Hydrolysis chlorosulfonic acid

The hydrolysis of ethyl acetate, prepared by the reaction of ethylene with acetic acid under pressure (154), and the hydrolysis of the ethyl ester of chlorosulfonic acid (155) have been considered and found to be of Httie industrial importance. 

Si, and stannic tetrachloride. An effective smoke agent, whether it be mechanically dispersed from an aircraft spray tank or vaporized thermally, is a mixt of S trioxide and chlorosulfonic acid (FS smoke agent) which upon hydrolysis forms sulfuric and hydrochloric acid dispersions. Of course, all such formulations are highly corrosive, and, if not outright toxic, then conducive to pulmonary edema... 

Schnur and co-workers " summarized typical reactions that can be performed on functional groups of substituted 2,4-oxazolidinediones without ring opening. These reactions include reduction with iron-acetic acid, chlorosulfonation, nucleophilic displacements of aromatic fluorides, and acid hydrolysis with HCl/formic acid. Nonetheless, there are examples of useful ring cleavage reactions involving 2,4-oxazolidinediones. 

Furosemide can also be synthesized starting with 2,4-dichlorobenzoic acid (formed by chlorination and oxidation of toluene). Reaction with chlorosulfonic acid is an electrophilic aromatic substitution via the species -S02C1 attacking ortho and para to the chlorines and meta to the carboxy-late. Ammonolysis to the sulfonamide is followed by nucleophilic aromatic substitution of the less hindered chlorine by furfurylamine (obtained from furfural—a product obtained by the hydrolysis of carbohydrates). 

The toluenesulfonyl chloride can first be sulfonated instead of hydrolyzed. The hydrolysis then tiuces place with the formation of chlorosulfonic acid, and when water is added after the sulfonation, hydrochloric acid is generated immediately. 

Chlorosulfonic acid also effects direct sulfonation, although when used in excess the product is the sulfonyl chloride subsequent hydrolysis leads to the acid (Scheme 5.3). 

The HjC-O-Te bonds are remarkably stable no cis-trans isomerization was observed when the hydroxy methoxy tellurium tetrafluorides were kept at temperatures below 130°. The bonds are not cleaved by 65% oleum or chlorosulfonic acid at room temperature, instead, the sulfate esters HjCO-TeF tO-SOjH) were formed. These sulfate esters were transformed to HO-TeFiCO-SOjH) upon heating to 100°. Cesium chloride dissolved in an excess of cis- or /run.s-hydroxy methoxy tellurium tetrafluoride liberated hydrogen chloride with the formation of very hygroscopic cesium methoxo(oxo)letrafluorotellurates(VI). Trunj-hydroxy methoxy tellurium tetrafluoride reacts instantaneously with water with loss of fluoride. The cu-compound is stable toward hydrolysis at room temperature. ... 

Oxo-3-pyrazolin-4-sulfonic acids (Table XXXVI) are prepared by direct sulfonation738,745 with sulfuric acid and acetic anhydride or by chlorosulfonation with chlorosulfonic acid, followed by hydrolysis to the acid.1248,1249 The reaction of 2,3-dimethyl-l-phenyl-5-oxo-3-pyrazolin-4-sulfonyl chloride with urea forms a bis(5-oxo-2-pyrazolin-4-sulfonic acid) derivative,1249 the only such bis derivative reported. Reduction of the sulfonic acid chlorides with zinc and acid forms the corresponding mercapto compound.1249... 

The reaction between cold, anhydrous H2O2 and chlorosulfonic acid yields peroxomonosulfuric acid, H2SO5, and peroxodisulfuric acid, H2S2O8 (scheme 15.108). Conversion of H2S2O8 (Table 15.8) to H2SO5 (15.54) occurs by controlled hydrolysis. 

Woodward s Reagent K. 2-Ethyl 5-m sutfophen-ylisoxazoltiim hydroxide, fit nor salt N-ethyl-5-pbenylisoxa-zolium-3 -sulfonate. CnH-.NO.S mol wt 253,29. C 52.16%, H 4.38%, N 5.53%, O 25.27%, S 12.66%. Prepd by reacting 5-phenylisoxazole with chlorosulfonic acid, followed by alkylation with triethyloxonium fluoroborate, and acid hydrolysis Woodward et ai. J. Am. Chem. Soc. 83, 1010 (I960... 

Instead of the use of sulfuryl chloride, SO2 and CI2, which combine to give sulfuryl chloride, can be employed for vapor-phase reactions. When the ratio of SO2 to CI2 is adjusted, it is feasible to produce sulfonic or chlorosulfonic acid derivatives of saturated paraffins in liquid-phase reactions. According to Lockwood and Richmond, a premixed stream of sulfur dioxide and chlorine can be used for the countercurrent photochlorination of white oil (petroleum fraction, sp gr, 0.8033 bp, 283-324 C) at about 50°C. The product, after hydrolysis with 30 per cent sodium hydroxide, yields an aqueous solution of the sodium salt of a sulfonic or chlorosulfonic acid. An increase in the ratio of SO2 to CI2 greatly increases the yield of solubilized product. When a 3 1 ratio is used, the product contains very little chlorine and has good wetting and detergent characteristics. ... 

State of the type shown in (15) is visualized, where HPO4 is a typical species HA. The hydrolysis of chlorosulfonic acid is normally very fast, but the kinetics... 

Acetylation of aniline produces acetanilide (2) and protects the amino group from the reagent to be used next. Treatment of 2 with chlorosulfonic acid brings about an electrophilic aromatic substitution reaction and yields/>-acetamidobenzene-sulfonyl chloride (3). Addition of ammonia or a primary amine gives the diamide, 4 (an amide of both a carboxylic acid and a sulfonic acid). Finally, refluxing 4 with dilute hydrochloric acid selectively hydrolyzes the carboxamide linkage and produces a sulfanilamide. (Hydrolysis of carboxamides is much more rapid than that of sulfonamides.)... 

Solubilised vat dyes (Figure 7.7) are a group of water-soluble, prereduced forms of vat dyes, stabilised as the sodium salts of sulfate esters, which are prepared via the leuco form by chlorosulfonation. These dyes may be applied directly to the cellulosic fibres and subsequently generate the vat dye within the fibres by acid hydrolysis and oxidation with hydrogen peroxide. 

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