WO2005014568A3 - Production of dialkylated hydroquinones - Google Patents

Production of dialkylated hydroquinones Download PDF

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Publication number
WO2005014568A3
WO2005014568A3 PCT/GB2004/003390 GB2004003390W WO2005014568A3 WO 2005014568 A3 WO2005014568 A3 WO 2005014568A3 GB 2004003390 W GB2004003390 W GB 2004003390W WO 2005014568 A3 WO2005014568 A3 WO 2005014568A3
Authority
WO
WIPO (PCT)
Prior art keywords
catalyst
production
sulphonic acid
olefin
hydroquinone
Prior art date
Application number
PCT/GB2004/003390
Other languages
French (fr)
Other versions
WO2005014568A2 (en
Inventor
Rainer Filipp
Gerhard Lehmann
Thomas Helmut Mrozek
Original Assignee
Great Lakes Chemical Europ
Rainer Filipp
Gerhard Lehmann
Thomas Helmut Mrozek
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 Great Lakes Chemical Europ, Rainer Filipp, Gerhard Lehmann, Thomas Helmut Mrozek filed Critical Great Lakes Chemical Europ
Priority to JP2006522407A priority Critical patent/JP4801586B2/en
Priority to MXPA06001390A priority patent/MXPA06001390A/en
Priority to DE112004001345T priority patent/DE112004001345T5/en
Publication of WO2005014568A2 publication Critical patent/WO2005014568A2/en
Publication of WO2005014568A3 publication Critical patent/WO2005014568A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
    • C07C37/16—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom

Abstract

A process for the production of a disubstituted hydroquinone which comprises alkylating hydroquinone in the presence of a sulphonic acid condensation catalyst with an olefin or a substance which under the reaction conditions acts as a source thereof. The preferred olefin is 2-methyl-2-butene either alone or in admixture- with isomers thereof, and the preferred catalyst is methane sulphonic acid and the reaction product is 2,5-di-tert-amylhydroquinone. Only catalytic amounts of catalyst are required. The reaction product is worked-up by complete dissolution of the desired product and washing with an aqueous medium containing a pH buffering agent and a reducing agent.
PCT/GB2004/003390 2003-08-04 2004-08-04 Production of dialkylated hydroquinones WO2005014568A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2006522407A JP4801586B2 (en) 2003-08-04 2004-08-04 Production of disubstituted hydroquinones
MXPA06001390A MXPA06001390A (en) 2003-08-04 2004-08-04 Production of dialkylated hydroquinones.
DE112004001345T DE112004001345T5 (en) 2003-08-04 2004-08-04 Preparation of dialkylated hydroquinones

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0318209.4 2003-08-04
GB0318209A GB0318209D0 (en) 2003-08-04 2003-08-04 Production of disubstituted hydroquinones

Publications (2)

Publication Number Publication Date
WO2005014568A2 WO2005014568A2 (en) 2005-02-17
WO2005014568A3 true WO2005014568A3 (en) 2005-03-31

Family

ID=27799751

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2004/003390 WO2005014568A2 (en) 2003-08-04 2004-08-04 Production of dialkylated hydroquinones

Country Status (5)

Country Link
JP (1) JP4801586B2 (en)
DE (1) DE112004001345T5 (en)
GB (1) GB0318209D0 (en)
MX (1) MXPA06001390A (en)
WO (1) WO2005014568A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6630153B2 (en) * 2001-02-23 2003-10-07 Smith & Nephew, Inc. Manufacture of bone graft substitutes
CN115073352A (en) * 2022-06-28 2022-09-20 吉尔多肽生物制药(大连市)有限公司 Synthetic method of 2,5, 7-tri-tert-butyl tryptophan

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2722556A (en) * 1952-03-19 1955-11-01 Eastman Kodak Co Preparation of tertiary butyl hydroquinone
WO1987005290A1 (en) * 1986-03-06 1987-09-11 Owens-Corning Fiberglas Corporation Process for the preparation of styrenated hydroquinone
EP0347835A2 (en) * 1988-06-21 1989-12-27 HIMONT ITALIA S.r.l. Process for preparing aryl-ethyl phenols having one or more alkyl substituents in the ethyl group and their use
US6049015A (en) * 1995-10-31 2000-04-11 Rhodia Chimie Method for C-alkylating hydroxylated aromatic compounds
US6255538B1 (en) * 2000-01-05 2001-07-03 Eastman Chemical Company Process for the C-alkylation of aromatic hydroxyl compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62263136A (en) * 1986-05-06 1987-11-16 Kuraray Co Ltd Production of 2,3,5-trimethylhydroquinone
FR2655331A1 (en) * 1989-12-05 1991-06-07 Rhone Poulenc Chimie PROCESS FOR THE PREPARATION OF SUBSTITUTED HYDROQUINONES
JP2739402B2 (en) * 1992-07-14 1998-04-15 富士写真フイルム株式会社 Dialkyl hydroquinone derivative and method for producing the same
JPH0733700A (en) * 1993-07-26 1995-02-03 Mitsui Toatsu Chem Inc Production of alkylidene-bis(dibromophenol)
JP2003128609A (en) * 2001-10-25 2003-05-08 Mitsubishi Gas Chem Co Inc Purification method of fluorenylidenediphenol

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2722556A (en) * 1952-03-19 1955-11-01 Eastman Kodak Co Preparation of tertiary butyl hydroquinone
WO1987005290A1 (en) * 1986-03-06 1987-09-11 Owens-Corning Fiberglas Corporation Process for the preparation of styrenated hydroquinone
EP0347835A2 (en) * 1988-06-21 1989-12-27 HIMONT ITALIA S.r.l. Process for preparing aryl-ethyl phenols having one or more alkyl substituents in the ethyl group and their use
US6049015A (en) * 1995-10-31 2000-04-11 Rhodia Chimie Method for C-alkylating hydroxylated aromatic compounds
US6255538B1 (en) * 2000-01-05 2001-07-03 Eastman Chemical Company Process for the C-alkylation of aromatic hydroxyl compounds

Also Published As

Publication number Publication date
GB0318209D0 (en) 2003-09-03
JP2007501211A (en) 2007-01-25
MXPA06001390A (en) 2006-08-25
JP4801586B2 (en) 2011-10-26
WO2005014568A2 (en) 2005-02-17
DE112004001345T5 (en) 2006-11-23

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