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Karlsruhe Institute of Technology, Institute of Organic Chemistry, Fritz-Haber-Weg-6, Building 30.42, 76131 Karlsruhe, Germany
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Green Chem., 2012,14, 1728-1735
08 Feb 2012,
26 Mar 2012
First published online
16 Apr 2012
This work presents the synthesis of unsymmetric and symmetric organic carbonates as well as the synthesis of polycarbonates in an efficient and sustainable approach. All reactions were carried out at atmospheric pressure at 80 °C and the use of classic toxic and harmful chemicals, such as phosgene and carbon monoxide, was avoided. The key finding of this manuscript is that the use of 1,5,7-triazabicyclo[4.4.0]dec-5-ene, TBD, an organocatalyst, in combination with dimethyl carbonate (DMC), a non-toxic and renewable starting material, allows the synthesis of the mentioned unsymmetric carbonates in yields of up to 98% under optimized conditions. The structure of the alcohols used for this approach was found to influence the DMC–ROH ratio required to maximize the yield of the desired structure. Finally, the results obtained for the synthesis of low molecular weight building blocks could be transferred to the catalytic synthesis of high molecular weight polycarbonates.
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