Ethanethiol

Source: Wikipedia, the free encyclopedia.
"EtSH" redirects here. For the ICAO code, see Holzdorf Air Base.
Ethanethiol[1][2]
Skeletal structure of ethanethiol
Ball-and-stick model of the ethanethiol molecule
Names
Preferred IUPAC name
Ethanethiol
Other names
Ethyl mercaptan
Mercaptoethane
Ethyl sulfhydrate
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
ECHA InfoCard
 100.000.762 Edit this at Wikidata
EC Number
  • 200-837-3
RTECS number
  • KI9625000
UNII
UN number 2363
  • InChI=1S/C2H6S/c1-2-3/h3H,2H2,1H3 checkY
    Key: DNJIEGIFACGWOD-UHFFFAOYSA-N checkY
  • InChI=1/C2H6S/c1-2-3/h3H,2H2,1H3
    Key: DNJIEGIFACGWOD-UHFFFAOYAW
  • CCS
Properties
C2H6S
Molar mass 62.13404 g·mol−1
Appearance Colorless liquid[3]
Odor Rotten cabbage, flatulence, skunk-like[3]
Density 0.8617 g·cm−3
Melting point −148 °C (−234 °F; 125 K)
Boiling point 35 °C (95 °F; 308 K)
0.7% (20 °C)[3]
Vapor pressure 442 mmHg (20 °C)[3]
Acidity (pKa) 10.6
−47.0×10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Nauseating
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS09: Environmental hazard
Danger
H225, H332, H410
P210, P233, P240, P241, P242, P243, P261, P271, P273, P280, P303+P361+P353, P304+P312, P304+P340, P312, P370+P378, P391, P403+P235, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
4
0
Flash point −48 °C; −55 °F; 225 K[3]
Explosive limits
 2.8–18.0%[3]
Lethal dose or concentration (LD, LC):
682 mg/kg (rat, oral)[4]
4410 ppm (rat, 4 hr)
2770 (mouse, 4 hr)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
 C 10 ppm (25 mg/m3)[3]
REL (Recommended)
 C 0.5 ppm (1.3 mg/m3) [15-minute][3]
IDLH
(Immediate danger)
 500 ppm[3]
Related compounds
Related compounds
Butanethiol
Ethanol
thiophenol
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 ?)

Ethanethiol, commonly known as ethyl mercaptan, is an

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.

Preparation

Ethanethiol is prepared by the reaction of

alumina.[6]

Historic methods

Ethanethiol was originally reported by Zeise in 1834.[7] Zeise treated calcium ethyl sulfate with a suspension of barium sulfide saturated with hydrogen sulfide. He is credited with naming the C2H5S- group as mercaptum.

Ethanethiol can also be prepared by a

sodium bisulfide. This conversion was demonstrated as early as 1840 by Henri Victor Regnault.[8]

Odor

Ethanethiol has a strongly disagreeable

humans can detect in minute concentrations. The threshold for human detection is as low as one part in 2.8 billion parts of air (0.36 parts per billion). Its odor resembles that of leeks, onions, durian or cooked cabbage.[9]

Employees of the

turkey vultures would gather at the site of any gas leak. After finding that this was caused by traces of ethanethiol in the gas it was decided to boost the amount of ethanethiol in the gas, to make detection of leaks easier. [10][11]

Uses

Ethanethiol is intentionally added to

asphyxiation
.

In the underground mining industry, ethanethiol or ethyl mercaptan is referred to as "stench gas".[12] The gas is released into mine ventilation systems during an emergency to alert mine workers. In Ontario, mining legislation dictates that "The alarm system in an underground mine shall, consist of the introduction into all workplaces of sufficient quantities of ethyl mercaptan gas or similar gas to be readily detectable by all workers".[13]

Reactions

Main article: Thiol

Ethanethiol is a reagent in organic synthesis. In the presence of sodium hydroxide, it gives the powerful nucleophile EtS−. The salt can be generated quantitatively by reaction with sodium hydride.[14]

Ethanethiol can be oxidized to ethyl

ferric oxide or hydrogen peroxide give the disulfide
, diethyl disulfide:

2 EtSH + H2O2 → EtS-SEt + 2 H2O

Like other thiols, it behaves comparably to hydrogen sulfide. For example, it binds, concomitant with deprotonation to "

cations
, such as Hg2+, Cu+, and Ni2+ to give polymeric thiolato complexes, Hg(SEt)2, CuSEt, and Ni(SEt)2, respectively.

See also

References

  1. ^ Merck Index, 12th edition, hEllon and 3771
  2. ^ "ICSC 0470 - ETHANETHIOL".
  3. ^ a b c d e f g h i NIOSH Pocket Guide to Chemical Hazards. "#0280". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ a b "Ethyl mercaptan". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ISBN 978-1-32-320590-7
    .
  6. ISBN 978-0471801047
    .
  7. ^ Zeise, William Christopher (1834). "Sur le Mercaptan; avec des Observations sur d'autres produits resultant de l'action des sulfovinates ainsi que de l'huile de vin, sur des sulfures metalliques" [On mercaptan; with comments on other products resulting from the action of [salts of] ethyl hydrogen sulfate as well as oil of wine [diethyl sulfate] on metallic sulfides]. Annales de Chimie et de Physique. 2nd series (in French). 56: 87–97.
  8. doi:10.1002/jlac.18400340103. From p. 24: "Das Aethylsulfür war bis jetzt noch nicht dargestellt worden. Man erhält es sehr leicht durch wechselseitige Zersetzung, wenn man Aethylchlorür mit einer weingeistigen Auflösung von einfach Schwefelkalium zusammenbringt." (Ethanethiol still has not been prepared – until now. One obtains it very easily by reciprocal decomposition [i.e., salt metathesis reaction
    ], if one brings together ethyl chloride with a solution, in ethanol, of simple potassium hydrogen sulfide.)
  9. ^ "Ethanethiol price,buy Ethanethiol - chemicalbook". www.chemicalbook.com. Retrieved 16 November 2019.
  10. ISBN 9781444780109
    .
  11. ^ Nicholls, Henry. "The truth about vultures". Retrieved 2016-10-21.
  12. ^ "Stench Gas". Zacon Ltd. Archived from the original on 3 April 2015. Retrieved 20 February 2015.
  13. ^ "Occupational Health and Safety Act: R.R.O. 1990, REGULATION 854 MINES AND MINING PLANTS Sect. 26(6)(a)". Ontario Ministry of Labour. Retrieved 20 February 2015.
  14. ^ Mirrington, R. N.; Feutrill, G. I. (1988). "Orcinol Monomethyl Ether". Organic Syntheses; Collected Volumes, vol. 6, p. 859.

External links

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