SU502877A1 - The method of obtaining-methacrylate or dimethacrylate - Google Patents

Description

one

The invention relates to a process for the preparation of new compounds N-methacryl or M, N-dimethacryl sulfamides of the general formula

about

.N

/ L

II

-S-n

II O II I

about SI, about Sivnii N -

where R is alkyl, which can be used as monomers for the production of heat-resistant, antimicrobial, high-strength polymers.

The method is based on the known reaction of obtaining substituted sulfamides by reacting their sodium salts with the corresponding chlorine derivatives.

According to the proposed method, N-methacryl- or N, M-dimethacryl sulfonamides of the indicated general formula are obtained by reacting alkylaryl sulfamide with sodium hydroxide in a molar ratio of 1: 0.95-4-1.1 or 1: 1,, 1, respectively, in the medium an organic solvent, for example chlorobenzene, at 110-115 ° C, followed by treatment of the alkylarylsulfonamide salts thus obtained with methacrylic acid chloride at a temperature of -15 ° -10 ° C in an organic solvent medium, for example acetone.

It is recommended to conduct the process preferably at a 1: 1 or 1: 2 ratio of alkylarylsulfamide and sodium hydroxide.

As an alkyl aryl sulfamide, it is recommended to use a technical mixture of alkyl aryl sulfamides with various alkyl radicals. Based on the synthesized compounds can be obtained heat-resistant polymers

as a result of the R-Igrg-groups, when

this sulfamide group attaches to the molecule

antimicrobial action.

The yield of the target product is 80-

Claims (3)

90%. The structure and composition of the products obtained were confirmed by the determination of molecular weight, elemental analysis, and IR spectra. The purity of the product is determined using toicolysis chromatography on alumina grade II plastic. eluting with an aceto system:: 5 and methanol: dioxane: benzene 1: 1: 8. Example 1. Preparation of N-methacryltoluene sulfamide. In a three-necked flask equipped with a stirrer and a direct condenser, 17.1 g (0.1 mol)--toluenesulfamide, 4 g (0.1 mol) of powdered caustic soda and 150 ml of anhydrous chlorobenzene are placed and the mixture is heated for 1 hour at PO -115 ° C. In the course of the reaction, the solvent and water are distilled off as an azeotropic mixture. After separating the calculated amount of water, crystals are filtered off from the reaction mixture; they are recrystallized from methanol to obtain 17 g of sodium toluene sulphamide with m.p. 225-227 ° C. To a suspension of 9.8 g (0.05 mol) of sodium toluenesulfonamide and 75 ml of acetone, while cooling to Minus 10-15 ° C, 5.22 g (0.05 mol) of methacrylic acid chloride are added in 30 minutes. At the end of the addition of all the chlorohydride, the reaction mixture is stirred esh for 40 min at -20 ° C. Next, the solution is filtered from the precipitated salt, the filtrate is evaporated in a water jet pump vacuum to 30 ml, cooled to minus 10-15 ° C and an equal amount of water is added to it. The precipitated crystals are separated and recrystallized from ether. 11.2 g (92.5%) of H-methacryltoluenesulfonamide are obtained, which is a white powder with m.p. 69-70 ° C, soluble in alcohol, acetone and sulfuric ether, insoluble in benzene, cyclohexane and other hydrocarbons. Found,%: C 55.46, 54.65; H 5.55, 5.78; S 13.04, 13.10; N 5.73, 5.62. CiiHisSNOaCalculated,%: C 55.10; H 5.43; S 13.38; N 5.84. A bromine number of 65 was found. A bromine number of 67 was calculated. Example 2. Get M, M-di1metta "riltoluene sulphamide. 17.1 g (0.1 mol) “-toluenesulfonamide and 8 g (0.2 mol) of crushed caustic soda in 150 ml of anhydrous chlorobenzene are loaded into a flask equipped with a refrigerator, and the mixture is heated for 1.5 hours at 110-115 ° C . During the reaction, the solvent and water are distilled off as an azeotropic mixture. After separating the calculated amount of water, crystals are filtered off from the reaction mixture; they are recrystallized from methanol and get disodiumtoluenesulfMID with so pl. 354-357 ° C. To a suspension of 10.5 g (0.05 mol) of disodium toluene sulfamide in 100 ml of acetone, 10-45 g (0.1 mol) of methacrylic acid chloride are poured over 40 minutes while cooling to minus 10-15 ° C. At the end of the addition of all the acid chloride, the reaction mixture is stirred at-minus 20 ° C e.e 1 hour. Then the solution is filtered from the precipitated salt, the filtrate is evaporated in a water-jet pump vacuum to 30 ml, cooled to minus 10-15 ° C and added to him an equal amount of water. The precipitated crystals are separated, recrystallized from sulfuric ether. 10.67 g (yield 68%) of M, N-dimethacryltoluenesulfamide, which is a white powder with m.p. 96-97 ° C, soluble in methanol, chloroform and acetone, insoluble in water, benzene, heptane and other hydrocarbons. Found,%: C 58.24; 58.19; H 5.30; 5.34; S 10.60; 10.67; N 4.34; 4.19. Ci5Hi7SN04. Calculated,%: C 58.63; H 5.53; S 10.42; N 4.56. Example 3. Obtaining N-methacrylamine on the basis of a mixture of arylsulfonam. Under conditions similar to those of Example 1, to 18.5 g of the mixture of aryl sulfamides obtained from the aromatic hydrocarbons of the gas condensate of the Uchkyr field, 4 g of ground caustic soda are added to the chlorobenzene solution. 10.3 g of sodium arylsulfamide are obtained with m.p. 243 ° -246 ° С. 5.2 g of methacrylic acid chloride are added to a suspension of 10 g of sodium arylsulfamide in acetone. 10 g (yield 80%) of a mixture of N-methacrylaryl sulphamides, which is a pale yellow oil, soluble in alcohols, acetone, benzene, insoluble in water and well decolorizing bromine water is obtained. Example 4. Preparation of NuY-dimethacrylaryl sulfamides based on a mixture of aryl sulfamides. Under conditions similar to those of Example 2, to 9.3 g (0.05 mol) of a mixture of arylsulfonamides derived from aromatic hydrocarbons from the Uchkyrskoye gas condensate, 4 g (0.1 mol) of crushed caustic soda and 11.6 g of disodium arylesulfamide are obtained. 10.5 g (0.1 mol) of methacrylic acid chloride are poured in acetone to a suspension of 10.6 g (0.05 mol) of the obtained disodiumaryl sulfamide (mp. 336-340 ° C) and 10.5 g are obtained (yield 64 %) a mixture of N, N-dimethacrylaryl sulphamides, which is a pale yellow oil with m.p. 175 ° C at mm Hg. Art. (with decomposition), soluble in alcohol, benzene and insoluble in water. Oil bleaches well bromine water. In the IR spectrum, there are absorption bands at 1625 cm-characteristic for -C CH2 bonds, there is no NH bond. Claims 1. A method of producing N-methacryl or N, (N-methacryl sulfamides of the general formula or and where R is alkyl, characterized in that alkylarylsulfamide is reacted with caustic with alkali at a molar ratio of 1: 0.95-g-f-1, 1 or 1: 1.9-2.1, respectively, in an organic solvent medium, chlorobenzene, at 110-115 ° C, followed by treatment of the resulting salts alkylarylsulfonamides methacrylic acid chloride at minus 10-15 ° C in an organic solvent, such as acetone, followed by separation of the target product by known methods. 2. A process according to claim 1, characterized in that the process is carried out at a 1: 1 or 1: 2 ratio of alkylarylsulfonamide and caustic alkali, respectively. 3. A method according to claim 1, characterized in that a technical mixture of alkyl aryl sulfamides with various alkyl radicals is used as the alkyl aryl sulfamide.