Diethyl sulfate

Last updated
Diethyl sulfate
Diethylsulfate V 2.png
Diethyl-sulfate-3D-balls-by-AHRLS.png
Names
Preferred IUPAC name
Diethyl sulfate
Other names
Sulfuric acid diethyl ester
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.536 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
RTECS number
  • WS7875000
UNII
  • InChI=1S/C4H10O4S/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3 Yes check.svgY
    Key: DENRZWYUOJLTMF-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H10O4S/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3
    Key: DENRZWYUOJLTMF-UHFFFAOYAR
  • O=S(=O)(OCC)OCC
Properties
C4H10O4S
Molar mass 154.18 g·mol−1
AppearanceColorless liquid
Density 1.2 g/mL
Melting point −25 °C (−13 °F; 248 K)
Boiling point 209 °C (408 °F; 482 K) (decomposes)
decomposes in water
Vapor pressure 0.29 mm Hg
-86.8·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg
Danger
H302, H312, H314, H332, H340, H350
P201, P202, P260, P261, P264, P270, P271, P280, P281, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P308+P313, P310, P312, P321, P322, P330, P363, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
1
1
Flash point 104 °C (219 °F; 377 K)
Related compounds
Related compounds
 Dimethyl sulfate; diethyl sulfite
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Diethyl sulfate (DES) is a highly toxic, combustible, and likely carcinogenic chemical compound with the formula (C2H5)2SO4. [1] It occurs as a colorless, oily liquid with a faint peppermint odor and is corrosive to tissue and metals. [2] [1] Diethyl sulfate is used as an alkylating agent to prepare ethyl derivatives of phenols, amines, and thiols. It is used to manufacture dyes and textiles. [2]

Contents

Property

Diethyl sulfate is moisture sensitive liquid. Heating can lead to release of toxic gases and vapors. [3] It gets darker over time. [2] It forms ethyl alcohol, ethyl sulfate, and eventually sulfuric acid when exposed to water. This compound is also combustible; when burned, sulfur oxides, ether, and ethylene are produced. [1]

Toxicity

Diethyl sulfate is a strong alkylating agent which ethylates DNA, causing both somatic and germ cell mutations, and is therefore genotoxic. [4] According to the International Agency for Research on Cancer (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. [5] Experimentation with animals has suggested this compound is likely carcinogenic to humans as it was implicated in the development of laryngeal cancer. [6] Evidence of the effects of this chemical compound on reproductive or developmental health is also lacking. [7]

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. [8]

Preparation

Diethyl sulfate can be prepared by the reaction of oleum with diethyl ether or ethanol, after which the product is purified by vacuum distillation. [9] Another method involves dissolving ethylene in concentrated sulfuric acid. [9] Diethyl sulfate is produced commercially at scale and is sold by a variety of chemical suppliers. [10]

Related Research Articles

<span class="mw-page-title-main">Ethylene</span> Hydrocarbon compound (H₂C=CH₂)

Ethylene is a hydrocarbon which has the formula C2H4 or H2C=CH2. It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene.

<span class="mw-page-title-main">Ethanol</span> Organic compound (CH₃CH₂OH)

Ethanol is an organic compound with the chemical formula CH3CH2OH. It is an alcohol, with its formula also written as C2H5OH, C2H6O or EtOH, where Et stands for ethyl. Ethanol is a volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. It is a psychoactive recreational drug, and the active ingredient in alcoholic drinks.

Acetaldehyde (IUPAC systematic name ethanal) is an organic chemical compound with the formula CH3CHO, sometimes abbreviated by chemists as MeCHO. It is a colorless liquid or gas, boiling near room temperature. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale in industry. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants. It is also produced by the partial oxidation of ethanol by the liver enzyme alcohol dehydrogenase and is a contributing cause of hangover after alcohol consumption. Pathways of exposure include air, water, land, or groundwater, as well as drink and smoke. Consumption of disulfiram inhibits acetaldehyde dehydrogenase, the enzyme responsible for the metabolism of acetaldehyde, thereby causing it to build up in the body.

<span class="mw-page-title-main">Chloroethane</span> Chemical compound commonly known as ethyl chloride

Chloroethane, commonly known as ethyl chloride, is a chemical compound with chemical formula CH3CH2Cl, once widely used in producing tetraethyllead, a gasoline additive. It is a colorless, flammable gas or refrigerated liquid with a faintly sweet odor.

<span class="mw-page-title-main">Alkylation</span> Transfer of an alkyl group from one molecule to another

Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene. Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents.

<span class="mw-page-title-main">Diethyl malonate</span> Chemical compound

Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odour, and is used in perfumes. It is also used to synthesize other compounds such as barbiturates, artificial flavourings, vitamin B1, and vitamin B6.

<span class="mw-page-title-main">Propylene oxide</span> Chemical compound

Propylene oxide is an acutely toxic and carcinogenic organic compound with the molecular formula CH3CHCH2O. This colourless volatile liquid with an odour similar to ether, is produced on a large scale industrially. Its major application is its use for the production of polyether polyols for use in making polyurethane plastics. It is a chiral epoxide, although it is commonly used as a racemic mixture.

<span class="mw-page-title-main">Ethanethiol</span> Chemical compound

Ethanethiol, commonly known as ethyl mercaptan, is an organosulfur compound with the formula CH3CH2SH. is a colorless liquid with a distinct odor. Abbreviated EtSH, it consists of an ethyl group (Et), CH3CH2, attached to a thiol group, SH. Its structure parallels that of ethanol, but with sulfur in place of oxygen. The odor of EtSH is infamous. Ethanethiol is more volatile than ethanol due to a diminished ability to engage in hydrogen bonding. Ethanethiol is toxic in high concentrations. It occurs naturally as a minor component of petroleum, and may be added to otherwise odorless gaseous products such as liquefied petroleum gas (LPG) to help warn of gas leaks. At these concentrations, ethanethiol is not harmful.

<span class="mw-page-title-main">Nitrobenzene</span> Chemical compound

Nitrobenzene is an organic compound with the chemical formula C6H5NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor to aniline. In the laboratory, it is occasionally used as a solvent, especially for electrophilic reagents.

<span class="mw-page-title-main">Diethyl ether</span> Organic chemical compound

Diethyl ether, or simply ether, is an organic compound in the ether class with the formula C4H10O or (C2H5)2O, sometimes abbreviated as Et2O. It is a colourless, highly volatile, sweet-smelling, extremely flammable liquid. It is commonly used as a solvent in laboratories and as a starting fluid for some engines. It was formerly used as a general anesthetic, until non-flammable drugs were developed, such as halothane. It has been used as a recreational drug to cause intoxication.

Substances, mixtures, and exposure circumstances in this list have been classified as group 1 by the International Agency for Research on Cancer (IARC): The agent (mixture) is carcinogenic to humans. The exposure circumstance entails exposures that are carcinogenic to humans. This category is used when there is sufficient evidence of carcinogenicity in humans. Exceptionally, an agent (mixture) may be placed in this category when evidence of carcinogenicity in humans is less than sufficient. Still, there is sufficient evidence of carcinogenicity in experimental animals and strong evidence in exposed humans that the agent (mixture) acts through a relevant mechanism of carcinogenicity.

The agents in this list have been classified in group 2A by the International Agency for Research on Cancer (IARC). The term "agent" encompasses both substances and exposure circumstances that pose a risk. This designation is applied when there is limited evidence of carcinogenicity in humans as well as sufficient evidence of carcinogenicity in experimental animals. In some cases, an agent may be classified in this group when there is inadequate evidence of carcinogenicity in humans along with sufficient evidence of carcinogenicity in experimental animals and strong evidence that the carcinogenesis is mediated by a mechanism that also operates in humans. Exceptionally, an agent may be classified in this group solely on the basis of limited evidence of carcinogenicity in humans.

<span class="mw-page-title-main">Dimethyl sulfate</span> Chemical compound

Dimethyl sulfate (DMS) is a chemical compound with formula (CH3O)2SO2. As the diester of methanol and sulfuric acid, its formula is often written as (CH3)2SO4 or Me2SO4, where CH3 or Me is methyl. Me2SO4 is mainly used as a methylating agent in organic synthesis.

<span class="mw-page-title-main">Ethyl sulfate</span> Chemical compound

Ethyl 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.

Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odor.

This is the list of extremely hazardous substances defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act. The list can be found as an appendix to 40 C.F.R. 355. Updates as of 2006 can be seen on the Federal Register, 71 FR 47121.

<span class="mw-page-title-main">Ethyl acrylate</span> Chemical compound

Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.

<span class="mw-page-title-main">Ethyl propionate</span> Chemical compound

Ethyl propionate is an organic compound with formula C2H5O2CCH2CH3. It is the ethyl ester of propionic acid. It is a colorless volatile liquid with a pineapple-like odor. Some fruits such as kiwis and strawberries contain ethyl propionate in small amounts.

<span class="mw-page-title-main">Cadmium tetrafluoroborate</span> Chemical compound

Cadmium tetrafluoroborate is an ionic, chemical compound with the formula Cd(BF4)2. It is a crystalline solid, which is colorless and odorless. Cadmium tetrafluoroborate is most frequently used in the industrial production of high-strength steels, its purpose being to prevent hydrogen absorption, a source of post-production cracking of the metal, in the treated steels. Another application of the chemistry of cadmium tetrafluoroborate is fine tuning of the size of cadmium telluride nanomaterials.

<span class="mw-page-title-main">Carbyl sulfate</span> Chemical compound

Carbyl sulfate is an organosulfur compound. The white solid is the product of the reaction of sulfur trioxide and ethylene. It is used in preparation of some dyes and other organosulfur compounds. Carbyl sulfate is a colorless, crystalline, hygroscopic 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.

References

  1. 1 2 3 "DIETHYL SULFATE | CAMEO Chemicals | NOAA". cameochemicals.noaa.gov. Retrieved 2021-03-04.
  2. 1 2 3 "NCI Thesaurus". ncit.nci.nih.gov. Retrieved 2021-04-02.
  3. ↑ "SAFETY DATA SHEET--Diethyl sulfate". ThermoFisher Scientific. Aug 21, 2018. Retrieved June 18, 2020.
  4. ↑ "Agents Classified by the IARC Monographs, Volumes 1–129 – IARC Monographs on the Identification of Carcinogenic Hazards to Humans". monographs.iarc.who.int. Retrieved 2021-04-02.
  5. ↑ IARC (1999). "Diethyl Sulfate". Summaries and Evaluations. 71. International Agency for Research on Cancer (IARC): 1405.{{cite journal}}: Cite journal requires |journal= (help)
  6. ↑ "NCI Thesaurus". ncit.nci.nih.gov. Retrieved 2021-02-18.
  7. ↑ "Diethyl Sulfate" (PDF). United States Environmental Protection Agency. Archived (PDF) from the original on 2016-10-14.
  8. ↑ "DIETHYL SULFATE | CAMEO Chemicals | NOAA". cameochemicals.noaa.gov. Retrieved 2021-04-02.
  9. 1 2 Dow (June 24, 2006). "Diethyl Sulfate" (PDF). Product Safety Assessment. Dow Chemical Company. Retrieved 2016-03-05.{{cite journal}}: Cite journal requires |journal= (help)
  10. ↑ PubChem. "Hazardous Substances Data Bank (HSDB) : 1636". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-03-18.

Further reading

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