GB886164A - Improvements in the production of epoxides - Google Patents

Improvements in the production of epoxides

Info

Publication number
GB886164A
GB886164A GB7996/59A GB799659A GB886164A GB 886164 A GB886164 A GB 886164A GB 7996/59 A GB7996/59 A GB 7996/59A GB 799659 A GB799659 A GB 799659A GB 886164 A GB886164 A GB 886164A
Authority
GB
United Kingdom
Prior art keywords
distillation
olefine
excess
reaction
acetic acid
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
GB7996/59A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB7996/59A priority Critical patent/GB886164A/en
Publication of GB886164A publication Critical patent/GB886164A/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
    • C07D301/12—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
    • C07D301/00—Preparation of oxiranes
    • C07D301/32—Separation; Purification
    • 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
    • C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals

Abstract

Epoxides, produced by reaction of monoolefines with 7-12 carbon atoms with peracetic acid, are separated from the reaction mixture by distillation in the presence of an excess of olefine which is at least sufficient to form an azeotropic mixture with the acetic acid formed. Preferably 25 to 100% excess of olefine is used. The excess of olefine may be added before the epoxidation reaction, or after the reaction and prior to the distillation. There may also be added an inert vehicle which boils above the boiling point of the epoxide, such as di-isopropylbenzene, diethylbenzene, or paraffin hydrocarbons before the distillation. The distillation is preferably carried out at temperatures below 100 DEG C., especially between 60 DEG and 80 DEG C., by appropriate reduction in pressure. The rise in temperature during distillation may be compensated for by reducing the pressure in stages. The first fraction is the diluent used in epoxidation, then the azeotrope of olefine and acetic acid. The acetic acid may be washed out or extracted with water and the olefine re-used, for example directly returned to the distillation column when working continuously. The last fraction is the pure epoxide.ALSO:Epoxides are produced by reaction of mono-olefines with 7 to 12 carbon atoms with peracetic acid and separation of the reaction mixture by distillation, wherein the distillation is carried out in the presence of an excess of olefine which is at least sufficient to form an azeotrope mixture with the acetic acid formed. Suitable olefines are heptene, n-octene, 2-ethylhexene, tripropylene, tetrapropylene, styrene, vinyl-cyclohexane, indene, 1-phenyl-1-propene, ethylcyclopentene and methylenecyclohexane. Mixtures of such olefines with one another or with saturated hydrocarbons may also be used. The peracetic acid may be used with diluents such as acetone, methyl ethyl ketone, ethyl acetate or butyl acetate. The epoxidation is preferably effected between 40 DEG C. and 50 DEG C. It is preferable to use an excess of 25% to 100% of olefine. The excess of olefine may be added after the reaction, if desired. An inert diluent which boils above the boiling point of the epoxide, such as di-isopropylbenzene, diethyl benzene or paraffin hydrocarbons, may be added for the distillation. The distillation is preferably effected at temperatures below 100 DEG C.
GB7996/59A 1959-03-09 1959-03-09 Improvements in the production of epoxides Expired GB886164A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB7996/59A GB886164A (en) 1959-03-09 1959-03-09 Improvements in the production of epoxides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB7996/59A GB886164A (en) 1959-03-09 1959-03-09 Improvements in the production of epoxides

Publications (1)

Publication Number Publication Date
GB886164A true GB886164A (en) 1962-01-03

Family

ID=9843784

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7996/59A Expired GB886164A (en) 1959-03-09 1959-03-09 Improvements in the production of epoxides

Country Status (1)

Country Link
GB (1) GB886164A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3222382A (en) * 1965-12-07 Recovered solvent
US3228967A (en) * 1966-01-11 Process for the direct epoxidation of olefins with molecular oxygen

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3222382A (en) * 1965-12-07 Recovered solvent
US3228967A (en) * 1966-01-11 Process for the direct epoxidation of olefins with molecular oxygen

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