Diethyl sulfate (DES) is a highly

toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...

combustible A combustible material is something that can burn (i.e., ''combust'') in air. A combustible material is flammable if it ignites easily at ambient temperatures. In other words, a combustible material ignites with some effort and a flammable mat ...

, and likely

carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substan ...

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...

(C₂H₅)₂SO_4. It occurs as a colorless, oily liquid with a faint

peppermint Peppermint (''Mentha'' × ''piperita'') is a hybrid species of mint, a cross between watermint and spearmint. Indigenous to Europe and the Middle East, the plant is now widely spread and cultivated in many regions of the world.Euro+Med Plantbas ...

odor and is corrosive to tissue and metals. Diethyl sulfate is used as 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 ...

to prepare

ethyl Ethyl may refer to: Arts and entertainment * Cold Ethyl, a Swedish rock band *Ethyl Sinclair, a character in the ''Dinosaurs'' television show Science and technology * Ethyl group, an organic chemistry moiety * Ethyl alcohol (or ethanol) * E ...

derivatives of

phenol Phenol (also called carbolic acid) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile. The molecule consists of a phenyl group () bonded to a hydroxy group (). Mildly acidic, it req ...

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituen ...

s, and

thiol In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl gro ...

s. It is used to manufacture dyes and textiles.

Property

Diethyl sulfate is moisture sensitive liquid. Heating can lead to release of toxic gases and vapors. It gets darker over time. It forms ethyl

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

ethyl sulfate Ethyl sulfate (IUPAC name: ethyl hydrogen sulfate), also known as sulfovinic acid, is an organic chemical compound used as an intermediate in the production of ethanol from ethylene. It is the ethyl ester of sulfuric acid. History This substance ...

, and eventually

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

when exposed to

water Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as a ...

. This compound is also combustible; when burned,

sulfur oxides Sulfur oxide refers to many types of sulfur and oxygen containing compounds such as SO, SO2, SO3, S7O2, S6O2, S2O2, etc. Sulfur oxide (SO''x'') refers to one or more of the following: * Lower sulfur oxides (S''n''O, S7O2 and S6O2) * Sulfur monox ...

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 c ...

, 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 ...

are produced.

Toxicity

Diethyl sulfate is a strong

which ethylates DNA, causing both somatic and germ cell mutations, and is therefore

genotoxic Genotoxicity is the property of chemical agents that damage the genetic information within a cell causing mutations, which may lead to cancer. While genotoxicity is often confused with Mutagen, mutagenicity, all mutagens are genotoxic, but some geno ...

. According to the

International Agency for Research on Cancer The International Agency for Research on Cancer (IARC; french: Centre International de Recherche sur le Cancer, CIRC) is an intergovernmental agency forming part of the World Health Organization of the United Nations. Its role is to conduct and ...

(IARC), as of 1999 there is not sufficient evidence for the carcinogenic properties of diethyl sulfate in humans, but there is in animals. It is classified as a Group 2A (probably carcinogenic to humans) carcinogen by the IARC. Experimentation with animals has suggested this compound is likely carcinogenic to humans as it was implicated in the development of laryngeal cancer. Evidence of the effects of this chemical compound on reproductive or developmental health is also lacking. Inhalation of this chemical compound has potential to be fatal and can induce nausea or vomiting. Swallowing this substance could also be fatal or lead to nausea, vomiting, or severe abdominal pain. Contact with or absorption through the skin also has potential to be fatal, and can cause severe burns.

Preparation

This compound can be prepared by absorbing ethylene into concentrated sulfuric acid or by fuming sulfuric acid into diethyl ether or ethanol and is purified using rectification in vacuo. This can be done on a large enough scale for commercial production. It can then be purchased as a technical product or for use in a laboratory setting with 99.5% purity or 95% to 98% purity respectively.

References

External links

* * * {{ cite journal , url = http://monographs.iarc.fr/ENG/Monographs/vol71/mono71-92.pdf , year = 1992 , volume = 71 , publisher = IARC , series = IARC Monographs , title = Diethyl sulfate Ethylating agents IARC Group 2A carcinogens Ethyl esters Sulfate esters

Property

Toxicity

Preparation

References

Further reading

External links