GB1399639A - Process for epoxidizing olefins with hydrogen peroxide - Google Patents

Process for epoxidizing olefins with hydrogen peroxide

Info

Publication number
GB1399639A
GB1399639A GB3752872A GB3752872A GB1399639A GB 1399639 A GB1399639 A GB 1399639A GB 3752872 A GB3752872 A GB 3752872A GB 3752872 A GB3752872 A GB 3752872A GB 1399639 A GB1399639 A GB 1399639A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
fluorine
chlorine
rcx
aug
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
GB3752872A
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 GB1399639A publication Critical patent/GB1399639A/en
Expired 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
    • 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
    • C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
    • 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
    • C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
    • 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
    • C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
    • 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
    • C07D303/28—Ethers with hydroxy compounds containing oxirane rings

Landscapes

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

Abstract

1399639 Epoxidation process SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ NV 11 Aug 1972 [13 Aug 1971] 37528/72 Heading C2C Olefinically unsaturated compounds are epoxidized with hydrogen peroxide in the presence of a catalyst consisting of one or more fluorinated ketones and/or fluorinated ketone hydrates which have the following formulae respectively: RCX 2 -COCY 2 R<SP>1</SP> and RCX 2 C(OH 2 )CY 2 R<SP>1</SP> in which R and R<SP>1</SP> are hydrogen, fluorine, chlorine, C 1 -C 10 alkyl, C 6 -C 10 aryl and X and Y are hydrogen, fluorine or chlorine, at least one X being fluorine and at least one Y being fluorine or chlorine. Preferred olefinically unsaturated compounds are those of Formula (a) in which R 1 , R 2 , R 3 and R 4 are hydrogen, C 1 - C 12 hydroxyhydrocarbyl, C 1 -C 12 hydrocarbyl free from acetylenic bonds with the proviso that two of R 1 , R 2 , R 3 and R 4 may form a hydroxyhydrocarbylene chain which together with the carbon atom to which they are attached forms a carbocyclic ring of up to 12 members or of Formula I in which R is C 3 -C 8 alkenyl, n is 1-3 and R<SP>1</SP> is hydrogen, C 3 -C 8 alkenyl or C 3 -C 8 epoxy alkyl. Examples are given of the epoxidation of octene- 1, propylene, allyl alcohol, 2,6-diallyl phenol, trans - stilbene, 1,3 - butadiene, 1,5 - cyclooctadiene, vinyl cyclohexane and 2,6-diallyl phenyl glycidyl ether.
GB3752872A 1971-08-13 1972-08-11 Process for epoxidizing olefins with hydrogen peroxide Expired GB1399639A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US17173471A 1971-08-13 1971-08-13

Publications (1)

Publication Number Publication Date
GB1399639A true GB1399639A (en) 1975-07-02

Family

ID=22624929

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3752872A Expired GB1399639A (en) 1971-08-13 1972-08-11 Process for epoxidizing olefins with hydrogen peroxide

Country Status (7)

Country Link
JP (1) JPS5711905B2 (en)
BE (1) BE787169A (en)
DE (1) DE2239681C3 (en)
FR (1) FR2149428B1 (en)
GB (1) GB1399639A (en)
IT (1) IT963971B (en)
NL (1) NL7211070A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4344887A (en) 1979-12-28 1982-08-17 General Electric Company Method for epoxidizing olefins
US4389529A (en) 1981-05-15 1983-06-21 General Electric Company Method for epoxidizing olefins
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
US4418203A (en) 1981-12-21 1983-11-29 Shell Oil Company Process for the epoxidation of olefins
EP0096130A1 (en) * 1982-06-11 1983-12-21 Exxon Research And Engineering Company Process for the epoxidation of olefins
CN104803951A (en) * 2015-05-15 2015-07-29 南京工业大学 Method for preparing high-quality cyclohexene oxide by adopting micro flow field reaction technology
CN106660978A (en) * 2014-08-27 2017-05-10 沙特基础工业全球技术有限公司 2-(2,3-epoxypropyl)phenol composition and method of making

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE863237A (en) * 1977-02-01 1978-07-24 Ugine Kuhlmann CATALYTIC EPOXIDATION PROCESS OF OLEFINS
FR2423486A1 (en) * 1978-04-19 1979-11-16 Roussel Uclaf NEW EPOXIDIZING REAGENT
DE3722486A1 (en) * 1987-07-03 1989-01-12 Schering Ag NEW EPOXY REAGENT AND ITS USE
JP5300218B2 (en) * 2006-06-23 2013-09-25 キヤノン株式会社 MICROSTRUCTURE, ITS MANUFACTURING METHOD, AND LIQUID DISCHARGE HEAD

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2786854A (en) * 1957-03-26 Process of making oxirane compounds

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4344887A (en) 1979-12-28 1982-08-17 General Electric Company Method for epoxidizing olefins
US4389529A (en) 1981-05-15 1983-06-21 General Electric Company Method for epoxidizing olefins
US4418203A (en) 1981-12-21 1983-11-29 Shell Oil Company Process for the epoxidation of olefins
EP0096130A1 (en) * 1982-06-11 1983-12-21 Exxon Research And Engineering Company Process for the epoxidation of olefins
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
CN106660978A (en) * 2014-08-27 2017-05-10 沙特基础工业全球技术有限公司 2-(2,3-epoxypropyl)phenol composition and method of making
EP3186235A4 (en) * 2014-08-27 2018-04-25 SABIC Global Technologies B.V. 2-(2,3-epoxypropyl)phenol composition and method of making
US10214503B2 (en) 2014-08-27 2019-02-26 Sabic Global Technologies B.V. 2-(2,3-epdxypropyl)phenol composition and method of making
CN104803951A (en) * 2015-05-15 2015-07-29 南京工业大学 Method for preparing high-quality cyclohexene oxide by adopting micro flow field reaction technology

Also Published As

Publication number Publication date
DE2239681C3 (en) 1981-12-24
DE2239681A1 (en) 1973-02-22
IT963971B (en) 1974-01-21
JPS4828403A (en) 1973-04-14
NL7211070A (en) 1973-02-15
FR2149428B1 (en) 1974-10-04
DE2239681B2 (en) 1981-02-26
JPS5711905B2 (en) 1982-03-08
BE787169A (en) 1973-02-05
FR2149428A1 (en) 1973-03-30

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee