Stamicarbon B.v.

Leonardus H Geurts

Sijbrandus E Schaafsma

Peter J Meijer

Gerrit E Beekhuis

A process is described for preparing N-substituted pyrrolidones from succinonitriles by hydrogenation and hydrolysis.

Process for the preparation of N-substituted 2-pyrrolidones

2-PYRROLIDONE OR A SUBSTITUTED 2-PYRROLIDONE IS PREPARED IN HIGH YIELDS BY HYDROGENATING SUCCINONITRILE, OR AN ALKYL-SUBSTITUTED SUCCINONITRILE, AT 50.degree.-200.degree. C. in the liquid phase, in the presence of ammonia and with a partial hydrogen pressure of about 1-50 atmospheres, then the reaction mixture is contacted with water at 100.degree.-300.degree. C. and the desired product recovered.

Process for preparing 2-pyrrolidones

The novel compound 2-(N-.gamma.-cyanopropyl)-amino-.DELTA..sup.1 -pyrroline is prepared by heating .gamma.-amino-butyronitrile in an inert atmosphere to a temperature up to 250.degree. C. and optionally in the presence of a solvent. The product may be hydrolyzed into pyrrolidone-2 and then polymerized to nylon-4.

Preparation of a 2-amino-pyrroline derivative

Pyrrolidone-2, or N-substituted derivatives thereof, is prepared by heating an aqueous solution of the corresponding 2-amino-.DELTA. .sup.1 -pyrroline at a temperature of 90.degree.-290.degree. C. The process does not require the use of a Raney nickel catalyst and produces the pyrrolidone-2 product in substantial yields.

Process for the preparation of pyrrolidone-2

The compounds ##EQU1## wherein each of R.sub.1 and R.sub.2 is H or alkyl of 1 to 5 carbon atoms, a cycloalkyl group of 5 to 10 carbon atoms or R.sub.1 and R.sub.2 bonded together through two adjacent carbon atoms form a saturated cycloaliphatic ring of 5 to 12 carbon atoms, are prepared by step (1) reacting acrylonitrile with isobutyraldehyde in the liquid phase to form 2,2-dimethyl-4-cyanobutyraldehyde and step (2) by reacting 2,2-dimethyl-4-cyanobutyraldehyde with a carbonyl compound of the general formula ##EQU2## wherein R.sub.1 and R.sub.2 are as defined above, wherein step (a) and step (b) are undertaken in the presence of a catalyst which is piperidine or a primary amine and/or a Schiff base and in the presence of an acid compound.

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Sittard, Netherlands

Leonardus H Geurts