Title: Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis

Abstract

This invention relates generally to olefin metathesis, and more particularly relates to the synthesis of terminal alkenes from internal alkenes using a cross-metathesis reaction catalyzed by a selected olefin metathesis catalyst. In one embodiment of the invention, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting an olefinic substrate comprised of at least one internal olefin with ethylene, in the presence of a metathesis catalyst, wherein the catalyst is present in an amount that is less than about 1000 ppm relative to the olefinic substrate, and wherein the metathesis catalyst has the structure of formula (II) ##STR00001## wherein the various substituents are as defined herein. The invention has utility, for example, in the fields of catalysis, organic synthesis, and industrial chemistry.

Inventors:

Schrodi, Yann ^[1]

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1. Agoura Hills, CA

Issue Date:

Tue Nov 29 00:00:00 EST 2011

Research Org.:

Cargill, Inc.

Sponsoring Org.:

USDOE

OSTI Identifier:

1032632

Patent Number(s):

8067610

Application Number:

11/879,029

Assignee:

Cargill, Inc.

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
B01J31/12 - containing organo-metallic compounds or metal hydrides
B01J31/2265 - {Carbenes or carbynes, i.e.

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

C07C11/02 - Alkenes
C07C2531/18 - containing nitrogen, phosphorus, arsenic or antimony
C07C2531/22 - Organic complexes
C07C2531/24 - Phosphines
C07C2531/28 - of the platinum group metals, iron group metals or copper
C07C6/04 - at a carbon-to-carbon double bond
C07C67/333 - by isomerisation
C07C69/533 - Monocarboxylic acid esters having only one carbon-to-carbon double bond

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

C07F15/0046 - {Ruthenium compounds}

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DOE Contract Number:  

FG36-04GO14016

Resource Type:

Patent

Country of Publication:

United States

Language:

English

Subject:

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY