Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Patent
1997-03-03
1998-06-09
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
558371, 558378, 558388, 558389, 558390, 558408, 564282, 564291, 564296, C07C20960, C07C21108, C07C25503, C07C25533
Patent
active
057636397
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/03273 of Aug. 17, 1995.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an improved process for preparing quaternized glycine nitriles of the general formula I ##STR2## where R.sup.1 and R.sup.2 can be identical or different and are each an aliphatic, cycloaliphatic or araliphatic radical having from 1 to 30 carbon atoms, with R.sup.1 and R.sup.2 also being able to form, together with the nitrogen atom to which they are bound, a saturated or unsaturated five-membered or six-membered heterocyclic ring which can additionally contain further hetero atoms, can be benzo-fused and can bear alkyl side groups, and furthermore R.sup.2 can also be hydrogen, by one or more non-adjacent oxygen atoms, or a radical of the formula ##STR3## where R.sup.5 is a chemical bond or a C.sub.1 - to C.sub.6 -alkylene bridge, and ##STR4## where the variables R.sup.1 and R.sup.2 are as defined above, with a monoaldehyde of the general formula IIIa or a dialdehyde of the general formula IIIb C.sub.20 -alkyl, and hydrocyanic acid or an alkali metal cyanide in aqueous medium and subsequent quaternization with an alkylating agent of the general formula IV
2. Discussion of the Background
The patents U.S. Pat. Nos. 5,236,616 (1) and 5,281,361 (2) disclose cationic nitriles containing, for example, the structural unit ##STR5##
Cationic nitriles, e.g. (CH.sub.3).sub.3 N.sup..sym. --CH.sub.2 CN Cl.sup..crclbar., are presented there as extremely hygroscopic, i.e. water-sensitive substances, which rapidly take up water from the air and can easily hydrolyze to give corresponding amides. Cationic nitriles are therefore generally (prepared in anhydrous organic solvents, e.g. in dry acetonitrile (cf. Example 1(i) of (1)).
SUMMARY OF THE INVENTION
It is an object of the present invention to provide a preparation process for cationic nitriles or formulations thereof, which gives products which do not have such water sensitivity.
We have found that this object is achieved by the process defined in the introduction, wherein the reaction of the amines II with the aldehydes III and hydrocyanic acid or alkali metal cyanide and the quaternization are carried out successively in aqueous medium without isolation of an intermediate.
This gives aqueous solutions of the quaternized glycine nitriles I described, which have virtually unlimited stability under usual conditions, i.e. are not sensitive to hydrolysis. When storing the aqueous solutions of the quaternized glycine nitriles I prepared according to the invention, usually no hydrolysis products are found even after a period of several weeks at temperatures of up to 40.degree. C.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The unquaternized glycine nitrile I precursors, which are not isolated or even purified in the process of the invention, and their preparation are known in principle from the patents DE-A 25 03 582 (3), DE-A 25 55 769 (4) and DE-A 26 20 445 (5).
The radicals R.sup.1 and R.sup.2 are each preferably C.sub.1 - to C.sub.18 -alkyl, particularly preferably C.sub.2 - to C.sub.10 -alkyl, more preferably C.sub.3 - to C.sub.10 -cycloalkyl, especially C.sub.5 - to C.sub.7 -cycloalkyl, or furthermore, in particular, araliphatic radicals having from 7 to 20 carbon atoms, especially phenylalkyl having from 7 to 12 carbon atoms.
Suitable heterocyclic ring structures containing R.sup.1 and R.sup.2 are, in particular, those which contain, besides the nitrogen atom of the glycine moiety, no, one or two further hetero atoms from the group consisting of nitrogen or oxygen. The heterocyclic rings preferably bear no, one or two fused benzene rings. If additional alkyl side groups are present, these are preferably C.sub.1 - to C.sub.4 -alkyl, in particular methyl or ethyl.
In accordance with the specified meanings of R.sup.1 and R.sup.2, the following primary or secondary amines II can be used with particularly good results as starting compounds in the process of the invention:
methylamine, ethylamine, n-propylamine, i
REFERENCES:
patent: 4022815 (1977-05-01), Schlecht et al.
patent: 4113764 (1978-09-01), Distler et al.
patent: 4134889 (1979-01-01), Distler et al.
The Journal of the American Chemical Society, vol. LV1, Jul.-Dec. 1934, Editor Arthur B. Lamb.
Annen Ulrich
Muller Reinhard
Seelmann-Eggebert Hans-Peter
Widder Rudi
BASF - Aktiengesellschaft
Oswecki Jane C.
Richter Johann
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