The chemistry of metathesized soybean oil

New materials derived from metathesized soybean oil have been prepared and characterized. Thermal polymerization of metathesized soybean oil in the presence of air results in yellow, brittle gels. These materials display a curious tendency to produce audible popping sounds when exposed to chlorinate...

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Bibliographic Details
Published in:Journal of the American Oil Chemists' Society 1999-01, Vol.76 (1), p.99-102
Main Authors: Rufvik, M.D. (Iowa State University, Ames, IA.), Larock, R.C
Format: Article
Language:English
Subjects:
Acoustics
Applied sciences
Catalysts
Chemical industry and chemicals
Chloroform
Dichloromethane
Epoxidation
Exact sciences and technology
Gels
Hydrogen embrittlement
Hydrogen peroxide
hydrogenation
infrared spectra
Manufacturing and processing
metathesized soybean oil
Molecular weight
nuclear magnetic resonance spectra
Oils and fats
Organic solvents
Oxidants
Oxidizing agents
Palladium
polymerization
PROCESAMIENTO
PROCESSING
PRODUCTOS DE LA SOJA
PRODUIT A BASE DE SOJA
Soybean oil
SOYBEAN PRODUCTS
Soybeans
TRAITEMENT
Vegetable oils
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Summary:New materials derived from metathesized soybean oil have been prepared and characterized. Thermal polymerization of metathesized soybean oil in the presence of air results in yellow, brittle gels. These materials display a curious tendency to produce audible popping sounds when exposed to chlorinated organic solvents, such as chloroform or dichloromethane. Complete hydrogenation of metathesized soybean oil has been accomplished in excellent yields utilizing 10% palladium on carbon in dichloromethane. A new, very mild, effective epoxidation procedure for soybean oil, utilizing methyltrioxorhenium (VII) (MTO) and pyridine as the catalyst system and hydrogen peroxide as the oxidant, has been developed. This epoxidation reaction affords excellent yields of epoxidized soybean oil with some control of the degree of epoxidation at very low MTO concentrations (< 0.5 mol%). This reaction is also very effective for the epoxidation of metathesized soybean oil to higher molecular weight epoxidized soybean oil materials.
ISSN:0003-021X
1558-9331
DOI:10.1007/s11746-999-0054-y