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Title: Methods of refining and producing dibasic esters and acids from natural oil feedstocks

Abstract

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.

Inventors:
; ;
Publication Date:
Research Org.:
Elevance Renewable Sciences, Inc., Woodridge, IL (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1257360
Patent Number(s):
9,365,487
Application Number:
14/048,673
Assignee:
Elevance Renewable Sciences, Inc. (Woodridge, IL) DOEEE
DOE Contract Number:
EE0002872/001
Resource Type:
Patent
Resource Relation:
Patent File Date: 2013 Oct 08
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 09 BIOMASS FUELS

Citation Formats

Snead, Thomas E., Cohen, Steven A., and Gildon, Demond L. Methods of refining and producing dibasic esters and acids from natural oil feedstocks. United States: N. p., 2016. Web.
Snead, Thomas E., Cohen, Steven A., & Gildon, Demond L. Methods of refining and producing dibasic esters and acids from natural oil feedstocks. United States.
Snead, Thomas E., Cohen, Steven A., and Gildon, Demond L. 2016. "Methods of refining and producing dibasic esters and acids from natural oil feedstocks". United States. doi:. https://www.osti.gov/servlets/purl/1257360.
@article{osti_1257360,
title = {Methods of refining and producing dibasic esters and acids from natural oil feedstocks},
author = {Snead, Thomas E. and Cohen, Steven A. and Gildon, Demond L.},
abstractNote = {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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = 2016,
month = 6
}

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 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 amore » 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.« less
  • This patent describes a method for demetalizing Group IIA and/or Group VIII metals from hydrocarbonaceous feedstock. It comprises mixing the hydrocarbonaceous feedstock with an aqueous solution of a metals sequestering agent. The agent comprising dibasic carboxylic acid or salts thereof; and separating the substantially demetalated hydrocarbonaceous feedstock from the aqueous solution; wherein the feedstock to be demetalated is selected from the group consisting of crude petroleum, atmospheric or vacuum residua, solvent deasphalted oil derived from these crudes or residua, shale oil, liquefied coal, and tar sand effluent.
  • 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