Carbyl sulfate

Carbyl sulfate

Names
IUPAC name 1,3,2,4-Dioxadithiane 2,2,4,4-tetraoxide
Identifiers
CAS Number	503-41-3
ChemSpider	61459
Jmol interactive 3D	Image
PubChem	68151
InChI InChI=1S/C2H4O6S2/c3-9(4)2-1-7-10(5,6)8-9/h1-2H2 Key: VSANMHWDSONVEE-UHFFFAOYSA-N InChI=1/C2H4O6S2/c3-9(4)2-1-7-10(5,6)8-9/h1-2H2 Key: VSANMHWDSONVEE-UHFFFAOYAN
SMILES O=S1(=O)OS(=O)(=O)OCC1
Properties
Chemical formula	C2H4O6S2
Molar mass	188.17 g·mol^−1
Appearance	White solid
Melting point	107.5–109 °C (225.5–228.2 °F; 380.6–382.1 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Carbyl sulfate is an organosulfur compound with the formula C₂H₄(SO₃)₂. This a white solid is the product of the reaction of sulfur trioxide and ethylene. It is used in preparation of some dyes and other organosulfur compounds.^[1]

Reactions

As a cyclic sulfate ester, it is an alkylating agent. Hydrolysis affords ethionic acid:

C₂H₄(SO₃)₂ + H₂O → HOSO₃C₂H₄SO₃H

Ethionic acid undergoes further hydrolysis to isethionic acid:

HOSO₃C₂H₄SO₃H + H₂O → HOC₂H₄SO₃H + H₂SO₄

Isethionic acid is a precursor to vinylsulfonic acid.

References

1. Kosswig, Kurt (2000). "Sulfonic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry (Wiley-VCH). doi:10.1002/14356007.a25_503. ISBN 3-527-30673-0.

Further reading

• Breslow, David S.; Hough, Robert R. (1957). "Synthesis of sodium ethylenesulfonate from ethylene". Journal of the American Chemical Society 79: 5000–5002. doi:10.1021/ja01575a046.