| Chemical Properties | 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). |
| Uses | 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). |
| Application | 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]. |
| Definition | 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. |
| Preparation | Diethyl sulfate is produced from ethanol and sulfuric acid, from ethylene and sulfuric acid, or from diethyl ether and fuming sulfuric acid (Budavari, 1996). |
| General Description | 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. |
| Air & Water Reactions | Highly flammable. Slowly reacts with water to form ethyl alcohol, a flammable liquid, and ethyl sulfate, with eventual conversion to sulfuric acid. |
| Reactivity Profile | 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)]. |
| Health Hazard | 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.] |
