Diethyl sulfate

Schwefelsäurediethylester

Colorless liquid with ester type odor

Liquid

1.18 g · cm -3 ( 25 ° C)

-24 ° C

208 ° C ( with decomposition)

16 Pa ( 20 ° C)

• Slightly soluble in water (7 g · l-1 at 20 ° C) with slow hydrolysis
• Miscible with ethanol, ether, and most polar organic solvents

1.3989 (20 ° C)

Risk

No MAK, since carcinogenic

• 880 mg · kg -1 ( LD50, rat, oral)
• 706 mg · kg -1 ( LD50, Rabbit, transdermal)
• 647 mg · kg -1 ( LD50, mouse, oral)

Template: Infobox chemical / molecular formula search available

Diethyl sulfate is a toxic, colorless, oily liquid with a characteristic peppermint odor.

Properties

The colorless substance is a liquid at room temperature, but little volatile. Diethyl sulfate dissolves slightly in water, it slowly hydrolyzed to form sulfuric acid and ethanol. In hot water, this reaction is much faster. Ethanol, ether, and most polar organic solvents miscible diethyl.

Use

Diethyl sulfate is used for the alkylation of phenols, amines, and thiols.

Production

Diethyl sulfate may be prepared in the laboratory at 20 to 35 ° C with good yield from sulfuryl chloride and excess of absolute ethanol in the presence of a base:

Industrially, however, diethyl sulfate of ethene and fuming sulfuric acid is extracted under pressure and cooling:

The crude product is purified by vacuum distillation.

Safety

Diethyl sulfate is toxic and is corrosive. Skin contact causes severe burns. Inhalation may lead to pulmonary edema. In animal experiments the substance to be carcinogenic to humans, there is a reasonable suspicion of carcinogenicity. The substance is classified as very dangerous carcinogenic substance in Annex II, No. 6 of the Hazardous Substances Ordinance ( Ordinance on Hazardous Substances ) and may be produced or used in closed systems.

The liquid evaporates, so as to form to a volume fraction of 12% explosive mixtures with air.

The substance is indeed flammable, but very difficult to ignite due to the low vapor pressure.