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WO2008060383A3 - Methods of making organic acid and organic aldehyde compounds by metathesis - Google Patents

Methods of making organic acid and organic aldehyde compounds by metathesis Download PDF

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Publication number
WO2008060383A3
WO2008060383A3 PCT/US2007/021935 US2007021935W WO2008060383A3 WO 2008060383 A3 WO2008060383 A3 WO 2008060383A3 US 2007021935 W US2007021935 W US 2007021935W WO 2008060383 A3 WO2008060383 A3 WO 2008060383A3
Authority
WO
WIPO (PCT)
Prior art keywords
methods
metathesis
organic acid
organic
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2007/021935
Other languages
French (fr)
Other versions
WO2008060383A2 (en
Inventor
Timothy W. Abraham
Hiroki Kaido
Choon Woo Lee
Richard L. Pederson
Yann Schrodi
Michael John Tupy
Kevin D. Uptain
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Materia Inc
Elevance Renewable Sciences Inc
Original Assignee
Materia Inc
Elevance Renewable Sciences Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Materia Inc, Elevance Renewable Sciences Inc filed Critical Materia Inc
Publication of WO2008060383A2 publication Critical patent/WO2008060383A2/en
Anticipated expiration legal-status Critical
Publication of WO2008060383A3 publication Critical patent/WO2008060383A3/en
Ceased legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/34Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with ozone; by hydrolysis of ozonides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention is directed to methods of making organic compounds (e.g., organic acid or aldehyde compounds) by metathesis followed by oxidation and either oxidative or reductive cleavage. The methods may be used to make certain industrially important organic acid compounds, for example, azelaic acid. The methods of the invention make use of a cross-metathesis step with a short-chain olefin to chemically modify the starting composition in order to produce a functionalized alkene intermediate that has a pre-determined carbon-carbon double bond position. Upon separation of the functionalized alkene intermediate from the other cross-metathesis products, it is oxidized and then may be oxidatively cleaved to form an organic acid or reductively cleaved to form an aldehyde.
PCT/US2007/021935 2006-10-13 2007-10-15 Methods of making organic acid and organic aldehyde compounds by metathesis Ceased WO2008060383A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US85136406P 2006-10-13 2006-10-13
US60/851,364 2006-10-13

Publications (2)

Publication Number Publication Date
WO2008060383A2 WO2008060383A2 (en) 2008-05-22
WO2008060383A3 true WO2008060383A3 (en) 2011-07-21

Family

ID=39402177

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/021935 Ceased WO2008060383A2 (en) 2006-10-13 2007-10-15 Methods of making organic acid and organic aldehyde compounds by metathesis

Country Status (1)

Country Link
WO (1) WO2008060383A2 (en)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030149299A1 (en) * 2002-01-15 2003-08-07 Board Of Trustees Of Michigan State University Catalytic osmium-assisted oxidative cleavage of olefins

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030149299A1 (en) * 2002-01-15 2003-08-07 Board Of Trustees Of Michigan State University Catalytic osmium-assisted oxidative cleavage of olefins

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
MOL J.C.: "Catalytic Metathesis of Unsaturated Fatty Acid Esters and Oils", TOPICS IN CATAL., vol. 27, no. 1-4, February 2004 (2004-02-01), pages 97 - 104, XP002481667, DOI: doi:10.1023/B:TOCA.0000013544.89226.c4 *
PATEL J. ET AL: "Cross-metathesis of Unsaturated Natural Oils with 2-Butene . High Conversion and Productive Catalyst Turnovers", CHEM. COMMUN., 5 October 2005 (2005-10-05), pages 5546 - 5547 *
WARWEL S. ET AL: "Synthesis of Dicarboxylic Acids by Transition-metal Catal yzed Oxidative Cleavage of Terminal Unsaturated Fatty Acids", TOPICS IN CURR. CHEM., vol. 164, 1993, pages 79 - 98 *

Also Published As

Publication number Publication date
WO2008060383A2 (en) 2008-05-22

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