GB1020500A - A process for the production of an ether by the hydrogenolysis of a cyclic ketal - Google Patents

A process for the production of an ether by the hydrogenolysis of a cyclic ketal

Info

Publication number
GB1020500A
GB1020500A GB3939564A GB3939564A GB1020500A GB 1020500 A GB1020500 A GB 1020500A GB 3939564 A GB3939564 A GB 3939564A GB 3939564 A GB3939564 A GB 3939564A GB 1020500 A GB1020500 A GB 1020500A
Authority
GB
United Kingdom
Prior art keywords
ether
aryl
alkyl
cyclic ketal
hydrogen
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
GB3939564A
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
Publication of GB1020500A publication Critical patent/GB1020500A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
    • C07C41/28—Preparation of ethers by reactions not forming ether-oxygen bonds from acetals, e.g. by dealcoholysis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C07C43/13—Saturated ethers containing hydroxy or O-metal groups

Landscapes

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

Abstract

A process for the production of an ether having a hydroxy, alkoxy or aralkoxy group in the 2- or 3-position comprises reacting in the liquid phase a cyclic ketal of formula <FORM:1020500/C2/1> where each R independently is C1-8 alkyl or C6-10 aryl; each R1 independently is hydrogen, C1-8 alkyl or C6-10 aryl; X is hydrogen, hydroxy, C1-8 alkyl or C6-10 aryl; m is 0 or 1 and n is 0, 1, 2 or 3 with molecular hydrogen in the presence of a metal of Group VIII as hydrogenation catalyst and an acidic substance (including Lewis acids). Other metal promoters, e.g. chromium, may be present. Solvents are optionally used, preferably those alcohols or ether alcohols equivalent to parts of the cyclic ketal starting material. In examples: mixtures of ethylene glycol mono-and di-isopropyl ethers are obtained from 2,2-dimethyl - 1,3 - dioxolane and a mixture of 1-isopropoxy - 2 - propanol, 2 - isopropoxy - 1-propanol and propylene glycol diisopropyl ether from 2,2,4-trimethyl-1,3-dioxolane.
GB3939564A 1963-09-30 1964-09-28 A process for the production of an ether by the hydrogenolysis of a cyclic ketal Expired GB1020500A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US31235663A 1963-09-30 1963-09-30

Publications (1)

Publication Number Publication Date
GB1020500A true GB1020500A (en) 1966-02-16

Family

ID=23211089

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3939564A Expired GB1020500A (en) 1963-09-30 1964-09-28 A process for the production of an ether by the hydrogenolysis of a cyclic ketal

Country Status (4)

Country Link
BE (1) BE653656A (en)
DE (1) DE1234199B (en)
GB (1) GB1020500A (en)
NL (1) NL6411361A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4482753A (en) * 1983-03-28 1984-11-13 Olin Corporation Catalyst for use in the hydrogenolysis of methyl glycol formals
US4484009A (en) * 1982-04-20 1984-11-20 Atochem Process for the manufacture of glycol monoethers
US5446210A (en) * 1991-07-20 1995-08-29 Henkel Kommanditgesellschaft Auf Aktien Process for the production of polyol ethers
WO2012177484A1 (en) * 2011-06-24 2012-12-27 Eastman Chemical Company Catalysts for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
WO2012177469A1 (en) * 2011-06-24 2012-12-27 Eastman Chemical Company Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals
US8785697B2 (en) 2011-06-24 2014-07-22 Eastman Chemical Company Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US8829207B2 (en) 2011-06-24 2014-09-09 Eastman Chemical Company Production of cyclic acetals by reactive distillation
US8829206B2 (en) 2011-06-24 2014-09-09 Eastman Chemical Company Production of cyclic acetals or ketals using solid acid catalysts
US8969598B2 (en) 2011-06-24 2015-03-03 Eastman Chemical Company Production of cyclic acetals or ketals using liquid-phase acid catalysts
US9000229B2 (en) 2011-06-24 2015-04-07 Eastman Chemical Company Production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4479017A (en) * 1981-06-29 1984-10-23 Mitsubishi Petrochemical Co., Ltd. Process for producing ether compounds by catalytic hydrogenolysis
JP2841261B2 (en) * 1993-03-15 1998-12-24 花王株式会社 Method for producing ether alcohols
DE19621703A1 (en) * 1996-05-30 1997-12-04 Hoechst Ag Process for the preparation of 3-oxyalkylpropan-1-ols

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4484009A (en) * 1982-04-20 1984-11-20 Atochem Process for the manufacture of glycol monoethers
US4482753A (en) * 1983-03-28 1984-11-13 Olin Corporation Catalyst for use in the hydrogenolysis of methyl glycol formals
US5446210A (en) * 1991-07-20 1995-08-29 Henkel Kommanditgesellschaft Auf Aktien Process for the production of polyol ethers
US8969598B2 (en) 2011-06-24 2015-03-03 Eastman Chemical Company Production of cyclic acetals or ketals using liquid-phase acid catalysts
WO2012177469A1 (en) * 2011-06-24 2012-12-27 Eastman Chemical Company Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals
US8785697B2 (en) 2011-06-24 2014-07-22 Eastman Chemical Company Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US8829207B2 (en) 2011-06-24 2014-09-09 Eastman Chemical Company Production of cyclic acetals by reactive distillation
US8829206B2 (en) 2011-06-24 2014-09-09 Eastman Chemical Company Production of cyclic acetals or ketals using solid acid catalysts
WO2012177484A1 (en) * 2011-06-24 2012-12-27 Eastman Chemical Company Catalysts for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9000229B2 (en) 2011-06-24 2015-04-07 Eastman Chemical Company Production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9056313B2 (en) 2011-06-24 2015-06-16 Eastman Chemical Company Catalysts for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9315485B2 (en) 2011-06-24 2016-04-19 Eastman Chemical Company Production of cyclic acetals by reactive distillation
US9382179B2 (en) 2011-06-24 2016-07-05 Eastman Chemical Company Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9388105B2 (en) 2011-06-24 2016-07-12 Eastman Chemical Company Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals
US9394271B2 (en) 2011-06-24 2016-07-19 Eastman Chemical Company Production of cyclic acetals or ketals using liquid-phase acid catalysts
US9440944B2 (en) 2011-06-24 2016-09-13 Eastman Chemical Company Production of cyclic acetals or ketals using solid acid catalysts

Also Published As

Publication number Publication date
DE1234199B (en) 1967-02-16
BE653656A (en) 1965-03-29
NL6411361A (en) 1965-03-31

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