Thionyl chloride
General
Systematic name	Thionyl dichloride
Other names	Sulfurous oxychloride Sulfurous dichloride Sulfinyl chloride Sulfinyl dichloride Dichlorosulfoxide
Molecular formula	SOCl2
Molar mass	118.97 g/mol
Appearance	clear to yellow odorous liquid
CAS number	[7719-09-7]
Properties
Density	1.638 g/ml, liquid
Solubility in water	Reacts
Melting point	−104.5 °C
Boiling point	76 °C
Viscosity	? cP at ? °C
Structure
Molecular shape	pyramidal
Dipole moment	? D
Hazards
MSDS	External MSDS
EU classification	Corrosive (C)
NFPA 704
R-phrases	R14, R20/22, R29, R35
S-phrases	S1/2, S26, S36/37/39, S45
Flash point	non flammable
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Other anions	Thionyl bromide Thionyl iodide
Related compounds	Sulfuryl chloride
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Thionyl chloride (or thionyl dichloride) is an inorganic compound with the formula SOCl₂. SOCl₂ is a reactive chemical reagent used in chlorination reactions. It is a colorless, distillable liquid at room temperature and pressure that decomposes above 140 °C. SOCl₂ is sometimes confused with sulfuryl chloride, SO₂Cl₂, but the chemical properties of these S(IV) and S(VI) compounds differ significantly. Image File history File links Thionyl_Chloride. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... A substance is soluble in a fluid if it dissolves in that fluid. ... Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid. ... The pitch drop experiment at the University of Queensland. ... The poise (P) is the cgs unit of viscosity, 1 P = 1 g·cm-1·s-1 The SI analog is 1 pascal second (Pa·s) = 1 kg·m-1·s-1 = 10 P. It is named after Jean Louis Marie Poiseuille. ... four sp³ orbitals three sp² orbitals In chemistry, hybridisation is the mixing of atomic orbitals belonging to a same electron shell to form new orbitals suitable for the qualitative description of atomic bonding properties. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main source of European Union law concerning chemical safety. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... The flash point of a fuel is the lowest temperature at which it can form an ignitable mix with air. ... The refractive index of a material is the factor by which the phase velocity of electromagnetic radiation is slowed relative to vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... IR spectrum of a thin film of liquid ethanol. ... Nuclear Magnetic Resonance Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... Mass spectrometry is an analytical technique to measure the mass-to-charge ratio (m/q) of ions. ... // An ion is an atom or group of atoms with a net electric charge. ... Sulfuryl chlorideis a compound composed of sulfur,oxygen, and chlorine, having a formula of SO2Cl2. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... An inorganic compound is a chemical compound not containing carbon and hydrogen atoms bonded to each other. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number sulfur, S, 16 Chemical series nonmetals Group, Period, Block 16, 3, p Appearance lemon yellow Atomic mass 32. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Chalcogens Group, Period, Block 16, 2, p Appearance colorless Atomic mass 15. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... When purchasing or preparing chemicals, reagent describes chemical substances of sufficient purity for use in chemical analysis, chemical reactions or physical testing. ... A chemical reaction is a process that results in the interconversion of chemical substances . ... A liquid will assume the shape of its container. ... Temperature is the physical property of a system which underlies the common notions of hot and cold; the material with the higher temperature is said to be hotter. ... Pressure (symbol: p) is the force per unit area acting on a surface in a direction perpendicular to that surface. ... Sulfuryl chlorideis a compound composed of sulfur,oxygen, and chlorine, having a formula of SO2Cl2. ...

Properties and structure

The molecule SOCl₂ is pyramidal, indicating the presence of a lone pair of electrons on the S(IV) center. In contrast, COCl₂ is planar. Phosgene (also known as carbonyl chloride, COCl2) is a highly toxic gas or refrigerated liquid that was used as a chemical weapon in World War I. It has no color, but is detectable in air by its odor, which resembles moldy hay. ...

SOCl₂ reacts with water to release hydrogen chloride (HCl) and sulfur dioxide (SO₂). Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... Hydrogen chloride, also known under the name HCl, is a highly corrosive and toxic colorless gas that forms white fumes on contact with humidity. ... Sulfur dioxide (or Sulphur dioxide) has the chemical formula SO2. ...

H₂O + O=SCl₂ → SO₂ + 2 HCl

Because of its high reactivity toward water, SOCl₂ would not be expected to occur in nature. Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... Sulfur dioxide (or Sulphur dioxide) has the chemical formula SO2. ... Hydrogen chloride, also known under the name HCl, is a highly corrosive and toxic colorless gas that forms white fumes on contact with humidity. ...

Uses

SOCl₂ is widely used both both in the laboratory and on an industrial scale. It reacts with carboxylic acids to produce acyl chlorides, Structure of a carboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)-OH, usually written as COOH. In general, the salts and anions of carboxylic acids are called carboxylates. ... General Chemical Structure of an Acyl Chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound which is a reactive derivative of a carboxylic acid. ...

RC(O)OH + O=SCl₂ → RC(O)Cl + SO₂ + HCl

and with alcohols to produce alkyl chlorides via a SNi reaction mode. Structure of a carboxylic acid Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)-OH, usually written as COOH. In general, the salts and anions of carboxylic acids are called carboxylates. ... General Chemical Structure of an Acyl Chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound which is a reactive derivative of a carboxylic acid. ... Sulfur dioxide (or Sulphur dioxide) has the chemical formula SO2. ... Hydrogen chloride, also known under the name HCl, is a highly corrosive and toxic colorless gas that forms white fumes on contact with humidity. ... In general usage, alcohol (from Arabic al-kukhÅ«l الكحول = the spirit, the chemical.) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... In chemistry, an alkyl halide is an organic molecule of the form R_X, where X is a halide and R contains a carbon atom bonded to other functional groups or hydrogens. ... The National Intelligence Service (Serviço Nacional de Informações, or SNI) of Brazil was an intelligence agency formed by the Castelo Branco government in 1964. ...

R-OH + O=SCl₂ → R-Cl + SO₂ + HCl

Thionyl chloride is used inside lithium-thionyl chloride batteries as the positive active material with lithium as the negative active material. It is also used as a reagant for the production of other chemical compounds or materials. A major application is in the preparation of acid chlorides from carboxylic acids, including the important organic reactant acetyl chloride made via the following reaction: In general usage, alcohol (from Arabic al-kukhūl الكحول = the spirit, the chemical.) refers almost always to ethanol, also known as grain alcohol, and often to any beverage that contains ethanol (see alcoholic beverage). ... In chemistry, an alkyl halide is an organic molecule of the form R_X, where X is a halide and R contains a carbon atom bonded to other functional groups or hydrogens. ... Sulfur dioxide (or Sulphur dioxide) has the chemical formula SO2. ... Hydrogen chloride, also known under the name HCl, is a highly corrosive and toxic colorless gas that forms white fumes on contact with humidity. ... Four double-A (AA) rechargeable batteries In science and technology, a battery is a device that stores energy and makes it available in an electrical form. ... General Name, Symbol, Number lithium, Li, 3 Chemical series alkali metals Group, Period, Block 1, 2, s Appearance silvery white/gray Atomic mass 6. ... A chemical compound is a chemical substance formed from two or more elements, with a fixed ratio determining the composition. ... In organic chemistry, an acid chloride (or acyl chloride) is very reactive derivative of a carboxylic acid. ... Acetyl chloride, also known as ethanoyl chloride, is an acid chloride derived from acetic acid. ...

H₃C-C(O)OH + O=SCl₂ → H₃C-C(O)Cl + SO₂ + H-Cl

Flash point 43 Â°C R-phrases , S-phrases , , , US Permissible exposure limit (PEL) 10 ppm Supplementary data page Structure & properties n, εr, etc. ... Acetyl chloride, also known as ethanoyl chloride, is an acid chloride derived from acetic acid. ... Sulfur dioxide (or Sulphur dioxide) has the chemical formula SO2. ... Hydrogen chloride, also known under the name HCl, is a highly corrosive and toxic colorless gas that forms white fumes on contact with humidity. ...

Synthesis of thionyl chloride

The major industrial synthesis involves the reaction of sulfur trioxide and sulfur dichloride^[1]: Sulfur trioxide (British spelling: Sulphur trioxide) has the chemical formula SO3. ... Sulphur Dichloride Sulpur dichloide is a cherry-red liquid at room temperature that is produced from the chlorination of [S2Cl2] (disulphur dichloride). ...

SO₃ + SCl₂ → SOCl₂ + SO₂

Other methods include: Sulfur trioxide (British spelling: Sulphur trioxide) has the chemical formula SO3. ... Sulphur Dichloride Sulpur dichloide is a cherry-red liquid at room temperature that is produced from the chlorination of [S2Cl2] (disulphur dichloride). ... Sulfur dioxide (or Sulphur dioxide) has the chemical formula SO2. ...

SO₂ + PCl₅ → SOCl₂ + POCl₃

SO₂ + Cl₂ + SCl₂ → 2 SOCl₂

SO₃ + Cl₂ + 2 SCl₂ → 3 SOCl₂

Sulfur dioxide (or Sulphur dioxide) has the chemical formula SO2. ... Phosphorus Trichloride Phosphorus Pentachloride Phosphorus trichloride (PCl3) and phosphorus pentachloride (PCl5) are reactive chemicals used as chlorinating reagents in a chemical laboratory. ... Phosphorus trichloride Phosphorus pentachloride (gas phase structure) Phosphorus oxychloride[1] Phosphorus trichloride (PCl3) and phosphorus pentachloride (PCl5) are reactive chemicals used as chlorinating reagents in a chemical laboratory. ... Sulfur dioxide (or Sulphur dioxide) has the chemical formula SO2. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... Sulphur Dichloride Sulpur dichloide is a cherry-red liquid at room temperature that is produced from the chlorination of [S2Cl2] (disulphur dichloride). ... Sulfur trioxide (British spelling: Sulphur trioxide) has the chemical formula SO3. ... General Name, Symbol, Number chlorine, Cl, 17 Chemical series halogens Group, Period, Block 17, 3, p Appearance yellowish green Atomic mass 35. ... Sulphur Dichloride Sulpur dichloide is a cherry-red liquid at room temperature that is produced from the chlorination of [S2Cl2] (disulphur dichloride). ...

Safety and toxity considerations

SOCl₂ is toxic, corrosive, and lachrymatory. It is a skin and inhalation hazard, as well as being odorous, For a list of biologically injurious substances, including toxins and other materials, as well as their effects, see poison. ... Corrosion is the destructive reaction of a metal with another material, e. ... Categories: Stub | Chemical weapons ... Diagram of the layers of human skin In zootomy and dermatology, skin is an organ of the integumentary system composed of a layer of tissues that protect underlying muscles and organs. ...

Industrial production of thionyl chloride is controlled under the Chemical Weapons Convention, where it is listed in schedule 3. Chemical Weapons Convention Opened for signature January 13, 1993 at Paris Entered into force April 29, 1997 Conditions for entry into force Ratification by 50 states and the convening of a Preperatory Commission Parties 170 The Chemical Weapons Convention is an arms control agreement which outlaws the production, stockpiling and... Schedule 3 substances, in the sense of the Chemical Weapons Convention, are either toxic enough to be used as chemical weapons, or precursors of other listed substances. ...

References

1. N. N. Greenwood, A. Earnshaw, Chemistry of the Elements, Pergamon Press, 1984.

External links

• International Chemical Safety Card 1409
• NIOSH Pocket Guide to Chemical Hazards
• European Chemicals Bureau