GB916275A - Improvements in or relating to halogenated isocyanates - Google Patents

Improvements in or relating to halogenated isocyanates

Info

Publication number
GB916275A
GB916275A GB30585/61A GB3058561A GB916275A GB 916275 A GB916275 A GB 916275A GB 30585/61 A GB30585/61 A GB 30585/61A GB 3058561 A GB3058561 A GB 3058561A GB 916275 A GB916275 A GB 916275A
Authority
GB
United Kingdom
Prior art keywords
isocyanate
alkyl
halogen
isocyanates
chloride
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
GB30585/61A
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB916275A publication Critical patent/GB916275A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C07C265/14—Derivatives of isocyanic acid containing at least two isocyanate groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C07C265/02—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms
    • C07C265/04—Derivatives of isocyanic acid having isocyanate groups bound to acyclic carbon atoms of a saturated carbon skeleton

Landscapes

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

Abstract

Alkyl isocyanates having at least one halogen atom in the alpha position are obtained by reacting an alkyl isocyanate having at least one H atom in the a position, or an alkyl carbamic acid halide having at least one H atom in the a position, with a halogenating agent. Halogen gas may be flowed into an appropriate alkyl isocyanate whilst the mixture is subjected to ultra-violet light until the stoichiometric required amount of halogen has been absorbed, and thereafter the resulting halogeno alkyl isocyanate is removed by distillation. Halogen gas may be flowed into a suspension of an appropriate alkyl carbamic acid chloride while irradiating the suspension with U-V light, the reaction mixture being maintained at a temperature not exceeding 70 DEG C. during absorption of the halogen. Specified isocyanates which may be halogenated include methyl, ethyl, propyl, butyl, stearyl, cyclohexyl, b -cyanoethyl, and benzyl isocyanate; e -isocyanato p caproyl chloride; hexamethylene diisocyanate; carboxyethyl methyl isocyanate. Halogenation produces the corresponding a -mono or a -di-halogeno alkyl iso- or di-iso-cyanate. Halogeno alkyl carbamyl halides may be formed as intermediate products. These may be converted into isocyanates by heating. The halogenating agent may be chlorine, bromine, sulphuryl chloride, or sulphuryl bromide. During halogenation catalytically active halogen transfer agents such as ferric chloride may be present. Solvents may also be present. Examples describe the production of chloromethyl isocyanate, chloromethyl carbamyl chloride being formed as an intermediate and being converted to the isocyanate by heating to 120 DEG C. in a stream of nitrogen. 1.1.2.2-tetra-chloroethyl isocyanate, and a -chlorobenzyl isocyanate, and reference is made to the production of other isocyanates, including pentachloro - ethyl, a -bromo-benzyl, and a -bromo-b -chloro-ethylisocyanates, and 1.4-diisocyanato-1.4-dichlorocyclohexane. Specification 752,931 is referred to.
GB30585/61A 1960-08-26 1961-08-24 Improvements in or relating to halogenated isocyanates Expired GB916275A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF31985A DE1122058B (en) 1960-08-26 1960-08-26 Process for the preparation of ª-haloalkyl isocyanates

Publications (1)

Publication Number Publication Date
GB916275A true GB916275A (en) 1963-01-23

Family

ID=7094439

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30585/61A Expired GB916275A (en) 1960-08-26 1961-08-24 Improvements in or relating to halogenated isocyanates

Country Status (3)

Country Link
BE (1) BE607481A (en)
DE (1) DE1122058B (en)
GB (1) GB916275A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3437680A (en) * 1965-08-10 1969-04-08 Upjohn Co Trichloro-bromoalkyl isocyanates

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0025907B1 (en) * 1979-09-13 1984-06-20 BASF Aktiengesellschaft Halogenated tertiary alkyl isocyanates and process for their preparation
DE3013270A1 (en) * 1980-04-05 1981-10-15 Basf Ag, 6700 Ludwigshafen METHOD FOR PRODUCING 1-MONOCHLORAETHYLCARBAMIDSAEURECHLORID
DE3102089A1 (en) * 1981-01-23 1982-09-02 Basf Ag, 6700 Ludwigshafen HALOGENED, TERTIARY DIISOCYANATES AND METHOD FOR THE PRODUCTION THEREOF

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3437680A (en) * 1965-08-10 1969-04-08 Upjohn Co Trichloro-bromoalkyl isocyanates

Also Published As

Publication number Publication date
DE1122058B (en) 1962-01-18
BE607481A (en) 1961-12-18

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