Triethylamine is the

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...

N(CH₂CH₃)₃, commonly abbreviated Et₃N. Like

triethanolamine Triethanolamine, or TEOA, is an organic compound with the chemical formula . It is a colourless, viscous liquid. It is both a tertiary amine and a triol. A triol is a molecule with three alcohol groups. Approximately 150,000 tonnes were produ ...

and the

tetraethylammonium Tetraethylammonium (TEA) is a quaternary ammonium cation with the chemical formula , consisting of four ethyl groups (, denoted Et) attached to a central nitrogen atom. It is a counterion used in the research laboratory to prepare lipophilic salt ...

ion, it is often abbreviated TEA. It is a colourless volatile liquid with a strong fishy odor reminiscent of

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

. Like

diisopropylethylamine ''N'',''N''-Diisopropylethylamine, or Hünig's base, is an organic compound that is a tertiary amine. It is named after the German chemist . It is used in organic chemistry as a non-nucleophilic base. It is commonly abbreviated as DIPEA, DIEA, ...

(Hünig's base), triethylamine is commonly employed in

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

, usually as a base.

Synthesis and properties

Triethylamine is prepared by the

alkylation Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

of ammonia with

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

: :NH₃ + 3 C₂H₅OH → N(C₂H₅)₃ + 3 H₂O The pK_a of protonated triethylamine is 10.75,David Evans Research Group
and it can be used to prepare buffer solutions at that pH. The

hydrochloride In chemistry, a hydrochloride is an acid salt resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (e.g. an amine). An alternative name is chlorhydrate, which comes from French. An archaic alternati ...

salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...

, triethylamine hydrochloride (triethylammonium chloride), is a colorless, odorless, and

hygroscopic Hygroscopy is the phenomenon of attracting and holding water molecules via either absorption (chemistry), absorption or adsorption from the surrounding Natural environment, environment, which is usually at normal or room temperature. If water mol ...

powder, which decomposes when heated to 261 °C. Triethylamine is soluble in water to the extent of 112.4 g/L at 20 °C. It is also miscible in common organic solvents, such as acetone, ethanol, and diethyl ether. Laboratory samples of triethylamine can be purified by distilling from

calcium hydride Calcium hydride is the chemical compound with the formula , an alkaline earth hydride. This grey powder (white if pure, which is rare) reacts vigorously with water, liberating hydrogen gas. is thus used as a drying agent, i.e. a desiccant. is ...

. In alkane solvents triethylamine is a

Lewis base A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any sp ...

that forms adducts with a variety of Lewis acids, such as I₂ and

phenols In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of one or more hydroxyl groups (− O H) bonded directly to an aromatic hydrocarbon group. The simplest is phenol, . Phenolic compounds ar ...

. Owing to its steric bulk, it forms complexes with transition metals reluctantly.

Applications

Triethylamine is commonly employed in organic synthesis as a base. For example, it is commonly used as a base during the preparation of

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

s and

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...

s from

acyl chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example o ...

s. Such reactions lead to the production of

hydrogen chloride The Chemical compound, compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colorless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hyd ...

which combines with triethylamine to form the salt triethylamine hydrochloride, commonly called triethylammonium chloride. (R, R' =

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl group is derived from a cy ...

aryl In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used ...

): :R₂NH + R'C(O)Cl + Et₃N → R'C(O)NR₂ + Et₃NH⁺Cl⁻ Like other tertiary amines, it catalyzes the formation of urethane foams and epoxy resins. It is also useful in

dehydrohalogenation In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate (chemistry), substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogen ...

reactions and

Swern oxidation In organic chemistry, the Swern oxidation also known as Moffatt-Swern, named after Daniel Swern, is a chemical reaction whereby a primary or secondary Alcohol (chemistry), alcohol () is redox, oxidized to an aldehyde () or ketone () using oxalyl ...

s. Triethylamine is readily alkylated to give the corresponding

quaternary ammonium salt In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure , where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion () and the primary, secondary, ...

: :RI + Et₃N → Et₃NR⁺I⁻ Triethylamine is mainly used in the production of

quaternary ammonium compounds In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure , where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion () and the primary, secondary, o ...

for textile auxiliaries and quaternary ammonium salts of

dye Juan de Guillebon, better known by his stage name DyE, is a French musician. He is known for the music video of the single "Fantasy Fantasy is a genre of speculative fiction that involves supernatural or Magic (supernatural), magical ele ...

s. It is also a

catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

and acid neutralizer for

condensation reaction In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a ...

s and is useful as an intermediate for manufacturing medicines,

pesticide Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for approximately 50% of all p ...

s and other chemicals. Triethylamine salts, like any other tertiary ammonium salts, are used as an ion-interaction reagent in ion interaction chromatography, due to their amphiphilic properties. Unlike quaternary ammonium salts, tertiary ammonium salts are much more volatile, therefore

mass spectrometry Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a ''mass spectrum'', a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is used ...

can be used while performing analysis.

Niche uses

Triethylamine is commonly used in the production of anionic

Polyurethane dispersion Polyurethane dispersion, or PUD, is understood to be a polyurethane polymer resin dispersed in water, rather than a solvent, although some cosolvent may be used. Its manufacture involves the synthesis of polyurethanes having carboxylic acid functi ...

s (resins dispersed in water rather than solvents) as a neutralizing agent. Triethylamine is used to give salts of various carboxylic acid-containing pesticides, e.g.

Triclopyr Triclopyr (3,5,6-trichloro-2-pyridinyloxyacetic acid) is an organic compound in the pyridine group that is used as a systemic foliar herbicide and fungicide. History Triclopyr triethylammonium (TEA) was first registered in 1979 in the United ...

and

2,4-dichlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic acid is an organic compound with the chemical formula . It is usually referred to by its ISO common name 2,4-D. It is a systemic herbicide that kills most broadleaf weeds by causing uncontrolled growth, but most gra ...

. Triethylamine is the active ingredient in FlyNap, a product for anesthetizing fruit flies. It is also used in mosquito and vector control labs to anesthetize mosquitoes. This is done to preserve any viral material that might be present during species identification. The

bicarbonate In inorganic chemistry, bicarbonate (IUPAC-recommended nomenclature: hydrogencarbonate) is an intermediate form in the deprotonation of carbonic acid. It is a polyatomic anion with the chemical formula . Bicarbonate serves a crucial bioche ...

of triethylamine (often abbreviated TEAB, triethylammonium bicarbonate) is useful in reverse phase chromatography, often in a gradient to purify nucleotides and other biomolecules. Triethylamine was discovered by the Germans during the early 1940s to be

hypergolic A hypergolic propellant is a rocket propellant combination used in a rocket engine, whose components spontaneously ignite when they come into contact with each other. The two propellant components usually consist of a fuel and an oxidizer. The ...

in combination with nitric acid, and was used as a component in the German

Wasserfall The ("Waterfall remote-controlled anti-aircraft rocket") was a German guided supersonic surface-to-air missile project of World War II. Development was not completed before the end of the war and it was not used operationally. The system was ...

rocket. The Soviet

Scud missile A Scud missile is one of a series of tactical ballistic missiles developed by the Soviet Union during the Cold War. It was exported widely to both Second and Third World countries. The term comes from the NATO reporting name attached to the m ...

used TG-02, a mixture of 50%

xylidine Xylidine can refer to any of the six isomers of xylene amine, or any mixture of them. The chemical formula of xylidines is C8H11N or, more descriptively, (CH3)2C6H3NH2. The CAS number for the isomer mixture is 1300-73-8. They are colorless solids ...

and 50% triethylamine as a starting fluid to ignite its rocket engine.

Natural occurrence

Hawthorn flowers have a heavy, complicated scent, the distinctive part of which is triethylamine, which is also one of the first chemicals produced by a dead human body when it begins to decay. Due to the scent, it is considered unlucky in

British culture The culture of the United Kingdom is influenced by its History of the United Kingdom, combined nations' history, its interaction with the cultures of Europe, the individual diverse cultures of England, Wales, Scotland and Northern Ireland, and ...

to bring hawthorn into a house.

Gangrene Gangrene is a type of tissue death caused by a lack of blood supply. Symptoms may include a change in skin color to red or black, numbness, swelling, pain, skin breakdown, and coolness. The feet and hands are most commonly affected. If the ga ...

and

semen Semen, also known as seminal fluid, is a bodily fluid that contains spermatozoon, spermatozoa which is secreted by the male gonads (sexual glands) and other sexual organs of male or hermaphrodite, hermaphroditic animals. In humans and placen ...

are also said to possess a similar odour.The book of general ignorance. John Lloyd & John Mitchinson. Faber & Faber 2006
The Hawthorn
BBC

References

External links