GB651797A - Preparation of 4-vinylcyclohexene dioxide - Google Patents
Preparation of 4-vinylcyclohexene dioxideInfo
- Publication number
- GB651797A GB651797A GB1577/48A GB157748A GB651797A GB 651797 A GB651797 A GB 651797A GB 1577/48 A GB1577/48 A GB 1577/48A GB 157748 A GB157748 A GB 157748A GB 651797 A GB651797 A GB 651797A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dioxide
- vinyl cyclohexene
- aqueous
- hypochlorite
- added
- 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
Links
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
- C07D303/04—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)
Abstract
4-Vinyl cyclohexene dioxide is prepared by dehydrohalogenating dichlorhydrins of 4-vinyl cyclohexene by treating with the hydroxide or carbonate of an alkali or alkaline earth metal, in an aqueous medium. Any temperature from the freezing point to the boiling point of the reaction mixture may be used but the preferred temperatures are 25 DEG C. and lower. The resulting dioxide may be isolated by extraction with a solvent for the dioxide which is unattacked by the oxide, e.g. chlorinated hydrocarbons, ether and aliphatic and aromatic hydrocarbons. The dichlorhydrins may be prepared as described in Specification 648,456. The following are representative of numerous examples: (1) a hypochlorite solution obtained by passing chlorine into an aqueous suspension of calcium carbonate followed by filtration, is added over a period to a stirred suspension of 4-vinyl cyclohexene in water at below 10 DEG C. and the resulting dichlorhydrins are isoated by ethereal extraction; the dichlorhydrins are added to aqueous sodium hydroxide with stirring at 25 DEG C. and the resulting dioxide isolated by extraction of the mixture with carbon tetrachloride; (4) chlorine is bubbled through an aqueous solution of sodium hydroxide at 3 DEG C. and to the resulting solution of hypochlorite is added 4-vinyl cyclohexene and then aqueous sulphuric acid sufficient to liberate most of the hypochlorous acid from the hypochlorite; aqueous sodium hydroxide is now added and sufficient sodium sulphite to decompose the excess hypochlorite, and the 4-vinyl cyclohexene dioxide produced is extracted as before; (8) chlorine gas is bubbled through aqueous sodium hydroxide at 3 DEG C., the resulting solution added slowly to a dispersion of 4-vinyl cyclohexene in aqueous sulphuric acid at not above 10 DEG C., then aqueous sodium hydroxide is added; the mixture is extracted with carbon tetrachloride and the extract distilled at 5 mm. pressure to isolate the dioxide, quantities of 4-vinyl cyclohexene monoxide appearing in the fore-runnings; (9) a hypochlorite solution obtained as in (8) is added slowly with vigorous stirring to a suspension of 4-vinyl cyclohexene in aqueous sulphuric acid at below 10 DEG C., the addition being stopped when test shows that hypochlorous acid is not rapidly taken up; at this stage an oil appears containing monochlorhydrins, so a solvent, ethylene dichloride, is added and addition of the hypochlorite continued; aqueous sodium hydroxide is then added and the dioxide is recovered from the ethylene dichloride layer; (11) chlorine is passed into an aqueous suspension of 4-vinyl cyclohexene until a positive test for hypochlorite persists, whereupon excess hypochlorite is decomposed by addition of sodium sulphite, and the dichlorhydrins converted to dioxide by addition of sodium hydroxide. The Specification as open to inspection under Sect. 91 refers to the preparation of 4-vinyl cyclohexene dioxide from the dichlorhydrins by dehydrohalogenation in general. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA651797X | 1947-01-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB651797A true GB651797A (en) | 1951-04-11 |
Family
ID=4172074
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1577/48A Expired GB651797A (en) | 1947-01-18 | 1948-01-19 | Preparation of 4-vinylcyclohexene dioxide |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB651797A (en) |
-
1948
- 1948-01-19 GB GB1577/48A patent/GB651797A/en not_active Expired
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB651797A (en) | Preparation of 4-vinylcyclohexene dioxide | |
US2000244A (en) | Process for separation and recovery of naphthenic acids and phenols | |
US1566818A (en) | Manufacture of alcohols | |
US2908716A (en) | Preparing organic sulfides | |
GB662218A (en) | Improvements in method of making vinyl chloride | |
GB668724A (en) | Process of making hydrophilic carbon black | |
GB414862A (en) | Improvements in the production of chlorinated rubber | |
GB402880A (en) | A process for the preparation of addition compounds of hypochlorous acid or hypobromous acid with unsaturated organic compounds | |
Brooks et al. | The Preparation of Benzoyl Hydrogen Peroxide | |
US1477130A (en) | Manufacture of hyposulphites | |
GB553317A (en) | Improvements in the production of alkaline earth metal pantothenates | |
GB404164A (en) | Improvements in the manufacture phenols from halogenated aromatic hydrocarbons | |
GB460376A (en) | Improvements in or relating to the production of chlorine dioxide | |
US2543952A (en) | Diallyl ether dichlorohydrins | |
US1768803A (en) | Method of recovering carbon bisulphide | |
SU76949A2 (en) | The method of obtaining trichlorobenzene | |
US2543992A (en) | Preparation of diallyl ether dichlorohydrins | |
GB652245A (en) | Improvements in insecticidal compositions and in their manufacture | |
GB770006A (en) | Process for the production of a hydroperoxide | |
US2414042A (en) | Making alkali metal sulfides | |
SU48288A1 (en) | Method for producing diethylmethanilic acid | |
GB549512A (en) | Manufacture of surface active materials | |
GB642459A (en) | Improvements in or relating to organic oxidation reactions | |
GB572690A (en) | Improvements relating to the removal of carbon disulphide from hydrocarbon liquids | |
GB211108A (en) | The manufacture of new sulphurized compounds of phenols |