Chlorosulfonic AcidSince its discovery in 1854, chlorosulfonic acid has demonstrated that it is a truly versatile reagent. It is widely used as a sulfonating and chlorosulfonating agent, particularly of organic compounds, and it provides useful synthetic intermediates for many branches of industry. This book provides a detailed, up to date account of the reactions of chlorosulfonic acid with aliphatic, aromatic and heterocyclic compounds; reactions with elements and inorganic compounds are also discussed, along with the use of the reagent as a powerful acid catalyst, and halogenation and dehydrating agent. Finally, the commercial uses and manufacture of chlorosulfonic acid are reviewed. The detailed coverage in this book, coupled with the many references to recent work, will ensure that it is welcomed as a reference by synthetic chemists in, for example, the pharmaceutical, agrochemical, plastic and detergent industries. Researchers and their students in academia will also find it a valuable addition to their bookshelves. |
Contents
Safety | 5 |
Sulfonation by Halosulfonic Acids | 11 |
References | 20 |
Sulfonylation | 30 |
2 | 39 |
Phenols | 61 |
Aryl Ethers | 71 |
Aromatic Amines and Related Compounds | 97 |
Reactions of Chlorosulfonic Acid with Heterocyclic | 181 |
Heterocyclic Oxygen Compounds | 199 |
Sulfur Heterocycles | 209 |
References | 222 |
Inorganic Compounds | 228 |
Commercial Uses of Chlorosulfonic Acid | 235 |
Detergents | 241 |
Blowing Agents | 252 |
Arylureas | 110 |
Reaction of Chlorosulfonic Acid with Miscellaneous Compounds | 117 |
References | 133 |
The Reaction of Chlorosulfonic Acid with Aliphatic | 146 |
Alkyl Halides | 153 |
Aliphatic Carbonyl Compounds | 160 |
References | 176 |
Cyclization | 259 |
Rearrangement | 265 |
Preparation Manufacture and Properties | 272 |
Properties | 276 |
294 | |
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Common terms and phrases
2-sulfonic 4-sulfonyl acid one equivalent acid six equivalents acid to give action of chlorosulfonic aliphatic alkenes alkyl amines anhydride aromatic atom benzene carbon carboxylic acid catalyst Chapter Chem chloroform chlorosul chlorosulfonic acid six CIO₂S CISO3H CO₂H compounds cyclization derivatives dichloromethane diphenyl disulfonyl electron-donating electron-withdrawing electrophilic Equation esters ether excess chlorosulfonic acid excess CISO3H excess of chlorosulfonic F.J. Swinbourne gave give a mixture give the corresponding heating heterocyclic hydrogen chloride Khim kinetics Kokai large excess methoxy methyl mixture of chlorosulfonic naphthalene nitrobenzene nucleophilic oleum orientation of sulfonation phenyl Phosphorus phosphorus pentachloride polymer pyridine R.J. Cremlyn reacted with chlorosulfonic reacted with excess reaction with chlorosulfonic reactive reagent ring room temperature Scheme SO₂CI SO3H sodium solvent steric substitution substrate sulfate sulfonation occurs sulfonic acid sulfonic acid group sulfonyl chloride sulfur trioxide synthesis thionyl chloride treatment with chlorosulfonic yield the corresponding