GB402880A - A process for the preparation of addition compounds of hypochlorous acid or hypobromous acid with unsaturated organic compounds - Google Patents

A process for the preparation of addition compounds of hypochlorous acid or hypobromous acid with unsaturated organic compounds

Info

Publication number
GB402880A
GB402880A GB19215/32A GB1921532A GB402880A GB 402880 A GB402880 A GB 402880A GB 19215/32 A GB19215/32 A GB 19215/32A GB 1921532 A GB1921532 A GB 1921532A GB 402880 A GB402880 A GB 402880A
Authority
GB
United Kingdom
Prior art keywords
acid
hypochlorous
tertiary butyl
water
butyl 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
GB19215/32A
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.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
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 Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Publication of GB402880A publication Critical patent/GB402880A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/64—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens
    • C07C29/66—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by simultaneous introduction of -OH groups and halogens by addition of hypohalogenous acids, which may be formed in situ, to carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
    • C07C59/115—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

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

Abstract

Addition compounds of hypochlorous or hypobromous acid with organic compounds having one or more double carbon linkages in the molecule are manufactured by reacting the said unsaturated compounds in the presence of water with hypochlorous or hypobromous acid esters of tertiary alcohols (obtainable by passing chlorine or bromine into a mixture of water, tertiary alcohol, e.g. tertiary butyl or amyl alcohol, and alkali hydroxide or other basic substance). As organic compounds having one or more double carbon linkages in the molecule may be employed aliphatic olefines, e.g. ethylene, propylene or butylene, cyclic olefines, e.g. cyclohexene or pinene, diolefines, e.g. isoprene, oleic acid, cinnamic acid, eugenol, citral, allyl alcohol or crotonic acid. In a modification of the process, the hypochlorous or hypobromous acid esters of tertiary alcohols are caused to react in the presence of water on tertiary alcohols, which give rise to the formation of unsaturated hydrocarbons and water. In examples: (1) ethylene is introduced into a vessel provided with a gas-tight stirrer, a thermometer and a sieve-plate, containing water and the hypochlorous acid ester of tertiary butyl alcohol (obtainable from tertiary butyl alcohol and hypochlorous acid), yielding ethylene chlorhydrin; (2) a mixture of tertiary butyl alcohol containing water and the hypochlorous acid ester of tertiary butyl alcohol is refluxed to produce isobutylene chlorhydrin; (3) propylene is reacted as in (1) producing propylene chlorhydrin. Samples have been furnished under Section 2 (5) of: (1) isoprene dichlorhydrin, produced by reacting isoprene in ice water with the hypochlorous acid ester of tertiary butyl alcohol; (2) cyclohexene chlorhydrin (2-chlorocyclohexanol-1), produced similarly from cyclohexene; (3) cyclohexene bromhydrin (2-bromocyclohexanol-1) produced similarly by employing the hypobromous acid ester of tertiary butyl alcohol (obtained by adding bromine to aqueous tertiary butyl alcohol in the presence of yellow mercury oxide); (4) oleic acid chlorhydrin (9 : 10-chloroxystearic acid) produced by reacting potassium oleate in ice water with the hypochlorous acid ester of tertiary butyl alcohol and liberating the acid by means of nitric acid; (5) cinnamic acid chlorhydrin (phenylchlorolactic acid) produced by reacting potassium cinnamate in ice water with the same ester and liberating the acid by means of hydrochloric acid; w-chlorostyrene is obtained as a bye-product. The Specification as open to inspection under Sect. 91 comprises also the formation of the hypochlorous or hypobromous acid esters of tertiary alcohols in situ by bringing together the tertiary alcohol, water and chlorine or bromine, preferably in a weakly alkaline medium. This subject-matter does not appear in the Specification as accepted.
GB19215/32A 1931-07-25 1932-07-07 A process for the preparation of addition compounds of hypochlorous acid or hypobromous acid with unsaturated organic compounds Expired GB402880A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL402880X 1931-07-25

Publications (1)

Publication Number Publication Date
GB402880A true GB402880A (en) 1933-12-14

Family

ID=19785911

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19215/32A Expired GB402880A (en) 1931-07-25 1932-07-07 A process for the preparation of addition compounds of hypochlorous acid or hypobromous acid with unsaturated organic compounds

Country Status (1)

Country Link
GB (1) GB402880A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2557159A (en) * 1947-01-13 1951-06-19 Howard M Teeter Halogenated unsaturated higher fatty acids and derivatives
US2856417A (en) * 1954-10-22 1958-10-14 Shell Dev Halohydrination process
US2936314A (en) * 1957-05-16 1960-05-10 Swift & Co Preparation of halohydroxy fatty materials
FR2345431A2 (en) * 1976-03-23 1977-10-21 Lummus Co PROCESS FOR PREPARING ALKYLENE OXIDES

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2557159A (en) * 1947-01-13 1951-06-19 Howard M Teeter Halogenated unsaturated higher fatty acids and derivatives
US2856417A (en) * 1954-10-22 1958-10-14 Shell Dev Halohydrination process
US2936314A (en) * 1957-05-16 1960-05-10 Swift & Co Preparation of halohydroxy fatty materials
FR2345431A2 (en) * 1976-03-23 1977-10-21 Lummus Co PROCESS FOR PREPARING ALKYLENE OXIDES

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