Carbon disulfide


Carbon disulfide
Carbon disulfide
Identifiers
CAS number 75-15-0 YesY
PubChem 6348
ChemSpider 6108 YesY
UNII S54S8B99E8 YesY
EC number 200-843-6
UN number 1131
KEGG C19033 N
ChEBI CHEBI:23012 YesY
RTECS number FF6650000
Jmol-3D images Image 1
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 2.9 g/kg (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 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
NFPA 704.svg
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
 N disulfide (verify) (what is: YesY/N?)
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]

Contents

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 tube. It is also used in the manufacture of Bamboo Fiber.[7]

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. ^ a b c 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. ^ Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Oxford: Butterworth-Heinemann. ISBN 0080379419. 
  4. ^ British Crop Protection Council (1987). The Pesticide Manual, A World Compendium, 8th Ed.
  5. ^ http://www.akzonobel.com/sulfurderivatives/products/carbon_disulfide/
  6. ^ J. Mat. Chem., 2006, 141-154 . doi:10.1039/b510858f
  7. ^ http://www.greencores.com/safety.html

External links


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Look at other dictionaries:

  • carbon disulfide — n a colorless flammable poisonous liquid CS2 used as a solvent for rubber and as an insect fumigant called also carbon bisulfide * * * a colorless, flammable, poisonous liquid, CS2, used as a solvent, as a fruit preservative, and for numerous… …   Medical dictionary

  • carbon disulfide — n. a heavy, volatile, colorless liquid, CS2, highly flammable and poisonous, used as a solvent, insecticide, etc …   English World dictionary

  • carbon disulfide — a clear, colorless or faintly yellow, poisonous, flammable liquid, CS2, used chiefly in the manufacture of cellophane, viscose rayon, and pesticides and as a solvent for fats, resins, and rubber. Also called carbon bisulfide. [1865 70] * * * ▪… …   Universalium

  • carbon disulfide — noun A binary compound of carbon and sulfur, CS, a colourless liquid with a not unpleasant smell; used as a specialist solvent, and in the manufacture of organosulfur compounds. Syn: carbon bisulfide …   Wiktionary

  • carbon disulfide — noun Date: 1869 a colorless flammable poisonous liquid CS2 used as a solvent for rubber and as an insect fumigant called also carbon bisulfide …   New Collegiate Dictionary

  • carbon disulfide — noun a toxic colorless flammable liquid (CS2); used in the manufacture of rayon and cellophane and carbon tetrachloride and as a solvent for rubber • Hypernyms: ↑compound, ↑chemical compound …   Useful english dictionary

  • carbon disulfide — car′bon disul′fide n. chem. a clear flammable liquid, CS2, used in making cellophane, rayon, and pesticides and as a solvent • Etymology: 1865–70 …   From formal English to slang

  • Carbon disulfide (data page) — This page provides supplementary chemical data on carbon disulfide. Material Safety Data Sheet The handling of this chemical may incur notable safety precautions. It is highly recommend that you seek the Material Safety Datasheet (MSDS) for this… …   Wikipedia

  • carbon disulfide poisoning — a condition occurring in workers who excessively inhale fumes of carbon disulfide; characteristics include weakness, sleeplessness, and visual impairment, and sometimes gastric ulcers, encephalopathy, and paralysis …   Medical dictionary

  • Carbon diselenide — Carbon diselenide …   Wikipedia


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