GB1324763A - Phase transfer catalysis of heterogeneous reactions by quaternary salts - Google Patents

Phase transfer catalysis of heterogeneous reactions by quaternary salts

Info

Publication number
GB1324763A
GB1324763A GB1324763DA GB1324763A GB 1324763 A GB1324763 A GB 1324763A GB 1324763D A GB1324763D A GB 1324763DA GB 1324763 A GB1324763 A GB 1324763A
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GB
United Kingdom
Prior art keywords
oxidized
cyclohexene
diols
diol
cis
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
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.)
ConocoPhillips Co
Original Assignee
Continental Oil 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 Continental Oil Co filed Critical Continental Oil Co
Publication of GB1324763A publication Critical patent/GB1324763A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/285—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with peroxy-compounds

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1324763 Heterogeneous oxidation of olefins CONTINENTAL OIL CO 19 March 1971 7280/71 Addition to 1227144 Heading C2C A heterogeneous ionic oxidation is carried out between an olefin in a liquid phase and an oxidizing agent in a contiguous immiscible liquid phase in the presence of an organic quaternary salt having the formula where M is a pentavalent ion of an element consisting of nitrogen, phosphorus, arsenic, antimony or bismuth, R 1 , R 2 , R 3 and R 4 are hydrocarbon radicals wherein one of the hydrocarbon radicals may be substituted by a further quaternary group the total number of carbon atoms being from 18 to 70, and X- is an anion which will dissociate from the cation in an aqueous environment, said organic quaternary salt being substantially more soluble in the less polar of said reactant-containing phases than in the other of said reactantcontaining phases and a compound consisting of osmium, ruthenium, molybdenum, tungsten, selenium, vanadium, chromium, titanium, cerium, nickel, manganese, cobalt, platinum, iron, lead or palladium. In examples, 1-octene is oxidized to heptanol and heptenoic acid, cyclohexene is oxidized to cyclohexane-1,2-diol, cyclohexene oxide, cyclohexene-2-one and cyclohexen-2-ol, 1,5-hexadiene is oxidized to the corresponding epoxides, diols and tetraols, 3,3- dimethyl-1-butene is oxidized to the epoxide and diol, cis- and trans-2-hexenes and 2-octenes were oxidized to the cis- and trans-epoxides and the erythro- and threo-diols and styrene is oxidized to styrene oxide and 2-phenyl-1,2- ethanediol.
GB1324763D 1971-03-19 1971-03-19 Phase transfer catalysis of heterogeneous reactions by quaternary salts Expired GB1324763A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB728071 1971-03-19

Publications (1)

Publication Number Publication Date
GB1324763A true GB1324763A (en) 1973-07-25

Family

ID=9830069

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1324763D Expired GB1324763A (en) 1971-03-19 1971-03-19 Phase transfer catalysis of heterogeneous reactions by quaternary salts

Country Status (1)

Country Link
GB (1) GB1324763A (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2605041A1 (en) * 1975-02-11 1976-08-26 Ugine Kuhlmann METHOD OF EPOXYDATING OLEFINS
US4016190A (en) * 1975-03-01 1977-04-05 Bayer Aktiengesellschaft Process for the preparation of diarylcarbonates
US4079075A (en) * 1975-11-06 1978-03-14 The Dow Chemical Company Primary alkyl esters as mediums for oxidations by phase-transfer catalyzed hypohalites
US4328170A (en) * 1978-11-02 1982-05-04 Matsumoto Seiyaku Kogyo Kabushiki Kaisha Process for preparing an α-cyanoacrylate
EP0053023A1 (en) * 1980-11-24 1982-06-02 Exxon Research And Engineering Company Hydroxylation of olefins
EP0077201A3 (en) * 1981-10-09 1983-06-22 Exxon Research And Engineering Company Hydroxylation of olefins
EP0077202A3 (en) * 1981-10-09 1983-06-22 Exxon Research And Engineering Company Process for hydroxylating olefins using osmium-halogen compound catalysts
US4410715A (en) 1982-07-14 1983-10-18 Exxon Research & Engineering Co. Process for the epoxidation of olefins using a group V metal co-catalyst I and a phenolic hydrocarbon co-catalyst II
GB2129800A (en) * 1982-11-12 1984-05-23 Exxon Research Engineering Co Process for hydroxylating olefins using an osmium oxide catalyst and sodium hydroxide co-catalyst
EP0122804A1 (en) * 1983-04-15 1984-10-24 Montedison S.p.A. Process for preparing carboxylic acids from olefins or vicinal dihydroxy compounds
FR2612512A1 (en) * 1987-03-20 1988-09-23 Lille 11 Universite Droit Sant PROCESS FOR OXIDIZING ORGANIC COMPOUNDS BY OXYGENATED WATER IN THE PRESENCE OF A CATALYST
WO1993012064A1 (en) * 1991-12-11 1993-06-24 Novamont S.P.A. A method of preparing carboxylic acids or esters thereof by the oxidative cleavage of unsaturated fatty acids or esters thereof
WO1995000243A1 (en) * 1993-06-25 1995-01-05 Solvay Interox Limited Oxidative cleavage of alkenes
US5939572A (en) * 1995-06-05 1999-08-17 North Dakota State University Research Foundation Method for preparation of carboxylic acids

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2605041A1 (en) * 1975-02-11 1976-08-26 Ugine Kuhlmann METHOD OF EPOXYDATING OLEFINS
US4016190A (en) * 1975-03-01 1977-04-05 Bayer Aktiengesellschaft Process for the preparation of diarylcarbonates
US4079075A (en) * 1975-11-06 1978-03-14 The Dow Chemical Company Primary alkyl esters as mediums for oxidations by phase-transfer catalyzed hypohalites
US4328170A (en) * 1978-11-02 1982-05-04 Matsumoto Seiyaku Kogyo Kabushiki Kaisha Process for preparing an α-cyanoacrylate
EP0053023A1 (en) * 1980-11-24 1982-06-02 Exxon Research And Engineering Company Hydroxylation of olefins
EP0077201A3 (en) * 1981-10-09 1983-06-22 Exxon Research And Engineering Company Hydroxylation of olefins
EP0077202A3 (en) * 1981-10-09 1983-06-22 Exxon Research And Engineering Company Process for hydroxylating olefins using osmium-halogen compound catalysts
US4410715A (en) 1982-07-14 1983-10-18 Exxon Research & Engineering Co. Process for the epoxidation of olefins using a group V metal co-catalyst I and a phenolic hydrocarbon co-catalyst II
GB2129800A (en) * 1982-11-12 1984-05-23 Exxon Research Engineering Co Process for hydroxylating olefins using an osmium oxide catalyst and sodium hydroxide co-catalyst
EP0122804A1 (en) * 1983-04-15 1984-10-24 Montedison S.p.A. Process for preparing carboxylic acids from olefins or vicinal dihydroxy compounds
FR2612512A1 (en) * 1987-03-20 1988-09-23 Lille 11 Universite Droit Sant PROCESS FOR OXIDIZING ORGANIC COMPOUNDS BY OXYGENATED WATER IN THE PRESENCE OF A CATALYST
EP0288337A1 (en) * 1987-03-20 1988-10-26 Universite Du Droit Et De La Sante (Lille Ii) Process for the oxidation of organic compounds by hydrogen peroxide in the presence of a catalyst
WO1993012064A1 (en) * 1991-12-11 1993-06-24 Novamont S.P.A. A method of preparing carboxylic acids or esters thereof by the oxidative cleavage of unsaturated fatty acids or esters thereof
US5336793A (en) * 1991-12-11 1994-08-09 Novamont S.P.A. Preparing carboxylic acids or esters by oxidative cleavage of unsaturated fatty acids or esters
AU658957B2 (en) * 1991-12-11 1995-05-04 Novamont S.P.A. A method of preparing carboxylic acids or esters thereof by the oxidative cleavage of unsaturated fatty acids or esters thereof
WO1995000243A1 (en) * 1993-06-25 1995-01-05 Solvay Interox Limited Oxidative cleavage of alkenes
US5939572A (en) * 1995-06-05 1999-08-17 North Dakota State University Research Foundation Method for preparation of carboxylic acids

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Legal Events

Date Code Title Description
PS Patent sealed
746 Register noted 'licences of right' (sect. 46/1977)
PE20 Patent expired after termination of 20 years