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

organic chemical In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

compound Compound may refer to: Architecture and built environments * Compound (enclosure), a cluster of buildings having a shared purpose, usually inside a fence or wall ** Compound (fortification), a version of the above fortified with defensive struc ...

used as an intermediate in the production of

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

from ethylene. It is the ethyl

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...

of sulfuric acid.

History

This substance was studied contemporaneously with

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be ...

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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 scientist trained in the study of chemistry. Chemists study the composition of matter and its properties. Chemists carefully describe t ...

s Fourcroy in 1797 and

Gay-Lussac Joseph Louis Gay-Lussac (, , ; 6 December 1778 – 9 May 1850) was a French chemist and physicist. He is known mostly for his discovery that water is made of two parts hydrogen and one part oxygen (with Alexander von Humboldt), for two laws ...

in 1815. Swiss

scientist A scientist is a person who conducts scientific research to advance knowledge in an area of the natural sciences. In classical antiquity, there was no real ancient analog of a modern scientist. Instead, philosophers engaged in the philosoph ...

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

and pharmacist 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 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 li ...

from sulfuric acid and

. Further studies by the German chemist

Eilhard Mitscherlich Eilhard Mitscherlich (; 7 January 179428 August 1863) was a German chemist, who is perhaps best remembered today for his discovery of the phenomenon of crystallographic isomorphism in 1819. Early life and work Mitscherlich was born at Neuende ...

and the Swedish chemist

Jöns Berzelius Jöns is a Swedish given name and a surname. Notable people with the given name include: * Jöns Jacob Berzelius (1779–1848), Swedish chemist * Jöns Budde (1435–1495), Franciscan friar from the Brigittine monastery in NaantaliVallis Grati ...

suggested sulfuric acid was acting as a

catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

, 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 electrical potential difference, as a measurable and quantitative phenomenon, and identifiable chemical change, with the potential difference as an outco ...

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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 and

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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 elements for t ...

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 (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...

was produced primarily by the sulfuric acid hydration process in which ethylene is reacted with sulfuric acid 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, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolys ...

, but this method has been mostly replaced by direct

hydration Hydration may refer to: * Hydrate, a substance that contains water * Hydration enthalpy, energy released through hydrating a substance * Hydration reaction, a chemical addition reaction where a hydroxyl group and proton are added to a compound * ...

of ethylene. Ethyl sulfate can be produced in a laboratory setting by reacting

with sulfuric acid 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. :CH₃CH₂OH + H₂SO₄ → CH₃-CH₂-O-SO₃H + H₂O 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 sulfuric acid, which involves

protonation In chemistry, protonation (or hydronation) is the adding of a proton (or hydron, or hydrogen cation), (H+) to an atom, molecule, or ion, forming a conjugate acid. (The complementary process, when a proton is removed from a Brønsted–Lowry acid ...

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, p ...

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 Potassium carbonate is the inorganic compound with the formula K2 CO3. It is a white salt, which is soluble in water. It is deliquescent, often appearing as a damp or wet solid. Potassium carbonate is mainly used in the production of soap and gl ...

forms potassium ethyl sulfate and

potassium bicarbonate Potassium bicarbonate (IUPAC name: potassium hydrogencarbonate, also known as potassium acid carbonate) is the inorganic compound with the chemical formula KHCO3. It is a white solid. Production and reactivity It is manufactured by treating an ...

. :CH₃-CH₂-O-SO₃H + K₂CO₃ → CH₃-CH₂-O-SO₃K + KHCO₃

References

{{DEFAULTSORT:Ethyl Sulfate Ethyl esters Sulfate esters

History

Production

Reactions

Salts

See also

References