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Soybean Oil Fatty Acid Ester Estolides as Potential Plasticizers
Author(s) -
Stolp Lucas J.,
Gronlund Patrick J.,
Kodali Dharma R.
Publication year - 2019
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 - 10.1002/aocs.12214
Subject(s) - degree of unsaturation , chemistry , plasticizer , fatty acid , organic chemistry , fatty acid ester , polyunsaturated fatty acid , stearic acid , long chain fatty acid , phthalate , oleic acid , polymer chemistry , biochemistry
Abstract Fatty acid ester estolides were synthesized from soybean oil and evaluated for plasticizer functionality in poly(vinyl chloride) (PVC). The plasticization ability of the fatty acid ester estolides depends upon the molecular features such as polarity, molecular weight, and branching. The structure of the fatty acid derivatives was modified at the ester head group with various alcohols and the estolide branch was created at the site of unsaturation. Soy fatty acid esters of methanol, iso ‐butanol, 2‐ethylhexanol, and glycerol were prepared to vary the size and polarity at the ester head group. Estolides of these fatty acid esters were prepared using two synthetic routes. In the first route, the fatty acid ester was condensed with an aliphatic acid at the site of unsaturation in the presence of a strong mineral acid. In the second route, the fatty acid ester double bonds were converted to epoxy groups, which were ring opened and acetylated to form acetate estolides. The first synthetic route resulted in low‐average estolide content per fatty acid chain while the second route resulted in a higher estolide content per fatty acid chain. The fatty acid ester estolides compounded with PVC showed good plasticizer properties as evidenced by the rheological properties and reduction in glass transition temperature. The fatty acid ester estolides with a higher estolide content had better plasticizer functionality, comparable to commercial controls.