Difference between revisions of "Carbon disulfide"

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{{Chembox
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| Name = Carbon disulfide
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| Reference =
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| IUPACName = Methanedithione
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| PIN =
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| SystematicName =
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| OtherNames = Carbon bisulfide<br>Carbon disulphide<br>Dithiocarbonic anhydride
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<!-- Images -->
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| ImageFile = Carbon disulfide syringe sample and original bottle by Thoisoi2.png
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| ImageSize = 280
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| ImageCaption = Sample of carbon disulfide in a syringe
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| Section1 = {{Chembox Identifiers
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| 3DMet =
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| Abbreviations =
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| SMILES =
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  }}
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| Section2 = {{Chembox Properties
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| AtmosphericOHRateConstant =
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| Appearance = Colorless liquid
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| BoilingPt =
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| BoilingPtC = 46.24
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| BoilingPt_ref =
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| BoilingPt_notes =
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| Density = 1.539 g/cm<sup>3</sup> (-186°C)<br>1.2927 g/cm<sup>3</sup> (0 °C)<br>1.266 g/cm<sup>3</sup> (25 °C)
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| Formula = CS<sub>2</sub>
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| HenryConstant =
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| LogP =
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| MolarMass = 76.13 g/mol
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| MeltingPt =
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| MeltingPtC = -111.61
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| MeltingPt_ref =
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| MeltingPt_notes =
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| Odor = Chloroform-like (pure)<br>Foul, rotten eggs-like (technical grade)
 +
| pKa =
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| pKb =
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| Solubility = 0.258 g/100 ml (0 °C)<br>0.239 g/100 ml (10 °C)<br>0.217 g/100 ml (20 °C)
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| SolubleOther = Miscible with [[acetone]], [[benzene]], [[carbon tetrachloride|CCl<sub>4</sub>]], [[chloroform]], [[dichloromethane]], [[diethyl ether]], [[ethanol]], [[ethyl acetate]], [[mineral oil]], [[toluene]], [[xylene]]<br>Soluble in [[Dimethyl sulfoxide|DMSO]]<br>Slightly soluble in [[acetic acid]], [[formic acid]]
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| Solubility1 = 4.66 g/100 g
 +
| Solvent1 = formic acid
 +
| Solubility2 = 45 g/100 g (20.3 °C)
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| Solvent2 = dimethyl sulfoxide
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| VaporPressure = 48.1 kPa (25 °C)<br>82.4 kPa (40 °C)
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  }}
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| Section3 = {{Chembox Structure
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| Coordination =
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| CrystalStruct =
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| MolShape = Linear
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| Section4 = {{Chembox Thermochemistry
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| DeltaGf = 64.4 kJ/mol
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| DeltaHc = 1687.2 kJ/mol
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| DeltaHf = 88.7 kJ/mol
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| Entropy = 151 J·mol<sup>-1</sup>·K<sup>-1</sup>
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| HeatCapacity = 75.73 J·mol<sup>-1</sup>·K<sup>-1</sup>
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  }}
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| Section5 = {{Chembox Explosive
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| ShockSens =
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| FrictionSens =
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| DetonationV =
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| REFactor =
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| Section6 = {{Chembox Hazards
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| AutoignitionPt = 102 °C (216 °F; 375 K)
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| ExploLimits = 1.3%-50%
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| ExternalMSDS = [https://www.docdroid.net/AWq5j26/carbon-disulfide-sa.pdf.html Sigma-Aldrich]
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| FlashPt = −43 °C (−45 °F; 230 K)
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| LD50 = 3188 mg/kg (rat, oral)
 +
| LC50 = >1670 ppm (rat, 1 hr)<br>15500 ppm (rat, 1 hr)<br>3000 ppm (rat, 4 hr)<br>3500 ppm (rat, 4 hr)<br>7911 ppm (rat, 2 hr)<br>3165 ppm (mouse, 2 hr)
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| MainHazards = Extremely flammable
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| Section7 = {{Chembox Related
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| OtherAnions =
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| OtherCations =
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| OtherFunction =
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| OtherFunction_label =
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| OtherCompounds = [[Carbon dioxide]]<br>[[Hydrogen sulfide]]
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  }}
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}}
 
'''Carbon disulfide''' is a colorless volatile liquid with the formula '''CS<sub>2</sub>''', useful as a non-polar solvent.
 
'''Carbon disulfide''' is a colorless volatile liquid with the formula '''CS<sub>2</sub>''', useful as a non-polar solvent.
  
 
==Properties==
 
==Properties==
 
===Chemical===
 
===Chemical===
−
Chlorination of CS<sub>2</sub> yields [[carbon tetrachloride]] and sulfur dichloride:
+
Carbon disulfide is highly flammable and will burn in air to release [[carbon dioxide|carbon]] and [[sulfur dioxide]]s.
 +
 
 +
:CS<sub>2</sub> + 3 O<sub>2</sub> → CO<sub>2</sub> + 2 SO<sub>2</sub>
 +
 
 +
Chlorination of CS<sub>2</sub> yields [[carbon tetrachloride]] and [[sulfur dichloride]]:
 +
 
 
:CS<sub>2</sub> + 3 Cl<sub>2</sub> → CCl<sub>4</sub> + S<sub>2</sub>Cl<sub>2</sub>
 
:CS<sub>2</sub> + 3 Cl<sub>2</sub> → CCl<sub>4</sub> + S<sub>2</sub>Cl<sub>2</sub>
 +
 +
When sulfur is dissolved in carbon disulfide, it will react with copper metal at room temperature, forming copper sulfide.<ref>https://www.youtube.com/watch?v=UrUqPIFep1s</ref>
 +
 +
Carbon disulfide will react with aq. alkali bases to form dithiocarbonates:
 +
 +
: CS<sub>2</sub> + 2 NaOH<sub>(aq)</sub> → Na<sub>2</sub>COS<sub>2</sub> + H<sub>2</sub>O
  
 
===Physical===
 
===Physical===
−
Carbon disulfide is a colorless, with an chloroform like smell when pure. Impure CS<sub>2</sub> has a yellowish color and has a putrid smell. It is insoluble in water, but soluble in many organic solvents, such as [[benzene]], [[ethanol]], [[diethyl ether]], [[carbon tetrachloride]], [[chloroform]]. It's poorly soluble in [[formic acid]]. CS<sub>2</sub> boils at 46.24 °C and freezes at −111.61 °C. It has a low autoignition temperature for a solvent, of only 102 °C.
+
Carbon disulfide is a colorless liquid, with an chloroform like smell when pure. Impure CS<sub>2</sub> has a yellowish color and has a putrid smell. It is insoluble in water, but soluble in many organic solvents, such as [[benzene]], [[ethanol]], [[diethyl ether]], [[carbon tetrachloride]], [[chloroform]]. It's poorly soluble in [[formic acid]]. CS<sub>2</sub> boils at 46.24 °C and freezes at −111.61 °C. It has a low autoignition temperature for a solvent, of only 102 °C.
  
 
==Availability==
 
==Availability==
−
Carbon disulfide is sold by chemical suppliers, however there appears to be no sellers on Ebay or Amazon.
+
Carbon disulfide is sold by chemical suppliers, however there appears to be no sellers on eBay or Amazon. It was used as insecticide years ago, but its use has fallen out.
 +
 
 +
Carbon disulfide is very difficult to find in most parts of the world.
  
 
==Preparation==
 
==Preparation==
−
There are many ways to synthesize CS<sub>2</sub>, most if not all tend to produce plenty of side products, which means that the product will be impure and have a bad smell. Some processes have low yield.
+
There are many ways to synthesize CS<sub>2</sub>, most if not all tend to produce plenty of side products, with most synthesis routes producing [[hydrogen sulfide]] as the main side product. Some processes have low yield.
  
 
The first method, involves the reaction of [[sulfur]] vapors with carbon (or coke, anthracite, or any other coal) at 900°C. The resulting vapors are condensed and sulfur disulfide is purified. BromicAcid managed to synthesize only a few ml using this method. A few years later, garagechemist in collaboration with Len1, tried to improve the said method, using a tube furnace. It yielded around 44 g of CS<sub>2</sub>. myst32YT mas also made a small amount of carbon disulfide.<ref>https://www.youtube.com/watch?v=IkBFlPagRgA</ref>
 
The first method, involves the reaction of [[sulfur]] vapors with carbon (or coke, anthracite, or any other coal) at 900°C. The resulting vapors are condensed and sulfur disulfide is purified. BromicAcid managed to synthesize only a few ml using this method. A few years later, garagechemist in collaboration with Len1, tried to improve the said method, using a tube furnace. It yielded around 44 g of CS<sub>2</sub>. myst32YT mas also made a small amount of carbon disulfide.<ref>https://www.youtube.com/watch?v=IkBFlPagRgA</ref>
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Another method involves the reaction of [[carbon tetrachloride]] with sulfur, between 120-220 °C, in the presence of a catalyst such as copper chloride, iron chloride, [[aluminium chloride]].<ref>Fomin, W. A., Zhurnal Obshchei Khimii, 1936, Vol. 6, p. 852 - 854</ref>
 
Another method involves the reaction of [[carbon tetrachloride]] with sulfur, between 120-220 °C, in the presence of a catalyst such as copper chloride, iron chloride, [[aluminium chloride]].<ref>Fomin, W. A., Zhurnal Obshchei Khimii, 1936, Vol. 6, p. 852 - 854</ref>
  
−
The thermal decomposition of [[ammonium thiocyanate]] yields carbon disulfide, [[ammonia]], hydrogen sulfide, leaving a residue of guanidinium thiocyanate. This reaction produces a fairly pure compound. Other thiocyanates can also be used.
+
The thermal decomposition of [[ammonium thiocyanate]], preferably in an inert atmosphere yields carbon disulfide, [[ammonia]], hydrogen sulfide, leaving a residue of guanidinium thiocyanate. This reaction produces a fairly pure compound, though the starting products are not particularly cheap. Other thiocyanates can also be used. An approximate reaction of the decomposition is shown below:
 +
 
 +
: NH<sub>4</sub>SCN → CS<sub>2</sub> + NH<sub>3</sub> + H<sub>2</sub>S + CH<sub>6</sub>N<sub>3</sub>SCN
  
 
Reacting sulfur or sulfur dioxide vapors with [[carbon dioxide]] at 800 °C in the presence of alumina catalyst will also yield carbon disulfide. Carbonyl sulfide may also form as a side product.<ref>http://onlinelibrary.wiley.com/doi/10.1002/ange.19310442003/abstract</ref><ref>http://onlinelibrary.wiley.com/doi/10.1002/ange.19320455202/abstract</ref>
 
Reacting sulfur or sulfur dioxide vapors with [[carbon dioxide]] at 800 °C in the presence of alumina catalyst will also yield carbon disulfide. Carbonyl sulfide may also form as a side product.<ref>http://onlinelibrary.wiley.com/doi/10.1002/ange.19310442003/abstract</ref><ref>http://onlinelibrary.wiley.com/doi/10.1002/ange.19320455202/abstract</ref>
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Carbon disulfide can also be obtained in traces by reacting [[benzene]] with [[sulfur dioxide]], at 500°C. It also produces many byproducts,such as dithiobenzene, carbon dioxide, carbonyl sulfide, some free oxygen, and some unknown polymeric residue.<ref>http://pubs.acs.org/doi/abs/10.1021/ja01510a062</ref> The reaction can be improved by using a [[vanadium pentoxide]]/alumina catalyst, the reaction taking place at 1000-1200 °C.<ref>http://pubs.rsc.org/en/content/articlelanding/1957/tf/tf9575300972#!divAbstract</ref>
 
Carbon disulfide can also be obtained in traces by reacting [[benzene]] with [[sulfur dioxide]], at 500°C. It also produces many byproducts,such as dithiobenzene, carbon dioxide, carbonyl sulfide, some free oxygen, and some unknown polymeric residue.<ref>http://pubs.acs.org/doi/abs/10.1021/ja01510a062</ref> The reaction can be improved by using a [[vanadium pentoxide]]/alumina catalyst, the reaction taking place at 1000-1200 °C.<ref>http://pubs.rsc.org/en/content/articlelanding/1957/tf/tf9575300972#!divAbstract</ref>
  
−
Pyrolysis or scrap types also gives carbon disulfide, although separating it from the mixture is not very practical.<ref>http://pubs.acs.org/doi/abs/10.1021/es990883y</ref>
+
Pyrolysis of scrap tires also gives carbon disulfide, although separating it from the mixture is not very practical.<ref>http://pubs.acs.org/doi/abs/10.1021/es990883y</ref>
  
 
==Projects==
 
==Projects==
 
*Sulfur extraction and purification
 
*Sulfur extraction and purification
 +
*[[Barking dog reaction]]
 
*Make [[carbon tetrachloride]]
 
*Make [[carbon tetrachloride]]
−
*Make [[sulfur disulfide]]
 
 
*Make [[KS Fluid]]
 
*Make [[KS Fluid]]
 +
*Solvent for synthesis of [[phosphorus triiodide]]
 +
*Synthesize trithiocarbonates
 +
*Prepare xanthate salts
  
 
==Handling==
 
==Handling==
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===Storage===
 
===Storage===
−
Carbon disulfide should be stored in closed bottles away from any heat source. Due to it's high volatility its best kept in a cold place. The bottle should be open periodically to prevent a pressure build-up.
+
Carbon disulfide should be stored in closed bottles away from any heat and light sources. Due to it's high volatility its best kept in a cold place. The bottle should be open periodically to prevent a pressure build-up.
  
 
===Disposal===
 
===Disposal===
−
Carbon disulfide can be burned, although this will produce sulfur dioxide gas.
+
Carbon disulfide can be burned, although this will produce toxic sulfur dioxide gas.
  
 
==References==
 
==References==
Line 60: Line 191:
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=1066 Carbon Disulfide Preparation]
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=1066 Carbon Disulfide Preparation]
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=10564 Carbon Disulfide from sulfur and charcoal]
 
*[http://www.sciencemadness.org/talk/viewthread.php?tid=10564 Carbon Disulfide from sulfur and charcoal]
 +
*[https://www.sciencemadness.org/whisper/viewthread.php?tid=66204 Fun/cool reactions/experiments to do with CS2?]
 +
*[https://www.sciencemadness.org/whisper/viewthread.php?tid=147199 Carbon disulfide synthesis (alternative routes)]
  
 
[[Category:Chemical compounds]]
 
[[Category:Chemical compounds]]
 
[[Category:Inorganic compounds]]
 
[[Category:Inorganic compounds]]
 
[[Category:Carbon compounds]]
 
[[Category:Carbon compounds]]
 +
[[Category:Sulfur compounds]]
 
[[Category:Sulfides]]
 
[[Category:Sulfides]]
 
[[Category:Solvents]]
 
[[Category:Solvents]]
 
[[Category:Nonpolar solvents]]
 
[[Category:Nonpolar solvents]]
 
[[Category:Volatile chemicals]]
 
[[Category:Volatile chemicals]]
 +
[[Category:Liquids]]

Latest revision as of 21:40, 16 October 2022

Carbon disulfide
Carbon disulfide syringe sample and original bottle by Thoisoi2.png
Sample of carbon disulfide in a syringe
Names
IUPAC name
Methanedithione
Other names
Carbon bisulfide
Carbon disulphide
Dithiocarbonic anhydride
Properties
CS2
Molar mass 76.13 g/mol
Appearance Colorless liquid
Odor Chloroform-like (pure)
Foul, rotten eggs-like (technical grade)
Density 1.539 g/cm3 (-186°C)
1.2927 g/cm3 (0 °C)
1.266 g/cm3 (25 °C)
Melting point −111.61 °C (−168.90 °F; 161.54 K)
Boiling point 46.24 °C (115.23 °F; 319.39 K)
0.258 g/100 ml (0 °C)
0.239 g/100 ml (10 °C)
0.217 g/100 ml (20 °C)
Solubility Miscible with acetone, benzene, CCl4, chloroform, dichloromethane, diethyl ether, ethanol, ethyl acetate, mineral oil, toluene, xylene
Soluble in DMSO
Slightly soluble in acetic acid, formic acid
Solubility in formic acid 4.66 g/100 g
Solubility in dimethyl sulfoxide 45 g/100 g (20.3 °C)
Vapor pressure 48.1 kPa (25 °C)
82.4 kPa (40 °C)
Thermochemistry
151 J·mol-1·K-1
88.7 kJ/mol
Hazards
Safety data sheet Sigma-Aldrich
Flash point −43 °C (−45 °F; 230 K)
Lethal dose or concentration (LD, LC):
3188 mg/kg (rat, oral)
>1670 ppm (rat, 1 hr)
15500 ppm (rat, 1 hr)
3000 ppm (rat, 4 hr)
3500 ppm (rat, 4 hr)
7911 ppm (rat, 2 hr)
3165 ppm (mouse, 2 hr)
Related compounds
Related compounds
 Carbon dioxide
Hydrogen sulfide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Carbon disulfide is a colorless volatile liquid with the formula CS2, useful as a non-polar solvent.

Properties

Chemical

Carbon disulfide is highly flammable and will burn in air to release carbon and sulfur dioxides.

CS2 + 3 O2 → CO2 + 2 SO2

Chlorination of CS2 yields carbon tetrachloride and sulfur dichloride:

CS2 + 3 Cl2 → CCl4 + S2Cl2

When sulfur is dissolved in carbon disulfide, it will react with copper metal at room temperature, forming copper sulfide.[1]

Carbon disulfide will react with aq. alkali bases to form dithiocarbonates:

CS2 + 2 NaOH(aq) → Na2COS2 + H2O

Physical

Carbon disulfide is a colorless liquid, with an chloroform like smell when pure. Impure CS2 has a yellowish color and has a putrid smell. It is insoluble in water, but soluble in many organic solvents, such as benzene, ethanol, diethyl ether, carbon tetrachloride, chloroform. It's poorly soluble in formic acid. CS2 boils at 46.24 °C and freezes at −111.61 °C. It has a low autoignition temperature for a solvent, of only 102 °C.

Availability

Carbon disulfide is sold by chemical suppliers, however there appears to be no sellers on eBay or Amazon. It was used as insecticide years ago, but its use has fallen out.

Carbon disulfide is very difficult to find in most parts of the world.

Preparation

There are many ways to synthesize CS2, most if not all tend to produce plenty of side products, with most synthesis routes producing hydrogen sulfide as the main side product. Some processes have low yield.

The first method, involves the reaction of sulfur vapors with carbon (or coke, anthracite, or any other coal) at 900°C. The resulting vapors are condensed and sulfur disulfide is purified. BromicAcid managed to synthesize only a few ml using this method. A few years later, garagechemist in collaboration with Len1, tried to improve the said method, using a tube furnace. It yielded around 44 g of CS2. myst32YT mas also made a small amount of carbon disulfide.[2]

Another method, that works at lower temperatures (600 °C), utilizes methane as the carbon source in the presence of silica gel or alumina catalysts:

2 CH4 + S8 → 2 CS2 + 4 H2S[3]

Another method involves the reaction of carbon tetrachloride with sulfur, between 120-220 °C, in the presence of a catalyst such as copper chloride, iron chloride, aluminium chloride.[4]

The thermal decomposition of ammonium thiocyanate, preferably in an inert atmosphere yields carbon disulfide, ammonia, hydrogen sulfide, leaving a residue of guanidinium thiocyanate. This reaction produces a fairly pure compound, though the starting products are not particularly cheap. Other thiocyanates can also be used. An approximate reaction of the decomposition is shown below:

NH4SCN → CS2 + NH3 + H2S + CH6N3SCN

Reacting sulfur or sulfur dioxide vapors with carbon dioxide at 800 °C in the presence of alumina catalyst will also yield carbon disulfide. Carbonyl sulfide may also form as a side product.[5][6]

A mixture of acetylene and sulfur vapor at temperatures between 325-650 °C will also yield carbon disulfide. Pyrite can also be used instead of sulfur.[7]

A different way involves the reaction of carbon monoxide with sulfur, in the presence of a catalyst such as iron, iron(III) sulfide, at temperatures between 400 - 500 °C.[8] The same reaction can also be carried out at 500 °C in the presence of silica gel.[9]

The reaction of calcium carbide with sulfur at at 500 °C.[10] The same reaction can also occur at temperatures between 250 - 360 °C, with a different yield.[11]

Another method described in literature is the reaction of lead(II) sulfide with carbon monoxide, in a furnace, at high temperature.[12]

Carbon disulfide can also be obtained in traces by reacting benzene with sulfur dioxide, at 500°C. It also produces many byproducts,such as dithiobenzene, carbon dioxide, carbonyl sulfide, some free oxygen, and some unknown polymeric residue.[13] The reaction can be improved by using a vanadium pentoxide/alumina catalyst, the reaction taking place at 1000-1200 °C.[14]

Pyrolysis of scrap tires also gives carbon disulfide, although separating it from the mixture is not very practical.[15]

Projects

Handling

Safety

Carbon disulfide has moderate toxicity. It is an irritant to the eyes and skin. CS2 is however extremely volatile and flammable.[16]

Storage

Carbon disulfide should be stored in closed bottles away from any heat and light sources. Due to it's high volatility its best kept in a cold place. The bottle should be open periodically to prevent a pressure build-up.

Disposal

Carbon disulfide can be burned, although this will produce toxic sulfur dioxide gas.

References

  1. ↑ https://www.youtube.com/watch?v=UrUqPIFep1s
  2. ↑ https://www.youtube.com/watch?v=IkBFlPagRgA
  3. ↑ http://pubs.acs.org/doi/abs/10.1021/ie50642a007
  4. ↑ Fomin, W. A., Zhurnal Obshchei Khimii, 1936, Vol. 6, p. 852 - 854
  5. ↑ http://onlinelibrary.wiley.com/doi/10.1002/ange.19310442003/abstract
  6. ↑ http://onlinelibrary.wiley.com/doi/10.1002/ange.19320455202/abstract
  7. ↑ Bulletin de la Societe Chimique de France, 1908, Vol. <4> 3, p. 151
  8. ↑ DE398322 C
  9. ↑ http://pubs.acs.org/doi/abs/10.1021/ie50584a043
  10. ↑ http://onlinelibrary.wiley.com/doi/10.1002/ange.19280412607/abstract
  11. ↑ Moissan, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences (1894), Vol. 118, p. 502
  12. ↑ http://pubs.rsc.org/en/content/articlelanding/1863/js/js8631600042#!divAbstract
  13. ↑ http://pubs.acs.org/doi/abs/10.1021/ja01510a062
  14. ↑ http://pubs.rsc.org/en/content/articlelanding/1957/tf/tf9575300972#!divAbstract
  15. ↑ http://pubs.acs.org/doi/abs/10.1021/es990883y
  16. ↑ http://www.sciencelab.com/msds.php?msdsId=9927125

Relevant Sciencemadness threads

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