Synthesis and characterization of phosphonates from methyl linoleate and vegetable oils

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

Submitted to: American Chemical Society Abstracts
Publication Type: Abstract Only
Publication Acceptance Date: 4/18/2017
Publication Date: 4/20/2017
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 Chemical Society Meeting - Illinois Heartland Section, 4/20/17, Peoria, IL. p. 6.

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 radical initiator. A staged addition of the lipid and the initiator was needed to achieve good yields. Good results were observed with MeLin and HOSO using tert-butyl perbenzoate as initiator. With SBO, benzoyl peroxide was used as 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 GC-MS. The products were characterized using 1H-, 13C- and 31P-NMR, and IR. A prolonged reaction led to some transesterification between the carboxylic and 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 a double bond.