.alpha.-iminodiacetonitriles and their preparation
AssigneeBASF SE
InventorsFritz Brunnmueller, Michael Kroener
Life of this patent
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Abstract
Novel .alpha.-iminodiacetonitriles are prepared by a process in which an aldehyde-cyanohydrin or a haloacetonitrile is reacted with an aminonitrile, the reaction being carried out in the presence of a lower alkanol in the case of the preparation of symmetric .alpha.-iminodiacetonitriles, and in the presence of an auxiliary base in the case of the preparation employing a haloacetonitrile. The .alpha.-iminodiacetonitriles obtainable by the process of the invention are useful starting materials for the preparation of dyes, fungicides, bactericides, herbicides, textile assistants, anticorrosion agents, complex-forming agents, stabilizers in electroplating baths and inhibitors for antifreezes.
Claims15
An .alpha.-iminodiacetonitrile of the formula ##STR21## where the individual radicals R.sup.1 and R.sup.2 are different and each is selected form the group consisting of:
- hydrogen;
- alkyl of 1 to 20 carbon atoms and said alkyl substituted by alkoxy or alkylthio, each of 1 to 4 carbon atoms, halogen, carboxamido or cyano;
- alkenyl of 2 to 20 carbon atoms;
- cycloalkyl of 5 to 8 carbon atoms;
- aralkyl or alkylaryl of 7 to 12 carbon atoms;
- and
- phenyl.
An .alpha.-iminodiacetonitrile of the formula ##STR22## where the individual radicals R.sup.1 and R.sup.2 are identical and are selected from the group consisting of:
- methyl which is substituted by alkoxy or alkylthio, each of 1 to 4 carbon atoms;
- cycloalkyl of 5 to 8 carbon atoms;
- and
- phenyl.
A process for the preparation of an asymmetric .alpha.-iminodiacetonitrile of the formula ##STR23## where the individual radicals R.sup.1 and R.sup.2 are different and each is selected form the group consisting of:
- hydrogen;
- alkyl of 1 to 20 carbon atoms and said alkyl substituted by alkoxy or alkylthio, each of 1 to 4 carbon atoms, halogen, carboxamido or cyano;
- alkenyl of 2 to 20 carbon atoms;
- cycloalkyl of 5 to 8 carbon atoms;
- aralkyl or alkylaryl of 7 to 12 carbon atoms;
- and
- phenyl,
- which process comprises:
- reacting an aldehyde-cyanohydrin of the formula ##STR24## where R.sup.1 has the above meanings, with an aminonitrile of the formula ##STR25## where R.sup.2 has the above meanings but differs from R.sup.1.
A process for the preparation of a symmetric .alpha.-iminodiacetonitrile of the formula ##STR26## where the individual radicals R.sup.1 and R.sup.2 are identical and are selected from the group consisting of
- methyl which is substituted by alkoxy or alkylthio, each of 1 to 4 carbon atoms;
- cycloalkyl of 5 to 8 carbon atoms;
- and
- phenyl,
- which process comprises:
- reacting an aldehyde-cyanohydrin of the formula ##STR27## where R.sup.1 has the above meanings with an aminonitrile of the formula ##STR28## where R.sup.2 has the above meanings and is identical to R.sup.1, in the presence of a lower alkanol, using from 5 to 95% by weight, based on the amount of lower alkanol, of the starting material III.
A process for the preparation of an .alpha.-iminodiacetonitrile of the formula ##STR29## where R.sup.1 is phenyl and R.sup.2 is selected from the group consisting of
- hydrogen,
- alkyl of 1 to 20 carbon atoms or said alkyl substituted by alkoxy or alkylthio, each of 1 to 4 carbon atoms, halogen, carboxamido or cyano,
- alkenyl of 2 to 20 carbon atoms,
- cycloalkyl of 5 to 8 carbon atoms,
- aralkyl or alkylaryl of 7 to 12 carbon atoms, and
- phenyl,
- which process comprises:
- reacting a haloacetonitrile of the formula ##STR30## where R.sup.1 has the above meanings and X is halogen, with an aminonitrile of the formula ##STR31## where R.sup.2 has the above meanings, in the presence of an auxiliary base selected from the group consisting of
- a tertiary amine;
- an alkali metal hydroxide and
- an alkali metal carbonate, and also in the presence of an organic solvent.
Dependencies are inferred from the claim text.