Diethyl sulfide

Diethyl sulfide is an organosulfur compound with the chemical formula (C
2H
5)
2S. It is a colorless, malodorous liquid. Although a common thioether, it has few applications.

Diethyl sulfide
Names
Preferred IUPAC name
(Ethylsulfanyl)ethane
Other names
1,1-thiobisethane, diethyl thioether, ethyl sulfide, thioethyl ether
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.934
EC Number
  • 206-526-9
KEGG
RTECS number
  • LC7200000
UNII
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 miscible
Solubility in diethyl ether miscible
−67.9·10−6 cm3/mol
1.44233
Hazards
Main hazards Skin and eye irritant. Highly flammable liquid and vapor
Safety data sheet External MSDS
R-phrases (outdated) R11 R65
S-phrases (outdated) (S2) S9 S16 S51 S62
NFPA 704 (fire diamond)
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. gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
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

Preparation

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[1] and as a constituent found in volatiles from potatoes.[2]

Reactions

Diethyl sulfide is a Lewis base, classified as a soft ligand (see also ECW model).Its relative donor strength toward a series of acids, versus other Lewis bases, can be illustrated by C-B plots.[3][4] A typical complex is cis-PtCl2(SEt2)2.

Structure of cis-PtCl2(SEt2)2.[5]

References
  1. Baldry, Jane; J. Dougan; G. E. Howard (1972). "Volatile Flavouring Constituents of Durian". Phytochemistry. 11 (6): 2081–2084. doi:10.1016/s0031-9422(00)90176-6.
  2. Gumbmann, M. R.; H. K. Burr (1964). "Food Flavors and Odors, Volatile Sulfur Compounds in Potatoes". Journal of Agricultural and Food Chemistry. 12 (5): 404–408. doi:10.1021/jf60135a004.
  3. Laurence, C. and Gal, J-F. Lewis Basicity and Affinity Scales, Data and Measurement, (Wiley 2010) pp 50-51 IBSN 978-0-470-74957-9
  4. Cramer, R. E.; Bopp, T. T. (1977). "Graphical display of the enthalpies of adduct formation for Lewis acids and bases". Journal of Chemical Education. 54: 612–613. doi:10.1021/ed054p612. The plots shown in this paper used older parameters. Improved E&C parameters are listed in ECW model.
  5. C.Hansson (2007). "cis-Dichloridobis(diethyl sulfide-κS)platinum(II) at 295 and 150 K". Acta Crystallographica Section C. 63 (Pt 8): m361-3. doi:10.1107/S0108270107030417. PMID 17675684.
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