Ethylenesulfate

Chemical Properties

White Solid

Uses

1,3,2-Dioxathiolane 2,2-Dioxide is an alkylating agent with carcinogenic activty.

Uses

1,3,2-Dioxathiolane 2,2-dioxide may be employed in the preparation of imidazolidinium salts.

Synthesis

Cyclic sulfates of 1,2-diols (1,3,2-dioxathiolane 2,2-dioxides) are most easily prepared in a two-step procedure (eq 1). The reaction of a 1,2-diol with Thionyl Chloride leads to a cyclic sulfite, which is then oxidized to the corresponding cyclic sulfate (1). Direct conversion of a 1,2-diol to a cyclic sulfate using Sulfuryl Chloride is generally less efficient.

Toxics Screening Level

The initial threshold screening level (ITSL) for 1,3,2-dioxathiolane,2,2-dioxide (CAS #1072-53-3) is 0.1 μg/m3 annual averaging time.

Precautions

The structural similarity between cyclic sulfates and Dimethyl Sulfate must be recognized. Dimethyl sulfate, and to a lesser extent, ethylene sulfate, are carcinogenic and potent alkylating agents that are toxic by inhalation and ingestion. Cyclic sulfates must, as a result, be treated with extreme care.

References

[1] Patent: CN108822073, 2018, A. Location in patent: Paragraph 0017-0028
[2] Patent: CN106187989, 2016, A. Location in patent: Paragraph 0016
[3] Acta Chemica Scandinavica, 1996, vol. 50, # 2, p. 170 - 177
[4] Journal of the Chemical Society, Chemical Communications, 1983, # 23, p. 1392 - 1394
[5] Molecules, 2005, vol. 10, # 9, p. 1169 - 1178