CHARACTERIZATION OF MONOMERS PRODUCED FROM THERMAL HIGH-PRESSURE CONVERSION OF MEADOWFOAM AND OLEIC ACIDS INTO ESTOLIDES

被引:14
作者
ISBELL, TA
KLEIMAN, R
ERHAN, SM
机构
[1] New Crops Research, USDA-ARS-NCAUR, Peoria, IL, 61604
关键词
BRANCHED FATTY ACIDS; CIS TRANSISOMERIZATION; ESTOLIDES; LACTONES; MEADOWFOAM; MONOMERS; MONTMORILLONITE; OLEFIN MIGRATION; OLEIC;
D O I
10.1007/BF02637676
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The monomers produced from thermal high-pressure conversion of meadowfoam or oleic acids into estolides were characterized as a complex mixture of fatty acids. Mild reaction conditions produced little change in the starting acids. However, vigorous reaction conditions, e.g. greater-than-or-equal-to 3 h at 250-degrees-C with stirring, significantly altered the starting fatty acids. Cis/trans isomerizaton occurred readily, with the proportion of trans isomers reaching 57%. In addition, the double bonds migrated throughout all positions of the hydrocarbon chain with concentrations diminishing outward from the starting double bond position. Branching was also observed to a small extent under these conditions and was even more pronounced in the absence of water. Lactones were also identified in the reaction mixture, with contents near 16% in the meadowfoam series. All products can be explained via carbocation rearrangement mechanisms that result from protonation of the starting olefins.
引用
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页码:1177 / 1183
页数:7
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