Patent GB-672708-A (GB)
Title: New quaternary ammonium salts and processes for making the same
Inventor: BARBER HARRY JAMES
Filed: 1949-05-25
Abstract: The invention comprises quaternary salts of the formula R(XCH2N+R1R2R3A-)n where X is O or S, R is aryl, R1 is alkyl, aralkyl or cycloalkyl, R2 and R3 are alkyl (1-4 carbon atoms), A is an inorganic or organic anion and n is 1 or 2; alternatively R1R2R3 and N may be the residue of a heterocyclic tertiary base such as pyridine or quinoline.  These salts may be prepared by reacting halides R(XCH2Y)n, where Y is chlorine or bromine, with tertiary amines NR1R2R3, and if desired converting the resulting quaternary halides into other salts by known methods, e.g. double decomposition.  A solvent may be used for the reaction and the temperature should be kept below 50 DEG  C.  R is preferably phenyl or naphthyl and may be substituted with cyano, nitro, halogen, alkyl or alkoxy groups (1-12 carbon atoms); R1, R2 and R3 may also carry inert substituents.  In the examples, the following are prepared: (1) aryloxymethyldimethyl-benzyl-ammonium chlorides where aryl is phenyl, p-cyanophenyl, o- and p-nitrophenyl, p-bromophenyl, o- and p-chlorophenyl, 2 : 4-, 2 : 5-, 3 : 4- and 3 : 5-dichlorophenyl, 2 : 3 : 4- and 2 : 4 : 5-trichlorophenyl, o- and m - methyl - p - chlorophenyl, p - methyl - o-chlorophenyl, 3 : 5 - dimethyl - 4 - chlorophenyl and a - and b -naphthyl; also p-phenylene bis - (oxymethyl - dimethyl - benzyl - ammonium chloride); (2) aryloxymethyl-dimethyl-benzyl-ammonium picrates, where aryl is p-tolyl, p-anisyl, p-tert.-octylphenyl, m-chlorophenyl, m-chloro-p-methylphenyl and p-chloro-o- and m-anisyl; (3) o-chlorophenoxy-, 2 : 4-dichlorophenoxy- and b -naphthoxy-methyl-triethyl-ammonium chlorides; (4) p-anisyloxymethyl - trimethyl - ammonium picrate, which is reconverted into the chloride; (5) p-nitrophenoxy-, 2 : 4-dichlorophenoxy-and 3-methyl-4 - chlorophenoxy - methyl - pyridinium chlorides; (6) 2 : 4-dichlorophenoxymethyl-quinolinium chloride; (7) 3 : 5-dimethyl-4-chlorophenoxymethyl - dimethyl - alkyl - ammonium chlorides, where alkyl is n-amyl, n-hexyl, isooctyl, n-decyl, lauryl, cetyl and stearyl; (8) 2 : 4 - dichloro - phenoxymethyl - dimethyl-alkyl-ammonium chlorides, where alkyl is n-octyl, n-decyl and stearyl; (9) o-nitro-p-chlorophenoxymethyl - dimethyl - n - octyl - ammonium chloride; (10) 3 : 5-dimethyl-4-chlorophenoxymethyl - dimethyl - cyclo - octyl-ammonium chloride; (11) p-phenylene bis-(oxymethyl - dimethyl - alkyl - ammonium chlorides), where alkyl is n-amyl, n-hexyl, n-octyl and stearyl; (12) 4-chloro- and 2 : 5-dichloro - phenylthiomethyl - dimethyl - n-octyl- and n-decyl-ammonium chlorides; (13) p-chloro-, p-methyl-, 2 : 4-, 3 : 4- and 2 : 5-dichloro - phenylthiomethyl - dimethyl - benzyl-ammonium chlorides, and the picrate of the last named.  The Provisional Specification refers also to compounds of the above general formula where R is aralkyl (X = S only).  A further method is given of preparing the quaternary salts, viz. reaction of NR1R2R3 with R(XCH2SO3Z)n, where Z is alkyl, aryl, aralkyl or cycloalkyl; this gives a quaternary ammonium sulphonate which may if desired be converted into other salts.  It is also stated that n may be 2.  The aryloxymethyl and arylthiomethyl halides may be made as in Specification 647,215.  Specification 434,602 also is referred to.