Organosulfate

Organosulfates are a class of organic compounds sharing a common functional group with the general structure R-O-SO2-O-R'. The SO4 core is a sulfate group and the R groups is any organic residue. Often R' is a proton or an negative charge. These compounds are formally esters of alcohols and sulfuric acid, although many are not prepared in this way. Many sulfate esters are used in detergents and some are useful reagents.

Synthetic sulfate esters
Simple organosulfates are diethyl sulfate and dimethyl sulfate. These colourless liquids are useful alkylating agents in organic synthesis. Sodium lauryl sulfate is a useful detergent derived from lauryl alcohol and chlorosulfuric acid. It has the formula C12H25OSO3Na. Also common in consumer products are the sulfate esters of ethoxylated fatty alcohols. An example is sodium laureth sulfate, which is an ingredient in some cosmetics.

Preparation
Some alcohols react with sulfuric acid to give dialkyl sulfates. Many monoorganosulfates are prepared by reaction of chlorosulfuric acid with alcohols:
 * ClSO3H +  ROH   →    ROSO3H  +  HCl

Some organosulfates can be prepared by the Elbs persulfate oxidation of phenols and the Boyland-Sims oxidation of anilines.

Natural sulfate esters
The reduction of sulfate in nature involves the formation of one or sometimes two sulfate esters, adenosine 5'-phosphosulfate (APS) and 3'-phosphoadenosine-5'-phosphosulfate (PAPS). Sulfate is an inert anion, so nature activates it by the formation of these ester derivatives, which are susceptible to reduction to sulfite. Many organisms utilize these reactions for metabolic purposes or for the biosynthesis of sulfur compounds required for life.