Methods of making organic compounds by metathesis

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

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.; Schrodi, Yann; Tupy, Michael John

Issue Date:: Tue Sep 01 00:00:00 EDT 2015

Research Org.:: Elevance Renewable Sciences, Inc., Woodridge, IL (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1213457

Patent Number(s):: 9120742

Application Number:: 12/422,096

Assignee:: Elevance Renewable Sciences, Inc. (Woodridge, 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

Show more

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}

Show less

DOE Contract Number:: FG36-04GO14016

Resource Type:: Patent

Resource Relation:: Patent File Date: 2009 Apr 10

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Abraham, Timothy W., Kaido, Hiroki, Lee, Choon Woo, Pederson, Richard L., Schrodi, Yann, and Tupy, Michael John. Methods of making organic compounds by metathesis.  United States: N. p., 2015. 
        Web.

Copy to clipboard


                    Abraham, Timothy W., Kaido, Hiroki, Lee, Choon Woo, Pederson, Richard L., Schrodi, Yann, & Tupy, Michael John. Methods of making organic compounds by metathesis.  United States.

Copy to clipboard


                    Abraham, Timothy W., Kaido, Hiroki, Lee, Choon Woo, Pederson, Richard L., Schrodi, Yann, and Tupy, Michael John. Tue .  
        "Methods of making organic compounds by metathesis".  United States.  https://www.osti.gov/servlets/purl/1213457.

Copy to clipboard


                    
@article{osti_1213457,

  title        = {Methods of making organic compounds by metathesis},

  author       = {Abraham, Timothy W. and Kaido, Hiroki and Lee, Choon Woo and Pederson, Richard L. and Schrodi, Yann and Tupy, Michael John},

  abstractNote = {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.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {Tue Sep 01 00:00:00 EDT 2015},

  month        = {Tue Sep 01 00:00:00 EDT 2015}

}

Copy to clipboard

Patent:

Save / Share:

Export Metadata

Save to My Library

Works referenced in this record:

Selective esterification of long chain fatty acid monoglycerides with medium chain fatty acid anhydrides
patent, August 1992

Stipp, Gordon K.; Kluesener, Bernard William
US Patent Document 5,142,072
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5142072

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

Grubbs, Robert H.; Johnson, Lynda Kaye; Nguyen, SonBinh T.
US Patent Document 5,312,940
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5312940

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

Grubbs, Robert H.; Nguyen, SonBinh T.; Johnson, Lynda Kaye
US Patent Document 5,710,298
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5710298

Romp polymerization in the presence of peroxide crosslinking agents to form high-density crosslinked polymers
patent, March 1998

Grubbs, Robert H.; Woodson, Charles S.
US Patent Document 5,728,785
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5728785

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

Grubbs, Robert H.; Nguyen, SonBinh T.
US Patent Document 5,728,917
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5728917

Olefin metathesis coupling using ruthenium and osmium carbene complexes
patent, May 1998

Grubbs, Robert H.; Nguyen, SonBinh T.
US Patent Document 5,750,815
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5750815

Synthesis of conformationally restricted amino acids, peptides, and peptidomimetics by catalytic ring closing metathesis
patent, September 1998

Grubbs, Robert H.; Miller, Scott J.; Blackwell, Helen E.
US Patent Document 5,811,515
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5811515

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

Grubbs, Robert H.; Schwab, Peter; Nguyen, SonBinh T.
US Patent Document 5,831,108
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5831108

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

Grubbs, Robert H.; Nguyen, SonBinh T.; Hillmyer, Marc A.
US Patent Document 5,849,851
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5849851

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

Grubbs, Robert H.; Nguyen, SonBinh T.; Hillmyer, Marc A.
US Patent Document 5,880,231
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5880231

Synthesis of ruthenium or osmium metathesis catalysts
patent, June 1999

Grubbs, Robert H.; Belderrain, Tomas R.; Brown, Seth N.
US Patent Document 5,917,071
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5917071

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

Grubbs, Robert H.; Nguyen, SonBinh T.; Fu, Gregory C.
US Patent Document 5,922,863
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5922863

Method for extending the pot life of an olefin metathesis polymerization reaction
patent, August 1999

Woodson, Charles S.; Grubbs, Robert H.
US Patent Document 5,939,504
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5939504

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

Grubbs, Robert H.; Nguyen, SonBinh T.; Johnson, Lynda Kaye
US Patent Document 5,969,170
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5969170

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

Grubbs, Robert H.; Chang, Sukbok; Jones, Leroy
US Patent Document 5,977,393
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/5977393

Polymerization of low grade DCPD monomers using an olefin metathesis catalyst
patent, February 2000

Woodson, Charles S.; Grubbs, Robert H.
US Patent Document 6,020,443
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6020443

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

Warner, Mark W.; Drake, Steven D.; Giardello, Michael A.
US Patent Document 6,040,363
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6040363

Template-directed ring-closing metathesis and ring-opening metathesis polymerization of functionalized dienes
patent, June 2000

Grubbs, Robert H.; Marsella, Michael J.; Maynard, Heather D.
US Patent Document 6,080,826
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6080826

Thermally initiated polymerization of olefins using Ruthenium or osmium vinylidene complexes
patent, August 2000

Grubbs, Robert H.; Wilhelm, Thomas
US Patent Document 6,107,420
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6107420

Method for producing mixtures of monoolefinic C5-mononitriles by catalytic hydrocyanation
patent, January 2001

Fischer, Jakob; Siegel, Wolfgang
US Patent Document 6,169,198
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6169198

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

Sunaga, Tadahiro; Okita, Masumi; Asanuma, Tadashi
US Patent Document 6,197,894
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6197894

Lewis acid-catalyzed polymerization of biological oils and resulting polymeric materials
patent, April 2001

Larock, Richard C.; Hanson, Mark Andrew
US Patent Document 6,211,315
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6211315

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

Pederson, Richard L.; Grubbs, Robert H.
US Patent Document 6,215,019
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6215019

Acid activation of ruthenium metathesis catalysts and living ROMP metathesis polymerization in water
patent, September 2001

Lynn, David M.; Dias, Eric L.; Grubbs, Robert H.
US Patent Document 6,284,852
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6284852

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

Grubbs, Robert H.; O'Leary, Daniel J.; Blackwell, Helen E.
US Patent Document 6,306,988
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6306988

Polymeric composites including dicyclopentadiene and related monomers
patent, October 2001

Woodson, Charles S.; Grubbs, Robert H.
US Patent Document 6,310,121
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6310121

Catalyst system comprising transition metal and imidazoline-2-ylidene or imidazolidine-2-ylidene
patent, November 2001

Nolan, Steven P.; Huang, Jinkun; Trudell, Mark L.
US Patent Document 6,316,380
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6316380

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

Warner, Mark W.; Drake, Steven D.; Giardello, Michael A.
US Patent Document 6,323,296
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6323296

Method of removing transition metals
patent, April 2002

Grubbs, Robert H.; Maynard, Heather D.; Lynn, David M.
US Patent Document 6,376,690
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6376690

Metathesis-active adhesion agents and methods for enhancing polymer adhesion to surfaces
patent, June 2002

Giardello, Michael A.; Haar, Christopher M.
US Patent Document 6,409,875
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6409875

Pipe made from metathesis polymerized olefins
patent, June 2002

Warner, Mark W.; Drake, Steven D.; Cagle, Larry
US Patent Document 6,410,110
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6410110

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

Grubbs, Robert H.; Bielawski, Christopher W.
US Patent Document 6,410,666
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6410666

Ruthenium metal alkylidene complexes coordinated with triazolylidene ligands that exhibit high olefin metathesis activity
patent, July 2002

Grubbs, Robert H.; Trinka, Tina M.
US Patent Document 6,426,419
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6426419

Fluorinated polymers and methods for their preparation
patent, August 2002

Woodson, Charles S.; Hillmyer, Marc A.; Grubbs, Robert H.
US Patent Document 6,433,101
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6433101

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

Maughon, Bob R.; Morita, Takeharu; Grubbs, Robert H.
US Patent Document 6,465,590
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6465590

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

Tsunogae, Yasuo; Sakamoto, Masato; Tokoro, Masaharu
US Patent Document 6,486,264
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6486264

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

Giardello, Michael A.; Lasch, Jonathon G.; Cruce, Christopher J.
US Patent Document 6,525,125
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6525125

Polyolefin compositions having enhanced ultraviolet and oxidative resistance and methods for their production and use
patent, June 2003

Giardello, Michael J.; Cruce, Christopher J.; Thibault, Ronald M.
US Patent Document 6,583,236
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6583236

Highly active metathesis catalysts generated in situ from inexpensive and air stable precursors
patent, August 2003

Grubbs, Robert H.; Louie, Janis; Morgan, John P.
US Patent Document 6,610,626
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6610626

One-pot synthesis of group 8 transition metal carbene complexes useful as olefin metathesis catalysts
patent, September 2003

Grubbs, Robert H.; Morgan, John P.; Benitez, Diego
US Patent Document 6,613,910
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6613910

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

Pederson, Richard L.; Woertink, Jason K.; Haar, Christopher M.
US Patent Document 6,620,955
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6620955

Metathesis syntheses of pheromones or their components
patent, February 2004

Pederson, Richard L.; Grubbs, Robert H.
US Patent Document 6,696,597
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6696597

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

Grubbs, Robert H.; Love, Jennifer; Sanford, Melanie S.
US Patent Document 6,759,537
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6759537

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

Grubbs, Robert H.; Chatterjee, Arnab K.; Morgan, John P.
US Patent Document 6,794,534
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6794534

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

Morgan, John P.; Morrill, Christie; Grubbs, Robert H.
US Patent Document 6,803,429
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6803429

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

Grubbs, Robert H.; Sanford, Melanie S.; Moore, Jason L.
US Patent Document 6,818,586
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6818586

High activity metal carbene metathesis catalysts generated using a thermally activated N-heterocyclic carbene precursor
patent, January 2005

Bell, Andrew; Grubbs, Robert H.; Morgan, John P.
US Patent Document 6,838,489
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6838489

Ring-opening metathesis polymerization of bridged bicyclic and polycyclic olefins containing two or more heteroatoms
patent, April 2005

Grubbs, Robert H.; Scherman, Oren Alexander; Kim, Hyunjin
US Patent Document 6,884,859
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6884859

Impurity inhibition in olefin metathesis reactions
patent, May 2005

Paulson, Basil P.; Pederson, Richard L.
US Patent Document 6,900,347
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6900347

Recyclable metathesis catalysts
patent, July 2005

Hoveyda, Amir H.; Kingsbury, Jason; Garber, Steven
US Patent Document 6,921,735
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6921735

Simply assembled and recyclable polymer-supported olefin metathesis catalysts
patent, July 2005

Nolan, Steven P.; Jafarpour, Laleh
US Patent Document 6,921,736
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6921736

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

Grubbs, Robert H.; Bielawski, Chris; Benitez, Diego
US Patent Document 6,946,533
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6946533

Contact metathesis polymerization
patent, November 2005

Tokas, Edward F.; Caster, Ken C.
US Patent Document 6,962,729
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6962729

Synthesis of A,B-alternating copolymers by olefin metathesis reactions of cyclic olefins or olefinic polymers with an acyclic diene
patent, January 2006

Choi, Tae Lim; Lee, Choon Woo; Rutenberg, Isaac M.
US Patent Document 6,987,154
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6987154

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

Pederson, Richard L.; Woertink, Jason K.; Haar, Christopher M.
US Patent Document 7,026,495
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7026495

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

Choi, Tae Lim; Lee, Choon Woo; Kim, Hyunjin
US Patent Document 7,034,096
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7034096

Synthesis of 1,3 distributed imidazolium salts
patent, September 2006

Nolan, Steven P.
US Patent Document 7,109,348
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7109348

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

Newman, Thomas H.; Rand, Cynthia L.; Burdett, Kenneth A.
US Patent Document 7,119,216
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7119216

Process for the synthesis of unsaturated alcohols
patent, February 2007

Maughon, Bob R.; Burdett, Kenneth A.; Lysenko, Zenon
US Patent Document 7,176,336
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7176336

Preparation of ruthenium-based olefin metathesis catalysts
patent, April 2007

Nolan, Steven P.
US Patent Document 7,205,424
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7205424

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

Giardello, Michael A.; Lasch, Jonathan G.; Cruce, Christopher J.
US Patent Document 7,285,593
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7285593

Functionalized polyalphaolefins
patent, January 2008

Nadolsky, Richard J.; Truong, David D.
US Patent Document 7,314,904
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7314904

Imidazolidine-based metal carbene metathesis catalysts
patent, February 2008

Grubbs, Robert H.; Scholl, Matthias
US Patent Document 7,329,758
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7329758

Transition metal carbene complexes containing a cationic substituent as catalysts of olefin metathesis reactions
patent, April 2008

Piers, Warren Edward; Guajardo, Patricio Eduardo Romero
US Patent Document 7,365,140
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7365140

Impurity reduction in Olefin metathesis reactions
patent, March 2009

Lee, Choon Woo; Hong, Soon Hyeok; Sanders, Daniel P.
US Patent Document 7,507,854
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7507854

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

Lysenko, Zenon; Maughon, Bob R.; Bicerano, Josef
US Patent Document 7,576,227
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7576227

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

van Toor, Hans; Van Rossum, Gijsbertus; Kruidenberg, Marco
US Patent Document 7,585,990
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7585990

Cross-metathesis of olefins directly substituted with an electron-withdrawing group using transition metal carbene catalysts
patent, October 2009

Grubbs, Robert H.; Morgan, John P.; Love, Jennifer
US Patent Document 7,598,330
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7598330

Catalyst complex with carbene ligand
patent, November 2009

Nolan, Steven P.; Huang, Jinkun
US Patent Document 7,622,590
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7622590

Process for co-producing olefins and esters by ethenolysis of unsaturated fats in non-aqueous ionic liquids
patent, March 2010

Thurier, Cyril; Olivier-Bourbigou, Helene; Dixneuf, Pierre
US Patent Document 7,678,932
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7678932

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

Burdett, Kenneth A.; Mokhtarzadeh, Morteza; Timmers, Francis J.
US Patent Document 7,812,185
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7812185

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

Larock, Richard C.; Hanson, Mark; Li, Fengkui
US Patent Application 09/969874; 20020095007
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20020095007

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

Grubbs, Robert H.; Ward, Donald W.; Seiders, Thomas J.
US Patent Application 10/124745; 20030055262
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20030055262

Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts
patent-application, May 2003

Grubbs, Robert H.; Chatterjee, Arnab K.; Choi, Tae-Lim
US Patent Application 10/114418; 20030100776
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20030100776

Catalytic osmium-assisted oxidative cleavage of olefins
patent-application, August 2003

Borhan, Babak; Travis, Benjamin R.; Schomaker, Jennifer M.
US Patent Application 10/341499; 20030149299
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20030149299

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

Cruce, Christopher J.; Filice, Gary W.; Giardello, Michael A.
US Patent Application 10/233066; 20030186035
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20030186035

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

Newman, Thomas H.; Rand, Cynthia L.; Burdett, Kenneth A.
US Patent Application 10/469321; 20050070750
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20050070750

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

Ung, Thay; Schrodi, Yann; Trimmer, Mark S.
US Patent Application 11/094102; 20050261451
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20050261451

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

Lacombe, Sylvie; Revel, Renaud; Briot, Patrick
US Patent Application 11/286351; 20060079704
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060079704

Novel wax emulsion coating applications
patent-application, December 2006

Borsinger, Gregory G.; Hassan, Abbas
US Patent Application 10/388548; 20060289138
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060289138

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

Olivier-Bourbigou, Helene; Vallee, Christophe; Hillion, Gerard
US Patent Application 11/626077; 20070179307
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070179307

Method for Making Industrial Chemicals
patent-application, November 2007

Millis, James R.; Tupy, Michael J.; Abrahan, Timothy W.
US Patent Application 10/542167; 20070270621
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070270621

Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis
patent-application, January 2008

Schrodi, Yann
US Patent Application 11/879029; 20080027194
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20080027194

Ring opening cross-metathesis reaction of cyclic olefins with seed oils and the like
patent-application, March 2008

Lee, Choon Woo
US Patent Application 11/827937; 20080064891
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20080064891

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

Tupy, Michael John; Amore, Francis; Kaido, Hiroki
US Patent Application 12/170818; 20090048459
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20090048459

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

Murphy, Timothy A.; Auidembrink, Brent A.
US Patent Application 12/281931; 20090126602
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20090126602

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

Murphy, Timothy A.; Tupy, Michael J.; Abraham, Timothy W.
US Patent Application 11/795052; 20090217568
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20090217568

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

Braksmayer, Dizza Pearl; Murphy, Timothy A.; Russell, Stephen E.
US Patent Application 12/281938; 20090220443
URL: https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20090220443