Methods of refining and producing dibasic esters and acids from natural oil feedstocks
AssigneeElevance Renewable Sciences, Inc.
InventorsThomas E. Snead, Steven A. Cohen, Demond L. Gildon
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Abstract
Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.
Claims21
A method of refining a natural oil, comprising:
- providing a feedstock comprising a natural oil;
- reacting the feedstock in a metathesis reactor in the presence of a first metathesis catalyst to form a metathesized product comprising olefins and esters;
- separating the olefins in the metathesized product from the esters in the metathesized product;
- transesterifying the esters in the presence of an alcohol to form a transesterified product comprising a terminal olefin ester having the following structure:
- wherein X is a C3-C18 saturated or unsaturated alkyl chain, and R is an alkyl group;
- and
- reacting the terminal olefin ester with an internal olefin ester in the presence of a second metathesis catalyst to form a dibasic ester.
A method of refining a natural oil, comprising:
- providing a feedstock comprising a natural oil;
- reacting the feedstock in a metathesis reactor in the presence of a first metathesis catalyst to form a metathesized product comprising olefins and esters;
- separating the olefins in the metathesized product from the esters in the metathesized product;
- transesterifying the esters in the presence of an alcohol to form a transesterified product comprising 9-decenoic acid ester;
- and
- reacting the 9-decenoic acid ester with 9-dodecenoic acid ester in the presence of a second metathesis catalyst to form 9-octadecene dioic acid ester.
Dependencies are inferred from the claim text.