sulfateester

A sulfate ester is an ester of sulfuric acid. In organic terms, it is formed when an alcohol is esterified with sulfuric acid, producing monoesters such as alkyl hydrogen sulfates (R-O-SO3H) and diesters such as dialkyl sulfates (R-O-S(=O)2-O-R'). The characteristic functional group is the OSO3 moiety, with sulfur in the +6 oxidation state. Representations commonly take the form R-O-S(=O)2-O-R' for diesters, and R-O-SO3H for monoesters.

Common examples include ethyl sulfate (ethyl hydrogen sulfate), phenyl sulfate, and the industrially important dialkyl sulfates such as dimethyl sulfate and diethyl sulfate. Dimethyl sulfate, for instance, has the structure CH3-O-S(=O)2-O-CH3 and is a potent alkylating agent. Sulfate esters also occur in nature and industry; sodium lauryl sulfate is a widely used sulfate ester surfactant derived from lauryl alcohol.

Preparation and interconversion: sulfate esters are typically prepared by reacting alcohols with sulfuric acid or with reagents that generate the sulfate group, such as chlorosulfonic acid or sulfur trioxide, under controlled conditions. They can also be formed from alcohols and sulfuric acid in the presence of a dehydrating agent. In many cases, they can be hydrolyzed back to the alcohol and inorganic sulfate or bisulfate under acidic or basic conditions.

Reactivity and applications: sulfate esters act as leaving groups in various substitution reactions and are important in biology, where many enzymes remove sulfate groups from molecules (sulfatases). They are also encountered in detergents and other industrial products, with sodium lauryl sulfate being a prominent example. Safety considerations are essential for reactive dialkyl sulfates, which are highly toxic and potentially carcinogenic.