Carbon disulfide

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.[7]
 Carbon disulfide

Names

IUPAC name
Methanedithione

Other names
Carbon bisulfide

Identifiers
CAS Number 75-15-0  

3D model (JSmol) Interactive image

ChEBI CHEBI:23012  
ChemSpider 6108  

ECHA InfoCard 100.000.767

EC Number 200-843-6

KEGG C19033  

PubChem CID 6348

RTECS number FF6650000

UNII S54S8B99E8  

UN number 1131
CompTox Dashboard DTXSID6023947
(EPA)

InChI
InChI=1S/CS2/c2-1-3 
Key: QGJOPFRUJISHPQ-UHFFFAOYSA-N 

InChI=1/CS2/c2-1-3
Key: QGJOPFRUJISHPQ-UHFFFAOYAS

SMILES
C(=S)=S

Properties
Chemical formula CS2

Molar mass 76.13 g·mol−1

Appearance Colorless liquid

Impure: light-yellow

Odor Chloroform (pure)

Foul (commercial)

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)

Solubility in water 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 4.66 g/100 g[1]

acid

Solubility in dimethyl 45 g/100 g (20.3

sulfoxide °C)[1]

Vapor pressure 48.1 kPa (25 °C)

 82.4 kPa (40 °C)[3]

Magnetic −42.2·10−6 cm3/mol

susceptibility (χ)
Refractive index (nD) 1.627[4]

Viscosity 0.436 cP (0 °C)

0.363 cP (20 °C)

Structure
Molecular shape Linear
Dipole moment 0 D (20 °C)[1]

Thermochemistry

Heat capacity (C) 75.73 J/(mol·K)[1]

Std molar 151 J/(mol·K)[1]
entropy (So298)

Std enthalpy of 88.7 kJ/mol[1]

formation (ΔfH 298)

Gibbs free energy 64.4 kJ/mol[1]

(ΔfG˚)

Std enthalpy of 1687.2 kJ/mol[3]

combustion
(ΔcH 298)

Hazards

Safety data sheet See: data page

GHS pictograms [4]

GHS Signal word Danger

GHS hazard H225, H315, H319,
statements
H361, H372[4]

GHS precautionary P210, P281,

statements
P305+351+338,
 P314[4]
ICSC 0022
Inhalation hazard Irritant; toxic

Eye hazard Irritant

Skin hazard Irritant

NFPA 704 4
3 0
(fire diamond)

Flash point −43 °C (−45 °F;

230 K)[1]

Autoignition 102 °C (216 °F;

temperature
375 K)[1]

Explosive limits 1.3–50%[5]

Lethal dose or concentration (LD, LC):

LD50 (median dose) 3188 mg/kg (rat,
 oral)
LC50 (median >1670 ppm (rat, 1 h)
concentration) 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]

LCLo (lowest 4000 ppm (human,

published) 30 min)[6]

NIOSH (US health exposure limits):

PEL (Permissible) TWA 20 ppm C 30
ppm 100 ppm (30-
minute maximum
peak)[5]
 REL TWA 1 ppm (3
(Recommended)
mg/m3) ST 10 ppm
(30 mg/m3) [skin][5]

IDLH (Immediate 500 ppm[5]

danger)
Related compounds
Related compounds Carbon dioxide
Carbonyl sulfide
Carbon diselenide

Supplementary data page

Structure and Refractive index (n),
properties
Dielectric constant
(εr), etc.

Thermodynamic Phase behaviour

data
solid–liquid–gas
Spectral data UV, IR, NMR, MS
Except where otherwise noted, data are
given for materials in their standard state (at
25 °C [77 °F], 100 kPa).

 verify (what is   ?)

Infobox references

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
high temperatures.
 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.[8] United
States production in 2007 was 56,000
tonnes.[9]

Solvent …

Carbon disulfide is a solvent for

phosphorus, sulfur, selenium, bromine,
iodine, fats, resins, rubber, and
asphalt.[10] It has been used in the
purification of single-walled carbon
nanotubes.[11]

Reactions
CS2 is highly flammable. Its combustion
affords Sulfur dioxide according to this
ideal stoichiometry:
 CS2 + 3 O2 → CO2 + 2 SO2

With nucleophiles …

Being isoelectronic with carbon dioxide

but more electrophilic, it is reactive
toward nucleophiles. These differences
in reactivity can be attributed to the
weaker π donor-ability of the sulfido
centers, which renders the carbon more
electrophilic. Amines afford
dithiocarbamates:

2 R2NH + 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−]

ICarbon disulfide does not hydrolyze

readily, although the process is catalyzed
by an enzyme carbon disulfide hydrolase.
Reduction …

Reduction of carbon disulfide with

sodium affords sodium 1,3-dithiole-2-
thione-4,5-dithiolate together with
sodium trithiocarbonate:[12]

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)(PMe3).[13]

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.
Trithiocarbonate (-S-C(S)-S-) linkages
comprise, in part, the backbone of the
polymer, which is a semiconductor.[14]
Uses
The principal industrial uses of carbon
disulfide, consuming 75% of the annual
production, are the manufacture of
viscose rayon and cellophane film.[15]

It is also a valued intermediate in

chemical synthesis of carbon
tetrachloride. It is widely used in the
synthesis of organosulfur compounds
such as metam sodium, xanthates,
dithiocarbamates, which are used in
extractive metallurgy and rubber
chemistry.

Niche uses …
It can be used in fumigation of airtight
storage warehouses, airtight flat
storages, bins, grain elevators, railroad
box cars, shipholds, barges and cereal
mills.[16] 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.[17]

Health effects
Carbon disulfide has been linked to both
acute and chronic forms of poisoning,
with a diverse range of symptoms.[18]
Typical recommended TLV is 30 mg/m3,
10 ppm. Possible symptoms include, but
are not limited to, tingling or numbness,
loss of appetite, blurred vision, cramps,
muscle weakness, pain,
neurophysiological impairment, priapism,
erectile dysfunction, psychosis, keratitis,
and death by respiratory failure.[15][19]

Occupational exposure to carbon

disulfide is associated with
cardiovascular disease, particularly
stroke.[20]

See also
Carbon monosulfide
Carbon subsulfide
 Carbon diselenide

References
1. "Properties of substance: carbon
disulfide" . chemister.ru.
2. Seidell, Atherton; Linke, William F.
(1952). Solubilities of Inorganic and
Organic Compounds. Van Nostrand.
3. Carbon disulfide in Linstrom,
Peter J.; Mallard, William G. (eds.);
NIST Chemistry WebBook, NIST
Standard Reference Database
Number 69, National Institute of
Standards and Technology,
Gaithersburg (MD),
http://webbook.nist.gov (retrieved
2014-05-27).
4. Sigma-Aldrich Co., Carbon disulfide .
Retrieved on 2014-05-27.
5. NIOSH Pocket Guide to Chemical
Hazards. "#0104" . National Institute
for Occupational Safety and Health
(NIOSH).
6. "Carbon disulfide" . Immediately
Dangerous to Life and Health
Concentrations (IDLH). National
Institute for Occupational Safety and
Health (NIOSH).
7. Holleman, Arnold Frederik; Wiberg,
Egon (2001), Wiberg, Nils (ed.),
Inorganic Chemistry, translated by
Eagleson, Mary; Brewer, William, San
Diego/Berlin: Academic Press/De
Gruyter, ISBN 0-12-352651-5.
8. "Carbon Disulfide report from IHS
Chemical" . Retrieved June 15, 2013.
 9. "Chemical profile: carbon disulfide
from ICIS.com" . Retrieved June 15,
2013.
10. "Carbon Disulfide" . Akzo Nobel.
11. Park, Tae-Jin; Banerjee, Sarbajit;
Hemraj-Benny, Tirandai; Wong,
Stanislaus S. (2006). "Purification
strategies and purity visualization
techniques for single-walled carbon
nanotubes" . Journal of Materials
Chemistry. 16 (2): 141–154.
doi:10.1039/b510858f .
12. "4,5-Dibenzoyl-1,3-dithiole-1-thione".
Org. Synth. 73: 270. 1996.
doi:10.15227/orgsyn.073.0270 .
13. Werner, Helmut (1982). "Novel
Coordination Compounds formed
from CS2 and Heteroallenes".
Coordination Chemistry Reviews. 43:
165–185. doi:10.1016/S0010-
8545(00)82095-0 .
14. Ochiai, Bungo; Endo, Takeshi (2005).
"Carbon dioxide and carbon disulfide
as resources for functional
polymers". Progress in Polymer
Science. 30 (2): 183–215.
doi:10.1016/j.progpolymsci.2005.0
1.005 .
15. Lay, Manchiu D. S.; Sauerhoff,
Mitchell W.; Saunders, Donald R.;
"Carbon Disulfide", in Ullmann's
Encyclopedia of Industrial Chemistry,
Wiley-VCH, Weinheim, 2000 doi:
10.1002/14356007.a05_185
16. Greenwood, Norman N.; Earnshaw,
Alan (1997). Chemistry of the
Elements (2nd ed.). Butterworth-
Heinemann. ISBN 978-0-08-037941-
8.
17. Worthing, Charles R.; Hance,
Raymond J. (1991). The Pesticide
Manual, A World Compendium (9th
ed.). British Crop Protection Council.
ISBN 9780948404429.
18. "ATSDR - Public Health Statement:
Carbon Disulfide" .
www.atsdr.cdc.gov. Retrieved
2020-01-17.
19. St. Clair, Kassia (2018). The Golden
Thread: How Fabric Changed
History. London: John Murray.
pp. 213–215. ISBN 978-1-4736-
5903-2. OCLC 1057250632 .
20. "Occupational health and safety –
chemical exposure" . www.sbu.se.
Swedish Agency for Health
Technology Assessment and
Assessment of Social Services
(SBU). Archived from the original on
2017-06-06. Retrieved 2017-06-07.
External links

Wikimedia Commons has media

related to Carbon disulfide.

Wikisource has the text of the 1911

Encyclopædia Britannica article
Carbon Bisulphide.

Australian National Pollutant Inventory:

Carbon disulfide
CDC - NIOSH Pocket Guide to
Chemical Hazards - Carbon Disulfide
Inno Motion Engineering
Agency for Toxic Substances &
Disease Registry Public Health
 Statement for Carbon Disulfide , 1996.
Resources on Carbon Disulfide by the
National Institute for Occupational
Safety and Health

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