Classifications

• • 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
  • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso 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
  • C07D303/48—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

Definitions

• the present invention relates to a process for the preparation of halogen-substituted oxiranes from halogen-substituted polyenes and percarboxylic acids and to new 2-chloro-2-vinyl and 2-chloro-3-vinyl-oxiranes.
• vinyl oxiranes substituted on the oxirane ring or on the vinyl group by halogen are particularly important as monomers. They can therefore be used in the field of paints and plastics, organic intermediates and in crop protection, which is particularly useful for the new compounds with 2-chloro-2-vinyl-oxirane and 2-chloro-3-vinyl oxirane structure is of interest.
• chloroprene 2,3-dichlorobutadiene, 1,3-chloroburadiene and 1-chlorobutadiene.
• the various hydrocarbons can be used as organic solvents, for example aliphatic and cycloaliphatic hydrocarbons such as hexane, heptane, octane, 2-ethylhexane, decane, dodecane, cyclohexane, methylcyclopentane, petroleum ether; aromatic hydrocarbons such as benzene, nitrobenzene, toluene, ethylbenzene, cumene, diisopropylbenzene, xylene, chlorobenzene; oxygenated hydrocarbons such as diethyl ether, Dibutyl ether, tetrahydrofuran, dioxane, P Yran, acetone, methyl ethyl ketone, ethyl acetate, Propyl acetate, butyl acetate, methyl propionate, propionic acid, ethyl ester, Butyric acid methyl ester, but
• Particularly preferred solvents are the chlorinated hydrocarbons from the aromatic of the hydrocarbons cyclohexane Hydrocarbons ethyl propionate.
• the heat of reaction is or external coolers.
• To the reaction can also be carried out under reflux, ie in boiling reactors.
• the reaction is expediently carried out with the most complete possible formation of the percarboxylic acid. In general, more than 95 mol% of the percarboxylic acid is reacted. It is expedient to convert more than 98 mol% peracid.
• the reaction mixture is worked up in a manner known per se, for example by distillation.
• an approximately 20% by weight propiffene solution in benzene is added with stirring to the double molar amount of halogen-substituted polyene which is thermostatted at 30 ° C.
• the perpropionic acid solution holds less than 10 ppm mineral acid; it has a water content which is below 0.1% and has a hydrogen peroxide ehalt g of less than 0.3%.
• To complex heavy metal ions about 0.05% by weight Na 5 (2-ethylhexyl) 5 (P 3 O 10 ) 2 was added to the perpropionic acid before the reaction. The progress and the end of the reaction are checked by taking samples from the reaction solution at intervals and determining the still present content of percarboxylic acid by titration. After the end of the reaction, the reaction mixture is fractionated.
• the reaction mixture was worked up by distillation. First of all, chloroprene, benzene and the two oxiranes were taken off as top product in a distillation column equipped with a thin-layer evaporator, while propionic acid was obtained at the bottom.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Epoxy Compounds (AREA)

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Citations (3)

• 1977
  • 1977-07-29 DE DE19772734243 patent/DE2734243A1/de not_active Withdrawn
• 1978
  • 1978-07-18 EP EP78100421A patent/EP0000535B1/fr not_active Expired
  • 1978-07-18 DE DE7878100421T patent/DE2861847D1/de not_active Expired
  • 1978-07-29 JP JP9209078A patent/JPS5427515A/ja active Pending

Patent Citations (3)

Non-Patent Citations (1)

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