{{#if:76.139 g/molchloroform (pure)
foul (commercial)chloroform (pure)
foul (commercial)colorless liquid
impure: light-yellowCS21.261 g/cm32.9 g/kg (20 °C)1.62950.363-110.8|! style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Carbon disulfide
Carbon disulfide
File:Carbon-disulfide-3D-vdW.png
Identifiers
CAS number 75-15-0 7pxY
PubChem 6348
ChemSpider 6108 7pxY
UNII S54S8B99E8 7pxY
EC number 200-843-6
UN number 1131
KEGG C19033 7pxN
ChEBI CHEBI:23012 7pxY
RTECS number FF6650000
Jmol-3D images Image 1
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 ICSC 0022



EU Index 006-003-00-3
EU classification Extremely 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
Carbon diselenide
 14pxN (verify) (what is: 10pxY/10pxN?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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]

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.[3]

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.[4]

Solvent

Carbon disulfide is a solvent for phosphorus, sulfur, selenium, bromine, iodine, fats, resins, and rubber.[5] It has been used in the purification of single-walled carbon nanotubes.[6]

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.

See also

References

  1. 1.0 1.1 1.2 Holleman, A. F.; Wiberg, E. (2001), Inorganic Chemistry, San Diego: Academic Press, ISBN 0-12-352651-5
  2. Script error
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  5. "Carbon Disulfide". Akzo Nobel. http://www.akzonobel.com/sulfurderivatives/products/carbon_disulfide/.
  6. Script error

External links