|Jmol-3D images||Image 1|
|Molar mass||76.14 g mol−1|
|Density||1.539 g/cm3 (-186°C)
1.2927 g/cm3 (0 °C)
1.266 g/cm3 (25 °C)
|Melting point||−111.61 °C (−168.90 °F; 161.54 K)|
|Boiling point||46.24 °C (115.23 °F; 319.39 K)|
|Solubility in water||0.258 g/100 mL (0 °C)
0.239 g/100 mL (10 °C)
0.217 g/100 mL (20 °C)
0.014 g/100 mL (50 °C)
|Solubility||Soluble in alcohol, ether, benzene, oil, CHCl3, CCl4|
|Solubility in formic acid||4.66 g/100 g|
|Solubility in dimethyl sulfoxide||45 g/100 g (20.3 °C)|
|Vapor pressure||48.1 kPa (25 °C)
82.4 kPa (40 °C)
|Refractive index (nD)||1.627|
|Viscosity||0.436 cP (0 °C)
0.363 cP (20 °C)
|Dipole moment||0 D (20 °C)|
heat capacity C
|Std enthalpy of
|Gibbs free energy ΔG||64.4 kJ/mol|
|Std enthalpy of
|GHS signal word||Danger|
|GHS hazard statements||H225, H315, H319, H361, H372|
|GHS precautionary statements||P210, P281, P305+351+338, P314
|EU classification||F T Xi|
|R-phrases||R11, R36/38, R48/23, R62, R63|
|S-phrases||(S1/2), S16, S33, S36/37, S45|
|Flash point||−43 °C (−45 °F; 230 K) |
|Autoignition temperature||102 °C (216 °F; 375 K) |
|LD50||3188 mg/kg (rat, oral)|
|Related compounds||Carbon dioxide
|Supplementary data page|
|n, εr, etc.|
Solid, liquid, gas
|Spectral data||UV, IR, NMR, MS|
|Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)|
|(what is: / ?)|
Carbon disulfide is a colorless volatile liquid with the formula CS2. 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 "ether-like" odor, but commercial samples are typically contaminated with foul-smelling impurities, such as carbonyl sulfide.
- 1 Occurrence and manufacture
- 2 Reactions
- 3 Polymerization
- 4 Uses
- 5 Health effects
- 6 See also
- 7 References
- 8 External links
Occurrence and manufacture
Small amounts of carbon disulfide are released by volcanic eruptions and marshes. CS2 once was manufactured by combining carbon (or 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 catalysts:
- 2 CH4 + S8 → 2 CS2 + 4 H2S
- CS2 + 3 O2 → CO2 + 2 SO2
Global production/consumption of carbon disulfide is approximately one million tonnes, with China consuming 49%, followed by India at 13%, mostly for the production of rayon fiber. USA production in 2007 was 56,000 tonnes.
Compared to CO2, CS2 is more reactive toward nucleophiles 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 and is commonly used in the production of the soft fabric viscose.
Addition of nucleophiles
Nucleophiles such as amines afford dithiocarbamates:
- 2 R2NH + CS2 → [R2NH2+][R2NCS2−]
- RONa + CS2 → [Na+][ROCS2−]
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 CS2 with sodium thiolates) are used as flotation agents in mineral processing.
Sodium sulfide affords trithiocarbonate:
- Na2S + CS2 → [Na+]2[CS32−]
This conversion proceeds via the intermediacy of thiophosgene, CSCl2.
Carbon disulfide hydrolase
Carbon disulfide is naturally formed in the mudpots of volcanic solfataras. It serves as a source of hydrogen sulfide, which is an electron donor for certain organisms that oxidize it into sulphuric acid or related sulfur oxides. The hyperthermophilic Acidianus strain was found to convert CS2 into H2S and CO2. The enzyme responsible for this conversion is termed carbon disulfide hydrolase.
The enzyme can be obtained in both apoenzyme and holoenzyme forms. The enzyme is predicted to have an isoelectric point of 5.92 and a molecular mass of 23,576 Da.1 The enzyme is hexadecameric.
The apoenzyme form, lacking the zinc cofactor, has a molecular weight of 382815.4 g/mol. The chloride ion and the 3,6,9,12,15,18,21,24,27,30,33,36,39-tridecaoxahentetracontane-1,41-diol (C28H58O15) are the two main ligands seen on the enzyme in this form. There are 16 polymer chains seen in this form contributing to the heaviness of the enzyme. This form is also sometimes termed the selenomethionine form.
CS2 hydrolase in its holoenzyme has a cofactor bound to it. In this form the only ligand to be found is the zinc ion and the molecular weight of the enzyme overall is 189404.8 g/mol. There are only eight polymer chains seen in this form and this may be due to the fact that the enzyme catalyzes the conversion of CS2 in this form.
The enzyme is similar to that of carbonic anhydrases. The enzyme monomer of CS2 hydrolase displays a typical β-carbonic anhydrase fold and active site. Two of these monomers form a closely intertwined dimer with a central β-sheet capped by anα-helical domain. Four dimers form a square octameric ring through interactions of the long arms at the N and C termini. Similar ring structures have been seen in strains of carbonic anhydrases, however, in CS2 hydrolase, two octameric rings form a hexadecamer by interlocking at right angles to each other. This results in the blocking of the entrance to the active site and the formation of a single 15-Å-long, highly hydrophobic tunnel that functions as a specificity filter. This provides a key difference between carbonic anhydrase and CS2 hydrolase. This tunnel determines the enzyme’s substrate specificity for CS2, which is hydrophobic as well.
The mechanism by this hydrolase converts CS2 into H2S is similar to that of how carbonic anhydrase hydrates CO2 to HCO3−. This similarity points to a likely mechanism. The zinc at the active site is tetrahedral, being coordinated by Cys 35, His 88, Cys 91 and water. The water is deprotonated to give a zinc hydroxide that adds the substrate to give a Zn-O-C(S)SH intermediate. A similar process is proposed to convert COS into CO2.
- CS2 + H2O → COS + H2S
- COS + H2O → CO2 + H2S
CS2 polymerizes upon photolysis or under high pressure to give an insoluble material called "Bridgman's black", named after the discoverer of the polymer, P. W. Bridgman. Trithiocarbonate (-S-C(S)-S-) linkages comprise, in part, the backbone of the polymer, which is a semiconductor.
At high levels, carbon disulfide may be life-threatening because it affects the nervous system. Significant safety data comes from the viscose rayon industry, where both carbon disulfide as well as small amounts of H2S may be present.
- Seidell, Atherton; Linke, William F. (1952). Solubilities of Inorganic and Organic Compounds. Van Nostrand.
- Carbon disulfide in Linstrom, P.J.; Mallard, W.G. (eds.) NIST Chemistry WebBook, NIST Standard Reference Database Number 69. National Institute of Standards and Technology, Gaithersburg MD. http://webbook.nist.gov (retrieved 2014-05-27)
- Sigma-Aldrich Co., Carbon disulfide. Retrieved on 2014-05-27.
- Holleman, A. F.; Wiberg, E. (2001), Inorganic Chemistry, San Diego: Academic Press, ISBN 0-12-352651-5
- "Carbon Disulfide report from IHS Chemical". Retrieved June 15, 2013.
- "Chemical profile: carbon disulfide from ICIS.com". Retrieved June 15, 2013.
- Werner, H. (1982). "Novel Coordination Compounds formed from CS2 and Heteroallenes". Coordination Chemistry Reviews 43: 165–185. doi:10.1016/S0010-8545(00)82095-0.
- Smeulders, MJ.; Barends, TR.; Pol, A.; Scherer, A.; Zandvoort, MH.; Udvarhelyi, A.; Khadem, AF.; Menzel, A.; Hermans, J.; Shoeman, RL.; Wessels, HJ.; Van den Heuvel, LP.; Russ, L.; Schlichting, I.; Jetten, MS.; Op den Camp, HJ. “Evolution of a New Enzyme for Carbon Disulphide Conversion by an AcidothermophilicArchaeon” Nature, 2011, 487, 412-416. doi:10.1038/nature10464
- Smeulders, MJ.; Barends, TR.; Pol, A.; Scherer, A.; Zandvoort, MH.; Udvarhelyi, A.; Khadem, AF.; Menzel, A.; Hermans, J.; Shoeman, RL.; Wessels, HJ.; Van den Heuvel, LP.; Russ, L.; Schlichting, I.; Jetten, MS.; Op den Camp, HJ. RCSB Protein Data Bank, 2011, DOI:10.2210/pdb3teo/pdb, DOI:10.2210/pdb3ten/pdb
- Smeulders, MJ.; Barends, TR.; Pol, A.; Scherer, A.; Zandvoort, MH.; Udvarhelyi, A.; Khadem, AF.; Menzel, A.; Hermans, J.; Shoeman, RL.; Wessels, HJ.; Van den Heuvel, LP.; Russ, L.; Schlichting, I.; Jetten, MS.; Op den Camp, HJ. Protein Data Bank Japan, 2012, PDB ID: 3teo, 3ten
- Ochiai, Bungo; Endo, Takeshi "Carbon dioxide and carbon disulfide as resources for functional polymers" Progress in Polymer Science (2005), 30, 183-215. doi:10.1016/j.progpolymsci.2005.01.005
- Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 0080379419.
- Worthing, C. R.; Hance. R. J. (1991). The Pesticide Manual, A World Compendium (9th ed.). British Crop Protection Council. ISBN 9780948404429.
- "Carbon Disulfide". Akzo Nobel.
- Park, T.-J.; Banerjee, S.; Hemraj-Benny, T.; Wong, S. S. (2006). "Purification strategies and purity visualization techniques for single-walled carbon nanotubes". Journal of Materials Chemistry 16 (2): 141–154. doi:10.1039/b510858f.
|Wikimedia Commons has media related to Carbon disulfide.|
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