Diethylamine is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The s ...

with the formula (CH₃CH₂)₂NH. It is a secondary amine. It is a flammable, weakly alkaline liquid that is

miscible Miscibility () is the property of two substances to mix in all proportions (that is, to fully dissolve in each other at any concentration), forming a homogeneous mixture (a solution). The term is most often applied to liquids but also applie ...

with most solvents. It is a colorless liquid, but commercial samples often appear brown due to impurities. It has a strong ammonia-like odor.

Production and uses

Diethylamine is made by the alumina-catalyzed reaction of ethanol and

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous w ...

. It is obtained together with

ethylamine Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucl ...

and

triethylamine Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA ...

. Annual production of three ethylamines was estimated in 2000 to be 80,000,000 kg. It is used in the production of corrosion inhibitor ''N'',''N''- diethylaminoethanol, by reaction with

ethylene oxide Ethylene oxide is an organic compound with the formula . It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintl ...

. It is also a precursor to a wide variety of other commercial products. Diethylamine is also sometimes used in the illicit production of

LSD Lysergic acid diethylamide (LSD), also known colloquially as acid, is a potent psychedelic drug. Effects typically include intensified thoughts, emotions, and sensory perception. At sufficiently high dosages LSD manifests primarily mental, vi ...

Supramolecular structure

Diethylamine is the smallest and simplest molecule that features a supramolecular

helix A helix () is a shape like a corkscrew or spiral staircase. It is a type of smooth space curve with tangent lines at a constant angle to a fixed axis. Helices are important in biology, as the DNA molecule is formed as two intertwined helices ...

as its lowest energy aggregate. Other similarly sized

hydrogen-bonding In chemistry, a hydrogen bond (or H-bond) is a primarily electrostatic force of attraction between a hydrogen (H) atom which is covalently bound to a more electronegative "donor" atom or group (Dn), and another electronegative atom bearing a ...

molecules favor cyclic structures.

Safety

Diethylamine has low toxicity, but the vapor causes transient impairment of vision.

References

{{Reflist

External links

Hazardous Substance Fact Sheet
Alkylamines