Ethylamine

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Ethylamine

Ethylamine is an organic compound

Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
with the formula

Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
CH₃CH₂NH₂. This colourless gas has a strong ammonia

Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
-like odor. It is miscible

Miscibility

Miscibility is a term commonly used in chemistry that refers to the property of liquids to mix in all proportions, forming a Homogeneity solution....
with virtually all solvents and is considered to be a weak base

Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
, as is typical for amine

Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
s. Ethylamine is widely used in chemical industry and organic synthesis

Organic synthesis

Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic_chemistry molecules can often contain a higher level of complexity compared to purely Inorganic_chemistry compounds, so the synthesis of organic compounds has developed into one of the most im...
.

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

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
and ammonia

Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
are combined in the presence of a oxide catalyst:

CH₃CH₂OH + NH₃ ? CH₃CH₂NH₂ + H₂O

In this reaction, ethylamine is coproduced together with diethylamine and triethylamine.

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Encyclopedia

Ethylamine is an organic compound

Organic compound

Chemical formula

Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
-like odor. It is miscible

Miscibility

Base (chemistry)

Amine

Organic synthesis

Synthesis

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

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatility , flammable, colorless liquid....
and ammonia

Ammonia

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

Reductive amination

Reductive amination is a chemical reaction which involves the conversion of a carbonyl group to an amine, via an intermediate imine. The carbonyl group is most commonly a ketone or an aldehyde....
of acetaldehyde

Acetaldehyde

Acetaldehyde is an organic compound with the chemical formula CarbonHydrogen3CHOxygen or MeCHO. It is a flammable liquid with a fruity smell....
.

CH₃CHO + NH₃ + H₂ → CH₃CH₂NH₂ + H₂O

Ethylamine can be prepared by several other routes, but these are not economical. Ethylene

Ethylene

Ethylene is the chemical compound with the formula C2H4. It is the simplest alkene. Because it contains a carbon-carbon double bond, ethylene is called an unsaturated hydrocarbon or an olefin....
and ammonia

Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
combine to give ethylamine in the presence of an sodium amide

Sodium amide

Sodium amide, commonly called sodamide, is the chemical compound with the chemical formula NaNH2. This solid, which is dangerously reactive toward water, is white when pure, but commercial samples are typically gray due to the presence of small quantities of metallic iron from the manufacturing process....
or related basic catalyst.

H₂C=CH₂ + NH₃ → CH₃CH₂NH₂

Hydrogenation of acetonitrile

Acetonitrile

Acetonitrile is the chemical compound with chemical formula CH3CN. This colourless liquid is the simplest organic nitrile and is widely used as a solvent....
, acetamide

Acetamide

Acetamide , CH3CONH2, the amide of acetic acid, is a white crystalline solid in pure form. It is produced by dehydration reaction ammonium acetate:...
, and nitroethane affords ethylamine. These reactions can be effected stoichiometrically using lithium aluminium hydride

Lithium aluminium hydride

Lithium aluminium hydride , commonly abbreviated to LAH, is a reducing agent used in organic synthesis. It is more powerful than the related reagent sodium borohydride due to the weaker Al-H bond compared to the B-H bond....
. In another route that is also instructive, ethylamine can be synthesized via nucleophilic substitution

Nucleophilic substitution

In organic chemistry and inorganic chemistry, nucleophilic substitution is a fundamental class of substitution reaction in which an "electron rich" nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom attached to a group or atom called the leaving group; the positive or partially positive atom...
of a haloethane (such as chloroethane

Chloroethane

Chloroethane or monochloroethane, commonly known by its old name ethyl chloride, is a chemical compound once widely used in producing tetra-ethyl lead, a gasoline additive....
or bromoethane

Bromoethane

Bromoethane, also known as ethyl bromide is a chemical compound of the haloalkanes group. It is abbreviated by chemists as EtBr. This volatile compound has an ether-like odour....
) with ammonia

Ammonia

Ammonia is a chemical compound with the chemical formula nitrogenhydrogen. It is normally encountered as a gas with a characteristic pungent odor....
, utilizing a strong base such as potassium hydroxide

Potassium hydroxide

Potassium hydroxide is the inorganic compound with the formula potassiumhydroxide. Along with sodium hydroxide, this colourless solid is a prototypical "strong base"....
. This method affords significant amounts of byproducts, including diethylamine

Diethylamine

Diethylamine is a secondary amine with the molecular structure CH3CH2NHCH2CH3. It is a flammable, strongly alkaline liquid....
and triethylamine

Triethylamine

Triethylamine is the chemical compound with the chemical formula N3, commonly abbreviated ethyl group3N or TEA. It is a commonly encountered in organic synthesis probably because it is the simplest symmetrically trisubstituted amine, i.e....
.

2 CH₃CH₂Cl + NH₃ + KOH ? CH₃CH₂NH₂ + KCl + H₂O

Reactions and applications

Ethylamine undergoes the reactions anticipated for a primary alkyl amine, such as acylation

Acylation

In chemistry, acylation is the process of adding an acyl group to a compound. The compound providing the acyl group is called the acylating agent....
and protonation

Protonation

In chemistry, protonation is the addition of a proton to an atom, molecule, or ion. Protonation is possibly the most fundamental chemical reaction and is a step in many stoichiometry and catalysis....
. Reaction with sulfuryl chloride

Sulfuryl chloride

Sulfuryl chloride is SO2Cl2, a compound composed of sulfur, oxygen, and chlorine. At room temperature, it is a colorless liquid with a pungent odor....
followed by oxidaton of the sulfonamide

Sulfonamide (chemistry)

In chemistry, the sulfonamide functional group is -S2-NH2, a sulfonyl group connected to an amine group.A sulfonamide is a compound that contains this group....
give diethyldiazene

Diazene

Diazene, also called diimine or diimide, is a compound having the formula HN=NH. Azo compounds can be considered to be formally derived from diazene by substituting the hydrogen atoms with...
, EtN=NEt. Ethylamine may be oxidized using a strong oxidizer such as potassium permanganate

Potassium permanganate

Potassium permanganate is the inorganic chemical compound potassiummanganeseoxygen4, a water soluble salt consisting of equal Mole amounts of potassium and permanganate ions....
to form nitroethane

Nitroethane

Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure....
.

Ethylamine like some other small primary amines is a good solvent for lithium

Lithium

Lithium is a chemical element with the symbol Li and atomic number 3. It is a soft alkali metal with a silver-white color. Under standard conditions for temperature and pressure, it is the lightest metal and the least dense solid element....
metal, giving the ion

Ion

An ion is an atom or molecule which has lost or gained one or more electrons, giving it a positive or negative electrical charge. According to the Bohr_model this will be from or in the outer shield 'n'....
[Li(amine)₄]⁺ and the solvated electron

Solvated electron

A solvated electron is a free electron in a solution. Solvated electrons are widely occurring and are commonly proposed for reactions that occur in water ....
. Evaporation of these solutions, gives back lithium metal. Such solutions are used for the reduction

Birch reduction

The Birch reduction is the organic reduction of Aromatic_ring with sodium and an alcohol in liquid ammonia to form 1,4-Cyclohexadiene . The reaction was reported by the Australian chemist Arthur John Birch in 1944....
of unsaturated organic compounds, such as naphthalene

Naphthalene

Naphthalene, also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or antimite and not to be confused with naphtha, is a crystalline, Aromaticity, white, solid hydrocarbon with formula Carbon10hydrogen8 and the structure of two fused benzene rings....
s and alkynes.

Ethylamine is a precursor to many herbicides including atrazine

Atrazine

Atrazine, 2-chloro-4--6--s-triazine, an organic compound consisting of an s-triazine-ring is a widely used herbicide. Its use is controversial due to its effects on nontarget species, such as on amphibians....
and simazine

Simazine

Simazine is an herbicide of the triazine class. The compound is used to control broad-leaved weeds and Annual plant grasses....
. It is found in rubber products as well.

Ethylamine

Synthesis

Reactions and applications

External links