GB646964A - Manufacture of an organic dinitrile - Google Patents

Manufacture of an organic dinitrile

Info

Publication number
GB646964A
GB646964A GB396948A GB396948A GB646964A GB 646964 A GB646964 A GB 646964A GB 396948 A GB396948 A GB 396948A GB 396948 A GB396948 A GB 396948A GB 646964 A GB646964 A GB 646964A
Authority
GB
United Kingdom
Prior art keywords
butene
hydrogen cyanide
diluent
hydrogen
cuprous
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
GB396948A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and 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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to GB396948A priority Critical patent/GB646964A/en
Publication of GB646964A publication Critical patent/GB646964A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/14—Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups

Landscapes

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

Abstract

In a process for the manufacture of 1 : 4-dicyano-2-butene a 1 : 4-dihalo-2-butene, wherein the halogen atoms are of atomic weight between 35 and 80, is reacted with hydrogen cyanide under non-alkaline conditions. Hydrogen halide produced in the reaction may be neutralized by reactants which do not produce alkalinity such as carbonates of magnesium, calcium, zinc and barium or, in the substantial absence of water, of an alkali cyanide. In the absence of an absorbing agent for hydrogen halides lower yields are obtained. An excess of hydrogen cyanide may be employed as a diluent or neutral liquids such as dioxane, benzene toluene, diethyl ether, aceto-nitrile and propionitrile, methanol, ethanol or 2-methoxy-ethanol. Cuprous halides and copper catalyze the reaction and the former also stabilizes hydrocyanic acid in the presence of stainless steel. In the presence of sufficient diluent other than hydrogen cyanide the reaction may be conducted at atmospheric pressure, otherwise it is desirable to use closed vessels. 1 : 4-dicyano-2-butene is obtained when in examples (1), (2) and (3) 1 : 4-dichloro-2-butene is heated with hydrogen cyanide in the presence of calcium carbonate and cuprous bromide, dioxane being present in the last example; (4) cuprous chloride and acetonitrile as diluent are used in a similar process to (2); (5), (6) and (7) cuprous chloride, bromide and iodide, respectively, are used in processes similar to (2); (8) a lower temperature is used in a similar process to (7); (9) and (10) metallic copper is used instead of a halide and water is added, the latter example being repeated with magnesium and barium carbonates instead of calcium carbonate and cuprous chloride instead of metallic copper; (11) 1 : 4-dichloro-2-butene is heated with hydrogen cyanide in the presence of anhydrous sodium cyanide and cuprous bromide; (12) methyl alcohol is present as a diluent in a process similar to (11), (13) 1 : 4-dichloro-2-butene is heated with hydrogen cyanide and copper powder alone. Specifications 646,965 and 646,966 are referred to.
GB396948A 1948-02-11 1948-02-11 Manufacture of an organic dinitrile Expired GB646964A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB396948A GB646964A (en) 1948-02-11 1948-02-11 Manufacture of an organic dinitrile

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB396948A GB646964A (en) 1948-02-11 1948-02-11 Manufacture of an organic dinitrile

Publications (1)

Publication Number Publication Date
GB646964A true GB646964A (en) 1950-11-29

Family

ID=9768302

Family Applications (1)

Application Number Title Priority Date Filing Date
GB396948A Expired GB646964A (en) 1948-02-11 1948-02-11 Manufacture of an organic dinitrile

Country Status (1)

Country Link
GB (1) GB646964A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1263751B (en) * 1964-11-14 1968-03-21 Basf Ag Process for the production of 1,4-dicyano-2-butene (= dihydromuconic acid dinitrile)
DE1518553B1 (en) * 1965-05-19 1970-03-26 Basf Ag Process for the preparation of 1,4-dicyano-2-butene from 1,2-dihalo-3-butene and / or 1,4-dihalo-2-butene and hydrocyanic acid

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1263751B (en) * 1964-11-14 1968-03-21 Basf Ag Process for the production of 1,4-dicyano-2-butene (= dihydromuconic acid dinitrile)
DE1518553B1 (en) * 1965-05-19 1970-03-26 Basf Ag Process for the preparation of 1,4-dicyano-2-butene from 1,2-dihalo-3-butene and / or 1,4-dihalo-2-butene and hydrocyanic acid

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