GB1111945A - Production of epoxy compounds - Google Patents

Production of epoxy compounds

Info

Publication number
GB1111945A
GB1111945A GB2417665A GB2417665A GB1111945A GB 1111945 A GB1111945 A GB 1111945A GB 2417665 A GB2417665 A GB 2417665A GB 2417665 A GB2417665 A GB 2417665A GB 1111945 A GB1111945 A GB 1111945A
Authority
GB
United Kingdom
Prior art keywords
hydroperoxide
benzene
cumene
ethyl
alcohol
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
GB2417665A
Inventor
Joseph Lee Russell
Charles Nathan Winnick
John Kollar
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.)
Halcon International Inc
Original Assignee
Halcon International Inc
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 Halcon International Inc filed Critical Halcon International Inc
Publication of GB1111945A publication Critical patent/GB1111945A/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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C11/00—Aliphatic unsaturated hydrocarbons
    • C07C11/02—Alkenes
    • C07C11/08—Alkenes with four carbon atoms
    • C07C11/09—Isobutene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
    • C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
    • C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
    • C07C15/46—Styrene; Ring-alkylated styrenes
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Epoxy compounds are produced by contacting a hydrocarbon having a secondary or tertiary saturated carbon atom with molecular oxygen to produce an organic hydroperoxide, reacting the hydroperoxide in the liquid phase with an olefinically unsaturated hydrocarbon having the same carbon skeletal structure in the presence of a metal epoxidation catalyst to produce an epoxy compound and the alcohol corresponding to the hydroperoxide, dehydrating at least part of the alcohol to the corresponding olefinically unsaturated hydrocarbon and epoxidizing this unsaturated hydrocarbon in the epoxidizing reaction with additional amounts of the organic hydroperoxide. The preferred hydrocarbons used as starting materials are aralkanes having at least one carbon atom on the alkyl carbon adjacent to the aromatic ring, e.g. ethyl benzene, cumene, ethyl toluene, p-cumene, tetrahydronaphthalene, p-diisopropyl benzene, ethyl naphthalene, isopropyl naphthalene, p-diethyl benzene, p-tertiary-butyl ethyl benzene and phenyl cyclo-hexane. Other suitable starting materials are, e.g., isobutane, isopentane, cyclohexane, methyl cyclohexane, dimethyl cyclohexanes and 2,5-dimethyl benzene. Suitable epoxidation catalysts are Ti, V, Cr, Se, Zr, Nb, Mo, Te, Ta, W, Re or U. In the Examples: (a) cumene is oxidized to cumene hydroperoxide which is reacted with a -methyl styrene to give a -methyl styrene oxide and cumyl alcohol; part of the cumyl alcohol is dehydrated to a -methyl styrene which is recycled with the rest of the cumyl alcohol to the epoxidation step; (b) ethyl benzene is oxidized to ethyl benzene hydroperoxide which is used to epoxidize styrene and phenylethanol which is dehydrated to styrene and recycled to the epoxidation step.
GB2417665A 1964-06-15 1965-06-08 Production of epoxy compounds Expired GB1111945A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US37531164A 1964-06-15 1964-06-15

Publications (1)

Publication Number Publication Date
GB1111945A true GB1111945A (en) 1968-05-01

Family

ID=23480373

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2417665A Expired GB1111945A (en) 1964-06-15 1965-06-08 Production of epoxy compounds

Country Status (8)

Country Link
JP (1) JPS5120483B1 (en)
BE (1) BE665405A (en)
DE (1) DE1518998C2 (en)
ES (1) ES314230A1 (en)
FR (1) FR1459796A (en)
GB (1) GB1111945A (en)
NL (1) NL6507188A (en)
SE (1) SE342448B (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100334045C (en) * 2003-03-26 2007-08-29 住友化学株式会社 Method for producing alpha-methylstyrene
WO2021021366A1 (en) * 2019-08-01 2021-02-04 Exxonmobil Research And Engineering Company Process and system to make olefin epoxides
CN112573980A (en) * 2019-09-30 2021-03-30 中国石油化工股份有限公司 Method for preparing isopropyl benzene, isopropyl benzene and propylene oxide
CN114426509A (en) * 2020-09-28 2022-05-03 中国石油化工股份有限公司 Method for simultaneously preparing multiple compounds and obtained compounds
US11827613B2 (en) 2019-08-01 2023-11-28 ExxonMobil Technology and Engineering Company Process and system to make olefin epoxides

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS52171389U (en) * 1976-06-18 1977-12-26

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100334045C (en) * 2003-03-26 2007-08-29 住友化学株式会社 Method for producing alpha-methylstyrene
WO2021021366A1 (en) * 2019-08-01 2021-02-04 Exxonmobil Research And Engineering Company Process and system to make olefin epoxides
CN114144403A (en) * 2019-08-01 2022-03-04 埃克森美孚研究工程公司 Process and system for preparing olefin epoxides
US11827613B2 (en) 2019-08-01 2023-11-28 ExxonMobil Technology and Engineering Company Process and system to make olefin epoxides
US11919876B2 (en) 2019-08-01 2024-03-05 ExxonMobil Technology and Engineering Company Process and system to make olefin epoxides
CN112573980A (en) * 2019-09-30 2021-03-30 中国石油化工股份有限公司 Method for preparing isopropyl benzene, isopropyl benzene and propylene oxide
CN114426509A (en) * 2020-09-28 2022-05-03 中国石油化工股份有限公司 Method for simultaneously preparing multiple compounds and obtained compounds
CN114426509B (en) * 2020-09-28 2024-05-28 中国石油化工股份有限公司 Method for preparing multiple compounds simultaneously and obtained compounds

Also Published As

Publication number Publication date
BE665405A (en) 1965-12-14
DE1518998C2 (en) 1982-03-18
ES314230A1 (en) 1965-09-01
SE342448B (en) 1972-02-07
DE1518998A1 (en) 1969-09-11
FR1459796A (en) 1966-11-25
JPS5120483B1 (en) 1976-06-25
NL6507188A (en) 1965-12-16

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