Diethyl sulfide

Diethyl sulfide
Names
IUPAC name
1,1-Thiobisethane
Other names
diethyl thioether, ethyl sulfide, thioethyl ether
Identifiers
352-93-2 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:27710 YesY
ChEMBL ChEMBL117181 YesY
ChemSpider 9233 YesY
ECHA InfoCard 100.005.934
EC Number 206-526-9
KEGG C14706 YesY
PubChem 6163
RTECS number LC7200000
Properties
C4H10S
Molar mass 90.19
Appearance Clear liquid
Density 0.837 g/cm3
Melting point −103.8 °C (−154.8 °F; 169.3 K)
Boiling point 92 °C (198 °F; 365 K)
insoluble
Solubility in ethanol fully miscible
Solubility in diethyl ether fully miscible
1.44233
Hazards
Main hazards Skin and eye irritant. Highly flammable liquid and vapor
Safety data sheet External MSDS
R-phrases R11 R65
S-phrases (S2) S9 S16 S51 S62
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
3
2
1
Flash point −10 °C (14 °F; 263 K)
Related compounds
Related thioethers
 dimethyl sulfide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Diethyl sulfide is a clear flammable chemical compound with a pungent garlic-like odor. It has the chemical formula C
4H
10S, though it can also be written (C
2H
5)
2S or Et
2S to make its chemical structure more clear. It is prepared by treating ethanol with concentrated sulfuric acid, partially neutralizing the new solution with sodium carbonate, then distilling the resulting sodium ethyl sulfate in a solution containing potassium sulfide.[1]

Diethyl sulfide is a by-product of the commercial production of ethanethiol, which is prepared by the reaction of ethylene with hydrogen sulfide over an alumina-based catalyst. The amount of diethyl sulfide produced can be controlled by varying the ratio of hydrogen sulfide to ethylene.

Occurrence

Diethyl sulfide has been found to be a constituent of the odor of durian fruit[2] and as a constituent found in volatiles from potatoes.[3]

Uses

Diethyl sulfide is used as a solvent for anhydrous minerals and in plating baths for gold and silver.[1]

References

  1. 1 2 Merck index of Chemicals and Drugs, 9th ed., monograph 3801
  2. ↑ Baldry, Jane; J. Dougan; G. E. Howard (1972). "Volatile Flavouring Constituents of Durian". Phytochemistry. 11: 2081–2084. doi:10.1016/s0031-9422(00)90176-6.
  3. ↑ Gumbmann, M. R.; H. K. Burr (1964). "Volatile Sulfur Compounds in Potatoes". Journal of Food and Agricultural Chemistry. 12: 404–408. doi:10.1021/jf60135a004.
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