Synthesis of diethylamine-functionalized soybean oil

被引:83
作者
Biswas, A
Adhvaryu, A
Gordon, SH
Erhan, SZ
Willett, JL
机构
[1] USDA ARS, Plant Polymer Res, Peoria, IL 61604 USA
[2] Penn State Univ, Dept Chem Engn, University Pk, PA 16802 USA
关键词
vegetable oils; epoxidized soybean oil; epoxy ring opening; diethylamine; zinc chloride; aminol preparation;
D O I
10.1021/jf050731o
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Specialty chemicals based on renewable resources are desirable commodities due to their eco-friendly nature and "green" product characteristics. These chemicals can demonstrate physical and chemical properties comparable to those of conventional petroleum-based products. Suitably functionalized amines in the triacylglycerol structure can function as an antioxidant, as well as an antiwear/antifriction agent. In addition, the amphiphilic nature of seed oils makes them an excellent candidate as base fluid. The reaction of amine and epoxidized seed oils in the presence of a catalyst almost always leads to different intra/intermolecular cross-linked products. In most cases, the triacylglycerol structure is lost due to disruption of the ester linkage. Currently, there is no reported literature describing the aminolysis of vegetable oil without cross-linking. Here the epoxy group of the epoxidized soybean oil has been selectively reacted with amines to give amine-functionalized soybean oil. The optimization procedure involved various amines and catalysts for maximum aminolysis, without cross-linking and disruption of the ester linkage. Diethylamine and ZnCl2 were found to be the best. NMR, IR, and nitrogen analysis were used to characterize the products.
引用
收藏
页码:9485 / 9490
页数:6
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