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Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately volatile colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes (50,000 short tons) per year being produced during the early 1990s. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.
Thionyl chloride is sometimes confused with sulfuryl chloride, SO2Cl2, but the properties of these compounds differ significantly. Sulfuryl chloride is a source of chlorine whereas thionyl chloride is a source of chloride ions.
Thionyl chloride has a long shelf life, however "aged" samples develop a yellow hue, possibly due to the formation of disulfur dichloride. It slowly decomposes to S2Cl2, SO2 and Cl2 at just above the boiling point. Thionyl chloride is susceptible to photolysis, which primarily proceeds via a radical mechanism. Samples showing signs of ageing can be purified by distillation under reduced pressure, to give a colourless liquid.
Thionyl chloride is mainly used in the industrial production of organochlorine compounds, which are often intermediates in pharmaceuticals and agrichemicals. It usually is preferred over other reagents, such as phosphorus pentachloride, as its by-products (HCl and SO2) are gaseous, which simplifies purification of the product.
Many of the products of thionyl chloride are themselves highly reactive and as such it is involved in a wide range of reactions.
By a similar process it also reacts with alcohols to form alkyl chlorides. If the alcohol is chiral the reaction generally proceeds via an SNi mechanism with retention of stereochemistry; however, depending on the exact conditions employed, stereo-inversion can also be achieved. Historically the use of SOCl2 in combination with a tertiary amine such as pyridine was called the Darzens halogenation, but this name is rarely used by modern chemists.
Conversion of a secondary alcohol to a chloroalkane by thionyl chloride.
As SOCl2 reacts with water it can be used to dehydrate various metal chloride hydrates, such MgCl2·6H2O, AlCl3·6H2O, and FeCl3·6H2O. This conversion involves treatment with refluxing thionyl chloride and follows the following general equation:
MCln·xH2O + x SOCl2 -> MCln + x SO2 + 2x HCl
Thionyl chloride can engage in a range of different electrophilic addition reactions. It adds to alkenes in the presence of AlCl3 to form an aluminium complex which can be hydrolysed to form a sulfinic acid. Both aryl sulfinyl chlorides and diaryl sulfoxides can be prepared from arenes through reaction with thionyl chloride in triflic acid or the presence of catalysts such as BiCl3, Bi(OTf)3, LiClO4 or NaClO4.
In the laboratory, a reaction between thionyl chloride and an excess of anhydrous alcohol can be used to produce anhydrous alcoholic solutions of HCl.
These non-rechargeable batteries have many advantages over other forms of lithium battery such as a high energy density, a wide operational temperature range and long storage and operational lifespans. However, their high cost and safety concerns have limited their use. The contents of the batteries are highly toxic and require special disposal procedures; additionally, they may explode if shorted. The technology was used on the Sojourner Mars rover.
SOCl2 is a reactive compound that can violently release dangerous gases upon contact with water and other reagents. It is also controlled under the Chemical Weapons Convention and listed as a Schedule 3 substance since it is used in the "di-di" method of producing G-series nerve agents.
^Thionyl chloride in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD), http://webbook.nist.gov (retrieved 2014-05-11)
^Brauer, Georg, ed. (1963). Handbook of Preparative Inorganic Chemistry. 1. Translated by Scripta Technica; Reed, F. (2nd ed.). New York, NY: Academic Press. p. 383. ISBN978-0121266011.
^Donovan, R. J.; Husain, D.; Jackson, P. T. (1969). "Spectroscopic and kinetic studies of the SO radical and the photolysis of thionyl chloride". Transactions of the Faraday Society. 65: 2930. doi:10.1039/TF9696502930.
^Friedman, L.; Wetter, W. P. (1967). "Purification of thionyl chloride". Journal of the Chemical Society A: Inorganic, Physical, Theoretical: 36. doi:10.1039/J19670000036.
^Brenner, M.; Huber, W. (1953). "Herstellung von ?-Aminosäureestern durch Alkoholyse der Methylester" [Manufacture of ?-amino acid esters by alcoholysis of methyl esters]. Helvetica Chimica Acta (in German). 36 (5): 1109-1115. doi:10.1002/hlca.19530360522.
^Peyronneau, M.; Roques, N.; Mazières, S.; Le Roux, C. (2003). "Catalytic Lewis Acid Activation of Thionyl Chloride: Application to the Synthesis of Aryl Sulfinyl Chlorides Catalyzed by Bismuth(III) Salts". Synlett (5): 0631-0634. doi:10.1055/s-2003-38358.
^Bandgar, B. P.; Makone, S. S. (2004). "Lithium/Sodium Perchlorate Catalyzed Synthesis of Symmetrical Diaryl Sulfoxides". Synthetic Communications. 34 (4): 743-750. doi:10.1081/SCC-120027723. S2CID96348273.
^The German chemist Georg Ludwig Carius noted that, when the reaction mixture that produced thionyl chloride was distilled, the crude mixture initially released substantial quantities of gas, so that phosphoryl chloride (POCl3) was carried into the receiver. Carius, L. (1859). "Ueber die Chloride des Schwefels und deren Derivate" [On sulfur chloride and its derivatives]. Annalen der Chemie und Pharmacie (in German). 111: 93-113. doi:10.1002/jlac.18591110111. From p. 94: " ... dabei ist jedoch die Vorsicht zu gebrauchen, ... und nie reines Chlorthionyl erhalten wird." ( ... however, during that [i.e., the fractional distillation], caution must be used, [so] that one carefully avoids a concentration of hydrogen chloride or excess sulfurous acid in the liquid that is to be distilled, as otherwise, by the evolution of gas that occurs at the start of the distillation, much phosphoryl chloride is transferred and pure thionyl chloride is never obtained.)
^Carius, L. (1859). "Ueber die Chloride des Schwefels und deren Derivate" [On sulfur chloride and its derivatives]. Annalen der Chemie und Pharmacie (in German). 111: 93-113. doi:10.1002/jlac.18591110111.
On p. 94, Carius notes that thionyl chloride can be " ... mit Vortheil zur Darstellung wasserfreier Säuren verwenden." ( ... used advantageously for the preparation of acid anhydrides.) Also on p. 94, Carius shows chemical equations in which thionyl chloride is used to transform benzoic acid (OC7H5OH) into benzoyl chloride (ClC7H5O) and to transform sodium benzoate into benzoic anhydride. On p. 96, he mentions that thionyl chloride will transform methanol into methyl chloride (Chlormethyl). Thionyl chloride behaves like phosphoryl chloride: from pp. 94-95: "Die Einwirkung des Chlorthionyls ... die Reaction des Chlorthionyls weit heftiger statt." (The reaction of thionyl chloride with [organic] substances containing oxygen proceeds in general parallel to that of phosphoryl chloride; where the latter exerts an effect, thionyl chloride usually does so also, only in nearly all cases the reaction occurs far more vigorously.)