roger2003 (Newbee)
02-14-03 10:37
No 407679
      Preparation of Dietyl Sulfate  Bookmark   

Merck Index 13th

Monograph Number:  3156
Title:  Diethyl Sulfate
CAS Registry Number:  64-67-5
CAS Name:  Sulfuric acid diethyl ester
Molecular Formula:  C4H10O4S
Molecular Weight:  154.19. 
Percent Composition:  C 31.16%, H 6.54%, O 41.50%, S 20.80%
Line Formula:  (C2H5)2SO4
Literature 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).
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:  220F.  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).
Melting point:  mp -25
Boiling point:  bp 209.5 with decompn; bp15 96; bp5 75
Flash point:  Flash pt:  220F
Index of refraction:  nD20 1.40037, A. I. Vogel, D. M. Cowan, J. Chem. Soc. 1943, 16
Density:  d423 1.1774
Toxicity data:  LD50 orally in rats:  0.88 g/kg (Smyth)
NOTE:  This substance is reasonably anticipated to be a human carcinogen:  Ninth Report on Carcinogens (PB2000-107509, 2000) p III-115.
Use:  Chiefly as an ethylating agent; as an accelerator in the sulfation of ethylene; in some sulfonations.

Other References:

../rhodium/chemistry /diethylsulfate.html     =   JACS 46, 999-1001 (1924)

Patent DE272339:
Patent GB215000:
Patent US1885585:
Patent US1919618
Patent US2474588:

I`m looking for all references about dietylsulfate from Ullmann etc.