Dimethyl sulfide
2249388
222298585
2008-06-28T16:09:07Z
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{{Chembox new
| Name = Dimethyl sulfide
| ImageFileL1 = Dimethyl sulfide structure.svg
| ImageSizeL1 = 120px
| ImageNameL1 = Dimethyl sulfide
| ImageFileR1 = Dimethyl-sulfide-3D-vdW.png
| ImageSizeR1 = 150px
| ImageNameR1 = DMS
| IUPACName = Dimethyl sulfide
| Section1 = {{Chembox Identifiers
| CASNo = 75-18-3
| SMILES = CSC
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>2</sub>H<sub>6</sub>S
| MolarMass = 62.13 g/mol
| Density = 0.840 g/cm³
| MeltingPt = -98 °C
| BoilingPt = 37 °C
}}
| Section7 = {{Chembox Hazards
| ExternalMSDS = [http://www.osha.gov/dts/chemicalsampling/data/CH_236505.html OSHA MSDS]
}}
}}
'''Dimethyl sulfide''' (DMS) or methylthiomethane is an [[Organosulfur compounds|organosulfur]] compound with the formula (CH<sub>3</sub>)<sub>2</sub>S. Dimethyl sulfide is a water-insoluble flammable liquid that boils at 37°C and has a characteristic disagreeable odor. It is a component of the smell produced from cooking of certain vegetables, notably corn, cabbage, [[beetroot]] and seafoods. It is also an indication of [[bacteria]]l infection in [[malt]] production and [[brewing]]. It is a breakdown product of [[dimethylsulfoniopropionate]] (DMSP), and is also produced by the bacterial metabolism of [[methanethiol]].
==Natural sources and link with climate==
DMS is the most abundant biological sulfur compound emitted to the [[Earth's atmosphere|atmosphere]].<ref>{{cite journal
| author = Simpson, David; Winiwarter, Wilfried; Börjesson, Gunnar; Cinderby, Steve; Ferreiro, Antonio; Guenther, Alex; Hewitt, C. Nicholas; Janson, Robert; Khalil, M. Aslam K.; Owen, Susan; Pierce, Tom E.; Puxbaum, Hans; Shearer, Martha; Skiba, Ute; Steinbrecher, Rainer; Tarrasón, Leonor; Öquist, Mats G.
| title = Inventorying emissions from nature in Europe
| journal = [[Journal of Geophysical Research.]]
| year = 1999
| volume = 104
| issue = D7
| pages = 8113–8152
| doi = 10.1029/98JD02747
}}</ref> Emission occurs over the [[ocean]]s by [[phytoplankton]]. DMS is also produced naturally by bacterial transformation of [[dimethyl sulfoxide]] (DMSO) waste that is disposed of into sewers, where it can cause environmental odor problems.<ref>{{cite journal
|author= Glindemann, D., Novak, J., Witherspoon, J.
|title= Dimethyl Sulfoxide (DMSO) Waste Residues and Municipal Waste Water Odor by Dimethyl Sulfide (DMS): the North-East WPCP Plant of Philadelphia.
|journal= Environmental Science and Technology
|year= 2006
| volume = 40
| issue = 1
|pages=202–207
|doi=10.1021/es051312a S0013-936X(05)01312-X }}
</ref>.
DMS is oxidized in the marine atmosphere to various sulfur-containing compounds, such as [[sulfur dioxide]], [[dimethyl sulfoxide]] (DMSO), dimethyl sulfone, [[sulfonic acid|methane sulfonic acid]] and [[sulfuric acid]].
<ref>{{cite journal
| author = Lucas, DD; Prinn, RG
| title = Parametric sensitivity and uncertainty analysis of dimethylsulfide oxidation in the clear-sky remote marine boundary layer.
| journal = [[Atmospheric Chemistry and Physics]]
| year = 2005
| volume = 5
| pages = 1505–1525
}}</ref>
Among these compounds, sulfuric acid has the potential to create new [[aerosols]] which act as [[cloud condensation nuclei]]. Through this interaction with [[cloud]] formation, the massive production of atmospheric DMS over the oceans may have a significant impact on the Earth's [[climate]].<ref>{{cite journal
| author = Malin, G; Turner, SM; Liss, PS
| title = Sulfur: The plankton/climate connection.
| journal = [[Journal of Phycology]]
| year = 1992
| volume = 28
| issue = 5
| pages = 590–597
| doi =
}}</ref>
Recent research suggests that marine bacteria are reducing the amount of this important climate cooling gas given off from our seas. {{Fact|date=April 2007}}
== Smell ==
Dimethyl sulfide has a characteristic cabbage-like smell that becomes highly disagreeble at higher concentrations. DMS has a low olfactory threshold that varies from 0.02 to 0.1 ppm between different persons. However, it is also available as a food additive to impart a savory flavor; in such use, its concentration is low. Beetroot,<ref>[http://www.blackwell-synergy.com/doi/abs/10.1111/j.1365-2621.1977.tb08434.x Blackwell Synergy - J Food Science, Volume 42 Issue 6 Page 1592-1593, November 1977 (Article Abstract)<!-- Bot generated title -->]</ref> asparagus,<ref>http://www.springerlink.com.libproxy.tkk.fi/content/djbrepd4mjpjqgwn/</ref> cabbage, corn and seafoods produce dimethyl sulfide when cooked.
Marine phytoplankton also produces dimethyl sulfide. Andrew Johnston, of the [[University of East Anglia]], has characterized DMS as being the "smell of the sea".<ref>University of East Anglia press release, [http://comm.uea.ac.uk/press/release.asp?id=720 Cloning the smell of the seaside], February 2, 2007</ref> It would be more accurate to say that DMS is a component of the "smell of the sea," another being [[pheromone]]s of algae called [[dictyopterene]]s.
Dimethyl sulfide is also an odorant emitted by [[kraft pulping]] mills, and a byproduct of [[Swern oxidation]].
==Industrial uses==
In industry it is used in [[petroleum]] refining and in [[petrochemical]] production processes to control the formation of [[coke (fuel)|coke]] and [[carbon monoxide]]. In addition it is used to control dusting in steel mills. It is also used in a range of organic [[chemical synthesis|syntheses]], also being a side product of [[Swern oxidation]]. It also has a use as a food flavoring component. It can also be oxidized by natural or artificial means to [[dimethyl sulfoxide]], (DMSO), which has several important solvent properties.
The largest single commercial producer of DMS in the world is Gaylord Chemical Corporation, which is a significant economic component of the paper industry of [[Bogalusa, Louisiana]].
==Safety==
Dimethyl sulfide is [[flammable]] and an [[irritant]]. Dimethyl sulfide has an unpleasant odor at even extremely low concentrations.
==See also==
* [[CLAW hypothesis]]
* [[Dimethyl telluride]]
* [[Swern oxidation]]
==References==
{{reflist}}
==External links==
*[http://www.homebrewzone.com/dimethyl-sulfide.htm Brewing]
*[http://saga.pmel.noaa.gov/dms/DMSweb_program_descript.html NOAA DMS flux]
*[http://saga.pmel.noaa.gov/underwaydms/why.html Dimethylsulfide (DMS) in the Bering Sea and Adjacent Waters: In-situ and Satellite Observations]
*[http://saga.pmel.noaa.gov/review/dms_climate.html DMS and Climate]
*[http://www.chemicalland21.com/arokorhi/industrialchem/solalc/DIMETHYL%20SULFIDE.htm Industrial chemicals]
[[Category:Climate]]
[[Category:Thioethers]]
[[Category:Sulfides]]
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