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Sulfuryl chloride
 
 
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Sulfuryl chloride is SO2Cl2, a compound composed of sulfur
Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
, oxygen
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
, and chlorine
Chlorine

Chlorine...
. At room temperature, it is a colorless liquid with a pungent odor. Sulfuryl chloride is not found in nature, as can be inferred from its speedy hydrolysis.

Sulfuryl chloride is commonly confused with thionyl chloride
Thionyl chloride

Thionyl chloride is an inorganic compound with the chemical formula SulfurOxygenChlorine2. It is a reactive chemical reagent used in chlorination chemical reaction....
, SOCl2. The properties of these two sulfur oxychlorides are quite different: sulfuryl chloride is a source of chlorine
Chlorine

Chlorine...
 whereas thionyl chloride is a source of chloride
Chloride

The chloride ion is formed when the chemical element chlorine picks up one electron to form an anion Cl−....
 ions.

uryl chloride reacts violently with water, releasing hydrogen chloride
Hydrogen chloride

The Chemical compound hydrogen chloride has the chemical formula HydrogenChlorine. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric humidity....
 gas:

2 H2O
Water (molecule)

File:Blue-water-pool.jpgWater is the most abundant molecule on Earth's surface, constituting about 70% of the Earth's surface in liquid, solid, and gaseous states....
  + SO2Cl2 ? 2 HCl
Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
 + H2SO4
Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....


SO2Cl2 will also decompose
Decomposition

Decomposition refers to the process by which tissues of dead organisms break down into simpler forms of matter. Such a breakdown of dead organisms is essential for new growth and development of living organisms because it recycles the finite chemical constituents and frees up the limited physical space in the biome....
 when heated to or above 100 °C, about 30 ° above its boiling point.

Upon standing, SO2Cl2 decomposes to sulfur dioxide
Sulfur dioxide

Sulfur dioxide is the chemical compound with the formula SO2. It is produced by volcanoes and in various industrial processes. Since coal and petroleum often contain sulfur compounds, their combustion generates sulfur dioxide....
 and chlorine
Chlorine

Chlorine...
, which gives the older samples a slightly yellowish color.

ur is tetrahedral in SO2Cl2, being bound to two oxygen atoms via double bonds and to two chlorine atoms via single bonds.






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Sulfuryl chloride is SO2Cl2, a compound composed of sulfur
Sulfur

Sulfur or sulphur is the chemical element that has the atomic number 16. It is denoted with the symbol S. It is an abundant Valence non-metal....
, oxygen
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
, and chlorine
Chlorine

Chlorine...
. At room temperature, it is a colorless liquid with a pungent odor. Sulfuryl chloride is not found in nature, as can be inferred from its speedy hydrolysis.

Sulfuryl chloride is commonly confused with thionyl chloride
Thionyl chloride

Thionyl chloride is an inorganic compound with the chemical formula SulfurOxygenChlorine2. It is a reactive chemical reagent used in chlorination chemical reaction....
, SOCl2. The properties of these two sulfur oxychlorides are quite different: sulfuryl chloride is a source of chlorine
Chlorine

Chlorine...
 whereas thionyl chloride is a source of chloride
Chloride

The chloride ion is formed when the chemical element chlorine picks up one electron to form an anion Cl−....
 ions.

Properties

Sulfuryl chloride reacts violently with water, releasing hydrogen chloride
Hydrogen chloride

The Chemical compound hydrogen chloride has the chemical formula HydrogenChlorine. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric humidity....
 gas:

2 H2O
Water (molecule)

File:Blue-water-pool.jpgWater is the most abundant molecule on Earth's surface, constituting about 70% of the Earth's surface in liquid, solid, and gaseous states....
  + SO2Cl2 ? 2 HCl
Hydrochloric acid

Hydrochloric acid is the solution of hydrogen chloride in water. It is a highly corrosive, strong acid mineral acid and has major industrial uses....
 + H2SO4
Sulfuric acid

Sulfuric acid, hydrogen2sulfuroxygen4, is a strong mineral acid. It is soluble in water at all concentrations. Sulfuric acid has many applications, and is one of the top products of the chemical industry....


SO2Cl2 will also decompose
Decomposition

Decomposition refers to the process by which tissues of dead organisms break down into simpler forms of matter. Such a breakdown of dead organisms is essential for new growth and development of living organisms because it recycles the finite chemical constituents and frees up the limited physical space in the biome....
 when heated to or above 100 °C, about 30 ° above its boiling point.

Upon standing, SO2Cl2 decomposes to sulfur dioxide
Sulfur dioxide

Sulfur dioxide is the chemical compound with the formula SO2. It is produced by volcanoes and in various industrial processes. Since coal and petroleum often contain sulfur compounds, their combustion generates sulfur dioxide....
 and chlorine
Chlorine

Chlorine...
, which gives the older samples a slightly yellowish color.

Structure

Sulfur is tetrahedral in SO2Cl2, being bound to two oxygen atoms via double bonds and to two chlorine atoms via single bonds. The oxidation state
Oxidation number

The oxidation number of a central atom in a complex is the charge that it would have if all the ligands were removed along with the electron pairs that were shared with the central atom....
 of the sulfur atom is +6, as in H2SO4.

Synthesis of sulfuryl chloride

SO2Cl2 is prepared by the reaction of sulfur dioxide
Sulfur dioxide

Sulfur dioxide is the chemical compound with the formula SO2. It is produced by volcanoes and in various industrial processes. Since coal and petroleum often contain sulfur compounds, their combustion generates sulfur dioxide....
 and chlorine
Chlorine

Chlorine...
 in the presence of a catalyst, such as activated carbon
Activated carbon

Activated carbon, also called activated charcoal or activated coal, is a form of carbon that has been processed to make it extremely porous and thus to have a very large surface area available for adsorption or chemical reactions....
.
SO2
Sulfur dioxide

Sulfur dioxide is the chemical compound with the formula SO2. It is produced by volcanoes and in various industrial processes. Since coal and petroleum often contain sulfur compounds, their combustion generates sulfur dioxide....
  + Cl2
Chlorine

Chlorine...
  ? SO2Cl2
The crude product can be purified by fractional distillation
Fractional distillation

Fractional distillation is the separation of a mixture into its component parts, or fractions, such as in separating chemical compound by their boiling point by heating them to a temperature at which several fractions of the compound will evaporate....
. It is uncommon to prepare SO2Cl2 in the laboratory because it is supplied by many chemical companies, including FisherChemicals, AcrosOrganics, SFChem, Sigma-Aldrich.

Uses

Sulfuryl chloride is often used as source of Cl2. Because it is a pourable liquid, it is considered more convenient than Cl2 to measure, store, and dispense. SO2Cl2 is widely used as a reagent
Reagent

A reagent or reactant is a substance or compound consumed during a chemical reaction. Solvents and catalysts, although they are involved in the reaction, are usually not referred to as reactants....
 in the conversion of C-H --> C-Cl adjacent to activating substituents such as carbonyls and sulfoxides. It also chlorinates as alkane
Alkane

Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon and hydrogen , wherein these atoms are linked together exclusively by single bonds without any cyclic structure ....
s, alkene
Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
s, alkyne
Alkyne

Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms, with the formula CnH2n-2. The alkynes are traditionally known as acetylenes or the acetylene series, although the name acetylene is also used to refer specifically to the simplest member of the series, known as e...
s, aromatics, and epoxide
Epoxide

An epoxide is a cyclic ether with only three ring atoms. This ring approximately is an equilateral triangle which makes it highly ring strain....
s. Such reactions occur under free radical conditions using an initiator such as AIBN. SO2Cl2 can also convert alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
s to alkyl chlorides. In industry, sulfuryl chloride is most used in producing pesticides.

SO2Cl2 can also be used to treat wool to prevent shrinking.

Precautions

SO2Cl2 is toxic, corrosive, and acts as a lachrymator
Lachrymatory agent

A lachrymatory agent or lachrymator is a chemical compound that stimulates the corneal nerves in the eyes to cause tears, pain, and even temporary blindness....
. As described above, it can form explosive mixtures with water, as well as donor solvents such as DMSO
Dimethyl sulfoxide

Dimethyl sulfoxide is the chemical compound with the chemical formula 2SO. It was first synthesized in 1866 by the Russian scientist Alexander Saytzeff, who reported his findings in a German chemistry journal in 1867....
 and DMF
Dimethylformamide

Dimethylformamide is the organic compound with the chemical formula 2NCH. Commonly abbreviated DMF, this colourless liquid is miscible with Water and the majority of organic liquids....
.

Further reading


Lautens, M.; Bouchain, G. "[4+3] Cycloaddition in Water. endo,endo-Dimethyl-8-Oxabicyclo[8-Oxabicyclo[3.2.1]oct-6-en-3-one" Organic Syntheses, ; Vol. 79, p.251 (2002) (Coll. Vol. 10, p.336 (2004)). a-Chlorination of 3-pentanone.