GB686692A - Improvements in or relating to nitriles - Google Patents

Improvements in or relating to nitriles

Info

Publication number
GB686692A
GB686692A GB9110/50A GB911050A GB686692A GB 686692 A GB686692 A GB 686692A GB 9110/50 A GB9110/50 A GB 9110/50A GB 911050 A GB911050 A GB 911050A GB 686692 A GB686692 A GB 686692A
Authority
GB
United Kingdom
Prior art keywords
butene
bromide
cyanogen
octene
aluminium
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
GB9110/50A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB686692A publication Critical patent/GB686692A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/02—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
    • C07C255/03—Mononitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/32—Separation; Purification; Stabilisation; Use of additives
    • C07C253/34—Separation; Purification

Landscapes

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

Abstract

Halonitriles and/or unsaturated nitriles are made by a catalytic reaction between an olefine and cyanogen chloride or bromide. Catalysts are mixtures or complexes of metal halides or of hydrogen fluoride with nitro-hydrocarbons. Preferred halides are tin tetrachloride, zinc and aluminium chloride, boron trifluoride and aluminium bromide. Olefines may be mono-, cyclo-, di- and conjugated di-olefines. At above about 25 DEG C. the halo-nitrile made by the addition of the cyanogen halide to the olefine is dehydrohalogenated to provide an a ,b - rather than a b g -unsaturated nitrile. Halonitriles are best made at below 25 DEG C. In examples, cyanogen chloride is reacted with (1) 1- and 2-butene, propene, cyclohexene, 1-octene and 1-dodecene; (2) and (4) propene; (3) cyclohexene; (5) and (13) 1-butene; (6) 1-octene; (7) 1-dodecene; (14) ethylene; and (15) 2-butene in the presence of a complex of aluminium chloride with nitromethane and in (16) and (17) with 2-butene in the presence of a boron trifluoride-nitromethane complex, and cyanogen bromide is reacted with (8) and (9) dipentene; (10) and (12) cyclohexane, and (11) 1-octene in the presence of an aluminium bromide-nitromethane complex, the products being the corresponding halo- and/or unsaturated nitriles according to the temperature of reaction. Inert solvents, e.g. carbon disulphide and monochlorobenzene may be present.
GB9110/50A 1949-04-20 1950-04-13 Improvements in or relating to nitriles Expired GB686692A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US686692XA 1949-04-20 1949-04-20

Publications (1)

Publication Number Publication Date
GB686692A true GB686692A (en) 1953-01-28

Family

ID=22083995

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9110/50A Expired GB686692A (en) 1949-04-20 1950-04-13 Improvements in or relating to nitriles

Country Status (1)

Country Link
GB (1) GB686692A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0419980A1 (en) * 1989-09-28 1991-04-03 Haarmann & Reimer Gmbh Alkadiene nitriles, process for their preparation and their use

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0419980A1 (en) * 1989-09-28 1991-04-03 Haarmann & Reimer Gmbh Alkadiene nitriles, process for their preparation and their use
US5105005A (en) * 1989-09-28 1992-04-14 Haarmann & Reimer Gmbh Alkadienenitriles, process for their preparation and their use

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