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 nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis. Synthesis Ethylamine is produced on a large scale by two processes. Most commonly ethanol and ammonia are combined in the presence of an oxide catalyst: CH3CH2OH + NH3 → CH3CH2NH2 + H2O In this reaction, ethylamine is coproduced together with diethylamine and triethylamine. In aggregate, approximately 80M kilograms/year of these three amines are produced industrially. It is also produced by reductive amination of acetaldehyde. CH3CHO + NH3 + H2 → CH3CH2NH2 + H2O Ethylamine can be prepared by several other routes, but these are not economical. Ethylene and ammonia combine to give ethylamine in the presence of a sodium amide or related basic catalysts. H2C=CH2 + NH3 → CH3CH2NH2 Hydrogenation of acetonitrile, acetamide, and nitroethane affords ethylamine. These reactions can be effected stoichiometrically using lithium aluminium hydride. In another route, ethylamine can be synthesized via nucleophilic substitution of a haloethane (such as chloroethane or bromoethane) with ammonia, utilizing a strong base such as potassium hydroxide. This method affords significant amounts of byproducts, including diethylamine and triethylamine. CH3CH2Cl + NH3 + KOH → CH3CH2NH2 + KCl + H2O Ethylamine is also produced naturally in the cosmos; it is a component of interstellar gases. Reactions Like other simple aliphatic amines, ethylamine is a weak base: the pKa of [CH3CH2NH3]+ has been determined to be 10.8 Ethylamine undergoes the reactions anticipated for a primary alkyl amine, such as acylation and protonation. Reaction with sulfuryl chloride followed by oxidation of the sulfonamide give diethyldiazene, EtN=NEt. Ethylamine may be oxidized using a strong oxidizer such as potassium permanganate to form acetaldehyde. Ethylamine like some other small primary amines is a good solvent for lithium metal, giving the ion [Li(amine)4]+ and the solvated electron. Such solutions are used for the reduction of unsaturated organic compounds, such as naphthalenes and alkynes. Applications Ethylamine is a precursor to many herbicides including atrazine and simazine. It is found in rubber products as well. Ethylamine is used as a precursor chemical along with benzonitrile (as opposed to o-chlorobenzonitrile and methylamine in ketamine synthesis) in the clandestine synthesis of cyclidine dissociative anesthetic agents (the analogue of