GB451594A - Improvements relating to the production of nitriles - Google Patents
Improvements relating to the production of nitrilesInfo
- Publication number
- GB451594A GB451594A GB372835A GB372835A GB451594A GB 451594 A GB451594 A GB 451594A GB 372835 A GB372835 A GB 372835A GB 372835 A GB372835 A GB 372835A GB 451594 A GB451594 A GB 451594A
- Authority
- GB
- United Kingdom
- Prior art keywords
- ammonia
- passed
- acid
- mixture
- acids
- 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
- C07C253/22—Preparation of carboxylic acid nitriles by reaction of ammonia with carboxylic acids with replacement of carboxyl groups by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/20—Preparation of carboxylic acid nitriles by dehydration of carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Aliphatic nitriles are manufactured by passing a fatty acid containing at least 8, preferably at least 12 carbon atoms per molecule and free from hydroxy groups, or a functional derivative thereof, in the vapour phase together with ammonia over a dehydrating catalyst at 320--420 DEG C., preferably at 330--380 DEG C. Suitable starting materials are lauric, palmitic, stearic, oleic, linoleic and montanic acids, or mixtures thereof, e.g. those obtainable by saponifying fats, oils or waxes, e.g. coco-fat, palm kernel fat, linseed oil, tallow, train oil, beeswax or montan wax, carboxylic acids or mixtures thereof obtainable by oxidizing hard or soft paraffin wax, paraffin oil or mineral oil, also the amides of the acids, their esters with monovalent, preferably aliphatic, or polyvalent alcohols of low molecular weight, e.g. their methyl, ethyl, isopropyl, butyl and glycerol esters, or anhydrides, e.g. lauric anhydride or the mixed stearic-acetic anhydride. The reaction may be effected under ordinary, increased or reduced pressure, and advantageously with the addition of inert gaseous or vaporous diluents, e.g. hydrogen, nitrogen, carbon dioxide, air, or the vapours of methanol, acetic acid, nitriles or hydrocarbons. The materials treated may be vaporized in a separate chamber or in the reaction chamber. The nitriles are preferably treated before distillation or before further use with an acid or alkaline agent or an oxidizing agent, e.g. dilute hydrochloric acid, sulphuric acid, acetic acid, dilute alkali lye, potassium permanganate solution or hydrogen peroxide, in order to deodorize them. The products may be converted by hydrogenation into the corresponding amines. In examples: (1) the vapours of the mixture of acids obtainable by saponifying palm kernel fat are passed with ammonia and nitrogen over aluminium phosphate at 340--350 DEG C.; (2) the vapours of the acids obtainable by saponifying coco-fat are passed with ammonia over bauxite at 350--370 DEG C.; (3) hardened palm kernel fat is saponified with alkali and the acids are liberated from the soaps and passed with ammonia over silica gel at 360 DEG C.; (4) a vaporous mixture of stearic acid and cyclohexane is passed with ammonia over bauxite at 370--375 DEG C.; (5) oleic acid is vaporized in a current of superheated ammonia and the mixture is passed over aluminium oxide, partly dehydrated by heating, at 380--390 DEG C.; (6) oleic acid methyl ester is vaporized in the presence of ammonia and a little hydrogen, and the mixture is passed over silica gel at 370 DEG C.; a mixture of the methyl esters of the acids of coco-fat or of the acids obtainable by oxidation of paraffinic hydrocarbons of high molecular weight, e.g. paraffin wax, may be similarly treated; (7) palm kernel fat is vaporized and passed with ammonia and nitrogen over bauxite at 380 DEG C.; (8) molten coco-fatty acid is injected with ammonia into a high pressure apparatus containing kaolin and hydrated alumina at 350 DEG C.; (9) the acid mixture obtained by catalytic oxidation of paraffin wax is similarly treated at 360 DEG C.; (10) molten stearic acid and liquid ammonia are injected into a high pressure apparatus containing bauxite at 320 DEG C.; (11) coco-fatty acid and ammonia are passed in at the top of a vertical reaction vessel containing alumina and kaolin at 375 DEG C.; (12) lauric acid amide is vaporized in a stream of ammonia and the mixture is passed over aluminium oxide at 350--400 DEG C.; (13) stearic acid, preheated to 150 DEG C. and mixed with a little nitrogen, is evaporated by passing over plates in a chamber heated to 400--420 DEG C. to which preheated ammonia is supplied, and the resulting mixture is passed over bauxite at 400--420 DEG C.; (14) coconut oil, preheated to 100 DEG C., is passed with air and a gaseous diluent into the top of a evaporator filled with Raschig rings, into the bottom of which ammonia is supplied, whereby amides are produced and are passed over bauxite at 350--400 DEG C. Specification 416,631 is referred to.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB372835A GB451594A (en) | 1935-02-05 | 1935-02-05 | Improvements relating to the production of nitriles |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB372835A GB451594A (en) | 1935-02-05 | 1935-02-05 | Improvements relating to the production of nitriles |
Publications (1)
Publication Number | Publication Date |
---|---|
GB451594A true GB451594A (en) | 1936-08-05 |
Family
ID=9763823
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB372835A Expired GB451594A (en) | 1935-02-05 | 1935-02-05 | Improvements relating to the production of nitriles |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB451594A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0000916A1 (en) * | 1977-08-20 | 1979-03-07 | Hoechst Aktiengesellschaft | Process for the production of fatty acid nitriles and glycerine from glycerides, in particular from natural fats and/or oils |
WO2004012510A1 (en) * | 2002-08-06 | 2004-02-12 | Ecolab Inc. | Critical fluid antimicrobial compositions and their use and generation |
-
1935
- 1935-02-05 GB GB372835A patent/GB451594A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0000916A1 (en) * | 1977-08-20 | 1979-03-07 | Hoechst Aktiengesellschaft | Process for the production of fatty acid nitriles and glycerine from glycerides, in particular from natural fats and/or oils |
US4234509A (en) * | 1977-08-20 | 1980-11-18 | Hoechst Aktiengesellschaft | Process for the manufacture of fatty acid nitriles and glycerol from glycerides, especially from natural fats and oils |
WO2004012510A1 (en) * | 2002-08-06 | 2004-02-12 | Ecolab Inc. | Critical fluid antimicrobial compositions and their use and generation |
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