Thionyl chloride

	Email		Print
	Bookmark		Link

Thionyl chloride

Thionyl chloride (or thionyl dichloride) is an inorganic compound

Inorganic compound

Traditionally, inorganic compounds are considered to be of a mineral, not biological, origin. Complementarily, most organic compounds are traditionally viewed as being of biological origin....
with the formula

Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
S

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....
O

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]]...
Cl

Chlorine

Chlorine...
₂. It is a reactive chemical 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....
used in chlorination reactions

Chemical reaction

A chemical reaction is a process that always results in the interconversion of chemical substances. The substance or substances initially involved in a chemical reaction are called reactants....
. It is a colorless, distillable liquid

Liquid

Liquid is one of the principal states of matter. A liquid is a fluid that has the particles loose and can freely form a distinct surface at the boundaries of its bulk material....
at room temperature

Temperature

In physics, temperature is a physical property of a Physical system that underlies the common notions of hot and cold; something that feels hotter generally has the greater temperature....
and pressure

Pressure

Pressure is the force per unit area applied to an object in a direction surface normal to the surface. Gauge pressure is the pressure relative to the local atmospheric or ambient pressure....
that decomposes above 140 °C. Thionyl chloride is sometimes confused with sulfuryl chloride

Sulfuryl chloride

Sulfuryl chloride is SO2Cl2, a compound composed of sulfur, oxygen, and chlorine. At room temperature, it is a colorless liquid with a pungent odor....
, SO₂Cl₂, but the chemical properties of these S(IV) and S(VI) compounds differ significantly.

Discussion

Ask a question about 'Thionyl chloride'

Start a new discussion about 'Thionyl chloride'

Answer questions from other users

Full Discussion Forum

Encyclopedia

Thionyl chloride (or thionyl dichloride) is an inorganic compound

Inorganic compound

Chemical formula

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....
O

Oxygen

Chlorine

Chlorine...
₂. It is a reactive chemical reagent

Reagent

Chemical reaction

Liquid

Temperature

Pressure

Sulfuryl chloride

Properties and structure

The molecule SOCl₂ is pyramidal, indicating the presence of a lone pair of electrons on the S(IV) center (in contrast, the stoichiometrically related species COCl₂

Phosgene

Phosgene is the chemical compound with the chemical formula COCl2. This colorless gas gained infamy as a chemical weapon during World War I, but it is also a valued industrial reagent and building block in organic synthesis....
is planar). SOCl₂ reacts with water to release hydrogen chloride and sulfur dioxide.

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....
+ O=SCl₂ ? 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....
+ 2 HCl

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....

Production

The major industrial synthesis involves the reaction of sulfur trioxide

Sulfur trioxide

Sulfur trioxide is the chemical compound with the formula SO3. In the gaseous form, this species is a significant pollutant, being the primary agent in acid rain....
and sulfur dichloride

Sulfur dichloride

Sulfur dichloride is the chemical compound with the chemical formula SCl2. This cherry-red liquid is the simplest sulfur chloride and one of the most common....
:

SO₃

Sulfur trioxide

Sulfur trioxide is the chemical compound with the formula SO3. In the gaseous form, this species is a significant pollutant, being the primary agent in acid rain....
+ SCl₂

Sulfur dichloride

Sulfur dichloride is the chemical compound with the chemical formula SCl2. This cherry-red liquid is the simplest sulfur chloride and one of the most common....
? SOCl₂ + SO₂.

Other methods include

SO₂ + PCl₅ ? SOCl₂ + POCl₃

SO₂ + Cl₂

Chlorine

Chlorine...
+ SCl₂ ? 2 SOCl₂

SO₃ + Cl₂ + 2 SCl₂ ? 3 SOCl₂

The first of the above three reactions also affords phosphorus oxychloride

Phosphoryl chloride

Phosphoryl chloride is a colourless liquid with the formula 3. It hydrolyses in moist air to phosphoric acid to release choking fumes of hydrogen chloride....
(phosphoryl chloride), which resembles thionyl chloride in many of its reactions.

Applications

Thionyl chloride is mainly used in the industrial production of organochlorine compounds, which are often intermediates in pharmaceuticals and agrichemicals.

Organic chemistry

Thionyl chloride is used to convert carboxylic acid

Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
s to acyl chloride

Acyl chloride

In organic chemistry, an acyl chloride is an organic compound which is a reactive derivative of a carboxylic acid. As part of its molecular structure, an acyl chloride has the reactive functional group -Carbonyl-Chlorine and has the general formula RCOCl, where R is an organic radical group....
s

and 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 the corresponding alkyl chlorides via an internal nucleophilic substitution.

It is preferred over other reagents such as phosphorus pentachloride because the products of the thionyl chloride reactions, HCl and SO₂ are gaseous, simplifying the purification of the product. Excess thionyl chloride may be removed by distillation

Distillation

Distillation is a method of separation process mixtures based on differences in their Volatility in a boiling liquid mixture. Distillation is a unit operation, or a physical separation process, and not a chemical reaction....
. An example of a reaction of thionyl chloride with an alcohol is in a synthesis of bicifadine

Bicifadine

Bicifadine is a serotonin-norepinephrine reuptake inhibitor developed by DOV Pharmaceutical. It has been developed as an analgesic and is currently under development for the treatment of various pain conditions....
:

Sulfonic acid

Sulfonic acid usually refers to a member of the class of organic acids with the general formula R-S2-OH, where R is usually a hydrocarbon side chain....
s react with thionyl chloride to produce sulfonyl chlorides. Likewise, thionyl chloride will transform sulfinic acids into sulfinyl chlorides and phosphonic acid

Phosphonic acid

In inorganic chemistry, phosphonic acid is a phosphorus oxoacid with a formula of H3PO3, more commonly known as phosphorous acid....
s into phosphoryl chloride

Phosphoryl chloride

Phosphoryl chloride is a colourless liquid with the formula 3. It hydrolyses in moist air to phosphoric acid to release choking fumes of hydrogen chloride....
s.

Thionyl chloride will react with primary formamide

Formamide

Formamide, also known as methanamide, is an amide derived from formic acid. It is a clear liquid which is miscible with water and has an ammonia-like odor....
s to form isocyanide

Isocyanide

An isocyanide is an organic compound with the functional group R-N=C. The CN functionality is connected to the organic fragment via the nitrogen atom, not via carbon as is found in the isomeric nitriles, which have the connectivity R-C=N....
s.

Amide

Amide

In chemistry, an amide is one of three kinds of compounds:* the organic chemistry functional group characterized by a carbonyl group linked to a nitrogen atom , or a compound that contains this functional group ; or...
s will react with thionyl chloride to form imidoyl chlorides. However, primary amides under heating with thionyl chloride will continue on to form nitrile

Nitrile

A nitrile is any organic compound which has a -Carbon=Nitrogen functional group. The -C=N functional group is called a nitrile group....
s.

Inorganic chemistry

Anhydrous

As a general term, a substance is said to be anhydrous if it contains no water. The way of achieving the anhydrous form differs from one substance to another....
metal chlorides may be obtained from hydrated metal chlorides by refluxing in freshly distilled thionyl chloride:

MCl_n·xH₂O + x SOCl₂ → MCl_n + x SO₂ + 2x HCl

Other applications

Thionyl chloride is a component of lithium-thionyl chloride batteries

Battery (electricity)

In electronics, a battery or voltaic cell is a combination of one or more electrochemical cell Galvanic cells which store chemical energy that can be converted into electric potential energy, creating electricity....
, where it forms the anode with lithium

Lithium

Lithium is a chemical element with the symbol Li and atomic number 3. It is a soft alkali metal with a silver-white color. Under standard conditions for temperature and pressure, it is the lightest metal and the least dense solid element....
as the cathode. In military usage, thionyl chloride is used in the "di-di" method of producing G-series nerve agent

Nerve agent

Nerve agents, also referred to as nerve gases though these chemicals are liquid at room temperature, are a class of phosphorus-containing organic chemistry that disrupt the mechanism by which nerves transfer messages to organs....
s.

Safety

SOCl₂ is a reactive compound that can explosively release dangerous gases upon contact with water and other reagents. Industrial production of thionyl chloride is controlled under the Chemical Weapons Convention

Chemical Weapons Convention

The Chemical Weapons Convention is an arms control agreement which outlaws the production, stockpiling and use of chemical warfares. Its full name is the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction....
, where it is listed in schedule 3

List of Schedule 3 substances (CWC)

Schedule 3 substances, in the sense of the Chemical Weapons Convention, are chemicals which can either be used as toxic chemical weapons themselves or used in the manufacture of chemical weapons but which also have legitimate large-scale industrial uses....
.

External links

Usage of in Organic Syntheses
Organic Syntheses

Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds....
*