Title: Methods of making organic compounds by metathesis

Abstract

Described are methods of making organic compounds by metathesis chemistry. The methods of the invention are particularly useful for making industrially-important organic compounds beginning with starting compositions derived from renewable feedstocks, such as natural oils. The methods make use of a cross-metathesis step with an olefin compound to produce functionalized alkene intermediates having a pre-determined double bond position. Once isolated, the functionalized alkene intermediate can be self-metathesized or cross-metathesized (e.g., with a second functionalized alkene) to produce the desired organic compound or a precursor thereto. The method may be used to make bifunctional organic compounds, such as diacids, diesters, dicarboxylate salts, acid/esters, acid/amines, acid/alcohols, acid/aldehydes, acid/ketones, acid/halides, acid/nitriles, ester/amines, ester/alcohols, ester/aldehydes, ester/ketones, ester/halides, ester/nitriles, and the like.

Inventors:

Abraham, Timothy W.; Kaido, Hiroki; Lee, Choon Woo; Pederson, Richard L. J.; Schrodi, Yann; Tupy, Michael John

Issue Date:

2021-02-02

Research Org.:

Wilmar Trading Pte Ltd. (Singapore)

Sponsoring Org.:

USDOE

OSTI Identifier:

1805448

Patent Number(s):

10906861

Application Number:

14/678,749

Assignee:

Wilmar Trading Pte Ltd (Singapore, SG)

Patent Classifications (CPCs):

B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

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B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY

B01J2231/543 - alkene metathesis
B01J2531/821 - Ruthenium
B01J31/2265 - {Carbenes or carbynes, i.e.
B01J31/2278 - {Complexes comprising two carbene ligands differing from each other, e.g. Grubbs second generation catalysts}

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS

C07C11/02 - Alkenes
C07C2531/22 - Organic complexes
C07C2531/24 - Phosphines
C07C6/04 - at a carbon-to-carbon double bond
C07C67/02 - by interreacting ester groups, i.e. transesterification
C07C67/303 - by hydrogenation of unsaturated carbon-to-carbon bonds
C07C67/307 - by introduction of halogen
C07C67/31 - by introduction of functional groups containing oxygen only in singly bound form
C07C67/333 - by isomerisation
C07C67/475 - by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of [IMAGE cpc-sch-C07C-0963.gif] groups between different molecules
C07C69/533 - Monocarboxylic acid esters having only one carbon-to-carbon double bond
C07C69/593 - Dicarboxylic acid esters having only one carbon-to-carbon double bond
C07C69/65 - of unsaturated acids
C07C69/73 - of unsaturated acids
C07C69/734 - Ethers

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07F - ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM

C07F7/1884 - {by dismutation}

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DOE Contract Number:  

FG36-04GO14016

Resource Type:

Patent

Resource Relation:

Patent File Date: 04/03/2015

Country of Publication:

United States

Language:

English