- Dimethyl sulfide
-
Dimethyl sulfide 
Methylsulfanylmethane[citation needed]Systematic name(Methylsulfanyl)methane[1]Identifiers CAS number 75-18-3 
PubChem 1068 ChemSpider 1039 UNII QS3J7O7L3U EC number 200-846-2 UN number 1164 KEGG C00580 MeSH dimethyl+sulfide ChEBI CHEBI:17437 ChEMBL CHEMBL15580 RTECS number PV5075000 Beilstein Reference 1696847 3DMet B00138 Jmol-3D images Image 1 - CSC
- InChI=1S/C2H6S/c1-3-2/h1-2H3
Key: QMMFVYPAHWMCMS-UHFFFAOYSA-N
Properties Molecular formula C2H6S Molar mass 62.13 g mol−1 Exact mass 62.019020882 g mol-1 Appearance Colourless liquid Odor Cabbage, sulfurous Density 846 mg cm-3 Melting point -98 °C, 175 K, -145 °F
Boiling point 35-41 °C, 308-314 K, 95-106 °F
log P 0.977 Vapor pressure 53.7 kPa (at 20 °C) Refractive index (nD) 1.435 Thermochemistry Std enthalpy of
formation ΔfHo298-66.9--63.9 kJ mol-1 Std enthalpy of
combustion ΔcHo298-2.1818--2.1812 MJ mol-1 Hazards MSDS osha.gov GHS pictograms 
GHS signal word DANGER GHS hazard statements H225, H315, H318, H335 GHS precautionary statements P210, P261, P280, P305+351+338 EU classification 
F 
XnR-phrases R11, R22, R37/38, R41 S-phrases S7, S9, S16, S26, S29, S33, S36/39 Flash point -36 °C Autoignition
temperature206 °C Explosive limits 19.7% 
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)Infobox references Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula (CH3)2S. Dimethyl sulfide is a water-insoluble flammable liquid that boils at 37 °C (99 °F) and has a characteristic disagreeable odor. It is a component of the smell produced from cooking of certain vegetables, notably maize, cabbage, beetroot and seafoods. It is also an indication of bacterial infection in malt production and brewing. It is a breakdown product of dimethylsulfoniopropionate (DMSP), and is also produced by the bacterial metabolism of methanethiol.
Contents
Natural occurrence
DMS originates primarily from DMSP, a major secondary metabolite in some marine algae.[citation needed] DMS is the most abundant biological sulfur compound emitted to the atmosphere.[2] Emission occurs over the oceans 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.[3]
DMS is oxidized in the marine atmosphere to various sulfur-containing compounds, such as sulfur dioxide, dimethyl sulfoxide (DMSO), dimethyl sulfone, methanesulfonic acid and sulfuric acid.[4] 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.[5] The CLAW hypothesis suggests that in this manner DMS may play a role in planetary homeostasis.[6]
Smell
Dimethyl sulfide has a characteristic cabbage-like smell that becomes highly disagreeable 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,[7] asparagus,[8] 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".[9] It would be more accurate to say that DMS is a component of the "smell of the sea," another being pheromones of algae called dictyopterenes.[10]
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 and carbon monoxide. In addition it is used to control dusting in steel mills. It is also used in a range of organic syntheses, including as a reducing agent in ozonolysis reactions. 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.
Other uses
Dimethyl sulfide finds a niche use as a displaceable ligand in chloro(dimethyl sulfide)gold(I) and other coordination compounds.
Safety
Dimethyl sulfide is highly flammable and irritant to eyes and skin. It is harmful if swallowed and has an unpleasant odor at even extremely low concentrations. Its ignition temperature is 205 °C.
See also
- Coccolithophore, a marine unicellular planktonic photosynthetic algae, producer of DMS
- Dimethylsulfoniopropionate, a parent molecule of DMS and methanethiol in the oceans
- Dimethyl selenide, a selenium analogue of DMS produced by bacteria and phytoplankton
- Dimethyl telluride, a tellurium analogue of DMS
- Emiliania huxleyi, a coccolithophorid producing DMS
- Swern oxidation
- Gaia hypothesis
References
- ^ "dimethyl sulfide (CHEBI:17437)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 17 October 2009. Main. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=17437. Retrieved 19 October 2011.
- ^ 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. (1999). "Inventorying emissions from nature in Europe". Journal of Geophysical Research 104 (D7): 8113–8152. Bibcode 1999JGR...104.8113S. doi:10.1029/98JD02747.
- ^ Glindemann, D., Novak, J., Witherspoon, J. (2006). "Dimethyl Sulfoxide (DMSO) Waste Residues and Municipal Waste Water Odor by Dimethyl Sulfide (DMS): the North-East WPCP Plant of Philadelphia.". Environmental Science and Technology 40 (1): 202–207. doi:10.1021/es051312a. PMID 16433352.
- ^ Lucas, DD; Prinn, RG (2005). "Parametric sensitivity and uncertainty analysis of dimethylsulfide oxidation in the clear-sky remote marine boundary layer". Atmospheric Chemistry and Physics 5 (6): 1505–1525. doi:10.5194/acp-5-1505-2005.
- ^ Malin, G; Turner, SM; Liss, PS (1992). "Sulfur: The plankton/climate connection". Journal of Phycology 28 (5): 590–597. doi:10.1111/j.0022-3646.1992.00590.x.
- ^ Charlson, R. J., Lovelock, J. E., Andreae, M. O. and Warren, S. G. (1987). "Oceanic phytoplankton, atmospheric sulphur, cloud albedo and climate". Nature 326 (6114): 655–661. Bibcode 1987Natur.326..655C. doi:10.1038/326655a0. http://www.nature.com/nature/journal/v326/n6114/abs/326655a0.html.
- ^ Blackwell Synergy - J Food Science, Volume 42 Issue 6 Page 1592-1593, November 1977 (Article Abstract)
- ^ http://www.springerlink.com.libproxy.tkk.fi/content/djbrepd4mjpjqgwn/
- ^ University of East Anglia press release, Cloning the smell of the seaside, February 2, 2007
- ^ Toshiyuki Itoh, Hitomi Inoue and Sachie Emoto (2000). "Synthesis of Dictyopterene A: Optically Active Tributylstannylcyclopropane as a Chiral Synthon". Bulletin of the Chemical Society of Japan 73 (2): 409–416. ISSN 1348-0634. http://www.jstage.jst.go.jp/article/bcsj/73/2/73_409/_article/-char/en.
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