Synthesis of diethylamine-functionalized soybean oil.
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.
Biswas
Atanu
A
Plant Polymer and Food and Industrial Oil Research, Agricultural Research Service, U.S. Department of Agriculture, 1815 North University Street, Peoria, Illinois 61604, USA. biswasa@ncaur.usda.gov
Adhvaryu
Atanu
A
Gordon
Sherald H
SH
Erhan
Sevim Z
SZ
Willett
Julious L
JL
D002712:Chlorides / Q000737:chemistry; D004048:Diethylamines / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry; D008153:Lubrication; D009682:Magnetic Resonance Spectroscopy; D013024:Soybean Oil / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared; D017967:Zinc Compounds / Q000737:chemistry
D002712:Chlorides; D004048:Diethylamines; D004852:Epoxy Compounds; D017967:Zinc Compounds; D013024:Soybean Oil; C016837:zinc chloride; C034281:diethylamine