GB628659A - Improvements in and relating to the synthesis of organic nitrogen compounds - Google Patents
Improvements in and relating to the synthesis of organic nitrogen compoundsInfo
- Publication number
- GB628659A GB628659A GB1321547A GB1321547A GB628659A GB 628659 A GB628659 A GB 628659A GB 1321547 A GB1321547 A GB 1321547A GB 1321547 A GB1321547 A GB 1321547A GB 628659 A GB628659 A GB 628659A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cobalt
- propionamide
- ammonia
- carbon monoxide
- catalyst
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Organic nitrogen compounds such as amides, nitriles and lactams, are prepared by reacting at a pressure above 50 atmos., carbon monoxide, and ammonia or an amine NHR2, where R is hydrogen or an organic radical, with a compound having at least one non-benzenoid double bond between carbon atoms, in the presence of a hydrogenating catalyst at elevated temperature. A single compound may constitute both the amine and the unsaturated compound. The unsaturated compound may be an olefin, diolefin, cyclo-olefin, cracked petroleum fraction, diene polymer, ester, ether, carboxylic acid, nitrile, amide, amine, aldehyde or ketone, examples being given. The groups R may be the same or different and include alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, aralkyl, or derivatives thereof containing, for example, hydroxy, amino or alkoxy substituents. Temperatures are generally about 150-350 DEG C., and pressures may be up to 2000-3000 atm. or more. Suitable catalysts are Co, Ni, Ru, Cu, their compounds and alloys, if desired with supports or promoters. Cobalt carbonyl is preferred and may be used in an amount of a few tenths per cent of the reaction mixture, preferably in an inert solvent. Metallic cobalt or nickel, cobalt chromite, cobalt-substituted amides, and cobalt carboxylates are also suitable. Liquid or vapour phase reaction in reactors lined with silver or of material yielding cobalt carbonyl may be used. Amides are the principal products but, at higher temperatures, nitrile formation may be appreciable. Unsaturated esters may yield diamides or imides. In examples: (1) and (2) reduced sintered cobalt oxide, diethyl ether, dimethylamine, ethylene, and carbon monoxide under pressure are heated to yield N,N-dimethyl propionamide; (3) and (4) ammonia is used with either ether or benzene as solvent giving propionamide; (5) the only catalyst is a minute amount of cobalt adhering to the silver-lined reactor; (6) crude cobalt-containing propionamide prepared as in (3) is catalyst, the products being propionamide and propionitrile; (7) propylene and ammonia with carbon monoxide give n-butyramide and di-isopropyl ketone; (8) butene-1 similarly yields n-valeramide; (9) cobalt carbonyl is catalyst for preparation of cobalt-containing crude propionamide from ethylene and ammonia; (10) the N,N-dimethyl amide of 3 - cyclohexene - 1 - carboxylic acid, prepared from the methyl ester and dimethylamine, with dimethylamine and carbon monoxide, yields the N,N,N1,N1-tetramethyl diamide of cyclohexane dicarboxylic acids; (11) cobalt propionate, propionamide, ammonia, ethylene, and carbon monoxide are heated to yield propionamide and a crude cobalt-containing residue which is recycled; (12) using vinylcyclohexene and dimethylamine, an N,N - dimethylamide C11H19ON is formed together with dimethylformamide, which can be recycled to yield further dimethylamide; (13) alkylamine and carbon monoxide yield g -butyrolactam; (14) and (15) propionamide and diethyl ketone are formed using ammonia and ethylene, and a nickel or copper propionate catalyst.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1321547A GB628659A (en) | 1947-05-16 | 1947-05-16 | Improvements in and relating to the synthesis of organic nitrogen compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1321547A GB628659A (en) | 1947-05-16 | 1947-05-16 | Improvements in and relating to the synthesis of organic nitrogen compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB628659A true GB628659A (en) | 1949-09-01 |
Family
ID=10018915
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1321547A Expired GB628659A (en) | 1947-05-16 | 1947-05-16 | Improvements in and relating to the synthesis of organic nitrogen compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB628659A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2898345A (en) * | 1956-02-17 | 1959-08-04 | Texaco Inc | Synthesis of substituted succinyl compounds |
US2958695A (en) * | 1954-10-20 | 1960-11-01 | Texaco Inc | Synthesis of substituted succinyl compounds |
US3412151A (en) * | 1966-06-17 | 1968-11-19 | Shell Oil Co | Dimethylformamide production |
US3523971A (en) * | 1966-05-26 | 1970-08-11 | Union Oil Co | Synthesis of acrylamides |
-
1947
- 1947-05-16 GB GB1321547A patent/GB628659A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2958695A (en) * | 1954-10-20 | 1960-11-01 | Texaco Inc | Synthesis of substituted succinyl compounds |
US2898345A (en) * | 1956-02-17 | 1959-08-04 | Texaco Inc | Synthesis of substituted succinyl compounds |
US3523971A (en) * | 1966-05-26 | 1970-08-11 | Union Oil Co | Synthesis of acrylamides |
US3412151A (en) * | 1966-06-17 | 1968-11-19 | Shell Oil Co | Dimethylformamide production |
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