Verfahren zur Herstellung von Oximphosphaten

The invention comprises an O-organo iminyl phosphate containing the fundamental grouping: and an O-organo iminyl thionophosphate containing the fundamental grouping: Specified compounds of this type are those having the general formula (R1)(R2)P(X).O.N = A, wherein R1 and R2 are alkoxy, alkylthio, or alkylamino radicals, A is a carbocyclic or a =C(R3)(R4) radical in which R3 is hydrogen or an organic radical and R4 is an organic or inorganic radical, and X is oxygen or sulphur. The organic radicals R3 and/or R4 may be heterocyclic, aromatic, acyclic or alicylic. Also, where R1 and R2 are alkoxy radicals they should preferably contain from 1 to 5 carbon atoms. The compounds may be obtained by condensing an oxime or metal salt of an oxime with a halophosphate or halothionophosphate in accordance with the equation: wherein Y is hydrogen or a metal, e.g. an alkali metal. When a metal salt of the oxime is used the reaction is preferably conducted in a non-aqueous system and preferably in the presence of an inert solvent such as petroleum ether, benzene, toluene or cyclohexane, and at a reaction temperature between about 0 DEG C. and 120 DEG C. The free oxime may be reacted with the halophosphate in the presence of a hydrogen halide sequestering agent such as pyridine or an acid binding agent such as sodium carbonate. The latter process also may be carried out in the presence of an inert solvent and in a nonaqueous system and a catalyst such as metallic copper and/or potassium bromide may be present. Examples are given for the production of (1) O,O-diethyl-O-propyliden-2-iminyl phosphate from diethylchlorophosphate and the sodium salt of acetoxime; (2) O,O-diethyl-O-propyliden-2-iminyl thionophosphate from diethylchlorothionophosphate and the sodium salt of acetoxime; (3) the same product as in (1) by refluxing acetoxime with diethylchlorophosphate in the presence of pyridine and benzene; (4) the same product as in (2) by heating a solution of acetoxime in dry toluene with diethylchlorothionophosphate in the presence of sodium carbonate and a small amount of metallic copper; (5) O,O - dimethyl - O - propyliden - 2-iminyl phosphate from the sodium salt of acetoxime and dimethylchlorophosphate; (6) N,N,N1,N1 - tetramethyldiamido - O - propyliden - 2 - iminyl phosphate from tetramethyldiamidochlorophosphate and the sodium salt of acetoxime; (7) O,O-diethyl-O-(4 - methyl - 3 - pentenyliden - 2 -