Silylation of Non-Terminal Double Bonds of Natural Oils

Chetan Tambe, Sudhanwa Dewasthale, Xiangke Shi, Daniel Graiver, Ramani Narayan

Research output: Contribution to journalArticle

  • 2 Citations

Abstract

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.

LanguageEnglish (US)
JournalSilicon
DOIs
StateAccepted/In press - Jun 12 2015

Profile

Oils
Unsaturated fatty acids
Unsaturated Fatty Acids
Esters
Silanes
Stearates
Silicon
Grafts
Triglycerides
Moisture
Nuclear magnetic resonance
Atoms
Molecules
Kinetics
alkoxyl radical

Keywords

  • Silylation
  • Soybean oil
  • Triglyceride
  • Vinyltrimethoxysilane
  • ‘Ene’ reaction

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials

Cite this

Tambe, C., Dewasthale, S., Shi, X., Graiver, D., & Narayan, R. (Accepted/In press). Silylation of Non-Terminal Double Bonds of Natural Oils. Silicon. DOI: 10.1007/s12633-015-9299-2

Silylation of Non-Terminal Double Bonds of Natural Oils. / Tambe, Chetan; Dewasthale, Sudhanwa; Shi, Xiangke; Graiver, Daniel; Narayan, Ramani.

In: Silicon, 12.06.2015.

Research output: Contribution to journalArticle

Tambe C, Dewasthale S, Shi X, Graiver D, Narayan R. Silylation of Non-Terminal Double Bonds of Natural Oils. Silicon. 2015 Jun 12. Available from, DOI: 10.1007/s12633-015-9299-2
Tambe, Chetan ; Dewasthale, Sudhanwa ; Shi, Xiangke ; Graiver, Daniel ; Narayan, Ramani. / Silylation of Non-Terminal Double Bonds of Natural Oils. In: Silicon. 2015
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