Location: Bio-oils Research Unit
Title: Radical-initiated reaction of methyl linoleate with dialkyl phosphites Authors
Submitted to: Society of Tribologists and Lubrication Engineers
Publication Type: Abstract Only
Publication Acceptance Date: December 17, 2013
Publication Date: May 18, 2014
Citation: Bantchev, G.B., Biresaw, G. 2014. Radical-initiated reaction of methyl linoleate with dialkyl phosphites [abstract]. Society of Tribologists and Lubrication Engineers Annual Meeting & Exhibition. p.151. Technical Abstract: Methyl oleate is typically used as a model compound for vegetable oil, since it is bio-based, and has the ester group and the double bond group functionalities of the vegetable oil. Nevertheless, it is not the best representative for most of the commodity oils – the linoleic acid (possessing two double bonds rather than one) is much more prevalent than oleic in soybean, corn, sunflower, and other oils. In previous work by us and other authors, phosphonates have been synthesized by the radical-initiated addition of dialkyl phosphites (methyl, ethyl, or n-butyl) to the carbon-carbon double bonds of methyl oleate. In the current work, we report on analogous synthesis, i.e. where the methyl linoleate has been used instead of methyl oleate. Bis-phosphonates were synthesized, and their structures and spectra reported. The optimization of the synthetic procedure (initiators, temperature, etc.) is reported.