Carbon disulfide Information & Carbon disulfide Links at HealthHaven.com

Carbon disulfide
IUPAC name	Carbon disulfide
Other names	Dithiocarbonic anhydride, carbon bisulfide
Identifiers
CAS number	75-15-0
PubChem	6348
EC number	200-843-6
UN number	1131
RTECS number	FF6650000
SMILES	S=C=S
InChI	1/CS2/c2-1-3
InChI key	QGJOPFRUJISHPQ-UHFFFAOYAS
ChemSpider ID	6108
Properties
Molecular formula	CS2
Molar mass	76.139 g/mol
Appearance	colorless liquid; impure: light-yellow
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	0.29 g/100 ml (20 °C)
Refractive index (nD)	1.6295
Structure
Molecular shape	Linear
Dipole moment	zero
Hazards
MSDS	External MSDS
EU Index	006-003-00-3
EU classification	Flammable (F); Repr. Cat. 3; Toxic (T); Irritant (Xi)
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
Supplementary data page
Structure and; properties	n, εr, etc.
Thermodynamic; data	Phase behaviour; Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
	(what is this?) (verify); 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]

[edit] 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 to carbon dioxide, CS₂ is highly flammable:

CS₂ + 3O₂ → CO₂ + 2SO₂

[edit] 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.

[edit] 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⁻]

[edit] 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.

[edit] Coordination chemistry

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

[edit] 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.

[edit] 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.

[edit] 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 H₂S may be present.

[edit] See also

[edit] 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.

[edit] External links

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

[1] 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.

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