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]]