Organic compounds -- part of the class 532-570 series – Organic compounds – Nitrogen attached directly or indirectly to the purine ring...
Patent
1980-04-03
1982-05-11
Demers, Arthur P.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitrogen attached directly or indirectly to the purine ring...
2602391, 544386, 546245, 564133, 564138, 564139, 564141, 564161, 564215, 549487, C07D29510
Patent
active
043294626
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a process for producing carboxylic amides. More particularly, it relates to a process for producing carboxylic amides by oxidative reaction of primary alcohols with ammonia or an amine.
BACKGROUND ART
It is well-known that carboxylic amides, industrially useful materials, are produced by reaction of carboxylic acids or esters thereof with an amine, which reaction is applicable as a general method of making them, or hydrolysis of the corresponding nitriles. The yield in each of these processes has arrived at an almost satisfactory level owing to the recent development of the technology, but both these processes need long routes from the petroleum chemical raw materials. As an approach to shortening these routes, for instance, a method as disclosed in British Pat. No. 925588 is known, wherein reaction of carbon monoxide with dimethylamine is effected for the production of N,N-dimethylformamide; however, it requires a high pressure as well as troublesome procedure for treatment of the by-products such as formic acid and others. Consequently, development of a simpler and more economical process has been looked for in the industry.
DISCLOSURE OF INVENTION
This invention provides a process for producing carboxylic amides, characterized in that (a) a primary alcohol is allowed to react with (b) at least one compound selected from the group consisting of ammonia, primary amines, and secondary amines in the presence of (c) a molecular oxygen-containing gas and (d) a palladium or platinum catalyst. According to this invention, carboxylic amides can be produced with simplicity and convenience.
BEST MODE FOR CARRYING OUT THE INVENTION
One of the starting materials used in this invention is a primary alcohol. Examples of the primary alcohol are monohydric alcohols including saturated aliphatic primary alcohols such as methanol, ethanol, isopropyl alcohol, n-butyl alcohol, 2-ethylhexanol, and n-octyl alcohol; unsaturated aliphatic primary alcohol such as allyl alcohol and crotyl alcohol; aromatic alcohols such as benzyl alcohol and cinnamyl alcohol; heterocyclic alcohols such as pyridyl alcohols and furfuryl alcohol. The above-mentioned aromatic alcohols also include that which has been substituted in the aromatic ring by a halogen atom such as chlorine, bromine, or fluorine, by a C.sub.1 to C.sub.5 alkyl group such as methyl, ethyl, isopropyl, or n-amyl, by a C.sub.1 to C.sub.5 haloalkyl group such as chloromethyl or bromoethyl; or by an alkoxy group such as methoxy or ethoxy. The above-mentioned heterocyclic alcohols also include that which has been substituted in the heterocyclic ring by a C.sub.1 to C.sub.5 alkyl group such as methyl, ethyl, isopropyl, or n-amyl, or by a C.sub.1 to C.sub.5 haloalkyl group such as chloromethyl or bromoethyl. Also, polyhydric alcohols such as ethylene glycol, propylene glycol, glycerin, and the like may be used.
Among these primary alcohols, those excellent in respect of reactivity in the process of this invention are methyl alcohol; a primary alcohol having no hydrogen atom attached to the carbon atom next to the carbon atom to which the alcoholic hydroxyl group is attached, such as non-substituted or substituted benzyl alcohols, non-substituted or substituted pyridylcarbinols, or non-substituted or substituted furfuryl alcohols; a primary alcohol having an unsaturated bond at the carbon atom adjoining to the carbon atom to which the alcoholic hydroxyl group is attached, such as allyl alcohol or crotyl alcohol; particularly, methyl alcohol, benzyl alcohol, pyridylcarbinols, and furfuryl alcohol are most preferable.
Another starting material used in this invention is ammonia, a primary amine, or a secondary amine. The followings are the typical examples of the primary amine, but any other primary amine may be used: aliphatic primary amines such as methylamine, ethylamine, propylamine, isopropylamine, and butylamine; alicylic primary amines such as cyclopropylamine, cyclopentylamine, and cyclohexylamine; aromatic primary amines
REFERENCES:
patent: 2617805 (1952-11-01), Wissow
patent: 3192258 (1965-06-01), Nakagawa et al.
patent: 3226390 (1965-12-01), Nakagawa et al.
patent: 4126748 (1978-11-01), Scholz et al.
Carruthers, Some Modern Methods of Organic Synthesis, University Press, Cambridge, 1971, pp. 251-259.
Nakagawa et al. (III), J. Org. Chem., 27 (1962), pp. 1597-1601.
Fukuoka Yohei
Nishikido Joji
Suzuki Yoshio
Tamura Nobuhiro
Yamamatsu Setsuo
Asahi Kasei Kogyo Kabushiki Kaisha
Demers Arthur P.
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