GB1170222A - Process for the preparation of Tetrahydrofuran and/or Homologues thereof - Google Patents

Process for the preparation of Tetrahydrofuran and/or Homologues thereof

Info

Publication number
GB1170222A
GB1170222A GB2744468A GB2744468A GB1170222A GB 1170222 A GB1170222 A GB 1170222A GB 2744468 A GB2744468 A GB 2744468A GB 2744468 A GB2744468 A GB 2744468A GB 1170222 A GB1170222 A GB 1170222A
Authority
GB
United Kingdom
Prior art keywords
tetrahydrofuran
diacylate
general formula
carboxylic acid
carbon atoms
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.)
Expired
Application number
GB2744468A
Inventor
Charles Francois Kohll
Henri Joseph Antonius Blaauw
Robert Van Helden
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to GB2744468A priority Critical patent/GB1170222A/en
Publication of GB1170222A publication Critical patent/GB1170222A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D307/08—Preparation of tetrahydrofuran

Abstract

1,170,222. Tetrahydrofurans. SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ N.V. 10 June, 1968, No. 27444/68. Heading C2C. A tetrahydrofuran of the general formula in which each R represents a hydrogen atom or a C 1 -C 5 alkyl group is prepared by (a) contacting a conjugated diolefin of general formula in an anhydrous, or substantially anhydrous, liquid medium, with a metal salt of an aliphatic carboxylic acid having 2-6 carbon atoms, together with a compound of divalent palladium, or with a divalent palladium salt of such a carboxylic acid alone; (b) separating from the reaction mixture one or more olefinically unsaturated 1,4-glycol acylates having the general formula in which at least one of the radicals R<SP>1</SP> and R<SP>2</SP> represents an acyl group having 2-6 carbon atoms, the other being the same or a hydrogen atom; (c) hydrogenating the ester obtained in (b) to give a saturated 1,4-glycol mono- and/or diacylate; and (d) converting the 1,4-glycol mono- and/or diacylate into the desired tetrahydrofuran, either directly by the action of an acidic catalyst in the presence of water or indirectly by first hydrolysing the mono- and/or diacylate and subsequently allowing the cyclization into the desired tetrahydrofuran to take place by methods known per se.
GB2744468A 1968-06-10 1968-06-10 Process for the preparation of Tetrahydrofuran and/or Homologues thereof Expired GB1170222A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2744468A GB1170222A (en) 1968-06-10 1968-06-10 Process for the preparation of Tetrahydrofuran and/or Homologues thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2744468A GB1170222A (en) 1968-06-10 1968-06-10 Process for the preparation of Tetrahydrofuran and/or Homologues thereof

Publications (1)

Publication Number Publication Date
GB1170222A true GB1170222A (en) 1969-11-12

Family

ID=10259697

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2744468A Expired GB1170222A (en) 1968-06-10 1968-06-10 Process for the preparation of Tetrahydrofuran and/or Homologues thereof

Country Status (1)

Country Link
GB (1) GB1170222A (en)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5129426A (en) * 1974-09-02 1976-03-12 Mitsubishi Chem Ind Jiasetokishibuten no suisokahoho
FR2283896A1 (en) * 1974-09-07 1976-04-02 Basf Ag TETRAHYDROFURAN PREPARATION PROCESS
FR2295037A1 (en) * 1974-12-20 1976-07-16 Gen Electric Tetrahydrofuran prepn. from 1,4-butanediol diesters - of carboxylic acids, by passing with water over hydrolysis-dehydroacyloxylating catalysts
US4005112A (en) * 1973-11-30 1977-01-25 General Electric Company Multistep method for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid
US4005113A (en) * 1973-12-03 1977-01-25 General Electric Company Multi-step process for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid
US4010171A (en) * 1973-12-03 1977-03-01 General Electric Company Process for preparing tetrahydrofuran
DE2704500A1 (en) * 1976-02-04 1977-08-11 Mitsubishi Chem Ind METHOD FOR MANUFACTURING TETRAHYDROFURAN
US4080366A (en) * 1975-11-26 1978-03-21 General Electric Company Conversion of esters of 1,4-butanediol to tetrahydrofuran
US4094887A (en) * 1976-03-16 1978-06-13 Mitsubishi Chemical Industries, Ltd. Process for preparing cyclic ethers
US4099018A (en) 1976-04-12 1978-07-04 Phillips Petroleum Company Method for the oxidation of a conjugated diolefin
US4100362A (en) 1976-11-19 1978-07-11 Phillips Petroleum Company Oxidation process
US4105679A (en) * 1976-02-04 1978-08-08 Mitsubishi Chemical Industries Ltd. Process for producing a cylic ether from an acetic ester of a 1,4-glycol
US4113971A (en) 1975-02-21 1978-09-12 Phillips Petroleum Company Process for preparing diacyloxy olefins
US4124600A (en) * 1975-05-28 1978-11-07 E. I. Du Pont De Nemours And Company Preparation of tetrahydrofuran
US4140704A (en) 1977-02-08 1979-02-20 Mitsubishi Chemical Industries Limited Process for producing cyclic ether
FR2399420A1 (en) * 1977-08-03 1979-03-02 Mitsubishi Chem Ind PROCESS FOR THE PRODUCTION OF HYDROFURAN AND 1,4-DIOL FROM 1,4-DIOL ACETATE AND PRODUCT OBTAINED BY THIS PROCESS, IN PARTICULAR TETRAHYDROFURANE AND 1,4-BUTANEDIOL
US4152525A (en) 1974-02-05 1979-05-01 Mitsubishi Chemical Industries Ltd. Method of recovering butadiene gas from an acetoxylation process
US4182901A (en) 1977-10-13 1980-01-08 Phillips Petroleum Company Diacyloxybutene isomerization with selenium dioxide
US4225729A (en) * 1974-03-28 1980-09-30 Mitsubishi Chemical Industries, Limited Process for hydrogenation of diacetoxybutene
US4237312A (en) 1979-04-02 1980-12-02 Phillips Petroleum Company Oxidation process including recovery and recycle of catalyst
JPS5629849B1 (en) * 1977-04-12 1981-07-10
JPS56113742A (en) * 1980-02-09 1981-09-07 Japan Synthetic Rubber Co Ltd Hydrogenation of diacetoxybutene

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4005112A (en) * 1973-11-30 1977-01-25 General Electric Company Multistep method for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid
US4010171A (en) * 1973-12-03 1977-03-01 General Electric Company Process for preparing tetrahydrofuran
US4005113A (en) * 1973-12-03 1977-01-25 General Electric Company Multi-step process for preparation of tetrahydrofuran starting from propylene, oxygen and a carboxylic acid
US4152525A (en) 1974-02-05 1979-05-01 Mitsubishi Chemical Industries Ltd. Method of recovering butadiene gas from an acetoxylation process
US4225729A (en) * 1974-03-28 1980-09-30 Mitsubishi Chemical Industries, Limited Process for hydrogenation of diacetoxybutene
JPS5129426A (en) * 1974-09-02 1976-03-12 Mitsubishi Chem Ind Jiasetokishibuten no suisokahoho
JPS5919931B2 (en) * 1974-09-02 1984-05-09 三菱化学株式会社 Hydrogenation method of diacetoxybutene
US4079068A (en) * 1974-09-07 1978-03-14 Basf Aktiengesellschaft Manufacture of tetrahydrofuran from the diacetate of 1,4-butanediol
FR2283896A1 (en) * 1974-09-07 1976-04-02 Basf Ag TETRAHYDROFURAN PREPARATION PROCESS
FR2295037A1 (en) * 1974-12-20 1976-07-16 Gen Electric Tetrahydrofuran prepn. from 1,4-butanediol diesters - of carboxylic acids, by passing with water over hydrolysis-dehydroacyloxylating catalysts
US4113971A (en) 1975-02-21 1978-09-12 Phillips Petroleum Company Process for preparing diacyloxy olefins
US4124600A (en) * 1975-05-28 1978-11-07 E. I. Du Pont De Nemours And Company Preparation of tetrahydrofuran
US4080366A (en) * 1975-11-26 1978-03-21 General Electric Company Conversion of esters of 1,4-butanediol to tetrahydrofuran
DE2704500A1 (en) * 1976-02-04 1977-08-11 Mitsubishi Chem Ind METHOD FOR MANUFACTURING TETRAHYDROFURAN
US4105679A (en) * 1976-02-04 1978-08-08 Mitsubishi Chemical Industries Ltd. Process for producing a cylic ether from an acetic ester of a 1,4-glycol
US4093633A (en) * 1976-02-04 1978-06-06 Mitsubishi Chemical Industries Limited Process for preparing tetrahydrofuran
US4094887A (en) * 1976-03-16 1978-06-13 Mitsubishi Chemical Industries, Ltd. Process for preparing cyclic ethers
US4099018A (en) 1976-04-12 1978-07-04 Phillips Petroleum Company Method for the oxidation of a conjugated diolefin
US4100362A (en) 1976-11-19 1978-07-11 Phillips Petroleum Company Oxidation process
US4140704A (en) 1977-02-08 1979-02-20 Mitsubishi Chemical Industries Limited Process for producing cyclic ether
JPS5629849B1 (en) * 1977-04-12 1981-07-10
FR2399420A1 (en) * 1977-08-03 1979-03-02 Mitsubishi Chem Ind PROCESS FOR THE PRODUCTION OF HYDROFURAN AND 1,4-DIOL FROM 1,4-DIOL ACETATE AND PRODUCT OBTAINED BY THIS PROCESS, IN PARTICULAR TETRAHYDROFURANE AND 1,4-BUTANEDIOL
US4182901A (en) 1977-10-13 1980-01-08 Phillips Petroleum Company Diacyloxybutene isomerization with selenium dioxide
US4237312A (en) 1979-04-02 1980-12-02 Phillips Petroleum Company Oxidation process including recovery and recycle of catalyst
JPS56113742A (en) * 1980-02-09 1981-09-07 Japan Synthetic Rubber Co Ltd Hydrogenation of diacetoxybutene
JPS6340177B2 (en) * 1980-02-09 1988-08-10 Japan Synthetic Rubber Co Ltd

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