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United States Department of Agriculture

Agricultural Research Service

Title: Synthesis and Evaluation of a Series of Alpha-Hydroxy Ethers Derived from Isopropyl Oleate

item Moser, Bryan
item Erhan, Sevim

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: August 16, 2006
Publication Date: December 7, 2006
Citation: Moser, B.R., Erhan, S.Z. 2006. Synthesis and evaluation of a series of alpha-hydroxy ethers derived from isopropyl oleate. Journal of the American Oil Chemists' Society. 83(11):959-963.

Interpretive Summary: A series of organic compounds has been produced from the readily available vegetable oil based material, oleic acid. We have studied these materials with respect to their low temperature performance through determination of both their cloud and pour points. These are important properties for the development of cold flow additives for biodiesel, which suffers from relatively poor low temperature performance. This research benefits the vegetable oil industry by helping to open markets for vegetable oil derived fatty materials for use in biodiesel fuel, another vegetable oil product.

Technical Abstract: Several fatty derivatives with bulky moieties were synthesized by treatment of isopropyl oleate with various alcohols in the presence of sulfuric acid as catalyst to provide a series of alpha-hydroxy ethers in good yield, which were characterized by 1H and 13C NMR, FT-IR and EI-MS. The materials were analyzed for low temperature behavior through cloud point and pour point determination. Isopropyl 9-(2-ethylhexoxy)-10-hydroxystearate derived from technical grade oleic acid was found to be the most desirable derivative due to a combination of low-temperature performance data and economic criteria.

Last Modified: 4/22/2015