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Sulfination Units

Sulfination is the introduction of sulfonic acid into an organic compound. The usual sulfinating agent or sulficant is concentrated sulfuric acid but, sulfurtrioxide, chlorosulfonic acid, metallic sulfates, and sulfamic acid are also occasionally used. The name sulficants comes from these molecules moving to the surface of a liquid or to an interface between two liquids and changing the properties of the surface. However, the nature and properties of sulfuric acid, makes it desirable to use it for nucleophilic substitutions whenever possible. For each substance being suflinated, there is a critical concentration of acid below which sulfination ceases. The removal of the water form in the reaction is therefore essential. The use of a large excess of acid, while expensive, can maintain essentially constant concentration as the reaction progresses. It is not easy to volatilize water from concentrated solutions of sulfuric acid, but azeotropic distillation can sometimes help. Azeotropic distillation is the process of adding components to generate a new, lower-boiling point liquid compound or azeotrope. The sulfination reaction is exothermic but not highly corrosive, so sulfination can be conducted in stainless steel or cast iron sulfinators. A jacket heated with hot oil or steam can serve to heat the contents sufficiatently to get the reaction started, then carry away the excess heat of reaction. Sulfination reactions may be carried out in batch reactors or in continuous reactors. Continuous sulfination reactions are feasible only when the organic compounds possess certain chemical and physical properties, and are practical in only a relatively few industrial processes. Most commercial sulfination reactions are batch operations. Because they are stable, sulfonic acids can be isolated, stored, and shipped as an article of commerce. Sulfates, due to their instability are available only as neutral compounds. This stability difference in the products

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