US2605286A - Acetonyl alkylbenzyl dialkyl ammonium salts - Google Patents

Description

Patented July 29, 1952 .i UNITsD STATES PATENT OFFICE ACETONYL ALKYLBENZYL DIALKYL AMMONIUM SALTS Sidney Melamedflhiladelphia, anawmard J. Croxall, Bryn Athyn, Pa., assign'ors to Robin" & Haas Compamy,*Philadelphia, Pa acorporation of Delaware No Drawing.

Application January 4, 1951', Serial No. 204,482 a 8 Claims. (01. ace- 7.6)

This invention relates nium salts of the structure to quaternary ammo- R R! RI! wherein an alkyl groupof eight to sixteen The same end result-is achieved by hydrating dimethylaminopropyne or diethylam-inopropyne (cf. J. Chem.- Soc. 1949, 782) .We havediscovered that reaction of the above dialkylaminoa'cetones' with alkylbenzyl halides yields valuable lquaternary ammonium salts which are characterized by an unusual combination of properties.

Suitable alkylbenzyl halides which include also alkylmethylbenzyl and alky-ldimethyl-benzyl =halides; are available through the ha-lomethylation of alkylbenzenes in which the alkylgroup containseight-to; sixteen carbon atoms and preferably nine ito sixteen carbon atoms. The alkyl group 'can 'be of straight or branched chain structure. Particularly useful and economical are alkyl groups obtained from propylene polymers, fractions of which can be taken to give groups predominantly of 9, 12, or carbon atoms. Another economical source of a long-chained alkyl group is from close-cut fractions of kerosene, a fraction having an average size of 14 carbon atoms being quite desirable.

Useful starting hydrocarbons are alkylated benzenes, toluenes, and xylenes', which include n-octylbenzene, n-octyltoluene, n-octylxylenes, 2- ethylhexylbenzene, 1-methylheptyltoluene, (1,3- dimethyl-l-propylbutyl) benzene, 3,5,5 -trimethylhexyl) -benzene, (3,5,5 trimethylhexyDtoluene, (3,5,5-trimethylhexyl) -xylene. nonyltoluene (the nonyl group being from propylene trimer), decylbenzene, n-dodecylbenzene, dodecylbenzene or dodecyltoluene (the dodecyl group being from' propylene tetramer), tetradecylbenzene, tetra decyltoluene, tetradecyldimethylbenzene, pentadecylbenzene, hexadecylbenzene, etc. These are halomethylated with a hydrogen halide and formaldehyde or' paraformaldehyde or with the equivalent thereof conveniently in the 'presence' of such a catalyst as zinc chloride in glacial acetic acid. There are thus obtained the chloromethyl or bromomethyl derivatives.

An alkylbenzyl halide and dimethylaminoacetone or diethylaminoacetone are mixed in) about molar proportions andreacted together'to give quaternary ammonium compounds. The reactionis desirably accomplished in the presence of a solvent; such as benzene, toluene, isopropyl alcohol",- isopropyl ether, acetonitrile, formamide nitromethane, or the like. Heating is useful in accelerating and/or completing thereaction, temperatures of 50 to 125 C. beinggener-ally suitable; The product is obtained as a-residue upon evaporation of solvent, if used. The residue maybe purified by stripping, extraction. or similaroperation, if desired. I 1

p The preparations of typicalquaternary ammonium salts of this invention is illustrated by: the

iollowingexamples, in which parts are by weight.

" Era mailed There were mixed 48 parts of octylbenzylchloride, 20.2 parts ofdimethylaminoacetone,.and 120 partsof dry benzene. The mixture was heated under reflux for fourv hours, after which time it Was found that the titratable nitrogen was essentially zero. The solvent was driven oil to yield a viscous syrup. This was found to contain 3.9% of nitrogen'and'10.1%'of chlorine and 7 to correspond in composition to octylbenzylacet onyl dimethyl ammoniuin chloride; for which thecontents are theoretical nitrogen and chlorine 4.1% and 10:4%, respectively.

This compound is readily soluble in water and:

is compatible with alkaline cleaning solutions.

, It has a phenol coefficient of against -S'ta'phylococcus aurcu s;

Example 2 There were mixed 28 parts of a nonyldimethylbenzyl chloride, 13 parts of diethylaminoacetone, and parts of toluene. The mixture was heated under reflux for five hours. The toluene was removed by heating of the mixture under reduced pressure to yield a gummy residue. This corresponds in composition to nonyldimethylbenzyl acetonyl diethyl ammonium chloride. It has a 3 phenol coefficient of 315 against Staphylococcus aureus and of 225 against Salmonella typhosa. This compound has the formula CnHia CzHs C2H5 0111- o HzooHa Example 3 This compound is readily soluble in water. It gives a phenol coefficient of 335 against Staphylococcus aareus and of 240 against Salmonella typhosa.

Example 4 A mixture of 17 parts of dimethylaminoacetone, 51 parts of 2-methyl-5-dodecy1benzyl chloride, and 120 parts of dry benzene was heated under reflux for three hours. A sample titrated for basic nitrogen showed that the reaction was essentially complete. Concentration under re-' duced pressure gave a quantitative yield of product in the form of a hygroscopic glass. Analysis of this material showed the presence of 8.6% of chlorine and 3.5% of nitrogen. It corresponds in'composition to dodecylmethylbenzyl dimethyl acetonyl ammonium chloride, for which the theoretical chlorine content is 8.66 and the theoretical nitrogen content is 3.42%. It has a phenol coeflicient of 375 against Salmonella typhosaand of 640 against Staphylococcus aureus.

Dodecylbenzyl dimethyl acetonyl ammonium chloride is prepared from dodecylbenzyl chloride and dimethylaminoacetone as above. It has properties very closely similar to those of the dodecylmethylbenzyl compound having phenol coefiicients at least as high as those of the latter.

Example 5 By the procedure of Example 4- there are reacted 17 parts of dimethylaminoacetone and 5'7 parts of a pentadecylbenzyl chloride in which the pentadecyl group was derived from a propylene polymer cut with about 15 carbon atoms in the molecule. The product is pentadecylbenzyl dimethyl acetonyl ammonium chloride. It has a phenol coefi'icient of 600 against Staphylococcus aureus and 395 against Salmonella typhosa.

The alkylbenzyl acetonyl dialkyl ammonium halides of this invention have not only good bac- There were mixed 29.7 parts of nonylbenzyl tericidal properties but also other significant and favorable characteristics. For example, they remain highly effective in hard water and in the presence of organic contaminants. This is a distinct advantage over many otherwise efiective quaternaries. The compounds of this .invention possess good solubility coupled with a favorable stability and it is of interest that the solubilizing group which is here present is not antagonistic to the action of the ammonium group as is often the case. The constituent parts and their particular configuration provide compounds which are advantageous with regard to properties and at the same time are advantageous because they are obtained from readily available and economical starting materials.

We claim: 1. As new chemical substances, compounds of the formula R R. R

wherein R is an alkyl group of eight to sixteen carbon atoms, X and Y are members of the class consisting of hydrogen and the methyl group, R and R" are alkyl groups of not over two carbon atoms, and Z is a member of the class consisting of chlorine and bromine.

2. As new chemical substances, compounds of the formula )3. CH3 CH3 wherein R. is an alkyl group of nine to sixteen carbon atoms.

3. As new chemical substances, compounds of the formula R CH3 CH3 benzyl dimethyl acetonyl ammonium chloride. I

'SIDNEY MELAM'ED.

WILLARD J. CROXALL.

REFERENCES CITED The following references are of recordin the file of this patentf Stevens: J. Chem. Soc. (London), 1930, pp. 2119-2125. v

Claims (1)

1. AS NEW CHEMICAL SUBSTANCES, COMPOUNDS OF THE FORMULA