WO2005040077A3 - An improved process for the synthesis of unsaturated alcohols - Google Patents

An improved process for the synthesis of unsaturated alcohols Download PDF

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Publication number
WO2005040077A3
WO2005040077A3 PCT/US2004/030020 US2004030020W WO2005040077A3 WO 2005040077 A3 WO2005040077 A3 WO 2005040077A3 US 2004030020 W US2004030020 W US 2004030020W WO 2005040077 A3 WO2005040077 A3 WO 2005040077A3
Authority
WO
WIPO (PCT)
Prior art keywords
homo
fatty acid
hydroxy
alcohol
unsaturated
Prior art date
Application number
PCT/US2004/030020
Other languages
French (fr)
Other versions
WO2005040077A2 (en
Inventor
Bob R Maughon
Kenneth A Burdett
Zenon Lysenko
Original Assignee
Dow Global Technologies Inc
Bob R Maughon
Kenneth A Burdett
Zenon Lysenko
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 Dow Global Technologies Inc, Bob R Maughon, Kenneth A Burdett, Zenon Lysenko filed Critical Dow Global Technologies Inc
Priority to CA002541263A priority Critical patent/CA2541263A1/en
Priority to JP2006533917A priority patent/JP4779121B2/en
Priority to DE602004014958T priority patent/DE602004014958D1/en
Priority to EP04788745A priority patent/EP1673328B1/en
Priority to BRPI0415176-3A priority patent/BRPI0415176B1/en
Publication of WO2005040077A2 publication Critical patent/WO2005040077A2/en
Publication of WO2005040077A3 publication Critical patent/WO2005040077A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

A process of preparing an unsaturated alcohol (olefin alcohol), such as, a homo-allylic mono-alcohol or homo-allylic polyol, involving protecting a hydroxy-substituted unsaturated fatty acid or fatty acid ester, such as methyl ricinoleate, derived from a seed oil, to form a hydroxy-protected unsaturated fatty acid or fatty acid ester; homo-metathesizing or cross-metathesizing the hydroxy-protected unsaturated fatty acid or fatty acid ester to produce a product mixture containing a hydroxy-protected unsaturated metathesis product; and deprotecting the hydroxy-protected unsaturated metathesis product under conditions sufficient to prepare the unsaturated alcohol. Preferably, methyl ricinoleate is converted by cross-metathesis or homo-metathesis into the homo-allylic mono-alcohol 1-decene-4-ol or the homo-allylic polyol 9-octadecene-7,12-diol, respectively.
PCT/US2004/030020 2003-10-09 2004-09-14 An improved process for the synthesis of unsaturated alcohols WO2005040077A2 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CA002541263A CA2541263A1 (en) 2003-10-09 2004-09-14 An improved process for the synthesis of unsaturated alcohols
JP2006533917A JP4779121B2 (en) 2003-10-09 2004-09-14 Improved synthesis of unsaturated alcohols.
DE602004014958T DE602004014958D1 (en) 2003-10-09 2004-09-14 IMPROVED METHOD FOR SYNTHESIS OF UNSATURATED ALCOHOLS
EP04788745A EP1673328B1 (en) 2003-10-09 2004-09-14 An improved process for the synthesis of unsaturated alcohols
BRPI0415176-3A BRPI0415176B1 (en) 2003-10-09 2004-09-14 Process of preparation of an unsaturated alcohol and composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US50990803P 2003-10-09 2003-10-09
US60/509,908 2003-10-09

Publications (2)

Publication Number Publication Date
WO2005040077A2 WO2005040077A2 (en) 2005-05-06
WO2005040077A3 true WO2005040077A3 (en) 2005-08-04

Family

ID=34520015

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2004/030020 WO2005040077A2 (en) 2003-10-09 2004-09-14 An improved process for the synthesis of unsaturated alcohols

Country Status (10)

Country Link
US (1) US7176336B2 (en)
EP (1) EP1673328B1 (en)
JP (1) JP4779121B2 (en)
CN (1) CN100588638C (en)
AR (1) AR046097A1 (en)
AT (1) ATE400542T1 (en)
BR (1) BRPI0415176B1 (en)
CA (1) CA2541263A1 (en)
DE (1) DE602004014958D1 (en)
WO (1) WO2005040077A2 (en)

Cited By (2)

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US8436110B2 (en) 2008-10-31 2013-05-07 Dow Global Technologies Llc Olefin metathesis process employing bimetallic ruthenium complex with bridging hydrido ligands
CN104447162A (en) * 2013-09-24 2015-03-25 中国石油化工股份有限公司 Method for preparing dodecylene

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MX2007008359A (en) 2005-01-10 2007-09-06 Cargill Inc Candle and candle wax containing metathesis and metathesis-like products.
EP1896385B1 (en) * 2005-06-06 2013-08-28 Dow Global Technologies LLC Metathesis process for preparing an alpha, omega -functionalized olefin
WO2007081987A2 (en) 2006-01-10 2007-07-19 Elevance Renewable Sciences, Inc. Method of making hydrogenated metathesis products
WO2007103460A2 (en) * 2006-03-07 2007-09-13 Elevance Renewable Sciences, Inc. Colorant compositions comprising metathesized unsaturated polyol esters
KR101660420B1 (en) * 2006-03-07 2016-09-27 엘레반스 리뉴어블 사이언시즈, 인코포레이티드 Compositions comprising metathesized unsaturated polyol esters
CN101563315B (en) * 2006-07-12 2013-08-14 埃莱文斯可更新科学公司 Ring opening cross-metathesis reaction of cyclic olefins with seed oils and the like
EP2046908B1 (en) * 2006-07-12 2017-01-11 Elevance Renewable Sciences, Inc. Hot melt adhesive compositions comprising metathesized unsaturated polyol ester wax
WO2008010961A2 (en) 2006-07-13 2008-01-24 Elevance Renewable Sciences, Inc. Synthesis of terminal alkenes from internal alkenes and ethylene via olefin metathesis
WO2008048520A2 (en) * 2006-10-13 2008-04-24 Elevance Renewable Sciences, Inc. Methods of making organic compounds by metathesis and hydrocyanation
WO2008063322A2 (en) * 2006-10-13 2008-05-29 Elevance Renewable Sciences, Inc. Metathesis methods involving hydrogenation and compositions relating to same
WO2008048522A1 (en) * 2006-10-13 2008-04-24 Elevance Renewable Sciences, Inc. Methods of making monounsaturated functionalized alkene compounds by metathesis
EP3281931A1 (en) 2006-10-13 2018-02-14 Elevance Renewable Sciences, Inc. Methods of making organic compounds by metathesis
CN106083579A (en) * 2006-10-13 2016-11-09 埃莱文斯可更新科学公司 By olefin metathesis by the method for internal olefin synthesis terminal olefin
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WO2010062958A1 (en) * 2008-11-26 2010-06-03 Elevance Renewable Sciences, Inc. Methods of producing jet fuel from natural oil feedstocks through metathesis reactions
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US9222056B2 (en) 2009-10-12 2015-12-29 Elevance Renewable Sciences, Inc. Methods of refining natural oils, and methods of producing fuel compositions
US9169447B2 (en) 2009-10-12 2015-10-27 Elevance Renewable Sciences, Inc. Methods of refining natural oils, and methods of producing fuel compositions
US9365487B2 (en) 2009-10-12 2016-06-14 Elevance Renewable Sciences, Inc. Methods of refining and producing dibasic esters and acids from natural oil feedstocks
US9000246B2 (en) 2009-10-12 2015-04-07 Elevance Renewable Sciences, Inc. Methods of refining and producing dibasic esters and acids from natural oil feedstocks
US8735640B2 (en) 2009-10-12 2014-05-27 Elevance Renewable Sciences, Inc. Methods of refining and producing fuel and specialty chemicals from natural oil feedstocks
US9175231B2 (en) 2009-10-12 2015-11-03 Elevance Renewable Sciences, Inc. Methods of refining natural oils and methods of producing fuel compositions
CN104479882A (en) 2009-10-12 2015-04-01 艾勒旺斯可再生科学公司 Methods of refining and producing fuel from natural oil feedstocks
US9382502B2 (en) 2009-10-12 2016-07-05 Elevance Renewable Sciences, Inc. Methods of refining and producing isomerized fatty acid esters and fatty acids from natural oil feedstocks
JP6117211B2 (en) 2011-09-20 2017-04-19 ダウ コーニング コーポレーションＤｏｗ Ｃｏｒｎｉｎｇ Ｃｏｒｐｏｒａｔｉｏｎ Ruthenium-containing hydrosilylation catalyst and composition containing the catalyst
US9169174B2 (en) 2011-12-22 2015-10-27 Elevance Renewable Sciences, Inc. Methods for suppressing isomerization of olefin metathesis products
US9139493B2 (en) 2011-12-22 2015-09-22 Elevance Renewable Sciences, Inc. Methods for suppressing isomerization of olefin metathesis products
US9133416B2 (en) 2011-12-22 2015-09-15 Elevance Renewable Sciences, Inc. Methods for suppressing isomerization of olefin metathesis products
IN2014DN05640A (en) 2012-01-10 2015-04-03 Elevance Renewable Sciences
AU2013277107B2 (en) 2012-06-20 2018-03-08 Wilmar Trading Pte Ltd Natural oil metathesis compositions
US9458298B2 (en) 2012-10-01 2016-10-04 Georgia-Pacific Chemicals Llc Methods for making lignocellulose containing composite products
US9586338B2 (en) 2012-10-01 2017-03-07 Georgia-Pacific Chemicals Llc Methods for making lignocellulose containing composite products
US9388098B2 (en) 2012-10-09 2016-07-12 Elevance Renewable Sciences, Inc. Methods of making high-weight esters, acids, and derivatives thereof
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CN104058919B (en) * 2013-03-20 2016-03-30 中国石油化工股份有限公司 A kind of method preparing 1-heptene
WO2015153519A1 (en) 2014-04-02 2015-10-08 Georgia-Pacific Chemicals Llc Methods for making lignocellulose composite products with oxidative binders and complexed metal catalyst
WO2015153520A1 (en) 2014-04-02 2015-10-08 Georgia-Pacific Chemicals Llc Methods for making lignocellulose composite products with oxidative binders and encapsulated catalyst
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8436110B2 (en) 2008-10-31 2013-05-07 Dow Global Technologies Llc Olefin metathesis process employing bimetallic ruthenium complex with bridging hydrido ligands
CN104447162A (en) * 2013-09-24 2015-03-25 中国石油化工股份有限公司 Method for preparing dodecylene
CN104447162B (en) * 2013-09-24 2016-05-25 中国石油化工股份有限公司 A kind of preparation method of dodecylene

Also Published As

Publication number Publication date
DE602004014958D1 (en) 2008-08-21
JP4779121B2 (en) 2011-09-28
BRPI0415176B1 (en) 2014-04-15
CA2541263A1 (en) 2005-05-06
AR046097A1 (en) 2005-11-23
EP1673328B1 (en) 2008-07-09
EP1673328A2 (en) 2006-06-28
ATE400542T1 (en) 2008-07-15
BRPI0415176A (en) 2006-11-28
US7176336B2 (en) 2007-02-13
CN1863754A (en) 2006-11-15
CN100588638C (en) 2010-02-10
US20050080301A1 (en) 2005-04-14
WO2005040077A2 (en) 2005-05-06
JP2007508300A (en) 2007-04-05

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