Ethylamine
Encyclopedia
Ethylamine is an organic compound
with the formula
CH3CH2NH2. This colourless gas has a strong ammonia
-like odor. It is miscible
with virtually all solvents and is considered to be a weak base
, as is typical for amine
s. Ethylamine is widely used in chemical industry and organic synthesis
.
and ammonia
are combined in the presence of an oxide catalyst:
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
.
Ethylamine can be prepared by several other routes, but these are not economical. Ethylene
and ammonia
combine to give ethylamine in the presence of an sodium amide
or related basic catalysts.
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
.
and protonation
. Reaction with sulfuryl chloride
followed by oxidaton 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
. Evaporation of these solutions, gives back lithium metal. Such solutions are used for the reduction
of unsaturated organic compounds, such as naphthalene
s and alkynes.
Ethylamine is a precursor to many herbicides including atrazine
and simazine
. It is found in rubber products as well.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
CH3CH2NH2. This colourless gas has a strong ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
-like odor. It is miscible
Miscibility
Miscibility is the property of liquids to mix in all proportions, forming a homogeneous solution. In principle, the term applies also to other phases , but the main focus is usually on the solubility of one liquid in another...
with virtually all solvents and is considered to be a weak base
Base (chemistry)
For the term in genetics, see base A base in chemistry is a substance that can accept hydrogen ions or more generally, donate electron pairs. A soluble base is referred to as an alkali if it contains and releases hydroxide ions quantitatively...
, as is typical for amine
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
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 molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
.
Synthesis
Ethylamine is produced on a large scale by two processes. Most commonly ethanolEthanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
and ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
are combined in the presence of an oxide catalyst:
- CH3CH2OH + NH3 → CH3CH2NH2 + H2O
In this reaction, ethylamine is coproduced together with diethylamine
Diethylamine
Diethylamine is a secondary amine with the molecular structure CH3CH2NHCH2CH3. It is a flammable, strongly alkaline liquid. It is miscible with water and ethanol. It is a colorless liquid which often appears brown due to impurities...
and triethylamine
Triethylamine
Triethylamine is the chemical compound with the formula N3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine, for which TEA is also a common abbreviation....
. 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 form of amination that involves the conversion of a carbonyl group to an amine via an intermediate imine...
of acetaldehyde
Acetaldehyde
Acetaldehyde is an organic chemical compound with the formula CH3CHO or MeCHO. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale industrially. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants as part...
.
- CH3CHO + NH3 + H2 → CH3CH2NH2 + H2O
Ethylamine can be prepared by several other routes, but these are not economical. Ethylene
Ethylene
Ethylene is a gaseous organic compound with the formula . It is the simplest alkene . Because it contains a carbon-carbon double bond, ethylene is classified as an unsaturated hydrocarbon. Ethylene is widely used in industry and is also a plant hormone...
and ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
combine to give ethylamine in the presence of an sodium amide
Sodium amide
Sodium amide, commonly called sodamide, is the chemical compound with the 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 catalysts.
- H2C=CH2 + NH3 → CH3CH2NH2
Hydrogenation of acetonitrile
Acetonitrile
Acetonitrile is the chemical compound with formula . This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture...
, acetamide
Acetamide
Acetamide 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...
, and 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. Pure nitroethane is colourless and has a fruity odor.- Preparation :...
affords ethylamine
Ethylamine
Ethylamine is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It is miscible with virtually all solvents and is considered to be a weak base, as is typical for amines. Ethylamine is widely used in chemical industry and organic...
. These reactions can be effected stoichiometrically using lithium aluminium hydride
Lithium aluminium hydride
Lithium aluminium hydride, commonly abbreviated to LAH or known as LithAl, is an inorganic compound with the chemical formula LiAlH4. It was discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters,...
. In another route, ethylamine can be synthesized via nucleophilic substitution
Nucleophilic substitution
In organic and inorganic chemistry, nucleophilic substitution is a fundamental class of reactions in which an electron nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms called the leaving group; the positive or partially positive...
of a haloethane (such as chloroethane
Chloroethane
Chloroethane or monochloroethane, commonly known by its old name ethyl chloride, is a chemical compound with chemical formula , once widely used in producing tetraethyllead, 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.-Preparation:...
) with ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
, utilizing a strong base such as potassium hydroxide
Potassium hydroxide
Potassium hydroxide is an inorganic compound with the formula KOH, commonly called caustic potash.Along with sodium hydroxide , this colorless solid is a prototypical strong base. It has many industrial and niche applications. Most applications exploit its reactivity toward acids and its corrosive...
. 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. It is miscible with water and ethanol. It is a colorless liquid which often appears brown due to impurities...
and triethylamine
Triethylamine
Triethylamine is the chemical compound with the formula N3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine, for which TEA is also a common abbreviation....
.
- CH3CH2Cl + NH3 + KOH → CH3CH2NH2 + KCl + H2O
Reactions and applications
Ethylamine undergoes the reactions anticipated for a primary alkyl amine, such as acylationAcylation
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. Some classic examples include*the protonation of water by sulfuric acid:*the protonation of isobutene in the formation of a carbocation:2C=CH2 + HBF4 → 3C+ + BF4−*the protonation of ammonia in the...
. Reaction with sulfuryl chloride
Sulfuryl chloride
Sulfuryl chloride is an inorganic compound with the formula SO2Cl2. At room temperature, it is a colorless liquid with a pungent odor. Sulfuryl chloride is not found in nature, as can be inferred from its rapid hydrolysis....
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. The general formula is RSO2NH2, where R is some organic group. For example, "methanesulfonamide" is CH3SO2NH2...
give diethyldiazene
Diazene
Diazene, also called diimine or diimide, is a compound having the formula 2. It exists as two geometric isomers, E and Z. Diazene is also the parent member of the entire class of azo compounds with the formula 2, where R is an organyl group...
, EtN=NEt. Ethylamine may be oxidized using a strong oxidizer such as potassium permanganate
Potassium permanganate
Potassium permanganate is an inorganic chemical compound with the formula KMnO4. It is a salt consisting of K+ and MnO4− ions. Formerly known as permanganate of potash or Condy's crystals, it is a strong oxidizing agent. It dissolves in water to give intensely purple solutions, the...
to form acetaldehyde
Acetaldehyde
Acetaldehyde is an organic chemical compound with the formula CH3CHO or MeCHO. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale industrially. Acetaldehyde occurs naturally in coffee, bread, and ripe fruit, and is produced by plants as part...
.
Ethylamine like some other small primary amines is a good solvent for lithium
Lithium
Lithium is a soft, silver-white metal that belongs to the alkali metal group of chemical elements. It is represented by the symbol Li, and it has the atomic number 3. Under standard conditions it is the lightest metal and the least dense solid element. Like all alkali metals, lithium is highly...
metal, giving the ion
Ion
An ion is an atom or molecule in which the total number of electrons is not equal to the total number of protons, giving it a net positive or negative electrical charge. The name was given by physicist Michael Faraday for the substances that allow a current to pass between electrodes in a...
[Li(amine)4]+ and the solvated electron
Solvated electron
A solvated electron is a free electron in a solution. Solvated electrons occur widely although they are often not observed directly. The deep colour of solutions of alkali metals in ammonia arises form the presence of solvated electrons: blue when dilute and copper-colored when more concentrated...
. Evaporation of these solutions, gives back lithium metal. Such solutions are used for the reduction
Birch reduction
The Birch Reduction is an organic reaction which is particularly useful in synthetic organic chemistry. The reaction was reported in 1944 by the Australian chemist Arthur Birch working in the Dyson Perrins Laboratory in the University of Oxford, building on earlier work by Wooster and Godfrey in...
of unsaturated organic compounds, such as naphthalene
Naphthalene
Naphthalene is an organic compound with formula . It is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of 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 widespread contamination in drinking water and its associations with birth defects and menstrual problems when consumed by humans at concentrations...
and simazine
Simazine
Simazine is a herbicide of the triazine class. The compound is used to control broad-leaved weeds and annual grasses.-Physical properties:* Water solubility: 5 mg/L at 20 °C...
. It is found in rubber products as well.
External links
- Safety data at www.inchem.org
- Safety MSDS data
- Atrazine News - an Atrazine specific news site