Patent GB-830800-A (GB)
Title: Amidophosphoric acid derivatives
IPC: C07F9/22
Filed: 1957-04-04
Abstract: Lubricating oil compositions comprise as high-pressure and anti-ageing additives amidophosphoric acid derivatives of the general formula <FORM:0830800/III/1> wherein X represents oxygen or sulphur, Y1 and Y2 represent a hydrocarbon radical which may be saturated or unsaturated, aliphatic, cycloaliphatic, aryl or aralkyl and may be substituted e.g. by halogen, or Y1 may be hydrogen or Y1 and Y2 together with the nitrogen atom form a heterocyclic radical, e.g. an ethyleneimine, pyrrolidine, piperidine, hexamethyleneimine or morpholine radical, and n denotes any integer.  The lubricating oils may be mineral or synthetic in origin, suitable synthetic oils being polyether, polyester or poly-ether-ester oils.  A specific polyether oil mentioned is one based on tetrahydrofurane and ethylene oxide.ALSO:The invention comprises amidophosphoric acid derivatives of the general formula <FORM:0830800/IV (b)/1> wherein X represents oxygen or sulphur, Y1 and Y2 represent a hydrocarbon radical which may be saturated or unsaturated, aliphatic, cycloaliphatic, aryl or aralkyl and may be substituted, e.g. by halogen, or Y1 may be hydrogen or Y1 and Y2 together with the nitrogen atom form a heterocyclic radical, e.g. an ethyleneimine, pyrrolidine, piperidine, hexamethyleneimine or morpholine radical, and n denotes any integer. They are prepared by reacting ammonia with an amidophosphoric acid halide of the general formula <FORM:0830800/IV (b)/2> wherein Z1 and Z2 represent the same or different halogen atoms at room temperature or with cooling, preferably in an inert solvent, e.g. carbon tetrachloride, benzene, chlorobenzene, ethyl acetate or ether.  The products are used in fireproofing compositions and as lubricant additives.  In examples there are prepared by the action of dry ammonia gas on the appropriate amidophosphoric acid halide in solution in benzene, carbon tetrachloride or methylene chloride: (1) a mixture of monomeric N-diethylamidophosphoric acid diamide and the polymers formed therefrom by the splitting out of ammonia from N-diethylamidophosphoric acid chloride; (2) monomeric N-di-n-butyl-amidophosphoric acid diamide mixed with polymers thereof from N-di-n-butylamido-phosphoric acid diamide mixed with polymers thereof from N - di - n - butylamido - phosphoric acid dichloride; (3) N-morpholidophosphoric acid diamide from N-morpholidophosphoric acid dichloride; (4) N-piperidyl-phosphoric acid diamide from N-piperyl-phosphoric acid dichloride; (5) N-b -chlorethylamido-phosphoric acid diamide mixed with ammonium chloride from N-b -chlorethylamidophosphoric acid dichloride; (6) N-dimethylamidophosphoric acid diamide mixed with NH4Cl from N-dimethylamidophosphoric acid dichloride; (7) diethylamidothiophosphoric acid diamide from diethylamidothiophosphoric acid dichloride; (8) dipropylamidothiophosphoric acid diamide mixed with polymers thereof from dipropylamidothiophosphoric acid dichloride; (9) tert.-octylamidothiophosphoric acid diamide mixed with polymers thereof from tert.-octylamidothiophosphoric acid dichloride, obtainable by reacting tert.-octylamine with phosphorus sulphochloride in methylene chloride; (10) morpholidothiophosphoric acid diamide from morpholidothiophosphoric acid dichloride obtainable from morpholine and PSCl3; (11) N-methylbenzylamidothiophosphoric acid diamide from N-methylbenzylamidothiophosphoric acid dichloride, obtainable from N-methylbenzylamide and PSCl3.ALSO:The invention comprises amidophosphoric acid derivatives of the general formula <FORM:0830800/IV (a)/1> wherein X represents oxygen or sulphur, Y1 and Y2 represent a hydrocarbon radical which may be saturated or unsaturated, aliphatic, cycloaliphatic, aryl or aralkyl and may be substituted, e.g. by halogen, or Y1 may be hydrogen or Y1 and Y2 together with the nitrogen atom form a heterocyclic radical, e.g. an ethyleneimine, pyrrolidine, piperidine, hexamethyleneimine or morpholine radical, and n denotes any integer.  They are prepared by reacting ammonia with an amidophosphoric acid halide of the general formula <FORM:0830800/IV (a)/2> wherein Z1 and Z2 represent the same or different halogen atoms at room temperature or with cooling, preferably in an inert solvent, e.g. carbon tetrachloride, benzene, chlorobenzene, ethyl acetate or ether.  The products may be incorporated in spinning and casting masses for the production of shaped articles and are used in fireproofing compositions and as lubricant additives.  In examples there are prepared by the action of dry ammonia gas on the appropriate amidophosphoric acid halide in solution in benzene, carbon tetrachloride or methylene chloride; (1) a mixture of monomeric N-diethylamidophosphoric acid diamide and the polymers formed therefrom by the splitting out of ammonia from N-diethylamidophosphoric acid chloride; (2) monomeric N-di-n-butyl-amidophosphoric acid diamide mixed with polymers thereof from N-di-n-butylamido-phosphoric acid dichloride; (8) dipropylamidothiophosphoric acid diamide mixed with polymers thereof from dipropylamidothiophosphoric acid dichloride; (9) tert.-octylamidothiophosphoric acid diamide mixed with polymers thereof from tert.-octylamidothiophosphoric acid dichloride, obtainable by reacting tert.-octylamine with phosphorus sulphochloride in methylene chloride.