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Diethyl sulfate is a colorless, oily liquid with a faint peppermint- like odor, which darkens with age (Budavari, 1996). It is miscible with alcohol and ether (O'Neil, 2006). At higher temperatures, DES rapidly decomposes into monoethyl sulfate and alcohol (NTP, 2011).

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The primary use of diethyl sulfate is as a chemical intermediate (ethylating agent) in synthesis of ethyl derivatives of phenols, amines, and thiols; as an accelerator in the sulfation of ethylene; and in some sulfonation processes. It is used to manufacture dyes, pigments, carbonless paper, and textiles. It is an intermediate in the indirect hydration (strong acid) process for the preparation of synthetic ethanol from ethylene. Smaller quantities are used in household products, cosmetics, agricultural chemicals, pharmaceuticals, and laboratory reagents (IARC 1992, 1999, HSDB 2009). In 1966, it was used as a mutagen to create the Luther variety of barley (IARC 1974).

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Diethyl sulfate can be used as a reactant for the synthesis of:
Biologically active compounds such as bispyrazole, pyrazolopyrimidine and pyridine containing antipyrinyl moieties.
N-substituted-2-styryl-4(3H)-quinazolinones.
Ionic liquids with pyrrolidinium, piperidinium and morpholinium cations, having potential applications as electrolytes.
It can also be used as an alkylating agent to synthesize 1-alkyl/aralkyl-2-(1-arylsufonylalkyl)benzimidazoles and an ionic liquid ethylmethylimidazole ethylsulfate ([EMIM][EtSO4].

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Diethyl sulfate is produced from ethanol and sulfuric acid, from ethylene and sulfuric acid, or from diethyl ether and fuming sulfuric acid (Budavari, 1996).

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ChEBI: Diethyl sulfate is the diethyl ester of sulfuric acid. It has a role as a carcinogenic agent, an apoptosis inducer, an alkylating agent and a mutagen.

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Diethyl sulfate appears as a clear colorless liquid with a peppermint odor. Burns, though may be difficult to ignite. Corrosive to metals and tissue. It is a potent alkylating agent.

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Highly flammable. Slowly reacts with water to form ethyl alcohol, a flammable liquid, and ethyl sulfate, with eventual conversion to sulfuric acid.

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The presence of moisture in a metal container of Diethyl sulfate caused the formation of sulfuric acid which reacts with the metal to release hydrogen which pressurized and exploded the container [Chem. Abst. 28:2908(1934)].

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May be fatal if inhaled, swallowed or absorbed through skin. Inhalation causes nausea and vomiting. Causes burns to skin and eyes. Ingestion may cause nausea, vomiting abdominal pain and collapse.

Safety Profile

Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Poison by inhalation and subcutaneous routes. Moderately toxic by ingestion and sktn contact. A severe skin irritant. An experimental teratogen. Mutation data reported. Combustible when exposed to heat or flame; can react with oxidzing materials. Moisture causes liberation of H2SO4. Violent reaction with potassium tert-butoxide. Reacts violently with 3,8-dnitro-6-phenylphenanthridine + water. Reaction with iron + water forms explosive hydrogen gas. To fight fire, use alcohol foam, H2O foam, CO2, dry chemicals. When heated to decomposition it emits toxic fumes of SOx. See also SULFATES.

Carcinogenicity

Diethyl sulfate is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.

Purification Methods

Wash the ester with aqueous 3% Na2CO3 (to remove acidic material), then distilled water, dry (CaCl2), filter and distil it in a vacuum. It is an ethylating agent and blisters the skin. [Beilstein 1 IV 1236.]

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