Patent GB-763455-A (GB)
Title: Improvements in addition compounds of amines and halides of aluminium and boron
IPC: C07F5/06
Filed: 1953-10-12
Abstract: The invention comprises as new products stable compounds having the general formula [(R1)(R2)(R3)N]n.EX3 in which R1 is a straight chain alkyl, alkenyl or alkadienyl radical having from 12 to 18 carbon atoms with a terminal carbon atom of the chain attached to the nitrogen atom, R2 and R3 are selected from hydrogen, alkyl radicals containing 1-5 carbon atoms, and the cyclohexyl, phenyl and benzyl radicals, E is aluminium or boron, X is chlorine, bromine, or iodine and n is an integer from 1 to 4, or X is fluorine, E is boron and n is an integer from 1 to 3.  The radical R1 may be n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, 9-octadecenyl, hexadecenyl, tetradecenyl, trans-9-octadecenyl or 9-12 octadecadienyl.  Specified C1-C5 alkyl radicals are methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl and n-amyl. The addition compounds may be obtained by simply contacting the amine with the halide in the presence or absence of an inert solvent such as benzene, toluene, ether, ethyl acetate, cyclohexane or dioxane.  When boron trifluoride is used the reaction may be effected by using gaseous boron trifluoride, the ether-boron trifluoride complex, or the boron trifluoride complex with ethyl acetate or dioxane.  The addition compounds may be purified by precipitation from solution in an organic solvent.  Examples are given for the production of complexes of aluminium chloride with two and four molecular proportions of monolauryl amine; of boron trichloride with one, two, three and four molecular proportions of monolauryl amine and with four molecular proportions of mixed coconut oil monoamines and monostearyl amine respectively; of aluminium bromide, aluminium iodide boron tri-iodide and boron tribromide respectively with four molecular proportions of monolauryl amine, and of boron fluoride with one, two and three molecular proportions of monolauryl amine, one, two and three molecular proportions of monocetyl amine and with 1 molecular proportion of 9-octadecenyl dimethyl amine.  Other amines specified are mono-tetradecyl amine, lauryldimethylamine, cetyldiethylamine and cetyl dimethylamine.  The complexes formed by the addition of one mol. of the amine to one mol. of the halide are soluble in various solvents, e.g. ethyl acetate, benzene, toluene, alcohol, ether and dioxane and the solutions are stated to be valuable antiseptics, fungicides, larvicides and bactericides.  The products are soluble in water and are useful detergents, wetting agents, and emulsifying agents.  They may also be used as finishing agents for textiles, e.g. cotton and cellulose acetate.  Specification 645,425 is referred to.ALSO:Compounds having the general formula [(R1)(R2)(R3)N]nEX3 in which R1 is a straight chain alkyl, alkenyl, or alkadienyl radical having from 12 to 18 carbon atoms with a terminal carbon atom of the chain attached to the nitrogen atom, R2 and R3 are selected from hydrogen, alkyl radicals containing 1 to 5 carbon atoms, E is aluminium or boron, X is chlorine, bromine or iodine, and n is an integar from 1 to 4, or X is fluorine, E is boron and n is an integar from 1 to 3 (see Group IV(b)) can be incorporated directly into paints and lacquers where they function as spreading agents and retard the growth of fungi. Specification 645,425 is referred to.  Aluminium triiodide is obtained by heating iodine to 180 DEG C. and dropping small pieces of aluminium ribbon into the molten iodine while maintaining a blanket of carbon dioxide over the mixture which is then cooled and heated to volatilise the remaining iodine.  Boron triiodide and aluminium fluoride are obtained by adding boron trofluoride to molten aluminium triiodide at 190 DEG C. in a flask fitted with a condenser, thermometer and gas inlet tube.ALSO:Compounds having the general formula [(R1) (R2) (R3) N]n-EX3 in which R1 is a straight chain alkyl, alkenyl, or alkadienyl radical having from 12 to 18 carbon atoms with a terminal carbon atom of the chain attached to the nitrogen atom, R2 and R3 are selected from hydrogen, alkyl radicals containing 1 to 5 carbon atoms, and the cyclohexyl, phenyl, and benzyl radicals, E is aluminium or boron, X is chlorine, bromine, or iodine, and n is an integer from 1 to 4, or X is fluorine, E is boron and n is an integer from 1 to 3 (see Group IV (b) are stated to be useful as antiseptics larvicides and insecticides, and also as anti-perspirants, e.g. when contained in a non-ionic cream base, alcohol, or lanolin. The compounds containing one molecule of the halide are soluble in various organic solvents, e.g. ethyl acetate, benzene, toluene, alcohol, ether, or dioxane and the solutions may be used an antiseptics, fungicides, larvicides and bactericides. Specification 645,425, [Group III], is referred to.