DOE Patents title logo U.S. Department of Energy
Office of Scientific and Technical Information

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:
Issue Date:
Research Org.:
DOESC (USDOE Office of Science (SC) (United States))
Sponsoring Org.:
USDOE
OSTI Identifier:
1087885
Patent Number(s):
8481747
Application Number:
13/234,542
Assignee:
Elevance Renewable Sciences, Inc. (Bolingbrook, IL)
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
DOE Contract Number:  
FG36-04GO14016
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Schrodi, Yann. Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis. United States: N. p., 2013. Web.
Schrodi, Yann. Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis. United States.
Schrodi, Yann. Tue . "Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis". United States. https://www.osti.gov/servlets/purl/1087885.
@article{osti_1087885,
title = {Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis},
author = {Schrodi, Yann},
abstractNote = {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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Jul 09 00:00:00 EDT 2013},
month = {Tue Jul 09 00:00:00 EDT 2013}
}

Works referenced in this record:

Impurity inhibition in olefin metathesis reactions
patent, May 2005


Transition metal carbene complexes containing a cationic substituent as catalysts of olefin metathesis reactions
patent-application, June 2006


Moisture resistant, repulpable paper products and method of making same
patent-application, October 2003


Triacylglycerol-based alternative to paraffin wax
patent-application, October 2002


Schiff base derivatives of ruthenium and osmium olefin metathesis catalysts
patent, November 1999


Repulpable hot melt polymer/wax compositions for fibrous products
patent, December 1997


Wax and wax-based products
patent-application, November 2004


Method for Making Industrial Chemicals
patent-application, November 2007


Telechelic alkadiene polymers with crosslinkable end groups and methods for making the same
patent, October 2002


Triacylglycerol based candle wax
patent, December 2008


Vegetable oil candle
patent, May 2004


Method of Making Hydrogenated Metathesis Products
patent-application, February 2009


Method of preparing ruthenium and osmium carbene complexes
patent, January 1998


Hydrogenated and partially hydrogenated heat-bodied oils and uses thereof
patent-application, July 2007


Synthesis of Highly Substituted Cyclopentane and Tetrahydrofuran Derivatives by Crossed Olefin Metathesis
journal, March 1996


Polymer depolymerization using ruthenium and osmium carbene complexes
patent, March 1998


Aqueous gel candle for use with a warming device
patent-application, December 2006


Integrate chemical processes for industrial utilization of seed oils
patent-application, July 2005


Synthesis of A,B-alternating copolymers by olefin metathesis reactions of cyclic olefins or olefinic polymers with an acyclic diene
patent-application, December 2003


Metathesis in Oleochemistry
journal, January 1998


Integrate chemical processes for industrial utilization of seed oils
patent, August 2009


Triacylglycerol based candle wax
patent, January 2003


Glycol Esters of Dibasic Acids. The Di-β-hydroxyethyl Esters 1
journal, January 1935


Triacylglycerol-based alternative to paraffin wax
patent-application, December 2007


Triacylglycerol based wax compositions
patent-application, March 2003


Ruthenium-catalyzed metathesis of vegetable oils
journal, January 1999


Pipe made from metathesis polymerized olefins
patent, June 2002


Metathesis Activity and Stability of New Generation Ruthenium Polymerization Catalysts
journal, November 2003


Non-paraffin candle composition
patent, May 2000


Metathesis polymerizered olefin composites including sized reinforcement material
patent, March 2000


Colorant Compositions Comprising Metathesized Unsaturated Polyol Esters
patent-application, May 2009


Lewis acid-catalyzed polymerization of biological oils and resulting polymeric materials
patent-application, July 2002


Triacylglycerol based candle wax
patent-application, November 2004


Metathesis reactions of fatty acid esters
journal, January 1985


Moisture resistant, repulpable paper products and method of making same
patent-application, June 2005


A solid-Supported phosphine-Free ruthenium alkylidene for olefin metathesis in methanol and water
journal, July 2002


Romp of functionalized cyclic olefins using ruthenium and osmium carbene complexes
patent, December 1998


Diene cyclization using ruthenium and osmium carbene complexes
patent, July 1999


Triacylglycerol based wax for use in container candles
patent-application, March 2005


Process for producing a paraffin-based object and such an object
patent, May 2001


Imidazolidine-based metal carbene metathesis catalysts
patent, February 2008


Ring-expansion of cyclic olefins metathesis reactions with an acyclic diene
patent, April 2006


Process for the synthesis of unsaturated alcohols
patent, February 2007


Vegetable oil based wax compositions
patent-application, January 2003


Candle and the method of making the same
patent, April 2001


Polyolefin compositions having variable density and methods for their production and use
patent, February 2003


Contact metathesis polymerization
patent, November 2005


Triacylglycerol based wax compositions
patent, October 2006


Catalytic Metathesis of Unsaturated Fatty Acid Esters and Oils
journal, February 2004


Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts
patent, July 2004


Latent, high-activity olefin metathesis catalysts containing an N-heterocyclic carbene ligand
patent-application, November 2005


Synthesis of macrocyclic polymers by ring insertion polymerization of cyclic olefin monomers
patent, September 2005


Stable Cyclic (Alkyl)(Amino)Carbenes as Rigid or Flexible, Bulky, Electron-Rich Ligands for Transition-Metal Catalysts: A Quaternary Carbon Atom Makes the Difference
journal, September 2005


Synthesis of Terminal Alkenes From Internal Alkenes Via Olefin Metathesis
patent-application, June 2010


Natural Fats and Oils—Renewable Raw Materials for the Chemical Industry
journal, January 1988


Ruthenium and osmium metal carbene complexes for olefin metathesis polymerization
patent, May 1994


Vegetable lipid-based composition and candle
patent-application, October 2004


Vegetable lipid-based composition and candle
patent-application, January 2007


Polymeric composites including dicyclopentadiene and related monomers
patent, October 2001


Emollient gel
patent-application, November 2003


Triacylglycerol based wax for use in container candles
patent-application, May 2004


Vegetable lipid-based composition and candle
patent-application, April 2003


Process for Co-Producing Olefins and Diesters or Diacids Starting from Unsaturated Fts
patent-application, August 2007


Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts
patent, September 2003


Metathesis
book, December 2000


Compression-molded vegetable wax-based candle
patent-application, July 2005


1,3-Diolein and 1,3-Distearin Esters of Fumaric, Succinic and Adipic Acids
journal, December 1958


Olefin Metathesis Involving Ruthenium Enoic Carbene Complexes
journal, October 2001


Group 8 transition metal carbene complexes as enantioselective olefin metathesis catalysts
patent-application, March 2003


Polyolefin compositions optionally having variable toughness and/or hardness
patent, October 2007


Model studies and the ADMET polymerization of soybean oil
journal, May 2002


Metathesis of unsaturated fatty acids: Synthesis of long-chain unsaturated-α,ω-dicarboxylic acids
journal, July 2006


High metathesis activity ruthenium and osmium metal carbene complexes
patent, November 1998


Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts
patent, November 2004


A highly efficient olefin metathesis initiator: improved synthesis and reactivity studies
journal, March 2003


Purification technique for the removal of ruthenium from olefin metathesis reaction products
journal, May 1999


Synthesis of telechelic polymers using ruthenium and osmium carbene complexes
patent, March 1999


Novel wax emulsion coating applications
patent-application, December 2006


Chelating carbene ligand precursors and their use in the synthesis of metathesis catalysts
patent, April 2006


Metathesis Methods Involving Hydrogenation and Compositions Relating to Same
patent-application, April 2010


Hot Melt Adhesive Compositions Comprising Metathesized Unsaturated Polyol Ester Wax
patent-application, February 2010


High activity ruthenium and osmium metal carbene complexes for olefin metathesis reactions
patent, October 1999


Candle refill kit and method of use
patent-application, October 2006


Colored wax articles
patent, July 2001


ABA triblock and diblock copolymers and methods of preparing the same
patent, June 2002


Metathesis syntheses of pheromones or their components
patent, February 2004


Metathesis polymerized olefin composites including sized reinforcement material
patent, November 2001


High conversion and productive catalyst turnovers in cross-metathesis reactions of natural oils with 2-butene
journal, January 2006


Synthesis of Trisubstituted Alkenes via Olefin Cross-Metathesis
journal, December 1999


Metathesis process for preparing an alpha, omega-functionalized olefin
patent, October 2010


Candle and candle wax containing metathesis and metathesis-like products
patent-application, September 2009


Triacylglycerol-based alternative to paraffin wax
patent, November 2003


Compositions Comprising Metathesized Unsaturated Polyol Esters
patent-application, September 2009


Soybean wax candles
patent, July 2003


Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins
patent-application, March 2005


Catalytic system for olefin oxidation to carbonyl products
patent, April 1996


Process for the hydrogenation of fatty acid methyl ester mixtures
patent, August 1991


Methods of Making Organic Compounds by Metathesis
patent-application, October 2009


Process for producing hydrogenated ring-opening polymerization polymer of cycloolefin
patent, November 2002


Method of removing transition metals
patent, April 2002


Triacylglycerol-based alternative to paraffin wax
patent, May 2007


Infusion of cyclic olefin resins into porous materials
patent-application, October 2003


Process for the synthesis of unsaturated alcohols
patent-application, April 2005


Drying properties of metathesized soybean oil
journal, June 1997


Vegetable fat-based candles
patent-application, March 2003


Triacylglycerol based candle wax
patent-application, June 2003


Synthesis of 5-decenyl acetate and other pheromone components
patent, April 2001


Vegetable oil candle
patent-application, May 2003


Synthesis of ruthenium or osmium metathesis catalysts
patent, June 1999


Low trans-fatty acid fat compositions; low-temperature hydrogenation, e.g., of edible oils
patent, September 2009


Triacylglycerol based wax composition
patent-application, February 2007


Methods for cross-metathesis of terminal olefins
patent, October 2001


New fat products: Glyceride esters of adipic acid
journal, December 1959


Selective ring-opening cross-metathesis of cycloolefins
patent, October 2004


Hardening of unsaturated fats, fatty acids or fatty acid esters
patent, March 1998


Functionalized polyalphaolefins
patent-application, January 2005


Vegetable oil based wax compositions
patent, November 2004


Metathesis of unsaturated fatty acid esters or unsaturated fatty acids with lower olefins
patent, October 2006


Methods of Making Organic Compounds by Metathesis and Hydrocyanation
patent-application, October 2009


Wax and wax-based products
patent, March 2007


Paint ball
patent, June 1997


Colored wax articles
patent, July 2003


Recyclable metathesis catalysts
patent, July 2005


Catalyst complex with carbene ligand
patent, November 2009


Preparation of hydrogenated product of cyclic olefin ring-opening metathesis polymer
patent, March 2001


Fluorinated polymers and methods for their preparation
patent, August 2002


Triacylglycerol-based alternative to paraffin wax
patent-application, March 2004


Low trans-fatty acid fat compositions; low-temperature hydrogenation, e.g., of edible oils
patent-application, February 2005


Impurity reduction in Olefin metathesis reactions
patent, March 2009


Compression-molded vegetable wax-based candle
patent-application, June 2007


Process for co-producing olefins and esters by ethenolysis of unsaturated fats in non-aqueous ionic liquids
patent-application, April 2006


Synthesis of functionalized and unfunctionalized olefins via cross and ring-closing metathesis
patent, September 2004


Triacylglycerol based candle wax
patent, August 2004


Triacylglycerol based wax for use in candles
patent-application, May 2004


Hydrogenation catalyst particles
patent, August 2001


The chemistry of metathesized soybean oil
journal, January 1999


Colored wax articles
patent-application, December 2001


Wax and wax-based products
patent-application, December 2006


Synthesis and Reactivity of Olefin Metathesis Catalysts Bearing Cyclic (Alkyl)(Amino)Carbenes
journal, September 2007


Functionalized polyalphaolefins
patent, January 2008