Ethyl sulfate (IUPAC name: ethyl hydrogen sulfate), also known as sulfovinic acid, is an

organic chemical Some chemical authorities define an organic compound as a chemical compound that contains a Carbon–hydrogen bond, carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. F ...

compound used as an intermediate in the production of

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

from ethylene. It is the ethyl

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

of sulfuric acid.

History

This substance was studied contemporaneously with ether by German alchemist August Siegmund Frobenius in 1730, subsequently by French

chemist A chemist (from Greek ''chēm(ía)'' alchemy; replacing ''chymist'' from Medieval Latin ''alchemist'') is a graduated scientist trained in the study of chemistry, or an officially enrolled student in the field. Chemists study the composition of ...

s Fourcroy in 1797 and Gay-Lussac in 1815.

Swiss Swiss most commonly refers to: * the adjectival form of Switzerland * Swiss people Swiss may also refer to: Places * Swiss, Missouri * Swiss, North Carolina * Swiss, West Virginia * Swiss, Wisconsin Other uses * Swiss Café, an old café located ...

scientist A scientist is a person who Scientific method, researches to advance knowledge in an Branches of science, area of the natural sciences. In classical antiquity, there was no real ancient analog of a modern scientist. Instead, philosophers engag ...

Nicolas-Théodore de Saussure also studied it in 1807. In 1827, French

and

pharmacist A pharmacist, also known as a chemist in English in the Commonwealth of Nations, Commonwealth English, is a healthcare professional who is knowledgeable about preparation, mechanism of action, clinical usage and legislation of medications in ...

Félix-Polydore Boullay (1806-1835) along with Jean-Baptiste André Dumas noted the role of ethyl sulfate in the preparation of

diethyl ether Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...

from

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid (English in the Commonwealth of Nations, Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, ...

and

. Further studies by the German chemist Eilhard Mitscherlich and the Swedish chemist Jöns Berzelius suggested sulfuric acid was acting as a catalyst, this eventually led to the discovery of sulfovinic acid as an intermediate in the process. The advent of

electrochemistry Electrochemistry is the branch of physical chemistry concerned with the relationship between Electric potential, electrical potential difference and identifiable chemical change. These reactions involve Electron, electrons moving via an electronic ...

by Italian

physicist A physicist is a scientist who specializes in the field of physics, which encompasses the interactions of matter and energy at all length and time scales in the physical universe. Physicists generally are interested in the root or ultimate cau ...

Alessandro Volta Alessandro Giuseppe Antonio Anastasio Volta (, ; ; 18 February 1745 – 5 March 1827) was an Italian chemist and physicist who was a pioneer of electricity and Power (physics), power, and is credited as the inventor of the electric battery a ...

and English

Humphry Davy Sir Humphry Davy, 1st Baronet (17 December 177829 May 1829) was a British chemist and inventor who invented the Davy lamp and a very early form of arc lamp. He is also remembered for isolating, by using electricity, several Chemical element, e ...

in the 1800s confirmed ether and water were formed by the reaction of sub-stoichiometric amounts of sulfuric acid on ethanol and that sulfovinic acid was formed as an intermediate in the reaction.

Production

Ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

was produced primarily by the sulfuric acid hydration process in which ethylene is reacted with

to produce ethyl sulfate followed by

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

, but this method has been mostly replaced by direct hydration of ethylene. Ethyl sulfate can be produced in a laboratory setting by reacting

with

under a gentle boil, while keeping the reaction below 140 °C. The sulfuric acid must be added dropwise or the reaction must be actively cooled because the reaction itself is highly exothermic. : If the temperature exceeds 140 °C, the ethyl sulfate product tends to react with residual ethanol starting material, producing

. If the temperature exceeds 170 °C in a considerable excess of sulfuric acid, the ethyl sulfate breaks down into ethylene and sulfuric acid.

Reactions

The mechanism of the formation of ethyl sulfate,

, and ethylene is based on the reaction between ethanol and

, which involves protonation of the ethanolic oxygen to form the oxonium ion. Ethyl sulfate accumulates in hair after chronic alcohol consumption and its detection can be used as a

biomarker In biomedical contexts, a biomarker, or biological marker, is a measurable indicator of some biological state or condition. Biomarkers are often measured and evaluated using blood, urine, or soft tissues to examine normal biological processes, ...

for alcohol consumption.

Salts

Ethyl sulfate can exist in salt forms, such as sodium ethyl sulfate, potassium ethyl sulfate, and calcium ethyl sulfate. The salt can be formed by adding the according carbonate, or bicarbonate salt. As an example, ethyl sulfate and potassium carbonate forms potassium ethyl sulfate and potassium bicarbonate. :

References

{{DEFAULTSORT:Ethyl Sulfate Ethyl esters Sulfate esters Recreational drug metabolites

History

Production

Reactions

Salts

See also

References