Ethylamine, also known as ethanamine, 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. Th ...

with the formula CH₃CH₂NH₂. This colourless gas has a strong

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 ...

-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

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent ...

s. Ethylamine is widely used in chemical industry and organic synthesis.

Synthesis

Ethylamine is produced on a large scale by two processes. Most commonly

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an alcohol with the chemical formula . Its formula can be also written as or (an ethyl group linked to a ...

and

are combined in the presence of an oxide

catalyst Catalysis () is the process of increasing the rate of a chemical reaction by adding a substance known as a catalyst (). Catalysts are not consumed in the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recyc ...

: :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.Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke, "Amines, Aliphatic" Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. 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

combine to give ethylamine in the presence of a sodium amide or related basic

s. :H₂C=CH₂ + NH₃ → CH₃CH₂NH₂ Hydrogenation of acetonitrile,

acetamide Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is the simplest amide derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent. The related compound ''N'',''N''-dime ...

, 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 Bromoethane, also known as ethyl bromide, is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr (which is also used as an abbreviation for ethidium bromide). This volatile compound has an ether-like odor. Prepar ...

) with

, utilizing a strong base such as

potassium hydroxide Potassium hydroxide is an inorganic compound with the formula K OH, and is commonly called caustic potash. Along with sodium hydroxide (NaOH), KOH is a prototypical strong base. It has many industrial and niche applications, most of which exp ...

. 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 In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated, like hexane ...

amines, ethylamine is a weak base: the pK_a of H₃CH₂NH₃sup>+ has been determined to be 10.8 Ethylamine undergoes the reactions anticipated for a primary alkyl amine, such as acylation and

protonation In chemistry, protonation (or hydronation) is the adding of a proton (or hydron, or hydrogen cation), (H+) to an atom, molecule, or ion, forming a conjugate acid. (The complementary process, when a proton is removed from a Brønsted–Lowry acid ...

. Reaction with sulfuryl chloride followed by oxidation of the sulfonamide give diethyl diazene, 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 Lithium (from el, λίθος, lithos, lit=stone) is a chemical element with the symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard conditions, it is the least dense metal and the least dense soli ...

metal, giving the ion i(amine)₄sup>+ 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 Atrazine is a chlorinated herbicide of the triazine class. It is used to prevent pre-emergence broadleaf weeds in crops such as maize (corn), soybean and sugarcane and on turf, such as golf courses and residential lawns. Atrazine's primary m ...

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 ketamine which is missing the 2-chloro group on the phenyl ring, and its N-ethyl analog) which are closely related to the well known anesthetic agent

ketamine Ketamine is a dissociative anesthetic used medically for induction and maintenance of anesthesia. It is also used as a recreational drug. It is one of the safest anesthetics, as, in contrast with opiates, ether, and propofol, it suppress ...

and the recreational drug phencyclidine and have been detected on the black market, being marketed for use as a recreational hallucinogen and tranquilizer. This produces a cyclidine with the same mechanism of action as ketamine (

NMDA receptor antagonism NMDA receptor antagonists are a class of drugs that work to antagonize, or inhibit the action of, the ''N''-Methyl-D-aspartate receptor (NMDAR). They are commonly used as anesthetics for animals and humans; the state of anesthesia they induce ...

) but with a much greater potency at the PCP binding site, a longer half-life, and significantly more prominent parasympathomimetic effects.

References

External links

Safety data at www.inchem.org

{{Authority control Alkylamines Organic compounds with 2 carbon atoms