Triethylamine: Difference between revisions

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{{Short description|A chemical compound used as a base in organic synthesis}}
{{DISPLAYTITLE:Triethylamine}}
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'''Triethylamine''' (TEA) is a chemical compound with the formula (C<sub>2</sub>H<sub>5</sub>)<sub>3</sub>N. It is a tertiary amine and is commonly used in organic synthesis as a base. Triethylamine is a colorless, volatile liquid with a strong fishy odor reminiscent of ammonia.
== Triethylamine ==
[[File:Et3N_showing_pyramidal-ness.svg|thumb|right|Structural formula of triethylamine]]


==Structure and properties==
'''Triethylamine''' (TEA) is a [[tertiary amine]] with the chemical formula (C<sub>2</sub>H<sub>5</sub>)<sub>3</sub>N. It is a colorless, volatile liquid with a strong fishy odor reminiscent of [[ammonia]]. Triethylamine is commonly used in [[organic synthesis]] as a [[base (chemistry)|base]] and a [[catalyst]].
Triethylamine is a tertiary amine with a pyramidal molecular geometry. The nitrogen atom is sp<sup>3</sup> hybridized, and the molecule has a trigonal pyramidal shape. The C-N-C bond angles are approximately 109.5 degrees, typical of sp<sup>3</sup> hybridization.


Triethylamine is miscible with most organic solvents and is often used as a solvent itself. and a melting point of . The compound is flammable and should be handled with care.
== Structure and Properties ==
Triethylamine is a [[pyramidal molecule]], as depicted in the structural formula. The nitrogen atom is bonded to three ethyl groups, and the lone pair of electrons on the nitrogen contributes to the molecule's basicity. The [[molecular geometry]] around the nitrogen is trigonal pyramidal, which is typical for amines.


==Synthesis==
Triethylamine has a [[boiling point]] of 89.5 °C and a [[melting point]] of -114.7 °C. It is miscible with most organic solvents and is often used in [[chemical reactions]] that require a non-aqueous environment.
Triethylamine is typically synthesized by the alkylation of ammonia with ethanol in the presence of a catalyst. The reaction proceeds as follows:


: 3 C<sub>2</sub>H<sub>5</sub>OH + NH<sub>3</sub> _ (C<sub>2</sub>H<sub>5</sub>)<sub>3</sub>N + 3 H<sub>2</sub>O
== Uses ==
Triethylamine is widely used in the [[pharmaceutical industry]] and in the production of [[pesticides]], [[herbicides]], and other [[agrochemicals]]. It serves as a [[proton acceptor]] in various [[chemical reactions]], including the [[deprotonation]] of [[carboxylic acids]] and the formation of [[amide]] bonds.


This process can be carried out in a continuous flow reactor to improve efficiency and yield.
In [[organic chemistry]], triethylamine is often employed as a [[base]] in [[nucleophilic substitution]] reactions and [[esterification]] processes. It is also used in the [[synthesis]] of [[quaternary ammonium compounds]].


==Applications==
== Safety and Handling ==
Triethylamine is widely used in organic synthesis as a base. It is often employed in the preparation of esters and amides from acyl chlorides. It is also used in the synthesis of quaternary ammonium compounds and as a catalyst in the production of polyurethanes.
Triethylamine is a [[flammable liquid]] and should be handled with care. It can cause irritation to the [[skin]], [[eyes]], and [[respiratory tract]]. Proper [[personal protective equipment]] (PPE) such as gloves and goggles should be worn when handling this chemical.


In the pharmaceutical industry, triethylamine is used as a reagent in the synthesis of various drugs. It is also used in the production of herbicides and pesticides.
In case of contact with skin or eyes, the affected area should be rinsed thoroughly with water. Inhalation of triethylamine vapors should be avoided, and work with this chemical should be conducted in a well-ventilated area or under a [[fume hood]].


==Safety==
== Related Pages ==
Triethylamine is a flammable liquid and should be stored away from heat and open flames. It can cause irritation to the skin, eyes, and respiratory system. Proper personal protective equipment, such as gloves and goggles, should be worn when handling the compound.
 
==Related pages==
* [[Amine]]
* [[Amine]]
* [[Base (chemistry)]]
* [[Organic synthesis]]
* [[Organic synthesis]]
* [[Base (chemistry)]]
* [[Nucleophilic substitution]]


[[Category:Organic compounds]]
[[Category:Organic compounds]]
[[Category:Amines]]
[[Category:Amines]]
[[Category:Chemical synthesis]]
[[Category:Chemical synthesis]]

Latest revision as of 05:33, 16 February 2025


Triethylamine[edit]

Structural formula of triethylamine

Triethylamine (TEA) is a tertiary amine with the chemical formula (C2H5)3N. It is a colorless, volatile liquid with a strong fishy odor reminiscent of ammonia. Triethylamine is commonly used in organic synthesis as a base and a catalyst.

Structure and Properties[edit]

Triethylamine is a pyramidal molecule, as depicted in the structural formula. The nitrogen atom is bonded to three ethyl groups, and the lone pair of electrons on the nitrogen contributes to the molecule's basicity. The molecular geometry around the nitrogen is trigonal pyramidal, which is typical for amines.

Triethylamine has a boiling point of 89.5 °C and a melting point of -114.7 °C. It is miscible with most organic solvents and is often used in chemical reactions that require a non-aqueous environment.

Uses[edit]

Triethylamine is widely used in the pharmaceutical industry and in the production of pesticides, herbicides, and other agrochemicals. It serves as a proton acceptor in various chemical reactions, including the deprotonation of carboxylic acids and the formation of amide bonds.

In organic chemistry, triethylamine is often employed as a base in nucleophilic substitution reactions and esterification processes. It is also used in the synthesis of quaternary ammonium compounds.

Safety and Handling[edit]

Triethylamine is a flammable liquid and should be handled with care. It can cause irritation to the skin, eyes, and respiratory tract. Proper personal protective equipment (PPE) such as gloves and goggles should be worn when handling this chemical.

In case of contact with skin or eyes, the affected area should be rinsed thoroughly with water. Inhalation of triethylamine vapors should be avoided, and work with this chemical should be conducted in a well-ventilated area or under a fume hood.

Related Pages[edit]