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2013|14 Annual Report Fraunhofer IGB

96 CHEMISTRY Terpenes as raw materials Biomass is gaining more and more importance as a feedstock for the production of bulk and fine chemicals, thus replacing the limited supply of fossil resources such as oil or gas. Ter- penes, for example, have been used for centuries as essential oils in medicine and for flavors and fragrances. They are abun- dant and inexpensive as they accumulate as waste streams in industrial processes such as cellulose production from coni- fers, making them an ideal starting point for the development of new chemicals and materials. The Fraunhofer Project Group BioCat focuses on the development of new catalytic processes for the targeted functionalization of terpenes in order to pro- duce novel bulk and fine chemicals. Chemo-enzymatic catalysis The selective functionalization of terpenes is a major chal- lenge which can be addressed by combining biotechnological and chemical catalysts. To achieve this, the Fraunhofer Project Group BioCat uses P450 monooxygenases from natural and engineered enzyme libraries for the stereo- and regioselective oxyfunctionalization of terpenes. The targeted introduction of hydroxyl groups can already lead to a new product although the further modification of these hydroxyl groups by chemi- cal synthesis results in a much broader product portfolio. Through oxidation and amination bio-derived mono-, di- and polyamines can be synthesized to create interesting building blocks for the chemical industry. New catalytic processes for the production of novel molecules The combination of P450 monooxygenase with an alcohol dehydrogenase resulted in an enzymatic cofactor neutral and a very efficient production process for diketocamphene. The further reduction of this molecule to a diol was successfully performed with a ruthenium-based catalyst. Besides, the amination of the diketone to the corresponding diamine was performed using a palladium catalyst. Therefore the combina- tion of a natural enzymatic system from Pseudomonas putida with heterogeneous catalysts led to the production of new camphor-based bifunctional molecules. Purification and analysis GC as well as HPLC specific protocols for the selective detec- tion of the synthesized functional groups were established and validated for the analysis of these new compounds. We also used NMR analysis to determine the configuration of the products. For this task and for future application tests by our customers, the molecules have to be purified from the synthe- sis broth. A quick and easy extraction process was developed for this purpose. NEW CHEMICAL BUILDING BLOCKS FROM TERPENOID WASTE STREAMS Dr. rer. nat. Michael Hofer 1

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