Diethyl_sulfate

Diethyl sulfate

Diethyl sulfate

Chemical compound

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]

Quick Facts Names, Identifiers ...

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. [1]
    "DIETHYL SULFATE | CAMEO Chemicals | NOAA". cameochemicals.noaa.gov. Retrieved 2021-03-04.
  2. [2]
    "NCI Thesaurus". ncit.nci.nih.gov. Retrieved 2021-04-02.
  3. [3]
    "SAFETY DATA SHEET--Diethyl sulfate". ThermoFisher Scientific. Aug 21, 2018. Retrieved June 18, 2020.
  4. [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. [5]
    IARC (1999). "Diethyl Sulfate". Summaries and Evaluations. International Agency for Research on Cancer (IARC). p. 1405.
  6. [6]
    "NCI Thesaurus". ncit.nci.nih.gov. Retrieved 2021-02-18.
  7. [7]
    "Diethyl Sulfate" (PDF). United States Environmental Protection Agency. Archived (PDF) from the original on 2016-10-14.
  8. [8]
    "DIETHYL SULFATE | CAMEO Chemicals | NOAA". cameochemicals.noaa.gov. Retrieved 2021-04-02.
  9. [9]
    Dow (June 24, 2006). "Diethyl Sulfate" (PDF). Product Safety Assessment. Dow Chemical Company. Retrieved 2016-03-05.
  10. [10]
    PubChem. "Hazardous Substances Data Bank (HSDB) : 1636". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-03-18.

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