Fifth International Conference on Renewable Resources and Biorefineries, 10-12 June 2009, Ghent, Belgium

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Reductive amination of carbohydrate derivatives as a simple route to building blocks for biologically active compounds

5-(Hydroxymethyl)furfural (HMF) has recently attracted a significant amount of revived attention. It is produced from hexoses via acid-catalyzed dehydratation and as a renewable building block used for the conversion to a wide range of useful derivatives. The most remarkable examples are 2,5-furandicarboxylic acid and 2,5-di(hydroxymethyl)furan, used in the production of polymers, and 2,5-dimethylfuran, a potential fuel additive with very promising features. Another group of molecules that can easily be produced from HMF are 2-alkyl- and 2-arylaminomethylfurans. These structures are often found in various types of molecules with pharmacological activity, such as antihistaminics, glutamate modulators, glycine antagonists, muscarinic agonists, renin inhibitors, antifungal agents, kinase inhibitors, etc. In most of the patents covering production of these structures, furfural is used as a starting material. However, these procedures include long reaction times and rather drastic temperature and pressure conditions. On the contrary, the here presented reactions of a two-step reductive amination of HMF were conducted in a very straightforward fashion: water and simple alcohols were used as reaction media, no catalyst was used and very mild conditions were employed. Starting from HMF and several aliphatic and aromatic amines, a small library of novel simple-structured derivatives was produced, in high yields and requiring only minimal purification. Conventional and microwave heating were successfully used as a means of enhancing reaction rates. This route therefore presents a novel way for the production of furan-based renewable building blocks

User friendly and flexible Kiliani reaction on ketoses using microreaction technology

The Kiliani reaction, i.e. the elongation of the carbon chain by means of cyanide addition to the carbonyl group of carbohydrate derivatives, is studied on lower C3-, C4- and C6-ketoses under continuous flow conditions. Depending on the process parameters, the corresponding cyanohydrins or alpha-hydroxycarboxylic acids are obtained. A simple on-line purification of the effluent is studied using cation exchange resins. Reactions provide high yields and selectivity within short residence times, emphasizing the assets of the continuous flow process versus the batch process

Production of biobased HMF derivatives by reductive amination

5-(Hydroxymethyl)furfural (HMF) has recently attracted a significant amount of revived attention as a renewable building block for the conversion to a wide range of useful derivatives. A simple procedure for the conversion of HMF to (5-alkylaminomethyl-furan-2-yl)methanol has now been developed. Reactions were conducted without the use of a catalyst and under very mild conditions. As a proof of concept, a small library of derivatives was produced from HMF and several aliphatic and aromatic amines in high yields and requiring only minimal purification. This route presents a novel way for the production of furan-based renewable building blocks

A guide for the implementation of the REACH regulation: Small and Medium Enterprises (SME)

The novel REACH legislation (EC Regulation Nº 1907/2006) entered into force on June 1st 2007 with a phased implementation over the next 11 years. The “Registration, Evaluation, Authorisation and Restriction of Chemical substances (REACH)” regulation aims at the control of the production and the use of chemical substances, and their impacts on human health and the environment. The regulation demands greater responsibility from industry to provide complete and accurate information on the safety of the chemicals it produces or trades