Carbon disulfide

Carbon disulfide
	IUPAC name Methanedithione
Identifiers
CAS number	75-15-0
PubChem	6348
ChemSpider	6108
UNII	S54S8B99E8
EC number	200-843-6
UN number	1131
KEGG	C19033
ChEBI	CHEBI:23012
RTECS number	FF6650000
Jmol-3D images	Image 1
	SMILES C(=S)=S ;
	InChI InChI=1S/CS2/c2-1-3 ; Key: QGJOPFRUJISHPQ-UHFFFAOYSA-N InChI=1/CS2/c2-1-3; Key: QGJOPFRUJISHPQ-UHFFFAOYAS ;
Properties
Molecular formula	CS2
Molar mass	76.139 g/mol
Appearance	colorless liquid; impure: light-yellow
Odor	chloroform (pure); foul (commercial)
Density	1.261 g/cm3
Melting point	-110.8 °C, 162 K, -167 °F
Boiling point	46.3 °C, 319 K, 115 °F
Solubility in water	2.9 g/kg (20 °C)
Refractive index (nD)	1.6295
Viscosity	0.363
Structure
Molecular shape	Linear
Dipole moment	zero
Hazards
MSDS	External MSDS
EU Index	006-003-00-3
EU classification	T, Xi, F
R-phrases	R11, R36/38, R48/23, R62, R63
S-phrases	(S1/2), S16, S33, S36/37, S45
NFPA 704	4 3 0
Flash point	-30 °C
Autoignition; temperature	90 °C
Explosive limits	1.3–50%
LD50	3188 mg/kg
Related compounds
Related compounds	Carbon dioxide; Carbonyl sulfide; Carbon diselenide
Supplementary data page
Structure and; properties	n, εr, etc.
Thermodynamic; data	Phase behaviour; Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

"CS2" redirects here. For the software package by Adobe Systems, see Adobe Creative Suite.

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

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:¹

2CH₄ + S₈ → 2CS₂ + 4H₂S

The reaction is analogous to the combustion of methane. Although it is isoelectronic with carbon dioxide, CS₂ is highly flammable:

CS₂ + 3O₂ → CO₂ + 2SO₂

Reactions

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:

2R₂NH + CS₂ → [R₂NH₂⁺[R₂NCS₂⁻

Xanthates form similarly from alkoxides:

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⁻

Chlorination

Chlorination of CS₂ is the principal route to carbon tetrachloride:¹

CS₂ + 3Cl₂ → CCl₄ + S₂Cl₂

This conversion proceeds via the intermediacy of thiophosgene, CSCl₂.

Coordination chemistry

CS₂ is a ligand for many metal complexes, forming pi complexes. One example is CpCo(η²-CS₂)(PMe₃).²

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.³

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.

Commercial availability

CS₂, 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, stabilizer, and carbon disulfide, with an active carbon disulfide content of 85%. Dilution with nitrogen rendered contents nonflammable.^{citation needed}

Uses

Fumigation

Used for fumigation in airtight storage warehouses, airtight flat storages, bins, grain elevators, railroad box cars, shipholds, barges and cereal mills.⁴

Insecticide

Carbon disulfide is used as an insecticide for the fumigation of grains, nursery stock, in fresh fruit conservation and as a soil disinfectant against insects and nematodes.⁵

Solvent

Carbon disulfide is a solvent for phosphorus, sulfur, selenium, bromine, iodine, fats, resins, rubber, and asphalt.⁶ It has been used in the purification of single-walled carbon nanotubes.⁷

Manufacturing

The principal industrial uses of carbon disulfide are the manufacture of viscose rayon, cellophane film, carbon tetrachloride and xanthogenates and electronic vacuum tubes.

Health effects

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.

References

^ ^a ^b ^c Holleman, A. F.; Wiberg, E. (2001), Inorganic Chemistry, San Diego: Academic Press, ISBN 0-12-352651-5
^ 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
^ 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.

External links

[Holleman-1] Holleman, A. F.; Wiberg, E. (2001), Inorganic Chemistry, San Diego: Academic Press, ISBN 0-12-352651-5

[2] 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.

[3] 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

[4] Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth–Heinemann. ISBN 0080379419.

[5] Worthing, C. R.; Hance. R. J. (1991). The Pesticide Manual, A World Compendium (9th ed.). British Crop Protection Council. ISBN 9780948404429.

[6] "Carbon Disulfide". Akzo Nobel.

[7] 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.

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