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United States Department of Agriculture

Agricultural Research Service

Title: Chemical Modification of Epoxidized Soybean Oil with Linear and Branched Alcohols for Lubricant Basestocks

Authors
item Erhan, Sevim
item Hwang, Hongsik

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: May 8, 2002
Publication Date: N/A

Technical Abstract: Lubricant basestocks have been prepared by reaction of epoxidized soybean oil with linear and branched alcohols in the presence of sulfuric acid as a catalyst. It was found that, in most cases, considerable amounts of transesterification products are produced during the ring-opening reaction. Fully-transesterifed products incorporating 2-ethyl-1-hexanol and Jarcol I-18T gave pour points of -12 and -30C, respectively. The addition of 1% pour point depressant (PPD) further lowered the pour point to 21C for the product from 2-ethyl-1-hexanol and -36C for the product from Jarcol I-18T. Esterification of resulting hydroxy groups with an acid anhydride provided products containing functional groups of -CH(OR1)CH(OCOR2)- in place of the epoxy group. Structural effect of substituents, R1 and R2 on pour points of the product has been systematically investigated in the presence and absence of 1% PPD. The pour points of the esterified products range from 6 to -42C and from 0 to -48C without and with 1% PPD, respectively, depending upon the R1 and R2 substituents. A modified Penn State micro-oxidation test of three selected products shows these lubricant candidates to have similar or better oxidative stability relative to synthetic lubricant base fluids such as PAO and adipate.

Last Modified: 7/23/2014