Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Dimethyl disulfide: Difference between pages

| Watchedfields = changed

| verifiedrevid = 470456193

| ImageFileL2 = Dimethyl-disulfide-from-xtal-Mercury-3D-bs.png

| ImageFileR2 = Dimethyl-disulfide-from-xtal-Mercury-3D-sf.png

| PIN = (Methyldisulfanyl)methane<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 708 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>

| OtherNames = Dimethyl disulfide<ref name=iupac2013 /><br />Methyl disulfide<br />Methyldisulfide<br />Dimethyldisulfide<br />Methyldithiomethane<br />2,3-Dithiabutane

|Section1={{Chembox Identifiers

| Abbreviations = DMDS

| CASNo = 624-92-0

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 3P8D642K5E

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| SMILES = S(SC)C

| InChI = InChI=1S/C2H6S2/c1-3-4-2/h1-2H3

|Section2={{Chembox Properties

| Formula = {{chem2|CH3SSCH3}}

| C=2 | H=6 | S=2

| Appearance = Colorless liquid

| Density = 1.06 g/cm³<ref name=GESTIS>{{GESTIS|ZVG=10510}}</ref>

| MeltingPtC = -85

| MeltingPt_ref = <ref name=GESTIS/>

| BoilingPtC = 110

| BoilingPt_ref = <ref name=GESTIS/>

| VaporPressure = 3.8 kPa (at 25 °C) [http://www.arkema-inc.com/tds/885.pdf Arkema data sheet]

| Solubility = 2.5 g/L (20 °C)<ref name=GESTIS/>

|Section3={{Chembox Hazards

| MainHazards =

| FlashPtC = 15

| FlashPt_ref = <ref name=GESTIS/>

| AutoignitionPtC = 370

| AutoignitionPt_ref = <ref name=GESTIS/>

| LD50 = 190 mg/kg (oral, rat)<ref>[http://www.epa.gov/pesticides/chem_search/reg_actions/pending/fs_PC-029088_09-Jul-10.pdf], EPA DMDS Fact Sheet</ref>

'''Dimethyl disulfide''' ('''DMDS''') is an [[organic compound|organic]] [[chemical compound]] with the molecular formula {{chem2|CH3SSCH3}}. It is a flammable liquid with an unpleasant, [[garlic]]-like odor. The compound is colorless although impure samples often appear yellowish.

==Occurrence and synthesis==

Dimethyl disulfide is widespread in nature. It is emitted by bacteria, fungi, plants, and animals.

Along with [[dimethyl sulfide]] and [[dimethyl trisulfide]] it has been confirmed as volatile compounds given off by the fly-attracting plant known as [[dead-horse arum]] (''[[Helicodiceros muscivorus]]''). These flies are attracted to the [[odor]] 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>

DMDS can be produced by the oxidation of [[methanethiol]], e.g. with [[iodine]]:

:{{chem2|2 CH3SH + I2 → CH3SSCH3 + 2 HI}}

==Chemical reactions==

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 [[methanesulfonyl chloride]] ({{chem2|CH3SO2Cl}}) as well as oxidation with [[hydrogen peroxide]] or [[peracetic acid]] giving the [[thiosulfinate]] 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>

==Uses==

DMDS is used as a food additive in onion, garlic, cheese, meats, soups, savory flavors, and fruit flavors.<ref>[https://www.osha.gov/dts/chemicalsampling/data/CH_236060.html], OSHA</ref> Industrially, DMDS is used in oil refineries as a sulfiding agent.<ref>[http://www.arkema-inc.com/index.cfm?pag=118 Dimethyl Disulfide (DMDS)] {{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 [[methyl bromide]], which is being phased out. However, it is less effective than the former. This pesticide is marketed as "Paladin" by [[Arkema]].<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>

===Industrial use===

DMDS is used to prepare catalysts for [[hydrodesulfurization]], 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 [[dimethyl sulfide]] (DMS) or [http://www.reactor-resources.com/sulfur-chemistry/tertiary-butyl-polysulfide-(tbps).html di-tertiary-butyl polysulfide (TBPS).]<ref>[http://www.reactor-resources.com/sulfur-chemistry/dimethyl-disulfide-dmds.html Dimethyl Disulfide (DMDS)]</ref> Once injected to a hydrotreater or hydrocracker, It decomposes to form H₂S. The H₂S 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>

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.

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. [[Thiophene]] and DMDS are blended with combustible hydrocarbon fuel gas to impart a gassy odor to the fuel gas.

==References==

{{reflist|refs=10. Dimethyl Disulfide (DMDS), Reactor Resources LLC}}

{{Authority control}}

[[Category:Organic disulfides]]

[[Category:Foul-smelling chemicals]]

[[Category:Methyl compounds]]