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Free radical meleation of soybean oil via a single‐step process
Author(s) -
Tran Phuong,
Seybold Ken,
Graiver Daniel,
Narayan Ramani
Publication year - 2005
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-005-5171-7
Subject(s) - maleic anhydride , soybean oil , hydroxyl value , benzoyl peroxide , radical initiator , chemistry , acid value , iodine value , peroxide , organic chemistry , raw material , peroxide value , fourier transform infrared spectroscopy , polymer chemistry , chemical engineering , polymer , copolymer , biochemistry , polymerization , polyurethane , polyol , engineering
In this study a new value‐added product was developed from soybean oil for use as a chemical feedstock. The investigation and optimization of this work resulted in a fast and simple process to maleate soybean oil. An anhydride functionality was introduced into soybean oil through a free radical‐initiated maleation. Two initiators were evaluated, 2,5‐bis( tert ‐butylperoxy)2,5‐dimethylhexane peroxide and di‐ tert ‐butyl peroxide. The effects of reaction time, initiator concentration, maleic anhydride concentration, and reaction temperature were investigated. The maleated soybean oil was characterized using acid value, iodine value, and FTIR spectroscopy. The acid value was directly related to the initial concentration of maleic anhydride, whereas the concentration and type of initiator had little effect on the acid value. The peroxide‐initated functionalization of soybean oil with maleic anhydride in a closed vessel at elevated pressure and temperature was found to proceed by a Diels‐Alder mechanism.