Carbon disulfide

Last updated
Carbon disulfide
Carbon-disulfide-2D-dimensions.png
Carbon-disulfide-3D-vdW.png
Names
IUPAC name
Carbon disulfide
Systematic IUPAC name
Methanedithione
Other names
Carbon bisulfide
Identifiers
3D model (JSmol)
1098293
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.767 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-843-6
KEGG
PubChem CID
RTECS number
  • FF6650000
UNII
UN number 1131
  • InChI=1S/CS2/c2-1-3 Yes check.svgY
    Key: QGJOPFRUJISHPQ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/CS2/c2-1-3
    Key: QGJOPFRUJISHPQ-UHFFFAOYAS
  • S=C=S
Properties
CS2
Molar mass 76.13 g·mol−1
AppearanceColorless liquid
Impure: light-yellow
Odor Pleasant, ether- or chloroform-like
Commercial: Foul, like rotten radish
Density 1.539 g/cm3 (−186°C)
1.2927 g/cm3 (0 °C)
1.266 g/cm3 (25 °C) [1]
Melting point −111.61 °C (−168.90 °F; 161.54 K)
Boiling point 46.24 °C (115.23 °F; 319.39 K)
2.58 g/L (0 °C)
2.39 g/L (10 °C)
2.17 g/L (20 °C) [2]
0.14 g/L (50 °C) [1]
Solubility Soluble in alcohol, ether, benzene, oil, CHCl3, CCl4
Solubility in formic acid 4.66 g/100 g [1]
Solubility in dimethyl sulfoxide 45 g/100 g (20.3 °C) [1]
Vapor pressure 48.1 kPa (25 °C)
82.4 kPa (40 °C) [3]
−42.2·10−6 cm3/mol
1.627 [4]
Viscosity 0.436 cP (0 °C)
0.363 cP (20 °C)
Structure
Linear
0 D (20 °C) [1]
Thermochemistry
75.73 J/(mol·K) [1]
Std molar
entropy (S⦵298)
151 J/(mol·K) [1]
88.7 kJ/mol [1]
64.4 kJ/mol [1]
1687.2 kJ/mol [3]
Hazards
Occupational safety and health (OHS/OSH):
Inhalation hazards
Irritant; neurotoxic
Eye hazards
Irritant
Skin hazards
Irritant
GHS labelling: [4]
GHS-pictogram-flamme.svg GHS-pictogram-skull.svg GHS-pictogram-silhouette.svg
Danger
H225, H315, H319, H361, H372
P210, P281, P305+P351+P338, P314
ICSC 0022
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
4
0
Flash point −43 °C (−45 °F; 230 K) [1]
102 °C (216 °F; 375 K) [1]
Explosive limits 1.3–50% [5]
Lethal dose or concentration (LD, LC):
3188 mg/kg (rat, oral)
>1670 ppm (rat, 1 h)
15500 ppm (rat, 1 h)
3000 ppm (rat, 4 h)
3500 ppm (rat, 4 h)
7911 ppm (rat, 2 h)
3165 ppm (mouse, 2 h) [6]
4000 ppm (human, 30 min) [6]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 20 ppm C 30 ppm 100 ppm (30-minute maximum peak) [5]
REL (Recommended)
TWA 1 ppm (3 mg/m3) ST 10 ppm (30 mg/m3) [skin] [5]
IDLH (Immediate danger)
500 ppm [5]
Related compounds
Related compounds
 Carbon dioxide
Carbonyl sulfide
Carbon diselenide
Supplementary data page
Carbon disulfide (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Carbon disulfide (also spelled as carbon disulphide) is an inorganic compound with the chemical formula CS2 and structure S=C=S. It is a colorless, flammable, neurotoxic liquid that is used as a building block in organic synthesis. Pure carbon disulfide has a pleasant, ether- or chloroform-like odor, but commercial samples are usually yellowish and are typically contaminated with foul-smelling impurities. [7]

Contents

History

In 1796, the German chemist Wilhelm August Lampadius (1772–1842) first prepared carbon disulfide by heating pyrite with moist charcoal. He called it "liquid sulfur" (flüssig Schwefel). [8] The composition of carbon disulfide was finally determined in 1813 by the team of the Swedish chemist Jöns Jacob Berzelius (1779–1848) and the Swiss-British chemist Alexander Marcet (1770–1822). [9] Their analysis was consistent with an empirical formula of CS2. [10]

Occurrence, manufacture, properties

Small amounts of carbon disulfide are released by volcanic eruptions and marshes. CS2 once was manufactured by combining carbon (or coke) and sulfur at 800–1000 °C. [11]

C + 2S → CS2

A lower-temperature reaction, requiring only 600 °C, utilizes natural gas as the carbon source in the presence of silica gel or alumina catalysts: [7]

2 CH4 + S8 → 2 CS2 + 4 H2S

The reaction is analogous to the combustion of methane.

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. [12] United States production in 2007 was 56,000 tonnes. [13]

Solvent

Carbon disulfide is a solvent for phosphorus, sulfur, selenium, bromine, iodine, fats, resins, rubber, and asphalt. [14]

Extraterrestrial

In March 2024, traces of CS2 were likely detected in the atmosphere of the temperate mini-Neptune planet TOI-270 d by James Webb Space Telescope. [15]

Reactions

Combustion of CS2 affords sulfur dioxide according to this ideal stoichiometry:

CS2 + 3 O2 → CO2 + 2 SO2

With nucleophiles

For example, amines afford dithiocarbamates: [16]

2 R2NH + CS2 → [R2NH2+][R2NCS2−]

Xanthates form similarly from alkoxides: [16]

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.

Upon treatment with sodium sulfide, carbon disulfide affords trithiocarbonate: [16]

Na2S + CS2 → [Na+]2[CS32−]

Carbon disulfide does not hydrolyze readily, although the process is catalyzed by an enzyme carbon disulfide hydrolase.

Compared to the isoelectronic carbon dioxide, CS2 is a weaker electrophile. While, however, reactions of nucleophiles with CO2 are highly reversible and products are only isolated with very strong nucleophiles, the reactions with CS2 are thermodynamically more favored allowing the formation of products with less reactive nucleophiles. [17]

Reduction

Reduction of carbon disulfide with sodium affords sodium 1,3-dithiole-2-thione-4,5-dithiolate together with sodium trithiocarbonate: [18]

4 Na + 4 CS2 → Na2C3S5 + Na2CS3

Chlorination

Chlorination of CS2 provides a route to carbon tetrachloride: [7]

CS2 + 3 Cl2 → 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)(PMe 3). [19]

Polymerization

CS2 polymerizes upon photolysis or under high pressure to give an insoluble material called car-sul or "Bridgman's black", named after the discoverer of the polymer, Percy Williams Bridgman. [20] Trithiocarbonate (-S-C(S)-S-) linkages comprise, in part, the backbone of the polymer, which is a semiconductor. [21]

Uses

The principal industrial uses of carbon disulfide, consuming 75% of the annual production, are the manufacture of viscose rayon and cellophane film. [22]

It is also a valued intermediate in chemical synthesis of carbon tetrachloride. It is widely used in the synthesis of organosulfur compounds such as xanthates, which are used in froth flotation, a method for extracting metals from their ores. Carbon disulfide is also a precursor to dithiocarbamates, which are used as drugs (e.g. Metam sodium) and rubber chemistry.

Niche uses

Carbon disulfide insecticide ad from the 1896 issue of The American Elevator and Grain Trade magazine Carbon disulfide insecticide ad, 1896 - The American elevator and grain trade (IA CAT31053470064) (page 3 crop).jpg
Carbon disulfide insecticide ad from the 1896 issue of The American Elevator and Grain Trade magazine

It can be used in fumigation of airtight storage warehouses, airtight flat storage, bins, grain elevators, railroad box cars, ship holds, barges and cereal mills. [23] Carbon disulfide is also used as an insecticide for the fumigation of grains, nursery stock, in fresh fruit conservation and as a soil disinfectant against insects and nematodes. [24]

Health effects

Carbon disulfide has been linked to both acute and chronic forms of poisoning, with a diverse range of symptoms. [25]

Concentrations of 500–3000 mg/m3 cause acute and subacute poisoning. These include a set of mostly neurological and psychiatric symptoms, called encephalopathia sulfocarbonica. Symptoms include acute psychosis (manic delirium, hallucinations), paranoic ideas, loss of appetite, gastrointestinal and sexual disorders, polyneuritis, myopathy, and mood changes (including irritability and anger). Effects observed at lower concentrations include neurological problems (encephalopathy, psychomotor and psychological disturbances, polyneuritis, abnormalities in nerve conduction), hearing problems, vision problems (burning eyes, abnormal light reactions, increased ophthalmic pressure), heart problems (increased deaths for heart disease, angina pectoris, high blood pressure), and reproductive problems (increased miscarriages, immobile or deformed sperm), and decreased immune response. [26] [27]

Occupational exposure to carbon disulfide is also associated with cardiovascular disease, particularly stroke. [28]

In 2000, the WHO believed that health harms were unlikely at levels below 100 μg/m3, and set this as a guideline level.[ needs update ] Carbon sulfide can be smelled at levels above 200 μg/m3, and the WHO recommended a sensory guideline of below 20 μg/m3. Exposure to carbon disulfide is well-established to be harmful to health in concentrations at or above 30 mg/m3 Changes in the function of the central nervous system have been observed at concentrations of 20–25 mg/m3. There are also reports of harms to health at 10 mg/m3, for exposures of 10–15 years, but the lack of good data on past exposure levels make the association of these harms with concentrations of 10 mg/m3 findings uncertain. The measured concentration of 10 mg/m3 may be equivalent to a concentration in the general environment of 1 mg/m3. [26]

Environmental sources

The primary source of carbon disulfide in the environment is rayon factories. [26] Most global carbon disulfide emissions come from rayon production, as of 2008. [29] Other sources include the production of cellophane, carbon tetrachloride, [29] carbon black, and sulfur recovery. Carbon disulfide production also emits carbon disulfide. [30]

As of 2004, about 250 g of carbon disulfide is emitted per kilogram of rayon produced. About 30 g of carbon disulfide is emitted per kilogram of carbon black produced. About 0.341 g of carbon disulfide is emitted per kilogram of sulfur recovered. [30]

Japan has reduced carbon disulfide emissions per kilogram of rayon produced, but in other rayon-producing countries, including China, emissions are assumed to be uncontrolled (based on global modelling and large-scale free-air concentration measurements). Rayon production is steady or decreasing except in China, where it is increasing, as of 2004. [30] Carbon black production in Japan and Korea uses incinerators to destroy about 99% of the carbon disulfide that would otherwise be emitted. [30] When used as a solvent, Japanese emissions are about 40% of the carbon disulfide used; elsewhere, the average is about 80%. [30]

Most rayon production uses carbon sulfide. [31] [32] One exception is rayon made using the lyocell process, which uses a different solvent; as of 2018 the lyocell process is not widely used, because it is more expensive than the viscose process. [33] [34] Cuprammonium rayon also does not use carbon disulfide.

Historic and current exposure

Industrial workers working with carbon disulfide are at high risk. Emissions may also harm the health of people living near rayon plants. [26]

Concerns about carbon disulfide exposure have a long history. [22] [35] [36] : 79  Around 1900, carbon disulfide came to be widely used in the production of vulcanized rubber. The psychosis produced by high exposures was immediately apparent (it has been reported with 6 months of exposure [26] ). Sir Thomas Oliver told a story about a rubber factory that put bars on its windows so that the workers would not jump out to their deaths (suicide). [36] : 17  Carbon disulfide's use in the US as a heavier-than-air burrow poison for Richardson's ground squirrel also led to reports of psychosis. No systematic medical study of the issue was published, and knowledge was not transferred to the rayon industry. [31]

The first large epidemiological study of rayon workers was done in the US in the late 1930s, and found fairly severe effects in 30% of the workers. Data on increased risks of heart attacks and strokes came out in the 1960s. Courtaulds, a major rayon manufacturer, worked hard to prevent publication of this data in the UK. [31] Average concentrations in sampled rayon plants were reduced from about 250 mg/m3 in 1955–1965 to about 20–30 mg/m3 in the 1980s (US figures only?[ United States-centric ]). [26] Rayon production has since largely moved to the developing world, especially China, Indonesia and India. [32] [31]

Rates of disability in modern factories are unknown, as of 2016. [32] [37] Current manufacturers using the viscose process do not provide any information on harm to their workers. [31] [32]

See also

Related Research Articles

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Hydrogen sulfide is a chemical compound with the formula H2S. It is a colorless chalcogen-hydride gas, and is poisonous, corrosive, and flammable, with trace amounts in ambient atmosphere having a characteristic foul odor of rotten eggs. Swedish chemist Carl Wilhelm Scheele is credited with having discovered the chemical composition of purified hydrogen sulfide in 1777.

<span class="mw-page-title-main">Cellophane</span> Thin, transparent sheet made of cellulose

Cellophane is a thin, transparent sheet made of regenerated cellulose. Its low permeability to air, oils, greases, bacteria, and liquid water makes it useful for food packaging. Cellophane is highly permeable to water vapour, but may be coated with nitrocellulose lacquer to prevent this.

<span class="mw-page-title-main">Rayon</span> Cellulose-based semi-synthetic fiber

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Red Scar Works was built in 1939 by Courtaulds and produced rayon. It was located in Ribbleton Preston off Longridge Road. The closure of the works was announced in November 1979 and the issue raised in the UK Parliament House of Commons by the constituency MP. At the time of closure approximately 2,600 people were employed there but there were approximately 4,000 at its peak. It was the largest rayon producing site in Britain. Two main products were manufactured with one being tyre cord by a process known as CSPT – Continuous Spinning Process Tenasco. Two main denier of this product were manufactured. The other product was a general textile called Bright. A range of deniers of this were produced in a range of colours. The trade name for the coloured product was Duracol. At the time of closure, one reason given by management for the closure was the rising popularity of steel belt radial tires thus reducing demand for tyre cord.

References

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  17. ↑ Li, Zhen; Mayer, Robert J.; Ofial, Armin R.; Mayr, Herbert (2020-04-27). "From Carbodiimides to Carbon Dioxide: Quantification of the Electrophilic Reactivities of Heteroallenes". Journal of the American Chemical Society. 142 (18): 8383–8402. doi:10.1021/jacs.0c01960. PMID   32338511. S2CID   216557447.
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  20. ↑ Bridgman, P.W. (1941). "Explorations toward the limit of utilizable pressures". Journal of Applied Physics. 12 (6): 461–469. Bibcode:1941JAP....12..461B. doi:10.1063/1.1712926.
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  24. ↑ Worthing, Charles R.; Hance, Raymond J. (1991). The Pesticide Manual, A World Compendium (9th ed.). British Crop Protection Council. ISBN   9780948404429.
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