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Title: Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks

Abstract

Methods are provided for refining natural oil feedstocks and producing isomerized esters and acids. The methods comprise providing a C4-C18 unsaturated fatty ester or acid, and isomerizing the fatty acid ester or acid in the presence of heat or an isomerization catalyst to form an isomerized fatty ester or acid. In some embodiments, the methods comprise forming a dibasic ester or dibasic acid prior to the isomerizing step. In certain embodiments, the methods further comprise hydrolyzing the dibasic ester to form a dibasic acid. In certain embodiments, the olefin is 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 unsaturated esters.

Inventors:
; ; ; ; ; ; ; ;
Publication Date:
Research Org.:
Elevance Renewable Sciences, Inc., Woodridge, IL (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1260249
Patent Number(s):
9,382,502
Application Number:
13/827,798
Assignee:
Elevance Renewable Sciences, Inc. (Woodridge, IL) DOEEE
DOE Contract Number:
EE0002872/001
Resource Type:
Patent
Resource Relation:
Patent File Date: 2013 Mar 14
Country of Publication:
United States
Language:
English
Subject:
09 BIOMASS FUELS; 59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Snead, Thomas E., Cohen, Steven A., Gildon, Demond L., Beltran, Leslie V., Kunz, Linda A., Pals, Tessa M., Quinn, Jordan R, Behrends, Jr., Raymond T., and Bernhardt, Randal J. Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks. United States: N. p., 2016. Web.
Snead, Thomas E., Cohen, Steven A., Gildon, Demond L., Beltran, Leslie V., Kunz, Linda A., Pals, Tessa M., Quinn, Jordan R, Behrends, Jr., Raymond T., & Bernhardt, Randal J. Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks. United States.
Snead, Thomas E., Cohen, Steven A., Gildon, Demond L., Beltran, Leslie V., Kunz, Linda A., Pals, Tessa M., Quinn, Jordan R, Behrends, Jr., Raymond T., and Bernhardt, Randal J. 2016. "Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks". United States. doi:. https://www.osti.gov/servlets/purl/1260249.
@article{osti_1260249,
title = {Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks},
author = {Snead, Thomas E. and Cohen, Steven A. and Gildon, Demond L. and Beltran, Leslie V. and Kunz, Linda A. and Pals, Tessa M. and Quinn, Jordan R and Behrends, Jr., Raymond T. and Bernhardt, Randal J.},
abstractNote = {Methods are provided for refining natural oil feedstocks and producing isomerized esters and acids. The methods comprise providing a C4-C18 unsaturated fatty ester or acid, and isomerizing the fatty acid ester or acid in the presence of heat or an isomerization catalyst to form an isomerized fatty ester or acid. In some embodiments, the methods comprise forming a dibasic ester or dibasic acid prior to the isomerizing step. In certain embodiments, the methods further comprise hydrolyzing the dibasic ester to form a dibasic acid. In certain embodiments, the olefin is 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 unsaturated esters.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = 2016,
month = 7
}

Patent:

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  • 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.
  • 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.
  • Methods and systems for making dibasic esters and/or dibasic acids using metathesis are generally disclosed. In some embodiments, the methods comprise reacting a terminal olefin ester with an internal olefin ester in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In some embodiments, the terminal olefin ester or the internal olefin ester are derived from a renewable feedstock, such as a natural oil feedstock. In some such embodiments, the natural oil feedstock, or a transesterified derivative thereof, is metathesized to make the terminal olefin ester or the internal olefin ester.
  • The present invention relates to an integrated method and system for the simultaneous production of biodiesel from free fatty acids (via esterification) and from triglycerides (via transesterification) within the same reaction chamber. More specifically, one preferred embodiment of the invention relates to a method and system for the production of biodiesel using an electrodeionization stack, wherein an ion exchange resin matrix acts as a heterogeneous catalyst for simultaneous esterification and transesterification reactions between a feedstock and a lower alcohol to produce biodiesel, wherein the feedstock contains significant levels of free fatty acid. In addition, because of the use of amore » heterogeneous catalyst, the glycerol and biodiesel have much lower salt concentrations than raw biodiesel produced by conventional transesterification processes. The present invention makes it much easier to purify glycerol and biodiesel.« less
  • A method of refining a natural oil includes: (a) providing a feedstock that includes a natural oil; (b) reacting the feedstock in the presence of a metathesis catalyst to form a metathesized product that includes olefins and esters; (c) passivating residual metathesis catalyst with an agent that comprises nitric acid; (d) separating the olefins in the metathesized product from the esters in the metathesized product; and (e) transesterifying the esters in the presence of an alcohol to form a transesterified product and/or hydrogenating the olefins to form a fully or partially saturated hydrogenated product. Methods for suppressing isomerization of olefinmore » metathesis products produced in a metathesis reaction, and methods of producing fuel compositions are described.« less