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With sodium hydroxide; In water; at 50.0℃; for 0.2h;Product distribution / selectivity;
The reaction solution obtained from Example 2 was neutralized by adding 30% strength aqueous sodium hydroxide dropwise at 50 C. over a period of 0.5 h. The yield of sodium methallylsulfonate in the reaction mixture is 95.2% based on the sulfur trioxide-DMF complex. 330 g of DMF (10%) were lost as a result of hydrolysis.; Example 4 InventiveThe reaction mixture obtained from Example 2 was admixed at 50 C. with 1.6 kg of water. The mixture was subsequently neutralized at 50 C. by means of 30% strength aqueous sodium hydroxide. The yield of sodium methallylsulfonate in the reaction mixture was likewise 95.2% based on the sulfur trioxide-DMF complex. The loss of DMF as a result of hydrolysis was less than 0.3%.
With sodium hydroxide; dihydrogen peroxide; In water;
EXAMPLE 3 196 g (2 mol) of maleic anhydride and 150 g of ion-exchanged water were placed in a four-necked flask fitted with the same devices as in Example 1. 117 g (1.4 mol) of 48% sodium hydroxide was added thereto under stirring to neutralize the same. 94.8 g (0.6 mol) of <strong>[1561-92-8]sodium methallylsulfonate</strong> was added thereto and the temperature was elevated to a reflux temperature. Thereafter, 68 g of a 60% hydrogen peroxide solution was added dropwise thereto over 2 h. After aging for 1 h, 47 g of 30% sodium persulfate and 57 g of a 60% aqueous hydrogen peroxide solution were added dropwise thereto over 3 h. Simultaneously 50 g (0.6 mol) of 48% NaOH was added dropwise over 2 h. After aging under reflux for 2 h, the reaction mixture was cooled to obtain a copolymer of maleic acid and methallylsulfonic acid (molar ratio of 100/30). The resulting copolymer had a rate of polymerization of 92.8%, a number-average molecular weight of 420 and MW /MN of 1.26.
N-(4-anilino)phenylisopropenylsulfonamide[ No CAS ]
[ 14568-34-4 ]
Yield
Reaction Conditions
Operation in experiment
79%
With phosphorus pentachloride; triethylamine;
SYNTHESIS EXAMPLE 5 14.1 g (0.1 mole) of methallylsulfonyl chloride prepared from <strong>[1561-92-8]sodium methallylsulfonate</strong> and phosphorus pentachloride was added to 200 ml, and 18.4 g (0.1 mole) of p-aminodiphenylamine and 10 g of triethylamine were added gradually to the solution. The mixture was stirred at 0 C. for 2 hours. The resulting precipitate was separated to afford 23.9 g (yield 79%) of N-(4-anilino)-phenyl isopropenyl sulfonamide having a melting point of 129 C.
With sodium hydroxide; sulfur trioxide; In 1,2-dichloro-ethane;
EXAMPLE 4 In a flask similar to that as described in Example 1, 300g of 1,2-dichloroethane and 28.7g (0.25 mol) of N-tert-butylacetamide were charged and cooled to -5 C. Then 19.2 g (0.24 mol) of sulfur trioxide was added to the mixture through the dropping funnel. N-tert-butylacetamide suspended in 1,2-dichloroethane is converted to a complex with sulfur trioxide, and a colorless transparent solution was obtained. The resulting complex solution of sulfur trioxide -N-tert-butylacetamide was kept at -5 C. and 14g (0.25 mol) of isobutylene was fed into the flask. The solution was gradually heated under stirring and the stirring was continued for 2 hours at 35 C. The resulting solution was colorless and transparent. Then the solution was submitted to distillation under reduced pressure (20 mmHg) to remove 1,2-dichloroethane. The residue was diluted with water and neutralized with a 20% aqueous solution of sodium hydroxide. The neutralized aqueous solution containing N-tert-butylacetamide and sodium methallyl sulfonate was extracted with 200 g of ethyl acetate, to remove N-tert-butylacetamide with ethyl acetate and to leave the sodium methallyl sulfonate in aqueous solution. From the ethyl acetate solution by a usual manner N-tert-butylacetamide was recovered (recovery rate: 90%). The aqueous solution was evaporated under reduced pressure (20 mmHg) to obtain 36 g of white crystalline sodium methallyl sulfonate. By IR spectrum, the product was identified with a standard sample. The purity of the product was 95% and the yield 90%.
After the neutralization, more of the N-tert-butylpropionamide was precipitated and filtered (recovery rate of N-tert-butylpropionamide: 91%). The neutralization was carried out with sodium carbonate to pH 7. The neutralized filtrate was evaporated under reduced pressure (20 mmHg) to remove water and to obtain 46.5 g of white crystalline sodium methallyl sulfonate. The product was identified with a standard sample by IR spectrum. The purity of the product was 95.5% and the yield 95%.
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