Silylation of Non-Terminal Double Bonds of Natural Oils

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• 作者：Chetan Tambe ; Sudhanwa Dewasthale ; Xiangke Shi ; Daniel Graiver ; Ramani Narayan
• 关键词：Silylation ; Vinyltrimethoxysilane ; ‘Ene’ reaction ; Soybean oil ; Triglyceride
• 刊名：SILICON
• 出版年：2016
• 出版时间：January 2016
• 年：2016
• 卷：8
• 期：1
• 页码：87-98
• 全文大小：942 KB
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• 作者单位：Chetan Tambe (1)
  Sudhanwa Dewasthale (1)
  Xiangke Shi (1)
  Daniel Graiver (1)
  Ramani Narayan (1)
  
  1. Department of Chemical Engineering and Materials Science, Michigan State University, East Lansing, MI, 48824, USA
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Inorganic Chemistry
  Materials Science
  Organic Chemistry
  Polymer Sciences
  Biomedical Engineering
  Nanotechnology
  
• 出版者：Springer Netherlands
• ISSN：1876-9918

文摘

Silylation of non-terminal double bonds of unsaturated fatty acids with reactive organosilicons was successfully accomplished using the ‘Ene’ reaction route. The ‘Ene’ reaction, which is a subset of the famous Diels Alder reaction, enables grafting of vinyl silanes onto unsaturated organic molecules irrespective of the position of the double bond. This procedure was used to graft vinyltrialkoxysilanes onto unsaturated fatty acids of various triglyceride oils. Methyl oleate and methyl stearate were used as model compounds to investigate this reaction. 1H NMR and TGA were used to characterize the structure of the silylation products and to determine the extent of grafting as a function of reaction conditions. It was found that this grafting reaction follows a second order kinetics. Under extreme conditions a silyl-ester redistribution reaction can also occur where an alkoxy group attached to the silicon atom is exchanged with an alkoxy group of the organic ester. Grafting vinyltrimethoxysilane onto natural oils such as soybean, canola and Abyssinian oils leads to a convenient one-component, moisture activated cure system of these natural oils. Keywords Silylation Vinyltrimethoxysilane ‘Ene’ reaction Soybean oil Triglyceride