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Contents
Structure and reactions Names
Occurrence Preferred IUPAC name
Preparation Methanethiol
Uses Other names
Safety Methyl mercaptan
References Mercaptomethane
External links Methiol
Thiomethyl alcohol
Methylthiol
Structure and reactions Identifiers
sulfate (~0.3 nM vs. 28 mM). Bacteria in environments both with and S-phrases S16, S25, S33S60, S61
without oxygen can also convert methanethiol todimethyl sulfide (DMS), (outdated)
although most DMS in surface seawater is produced by a separate NFPA 704
pathway. Both DMS and methanethiol can be used by certain microbes as 4
substrates for methanogenesis in some anaerobic soils. 4 1
Methanethiol is a byproduct of the metabolism of asparagus.[4] The
ability to produce methanethiol in urine after eating asparagus was once Flash point −18 °C; 0 °F; 255 K [1]
thought to be a genetic trait. More recent research suggests that the Explosive limits 3.9%-21.8%[1]
peculiar odor is in fact produced by all humans after consuming Lethal dose or concentration (LD, LC):
asparagus, while the ability to detect it (methanethiol being one of many
LD50 (median 60.67 mg/kg (mammal)[2]
components in "asparagus pee") is in fact the genetic trait.[5] The dose)
chemical components responsible for the change in the odor of urine
[6]
LC50 (median 3.3 ppm (mouse, 2 hr)
show as soon as 15 minutes after eating asparagus. concentration) 675 ppm (rat, 4 hr)[2]
US health exposure limits (NIOSH):
Preparation PEL C 10 ppm (20 mg/m3)[1]
Methanethiol is prepared commercially by the reaction of methanol with (Permissible)
hydrogen sulfide gas over an acidic solid catalyst, such asalumina:[7] REL C 0.5 ppm (1 mg/m3) [15-
(Recommended) minute][1]
CH3OH + H2S → CH3SH + H2O
IDLH 150 ppm[1]
(Immediate
Although impractical, it can be prepared by the reaction of methyl iodide danger)
with thiourea.[8]
Related compounds
Related Ethanethiol
Uses compounds
Hydrogen sulfide
Methanethiol is mainly used to produce methionine, which is used as a
dietary component in poultry and animal feed.[7] Methanethiol is also Except where otherwise noted, data are given
for materials in their standard state (at 25 °C
used in the plastic industry as a moderator for free-radical
[77 °F], 100 kPa).
polymerizations[7] and as a precursor in the manufacture ofpesticides.
verify (what is ?)
Mercaptan is also used in the natural gas industry as an odorant, due to its Infobox references
ideal compatibility with methane. Its characteristic "rotten eggs" smell is
widely known by natural gas customers as an indicator of a possible gas
leak, even a very minute one.[9]
Safety
The safety data sheet (SDS) lists methanethiol as a colorless, flammable gas with an
extremely strong and repulsive smell. At very high concentrations it is highly toxic
and affects the central nervous system. Its penetrating odor provides warning at
dangerous concentrations. An odor threshold of 1 ppb has been reported.[10] The
United States OSHA Ceiling Limit is listed as 10 ppm.
A severe methyl mercaptan leak killed four employees and injured another in a
DuPont facility in La Porte, Texas, near Houston, on 15 November 2014.[11]
References
1. "NIOSH Pocket Guide to Chemical Hazards #0425"(https://www.cdc.go
v/niosh/npg/npgd0425.html). National Institute for Occupational Safety
and Health (NIOSH).
2. "Methyl mercaptan" (https://www.cdc.gov/niosh/idlh/74931.html).
Immediately Dangerous to Life and Health Concentrations (IDLH) .
National Institute for Occupational Safety and Health(NIOSH).
3. Sixta, H.; Potthast, A.; Krotschek, A. W., Chemical Pulping Processes.
In Handbook of Pulp, Sixta, H., Ed. Wiley-VCH V erlag GmbH & Co.: Cylinder of methanethiol gas
Weinheim, 2006; Vol. 1, p 169 (109-510).
4. Richer, Decker, Belin, Imbs, Montastruc, Giudicelli:"Odorous urine in
man after asparagus" (http://www.pubmedcentral.nih.gov/articlerender.fc
gi?artid=1379934), British Journal of Clinical Pharmacology, May 1989
5. Lison M, Blondheim SH, Melmed RN (1980)."A polymorphism of the
ability to smell urinary metabolites of asparagus"(https://www.ncbi.nlm.n
ih.gov/pmc/articles/PMC1715705). Br Med J. 281 (6256): 1676–8.
doi:10.1136/bmj.281.6256.1676(https://doi.org/10.1136%2Fbmj.281.62
56.1676). PMC 1715705 (https://www.ncbi.nlm.nih.gov/pmc/articles/PM
C1715705) . PMID 7448566 (https://www.ncbi.nlm.nih.gov/pubmed/744
8566).
6. Skinny On: Discovery Channel(http://www.discovery.com/area/skinnyo
n/skinnyon970115/skinny1.html)Archived (https://web.archive.org/web/2
0080229081018/http://www.discovery.com/area/skinnyon/skinnyon9701
15/skinny1.html) 2008-02-29 at the Wayback Machine.
7. Norell, John; Louthan, Rector P. (1988). "Thiols". Kirk-Othmer Concise
Encylclopedia of Chemical Technology (3rd ed.). New York: John Wiley
& Sons, Inc. pp. 946–963.ISBN 978-0471801047.
8. Reid, E. Emmet (1958).Organic Chemistry of Bivalent Sulfur. 1. New
York: Chemical Publishing Company, Inc. pp. 32–33, 38.
9. SafeGase: About Natural Gas:(http://www.safegas.org/about/about.htm
l)
10. Devos, M; F. Patte; J. Rouault; P. Lafort; L. J. Van Gemert (1990).
Standardized Human Olfactory Thresholds. Oxford: IRL Press. p. 101.
ISBN 0199631468.
11. HazMat Management Magazine article:(http://www.hazmatmag.com/ha
zmat/four-dupont-workers-suffocated-methyl-mercaptan-leak-texas/1003
272774/)
External links
NLM Hazardous Substances Databank – Methyl mercaptan
CDC - NIOSH Pocket Guide to Chemical Hazards
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