Patent GB-434602-A (GB)
Title: The manufacture and application of new quaternary ammonium compounds
Filed: 1934-03-05
Abstract: Aromatic compounds substituted by a quaternary aminoalkyl group and by a saturated or unsaturated alkyl, cycloalkyl, aryl or aralkyl group, one substituent being linked to the aromatic nucleus through an atom of oxygen and the other through an atom of oxygen, nitrogen or sulphur, are prepared (1) from a reactive ester of a saturated or unsaturated alkyl or aralkyl alcohol and an aromatic compound substituted by a tertiary aminoalkyl group and by a saturated or unsaturated alkyl, cycloalkyl, aryl or aralkyl group, the substituents being linked to the aromatic nucleus as described above, or (2) from a tertiary amine and an aromatic compound substituted by a saturated or unsaturated alkyl, cycloalkyl, aryl or aralkyl group and by an alkyl group carrying a halogen atom, a sulphuric ester group or other replaceable substituent, the substituents being linked to the aromatic nucleus as described above, or (3) from a reactive ester of a saturated or unsaturated aliphatic, cycloaliphatic, or aralkyl alcohol and a primary aromatic amine substituted in the nucleus by a quaternary aminoalkoxy group.  The products may contain additional substituents such as halogen atoms or alkyl, cycloalkyl, hydroxy or nitro groups.  Examples are given of the preparation of (1) N-diethyl-N-benzyl-N-3-methoxyphenoxyethyl-ammonium chloride from benzyl chloride and 3 - methoxyphenyl - b  - diethylaminoethyl ether (obtainable from sodium 3-methoxyphenolate and diethylaminoethyl chloride); (2) N - diethyl - N - benzyl - N - 3 - butyloxy-phenoxyethylammonium chloride from benzyl chloride and 3 - butyloxyphenyl - b  - diethylaminoethyl ether (obtainable from sodium 3-butyloxyphenolate and diethylaminoethyl chloride); (3) N - diethyl - N - benzyl - N - 3 - cyclohexyloxyphenoxyethylammonium chloride from benzyl chloride and 3-cyclohexyloxyphenyl-b -diethylaminoethyl ether (obtainable from sodium 3 - cyclohexyloxyphenolate and diethylaminoethyl chloride); (4) N - diethyl - N - benzyl - N - 3 - n - octyloxyphenoxyethyl-ammonium chloride from benzyl chloride and 3 - n - octyloxyphenyl - b  - diethylaminoethyl ether (obtainable from sodium 3-n-octyloxyphenolate and diethylaminoethyl chloride); (5) N - diethyl - N - allyl - N - 3 - n - octyloxyphenoxyethylammonium bromide from allyl bromide and 3 - n - octyloxyphenyl -b  - diethylaminoethyl ether; (6) N-diethyl-N-benzyl-N-2-n-octyloxyphenoxyethylammonium chloride from benzyl chloride and 2-n-octyloxyphenylb -diethylaminoethyl ether (obtainable from sodium 2-n-octyloxyphenolate and diethylaminoethyl chloride); (7) N-diethyl-N-benzyl-N-4-n-octyloxyphenoxyethylammonium chloride from benzyl chloride and 4-n-octyloxyphenyl-b -diethylaminoethyl ether (obtainable from sodium 4 - n - octyloxyphenolate and diethylaminoethyl chloride); (8) N-diethyl-N-benzyl-N-3-dodecyloxyphenoxyethylammonium chloride from benzyl chloride and 3-dodecyloxyphenyl-b -diethylaminoethyl ether (obtainable from sodium 3-dodecyloxyphenolate and diethylaminoethyl chloride); (9) N-diethyl-N-benzyl-N - 3 - benzyloxyphenoxyethylammonium chloride from benzyl chloride and 3-benzyloxyphenyl - b  - diethylaminoethyl ether (obtainable from sodium 3 - benzyloxyphenolate and diethylaminoethyl chloride); (10) N-diethyl-N - benzyl - N - 3 - o - chlorobenzyloxyphenoxyethylammonium chloride from benzyl chloride and 3 - o - chlorobenzyloxyphenyl - b  - diethylaminoethyl ether (obtainable from sodium 3 - o - chlorobenzyloxyphenolate and diethylaminoethyl chloride); (11) N-diethyl-N - benzyl - N - 3 - benzyloxychlorophenoxyethylammonium chloride from benzyl chloride and 3 - benzyloxychlorophenyl - b  - diethylaminoethyl ether (obtainable from sodium 3 - benzyloxychlorophenolate and diethylaminoethyl chloride; (12) N-diethyl-N-benzyl-N - 2 - methoxy - 6 - allylphenoxyethylammonium chloride from benzyl chloride and 2 - methoxy - 6 - allylphenyl - b  - diethylaminoethyl ether (obtainable from sodium 2-methoxy-6-allylphenolate and diethylaminoethyl chloride); (13) N-diethyl-N-benzyl-N-3-methoxythiophenoxyethylammonium chloride from benzyl chloride and 3-methoxyphenyl-b -diethylaminoethyl thioether (obtainable from sodium 3 - methoxythiophenolate and diethylaminoethyl chloride); (14) N-methyl-N-diethyl-N-3-methoxythiophenoxyethylammonium iodide from methyl iodide and 3-methoxyphenyl-b -diethylaminoethyl thioether; (15) N-diethyl-N-benzyl - N - 3 - n - octyloxythiophenoxyethylammonium chloride from benzyl chloride and 3 - n - octyloxyphenyl - b  - diethylaminoethyl thioether (obtainable from sodium 3-diethylaminothioethoxy - 1 - phenolate and n-octyl bromide); (16) N-diethyl-N-benzyl-N-3-thiooctyloxyphenoxyethylammonium chloride from benzyl chloride and 3-thiooctyloxyphenyl-b -diethylaminoethyl ether (obtainable from sodum 3 - diethylaminoethoxy - 1 - thiophenolate and n-octyl bromide); (17) N-diethyl-N-benzyl-N - 3 - butylaminophenoxyethylammonium chloride from benzyl chloride and 3-butylaminophenyl - b  - diethylaminoethyl ether (obtainable from sodium 3-butylaminophenolate and diethylaminoethyl chloride); (18) N-diethyl-N-benzyl - N - 3 - butylamino - p - cresoxyethylammonium chloride from benzyl chloride and 3 - butylamino - 4 - cresyl - b  - diethylaminoethyl ether (obtainable from sodium 3-butylamino - p - cresolate and diethylaminoethyl chloride); (19) N-methyl-N-diethyl-N-3-butylamino - p - cresoxyethylammonium iodide from methyl iodide and 3-butylamino-4-cresyl-b -diethylaminoethyl ether; (20) N-diethyl-N-benzyl - N - 3 - n - octyloxyphenylaminoethylammonium chloride from benzyl chloride and N - (3 - octyloxyphenyl) - b  - diethylaminoethylamine (obtainable from 3-n-octyloxyaniline and diethylaminoethyl chloride); (21) N-diethyl-N-benzyl - N - 3 - n - octylaminophenoxyethylammonium chloride from benzyl chloride and 3 - n - octylaminophenyl - b  - diethylaminoethyl ether (obtainable from sodium 3-n-octylaminophenolate and diethylaminoethyl chloride); (22) N - diethyl - N - benzyl - N - 1 - hexylamino-3 - naphthyloxyethylammonium chloride from benzyl chloride and 1-hexylamino-3-naphthyl - b  - diethylaminoethyl ether (obtainable from 1 - amino - 3 - diethylaminoethoxynaphthalene and n-hexyl bromide); (23) N-diethyl - N - benzyl - N - 1 - n - octylamino - 3 - naphthyloxyethylammonium chloride from benzyl chloride and 1 - n - octylamino - 3 - naphthyl - b  - diethylaminoethyl ether (obtainable from 1-amino-3-diethylaminoethoxynaphthalene and n-octyl bromide); (24) N-diethyl-N - benzyl - N - p - phenoxyphenylaminoethylammonium chloride from benzyl chloride and p - phenoxy - N - diethylaminoethylaniline (obtainable from p-phenoxyaniline and diethylaminoethyl chloride); (25) N-trimethyl-N-3-butyloxyphenoxyethylammonium bromide from trimethylamine and 1-w-bromoethoxy-3-butyloxybenzene (obtainable from ethylene bromide and the sodium salt of resorcinol monobutyl ether); (26) N-diethyl-N-p-nitrobenzyl-N - 3 - n - octyloxyphenoxyethylammonium, chloride from p-nitrobenzyl chloride and 3-n-octyloxyphenyl - b  - diethylaminoethyl ether; (27) N-diethyl-N -g -p-(hydroxyphenyl) - propylN - 3 - octyloxyphenoxyethylammonium bromide from hydroxyphenylpropyl bromide and 3 - octyloxy - 1 - diethylaminoethoxybenzene (obtainable from sodium 3-octyloxyphenolate and diethylaminoethyl chloride); (28) N-diethyl N-benzyl - N - p - methylaminophenoxyethylammonium chloride from dimethyl sulphate and N - diethyl - N - benzyl - N - p - aminophenoxyethylammonium chloride (obtainable from 4 - nitro - 1 - diethylaminoethoxybenzene by treatment with benzyl chloride followed by reduction of the nitro group).  Samples have been furnished under Sect. 2 (5) of the following compounds:--(1) N - diethyl - N - dodecyloxymethyl - N - 3 - methoxyphenoxyethyl ammonium chloride, prepared from dodecyloxymethyl chloride and 3-methoxyphenyl - b  - diethylaminoethyl ether; (2) N - dimethyl - N - benzyl - N - g  - (3 - n - octyloxyphenoxy) - b  - hydroxypropylammonium chloride, prepared from benzyl chloride and N - dimethyl - \su - (3-n-octyloxyphenoxy)-b  - hydroxypropylamine, which is obtainable from sodium 3 - n - octyloxyphenolate and g  - dimethylamino - b  - hydroxypropyl chloride.  The products are soluble in water and are useful as wetting, emulsifying and foaming agents and as antiseptics, disinfectants and preservatives.  Alone or mixed with other active or inert substances, such as powders, ointment bases and creams, they may be used for cleaning and disinfecting medical instruments, floors, walls, &c. or for disinfecting the skin, or for cleansing and preserving vegetables and fruits and animal substances such as meat, hides and skins, and glands and other animal organs.  Particulars are given of the bactericidal action of certain of the products specified above and also of N-diethyl-N-benzyl-N-p-cetylaminophenoxyethylammonium chloride.  The Specification as open to inspection under Sect. 91 includes examples describing the preparation of (1) N-dimethyl-N-butyloxymethyl - N - 3 - dodecyloxyphenoxyethylammonium chloride from butyloxymethyl chloride and 3 - dodecyloxyphenyl - b  - dimethylaminoethyl ether (obtainable from sodium 3-dodecyloxyphenolate and dimethylaminoethyl chloride); (2) N-dimethyl-N-benzyl-N-g -(3-n-hexyloxyphenoxy)propylammonium chloride from benzyl chloride and 3-n-hexyloxyphenyl-g -dimethylaminopropyl ether (obtainable from sodium 3-n-hexyloxyphenolate and g -dimethylaminopropyl chloride); (3) N-dimethyl-N-phenylethyl - g  - (3 - butyloxyphenoxy) - b -dimethylpropylammonium bromide from phenylethyl bromide and N-dimethyl-g -(3-butyloxyphenoxy) - b  - dimethylpropylamine (obtainable from sodium 3-butyloxyphenolate and g  - dimethylamino - b  - dimethylpropyl chloride).  The Specification refers also to the manufacture by the processes described above of aromatic compounds substituted by a quaternary aminoalkyl group and by a saturated or unsaturated alkyl, cycloalkyl, aryl or aralkyl group, each substituent being linked t