Carbyl sulfate is an

organosulfur compound Organosulfur compounds are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature abounds with organosulfur compounds—sulfu ...

. The white solid is the product of the reaction of

sulfur trioxide Sulfur trioxide (alternative spelling sulphur trioxide, also known as ''nisso sulfan'') is the chemical compound with the formula SO3. It has been described as "unquestionably the most important economically" sulfur oxide. It is prepared on an ind ...

and

ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...

. It is used in preparation of some dyes and other organosulfur compounds. Carbyl sulfate is a colorless, crystalline,

hygroscopic Hygroscopy is the phenomenon of attracting and holding water molecules via either absorption or adsorption from the surrounding environment, which is usually at normal or room temperature. If water molecules become suspended among the substance ...

substance although commercial product can appear as a liquid. Because of its unpleasant properties carbyl sulfate is difficult to handle and is usually not isolated but further processed to give secondary products.

Production

Regnault and

Heinrich Gustav Magnus Heinrich Gustav Magnus (; 2 May 1802 – 4 April 1870) was a notable German experimental scientist. His training was mostly in chemistry but his later research was mostly in physics. He spent the great bulk of his career at the University of Berl ...

"Zur Erinnerung an Gustav Magnus". Nach einem am 14. December 1870 in der General-Versammlung der Deutschen Chemischen Gesellschaft zu Berlin gehaltenen Vortrage

August Wilhelm Hofmann August Wilhelm von Hofmann (8 April 18185 May 1892) was a German chemist who made considerable contributions to organic chemistry. His research on aniline helped lay the basis of the aniline-dye industry, and his research on coal tar laid the g ...

s, Berlin, Ferd. Dümmler's Verlagsbuchhandlung, 1871 (S. 32) reported first in the years 1838 to 1839 on the compound as reaction product of anhydrous ethanol and anhydrous sulfuric acid. Carbyl sulfate is produced in the highly

exothermic In thermodynamics, an exothermic process () is a thermodynamic process or reaction that releases energy from the system to its surroundings, usually in the form of heat, but also in a form of light (e.g. a spark, flame, or flash), electricity (e ...

(about 800 kcal/kg) reaction of

and

in the vapor phase in nearly quantitative yield. : Carbylsulfat Synthese

Disulfuric acid Disulfuric acid (alternative spelling disulphuric acid) or pyrosulfuric acid (alternative spelling pyrosulphuric acid), also named oleum, is a sulfur oxoacid. It is a major constituent of fuming sulfuric acid, oleum, and this is how most chemists e ...

and

chlorosulfuric acid Chlorosulfuric acid (IUPAC name: sulfurochloridic acid) is the inorganic compound with the formula HSO3Cl. It is also known as chlorosulfonic acid, being the sulfonic acid of chlorine. It is a distillable, colorless liquid which is hygroscopic and ...

can also be used as a sulfonating agent, replacing sulfur trioxide. Instead of ethylene, ethylene-forming agents can be used, e.g.

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...

diethyl ether Diethyl ether, or simply ether, is an organic compound in the ether class with the formula , sometimes abbreviated as (see Pseudoelement symbols). It is a colourless, highly volatile, sweet-smelling ("ethereal odour"), extremely flammable liq ...

. The product of industrial processes is a water-clear liquid which has - in accordance with D.S. Breslow (107.5 to 109 °C) - a melting range from 102 to 108 °C. Previously stated melting point of about 80 °C results from adhering sulfur trioxide.

Reactions and use

As a cyclic

sulfate ester Organosulfates are a class of organic compounds sharing a common functional group with the structure R-O-SO3−. The SO4 core is a sulfate group and the R group is any organic residue. All organosulfates are formally esters derived from alcohols ...

, it is an

alkylating agent Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

. Hydrolysis affords ethionic acid, which retains one sulfate ester group. Ethionic acid undergoes further hydrolysis to isethionic acid: : Carbyl sulfate is used as precursor for

vinylsulfonic acid Vinylsulfonic acid is the organosulfur compound with the chemical formula CH2=CHSO3H. It is the simplest unsaturated sulfonic acid. The C=C double bond is a site of high reactivity. Polymerization gives polyvinylsulfonic acid, especially when ...

and sodium vinyl sulfonate, which are important activated alkenes and are used e. g. as anionic comonomers. A number of functional compounds with a variety of applications are available by nucleophilic addition at the activated double bond of the vinyl sulfonic acid and its derivatives.

Safety

The material is highly reactive. It can decompose explosively when heated above 170 °C.

Production

Reactions and use

Safety

References

Further reading