Archive for September, 2012

Sustainability in Chemical Synthesis Conference

Anna Simpson, Deputy Editor of Green Chemistry (pictured below, centre) attended the Sustainability in Chemical Synthesis Conference, held at the Chemistry Department of TU Kaiserslautern from the 16th -18th September. 

Kaiserslautern

From left to right: Lukas Gooßen, Anna Simpson and Oliver Kreye

This meeting was organised by the Sustainable Chemistry Section of the Gesellschaft Deutscher Chemiker (German Chemical Society, GDCh).  The series was started in 2007 to bring scientists from the community of sustainable chemistry together for exchanging ideas and new scientific insights. 

The 2012 scientific programme put an emphasis on state-of-the-art organic synthesis by covering, in particular, methods of carbon-carbon, carbon-hetroatom, and carbon-hydrogen bond formation.  Topics on chemicals from biomass were similarly covered as was the invention of new catalytic processes for achieving valuable new chemical transformations.

The Green Chemistry poster prize was won by Oliver Kreye from the Karlsruhe Institute of Technology (far right in picture above) and it was presented by Professor Lukas Gooßen, co-organiser of the conference (far left in picture above).

The full title of the winning poster was The first catalytic Lossen rearrangement: Sustainable access to Carbamates and Amines, authored by: Oliver Kreye, Sarah Wald and Michael Meier.  You may be interested in ‘meeting our author’ Michael Meier, click here.

Congratulations to Oliver on winning this prize.

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Issue 10 of Green Chemistry now online!

The latest issue of Green Chemistry is now available to read online.

Front cover of Green Chemistry, issue 10, 2012The front cover of issue 10 highlights work by Ulrich Schwaneberg and colleagues from RWTH Aachen University, nova-Institut GmbH and the University of Hamburg, Germany.  The aim of this study was to generate re-engineered cellulases which can match application demands in biorefineries and avoid expensive downstream processing.  The team developed a fluorescence-based high throughput screening method for directed evolution of cellulases, in an effort to improve the activity and resistance of a cellulase in aqueous solutions of deep eutectic solvents and concentrated seawater.  This work opens up new opportunities for the development of cellulases as catalysts for the depolymerisation of cellulose under mild conditions.

Reengineering CelA2 cellulase for hydrolysis in aqueous solutions of deep eutectic solvents and concentrated seawater, Christian Lehmann, Fabrizio Sibilla, Zaira Maugeri, Wolfgang R. Streit, Pablo Domínguez de María, Ronny Martinez and Ulrich Schwaneberg, Green Chem., 2012, 3, 2719-2726

The inside front cover of this issue features work by Eugene Chen and co-workers from Colorado State University who present an efficient process for upgrading 5-hydroxymethylfurfural (HMF) to 5,5′-di(hydroxymethyl)furoin (DHMF), a promising intermediate for kerosene/jet fuel.  The reaction was performed in an ionic liquid [EMIM]OAc and catalysed by N-heterocyclic carbenes.  The process could be completed in 1 hour at an ambient atmosphere and 60-80°C, which are industrially favourable conditions.

Organocatalytic upgrading of the key biorefining building block by a catalytic ionic liquid and N-heterocyclic carbenes, Dajiang (D. J.) Liu, Yuetao Zhang and Eugene Y.-X. Chen, Green Chem., 2012, 3, 2738-2746

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Article collection: Renewable energy

One of the greatest challenges facing society and science is developing alternative, renewable energy sources to traditional (and non-renewable) petroleum products.  Below is a selection of Green Chemistry articles giving you a snapshot of the high quality work we publish in this area.

You can enjoy free access to these articles for a limited time only, so why not take a look?   Stay up-to-date with the latest content in Green Chemistry by registering for our free table of contents alerts.

Etherification and reductive etherification of 5-(hydroxymethyl)furfural: 5-(alkoxymethyl)furfurals and 2,5-bis(alkoxymethyl)furans as potential bio-diesel candidates, Madhesan Balakrishnan, Eric R. Sacia and Alexis T. Bell, Green Chem., 2012, 14, 1626-1634

The fate of bio-carbon in FCC co-processing products, Gabriella Fogassy, Nicolas Thegarid, Yves Schuurman and Claude Mirodatos, Green Chem., 2012, 14, 1367-1371

Liquid hydrocarbon fuels from cellulosic feedstocks via thermal deoxygenation of levulinic acid and formic acid salt mixtures, Paige A. Case, Adriaan R. P. van Heiningen and M. Clayton Wheeler, Green Chem., 2012, 14, 85-89

A technical evaluation of biodiesel from vegetable oils vs. algae. Will algae-derived biodiesel perform?, Gerhard Knothe, Green Chem., 2011, 13, 3048-3065

Production of liquid hydrocarbon fuels by catalytic conversion of biomass-derived levulinic acid, Drew J. Braden, Carlos A. Henao, Jacob Heltzel, Christos C. Maravelias and James A. Dumesic, Green Chem., 2011, 13, 1755-1765

Algae as a source of renewable chemicals: opportunities and challenges, Patrick M. Foley, Evan S. Beach and Julie B. Zimmerman, Green Chem., 2011, 13, 1399-1405

An efficient activity ionic liquid-enzyme system for biodiesel production, Teresa De Diego, Arturo Manjón, Pedro Lozano, Michel Vaultier and José L. Iborra, Green Chem., 2011, 13, 444-451

Production of jet and diesel fuel range alkanes from waste hemicellulose-derived aqueous solutions, Rong Xing, Ayyagari V. Subrahmanyam, Hakan Olcay, Wei Qi, G. Peter van Walsum, Hemant Pendse and George W. Huber, Green Chem., 2010, 12, 1933-1946

Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited, Joseph J. Bozell and Gene R. Petersen, Green Chem., 2010, 12, 539-554

Mechanocatalysis for biomass-derived chemicals and fuels, Sandra M. Hick, Carolin Griebel, David T. Restrepo, Joshua H. Truitt, Eric J. Buker, Caroline Bylda and Richard G. Blair, Green Chem., 2010, 12, 468-474

High-yield conversion of plant biomass into the key value-added feedstocks 5-(hydroxymethyl)furfural, levulinic acid, and levulinic esters via 5-(chloromethyl)furfural, Mark Mascal and Edward B. Nikitin, Green Chem., 2010, 12, 370-373

Ionic liquid tolerant hyperthermophilic cellulases for biomass pretreatment and hydrolysis, Supratim Datta,  Bradley Holmes, Joshua I. Park, Zhiwei Chen, Dean C. Dibble, Masood Hadi, Harvey W. Blanch, Blake A. Simmons and Rajat Sapra, Green Chem., 2010, 12, 338-345

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Solvent guide to replce DCM in chromatography

A quick bench-top solvent guide reference has been developed in order for alternative solvents to dichloromethane (DCM) to be selected for separation of a variety of organic molecules.

Chromatography is widely used by synthetic chemists for purification as it can be broadly applied to a vast range of compounds and is very adaptable.  However, the largest contributor of chlorinated solvent waste in the medicinal chemistry industry is chromatography – primarily DCM.  Given the significant human and environmental toxicities associated with DCM, reduction or ideally replacement of this solvent is important.

Guide to select alternative solvent systems to DCM for ellution of neutral compoundsHere, Joshua Taygerly, Emily Peterson and colleagues from Amgen Inc. and Northeastern University, USA have developed a guide which aims to help synthetic chemists find suitable and more environmentally friendly alternatives to a DCM-solvent system for chromatographic purification of compounds.  The authors selected several ‘drug-like’ molecules which reflected the types of molecules regularly prepared and purified, and separated these into three categories – acidic, basic and neutral (where ‘neutral’ refers to compounds without a carboxylic acid or amine functionality).  They tested several alternative solvent systems and assembled a figure which allows the scientist to find the DCM solvent system that would have been applied to a particular molecule and follow it up vertically to find potentially equivalent systems (see the guide for neutral compounds right).

The primary use of this guide is to provide chemists with a quickly identifiable starting point for selecting alternative solvent systems to DCM.

You can read this article for free until the 17th October 2012!

A convenient guide to help select replacement solvents for dichloromethane in chromatography, Joshua P. Taygerly, Larry M. Miller, Alicia Yee and Emily A. Peterson, Green Chem., 2012, DOI: 10.1039/C2GC36064K

You may also be interested in these articles relating to solvent selection – free to access for 2 weeks:

Searching for green solvents, Philip G. Jessop, Green Chem., 2011, 13, 1391-1398

Expanding GSK’s solvent selection guide – embedding sustainability into solvent selection starting at medicinal chemistry, Richard K. Henderson, Concepción Jiménez-González, David J. C. Constable, Sarah R. Alston, Graham G. A. Inglis, Gail Fisher, James Sherwood, Steve P. Binks and Alan D. Curzons, Green Chem., 2011, 13, 854-862

Green chemistry tools to influence a medicinal chemistry and research chemistry based organisation, Kim Alfonsi, Juan Colberg, Peter J. Dunn, Thomas Fevig, Sandra Jennings, Timothy A. Johnson, H. Peter Kleine, Craig Knight, Mark A. Nagy, David A. Perry and Mark Stefaniak, Green Chem., 2008, 10, 31-36

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Meet our Authors: Liang-Nian He

Liang-Nian He Liang-Nian He is a Professor at Nankai University in China.  His research interests current revolve around carbon dioxide (CO2) chemistry (capture and utilization) and sustainable synthetic chemistry.  Liang-Nian He kindly took a few moments to chat to Green Chemistry

Who or what initially inspired you to become a chemist?

The life of an academic is simple and straightforward and I enjoy working in an academic environment. I became interested in learning chemistry at the age of 12 in junior high school, which aroused my curiosity to know what happens behind such phenomena such as combustion of magnesium in oxygen, and the color change in the acid-base reaction. However, there was very little science education at that time. When I continued my college education, chemistry was taught formally, and my interest developed further. I was so fascinated by the nature of matter and had such a strong passion to understand all the interesting things in nature at the molecular level. Chemistry is such a powerful tool that can create almost anything you want. Accordingly, I definitely pursue a career in the field of chemistry when I was conscious of fundamental importance of chemistry to our society from drugs to dyes, from food to clothing.

What has been the motivation behind your recent research?

Chemical utilization of CO2 as a feedstock, promoter or reaction media for producing materials and fuels is attractive as an integral part of the carbon cycle. In particular, establishing large-scale production using CO2 in industry would be a fascinating dream for synthetic chemists. I am very grateful to Professor Toshiyasu Sakakura (National Institute of Advanced Industry Science and Technology, Japan) for introducing me to this emerging state of the art and exciting field of chemistry.

What do you see as the main challenges facing research in this area?

Click here to read more…

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Continuous-flow alkene metathesis

The self-metathesis of 1-octene was used as a model reaction to demonstrate the performance of a continuous-flow alkene metathesis process using supercritical CO2 as the carrier.

Over the last decade or so, olefin metathesis has become widely recognised as a good, general method to generate new C–C bonds, with an excellent synthetic scope.  Here, an international collaboration of scientists from University Ca’Foscari (Italy), the University of Nottingham (UK) and the University of Sydney (Australia) led by Maurizio Selva have developed a continuous-flow process for heterogeneously-catalysed olefin metathesis.

Their process used a Re2O7 supported catalyst on γ-Al2O3, which although deactivated after the first 100-150 mins of the reaction, could be recycled for at least five subsequent reactions without any loss of performance.  Improving this aspect further will be the focus of future research in this area.  The authors propose that this methodology will be applicable to the metathesis of other terminal olefins in the C6-C12range of liquid compounds.

Read this article for free until the 11th October!

Continuous-flow alkene metathesis: the model reaction of 1-octene catalyzed by Re2O7/γ-Al2O3with supercritical CO2 as a carrier, Maurizio Selva, Sandro Guidi, Alvise Perosa, Michela Signoretto, Pete Licence and Thomas Maschmeyer, Green Chem., 2012, DOI: 10.1039/C2GC35983A    (Advanced Article)

You may also be interested in these articles – free to access for 2 weeks:

Electrostatic immobilization of an olefin metathesis pre-catalyst on iron oxide magnetic particles, Matthew J. Byrnes, Andrew M. Hilton, Clint P. Woodward, William R. Jackson and Andrea J. Robinson, Green Chem., 2012, 14, 81-84

Cross-metathesis transformations of terpenoids in dialkyl carbonate solvents, Hallouma Bilel, Naceur Hamdi, Fethy Zagrouba, Cédric Fischmeister and Christian Bruneau, Green Chem., 2011, 13, 1448-1452

Continuous flow homogeneous alkene metathesis with built-in catalyst separation, Rubén Duque, Eva Öchsner, Hervé Clavier, Fréderic Caijo, Steven P. Nolan, Marc Mauduit and David J. Cole-Hamilton, Green Chem., 2011, 13, 1187-1195

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4th International IUPAC Conference on Green Chemistry

The  4th International IUPAC Conference on Green Chemistry (4th ICGC) was held in Foz do Iguaçu, Brazil between the 25-29th August 2012.  The conference focused on broad topics including benign synthesis/processes, green chemistry for energy production, chemicals from renewable resources, green engineering, education in green chemistry and engineering and policy. 

The conference was attended by the Editor, Sarah Ruthven and several members of the Journal’s Editorial and Advisory Boards spoke at the event, including Professor Buxing Han, Professor Paul Anastas, Professor James ClarkProfessor Philip Jessop, Professor Robin Rogers and Professor Roger Sheldon

The Green Chemistry poster prize which was presented by Professor Buxing Han was awarded to Tiago Artur da Silva from the University of Sao Paulo (pictured right). 

The full title of the poster was: AuPd nanoparticles: reusable magnetic responsive catalyst for green oxidation of alcohols; by Tiago Artur da Silva, Érico Teixeira-Neto, Liane Marcia Rossi.

Congratulations to Tiago on winning this prize.

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How synthetic organic chemistry can help to feed the world

Azoxystrobin is the world’s leading agricultural fungicide. It is a fully synthetic compound, whose invention was inspired by the structure and activity of the naturally-occurring fungicide strobilurin A. Today it is used worldwide to control fungi growing on over 120 types of crop, improving plant health, raising quality and increasing yield. The success of the project highlights the crucial importance of chemistry in meeting grand challenges such as global food security and the broader applicability of skills such as natural product synthesis. Keynote speaker Dr John Clough led the team of chemists at Syngenta that invented azoxystrobin. He will discuss the key role that synthetic organic chemistry played in creating an effective and safe fungicide. This policy event is organised by the Royal Society of Chemistry as part of a series of lectures designed to bring together active researchers and policy makers to highlight the role of the chemical sciences in tackling societal issues.

Be inspired - The Chemistry Centre

This event will be held in the Chemistry Centre on 26 September at the RSC’s recently refurbished building in Burlington House, London. Doors will open at 17:30 for refreshments. The event will begin at 18:00 and will finish with a wine reception. Please follow the link here for information and to register for the event.

If you cannot make it why not watch the video of the event which will be uploaded on the website after the event.

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What’s new with carbon dioxide?

In this tutorial review, Donald Darensbourg and Stephanie Wilson highlight the recent advances in the copolymerisation of carbon dioxide (CO2) with epoxides (oxiranes) to produce polycarbonates.

The advances in this area are discussed with specific reference to catalysts that have been designed to afford high selectivity for the copolymer versus cyclic carbonate formation.  The authors not only illustrate the advances in poly(propylene carbonate) (PPC) production by also investigate the underlying reasons for the differences in the reactivity of propylene oxide and cyclohexene oxide. 

Darensbourg and Wilson conclude by highlighting the need for improved catalysts which can prevent the degradation of PPC in the presence of azide ions – specifically those catalysts with appended amines or ammonium salts. 

Interested?  Read the full article for free until the 2nd October 2012

What’s new with CO2? Recent advances in its copolymerization with oxiranes, Donald J. Darensbourg and Stephanie J. Wilson, Green Chem., 2012, DOI: 10.1039/C2GC35928F

You may also be interested in this critical review article – free to access for 2 weeks:

Synthesis of cyclic carbonates from epoxides and CO2, Michael North, Riccardo Pasquale and Carl Young, Green Chem., 2010, 12, 1514-1539

Stay up-to-date with the latest content in Green Chemistry by registering for our free table of contents alerts.

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