Patent GB-1012796-A (GB)
Title: Substituted aminophosphonium compounds
IPC: C10L1/26
Filed: 1962-06-19
Abstract: Petrol and lubricating oils contain as additives useful as lead scavengers and antioxidants aminophosphonium compounds of the general formula <FORM:1012796/C4-C5/1> wherein n is 1 or 2, R1 and R11 are the same or different and are hydrogen, alkyl, alkenyl, aryl, alkylaryl or cycloalkyl (provided that R1 and R11 are not both hydrogen) or R1 and R11 taken together represent alkylene or a dialkylene ether radical, R111 is alkyl, alkanyl, phenyl, halophenyl, alkylphenyl or halophenyl alkyl, R when n is 1 is alkyl, phenylalkyl, diphenyl alkyl, or mono- or di-halogenated phenylalkyl, phenyldiazonium or halotriazinyl, or when n is 2 R is alkylene, alkenylene, alkylene-aralkylene, alkylenetetraalkyldisiloxanyl alkylene or a dialkylene ether radical and A- is an anion, provided that where A- is iodine and n is 1 not more than three of R1, R11, R111 and R are methyl (see Division C2).  The anion A-may be Cl, Br, I, F, borohydride, picrate or hexafluorophosphate.ALSO:The invention comprises inter alia substituted amino phosphonium compounds of the general formula <FORM:1012796/C3/1> wherein n is 2, R1 and R11 are the same or different and are hydrogen, alkyl, alkenyl, aryl, alkylaryl or cycloalkyl (provided that R1 and R11 are not both hydrogen) or R1 and R11 taken together represent alkylene or a dialkylene ether radical, R111 is alkyl, alkenyl, phenyl, halophenyl, alkylphenyl, or halophenylalkyl, R is alkylenetetralkyl disiloxanylalkylene, and A- is an anion, e.g. Cl, Br, I, F, borohydride, picrate or hexafluorophosphate. The products wherein A is halogen may be obtained by reacting an organic halide RXn with an aminophosphine of the formula <FORM:1012796/C3/2> wherein X is halogen and the other symbols are as defined above. The reaction is preferably carried out in the presence of an inert solvent, e.g. dimethylformamide, benzene, toluene, xylene or diethyl ether and preferred reaction temperatures are from 35 DEG  to 200 DEG  C.  The halide anion X may be replaced by other anions such as borohydride, picrate or hexafluorophosphate by adding a solution of the aminophosphonium halide to a saturated solution of a salt containing the desired anion.  An example is given for the production of the compound of the formula <FORM:1012796/C3/3> The products are useful as lead scavengers and antioxidants for petrol and lubricating oils and as plant growth retardants, nematocides, and intermediates for polymers.ALSO:The invention comprises substituted amino-phosphonium compounds of the general formula:- <FORM:1012796/C2/1> wherein n is 1 or 2, R1 and R11 are the same or different and are hydrogen, alkyl, alkenyl, aryl, alkylaryl or cycloalkyl (provided that R1 and R11 are not both hydrogen) or R1 and R11 taken together represent alkylene or a dialkylene ether radical, R111 is alkyl, alkenyl, phenyl, halophenyl, alkylphenyl or halophenyl-alkyl; R, where n is 1, is alkyl, phenylalkyl, diphenylalkyl, mono- or di-halophenylalkyl, phenyl-diazonium or halotriazinyl, or where n is 2 R is alkylene, alkenylene, alkylene - aralkylene, alkylenetetraalkyldisiloxanylalkylene or a dialkylene ether radical and A- is an anion provided that when A- is iodine and n is 1 not more than three of R1, R11, R111 and R are methyl.  The anion A- may be Cl, Br, I, F, borohydride, picrate or hexafluorophosphate. Preferred compounds are those in which R1 is hydrogen or an alkyl radical of up to 4 C atoms, R11 is an alkyl group of up to 4 C atoms, especially t.-butyl, R111 is phenyl and when n is 1 R is alkyl of up to 4 C atoms, benzyl, halobenzyl, or halotriazinyl or when n is 2, R is alkylene or alkenylene of up to 4 carbon atoms, xylylene, alkyl-substituted xylylene (e.g. tetramethyl-p-xylylene), di-alkylene ether having alkylene substituents of 2 to 4 carbon atoms, 9,10-anthracenylene-dimethylene or alkylene-tetraalkyldisiloxanyl alkylene wherein the alkyl and alkylene groups have 1 to 4 carbon atoms.  The products wherein A- is halogen may be obtained by reacting an organic halide RXn with an aminophosphine of the formula <FORM:1012796/C2/2> wherein X is halogen and the other symbols are as defined above. The reaction is preferably carried out in the presence of an inert solvent, e.g. dimethylformamide, benzene, toluene, xylene or diethyl ether, and preferred reaction temperatures are from 35 DEG to 200 DEG  C. The halide anion X may be replaced by other anions such as borohydride, picrate or hexafluorophosphate by adding a solution of the amino-phosphonium halide to a saturated solution of a salt containing the desired anion. Several examples are given and the products are useful as lead scavengers and antioxidants for petrol and lubricating oils and as plant growth retardants, nematocides and intermediates for polymers.