Diethyl sulfate
Molecular structure of diethyl sulfate.
Space filling molecular structure of diethyl sulfate.
Names
Preferred IUPAC name
Diethyl sulfate
Other names
Sulfuric acid diethyl ester
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.536 Edit this at Wikidata
KEGG
RTECS number
  • WS7875000
UNII
  • InChI=1S/C4H10O4S/c1-3-7-9(5,6)8-4-2/h3-4H2,1-2H3 checkY
    Key: DENRZWYUOJLTMF-UHFFFAOYSA-N checkY
  • 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
Appearance Colorless 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:
GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
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 four-colored diamondHealth 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).
checkY verify (what is checkY☒N ?)

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]

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]

References

  1. ^ a b c "DIETHYL SULFATE | CAMEO Chemicals | NOAA". cameochemicals.noaa.gov. Retrieved 2021-03-04.
  2. ^ a b c "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. ^ a b 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

External links

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