RU2188667C1 - Method of synthesis of disinfecting substance didecyldimethylammonium bromide clathrate with urea - Google Patents

Abstract

FIELD: medicine, disinfecting agents. SUBSTANCE: method involves interaction of didecyldimethylammonium bromide with an urea saturated solution in an organic solvent at definite temperature and mass ratio. Didecyldimethylammonium bromide is synthesized by interaction of didecylmethylamine with methyl bromide in definite parameters and ratio of reagents. Method provides preparing a disinfecting agent showing bactericidal, virumicidal, fungicide, antiseptic and detergent properties additionally. EFFECT: improved method of synthesis and preparing, valuable medicinal properties. 1 tbl

Description

 The invention relates to the field of disinfectant technology, in particular, to the production of urea adducts of a quaternary ammonium compound (HOUR) having bactericidal, virucidal, fungicidal, antiseptic activity and having use as disinfectant, antiseptic, washing and fungicidal agents.

 A known method for producing disinfectants of urea adducts of a quaternary ammonium compound, comprising reacting a quaternary ammonium compound in an organic solvent with a saturated urea solution, filtering, precipitating, draining from the precipitate, separating the adduct, washing with a cold solution and drying (US Pat. No. 2,676,955, 1954) - (1 )

 This patent describes the preparation of carbamide compounds of clathrates of such QAS as lauryltrimethylammonium chloride, dilauryl dimethylammonium bromide.

 Mention of carbamide clathrates of didecyldimethylammonium bromide and its receipt in this patent and other published and public sources is not found.

 Adducts of urea and a quaternary ammonium compound are prepared by reacting the above reagents in an organic solvent, followed by separation of the crystalline and liquid phases.

 Thus, in order to produce said adduct, it is necessary to obtain the corresponding salt in the first step. The latter, in turn, is synthesized by the reaction of amines with alkyl halide.

 In Russia, there is practically no raw material base for the production of decylamines; there is also no industrial production of secondary amines.

 The objective of the present invention is to provide an improved method for producing urea adducts of a quaternary ammonium compound with a reduced amount of impurities, with a high yield of the target product, with such a combination of urea and a quaternary compound in a composition that has a synergistic effect that enhances bactericidal, virucidal, fungicidal properties and improves quality .

The problem is solved in that in a method for producing a disinfectant of urea adducts of a quaternary ammonium compound, comprising reacting a quaternary ammonium compound in an organic solvent with a saturated urea solution, filtering, precipitating, draining from the precipitate, separating the adduct and drying, according to the invention, as a quaternary ammonium compound use didecyldimethylammonium bromide obtained by the interaction of didecylmethylamine with methyl bromide in an organic solvent at mass m reactant ratio respectively of 2.5: (1-1.5) :( 1-1.5), at a pressure of 0.05-0.1 MPa and a temperature of 50-90 ^o C, and reacting with a solution of saturated urea didecyldimethylammonium bromide is carried out at a temperature of 70-100 ^o With a mass ratio of reactants 1: 2-2.5.

 For the production of high molecular weight amines, it is possible to use both natural and petrochemical raw materials.

 Amines, the alkyl chain of which has 10 carbon atoms, can be obtained from natural oils such as coconut or palm kernel, with a small yield (as a by-product in the production of dodecylamine).

 From petrochemical feedstocks, alcohols obtained by oligomerization of ethylene (Ziegler method) can be used for the production of decyl- or didecylamine.

 Industrial methods for producing amines from fatty acids are mainly implemented in two directions: a two-stage method, according to which, at the first stage, nitriles are obtained by ammonolysis of fatty acids, which are converted to amines and one-stage hydroammonolysis of fatty acids by hydrogenation. In the single-stage hydro-ammonolysis of fatty acids, dehydration and hydrogenation processes occur simultaneously on the same catalyst, which has both dehydrating and hydrogenating properties.

 Obtaining didecyldimethylammonium bromide was carried out in several technological stages.

 Nitriles were obtained from a small amount of capric acid. Nitriles were obtained by ammonolysis of capric acid in a continuous apparatus over a stationary catalyst - aluminum oxide (2).

At a temperature of 360 ^o C and a pressure of 3-5 atm. obtained nitriles, which were subjected to distillation. The result is distilled nitriles having the following characteristics:
Acid number, CN - 0.15 mg KOH / g
Mass fraction of amines - 0.8%
The catalytic hydrogenation of nitriles proceeds through the intermediate formation of aldimines. Aldimines during the reaction not only recover to primary amines, but also interact with primary amines, forming Schiff bases, reducing to secondary amines.

 The formation of secondary amines is also possible during the condensation of two aldimine molecules (3).

 The formation of secondary amines is also possible due to the deamination of two molecules of the primary amine.

Hydrogenation of nitriles was carried out in an autoclave at the following technological parameters: pressure - 3.0 MPa, temperature - 180 ^o C. As a catalyst, promoted nickel on chromium oxide was used. The greatest yield of secondary amines was achieved by removing more than 85% of the ammonia formed in the reaction from the reaction zone.

The resulting hydrogenate was characterized by the following composition:
Mass fraction of primary amines - 7.2%
Mass fraction of secondary amines - 85.4%
Mass fraction of tertiary amines - 4.3%
A fraction of didecylamine with a mass fraction of secondary amines of 97.9% was isolated by distillation from the hydrogenate.

Then, didecylamine was methylated by the reaction of didecylamine with formaldehyde in the presence of hydrogen using a hydrogenation catalyst (4) at a temperature of 90-120 ^o C, a pressure of 4.0-5.0 MPa and a molar ratio of amines: formaldehyde - 1: 2.5 the yield of didecylmethylamine reached 99%

By distillation, a fraction of didecyldimethylamine was isolated, which had the following characteristics:
Mass fraction of didecylmethylamine - 99.7%
Melting point - 8 ^o C
Density - 0.81 g / cm ³
The interaction of didecylmethylamine with methyl bromide gave a quaternary ammonium salt, didecyldimethylammonium bromide.

The reaction was carried out in an autoclave at a pressure of 0.05-0.1 MPa and a temperature of 50-90 ^o C in an organic solvent with a mass ratio of reactants, respectively, 2.0: (1-1.15) :( 1-1.5).

 The reaction proceeds exhaustively. There are no starting amines in the finished product.

 Clathrate compounds are formed by mixing the components in a saturated or supersaturated solution. The methods described in the literature for the preparation of QH urea clathrates with urea are, as a rule, preparative in nature and are of little use in order to become the basis for the development of technological production.

The obtained didecyldimethylammonium bromide in a solvent is mixed at a temperature of 25-35 ^o With a saturated solution of urea in a mass ratio of reagents 1: (2-2.5).

 Examples of carrying out the invention.

 Example 1

5 parts by weight are placed in an autoclave. didecyldimethylamine and 0.5 parts by weight methyl bromide, 0.5 wt.h. isopropyl alcohol. The reaction is carried out at a pressure of 0.05 MPa and a temperature of 50 ^o C. Get didecyldimethylammonium bromide, in which there are no starting amines. The obtained didecyldimethylammonium bromide in isopropyl alcohol is mixed at a temperature of 35 ^o With a saturated solution of urea in methanol at a reagent ratio of 1: 2. Then diethyl ether was added, the precipitated crystalline precipitate was filtered off, precipitated, drained from the precipitate, the adduct was separated, washed with cold diethyl ether and dried. A white crystalline powder is obtained.

 Example 2

K 4.5 parts by weight didecyldimethylamine add methyl bromide and isopropyl alcohol in a reagent ratio of 2: (1-1.5), respectively. The reaction is carried out at a pressure of 0.1 MPa and a temperature of 80 ^o C. The obtained didecyldimethylammonium bromide in acetone is mixed at a temperature of 25 ^o With a saturated urea solution in a ratio of 1: 2.5. The separation is carried out as in example 1. Get a white crystalline powder.

 Example 3

 Didecyldimethylamine, methyl bromide and isopropyl alcohol are placed in an autoclave at a reagent ratio of 2.5: 1.5: 1.0.

The reaction is carried out at a pressure of 0.08 MPa and a temperature of 90 ^o C. The obtained didecyldimethylammonium bromide in isopropyl alcohol is mixed at a temperature of 30 ^o C with a saturated solution of urea in low aliphatic alcohol (C1 to C6) with a reagent ratio of 1-2.2. The reaction mixture was then dissolved in 30 ml of diethyl ether and filtered. The solids separated are washed with additional diethyl ether and air dried for 20 minutes. The resulting product is a fine white powder.

 Analysis of the obtained compound for the content of ionic bromine by argentometry showed a mass fraction of Br - 6.09%. This corresponds to a mass fraction of didecyldimethylammonium bromide in clathrate of 30.9% and the following proportion: per mole of HOUR - 15.7 moles of urea.

 The table shows the results of analyzes of the obtained samples.

 Small deviations in the melting temperature may be due to the characteristics of the installation for determining this indicator.

 The results shown in the table allow us to conclude that the proposed method and the optimal ratio of components allowed to achieve a high yield of the target product. Obtaining this product is very important for a domestic manufacturer using this product in various areas of the national economy, including in the production of disinfectants, bactericides, fungicides, pharmaceuticals and detergents.

Literature
1. US patent 2676955, 1954

 2. USSR copyright certificate 387980.

 3. Green S.A. and other cationic surfactants. M .: TSNIITE Neftekhim, 1979.

 4. Petryakova N.K. and other Oil refining and petrochemicals. 9, 1977.

Claims (1)

A method for producing a disinfectant of urea adducts of a quaternary ammonium compound, comprising reacting a quaternary ammonium compound in an organic solvent with a saturated urea solution, filtering, precipitating, draining from the precipitate, separating the adduct, washing with a cold solvent and drying, characterized in that as a quaternary ammonium compound use didecyldimethylammonium bromide obtained by the interaction of didecylmethylamine with methyl bromide in an organic solvent and the mass ratio of reagents, respectively, 2.5: (1.0-1.5): (1.0-1.5), at a pressure of 0.05-0.1 MPa and a temperature of 50-90 ^o C, and the interaction of saturated urea solution with didecyldimethylammonium bromide is carried out at a temperature of 25-35 ^o With a mass ratio of reagents 1: 2-2.5.

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