Disulfur dichloride

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Dis ulfur dichloride is the inorganic compound of sulf ur and chlorine w ith the f ormula S2Cl2.[4][5][6][7]
Disulfur dichloride
Some alternative names f or this compound are sulfur monochloride (the name implied by its empirical f ormula, SCl), disulphur
dichloride (British English Spelling) and sulphur monochloride (British English Spelling). S2Cl2 has the structure implied by the f ormula
Cl−S−S−Cl, w herein the angle betw een the Cla−S−S and S−S−Clb planes is 90°. This structure is ref erred to as gauche, and is akin to
that f or H2O2. A rare isomer of S2Cl2 is S=SCl2; this isomer f orms transiently w hen S2Cl2 is exposed to UV-radiation (see
thiosulf oxides).

Contents [hide]
1 Synthesis, basic properties, reactions
1.1 Reactions
2 Applications
Names
3 Safety and regulation
IUPAC name
4 References Disulf ur dichloride
Sy stematic IUPAC name
Dichlorodisulf ane
Synthesis, basic properties, reactions [ edit ]
Other names
Pure disulf ur dichloride is a yellow liquid that "smokes" in moist air due to reaction w ith w ater. An idealized (but complicated) equation Bis[chloridosulf ur](S–S)

is: Dimeric sulf enic chloride

Sulf ur monochloride
16 S2Cl2 + 16 H2O → 8 SO2 + 32 HCl + 3 S8
Identifiers
It is produced by partial chlorination of elemental sulf ur. The reaction proceeds at usable rates at room temperature. In the laboratory, CAS Number 10025-67-9
chlorine gas is led into a f lask containing elemental sulf ur. As disulf ur dichloride is f ormed, the contents become a golden yellow 85408-26-0 (isobutenate)
liquid:[8]
3D model (JSmol) Interactiv e image
S8 + 4 Cl2 → 4 S2Cl2, ΔH = −58.2 kJ/mol
ChemSpider 23192
Excess chlorine produces sulf ur dichloride, w hich causes the liquid to become less yellow and more orange-red: 19158348 (isobutenate)
ECHA Inf oCard 100.030.021
S2Cl2 + Cl2 ↔ 2 SCl2, ΔH = −40.6 kJ/mol
EC Number 233-036-2
The reaction is reversible, and upon standing, SCl2 releases chlorine to revert to the disulf ur dichloride. Disulf ur dichloride has the
MeSH Sulf ur+monochloride
ability to dissolve large quantities of sulf ur, w hich ref lects in part the f ormation of polysulf anes:
PubChem CID 24807
S2Cl2 + n S → S2+nCl2 RTECS number WS4300000
UNII NJ7YR2EV0D
Disulf ur dichloride can be purif ied by distillation f rom excess elemental sulf ur.
UN number 3390
S2Cl2 also arises f rom the chlorination of CS2 as in the synthesis of thiophosgene. CompTox DTXSID3042427
Dashboard (EPA)
Reactions [ edit ] InChI [show]

S2Cl2 hydrolyzes to sulf ur dioxide and elemental sulf ur. When treated w ith hydrogen sulf ide, polysulf anes are f ormed as indicated in SMILES [show]

the f ollow ing idealized f ormula: Properties

Chemical f ormula S2Cl2
2 H2S + S2Cl2 → H2S4 + 2 HCl
Molar mass 135.04 g/mol
It reacts w ith ammonia to give heptasulf ur imide (S7NH) and related S−N rings S8−x(NH) x (x = 2, 3). Appearance Light-amber to y ellow-red,
oily liquid[1]

Applications [ edit ]
Odor pungent, nauseating,
irritating[1]
S2Cl2 has been used to introduce C−S bonds. In the presence of aluminium chloride (AlCl3), S2Cl2 reacts w ith benzene to give Density 1.688 g/cm 3
diphenyl sulf ide: Melting point −80 °C (−112 °F; 193 K)

S2Cl2 + 2 C6H6 → (C6H5) 2S + 2 HCl + 1/8 S8 Boiling point 137.1 °C (278.8 °F;
410.2 K)
Anilines (1) react w ith S2Cl2 in the presence of NaOH to give 1,2,3-benzodithiazolium salts (2) (Herz reaction) w hich can be Solubility in water decomposes, with loss of
transf ormed into ortho-aminothiophenolates (3), these species are precursors to thioindigo dyes. HCl
Solubility soluble in ethanol, benzene,
ether, chlorof orm, CCl4[2]
Vapor pressure 7 mmHg (20 °C)[1]
Magnetic −62.2·10−6 cm 3/mol
susceptibility (χ )
Ref ractiv e index 1.658
It is also used to prepare sulf ur mustard, commonly know n as "mustard gas", by reaction w ith ethylene at 60 °C (the Levinstein (nD)
process): Structure
Coordination C 2, gauche
S2Cl2 + 2 C2H4 → (ClC2H4) 2S + 1/8 S8 geometry
Dipole moment 1.60 D [2]
Other uses of S2Cl2 include the manuf acture of sulf ur dyes, insecticides, and synthetic rubbers. It is also used in cold vulcanization
of rubbers, as polymerization catalyst f or vegetable oils and f or hardening sof t w oods. Hazards
Saf ety data sheet ICSC 0958

Safety and regulation [ edit ]

EU classif ication
(DSD) (outdated)
Toxic (T)
Harmf ul (Xn)
This substance is listed in Schedule 3 Part B – Precursor Chemicals of the Chemical Weapons Convention (CWC). Facilities that Corrosiv e (C)
produce and/or process and/or consume Scheduled chemicals may be subject to control, reporting mechanisms and inspection by Dangerous f or the
env ironment (N)
the OPCW (Organisation f or the Prohibition of Chemical Weapons).
R-phrases R14, R20, R25, R29, R35,
(outdated) R50
References [ edit ] S-phrases (S1/2), S26, S36/37/39,
1. ^a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0578" . National Institute f or Occupational Saf ety and Health (NIOSH). (outdated) S45, S61

2. ^ a b Prady ot Patnaik. Handbook of Inorganic Chemicals. McGraw-Hill, 2002, ISBN 0-07-049439-8

3. ^ "Sulf ur monochloride" . Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute f or Occupational Saf ety and Health
 (NIOSH). NFPA 704
4. ^ Holleman, A. F.; Wiberg, E. Inorganic Chemistry Academic Press: San Diego, 2001. ISBN 0-12-352651-5. (f ire diamond) 1
5. ^ Hartman, W. W.; Smith, L. A.; Dickey, J. B. (1934). "Dipheny lsulf ide" . Organic Syntheses. 14: 36.; Collective Volume, 2, p. 242
2 1
6. ^ R. J. Cremly n An Introduction to Organosulfur Chemistry John Wiley and Sons: Chichester (1996). ISBN 0-471-95512-4
7. ^ Garcia-Valv erde M., Torroba T. (2006). "Heterocy clic chemistry of sulf ur chlorides – Fast way s to complex heterocy cles". European Journal of Flash point 118.5 °C (245.3 °F;
Organic Chemistry. 2006 (4): 849–861. doi:10.1002/ejoc.200500786 . 391.6 K)
8. ^ F. Fehér "Dichlorodisulf ane" in Handbook of Preparative Inorganic Chemistry, 2nd Ed. Edited by G. Brauer, Academic Press, 1963, NY. Vol. 1. p. Autoignition 234 °C (453 °F; 507 K)
temperature
371.
Lethal dose or concentration (LD, LC):
LC Lo (lowest 150 ppm (mouse, 1 min)[3]
published)
NIOSH (US health exposure limits):
PEL TWA 1 ppm (6 mg/m 3)[1]
(Permissible)
REL C 1 ppm (6 mg/m 3)[1]
(Recommended)
IDLH 5 ppm [1]
(Immediate
danger)
Related compounds
Related sulf ur Sulf ur dichloride
chlorides Thiony l chloride
Sulf ury l chloride
Related Disulf ur dif luoride
compounds Disulf ur dibromide
Except where otherwise noted, data are giv en
f or materials in their standard state (at 25 °C
[77 °F], 100 kPa).
v erif y (what is ?)
Inf obox ref erences

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