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Triethyl amine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N.
Triethyl amine is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA is also a common abbreviation.
Triethyl amine is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia.
CAS: 121-44-8
MF: C6H15N
MW: 101.19
EINECS: 204-469-4
Like diisopropylethylamine (Hünig's base), Triethyl amine is commonly employed in organic synthesis, usually as a base.
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 neutralizer 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 automotive casting industry and textile industry.
Triethyl amine (formula: C6H15N), also known as N, N-diethylethanamine, is the most simple tri-substituted uniformly tertiary amine, having typical properties of tertiary amines, including salifying, oxidation, Hing Myers test (Hisberg reaction) for triethylamine does not respond.
Triethyl amine is colorless to pale yellow transparent liquid, with a strong smell of ammonia, slightly fuming in the air.
Boiling point: 89.5 ℃, relative density (water = 1): 0.70, the relative density (Air = 1): 3.48, slightly soluble in water, soluble in alcohol, ether.
Aqueous solution is alkaline, flammable.
Vapor and air can form explosive mixtures, the explosion limit is 1.2% to 8.0%.
Triethyl amine is toxic, with a strong irritant.
Triethyl amine appears as a clear colorless liquid with a strong ammonia to fish-like odor.
Flash point 20°F.
Vapors irritate the eyes and mucous membranes.
Less dense (6.1 lb / gal) than water.
Vapors heavier than air. Produces toxic oxides of nitrogen when burned.
Triethyl amine is an aliphatic amine.
Triethyl amine's addition to matrix-assisted laser desorption/ionization (MALDI) matrices affords transparent liquid matrices with enhanced ability for spatial resolution during MALDI mass spectrometric (MS) imaging.
A head-space gas chromatography (GC) procedure for the determination of Triethyl amine in active pharmaceutical ingredients has been reported.
The viscosity coefficient of Triethyl amine vapor over a range of density and temperature has been measured.
Moderately toxic by ingestion and skin contact.
Mildly toxic by inhalation.
Human systemic effects: visual field changes.
Experimental reproductive effects.
Mutation data reported. A skin and severe eye irritant.
Can cause kidney and liver damage.
A very dangerous fire hazard when exposed to heat, flame, or oxidizers.
Explosive in the form of vapor when exposed to heat or flame.
Complex with dinitrogen tetraoxide explodes below 0°C when undduted with solvent.
Exothermic reaction with maleic anhydride above 150°C.
Can react with oxidzing materials.
Incompatible with N2O4.
To fight fire, use CO2, dry chemical, alcohol foam.
When heated to decomposition Triethyl amine emits toxic fumes of NOx.
Triethyl amine is and aliphatic amine used as a solvent; corrosion inhibitor; in chemical synthesis; and accelerator activators; paint remover; base in methylene chloride or other chlorinated solvents.
Triethyl amine is used to solubilize 2,4,5-T in water and serves as a selective extractant in the purification of antibiotics.
Triethyl amine is used to manufacture quaternary ammonia compounds and octadecyloxymethyltriethylammonium chloride; an agent used in textile treatment.
Triethyl amine Chemical Properties
Melting point: -115 °C
Boiling point: 90 °C
Density : 0.728
Vapor density: 3.5 (vs air)
Vapor pressure: 51.75 mm Hg ( 20 °C)
Refractive index: n20/D 1.401(lit.)
FEMA: 4246 | TRIETHYLAMINE
Fp: 20 °F
Storage temp.: Store below +30°C.
Solubility: water: soluble112g/L at 20°C
pka: 10.75(at 25℃)
Form: Liquid
Specific Gravity: 0.725 (20/4℃)
Color: Clear
PH: 12.7 (100g/l, H2O, 15℃)(IUCLID)
Relative polarity: 1.8
Odor: Strong ammonia-like odor
Odor Threshold: 0.0054ppm
Explosive limit: 1.2-9.3%(V)
Water Solubility: 133 g/L (20 ºC)
Merck: 14,9666
JECFA Number: 1611
BRN: 1843166
Henry's Law Constant: 1.79 at 25 °C (Christie and Crisp, 1967)
Exposure limits NIOSH REL: IDLH 200 ppm; OSHA PEL: TWA 25 ppm (100 mg/m3); ACGIH TLV: TWA 1 ppm, STEL 3 ppm (adopted).
Stability: Stable. Extremely flammable.
Readily forms explosive mixtures with air.
Note low flash point.
Incompatible with strong oxidizing agents, strong acids, ketones, aldehydes, halogenated hydrocarbons.
InChIKey: ZMANZCXQSJIPKH-UHFFFAOYSA-N
CAS DataBase Reference: 121-44-8(CAS DataBase Reference)
NIST Chemistry Reference: Triethyl amine(121-44-8)
EPA Substance Registry System: Triethyl amine (121-44-8)
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).
Synthesis and properties
Triethyl amine is prepared by the alkylation of ammonia with ethanol:
NH3 + 3 C2H5OH → N(C2H5)3 + 3 H2O
The pKa of protonated triethyl amine is 10.75, and it can be used to prepare buffer solutions at that pH.
The hydrochloride salt, triethyl amine hydrochloride (triethylammonium chloride), is a colorless, odorless, and hygroscopic powder, which decomposes when heated to 261 °C.
Triethyl amine is soluble in water to the extent of 112.4 g/L at 20 °C.
Triethyl amine 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.
In alkane solvents triethyl amine is a Lewis base that forms adducts with a variety of Lewis acids, such as I2 and phenols.
Owing to its steric bulk, Triethyl amine forms complexes with transition metals reluctantly.
Applications
Triethyl amine is commonly employed in organic synthesis as a base.
For example, Triethyl amine is commonly used as a base during 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 triethyl amine hydrochloride, commonly called triethylammonium chloride.
Hydrogen chloride may then evaporate from the reaction mixture, which drives the reaction. (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 is mainly used in the production of quaternary ammonium compounds for textile auxiliaries and quaternary ammonium salts of dyes.
Triethyl amine is also a catalyst and acid neutralizer for condensation reactions and is useful as an intermediate for manufacturing medicines, pesticides and other chemicals.
Triethyl amine 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 can be used while performing analysis.
Uses
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 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 (TEA, Et3N) is an aliphatic amine.
Triethyl amine is used to catalytic solvent in chemical synthesis; accelerator activators for rubber; wetting, penetrating, and waterproofing agents of quaternary ammonium types; curing and hardening of polymers (e.g., corebinding resins); corrosion inhibitor; propellant.
Triethyl amine has been used during the synthesis of: 5′-dimethoxytrityl-5-(fur-2-yl)-2′-deoxyuridine 3′-(2-cyanoethyl)diisopropylphosphoramidite-5′-dimethoxytrityl-5-(fur-2-yl)-2′-deoxyuridine polyethylenimine600-β-cyclodextrin (PEI600-β-CyD).
Triethyl amine may be used as a homogeneous catalyst for the preparation of glycerol dicarbonate, via transesterification reaction between glycerol and dimethyl carbonate (DMC).
Triethyl amine is used in the following products: pH regulators and water treatment products, polymers, coating products, metal working fluids, paper chemicals and dyes, metal surface treatment products, lubricants and greases and plant protection products.
Triethyl amine is used for the manufacture of: chemicals, pulp, paper and paper products and rubber products.
Release to the environment of Triethyl amine can occur from industrial use: formulation of mixtures, in processing aids at industrial sites, in the production of articles and of substances in closed systems with minimal release.
Other release to the environment of Triethyl amine is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners) and outdoor use.
Industrial uses
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 amineis used in the following products: pH regulators and water treatment products, polymers, laboratory chemicals, metal working fluids, paper chemicals and dyes, adhesives and sealants and lubricants and greases.
Triethyl amine has an industrial use resulting in manufacture of another substance (use of intermediates).
Triethyl amine is used in the following areas: mining.
Triethyl amine is used for the manufacture of: chemicals, textile, leather or fur, rubber products, plastic products and fabricated metal products.
Release to the environment of Triethyl amine can occur from industrial use: in processing aids at industrial sites, as an intermediate step in further manufacturing of another substance (use of intermediates), in the production of articles, as processing aid, as processing aid and of substances in closed systems with minimal release.
Niche uses
Triethyl amine is used to give salts of various carboxylic acid-containing pesticides, e.g. Triclopyr and 2,4-dichlorophenoxyacetic acid.
Triethyl amine is the active ingredient in FlyNap, a product for anesthetizing Drosophila melanogaster.
Triethyl amine is 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 salt of triethyl amine (often abbreviated TEAB, triethylammonium bicarbonate) is useful in reverse phase chromatography, often in a gradient to purify nucleotides and other biomolecules.
Triethyl amine was found during the early 1940s to be hypergolic in combination with nitric acid, and was considered a possible propellant for early hypergolic rocket engines.
The Soviet "Scud" Missile used TG-02 ("Tonka-250"), a mixture of 50% xylidine and 50% triethly amine as a starting fluid to ignite its rocket engine.
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.
Triethyl amine is prepared by a vapor phase reaction of ammonia with ethanol or reaction of N,N-diethylacetamide with lithium aluminum hydride (Windholz et al 1983).
Triethyl amine may also be produced from ethyl chloride and ammonia under heat and pressure (Hawley 1981) or by vapor phase alkylation of ammonia with ethanol (HSDB 1988).
U.S. production is estimated at greater than 22,000 tons in 1972 (HSDB 1988).
Purification Methods
Dry triethyl amine with CaSO4, LiAlH4, Linde type 4A molecular sieves, CaH2, KOH, or K2CO3, then distil it, either alone or from BaO, sodium, P2O5 or CaH2.
Triethyl amine has also been distilled from zinc dust, under nitrogen.
To remove traces of primary and secondary amines, triethyl amine has been refluxed with acetic anhydride, benzoic anhydride, phthalic anhydride, then distilled, refluxed with CaH2 (ammonia-free) or KOH (or dried with activated alumina), and again distilled.
Another purification method involved refluxing for 2hours with p-toluenesulfonyl chloride, then distilling.
Grovenstein and Williams treated triethyl amine (500mL) with benzoyl chloride (30mL), filtered off the precipitate, and refluxed the liquid for 1hour with a further 30mL of benzoyl chloride. After cooling, the liquid was filtered, distilled, and allowed to stand for several hours with KOH pellets.
Triethyl amine was then refluxed with, and distilled from, stirred molten potassium.
Triethyl amine has been converted to its hydrochloride (see brlow), crystallised from EtOH (to m 254o), then liberated with aqueous NaOH, dried with solid KOH and distilled from sodium under N2.
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.
Vapors irritate nose, throat, and lungs, causing coughing, choking, and difficult breathing. Contact with eyes causes severe burns.
Clothing wet with chemical causes skin burns.
Triethyl amine may also be irritating to skin and mucous membranes (Windholz et al 1983).
Reactivity Profile
Triethyl amine reacts violently with oxidizing agents.
Reacts with Al and Zn. Neutralizes acids in exothermic reactions to form salts plus water.
May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides.
Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Metabolism
There have been few studies on the metabolism of industrially important aliphatic amines such as triethylamine.
Triethyl amine is generally assumed that amines not normally present in the body are metabolized by monoamine oxidase and diamine oxidase (histaminase).
Ultimately ammonia is formed and will be converted to urea.
The hydrogen peroxide formed is acted upon by catalase and the aldehyde formed is thought to be converted to the corresponding carboxylic acid by the action of aldehyde oxidase (Beard and Noe 1981).
Fire Hazard
Flammable/combustible material. May be ignited by heat, sparks or flames.
Vapors may form explosive mixtures with air.
Vapors may travel to source of ignition and flash back.
Most vapors are heavier than air.
They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers.
Runoff to sewer may create fire or explosion hazard.
Containers may explode when heated.
Many liquids are lighter than water.
Biochem/physiol Actions
Triethyl amine is known to drive polymerization reaction.
Triethyl amine acts as a source of carbon and nitrogen for bacterial cultures.
Triethyl amine is used in pesticides.
Triethyl amine can serve as an organic solvent.
Synonyms
TRIETHYLAMINE
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
