bhatti, Sheridan College, chemical engineering technology; Tanya Vuksic, Sheridan College, chemical engineering technology—environmental; Neil James MacKinnon, University of Toronto at Mississauga, chemistry; Alyssa Blair Hall, University of Toronto at St. George, chemical engineering; Cathy Yu, University of Toronto at St. George, chemistry; Catherine Oyiliagu, University of Toronto at Scarborough, chemistry; and Mona Abboud, York University, chemistry. High school students also attended this event to receive awards for the International Chemistry Olympiad and the National High School Chemistry Exam. Arjun Bharioke (Marc Garneau Collegiate Institute) and Jordan Winnick (Northern Secondary School) were winners of the 2003 International Chemistry Olympiad. Don Mills Collegiate Institute’s Dongbo Yu was the winner of the 2003 CIC National High School Chemistry Exam. The Section would like to thank its sponsors for the evening: Acerna Inc., Crompton Co., Dalton Chemical Laboratories, Dominion Colour Corporation, ERCO Worldwide, Fielding Chemical Technologies, Hatch Associates Limited, Innovation Canada In, Maxxam Analytics Inc., National Silicates, Rhodia Canada Inc., Torcan Chemical Ltd., and VWR International.

Submitted by Daniel Leznoff, MCIC, Vancouver CIC Local Section Chair Vancouver CIC Local Section members at the “Chemistry of Investing” seminar.

January 2004

Canadian Chemical News 31

Student News Nouvelle des étudiants

Recognizing Canada’s Student Clubs Students from the CSC, CSChE, and CSCT compete annually to show how hard their chapter/club executives work to put on top quality technical and social events for their peers. Each year the top two Chapters in each Society are recognized with plaques and certificates. • The Canadian Society for Chemistry First Place: University of British Columbia, Undergraduate Chemistry Society Honourable Mention: University of Calgary’s Chemistry Student Chapter • The Canadian Society for Chemical Engineering First Place: McGill University Student Chapter Honorable Mention: Lakehead University Student Chapter • The Canadian Society for Chemical Technology First Place: Mohawk College Student Chapter For details on student activities, visit the student awards on the Web at www.cheminst.ca/awards.html.

Student Chapters’ Merit Award, Terms of Reference The Student Chapters’ Merit Awards are offered as a means of recognizing and encouraging initiative and originality in Student Chapter programming in the areas of chemistry, chemical technology, and chemical engineering. Each Student Chapter shall submit to the manager of Outreach by March 31 (CSCT) and by May 30 (CSC and CSChE) of each year, a report concerning the activities of the Chapter up to that date. These reports will be used by the Selection Committee as a basis for choosing the winning Chapter. Therefore, it is important that the application do justice to the activities of the Chapter. Give indications of both scientific and social events over the entire 12-month period and elaborate on the most important activities. The Awards shall be engraved plaques to be retained by the winning Chapter and lapel pins for executive members of the Chapter. Also, where appropriate, Honourable Mentions may be given to other Student Chapters by the Selection Committee.

32 L’Actualité chimique canadienne

Send your report to: Manager, Outreach and Career Services, The Chemical Institute of Canada, 130 Slater Street, Suite 550, Ottawa, ON K1P 6E2 or e-mail gwilbee@cheminst.ca.

Conditions du prix, prix du mérite Les prix du mérite des chapitres d’étudiants sont offerts afin de reconnaître et d’encourager l’esprit d’initiative et de créativité dans la programmation des activités des chapitres d’étudiants, que ce soit dans les domaines de la chimie, du génie chimique ou de la technologies chimique. Chaque chapitre d’étudiants doit soumettre au plus tard le 31 mars (SCTC) et le 30 mai de chaque année, un rapport à jour des activitiés du chapitre d’étudiants. Le comité de sélection se basera sur les rapports présentés pour choisir le chapitre gagnant. Par conséquent, il importe que le formulaire rende justice aux activités de la section. Dressez la liste des activités scientifiques et sociales qui se sont tenues au cours des 12 derniers mois et expliquez lesquelles de ces activités sont considérées plus importantes. Les prix consisteront d’une plaque que conservera le chapitre gagnant et d’épingles de revers pour les membres exécutifs du chapitre étudiants. De plus, le comité de sélection décernera, s’il y a lieu, des mentions honorables aux autres chapitres étudiants. Envoyer votre rapport à : Directrice, Rayonnement et services d’emploi, l’Institut de chimie du Canada, 130, rue Slater, bureau 550, Ottawa (ON) K1P 6E2 ou par courriel à : gwilbee@cheminst.ca.

2004 CSC Student Conferences • March 20: Southwestern Ontario Undergraduate Student Chemistry Conference (SOUSCC), Trent University, Peterborough, ON. Contact: Andrew Vregdenhil at avreugdenhil@trentu.ca or visit www.trentu.ca/chemistry/souscc2004/ • May 6–8: Western Undergraduate Student Chemistry Conference, University of Manitoba, Winnipeg, MB. Contact: Meghan Gallant at umgallan@cc.UManitoba.CA • May 13–15: ChemCon2004 (CIC-APICS Atlantic Student Chemistry Confer-

janvier 2004

ence), Saint Mary’s University, Halifax, NS. Contact: Kathy Singfield at kathy.singfield@smu.ca or Chris Corbeil at c_corbeill@hotmail.ca • Octobre : Colloque annuel des étudiants et étudiantes de 1er cycle en chimie, Université de Sherbrooke Sherbrooke, QC. Contactez : Pierre Harvey à pharvey@courrier.usherb.ca Visit www.chemistry.ca/stuconf.html for more information as it becomes available.

2004 CSCT Student Symposium The next CSCT Student Symposium will tentatively take place at the British Columbia Institute of Technology on March 3, 2004. For more details as they become available visit www.chem-tech.ca.

First National Undergraduate Chemistry Conference The first annual National Undergraduate Chemistry Conference (NUCC) was held at the University of Ottawa on October 3 and 4, 2003. Almost 70 participants from all provinces attended and gave presentations and posters on undergraduate research projects. The conference provided 21 travel grants, totalling almost $8,000 to help students attend the meeting. Over the two days of the conference, 21 oral and 20 poster presentations were given. A total of $3,500 was available to be won in the presentation competition. Prizes were awarded for the best presentations in organic, inorganic, physical, and analytical chemistry. An overall first prize of $500 cash was also given. The conference prize winners were Jonathan Hudon (McGill) 1st Organic; Timothy Kelly (Memorial) 1st Inorganic; Heather Foucault (Ottawa) 2nd Inorganic. Front row, left to right: Craig Wilson (Acadia) 1st Analytical; Robert Webster (Saskatchewan) 2nd Organic; Paul Boutros (Waterloo) Overall 1st Place; Matthew Graham (Toronto) 1st Physical; Qinzheng Tian (Queen’s) 2nd Physical. Absent: Patrick Beaudette (UBC) 1st Analytical. Keep an eye out for the announcement for the 2nd meeting to be held on October 1–2, 2004!

Student News Nouvelle des étudiants

Next Up: London! Join the CSC for Canada’s next chemistry conference themed, Strong Roots/New Branches, in London, ON, at the London Convention Centre from May 29 to June 1, 2004. Deadline for abstracts is February 9, 2004. For more information go to www.csc2004.ca.

Canada-Wide Science Fair Highlights Top High School Students The Canada-Wide Science Fair is the largest extra-curricular youth activity related to science and technology in Canada, gathering our best young minds together. Each year, some 450 top young scientists are chosen to compete from the ranks of some 25,000 competitions at nearly 100 regional science and technology fairs staged across the country. The Youth Science Foundation administers a regional support program, which helps affiliated regional fairs to send the top competitors to this championship. • The winner of the CIC award for top senior student was FrédéricPicard-Jean and Marie-Hélène Germain from Quebec for their project, “Nos conifers contre le cancer.” • Johanna Johnston from Ontario was awarded the CIC’s top intermediate award for her project, “Now You ‘C’ It, Now You Don’t—The Oxidation of Vitamin C.” • The 2004 regional science fairs will be taking place in March and April. For more information on dates, locations, and contacts, visit www.ysf.ca.

Celebrating Brandon Night! CIC “Brandon Night” was attended by over 30 participants, including 13 student and faculty representatives from the University of Winnipeg and the University of Manitoba. Following the meal, Chris Kingston gave a presentation on “Carbon Nanotubes: Tiny Materials with Enormous Potential” and Michael Sowa gave a presentation on “Optical Spectroscopy Meets Medicine: In-vivo Spectroscopy at the Institute for Biodiagnostics.” Dongbo Yu Shows Excellence in Chemistry The 2004 annual Chemical Institute of Canada (CIC) National High School Chemistry Examination will be written on Tuesday, April 27, 2004. The examination is intended for the best students (first ten percent) and is designed to promote interest in chemistry and to allow students to measure themselves against a national standard. Dongbo Yu of Don Mills Collegiate Institute in Toronto achieved the highest in Canada on the exam in 2003. The following is an excerpt from Dongbo Yu’s essay portion of the exam, which shows the quality of the work from the high school students:

The Octet Rule “The octet rule is likely the most useful way in explaining bonding when learning chemistry. It looks trivial, yet it is unbelievably important; it is easy to learn, yet even easier to be used wrongly, especially in face of numerous headache-causing exceptions. However, there is one thing about this rule that no one can deny. Without it, the field of chemistry would not be what it is today. The basic ‘formula’ of the octet rule is straight forward: each atom tries to have four pairs (8 electrons) around it in order to assume the stable state of the noble gases. For instance, U has seven e-s, so it tries (desperately!) to grab one extra e- from other atoms. Mg, on the other hand, is more than happy to get rid of its two out-shell e-s, in order to become stable. During this process, if one atom needs to have extra electrons while others want to have less, these atoms interact by forming ionic bonds. However, if it happens that both atoms need to have more e- in order to fill their outer-most shell, a competition for e- occurs, and the result is a covalent bond between the two atoms. Each atom donates one electron, and this pair of electrons serve to fill the electron shells of both atoms …”.

January 2004

Canadian Chemical News 33

Careers Carrières Section head

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Careers Carrières Employment Wanted Demandes d’emploi

MSc in Chemical Engineering, BSc (honours) in Engineering Chemistry with 3.9 GPA and professional internship with Celestica International Inc. Experience in chemical analysis, process set-up, trouble-shooting, identification of root cause, problem solving, design and implementation of corrective action, and quality improvement. 2+ years research experience in product development in biochemical and plastics industry. Practical knowledge of modern analytical instrumentation and techniques (NMR, FT-IR spectroscopy, GC, HPLC, GPC, CHDF and ELISA). Contact Marcus Lin at marcuslin_@hotmail.com or call 604-715-0581. Bachelor Chemical Engineer (Honours) with 14 years in the etholylates/propoxylates business is looking for a production and/or commercial development engineer position in a similar field. Has experience with PEG, PPG, ethoxylates propoxylates and alcoxylates. Has worked as a production engineer for 9 years and as a commercial development engineer for 5 years. Contact Peter at 416-614-6603 or pvsaranchuk@yahoo.ca MSc in Chemistry from Queen’s (also BSc in Chemical Engineering with many computer certificates) seeking full-time entry/middle level employment in chemistry (analytical or organic) or related areas at any location in Canada starting from this September. Extensive experience in R&D. Proficient in modern analytical techniques (GC, HPLC, MS, FTIR). Contact me at 613-539-6775 or xingh@chem.queensu.ca. Bachelor Chemical Engineering (Honours) with 14 years in the etholylates/propoxylates business is looking for a production and/or commercial development engineer position in a similar field. Has experience with PEG, PPG, ethoxylates, propoxylates and alcoxylates. Has worked as a production engineer for 9 years and as a commercial development engineer for 5 years. Contact Peter at 416-614-6603 or pvsaranchuk@yahoo.ca.

You’ve got a job opening? You’re looking for a chemical professional? Thousands of Canadian chemical professionals are also looking at this ad. Reach the readers you need. E-mail advertising@accn.ca to book your ad.

Step right up! If you are an unemployed member of the CIC, you are entitled to three consecutive free advertisements in the Employment Wanted section of ACCN. Contact Gale Thirlwall-Wilbee, manager of outreach and employment services. Tel: 613-232-6252, ext. 223; Fax: 613-232-5862; E-mail: gwilbee@cheminst.ca.

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Canadian Chemical News 35

Section Careers head E Section Carrières head Section headF

Available at no charge: Bound copies of Analytical Chemistry, 1937–1984 E-mail cgilmore@dawsoncollege.qc.ca for further information 36 L’Actualité chimique canadienne

janvier 2004

Section head E Events Section head Section headF Événements Section head

Professional Directory Répertoire Professionnel

Canada Seminars and Courses January 19, 2004. Fluid Flow, Mixing, and Heat Transfer, CSChE/EPIC, Toronto, ON. Contact: Educational Programs Innovations Centre (EPIC); Tel.: 1-888-374-2338; Fax: 1-800-866-6343; E-mail: epic@epic-edu.com; Web site: www.epic-edu.com. January 20, 2004. Chemical Engineering Process Design, CSChE/EPIC, Toronto, ON. Contact: Educational Programs Innovations Centre (EPIC); Tel.: 1-888-374-2338; Fax: 1-800-866-6343; E-mail: epic@epic-edu.com; Web site: www.epic-edu.com.

Conferences 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. July 10–14, 2004. 15th Canadian Symposium on Theoretical Chemistry (CSTC 2004), Sainte-Adele, 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.

U.S. and overseas March 28–April 1, 2004. ACS Spring Meeting (227th), Anaheim, CA; Tel.: 800-227-5558; E-mail: natlmtgs@acs.org; Web site: www.acs.org. April 18–24, 2004. 9th World Filtration Congress, New Orleans, LA, American Filtration and Separation Society (AFS). Contact: Wallace Leung; Tel.: 703-538-1000; Fax: 703-538-6305; E-mail: Wallace.Leung@bakerhughes.com; Web site: www.wfc9.org. April 25–29, 2004. AIChE Spring National Meeting, New Orleans, LA; Tel.: 212-591-7330; Web site: www.aiche.org. 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.

Chemical Group

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.

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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. January 2004

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janvier 2004