(TRIETHYL)AMINE

(Triethyl)amine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. 
(Triethyl)amine is a commonly encountered in organic synthesis probably because it is the simplest symmetrically trisubstituted amine, i.e. a tertiary amine, that is liquid at room temperature. 
(Triethyl)amine possesses a strong fishy odor reminiscent of ammonia. 

CAS Number: 121-44-8
EC Number: 204-469-4
IUPAC Name: N,N-Diethylethanamine
Chemical Formula: C6H15N

Other names: N,N-Diethylethanamine, 121-44-8, (Diethylamino)ethane, Ethanamine, N,N-diethyl-, Triethylamin, triethyl amine, Triaethylamin, Trietilamina, N,N,N-Triethylamine, NEt3, trietylamine, tri-ethyl amine, (C2H5)3N, MFCD00009051, N,N-diethyl-ethanamine, VOU728O6AY, CHEBI:35026, Diethylaminoethane, Triethylamine, >=99.5%, Triaethylamin [German], Trietilamina [Italian], CCRIS 4881, HSDB 896, Et3N, TEN [Base], EINECS 204-469-4, UN1296, UNII-VOU728O6AY, triehtylamine, triehylamine, trieihylamine, triethlyamine, triethyamine, TRIETHYLAMINE 100ML, triethylamme, triethylarnine, Thethylamine, Triethlamine, triethyIamine, Triethylannine, tri-ethylamine, triehyl amine, triethyl amin, triethylam ine, triethylami-ne, triethylamine-, trietyl amine, tri ethyl amine, triethyl- amine, AI3-15425, Green Tea 95%, N, N-diethylethanamine, Green Tea PE 50%, Green Tea PE 90%, N,N,N-Triethylamine #, triethylamine, 99.5%, Triethylamine, >=99%, Triethylamine [UN1296] [Flammable liquid], DSSTox_CID_4366, TRIETHYLAMINE [MI], EC 204-469-4, N(Et)3, DSSTox_RID_77381, NCIOpen2_006503, TRIETHYLAMINE [FHFI], TRIETHYLAMINE [HSDB], TRIETHYLAMINE [INCI], DSSTox_GSID_24366, BIDD:ER0331, Triethylamine (Reagent Grade), Triethylamine, LR, >=99%, TRIETHYLAMINE [USP-RS], (CH3CH2)3N, CHEMBL284057, N(CH2CH3)3, DTXSID3024366, FEMA NO. 4246, Triethylamine, HPLC, 99.6%, Triethylamine, p.a., 99.0%, Triethylamine, analytical standard, ADAL1185352, BCP07310, N(C2H5)3, Triethylamine, for synthesis, 99%, ZINC1242720, Tox21_200873, Triethylamine, 99.7%, extra pure, STL282722, AKOS000119998, Triethylamine, purum, >=99% (GC), Triethylamine, ZerO2(TM), >=99%, ZINC112977393, UN 1296, NCGC00248857-01, NCGC00258427-01, CAS-121-44-8, Triethylamine, BioUltra, >=99.5% (GC), Triethylamine, SAJ first grade, >=98.0%, FT-0688146, T0424, Triethylamine 100 microg/mL in Acetonitrile, EN300-35419, Triethylamine [UN1296] [Flammable liquid], Triethylamine, trace metals grade, 99.99, Triethylamine, SAJ special grade, >=98.0%, Triethylamine, puriss. p.a., >=99.5% (GC), Q139199, J-004499, J-525077, F0001-0344, Triethylamine, for amino acid analysis, >=99.5% (GC), Triethylamine, for protein sequence analysis, ampule, >=99.5% (GC), Triethylamine, United States Pharmacopeia (USP) Reference Standard

(Triethyl)amine is a widely used relative of triethylamine. 
(Triethyl)amineis also the smell of the hawthorn plant, and semen, among others 
(Triethyl)amine is commonly employed in organic synthesis as a base, most often in the preparation of esters and amides from acyl chlorides.

Such reactions lead to the production of hydrogen chloride which combines with (Triethyl)amine to form the salt triethylamine hydrochloride, commonly called triethylammonium chloride. 
This reaction removes the hydrogen chloride from the reaction mixture, which is required for these reactions to proceed to completion (R, R' = alkyl, aryl):

R2NH + R'C(O)Cl + Et3N → R'C(O)NR2 + Et3NH+Cl-
Like other tertiary amines, (Triethyl)amine catalyzes the formation of urethane foams and epoxy resins. 
(Triethyl)amine is also useful in dehydrohalogenation reactions and Swern oxidations.

(Triethyl)amine is readily alkylated to give the corresponding quaternary ammonium salt:
RI + Et3N → Et3NR+I-

(Triethyl)amine, also known as (C2H5)3N or NET3, belongs to the class of organic compounds known as trialkylamines. 
These are organic compounds containing a trialkylamine group, characterized by exactly three alkyl groups bonded to the amino nitrogen. 
(Triethyl)amine is an ammoniacal and fishy tasting compound. 
(Triethyl)amine is found, on average, in the highest concentration within grape wine. 
This could make (Triethyl)amine a potential biomarker for the consumption of these foods. 
Based on a literature review a significant number of articles have been published on (Triethyl)amine.

(Triethyl)amine is commonly used as a base during the preparation of esters and amides from acyl chlorides. 
(Triethyl)amine is mainly used in the production of quaternary ammonium compounds for textile auxiliaries and quaternary ammonium salts of dyes. 
(Triethyl)amine acts as a catalyst and acid neutralizer for condensation reactions and is useful as an intermediate for manufacturing medicines, pesticides and other chemicals.

(Triethyl)amine is used as a neutralization agent for anionic stabilized waterborne resins (polyesters, alkyds, acrylic resins and polyurethanes containing carboxyl or other acidic groups). 
(Triethyl)amine is also utilized as a catalyst in the curing of epoxy and polyurethane systems.

(Triethyl)amine PHYSICAL PROPERTIES
Empirical Formula: C6H15N
Structural Formula: (C2H5)3N
Molecular Wt.: 101.19
Sp. Gr. at 20ºC: 0.726-0.730

Refractive Index at 20ºC: 1.399-1.401
Boiling Point: 89°C
Freezing Point: below -80°C
Solubility in water: Soluble upto 18°C. Sparingly soluble above 18°C
Flash Point (closed cup): below -7°C

(Triethyl)amine is a colorless to yellowish liquid with a strong ammonia to fish-like odor. 
(Triethyl)amine is a base commonly used in organic chemistry to prepare esters and amides from acyl chlorides. 
Like other tertiary amines,(Triethyl)amine catalyzes the formation of urethane foams and epoxy resins.

Clear, colorless to light yellow flammable liquid with a strong, penetrating, ammonia-like odor. 
Experimentally determined detection and recognition odor threshold concentrations were <400 μg/m3 (<100 ppbv) and 1.1 mg/m3 (270 ppbv), respectively (Hellman and Small, 1974). 
An odor threshold concentration of 0.032 ppbv was determined by a triangular odor bag method (Nagata and Takeuchi, 1990).

Uses    
(Triethyl)amine is a base used to prepare esters and amides from acyl chlorides as well as in the synthesis of quaternary ammonium compounds. 
(Triethyl)amine acts as a catalyst in the formation of urethane foams and epoxy resins, dehydrohalogeantion reactions, acid neutralizers for condensation reactions and Swern oxidations. 
(Triethyl)amine finds application in reverse phase high-performance liquid chromatography (HPLC) as a mobile-phase modifier. 

(Triethyl)amine is also used as an accelerator activator for rubber, as a propellant, as a corrosion inhibitor, as a curing and hardening agent for polymers and for the desalination of seawater. 
Furthermore, (Triethyl)amine is used in the automotive casting industry and the textile industry.
(Triethyl)amine is used as an anti-livering agent for urea- and melamine-based enamels and in the recovery of gelled paint vehicles (HSDB 1988). 
(Triethyl)amine is also used as a catalyst for polyurethane foams, a flux for copper soldering, and as a catalytic solvent in chemical synthesis (Hawley 1981). 

(Triethyl)amine is used in accelerating activators for rubber; as a corrosion inhibitor for polymers; a propellant; wetting, penetrating, and waterproofing agent of quaternary ammonium compounds; in curing and hardening of polymers (i.e. core-binding resins); and as a catalyst for epoxy resins (Hamilton and Hardy, 1974).

(Triethyl)amine is a clear, colorless liquid with an Ammonia or fish-like odor. 
(Triethyl)amine is used in making waterproofing agents, and as a catalyst, corrosion inhibitor and propellant.
(Triethyl)amine is mainly used as base, catalyst, solvent and raw material in organic synthesis and is generally abbreviated as Et3N, NEt3 or TEA. 

(Triethyl)amine can be used to prepare phosgene polycarbonate catalyst, polymerization inhibitor of tetrafluoroethylene, rubber vulcanization accelerator, special solvent in paint remover, enamel anti-hardener, surfactant, antiseptic, wetting agent, bactericides, ion exchange resins, dyes, fragrances, pharmaceuticals, high-energy fuels, and liquid rocket propellants, as a curing and hardening agent for polymers and for the desalination of seawater.

(Triethyl)amine is used as a competing base for the separation of acidic basic and neutral drugs by reverse-phased high-performance liquid chromatography (HPLC). 
(Triethyl)amine induces visual disturbances (such as foggy vision) in humans (1), and is also used in industry as a quenching agent in the ozonolysis of alkenes. 

(Triethyl)amine is used in the purification of drugs which are pharmacologically or chemically similar through separation in reverse-phase HPLC (2).
Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA). 
Environmental contaminants; Food contaminants.

(Triethyl)amine is used as an anti-livering agent for urea- and melamine-based enamels and in the recovery of gelled paint vehicles (HSDB 1988). 
(Triethyl)amine is also used as a catalyst for polyurethane foams, a flux for copper soldering, and as a catalytic solvent in chemical synthesis (Hawley 1981). 
(Triethyl)amine is used in accelerating activators for rubber; as a corrosion inhibitor for polymers; a propellant; wetting, penetrating, and waterproofing agent of quaternary ammonium compounds; in curing and hardening of polymers (i.e. core-binding resins); and as a catalyst for epoxy resins (Hamilton and Hardy, 1974)

Production    
(Triethyl)amine is produced by ethanol and ammonia in the presence of hydrogen, in containing Cu-Ni-clay catalyst reactor under heating conditions (190 ± 2 ℃ and 165 ± 2 ℃) reaction. 
The reaction also produces ethylamine and diethylamine, products were condensed and then absorption by ethanol spray to obtain crude (Triethyl)amine, through the final separation, dehydration and fractionation, pure triethylamine is obtained.

Health Effects    
(Triethyl)amine is a flammable liquid and a dangerous fire hazard. 
(Triethyl)amine can affect you when inhaled and by passing through the skin. 
Contact can severely irritate and bum the skin and eyes with possible eye damage. 
Exposure can irritate the eyes, nose and throat. 
Inhaling can irritate the lungs. 
Higher exposures may cause a build-up of fluid in the lungs (pulmonary edema), a medical mergency. 
(Triethyl)amine may cause a skin allergy and affect the liver and kidneys.