Synthesis and characterization of phosphonates from methyl linoleate and vegetable oils

Authors: Bantchev, Grigor; Moser, Bryan; Murray, Rex; Biresaw, Girma

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: 2/22/2017
Publication Date: 4/30/2017
Citation: Bantchev, G.B., Moser, B.R., Murray, R.E., Biresaw, G. 2017. Synthesis and characterization of phosphonates from methyl linoleate and vegetable oils [abstract]. American Oil Chemists' Society Annual Meeting. p. 65.

Interpretive Summary:

Technical Abstract: Phosphonates were synthesized on a medium scale (~200 g) from three lipids: methyl linoleate (MeLin), high-oleic sunflower oil (HOSO) and soybean oil (SBO), and three dialkyl phosphites: methyl, ethyl and n-butyl, using a radical initiator. A staged addition of the lipid and the initiator to the dialkyl phosphite was needed to achieve good yields. Good results were observed with MeLin and HOSO using tert-butyl perbenzoate as the initiator. With SBO, benzoyl peroxide was used as the initiator, due to its capability to generate radicals at a higher rate at a slightly lower temperature, thus shortening the reaction time. The progress of the reaction was monitored with gas chromatography-mass spectrometry. The products were characterized using 1H, 13C and 31P nuclear magnetic resonance, infrared and gel permeation chromatography. A prolonged reaction led to some transesterification between the carboxylic and dialkyl phosphite ester groups. A higher reaction rate led to the formation of more oligomers and benzoate fatty ester byproducts. The benzoate fatty ester byproducts were formed by the attack of a benzoate radical on the double bond.