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Improving the selectivity for the synthesis of two renewable platform chemicals via olefin metathesis

Paper ID Volume ID Publish Year Pages File Format Full-Text
42511 45928 2009 5 PDF Available
Title
Improving the selectivity for the synthesis of two renewable platform chemicals via olefin metathesis
Abstract

The self-metathesis of methyl 10-undecenoate as well as its cross-metathesis with methyl acrylate was investigated in detail by a systematic variation of the reaction conditions. Unsaturated α,ω-diesters with a chain length of 20 and 12 carbon atoms were thus obtained, respectively. Four different metathesis catalysts were investigated under solvent-free conditions at catalyst loadings ranging from 0.05 mol% to 1 mol% and at temperatures ranging from 30 °C to 90 °C. In the case of the self-metathesis reactions quantitative conversions were obtained with all catalysts, but the second generation metathesis catalysts revealed high amounts of olefin isomerization side reactions at higher temperatures. Using a small quantity of the hydrogen acceptor 1,4-benzoquinone, the isomerization process was almost completely suppressed. Thus, the second generation catalysts allowed for high conversions at very low catalyst loadings. For the cross-metathesis reaction, an interesting temperature and catalyst loading dependent selectivity was observed with the second generation catalysts. Moreover, due to these optimizations, we were able to run these cross-metathesis reactions with a 1:1 ratio of the reactants and low catalysts loadings. This is an improvement over described literature procedures. Thus, we report on the detailed investigation of the described self- and cross-metathesis reactions leading to practical and optimized reaction conditions for the synthesis of unsaturated α,ω-diesters monomers from renewable raw materials in an efficient catalytic manner.

Graphical abstractThe selectivity of self- and cross-metathesis reactions was improved by, e.g., avoiding olefin isomerization side reactions. After optimization of the reaction conditions two α,ω-diesters with a chain length of 20 and 12 carbon atoms were thus obtained from the renewable platform chemical methyl 10-undecenoate.Figure optionsDownload full-size imageDownload as PowerPoint slide

Keywords
Renewable resources; Olefin metathesis; Fatty acids; Green chemistry; Catalysis
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Improving the selectivity for the synthesis of two renewable platform chemicals via olefin metathesis
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 368, Issues 1–2, 31 October 2009, Pages 158–162
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us