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United States Department of Agriculture

Agricultural Research Service

Title: Lubricants from Epoxidized Soybean Oil by Chemical Modification

Authors
item Hwang, Hongsik
item Erhan, Sevim

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: May 16, 2001
Publication Date: N/A

Technical Abstract: For utilization of vegetable oils as lubricants, the major problems, inadequate oxidative stability and poor low-temperature properties, need to be resolved. Many research groups have focused on adding commercially available additives to the oil, preparing new additives, genetic modification of vegetable oils in an attempt to solve the problem. In this study epoxidized soybean oil was chemically modified to develop soybean oil-based lubricants with good oxidative stability and low pour point. Epoxidized soybean oil was reacted with various alcohols in the presence of a catalytic amount of sulfuric acid to give the ring-opened product. By this reaction, the epoxy group in epoxidized soybean oil was transformed to the functional group of -CH(OR1)CH(OH)-, where the R1 = methyl, 1-butyl, 2-butyl, 1-hexyl, cyclohexyl, neopentyl, or 1-decyl. The 1H NMR spectra of the products indicated that transesterification is accompanied by the ring-opening reaction except when the bulky neopentyl alcohol is used. Subsequent esterification of the product's hydroxy group with an acid anhydride gave some lubricant candidates with the functional group of -CH(OR1) CH(OCOR2)-, where the R2 = CH3 (CH3)2CH-, or CH3(CH2)4- showed the lowest pour points (-39, -39, and 45C, respectively) when 1% of pour point depressant was added. Penn State micro-oxidation test showed that the products have better oxidative stability than soybean oil and epoxidized soybean oil and even better than most petroleum-based lubricant basestocks.

Last Modified: 7/23/2014