Patent GB-441473-A (GB)
Title: The manufacture of quaternary ammonium compounds and preserving and disinfecting media containing the same
Filed: 1934-06-13
Abstract: Quaternary polyammonium compounds in which the pentavalent nitrogen atoms are not members of a ring, and which contain at least one higher aliphatic radicle, i.e. a saturated aliphatic radicle of at least eight carbon atoms, are prepared by any of the following processes: (1) an aliphatic compound containing at least two reactive substituents is treated with at least two molecular proportions of a tertiary amine, one at least of the reagents containing a higher aliphatic radicle; the aliphatic compound is preferably an ester of a polyhydric alcohol with a hydrogen halide or aromatic sulphonic acid; (2) a tertiary polyamine is treated with a reactive ester, e.g. an alkyl halide or sulphonate, in an amount sufficient to yield a polyammonium compound, at least one of the reagents containing a higher aliphatic radicle; as a modification, this process may be effected in stages, only one tertiary amino group being converted into the quaternary form in the first stage, and different reactive esters, if desired, being used in the different stages; (3) a quaternary ammonium compound containing a hydrocarbon radicle carrying a reactive substituent, e.g. a trialkylammoniumalkyl halide, is treated with a tertiary amine, at least one of the reagents containing a higher aliphatic radicle.  The products may contain substituents such as halogen atoms or hydroxyl or sulphhydryl groups. The higher aliphatic radicle may be a hydrocarbon radicle or it may be interrupted by oxygen or sulphur.  Examples are given of the preparation of polyammonium compounds from (1) tetramethylethylenediamine and dodecyl bromide (or methyl bromide and sym. dimethyldidodecylethylenediamine); the thiocyanate, nitrate and cyanide of the product are obtainable by double decomposition, and the free base by reaction with silver hydroxide; (2) tetramethylethylenediamine and dodecyloxymethyl chloride; (3) tetramethylethylenediamine and dodecylthiomethyl chloride; (4) tetrabutylethylenediamine and dodecyloxymethyl chloride; (5) tetramethyl-b -oxypropylenediamine and dodecyl bromide (or dimethyldodecylamine and glycerol dibromohydrin); (6) tetramethyl-b -oxypropylenediamine and b -oxy-g -dodecyloxypropyl chloride; (7) sym. dimethyldidodecyl - b  - oxypropylenediamine and benzyl chloride; (8) methyl - bis - diethylaminoethylamine and decyloxymethyl chloride; (9) sym. dimethyldidodecylethylenediamine and benzylthiomethylchloride; (10) diethylaminoethyl chloride and benzyl bromide, followed by reaction with dimethyldodecylamine; (11) dimethyloctadecylamine and dichloracetone; (12) sym. dimethyldioctyl - b  - oxypropylenediamine and allyl bromide; (13) tetramethylmethylenediamine and dodecyl bromide.  Specification 414,712 is referred to.  Sym. Dimethyldidodecylethylenediamine, used in example 1, is prepared by heating ethylene dibromide with twice the molecular proportion of dodecylmethylamine. Tetrabutylethylenediamine, used in example 4, is prepared similarly from ethylene dibromide and dibutylamine.  Dimethyldodecylamine, used in example 5, is prepared by heating dodecyl bromide with dimethylamine.  Methyl-bis-diethylaminoethylamine, used in example 8, is prepared by heating methylamine with twice the molecular proportion of diethylaminoethyl chloride.  Dimethyloctadecylamine, used in example 11, is prepared by heating octadecyl bromide with dimethylamine.  Dodecyloxymethyl chloride, used in examples 2 and 4, is prepared by treating dodecyl alcohol with formaldehyde in presence of hydrochloric acid.  Decyloxymethyl chloride, used in example 8, is prepared similarly from decyl alcohol.  Benzylthiomethyl chloride, used in example 9, is prepared similarly from benzyl mercaptan.  Sym. Dimethyldidodecyl - b  - oxypropylenediamine, used in example 7, is prepared by treating dibromohydrin with twice the molecular proportion of methyldodecylamine.  Sym. Dimethyldioctyl-b -oxypropylenediamine, used in example 12, is prepared similarly from dibromohydrin and methyloctylamine.