3130. Diethyl Sulfate

Nomenclature

CAS number: 64-67-5
Sulfuric acid diethyl ester.
C4H10O4S; mol wt 154.18.
C 31.16%, H 6.54%, O 41.51%, S 20.80%.

Description and references

Prepd from ethanol + sulfuric acid; by absorption of ethylene in sulfuric acid; from diethyl ether and fuming sulfuric acid. Review of prepn and uses: R. Page, J. A. John in Ethylene and its Industrial Derivatives S. A. Miller, Ed. (Benn, London, 1969) pp 774-787. Toxicity data: H. F. Smyth et al., J. Ind. Hyg. Toxicol. 31, 60 (1949). Review of carcinogenicity studies: IARC Monographs 4, 277-281 (1974). Reviews: C. M. Suter, The Organic Chemistry of Sulfur (John Wiley, 1944) pp 62-65; E. E. Gilbert, Sulfonation and Related Reactions (Interscience, New York, 1965).

Chemical structure

Properties

Colorless, oily liquid; peppermint odor. Poisonous. Darkens with age. bp 209.5° with decompn; bp15 96°; bp5 75°. mp -25°. d423 1.1774. nD20 1.40037, A. I. Vogel, D. M. Cowan, J. Chem. Soc. 1943, 16. Flash pt: 220°F. Vapor density (air = 1) 5.31. Vapor pressure at 47° = 1 mm. Practically insol in water, gradually dec by it. Rapidly dec by hot water into monoethyl sulfate and alcohol. Miscible with alcohol, ether. LD50 orally in rats: 0.88 g/kg (Smyth).

Caution

This substance is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-97.

Use

Chiefly as an ethylating agent; as an accelerator in the sulfation of ethylene; in some sulfonations.