Carbon disulfide 241809 220379770 2008-06-19T16:04:07Z DOI bot 6652755 Citation maintenance. You can [[WP:DOI|use this bot]] yourself! Please [[User:DOI_bot/bugs|report any bugs]]. {{redirect|CS2|the software package by [[Adobe Systems]]|Adobe Creative Suite}} {{Chembox new | Name = '''Carbon disulfide''' | ImageFile = Carbon-disulfide-2D-dimensions.png | ImageSize = 150px | ImageFile1 = Carbon-disulfide-3D-vdW.png | ImageSize1 = 150px | ImageName = Carbon disulfide | IUPACName = Carbon disulfide | OtherNames = Dithiocarbonic anhydride | Section1 = {{Chembox Identifiers | SMILES = CS(S) | CASNo = 75-15-0 }} | Section2 = {{Chembox Properties | Formula = CS<sub>2 | MolarMass = 76.1 g/mol | Appearance = colorless liquid<br />impure: light-yellow | Density = 1.26 g/cm³ | MeltingPt = -111.6 °C (161.6 K) | BoilingPt = 46 °C (319 K) | Solvent = other solvents | SolubleOther = 0.2 g/100 ml of water (20 °C) }} | Section7 = {{Chembox Hazards | FlashPt = -30 °C | Autoignition = 90 °C | RPhrases = {{R11}}, {{R23}}, {{R24}}, {{R25}}, {{R48}} | SPhrases = {{S16}}, {{S33}}, {{S44}}, {{S53}} | Hazards = Highly flammable<br />CNS toxicant | NFPA-H = 3 | NFPA-F = 4 | NFPA-R = 0}} }} '''Carbon disulfide''' is a colorless, [[volatile]] [[liquid]] with the [[chemical formula|formula]] CS<sub>2</sub>. The compound is used frequently as a building block in [[organic chemistry]] as well as an industrial and chemical non-polar [[solvent]]. It has an "[[diethyl ether|ether]]-like" odor, but commercial samples are typically contaminated with foul-smelling impurities.<ref name=Holleman>Holleman, A. F.; Wiberg, E. "Inorganic Chemistry" Academic Press: San Diego, 2001. ISBN 0-12-352651-5.</ref> ==Occurrence and manufacture== Small amounts of carbon disulfide are released by [[volcano|volcanic]] eruptions and [[marsh]]es. CS<sub>2</sub> once was manufactured by combining [[carbon]] (or [[Coke_%28fuel%29|coke]]) and [[sulfur]] at high temperatures. A lower temperature reaction, requiring only 600 °C utilizes [[natural gas]] as the carbon source in the presence of [[silica gel]] or [[alumina]] [[catalyst]]s:<ref name=Holleman/> :CH<sub>4</sub> + 1/2 S<sub>8</sub> → CS<sub>2</sub> + 2 H<sub>2</sub>S The reaction is analogous to the combustion of methane. Although it is isoelectronic to carbon dioxide, CS<sub>2</sub> is highly flammable: :CS<sub>2</sub> + 3 O<sub>2</sub> → CO<sub>2</sub> + 2 [[Sulfur dioxide|SO<sub>2</sub>]] ==Reactions== Compared to CO<sub>2</sub>, CS<sub>2</sub> is more reactive toward [[nucleophile]]s and more easily reduced. These differences in reactivity can be attributed to the weaker π donor-ability of the sulfido centers, which renders the carbon more electrophilic. It is widely used in the synthesis of organosulfur compounds such as Metham sodium, a soil fumigant. ===Addition of nucleophiles=== Nucleophiles such as amines afford [[Sodium diethyldithiocarbamate|dithiocarbamate]]s: :2R<sub>2</sub>NH + CS<sub>2</sub> → [R<sub>2</sub>NH<sub>2</sub><sup>+</sup>][R<sub>2</sub>NCS<sub>2</sub><sup>-</sup>] Xanthates form similarly from [[alkoxide]]s: :RONa + CS<sub>2</sub> → [Na<sup>+</sup>][ROCS<sub>2</sub><sup>-</sup>] This reaction is the basis of the manufacture of regenerated [[cellulose]], the main ingredient of [[viscose]], [[rayon]] and [[cellophane]]. Both xanthates and the related thioxanthates (derived from treatment of CS<sub>2</sub> with sodium [[thiolate]]s) are used as flotation agents in mineral processing. Sodium sulfide affords trithiocarbonate: :Na<sub>2</sub>S + CS<sub>2</sub> → [Na<sup>+</sup>]<sub>2</sub>[CS<sub>3</sub><sup>2-</sup>] ===Reduction=== Sodium reduces CS<sub>2</sub> to give the heterocycle "dmit<sup>2-</sup>":<ref>Girolami, G. S.; Rauchfuss, T. B. and Angelici, R. J., Synthesis and Technique in Inorganic Chemistry, University Science Books: Mill Valley, CA, 1999.ISBN: 0935702482</ref> ::3 CS<sub>2</sub> + 4 Na → Na<sub>2</sub>C<sub>3</sub>S<sub>5</sub> + Na<sub>2</sub>S Direct electrochemical reduction affords the tetrathiooxalate anion:<ref>Jeroschewski, P. "Electrochemical Preparation of Tetraalkylammonium Salts of Tetrathiooxalic Acid" Zeitschrift für Chemie (1981), volume 21, 412.</ref> ::2 CS<sub>2</sub> + 2e<sup>-</sup> → C<sub>2</sub>S<sub>4</sub><sup>2-</sup> ===Chlorination=== Chlorination of CS<sub>2</sub> is the principal route to [[carbon tetrachloride]]:<ref name=Holleman/> : CS<sub>2</sub> + 3 [[chlorine|Cl<sub>2</sub>]] → CCl<sub>4</sub> + [[sulfur monochloride|S<sub>2</sub>Cl<sub>2</sub>]] This conversion proceeds via the intermediacy of [[thiophosgene]], CSCl<sub>2</sub>. ===Coordination chemistry=== CS<sub>2</sub> is a ligand for many metal complexes, forming pi complexes. One example is CpCo([[hapticity|η<sup>2</sup>]]-CS<sub>2</sub>)(PMe<sub>3</sub>).<ref>{{cite journal | author = Werner, H. | title = Novel Coordination Compounds formed from CS<sub>2</sub> and Heteroallenes | journal = [[Coordination Chemistry Reviews]] | year = 1982 | volume = 43 | pages = 165–185 | doi = 10.1016/S0010-8545(00)82095-0}}</ref> ==Commercial Availability== CS<sub>2</sub>, being highly flammable and having one of the lowest autoignition temperatures, cannot be transported easily using commercial means. Worldwide exports of this chemical are negligible. ===Pressurized Liquid Nitrogen Based Sample=== [[Johnson Matthey]]'s sister company [[Alfa Aesar]] was the first company to introduce carbon disulfide in the form of pressurized bottle containing a solution of pressurized nitrogen, coupling agent, stablizer, and carbon disulfide, with an active carbon disulfide content of 85%. Dilution with nitrogen rendered contents nonflammable. In 2007 [[Alfa Aesar]] stopped selling carbon disulfide samples. ==Health effects== At very high levels, carbon disulfide may be life-threatening because it affects the [[nervous system]]. Significant safety data come from the viscose rayon Industry, where both carbon disulfide as well as small amounts of [[hydrogen sulfide|H<sub>2</sub>S]] may be present. ==References== {{Reflist}} ==External links== *[http://www.npi.gov.au/database/substance-info/profiles/18.html National Pollutant Inventory: Carbon disulfide] [[Category:Sulfides]] [[Category:Inorganic carbon compounds]] [[Category:Inorganic solvents]] [[Category:Hazardous air pollutants]] [[cs:Sirouhlík]] [[de:Kohlenstoffdisulfid]] [[es:Sulfuro de carbono]] [[fr:Sulfure de carbone]] [[ko:이황화 탄소]] [[id:Karbon disulfida]] [[it:Solfuro di carbonio]] [[lv:Sērogleklis]] [[hu:Szén-diszulfid]] [[nl:Koolstofdisulfide]] [[ja:二硫化炭素]] [[pl:Dwusiarczek węgla]] [[pt:Dissulfeto de carbono]] [[ro:Sulfură de carbon]] [[ru:Сероуглерод]] [[fi:Hiilidisulfidi]] [[sv:Koldisulfid]] [[tr:Karbondisülfür]] [[zh:二硫化碳]]