GB646964A - Manufacture of an organic dinitrile - Google Patents
Manufacture of an organic dinitrileInfo
- 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
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.
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)
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 |
-
1948
- 1948-02-11 GB GB396948A patent/GB646964A/en not_active Expired
Cited By (2)
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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