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Acid‐catalyzed condensation of oleic acid into estolides and polyestolides
Author(s) -
Isbell Terry A.,
Kleiman Robert,
Plattner Beth A.
Publication year - 1994
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/bf02541552
Subject(s) - chemistry , oleic acid , perchloric acid , catalysis , condensation , yield (engineering) , montmorillonite , mineral acid , inorganic chemistry , condensation reaction , organic chemistry , nuclear chemistry , biochemistry , aqueous solution , materials science , physics , metallurgy , thermodynamics
Oleic acid, when treated with 1.0 equivalent of perchloric acid at 50°C, produced a 76% yield of polyestolide. The concentration of mineral acid greatly affected the rate of estolide formation, with increased rates under high acid concentrations. Over a range of temperatures from room temperature to 100°C, reaction rates increased at higher temperatures. However, high acid concentrations and temperatures produced undesirable side products, primarily lactones. Other acids catalyze the condensation of oleic acid to form estolide with the following relative rates: HClO 4 >H 2 SO 4 > p ‐toluenesulfonic>BF 3 ·Et 2 O> montmorillonite K‐10>HCl>H 3 PO 4 , HNO 3 . Addition of water impedes the formation of estolide.