| Revision as of 16:21, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 469645079 of page Dimethyl_disulfide for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 08:50, 23 October 2024 edit Citation bot (talk | contribs)Bots5,422,622 edits Added bibcode. Removed parameters. | Use this bot. Report bugs. | Suggested by Dominic3203 | Category:Foul-smelling chemicals | #UCB_Category 6/128 |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 455343010 |
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| verifiedrevid = 470456193 |
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| ImageFileL1 = Dimethyl disulfide expanded.svg |
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| ImageFileL1 = Dimethyl disulfide expanded.svg |
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| ImageSizeL1 = 100px |
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| ImageFileR1 = Dimethyl disulfide skeletal.svg |
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| ImageFileR1 = Dimethyl disulfide skeletal.svg |
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| ImageFileL2 = Dimethyl-disulfide-from-xtal-Mercury-3D-bs.png |
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| ImageSizeR1 = 100px |
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| ImageFileL2 = Dimethyl-disulfide-3D-balls.png |
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| ImageFileR2 = Dimethyl-disulfide-from-xtal-Mercury-3D-sf.png |
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| PIN = (Methyldisulfanyl)methane<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 708 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref> |
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| ImageSizeL2 = 100px |
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| OtherNames = Dimethyl disulfide<ref name=iupac2013 /><br />Methyl disulfide<br />Methyldisulfide<br />Dimethyldisulfide<br />Methyldithiomethane<br />2,3-Dithiabutane |
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| ImageFileR2 = Dimethyl disulfide spacefill.png |
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|Section1={{Chembox Identifiers |
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| Abbreviations = DMDS |
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| IUPACName = (Methyldisulfanyl)methane |
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| CASNo = 624-92-0 |
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| OtherNames = Dimethyl disulphide; Methyl disulfide; Methyldisulfide; Dimethyldisulfide; Methyldithiomethane; 2,3-Dithiabutane |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Section1 = {{Chembox Identifiers |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| Abbreviations = DMDS |
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| CASNo = 624-92-0 |
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| UNII = 3P8D642K5E |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 4608 |
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| ChEBI = 4608 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WQOXQRCZOLPYPM-UHFFFAOYSA-N |
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| StdInChIKey = WQOXQRCZOLPYPM-UHFFFAOYSA-N |
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| PubChem = 12232 |
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| PubChem = 12232 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 11731 |
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| ChemSpiderID = 11731 |
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| SMILES = S(SC)C |
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| SMILES = S(SC)C |
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| InChI = InChI=1S/C2H6S2/c1-3-4-2/h1-2H3 |
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| InChI = InChI=1S/C2H6S2/c1-3-4-2/h1-2H3 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = {{chem2|CH3SSCH3}} |
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| C=2|H=6|S=2 |
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| C=2 | H=6 | S=2 |
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| Appearance = Colorless to yellowish liquid<ref name=GESTIS>{{GESTIS|ZVG=10510}}</ref> |
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| Appearance = Colorless liquid |
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| Density = 1.06 g/cm<sup>3</sup><ref name=GESTIS/> |
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| Density = 1.06 g/cm<sup>3</sup><ref name=GESTIS>{{GESTIS|ZVG=10510}}</ref> |
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| MeltingPtC = -85 |
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| MeltingPtC = -85 |
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| Melting_notes = <ref name=GESTIS/> |
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| MeltingPt_ref = <ref name=GESTIS/> |
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| BoilingPtC = 110 |
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| BoilingPtC = 110 |
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| Boiling_notes = <ref name=GESTIS/> |
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| Solubility = 2.5 g/L (20 °C)<ref name=GESTIS/> |
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| BoilingPt_ref = <ref name=GESTIS/> |
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| VaporPressure = 3.8 kPa (at 25 °C) |
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| Solubility = 2.5 g/L (20 °C)<ref name=GESTIS/> |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| FlashPtC = 15 |
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| FlashPt = {{convert|15|C|F}}<ref name=GESTIS/> |
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| Autoignition = {{convert|370|C|F}}<ref name=GESTIS/> |
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| FlashPt_ref = <ref name=GESTIS/> |
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| AutoignitionPtC = 370 |
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| LD50 = 190 mg/kg (oral, rat)<ref name=thegoodscentscompany>, Good Scents Company</ref> |
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| AutoignitionPt_ref = <ref name=GESTIS/> |
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| LD50 = 190 mg/kg (oral, rat)<ref>, EPA DMDS Fact Sheet</ref> |
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'''Dimethyl disulfide''' ('''DMDS''') is an ] ] with the molecular formula {{chem2|CH3SSCH3}}. It is a flammable liquid with an unpleasant, ]-like odor. The compound is colorless although impure samples often appear yellowish. |
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==Occurrence and synthesis== |
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Dimethyl disulfide is widespread in nature. It is emitted by bacteria, fungi, plants, and animals. |
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Along with ] and ] it has been confirmed as volatile compounds given off by the fly-attracting plant known as ] ('']''). These flies are attracted to the ] resembling that of fetid meat, and thus help pollinate this plant.<ref>{{cite journal |journal=Nature |volume=420 |year=2002 |pages=625–626 |author1=Marcus C. Stensmyr |author2=Isabella Urru |author3=Ignazio Collu |author4=Malin Celander |author5=Bill S. Hansson |author6=Anna-Maria Angioy | title=Rotting smell of dead-horse arum florets |doi=10.1038/420625a |pmid=12478279 |issue=6916|bibcode=2002Natur.420..625S |s2cid=1001475 }}</ref> |
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DMDS can be produced by the oxidation of ], e.g. with ]: |
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:{{chem2|2 CH3SH + I2 → CH3SSCH3 + 2 HI}} |
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==Chemical reactions== |
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Important reactions include chlorination giving methanesulfenyl chloride ({{chem2|CH3SCl}}), methanesulfinyl chloride ({{chem2|CH3S(O)Cl}}),<ref>Irwin B. Douglass and Richard V. Norton "Methanesulfinyl Chloride" ''Organic Syntheses'', Coll. Vol. 5, p.709-712 (1973).</ref> and ] ({{chem2|CH3SO2Cl}}) as well as oxidation with ] or ] giving the ] methyl methanethiosulfinate ({{chem2|CH3S(O)SCH3}}).<ref>{{cite journal | doi = 10.1021/ja00819a033 | title = Chemistry of Alkyl Thiosulfinate Esters. VI. Preparation and Spectral Studies | year = 1974 | last1 = Block | first1 = Eric | last2 = O'Connor | first2 = John | journal = Journal of the American Chemical Society | volume = 96 | issue = 12 | pages = 3921}}</ref> |
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==Uses== |
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DMDS is used as a food additive in onion, garlic, cheese, meats, soups, savory flavors, and fruit flavors.<ref>, OSHA</ref> Industrially, DMDS is used in oil refineries as a sulfiding agent.<ref> {{Webarchive|url=https://web.archive.org/web/20110929015920/http://www.arkema-inc.com/index.cfm?pag=118 |date=2011-09-29 }}, Arkema, Inc.</ref> It is also an effective soil fumigant in agriculture, registered in many states in the U.S. as well as globally. In this capacity, It is an important alternative in replacing ], which is being phased out. However, it is less effective than the former. This pesticide is marketed as "Paladin" by ].<ref>{{Cite web |title=DMDS for agricultural soil fumigation |url=http://www.arkema.com/en/products/product-finder/range-viewer/DMDS-for-agricultural-soil-fumigation/ |publisher=Arkema |accessdate=2013-09-06}}</ref><ref>{{citation| publisher = New York State Department of Environmental Conservation | url = http://pmep.cce.cornell.edu/profiles/fumigant/dimethyl_disulfide/dimethyl_disulfide_reg_0312.pdf | title = Registration of Paladin and Paladin EC containing the new active ingredient dimethyl disulfide | date = March 9, 2012}}</ref> |
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===Industrial use=== |
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DMDS is used to prepare catalysts for ], because of its high sulfur content and low decomposition temperature. Refineries utilize it instead of other sulfur spiking agents for catalyst sulfiding because it has more sulfur per pound than ] (DMS) or <ref></ref> Once injected to a hydrotreater or hydrocracker, It decomposes to form H<sub>2</sub>S. The H<sub>2</sub>S reacts with the metal oxides on the catalyst, converting them to the active metal sulfide form.<ref>{{cite web |url=http://www.reactor-resources.com/sulfiding-services/sulfiding-101.html|title= Reactor Resources}}</ref> |
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DMDS also works as an effective product for operators in the petrochemicals industry who must protect their steam-cracking coils against the formation of coke and carbon monoxide. |
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DMDS is utilized in the preparation of 4-(methylthio)phenol which is used in the production of various pesticides. DMDS and chlorine are reacted with borontrifluoride phenoxide to produce 4-(methylthio)phenol. ] and DMDS are blended with combustible hydrocarbon fuel gas to impart a gassy odor to the fuel gas. |
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==References== |
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{{reflist|refs=10. Dimethyl Disulfide (DMDS), Reactor Resources LLC}} |
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{{Authority control}} |
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] |
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] |
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] |