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| Names | |
|---|---|
| IUPAC name Carbon disulfide | |
| Systematic IUPAC name Methanedithione | |
| Other names Carbon bisulfide Dithiocarbonic anhydride[1] | |
| Identifiers | |
| |
3D model (JSmol) | |
| 1098293 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.000.767 |
| EC Number |
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| KEGG |
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| RTECS number |
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| UNII | |
| UN number | 1131 |
| |
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| Properties | |
| CS2 | |
| Molar mass | 76.13 g·mol−1 |
| Appearance | Colorless liquid Impure: light-yellow |
| Odor | Pleasant,ether- orchloroform-like Commercial: Foul, like rottenradish |
| Density | 1.539 g/cm3 (−186°C) 1.2927 g/cm3 (0 °C) 1.266 g/cm3 (25 °C)[2] |
| 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)[3] 0.14 g/L (50 °C)[2] | |
| Solubility | Soluble inalcohol,ether,benzene,oil,CHCl3,CCl4 |
| Solubility informic acid | 4.66 g/100 g[2] |
| Solubility indimethyl sulfoxide | 45 g/100 g (20.3 °C)[2] |
| Vapor pressure | 48.1 kPa (25 °C) 82.4 kPa (40 °C)[4] |
| −42.2·10−6 cm3/mol | |
Refractive index (nD) | 1.627[5] |
| Viscosity | 0.436cP (0 °C) 0.363 cP (20 °C) |
| Structure | |
| Linear | |
| 0 D (20 °C)[2] | |
| Thermochemistry | |
| 75.73 J/(mol·K)[2] | |
Std molar entropy(S⦵298) | 151 J/(mol·K)[2] |
Std enthalpy of formation(ΔfH⦵298) | 88.7 kJ/mol[2] |
Gibbs free energy(ΔfG⦵) | 64.4 kJ/mol[2] |
Std enthalpy of combustion(ΔcH⦵298) | 1687.2 kJ/mol[4] |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Inhalation hazards | Irritant; neurotoxin |
Eye hazards | Irritant |
Skin hazards | Irritant |
| GHS labelling:[5][8] | |
    | |
| Danger | |
| H225,H315,H319,H332,H361fd,H372 | |
| P202,P210,P281,P303+P361+P353,P304+P340+P312,P305+P351+P338,P308+P313 ICSC 0022 | |
| NFPA 704 (fire diamond) | |
| Flash point | −43 °C (−45 °F; 230 K)[2] |
| 102 °C (216 °F; 375 K)[2] | |
| Explosive limits | 1.3–50%[6] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 3188 mg/kg (rat, oral) |
LC50 (median concentration) | >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)[7] |
LCLo (lowest published) | 4000 ppm (human, 30 min)[7] |
| NIOSH (US health exposure limits): | |
PEL (Permissible) | TWA 20 ppm C 30 ppm 100 ppm (30-minute maximum peak)[6] |
REL (Recommended) | TWA 1 ppm (3 mg/m3) ST 10 ppm (30 mg/m3) [skin][6] |
IDLH (Immediate danger) | 500 ppm[6] |
| 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 theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Carbon disulfide (also spelled ascarbon disulphide) is aninorganic compound with thechemical formulaCS2 andstructureS=C=S. It is also considered as the anhydride ofthiocarbonic acid.[9] It is a colorless, flammable,neurotoxic liquid that is used as a building block in organic synthesis. Pure carbon disulfide has a pleasant,ether- orchloroform-like odor, but commercial samples are usually yellowish and are typically contaminated with foul-smelling impurities.[10]
In 1796, the German chemistWilhelm August Lampadius (1772–1842) first prepared carbon disulfide by heatingpyrite with moist charcoal. He called it "liquid sulfur" (flüssig Schwefel).[11] The composition of carbon disulfide was finally determined in 1813 by the team of the Swedish chemistJöns Jacob Berzelius (1779–1848) and the Swiss-British chemistAlexander Marcet (1770–1822).[12] Their analysis was consistent with anempirical formula of CS2.[13]
Small amounts of carbon disulfide are released byvolcanic eruptions andmarshes. CS2 once was manufactured by combiningcarbon (orcoke) andsulfur at 800–1000 °C.[14]
A lower-temperature reaction, requiring only 600 °C, utilizesnatural gas as the carbon source in the presence ofsilica gel oraluminacatalysts:[10]
The reaction is analogous to the combustion ofmethane.
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.[15] United States production in 2007 was 56,000 tonnes.[16]
Carbon disulfide can dissolve a variety ofnonpolar chemicals includingphosphorus, sulfur,selenium,bromine,iodine,fats,resins,rubber, andasphalt.[17]
In March 2024, possible traces of CS2 were detected in the atmosphere of the temperatemini-Neptune planetTOI-270 d by theJames Webb Space Telescope.[18]
Combustion of CS2 affordssulfur dioxide according to this ideal stoichiometry:
Compared to theisoelectroniccarbon dioxide, CS2 is a weakerelectrophile. While, however, reactions ofnucleophiles 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.[19]
For example, amines afforddithiocarbamates:[20]
Xanthates form similarly fromalkoxides:[20]
This reaction is the basis of the manufacture of regeneratedcellulose, the main ingredient ofviscose,rayon, andcellophane. Both xanthates and the relatedthioxanthates (derived from treatment of CS2 with sodiumthiolates) are used asflotation agents in mineral processing.
Upon treatment withsodium sulfide, carbon disulfide affordstrithiocarbonate:[20]
Carbon disulfide does not hydrolyze readily, although the process is catalyzed byan enzyme.
Reduction of carbon disulfide withsodium affordssodium 1,3-dithiole-2-thione-4,5-dithiolate together with sodiumtrithiocarbonate:[21]
Chlorination of CS2 provides a route tocarbon tetrachloride:[10]
This conversion proceeds via the intermediacy ofthiophosgene, CSCl2.
CS2 is a ligand for many metal complexes, forming pi complexes. One example isCpCo(η2-CS2)(PMe3).[22]
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.[23] Trithiocarbonate (-S-C(S)-S-) linkages comprise, in part, the backbone of the polymer, which is asemiconductor.[24]
The principal industrial uses of carbon disulfide, consuming 75% of the annual production, are the manufacture ofviscose rayon andcellophane film.[25]
It is also a valued intermediate in chemical synthesis ofcarbon tetrachloride. It is widely used in the synthesis oforganosulfur compounds such asxanthates, which are used infroth flotation, a method for extracting metals from their ores. Carbon disulfide is also a precursor todithiocarbamates, which are used as drugs (e.g.Metam sodium) andrubber chemistry.
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It can be used infumigation of airtight storage warehouses, airtight flat storage, bins,grain elevators, railroadbox cars, ship holds,barges, and cereal mills.[26] Carbon disulfide is also used as aninsecticide for the fumigation of grains, nursery stock, in fresh fruit conservation, and as asoil disinfectant against insects andnematodes.[27]
It can also be used for theBarking dog reaction.
Carbon disulfide has been linked to bothacute and chronic forms ofpoisoning, with a diverse range of symptoms.[28]
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 acutepsychosis (manicdelirium,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, increasedophthalmic pressure), heart problems (increased deaths for heart disease,angina pectoris,high blood pressure), reproductive problems (increasedmiscarriages,immobile ordeformed sperm), and decreased immune response.[29][30]
Occupational exposure to carbon disulfide is also associated withcardiovascular disease, particularlystroke.[31]
In 2000, theWorld Health Organization (WHO) considered that health harms were unlikely at levels below 100 μg/m3 over an averaging time of 24 hours, and recommended this as a guideline level.[32] Carbon disulfide 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.[29]
The primary source of carbon disulfide in the environment israyon factories.[29] Most global carbon disulfide emissions come from rayon production, as of 2008.[33] Other sources include the production ofcellophane,carbon tetrachloride,[33]carbon black, and sulfur recovery. Carbon disulfide production also emits hydrogen sulfide.[34]
As of 2004[update], 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.[34]
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[update].[34] Carbon black production in Japan and Korea uses incinerators to destroy about 99% of the carbon disulfide that would otherwise be emitted.[34] When used as asolvent, Japanese emissions are about 40% of the carbon disulfide used; elsewhere, the average is about 80%.[34]
Most rayon production uses carbon sulfide.[35][36] One exception is rayon made using thelyocell process, which uses a different solvent; as of 2018[update] the lyocell process is not widely used, because it is more expensive than the viscose process.[37][38]Cuprammonium rayon also does not use carbon disulfide.
Industrial workers working with carbon disulfide are at high risk. Emissions may also harm the health of people living near rayon plants.[29]
Concerns about carbon disulfide exposure have a long history.[25][39][40]: 79 Around 1900, carbon disulfide came to be widely used in the production ofvulcanized rubber. Thepsychosis produced by high exposures was soon apparent (it has been reported with 6 months of exposure[29]).Sir Thomas Oliver told a story about arubber factory that put bars on its windows so that the workers would notleap out to their deaths.[40]: 17 Carbon disulfide use in the US as a heavier-than-air burrow poison forRichardson'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.[35]
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 late 1960s.[41]Courtaulds, a major rayon manufacturer, worked hard to prevent publication of this data in the UK.[35] 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]).[29] Rayon production has since largely moved to the developing world, especially China, Indonesia and India.[36][35]
Rates ofdisability in factories are unknown as of 2016[update].[36][42] Manufacturers using theviscose process do not provide any information on harm to their workers.[35][36]
in 1915,...[of 16] carbon disulfide poisoning cases....one worker had been briefly committed to an asylum and several others had experienced nervous system complaints...
| International | |
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| National | |
| Other | |
