GB794209A - Improvements in and relating to the synthesis of 1, 4-dichloro-2, 3-butanediol and butadiene dioxide - Google Patents

Improvements in and relating to the synthesis of 1, 4-dichloro-2, 3-butanediol and butadiene dioxide

Info

Publication number
GB794209A
GB794209A GB19225/55A GB1922555A GB794209A GB 794209 A GB794209 A GB 794209A GB 19225/55 A GB19225/55 A GB 19225/55A GB 1922555 A GB1922555 A GB 1922555A GB 794209 A GB794209 A GB 794209A
Authority
GB
United Kingdom
Prior art keywords
dichloro
ether
epoxybutane
mixture
water
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
GB19225/55A
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.)
Union Carbide Corp
Original Assignee
Union Carbide Corp
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 Union Carbide Corp filed Critical Union Carbide Corp
Publication of GB794209A publication Critical patent/GB794209A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/34—Halogenated alcohols
    • C07C31/42—Polyhydroxylic acyclic alcohols
    • 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
    • C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals

Landscapes

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

Abstract

1,4-Dichloro-2,3-butane diol is produced by a process comprising hydrolysing 1,4-dichloro-2,3-epoxybutane by heating it with water in the presence of an acidic hydrolysis catalyst. The diol may then be dehydrochlorinated by reacting it with a finely-divided alkali hydroxide in a water-immiscible ether to produce butadiene dioxide. Preferably the 1,4-dichloro-2,3-epoxybutane is hydrolysed in the presence of water and a water-immiscible organic ether in which the 1,4 - dichloro - 2,3 - epoxybutane is substantially soluble, such as dioxane, tetrahydrofurane, dimethyl ether, ethyleneglycol dimethyl ether and diethylene glycol diethyl ether. The hydrolysis step is preferably carried out at a temperature in the range 50 DEG to 175 DEG C. and the preferred hydrolysis catalyst is sulphuric acid. Suitable ethers for use in the dehydrochlorination step are, for example, diethyl ether, n-butyl ether, isopropyl ether and n-hexyl ether. Preferably an anhydrous salt, e.g. sodium sulphate, magnesium sulphate, potassium carbonate or calcium sulphate, is added to the mixture in the dehydrochlorination step. The 1.4-dichloro-2,3-epoxybutane used as starting material may be obtained by chlorinating butadiene and treating 1,4-dichloro-2-butene obtained with peracetic acid. In the examples, 1,4-dichloro-2,3-epoxybutane is added to a mixture of dioxane and concentrated sulphuric acid and the mixture is heated to give 1,4-dichloro-2,3-butanediol; the 1,4-dichloro-2,3-butanediol is added to diethyl ether and the mixture is treated with potassium or sodium hydroxide to give butadiene dioxide. Specification 735,974 is referred to.
GB19225/55A 1954-07-06 1955-07-04 Improvements in and relating to the synthesis of 1, 4-dichloro-2, 3-butanediol and butadiene dioxide Expired GB794209A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US794209XA 1954-07-06 1954-07-06

Publications (1)

Publication Number Publication Date
GB794209A true GB794209A (en) 1958-04-30

Family

ID=22150433

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19225/55A Expired GB794209A (en) 1954-07-06 1955-07-04 Improvements in and relating to the synthesis of 1, 4-dichloro-2, 3-butanediol and butadiene dioxide

Country Status (1)

Country Link
GB (1) GB794209A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0209060A2 (en) * 1985-07-17 1987-01-21 Hoechst Aktiengesellschaft Process for the preparation of diols and tetrols containing fluorine

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0209060A2 (en) * 1985-07-17 1987-01-21 Hoechst Aktiengesellschaft Process for the preparation of diols and tetrols containing fluorine
EP0209060A3 (en) * 1985-07-17 1989-02-01 Hoechst Aktiengesellschaft Process for the preparation of diols and tetrols containing fluorine

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