WO1999062894A3 - Process for epoxidation of aryl allyl ethers - Google Patents

Process for epoxidation of aryl allyl ethers

Info

Publication number
WO1999062894A3
WO1999062894A3 PCT/US1999/011427 US9911427W WO9962894A3 WO 1999062894 A3 WO1999062894 A3 WO 1999062894A3 US 9911427 W US9911427 W US 9911427W WO 9962894 A3 WO9962894 A3 WO 9962894A3
Authority
WO
WIPO (PCT)
Prior art keywords
percent
transition metal
allyl ethers
epoxidation
complex catalyst
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/US1999/011427
Other languages
French (fr)
Other versions
WO1999062894A2 (en
Inventor
Zeng K Liao
Clint J Boriack
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.)
Dow Chemical Co
Original Assignee
Dow Chemical Co
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 Chemical Co filed Critical Dow Chemical Co
Priority to EP99924475A priority Critical patent/EP1080084B1/en
Priority to DE69917018T priority patent/DE69917018T2/en
Priority to BR9911208-6A priority patent/BR9911208A/en
Priority to KR1020007013419A priority patent/KR20010043904A/en
Priority to JP2000552106A priority patent/JP2002517387A/en
Priority to AU40963/99A priority patent/AU4096399A/en
Publication of WO1999062894A2 publication Critical patent/WO1999062894A2/en
Publication of WO1999062894A3 publication Critical patent/WO1999062894A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/19—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic hydroperoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Epoxy Compounds (AREA)
  • Epoxy Resins (AREA)

Abstract

A process for making an aromatic glycidyl ether epoxy compound by contacting an allyl ether made from the hydroxy moiety of a hydroxy-containing aromatic compound with an inorganic or organic hydroperoxide oxidant in the presence of a transition metal complex catalyst, wherein at least (a) the allyl ether is conformationally restricted or (b) the transition metal complex catalyst contains at least one or more stable ligands attached to the transition metal. The process of the present invention provides for epoxidizing aryl allyl ethers with high epoxidation yield (for example, greater than 70 percent to 90 percent) and high hydroperoxide selectivity (for example, greater than 70 percent to 90 percent).
PCT/US1999/011427 1998-05-29 1999-05-24 Process for epoxidation of aryl allyl ethers Ceased WO1999062894A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP99924475A EP1080084B1 (en) 1998-05-29 1999-05-24 Process for epoxidation of aryl allyl ethers
DE69917018T DE69917018T2 (en) 1998-05-29 1999-05-24 PROCESS FOR EPOXIDATING ARYL ALLYL ETHERS
BR9911208-6A BR9911208A (en) 1998-05-29 1999-05-24 Epoxidation process for aryl allyl ethers.
KR1020007013419A KR20010043904A (en) 1998-05-29 1999-05-24 Epoxidation process for aryl allyl ethers
JP2000552106A JP2002517387A (en) 1998-05-29 1999-05-24 Epoxidation of aryl allyl ethers
AU40963/99A AU4096399A (en) 1998-05-29 1999-05-24 Epoxidation process for aryl allyl ethers

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US8716998P 1998-05-29 1998-05-29
US60/087,169 1998-05-29

Publications (2)

Publication Number Publication Date
WO1999062894A2 WO1999062894A2 (en) 1999-12-09
WO1999062894A3 true WO1999062894A3 (en) 2000-04-06

Family

ID=22203520

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/011427 Ceased WO1999062894A2 (en) 1998-05-29 1999-05-24 Process for epoxidation of aryl allyl ethers

Country Status (9)

Country Link
EP (1) EP1080084B1 (en)
JP (1) JP2002517387A (en)
KR (1) KR20010043904A (en)
CN (1) CN1303382A (en)
AU (1) AU4096399A (en)
BR (1) BR9911208A (en)
DE (1) DE69917018T2 (en)
TW (1) TW448164B (en)
WO (1) WO1999062894A2 (en)

Families Citing this family (42)

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Publication number Priority date Publication date Assignee Title
US6534621B2 (en) 2000-05-18 2003-03-18 Dow Global Technologies Inc. Process for manufacturing a hydroxyester derivative intermediate and epoxy resins prepared therefrom
KR100342659B1 (en) * 2000-12-15 2002-07-04 Rstech Co Ltd Chiral polymer salene catalyst and process for preparing chiral compounds from racemic epoxide using the same
EP1398080A1 (en) * 2002-07-18 2004-03-17 Nippon Shokubai Co., Ltd. Liquid phase oxygenation reaction using tungsten species
JP3669360B2 (en) * 2002-11-29 2005-07-06 昭和高分子株式会社 Epoxyfluorene compound and method for producing the same
US7030255B2 (en) * 2004-03-09 2006-04-18 Lyondell Chemical Technology, L.P. Oxidation process with in-situ H202 generation and polymer-encapsulated catalysts therefor
ATE483444T1 (en) * 2004-07-14 2010-10-15 3M Espe Ag DENTAL COMPOSITION WITH EPOXY FUNCTIONAL POLYMERIZABLE COMPOUNDS
ATE424179T1 (en) 2004-07-14 2009-03-15 3M Espe Ag DENTAL COMPOSITION CONTAINING UNSATURATED HALOGENATED ARYLAKYL ETHER INGREDIENTS
WO2006132139A1 (en) * 2005-06-06 2006-12-14 Mitsubishi Gas Chemical Company, Inc. Compound for resist and resist composition
JP2007197518A (en) * 2006-01-24 2007-08-09 Fujifilm Corp Epoxy resin compound, thermosetting resin composition, and photosensitive composition
CN101384574B (en) * 2006-02-17 2011-11-09 出光兴产株式会社 Adamantane derivative, composition containing the same, and optical electronic component using the composition
JPWO2011019061A1 (en) * 2009-08-13 2013-01-17 昭和電工株式会社 Method for producing polyglycidyl ether compound
WO2011078060A1 (en) * 2009-12-24 2011-06-30 昭和電工株式会社 Process for production of glycidyl ether compounds, and monoallyl monoglycidyl ether compound
WO2011078091A1 (en) * 2009-12-24 2011-06-30 昭和電工株式会社 Process for production of epoxy compound
EP2357180A1 (en) * 2010-02-02 2011-08-17 Momentive Specialty Chemicals Research Belgium S.A. Manufacture of epoxyethyl ethers or glycidyl ethers
TWI426090B (en) * 2011-05-31 2014-02-11 Tsrc Corp Method for producing epoxidized polymer
KR101252063B1 (en) * 2011-08-25 2013-04-12 한국생산기술연구원 Epoxy Compound Having Alkoxysilyl Group, Preparing Method Thereof, Composition Comprising the Same and Cured Product and Use Thereof
CN103906753B (en) 2011-11-01 2017-02-15 韩国生产技术研究院 Isocyanurate epoxy compound containing alkoxysilyl group, its preparation method, composition including it, cured product of composition and application of composition
WO2013137663A1 (en) 2012-03-14 2013-09-19 한국생산기술연구원 Epoxy compound having alkoxy silyl group, composition comprising same, cured product, use thereof and method for preparing epoxy compound having alkoxy silyl group
WO2013151308A1 (en) 2012-04-02 2013-10-10 한국생산기술연구원 Epoxy compound having alkoxysilyl group, composition and hardened material comprising same, use for same, and production method for epoxy compound having alkoxysilyl group
KR101863111B1 (en) 2012-07-06 2018-06-01 한국생산기술연구원 Novolac-based epoxy compound, preparing method thereof, composition, cured product thereof, and use thereof
US9127127B2 (en) 2012-10-03 2015-09-08 Sabic Global Technologies B.V. Polyetherimide compositions, methods of manufacture, and articles formed therefrom
JPWO2014123051A1 (en) * 2013-02-05 2017-02-02 日本化薬株式会社 Allyl ether resin and epoxy resin
EP2978831B1 (en) 2013-03-28 2020-12-02 The Procter and Gamble Company Cleaning compositions containing a polyetheramine, a soil release polymer, and a carboxymethylcellulose
US10676571B2 (en) 2013-12-02 2020-06-09 Sabic Global Technologies B.V. Polyetherimides with improved melt stability
WO2015148360A1 (en) 2014-03-27 2015-10-01 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
WO2015148361A1 (en) 2014-03-27 2015-10-01 The Procter & Gamble Company Cleaning compositions containing a polyetheramine
WO2015187757A1 (en) 2014-06-06 2015-12-10 The Procter & Gamble Company Detergent composition comprising polyalkyleneimine polymers
WO2016032993A1 (en) 2014-08-27 2016-03-03 The Procter & Gamble Company Detergent composition comprising a cationic polymer
US9809782B2 (en) 2014-08-27 2017-11-07 The Procter & Gamble Company Detergent composition comprising a cationic polymer and anionic/nonionic surfactant mixture
EP3186349B1 (en) 2014-08-27 2019-09-25 The Procter and Gamble Company Detergent composition comprising a cationic polymer
WO2016032995A1 (en) 2014-08-27 2016-03-03 The Procter & Gamble Company Method of treating a fabric
US9850452B2 (en) 2014-09-25 2017-12-26 The Procter & Gamble Company Fabric care compositions containing a polyetheramine
FR3030514A1 (en) * 2014-12-18 2016-06-24 Centre De Coop Int En Rech Agronomique Pour Le Dev (Cirad) POLYAROMATIC DIMERS
CN104557532B (en) * 2015-01-13 2017-03-01 西安力邦制药有限公司 Bigeminy benzene derivative and its application
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CN109985659B (en) * 2019-04-22 2022-03-01 南京工程学院 A kind of catalyst for preparing aromatic hydrocarbons by directional conversion of CO2 and preparation method thereof
KR102232340B1 (en) 2019-11-15 2021-03-26 한국생산기술연구원 Composition of alkoxysilyl-functionalized epoxy resin and composite thereof
CN112920223B (en) * 2021-02-08 2022-09-20 兰州大学 A kind of catalyst and preparation method for the siliconitrile reaction of aldehyde and trimethyl cyanosilane
CA3228918A1 (en) 2021-08-10 2023-02-16 Nippon Shokubai Co., Ltd. Polyalkylene-oxide-containing compound
CN114920652B (en) * 2022-05-30 2024-04-19 宁波工程学院 Method for photocatalytic synthesis of 1-alkylstyrene derivatives
CN115960335B (en) * 2022-12-21 2025-08-26 江苏兴盛化工有限公司 A kind of ultra-high molecular weight methyl bromide epoxy resin and its preparation method and application
CN117160141B (en) * 2023-07-27 2026-04-21 安徽省太和县众友筛网滤布制造有限公司 A special filter cloth for leaching and purification in hydrometallurgical processes

Citations (10)

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Publication number Priority date Publication date Assignee Title
JPS59227872A (en) * 1983-06-08 1984-12-21 Sumitomo Chem Co Ltd Preparation of epoxy compound
US4507492A (en) * 1983-05-06 1985-03-26 The Dow Chemical Company Preparation of aromatic derivatives
JPS6056975A (en) * 1983-09-07 1985-04-02 Sumitomo Chem Co Ltd Production of glydicyl ether
EP0166527A2 (en) * 1984-05-28 1986-01-02 Nippon Mining Company Limited A process for the preparation of epoxides by means of microorganisms
US4740330A (en) * 1986-09-03 1988-04-26 The Dow Chemical Company Method for allylating aromatic hydroxyl-containing compounds
US5118822A (en) * 1991-09-30 1992-06-02 Arco Chemical Technology, L.P. Olefin epoxidation using a perrhenate catalyst and an organic hydroperoxide
US5319114A (en) * 1993-09-23 1994-06-07 Arco Chemical Technology, L. P. Olefin epoxidation using a carbon molecular sieve impregnated with a transition metal
US5578740A (en) * 1994-12-23 1996-11-26 The Dow Chemical Company Process for preparation of epoxy compounds essentially free of organic halides
US5633391A (en) * 1996-04-12 1997-05-27 National Starch And Chemical Investment Holding Corporation Methyltrioxorhenium-bis(trimethylsilyl)peroxide epoxidation of olefins
GB2309655A (en) * 1996-02-03 1997-08-06 Univ Delft Tech Heterogeneous Catalysts

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4507492A (en) * 1983-05-06 1985-03-26 The Dow Chemical Company Preparation of aromatic derivatives
JPS59227872A (en) * 1983-06-08 1984-12-21 Sumitomo Chem Co Ltd Preparation of epoxy compound
JPS6056975A (en) * 1983-09-07 1985-04-02 Sumitomo Chem Co Ltd Production of glydicyl ether
EP0166527A2 (en) * 1984-05-28 1986-01-02 Nippon Mining Company Limited A process for the preparation of epoxides by means of microorganisms
US4740330A (en) * 1986-09-03 1988-04-26 The Dow Chemical Company Method for allylating aromatic hydroxyl-containing compounds
US5118822A (en) * 1991-09-30 1992-06-02 Arco Chemical Technology, L.P. Olefin epoxidation using a perrhenate catalyst and an organic hydroperoxide
US5319114A (en) * 1993-09-23 1994-06-07 Arco Chemical Technology, L. P. Olefin epoxidation using a carbon molecular sieve impregnated with a transition metal
US5578740A (en) * 1994-12-23 1996-11-26 The Dow Chemical Company Process for preparation of epoxy compounds essentially free of organic halides
GB2309655A (en) * 1996-02-03 1997-08-06 Univ Delft Tech Heterogeneous Catalysts
US5633391A (en) * 1996-04-12 1997-05-27 National Starch And Chemical Investment Holding Corporation Methyltrioxorhenium-bis(trimethylsilyl)peroxide epoxidation of olefins

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PATENT ABSTRACTS OF JAPAN vol. 9, no. 96 (C - 278) 25 April 1985 (1985-04-25) *

Also Published As

Publication number Publication date
KR20010043904A (en) 2001-05-25
BR9911208A (en) 2001-02-13
JP2002517387A (en) 2002-06-18
TW448164B (en) 2001-08-01
DE69917018D1 (en) 2004-06-09
CN1303382A (en) 2001-07-11
DE69917018T2 (en) 2005-03-24
WO1999062894A2 (en) 1999-12-09
AU4096399A (en) 1999-12-20
EP1080084A2 (en) 2001-03-07
EP1080084B1 (en) 2004-05-06

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