Sulfonation reagents

In Japan, sulfamic acid is produced and suppHed in crystal form. It is packaged in 25-kg net weight paper bags and in 600-kg, 700-kg, and 750-kg resinous dexible containers. The tmddoad price (fob Japan) is 1—2/kg. Three principal uses of sulfamic acid are in chemical cleaning, as sulfonation reagent, and for use in synthetic sweetener. 

Table 5. Composition of Sulfuric Acid, Oleum, and Liquid SO Sulfonating Reagents...

Table 6. Comparison of Sulfuric Acid and Gaseous SO Sulfonation Reagents for Sulfonating Aromatic Hydrocarbons ...

Sulfonated polyalkenes were prepared by using a triethyl phosphate—sulfur trioxide complex as the sulfonating reagent along with a solvent at low temperature. Sulfonation takes place at the a-position of the double bond with no cross-linking (222). 

The sulfonation of LAB can be carried out with concentrated sulfuric acid, oleum, or sulfur trioxide (S03). With the first two sulfonation reagents large quantities of waste sulfuric acid are obtained, which must be disposed of or processed further. Therefore the use of S03 is preferred. Special reactions were developed for sulfonation using S03 (Table 13). For sulfonation in batch pro-... 

The sulfonation reagents, which control the sulfonation technology, are... 

Aromatic compounds, 13 108-109 13 680. See also Aromatics acylation of, 12 173-181 amination of, 12 184 arylation of, 12 170-171 Cycloalkylation of, 12 169 in diesel fuel, 12 425 formylation of, 12 178 Friedel-Crafts acylation of, 12 174 Friedel-Crafts alkylation of, 12 164 nitration of, 12 182-183 oxidative coupling of, 19 654 sulfonation of, 12 181 sulfonation reagents for, 23 521-524 Aromatic-containing polymers, sulfonation of, 23 535-536... 

Indirect sulfonating reagents, 23 522-523t Indirect vacuum gauges, 20 657 Indirect (French) zinc oxide process, 26 612-613 Indisan, 24 498... 

Sulfonated styrene-divylbenzene copolymers. See Styrene-divinylbenzene copolymers, sulfonated Sulfonate moeities, incorporation into polymers, 23 534, 535 Sulfonate surfactants, 24 146 Sulfonating reagents composition of, 23 520t indirect, 23 522-523t Sulfonation, 9 273-275, 313, 23 513-536, 12 181... 

Sulfonation reaction profiles, 23 548—549 Sulfonation reagents, highly acidic, 23 539 Sulfonation-sulfation systems, 23 544 Sulfonation/sulfation processes, 23 513-563. See also Sulfation entries Sulfonation entries selection of and options for, 23 515 Sulfonation technology, uses for, 23 514-516... 

The complexes of sulfur trioxide with various nucleophiles (dioxane, pyridine etc.) are mild sulfonating reagents. Unlike other complexes of sulfur trioxide, dimethyl sulfide-sulfur trioxide readily adds to conjugated multiple bonds. Consequently, not only the sulfo group but also the dimethyl sulfide group add at the multiple bond. The reactions of dimethyl sulfide-sulfur trioxide complex with butadiene, isoprene and 2,3-dimethylbutadiene take place as conjugated l,4- -additions of dimethyl sulfide and sulfonate groups at the double bonds of the diene (equation 103).124... 

In a different study, anthracene, phenanthrene, perylene 93 (Fig. 31), and 2,7-di-tert-butylpyrene underwent regioselective oxidative-substitution reactions with iodine(III) sulfonate reagents in dichloromethane to give the corresponding aryl sulfonate esters. The use of [hydroxy(tosyloxy)iodo]benzene, in conjunction with trimethylsilyl isothiocyanate, led to thiocyanation of the PAH nucleus. 

The material is produced from naphthalene by oleum or sulfur trioxide sulfonation under conditions conducive to the formation of the h sulfonate. Subsequent reaction with formaldehyde leads to polymerization and the sulfonic acid is neutralized with sodium hydroxide [17] or lime. The process is illustrated in Fig. 2.2. The value of n is typically low but conditions are chosen to get a proportion of higher-molecular-weight product as it is believed to be more effective [18]. The quantity of sodium sulfate by-product formed by the neutralization of excess sulfonating reagent will vary depending on the process used, but can be reduced by a subsequent precipitation process using lime [19]. 

Pyridine iV-sulfides are known only in the form of their derivatives. Thus, 1-arylthiopyridinium cations (from pyridine and sulfenyl chloride) react with KCN to form ArSCN and pyridine (81CC703). Pyridine-sulfur trioxide is a mild sulfonating reagent, used for sulfonation of furan and pyrrole. 

The authors of this work were able to carry out iodination only when they used iodine monochloride. Compound 233 is unstable when stored in air and loses iodine quite rapidly. We were unable to isolate reaction products in the case of sulfonation with sulpfuric acid. The most convenient sulfonating reagent was a solution of sulfur trioxide in dichlorethane. The sulfonic derivative 234 was very hygroscopic and was further converted into the disodium or bis(isobutylammonium) salt. 

Selective sulfonylation of 1 A/i -tri-O-tritylsucrose (activated by Bu2SnO) with methanesulfonyl chloride in benzene afforded the 3-mesylated derivative, whereas the same process performed in toluene surprisingly provided the 4-mesylate in 50% yield. If triflic anhydride is used as the sulfonating reagent, the 4-triflate was obtained in 40% yield (Scheme 12).153... 

Classical approaches to chemical enzyme modification, however, often suffer from lack of regio-selectivity, which can yield heterogeneous and irreproducible enzyme mixtures. For example, preparation of methyl-chymotrypsin, -subtilisin or -trypsin using methyl sulfonate reagents, originally used to methylate the histidine of the... 

Pyridine-sulfur trioxide is a mild sulfonating reagent, which has been used for sulfonation of furan and pyrrole. 

Sulfon acid blue R, 218 Sulforation general, 6, 82 vessels, 101, 105 Sulfone reagent, 185, 211, 243 Sulfones, 85 Sulfonic adds rearrangement, 82 separation, 31 l-p-Sulfophenyl-3-methyl-5-pyrazolone, 129 Sulfoxylate, 80 Sulfur black T, 102, 337 Sulfur fusions, 332 Sulfuric add, heat capadty, 70 Sulfuryl chloride, 67, 145 Sun yellow G, 296 Superheater, 142... 

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