Dimethyl sulfide 2249388 222298585 2008-06-28T16:09:07Z 80.82.38.5 {{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]] [[de:Dimethylsulfid]] [[it:Solfuro dimetile]] [[hu:Dimetil-szulfid]] [[ml:ഡൈമീഥൈല്‍ സള്‍ഫൈഡ്]] [[ja:ジメチルスルフィド]] [[fi:Dimetyylisulfidi]] [[uk:Діметилсульфід]] [[ru:Диметилсульфид]]