SU432130A1 - METHOD OF OBTAINING SURFACE-ACTIVE QUARTERLY AML / ONI SALTS - Google Patents

Description

one

The invention relates to a process for the preparation of new compounds of quaternary ammonium salts with a p-alkoxymethylIleneoxyethyl radical in nitrogen, which can be widely used in medicine and the food industry as disinfectants.

A known method for the preparation of quaternary AMMONIUM salts with different groups.

The purpose of the present invention is to develop a process for the preparation of surface-active ammonium salts with a p-alkoxymethyl long-chain ethyleneoxyethyl radical with nitrogen, which makes it possible to obtain new quaternary ammonium salts, which by their properties can exceed those known so far.

The proposed method for producing compounds of the general formula

(ROCHsOCHsCH.N (CH3) 2H X-),

where R is alkyl containing 7 or more carbon atoms; R is a short-chain radical which may contain hydroxy and methoxy, a double bond, and it may also be benzyl or furfuryl radicals; X - anions of chlorine, iodine, and methyl sulfate, is that trimethylamine or P- (alkoxymethylenoxy) ethyldimethylamines are reacted with alkoxymethyl-p-chloroethyl ethers in an inert solvent when heated or cooled (O-110 ° C) for 4-20 hours and the desired products are isolated by known methods.

Example 1. Synthesis of | 3- (heptyloxymethylene) ethyltrimethylammonium chloride.

8.35 g (0.04 mol) of heptyloxymethyl-p-chloroethyl ether and 20 ml of absolute toluene containing 4.73 g (0.08 mol) of trimethylamine are placed in a glass ampoule, sealed and heated at 100-105 ° in for 18 hours After that, the ampoule is opened, the precipitated Quaternary salt is filtered off, washed on the filter with absolute sulfuric ether and dried in a vacuum desiccator over sulfuric acid. 7.5 g or 70% of theory are obtained. T. pl. 84-86 ° (from dioxane).

Found,%: C1 13.38; N 5.31.

CisHsoNOsCl.

Calculated,%: C1 13.25; N 5.25.

Example 2. Synthesis of p- (octyloxymethylenoxy) ethyltrimethylammonium chloride.

From 8.91 g (0.04 mol) octyloxymethyl-chloroethyl ether and 4.73 g (0.08 mol) of trimethylamine in 20 ml of absolute toluene in

conditions similar to example 1, 8.12 g (72%) of product are obtained. T. pl. 90-92 ° (from dioxane). Found,%: C1 12.69; N 5.02. Ci4H32iN02CL Calculated,% C1 12.58; N 4.975. The surface tension of a 1% aqueous solution is 42.4 dyne / cm; 5% PG, 7 Dyne / cm, respectively. Example 3. Synthesis of | 3- (decyloxymethylene) ethyltrimethylammonium chloride. 5.02 g (0.02 mol) of decyloxymethyl-p-chloroethyl ether and 3, H g (0.06 mol) of trimethylamine in 20 ml of absolute toluene are heated in a vented glass ampoule for 20 hours at 105 PO. The precipitated quaternary salt is treated analogously to the example,. 4.5 g (72.4%) of the product are obtained. G. pl. / U-80 (from dioxane). Found 7: C1 11.40; N 4.65. CisHseNOsCl. Calculated,%: C1 11.44; N 4.52. The surface tension of a 1% aqueous solution is 37.4 dyn / cm, 0.5% 43 dyn / cm. The aqueous solutions upon shaking form an abundant foam, the half-life of which for a 1% solution is dO min. Example 4. Synthesis of p- (dodecyloxy. Methyleneoxy) ethyltrimethylammonium chloride. From 2.79 g (0.01 mol) of dodecyloxymethyl-chloroethyl ether and 1.8 g (0.03 mol) of trimethylamine in 20 ml of absolute toluene under conditions similar to example 3, 2.77 g (82%) of the product are obtained . T. pl. 69-70 ° (from dioxane). Found,%: C1 10.58; N 4.32. Cl8H4oNO2Cl. Calculated,%: C1 10.49; N 4.16. The surface tension of a 1% aqueous solution is 42.6 dyn / cm and 0.5% 44 dd / cm, respectively. When shaken, aqueous solutions form a rich foam, the half-life of which is 20 minutes for a 1% solution and 45 minutes for a 0.5% solution. Syringe 5. Synthesis (3- (tridecyloxymethylenoxy) ethyltrimethylammonium iodide. In a three-necked flask, I need 50 ml bones, equipped with a stirrer, thermometer and channel funnel, 4.55 g (0.015 mole) p - (tridecyloxymethylenethynemethylamino)). and 30 ml of absolute sulfuric ether; 2.13 g (0.015 mol) of methyl iodide is added at 10-15 ° C. Then the reaction mixture is stirred at room temperature for 1.5-2 hours. The precipitated quaternary salt is treated in a manner similar to Example 1 5.46 g (77.5%) of the product is obtained, mp: 92-93 °. Found: I 28.53; N 3.22. CigH.sNO. Calculated o%: I 28.61; N 3.16. The surface tension of a 1% aqueous solution is 26.2 dyne / cm and 0.5% - 27.3. When shaken, they form a copiously stable foam. Example 6. Synthesis of p- (dodecyloxymethylenoxy) -ethyltrimethylammonium methyl sulfate. From 4.3 g (0.015 mol) of P- (dodecyloxymethylenoxy-) ethyl dimethylamine in 15 ml of absolute sulfuric ether and 1.9 g (0.015 mol) of dimethyl sulfate in 15 ml x, similar to example 5, get 4.8 g (77%) of the Quaternary salt. T. pl. 51-53 ° (from dioxane). Found 7: S 7.80; N 3.32. С19Н4з1 OB. Calculated,%: S 7.75; N 3.38. The iHoBepxHocTHoe tension of 1% - < 2 > and 0.5% aqueous solutions is 32.7 and 34 dyn / cm, the aqueous solutions upon shaking form a plentiful oil, whose half-life is more than 1 hour. Example 7. Synthesis of p- (dodecyloxymethylenoxy) Elyldimethylmethoxymethylammonium chloride and chloride. 4.3 g (0.015 mol) of P- (dodecyloxymethylenoxy) ethyldimethylamine and 15 ml of absolute sulfuric ether are placed in the device described in example 5 and 1.2 g (0.015 mol) are added to the resulting solution at O-5 ° monochloromethyl ether. The reaction mixture is stirred at room temperature for 1.5-2 hours. The precipitated quaternary SALT is treated analogously to example 1. Get 3.78 g (69%) of the product. T. pl. 50-51 °. Found,%: C1 9.74; N 3.85. C39H42N03C1. Calculated,%: C1 9.64; N 3.81. The surface tension of a 1% aqueous solution is 34.4 dyne / cm and 5% of 36.4 dyne / cm, the aqueous solutions form a copious but unstable, with a period of 10–15 min. Example 8. Synthesis of P- (nonyloxymethylenoxy) -ethyl dimethylbenzylammonium chloride. In a two-neck flask with a capacity of 30 ml, equipped with a thermometer and a return cooler, the number is 3.68 g (0.015 mol) of P- (Nonoxyloxymethylenoxy) ethyl dimethylamine and 2 g (0.015 mol) of freshly distilled benzyl chloride. The mixture is heated at 70-75 ° C for 4 hours. The mass which crystallized upon cooling to room temperature was diluted with 50 ml of absolute sulfuric ether, the quaternary salt was worked up as in Example 1. 4.95 g (90%) of product were obtained. T. pl. 78-79 ° C (from dioxane). Found,%: C1 9.62; N 3.75. C21H38N02C1. Calculated,%: C1 9,53; N 3.78. The surface tension of a 1% aqueous solution is 38.4 dyn / cm and 5% of 39.2 dyn / cm; when shaken, aqueous solutions form a foam, which quickly collapses, its half-life is 3-5 minutes. Example 9. Synthesis of p- (desoxymethalenoxy) ethyldimethyloxyethylammonium chloride.

3.9 g (0.015 mol) of p- (detoxymethylenoxy) ethyldimethylamine and 1.21 g (0.015 mol) of freshly distilled ethylene chlorohydrin are placed in the device described in example 8. The mixture is heated for 6 hours at 90-95 °. Then it is cooled to room temperature and the crystallized mass is treated in the same manner as in Example 8. 3.7 g (70%) of product are obtained. 1. pl. 41-42 ° (from dioxane).

Found,%: C1 10.60; N 4.25.

CuHssNOsCl.

Calculated,%: C1 10.43: № 4.12.

The surface tension of a 1% aqueous solution is 34.2 dyn / cm and 5%

38.0d / cm; when shaken, aqueous solutions form a rich foam, the half-life of which is 10 minutes for a 1% solution and 60 minutes for a 0.5% solution.

Example 10. Synthesis of p- (tridecyloxymethylene) ethyl dimethyl lammonium chloride.

In the device described in Example 8, 3.5 g (0.012 mol) of p- (trdecyloxymethylenoxy) ethyldimethylamine and 1.53 g (0.020 mol) of allide chloride are placed. The mixture is heated for 4 hours at 80 ° C, then cooled to room temperature and treated in the same way as in Example 8. 3.68 g (81%) of product are obtained. T. pl. 65-66 (from dioxane).

Found,%: C1 9.45; N3.78.

C2lH44N02C.

Calculated,%: C1 9.38; N 3.705. The surface tension of a 1% aqueous solution is 36.7 dyn / cm and 5% is

38.1 d / cm The aqueous solutions upon shaking form a not very abundant foam, but which is very stable.

PRI me R 11. Synthesis of P- (nonyloxymethyleneglycol) ethyldimethylfurfuryl ammonium chloride.

3.68 g (0.015 mol) of p- (nonyloxymethylenoxy) ethyldimethylamide are placed in the device described in example 8 on 1.75 g (0.015 mol) of furfuryl chloride in the form of a 14% benzene solution. The mixture is heated for 3 hours at 75 °, then the benzene is distilled off in vacuo, and the remaining mass is diluted with 30 ml of absolute sulfuric ether and set in the refrigerator. The precipitated quaternary salt is treated analogously to example 1. 3.56 g (65%) of the product is measured. T. pl. 50-52 ° (from dioxane).

Found,%: C1 9.96; N 3.93.

CigHaaNOaCl.

Calculated,%: C1 9,79; N 3.87.

The surface tension of a 1% aqueous solution is 35 dyn / cm, and 5% 41.7 dyn / cm; shaking solutions form a foam, the half-life of which is 5 minutes for a 1% solution and more than 1 hour for a 0.5% solution.

Subject invention

Claims (2)

1. A method for preparing surface-active quaternary ammonium salts, characterized in that trimethylamine or P- (alkoxymethylene) ethyldimethylamines alkylate the alkoxymethyl-p-chloroethyl eff, and isolate the target product in a known manner. 2. A method according to claim 1, characterized in that the alkylation is carried out at about 110 ° C.