Disulfur dichloride

Structural formula
General
Surname	Disulfur dichloride
other names	Chlorosulfur Dichlorodisulfane half chlorosulfur (obsolete) Sulfur (I) chloride Sulfur chloride Sulfur monochloride
Molecular formula	S 2 Cl 2
Brief description	yellow to orange liquid with a foul odor
External identifiers / databases
CAS number 10025-67-9 EC number 233-036-2 ECHA InfoCard 100.030.021 PubChem 24807 Wikidata Q414657
properties
Molar mass	135.04 g mol −1
Physical state	liquid
density	1.69 g cm −3 (20 ° C)
Melting point	−80 ° C
boiling point	138 ° C
Vapor pressure	9.2 h Pa (20 ° C)
solubility	violent decomposition with water soluble in ethanol and diethyl ether
Refractive index	1.658 (20 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 301 + 331-314-400 EUH: 014-029 P: 280-301 + 310 + 330-303 + 361 + 353-304 + 340 + 310-305 + 351 + 338-403 + 233
MAK	not yet classified Switzerland: 1 ml m −3 or 6 mg m −3
Toxicological data	131 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Disulfur dichloride is a chemical compound from the group of sulfur chlorides , which is mainly used as a sulfidizing and chlorinating agent.

Extraction and presentation

S ₂ Cl ₂ is produced by chlorination of elemental sulfur :

${\displaystyle {\ce {2S + Cl2 -> S2Cl2}}}$ (ΔH = −58.2 kJ / mol)

With excess chlorine, the product reacts further to form sulfur dichloride :

${\displaystyle {\ce {S2Cl2 + Cl2 -> 2SCl2}}}$ (ΔH = −40.6 kJ / mol)

In practice, the production can be carried out by introducing chlorine into molten sulfur and subsequent purification by fractional distillation. In industry, chlorination takes place continuously at 240 ° C. The by-product sulfur dichloride is converted into disulfur dichloride by heating to reflux with the addition of sulfur.

properties

Physical Properties

Disulfur dichloride is a clear yellow to orange, fuming, oily liquid with a penetrating, suffocating odor that boils at 138 ° C under normal pressure . According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in bar, T in K) with A = 4.0648, B = 1417.43 and C = −61.685 in the temperature range from 266 to 411 K. The heat capacity at 25 ° C is 124.3 J · mol ⁻¹ · K ⁻¹ or 0.92 J · g ⁻¹ · K ⁻¹ . It has a viscosity of 0.9 mPa · s at 20 ° C.

Chemical properties

The compound reacts violently with water to form a variety of products such as sulfur , hydrogen chloride , sulfur dioxide , hydrogen sulfide and thiosulfate. Up to 67% sulfur can be dissolved in the compound at room temperature, this being incorporated with the formation of a chain S _n Cl ₂ with n = 2 to 100.

Disulfur dichloride is a sulphidating and chlorinating agent , which on the one hand behaves like dissolved chlorine, but on the other hand can form sulphide bonds with a large number of (organic) compounds.

In synthetic organic chemistry, it is used as a reagent for the production of various sulfur-containing organic compounds. Thus, thioketones and thioaldehydes can be obtained by reaction with hydrazones . The addition reaction to alkenes gives the corresponding episulfides via primary addition intermediates . Disulfides can be obtained via substitution reactions with aromatics . Reaction with oximes makes heterocyclic compounds of the dithiazole type accessible.

use

Disulfur dichloride is used industrially for the production of:

• Additives for high pressure lubricants and cutting oils
• Rubber vulcanizing agents
• Sulfur dichloride , sulfur tetrachloride and thionyl chloride
• other organic sulfur compounds, which in turn are used in the manufacture of pharmaceuticals, pesticides, dyes and rubber
• Chlorination of dicarboxylic acids, e.g. B. Oxalic acid (ethanedioic acid) to oxalyl chloride

It also serves as a catalyst in chlorination reactions, e.g. B. Chlorination of acetic acid .

safety instructions

Disulfur dichloride is a raw material for the manufacture of chemical warfare agents and is therefore under export control.

Individual evidence

1. ↑ Sulfur chloride . In: Meyers Großes Konversations-Lexikon . 6th edition. Volume 18, Bibliographisches Institut, Leipzig / Vienna 1909, p.  157 .
2. ↑ ^{a b c d e f g h i} Entry on disulfur dichloride in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
3. ↑ ^{a b c} Data sheet disulfur dichloride (PDF) from Merck , accessed on February 23, 2010.
4. ↑ Sulfur monochloride data sheet from Sigma-Aldrich , accessed on March 28, 2011 ( PDF ).
5. ↑ Entry on Disulphur dichloride in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
6. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 10025-67-9 or disulfur dichloride ), accessed on November 2, 2015.
7. ↑ G. Brauer (Ed.), Handbook of Preparative Inorganic Chemistry 2nd ed., Vol. 1, Academic Press 1963, pp. 371-372.
8. ↑ ^{a b c d} Entry on sulfur chlorides. In: Römpp Online . Georg Thieme Verlag, accessed on July 26, 2017.
9. ↑ Stull, DR: Vapor Pressure of Pure Substances Organic Compounds in Ind. Eng. Chem. 39 (1947) 517-540, doi : 10.1021 / ie50448a022 .
10. ↑ Chase, MW, Jr., NIST-JANAF Themochemical Tables, Fourth Edition, J. Phys. Chem. Ref. Data, Monograph 9, 1998, 1-1951.
11. ↑ L. Kolditz: Inorganische Chemie , Deutscher Verlag der Wissenschaften, Berlin 1983, p. 469.
12. ^ E-EROS Encyclopedia of Reagents for Organic Synthesis , 1999-2013, John Wiley and Sons, Inc., entry for Disulfur Dichloride, accessed July 25, 2017 .
13. ↑ Export control

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