Method for producing hydrolysis-stable ammonium nitriles

1. A method for producing an hydrolysis-stable ammonium nitrile comprising reacting

a first compound of the formula 1

 in which R 1 , R 2 , R 3 are identical or different and are linear or branched C 1 –C 24 -alkyl groups, C 2 –C 24 -alkenyl groups or are C 1 –C 4 -alkoxy-C 1 –C 4 -alkyl groups, substituted or unsubstituted benzyl, or in which R 1 and R 2 together with the nitrogen atom to which they are bonded form a ring having 4 to 6 carbon atoms, which may be substituted by C 1 –C 5 -alkyl, C 1 –C 5 -alkoxy, C 1 –C 5 -alkanoyl, phenyl, amino, ammonium, cyano, cyanamino, chlorine or bromine and which can contain in addition to the nitrogen atom, instead of carbon atoms, one or two oxygen or nitrogen atoms, a group N—R 6 or a group R 3 —N—R 6 , in which R 6 is hydrogen, C 1 - to C 5 -alkyl, C 2 - to C 5 -alkenyl, C 2 –C 5 -alkynyl, phenyl, C 7 –C 9 -aralkyl, C 5 –C 7 -cycloalkyl, C 1 –C 6 -alkanoyl, cyanomethyl or cyano, R 4 and R 5 are hydrogen, C 1 –C 4 -alkyl, C 1 –C 4 -alkenyl, C 1 –C 4 -alkoxy-C 1 –C 4 -alkyl, phenyl or C 1 –C 3 -alkylphenyl, preferably hydrogen, methyl or phenyl, where in particular R 4 is hydrogen if R 5 is not hydrogen, and A is an anion,

with a second compound of the formulae RSO 3 X, R 7 SO 4 X or R 8 CO 2 X, where R, R 7 and R 8 are C 4 –C 20 -alkyl or substituted aryl and X is an alkali metal ion, ammonium ion or hydrogen ion, in the presence of water at elevated temperature.

2. The method as claimed in claim 1 , where A is selected from the group consisting of chloride, bromide, iodide, fluoride, sulfate, hydrogen sulfate, carbonate, hydrogen carbonate, phosphate, mono- and dihydrogen phosphate, pyrophosphate, metaphosphate, nitrate, methylsulfate, phosphonate, methylphosphonate, methanedisulfonate, methylsulfonate, ethanesulfonate, and mixtures thereof.

3. The method of claim 1 , wherein the second compound is an alkali metal salt or ammonium salt of a compound selected from the group consisting of p-toluenesulfonate, dodecylbenzenesulfonate, C 8 –C 18 -ether sulfate, sodium sulfate, C 8 –C 18 -alkylcarboxylate, and the mixtures thereof.

4. The method of claim 1 , wherein the second compound is an alkali metal salt or ammonium salt of cumenesulfonate.

5. The method of claim 1 , wherein the second compound is an alkali metal salt or ammonium salt of lauryl sulfate and/or C 8 –C 18 -alcohol sulfate.

6. The method of claim 1 , wherein the elevated temperature is 50 to 100° C.

7. The method of claim 1 , in which the first compound is dissolved in water, and reacted with an aqueous solution of the second compound in a molar ratio of the second compound to the first compound ranging from 1:2 to 5:1 to form a reaction mixture.

8. The method of claim 7 , further comprising cooling the reaction mixture to precipitate the hydrolysis-stable ammonium nitrile.

9. The method of claim 7 , further comprising spray-drying the reaction mixture to recover the hydrolysis-stable ammonium nitrile.

10. The method of claim 9 , further comprising granulating the hydrolysis-stable ammonium nitrile into granules and coating the granules with a coating substance.

11. The method of claim 1 , wherein with reference to the second component R, R 7 and R 8 are C 10 –C 18 -alkyl or C 1 –C 18 -alkylphenyl.

12. The method of claim 1 , wherein R4 and R5 are hydrogen, methyl, or phenyl.

13. The method of claim 7 , wherein the molar ratio of the second compound to the first compound ranges from 1.1 to 4:1.