Carbon disulfide

Carbon disulfide

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Carbon disulfide is a colorless volatile
Volatility (chemistry)
In chemistry and physics, volatility is the tendency of a substance to vaporize. Volatility is directly related to a substance's vapor pressure. At a given temperature, a substance with higher vapor pressure vaporizes more readily than a substance with a lower vapor pressure.The term is primarily...

 liquid
Liquid
Liquid is one of the three classical states of matter . Like a gas, a liquid is able to flow and take the shape of a container. Some liquids resist compression, while others can be compressed. Unlike a gas, a liquid does not disperse to fill every space of a container, and maintains a fairly...

 with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 CS2. The compound is used frequently as a building block in organic chemistry
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...

 as well as an industrial and chemical non-polar solvent
Solvent
A solvent is a liquid, solid, or gas that dissolves another solid, liquid, or gaseous solute, resulting in a solution that is soluble in a certain volume of solvent at a specified temperature...

. It has an "ether
Diethyl ether
Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...

-like" odor, but commercial samples are typically contaminated with foul-smelling impurities, such as carbonyl sulfide
Carbonyl sulfide
Carbonyl sulfide is the chemical compound with the formula OCS. Commonly written as COS, it is a colourless flammable gas with an unpleasant odor. It is a linear molecule consisting of a carbonyl group double bonded to a sulfur atom...

.

Occurrence and manufacture


Small amounts of carbon disulfide are released by volcanic
Volcano
2. Bedrock3. Conduit 4. Base5. Sill6. Dike7. Layers of ash emitted by the volcano8. Flank| 9. Layers of lava emitted by the volcano10. Throat11. Parasitic cone12. Lava flow13. Vent14. Crater15...

 eruptions and marsh
Marsh
In geography, a marsh, or morass, is a type of wetland that is subject to frequent or continuous flood. Typically the water is shallow and features grasses, rushes, reeds, typhas, sedges, other herbaceous plants, and moss....

es. CS2 once was manufactured by combining carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 (or coke
Coke (fuel)
Coke is the solid carbonaceous material derived from destructive distillation of low-ash, low-sulfur bituminous coal. Cokes from coal are grey, hard, and porous. While coke can be formed naturally, the commonly used form is man-made.- History :...

) and sulfur
Sulfur
Sulfur or sulphur is the chemical element with atomic number 16. In the periodic table it is represented by the symbol S. It is an abundant, multivalent non-metal. Under normal conditions, sulfur atoms form cyclic octatomic molecules with chemical formula S8. Elemental sulfur is a bright yellow...

 at high temperatures. A lower temperature reaction, requiring only 600 °C utilizes natural gas
Natural gas
Natural gas is a naturally occurring gas mixture consisting primarily of methane, typically with 0–20% higher hydrocarbons . It is found associated with other hydrocarbon fuel, in coal beds, as methane clathrates, and is an important fuel source and a major feedstock for fertilizers.Most natural...

 as the carbon source in the presence of silica gel
Silica gel
Silica gel is a granular, vitreous, porous form of silica made synthetically from sodium silicate. Despite its name, silica gel is a solid. It is a naturally occurring mineral that is purified and processed into either granular or beaded form...

 or alumina catalysts:
2CH4 + S8 → 2CS2 + 4H2S

The reaction is analogous to the combustion of methane. Although it is isoelectronic with carbon dioxide
Carbon dioxide
Carbon dioxide is a naturally occurring chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom...

, CS2 is highly flammable:
CS2 + 3O2 → CO2 + 2SO2
Sulfur dioxide
Sulfur dioxide is the chemical compound with the formula . It is released by volcanoes and in various industrial processes. Since coal and petroleum often contain sulfur compounds, their combustion generates sulfur dioxide unless the sulfur compounds are removed before burning the fuel...


Reactions


Compared to CO2, CS2 is more reactive toward nucleophile
Nucleophile
A nucleophile is a species that donates an electron-pair to an electrophile to form a chemical bond in a reaction. All molecules or ions with a free pair of electrons can act as nucleophiles. Because nucleophiles donate electrons, they are by definition Lewis bases.Nucleophilic describes the...

s 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
Metham sodium
Metham sodium is a soil fumigant used as a pesticide, herbicide, and fungicide. It is one of the most widely used pesticides in the United States, with approximately 60 million pounds used in 2001...

, a soil fumigant and is commonly used in the production of the soft fabric viscose
Viscose
Viscose is a viscous organic liquid used to make rayon and cellophane. Viscose is becoming synonymous with rayon, a soft material commonly used in shirts, shorts, coats, jackets, and other outer wear.-Manufacture:...

.

Addition of nucleophiles


Nucleophiles such as amines afford dithiocarbamate
Sodium diethyldithiocarbamate
Sodium diethyldithiocarbamate is the organosulfur compound with the formula NaS2CN2.-Preparation:This salt is obtained by treating carbon disulfide with diethylamine in the presence of sodium hydroxide:Other dithiocarbamates can be prepared similarly from secondary amines and carbon disulfide...

s:
2R2NH + CS2 → [R2NH2+][R2NCS2]


Xanthate
Xanthate
Xanthate usually refers to a salt with the formula ROCS2-M+ . The name xanthates is derived from Greek ξανθός , meaning “yellowish, golden”, and indeed most xanthate salts are yellow...

s form similarly from alkoxide
Alkoxide
An alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They can be written as RO−, where R is the organic substituent. Alkoxides are strong bases and, when R is not bulky, good nucleophiles and good ligands...

s:
RONa + CS2 → [Na+][ROCS2]


This reaction is the basis of the manufacture of regenerated cellulose
Cellulose
Cellulose is an organic compound with the formula , a polysaccharide consisting of a linear chain of several hundred to over ten thousand β linked D-glucose units....

, the main ingredient of viscose
Viscose
Viscose is a viscous organic liquid used to make rayon and cellophane. Viscose is becoming synonymous with rayon, a soft material commonly used in shirts, shorts, coats, jackets, and other outer wear.-Manufacture:...

, rayon
Rayon
Rayon is a manufactured regenerated cellulose fiber. Because it is produced from naturally occurring polymers, it is neither a truly synthetic fiber nor a natural fiber; it is a semi-synthetic or artificial fiber. Rayon is known by the names viscose rayon and art silk in the textile industry...

 and cellophane
Cellophane
Cellophane is a thin, transparent sheet made of regenerated cellulose. Its low permeability to air, oils, greases, bacteria and water makes it useful for food packaging...

. 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
Carbon tetrachloride
Carbon tetrachloride, also known by many other names is the organic compound with the formula CCl4. It was formerly widely used in fire extinguishers, as a precursor to refrigerants, and as a cleaning agent...

:
CS2 + 3Cl2
Chlorine
Chlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine...

 → CCl4 + S2Cl2
Disulfur dichloride
Disulfur dichloride is the chemical compound with the formula S2Cl2 . Some alternative names for this compound are sulfur monochloride , disulphur dichloride and sulphur monochloride...


This conversion proceeds via the intermediacy of thiophosgene
Thiophosgene
Thiophosgene is a red liquid with the formula CSCl2. It is a molecule with trigonal planar geometry. There are two reactive C–Cl bonds that allow it to be used in diverse organic syntheses.-Synthesis of CSCl2:...

, CSCl2.

Coordination chemistry


CS2 is a ligand for many metal complexes, forming pi complexes. One example is CpCo(η2
Hapticity
The term hapticity is used to describe how a group of contiguous atoms of a ligand are coordinated to a central atom. Hapticity of a ligand is indicated by the Greek character 'eta', η. A superscripted number following the η denotes the number of contiguous atoms of the ligand that are bound to...

-CS2)(PMe3).

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
Johnson Matthey
Johnson Matthey plc is multinational chemicals and precious metals company headquartered in London, United Kingdom.It is listed on the London Stock Exchange and is a constituent of the FTSE 100 Index.-History:...

's sister company Alfa Aesar
Alfa Aesar
Alfa Aesar, headquartered in Ward Hill, Massachusetts, is a supplier of reagents and materials for use in research and development, and analysis. They have facilities in many countries and manufacture many of the chemicals they sell...

 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.

Fumigation


Used for fumigation
Fumigation
Fumigation is a method of pest control that completely fills an area with gaseous pesticides—or fumigants—to suffocate or poison the pests within. It is utilized for control of pests in buildings , soil, grain, and produce, and is also used during processing of goods to be imported or...

 in airtight storage warehouses, airtight flat storages, bins, grain elevators, railroad box cars, shipholds, barges and cereal mills.

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.

Solvent


Carbon disulfide is a solvent for phosphorus
Phosphorus
Phosphorus is the chemical element that has the symbol P and atomic number 15. A multivalent nonmetal of the nitrogen group, phosphorus as a mineral is almost always present in its maximally oxidized state, as inorganic phosphate rocks...

, sulfur, selenium
Selenium
Selenium is a chemical element with atomic number 34, chemical symbol Se, and an atomic mass of 78.96. It is a nonmetal, whose properties are intermediate between those of adjacent chalcogen elements sulfur and tellurium...

, bromine
Bromine
Bromine ") is a chemical element with the symbol Br, an atomic number of 35, and an atomic mass of 79.904. It is in the halogen element group. The element was isolated independently by two chemists, Carl Jacob Löwig and Antoine Jerome Balard, in 1825–1826...

, iodine
Iodine
Iodine is a chemical element with the symbol I and atomic number 53. The name is pronounced , , or . The name is from the , meaning violet or purple, due to the color of elemental iodine vapor....

, fats
Fat
Fats consist of a wide group of compounds that are generally soluble in organic solvents and generally insoluble in water. Chemically, fats are triglycerides, triesters of glycerol and any of several fatty acids. Fats may be either solid or liquid at room temperature, depending on their structure...

, resins
Resin
Resin in the most specific use of the term is a hydrocarbon secretion of many plants, particularly coniferous trees. Resins are valued for their chemical properties and associated uses, such as the production of varnishes, adhesives, and food glazing agents; as an important source of raw materials...

, and rubber
Rubber
Natural rubber, also called India rubber or caoutchouc, is an elastomer that was originally derived from latex, a milky colloid produced by some plants. The plants would be ‘tapped’, that is, an incision made into the bark of the tree and the sticky, milk colored latex sap collected and refined...

. It has been used in the purification of single-walled carbon nanotubes.

Manufacturing


The principal industrial uses of carbon disulfide are the manufacture of viscose rayon, cellophane
Cellophane
Cellophane is a thin, transparent sheet made of regenerated cellulose. Its low permeability to air, oils, greases, bacteria and water makes it useful for food packaging...

 film, carbon tetrachloride
Carbon tetrachloride
Carbon tetrachloride, also known by many other names is the organic compound with the formula CCl4. It was formerly widely used in fire extinguishers, as a precursor to refrigerants, and as a cleaning agent...

 and xanthogenates and electronic vacuum tube
Vacuum tube
In electronics, a vacuum tube, electron tube , or thermionic valve , reduced to simply "tube" or "valve" in everyday parlance, is a device that relies on the flow of electric current through a vacuum...

. It is also used in the manufacture of Bamboo Fiber.

Health effects


At high levels, carbon disulfide may be life-threatening because it affects the nervous system
Nervous system
The nervous system is an organ system containing a network of specialized cells called neurons that coordinate the actions of an animal and transmit signals between different parts of its body. In most animals the nervous system consists of two parts, central and peripheral. The central nervous...

. Significant safety data comes from the viscose rayon industry, where both carbon disulfide as well as small amounts of H2S
Hydrogen sulfide
Hydrogen sulfide is the chemical compound with the formula . It is a colorless, very poisonous, flammable gas with the characteristic foul odor of expired eggs perceptible at concentrations as low as 0.00047 parts per million...

may be present.

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