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Title: Methods for synthesis of olefins and derivatives

Abstract

The invention provides a method of producing acrylic acid. The method includes contacting fumaric acid with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylic acid per mole of fumaric acid. Also provided is an acrylate ester. The method includes contacting fumarate diester with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylate ester per mole of fumarate diester. An integrated process for process for producing acrylic acid or acrylate ester is provided which couples bioproduction of fumaric acid with metathesis transformation. An acrylic acid and an acrylate ester production also is provided.

Inventors:
; ; ; ;
Publication Date:
Research Org.:
Genomatica, Inc., San Diego, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1257347
Patent Number(s):
9,365,874
Application Number:
13/887,140
Assignee:
Genomatica, Inc. (San Diego, CA) CHO
DOE Contract Number:
FG02-06ER84536; FG02-07ER84865
Resource Type:
Patent
Resource Relation:
Patent File Date: 2013 May 03
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 59 BASIC BIOLOGICAL SCIENCES

Citation Formats

Burk, Mark J., Pharkya, Priti, Van Dien, Stephen J., Burgard, Anthony P., and Schilling, Christophe H. Methods for synthesis of olefins and derivatives. United States: N. p., 2016. Web.
Burk, Mark J., Pharkya, Priti, Van Dien, Stephen J., Burgard, Anthony P., & Schilling, Christophe H. Methods for synthesis of olefins and derivatives. United States.
Burk, Mark J., Pharkya, Priti, Van Dien, Stephen J., Burgard, Anthony P., and Schilling, Christophe H. 2016. "Methods for synthesis of olefins and derivatives". United States. doi:. https://www.osti.gov/servlets/purl/1257347.
@article{osti_1257347,
title = {Methods for synthesis of olefins and derivatives},
author = {Burk, Mark J. and Pharkya, Priti and Van Dien, Stephen J. and Burgard, Anthony P. and Schilling, Christophe H.},
abstractNote = {The invention provides a method of producing acrylic acid. The method includes contacting fumaric acid with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylic acid per mole of fumaric acid. Also provided is an acrylate ester. The method includes contacting fumarate diester with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylate ester per mole of fumarate diester. An integrated process for process for producing acrylic acid or acrylate ester is provided which couples bioproduction of fumaric acid with metathesis transformation. An acrylic acid and an acrylate ester production also is provided.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = 2016,
month = 6
}

Patent:

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  • The invention provides a method of producing acrylic acid. The method includes contacting fumaric acid with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylic acid per mole of fumaric acid. Also provided is an acrylate ester. The method includes contacting fumarate diester with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylate ester per mole of fumarate diester. An integrated process for process for producing acrylic acid or acrylate ester is provided which couples bioproduction of fumaricmore » acid with metathesis transformation. An acrylic acid and an acrylate ester production also is provided.« less
  • The invention provides a method of producing acrylic acid. The method includes contacting fumaric acid with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylic acid per mole of fumaric acid. Also provided is an acrylate ester. The method includes contacting fumarate diester with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylate ester per mole of fumarate diester. An integrated process for process for producing acrylic acid or acrylate ester is provided which couples bioproduction of fumaricmore » acid with metathesis transformation. An acrylic acid and an acrylate ester production also is provided.« less
  • A process is described for converting an alcohol and/or ether feed as hereinafter defined to a hydrocarbon mixture rich in olefins which comprises contacting, under conversion conditions at a conversion reaction temperature of from about 300/sup 0/ to 350/sup 0/C., a feed comprising one or more monohydric alcohols having from about 1 to about 4 carbon atoms, ethers derived therefrom, or mixtures of the alcohols and ethers, with a modified crystalline metalosilicate shape selective acidic zeolite. The metalosilicate is selected from the group consisting of aluminum, gallium, and mixtures thereof, and the zeolite, prior to modification and in the absencemore » of any coke deposited thereon, possesses: (a) the capability of catalyzing the alcohol and/or other conversion reaction; (b) a channel size and structure such as to permit (i) entry of the feed into the zeolite and diffusion to the active acid sites within the zeolite, and (ii) formation of olefin products within the zeolite and diffusion of the products out of the zeolite; and (c) hydrothermal stability at temperatures of at least about 290/sup 0/C. The modification of the zeolite is conducted in a manner sufficient to increase the catalyst life of the zeolite, relative to the absence of the modification when the zeolite is employed as a catalyst for the alcohol and/or ether conversion reaction.« less
  • A lubricant composition is described comprising a major amount of oil of lubricating viscosity and a minor amount of the reaction product of: (A) one or more alpha-beta olefinically unsaturated carboxylic reagents containing two to about 20 carbon atoms exclusive of the carboxyl-based groups with (B) one or more olefin polymers of at least 30 carbon atoms selected from the group consisting of (i) polymers of C/sub 12/-C/sub 30/ mono-olefins with the proviso that the polymers include polymers derived from ethylene and (ii) chlorinated or brominated analogs of (i); reacted with (II) one or more amines, one or more alcohols,more » or a mixture of one or more amines and/or one or more alcohols.« less