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 Process for producing nitrile

Details
Inventors: Oku, Masayuki; Koshino, Junji;
Assignee: Kao Corporation (Tokyo, JP)
Primary Examiner: Higel; Floyd D.
Assistant Examiner: Sackey; Ebenezer
Attorney, Agent or Firm: Oblon, Spivak, McClelland, Maier & Neustadt, P.C.

A nitrile having formula (2): RC.ident.N (2) wherein R represents a substituted or unsubstituted alkyl, alkenyl, aralkyl or aryl group having 3 to 20 carbon atoms, is produced by a process, which comprises heating an aldoxime having formula (1): RCH.dbd.NOH (1) wherein R is as defined above, at 80 to 250.degree. C. in the presence of a catalyst (A) of an alkali metal or alkaline earth metal salt of a saturated or unsaturated mono- or dicarboxylic acid having 2 to 20 carbon atoms while removing product water from the reaction system by distillation.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS In formulae (1) and (2), the group represented by R contains 3 to 20 carbon atoms, preferably 6 to 14 carbon atoms.
Suitable alkyl groups, as R, include heptyl, nonyl, undecyl, lauryl and myristyl.
Suitable alkenyl groups, as R, include those having two or more double bonds such as 2,6-dimethyl-1,5-heptadienyl and 2,6-dimethyl-5-heptenyl.
Suitable aralkyl groups, as R, include 2-phenethyl and 2-styryl.
Suitable aryl groups, as R, include phenyl, methylphenvl and dimethylphenyl.
Of these, R preferably represents an alkenyl group which provides a conjugated system in the resulting nitrile, such as 2,6-dimethyl-1,5-heptadienyl group or 2-styryl.
The group, as R, is preferably unsubstituted.
However, the groups may be substituted with substituents which include cyano, hydroxyl, alkoxy, nitro, alkoxycarbonyl, amido, halogen and phenyl.
The aldoxime (1) raw material of the process of the present invention is obtained by, for example, reacting a corresponding aldehyde and an inorganic salt of hydroxylamine in a conventional manner.
Catalyst A employed in the present process, i.
e.
, an alkali metal or alkaline earth metal salt of a saturated or unsaturated mono- or dicarboxylic acid having 9 to 20 carbon atoms, includes the sodium, potassium or magnesium salt of a monocarboxylic acid, such as acetic acid, propionic acid, stearic acid or oleic acid; and a sodium or potassium salt of a dicarboxylic acid, such as oxalic acid or maleic acid.
Preferred salts include the alkali metal or alkaline earth metal salts of an aliphatic carboxylic acid.
From economic considerations, an alkali metal salt of a lower fatty acid having 2 to 5 carbon atoms is preferred, with sodium acetate or potassium acetate being particularly preferred.
These compounds can be used either individually or in a combination of two or more.
Catalyst A can be used in combination with another basic catalyst more basic than catalyst A, as long as the trans/cis ratio of the product nitrile is not adversely affected



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