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Sulfur dichloride

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Sulfur dichloride
Structure and dimensions of the sulfur dichloride molecule
Ball-and-stick model of sulfur dichloride
Ball-and-stick model of sulfur dichloride
Space-filling model of sulfur dichloride
Space-filling model of sulfur dichloride
Names
IUPAC name
  • Dichlorosulfane
  • Sulfur dichloride
  • Sulfur(II) chloride
Other names
  • Chloro thiohypobromite
  • Dichloro sulfide
  • Sulphur chloride
Identifiers
3D model ( JSmol )
ChemSpider
ECHA InfoCard 100.031.014 Edit this at Wikidata
EC Number
  • 234-129-0
RTECS number
  • WS4500000
UNII
UN number 1828
  • InChI=1S/Cl2S/c1-3-2
    Key: FWMUJAIKEJWSSY-UHFFFAOYSA-N
  • InChI=1/Cl2S/c1-3-2
    Key: FWMUJAIKEJWSSY-UHFFFAOYAS
  • ClSCl
Properties
SCl 2
Molar mass 102.96  g·mol ?1
Appearance Cherry-red liquid
Odor Pungent
Density 1.621 g/cm 3
Melting point ?121.0 °C (?185.8 °F; 152.2 K)
Boiling point 59 °C (138 °F; 332 K) (decomposes)
Insoluble, reacts slowly
?49.4·10 ?6 cm 3 /mol
1.5570
Structure
C 2v
Bent
Hazards
GHS labelling :
GHS05: CorrosiveGHS07: Exclamation markGHS09: Environmental hazard
Danger
H314 , H335 , H400
P260 , P261 , P264 , P271 , P273 , P280 , P301+P330+P331 , P303+P361+P353 , P304+P340 , P305+P351+P338 , P310 , P312 , P321 , P363 , P391 , P403+P233 , P405 , P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
1
1
234 °C (453 °F; 507 K)
Safety data sheet (SDS) ICSC 1661
Related compounds
Related
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY   verify  ( what is   checkY ☒N  ?)

Sulfur dichloride is the chemical compound with the formula SCl 2 . This cherry-red liquid is the simplest sulfur chloride and one of the most common, and it is used as a precursor to organosulfur compounds. It is a highly corrosive and toxic substance, and it reacts on contact with water to form chlorine-containing acids.

Chlorination of sulfur [ edit ]

SCl 2 is produced by the chlorination of either elemental sulfur or disulfur dichloride . [1] The process occurs in a series of steps, some of which are:

S 8 + 4 Cl 2 → 4 S 2 Cl 2 ; ΔH = ?58.2 kJ/mol
S 2 Cl 2 + Cl 2 ↔ 2 SCl 2 ; ΔH = ?40.6 kJ/mol

The addition of Cl 2 to S 2 Cl 2 has been proposed to proceed via a mixed valence intermediate Cl 3 S?SCl . SCl 2 undergoes even further chlorination to give SCl 4 , but this species is unstable at near room temperature. It is likely that several S n Cl 2 exist where n > 2.

Disulfur dichloride , S 2 Cl 2 , is the most common impurity in SCl 2 . Separation of SCl 2 from S 2 Cl 2 is possible via distillation with PCl 3 to form an azeotrope of 99% purity, however sulfur dichloride loses chlorine slowly at room temperature and reverts to disulfur dichloride. Pure samples may be stored in sealed glass ampules which develop a slight positive pressure of chlorine, halting the decomposition.

Use of SCl 2 in chemical synthesis [ edit ]

SCl 2 is used in organic synthesis . It adds to alkenes to give chloride-substituted thioethers. Illustrative is its addition to 1,5-cyclooctadiene to give a bicyclic thioether [2] A well tested method for the production of the mustard gas bis(2-chloroethyl)sulfide , is the addition of ethylene to sulfur dichloride: [3]

SCl 2 + 2 C 2 H 4 → (ClC 2 H 4 ) 2 S

SCl 2 is also a precursor to several inorganic sulfur compounds. Treatment with fluoride salts gives SF 4 via the decomposition of the intermediate sulfur difluoride . With H 2 S , SCl 2 reacts to give "lower" sulfanes such as S 3 H 2 .

Reaction with ammonia affords sulfur nitrides related to S 4 N 4 . Treatment of SCl 2 with primary amines gives sulfur diimides . One example is di- t -butylsulfurdiimide. [4]

Safety considerations [ edit ]

SCl 2 hydrolyzes with release of HCl . Old samples contain Cl 2 . [ citation needed ]

References [ edit ]

  1. ^ F. Feher "Dichloromonosulfane" in Handbook of Preparative Inorganic Chemistry, 2nd Ed. Edited by G. Brauer, Academic Press, 1963, NY. Vol. 1. p. 370.
  2. ^ Bishop, Roger (1992). "9-Thiabicyclo[3.3.1]nonane-2,6-dione" . Organic Syntheses . 70 : 120 ; Collected Volumes , vol. 9, p. 692 .
  3. ^ R. J. Cremlyn “An Introduction to Organosulfur Chemistry” John Wiley and Sons: Chichester (1996). ISBN   0-471-95512-4 .
  4. ^ Kresze, G.; Wucherpfennig, W. (1967). "New Methods of Preparative Organic Chemistry V: Organic Syntheses with Imides of Sulfur Dioxide". Angewandte Chemie International Edition in English . 6 (2): 149?167. doi : 10.1002/anie.196701491 . PMID   4962859 .
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