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Triethylamine (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.
Triethylamine 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.
CAS: 121-44-8
MF: C6H15N
MW: 101.19
EINECS: 204-469-4
Triethylamineis the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N.
Triethylamine 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.
Triethylamine is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia.
Like diisopropylethylamine (Hünig's base), Triethylamine is commonly employed in organic synthesis, usually as a base.
Triethylamine 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.
Triethylamine is a tertiary amine that is ammonia in which each hydrogen atom is substituted by an ethyl group.
Aqueous solution is alkaline, flammable.
Vapor and air can form explosive mixtures, the explosion limit is 1.2% to 8.0%.
Triethylamine is toxic, with a strong irritant.
There have been few studies on the metabolism of industrially important aliphatic amines such as triethylamine.
Triethylamine 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.
Triethylamine 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: Triethylamine(121-44-8)
EPA Substance Registry System: Triethylamine (121-44-8)
Triethylamine is a colorless to yellowish liquid with a strong ammonia to fish-like odor.
Triethylamine is a base commonly used in organic chemistry to prepare esters and amides from acyl chlorides.
Like other tertiary amines,Triethylamine catalyzes the formation of urethane foams and epoxy resins.
Physical properties
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.
An odor threshold concentration of 0.032 ppbv was determined by a triangular odor bag method.
Uses
Triethylamine is a clear, colorless liquid with an Ammonia or fish-like odor.
Triethylamine is used in making waterproofing agents, and as a catalyst, corrosion inhibitor and propellant.
Triethylamine is mainly used as base, catalyst, solvent and raw material in organic synthesis and is generally abbreviated as Et3N, NEt3 or TEA.
Triethylamine 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.
Triethylamine is a base used to prepare esters and amides from acyl chlorides as well as in the synthesis of quaternary ammonium compounds.
Triethylamine acts as a catalyst in the formation of urethane foams and epoxy resins, dehydrohalogeantion reactions, acid neutralizers for condensation reactions and Swern oxidations.
Triethylamine finds application in reverse phase high-performance liquid chromatography (HPLC) as a mobile-phase modifier.
Triethylamine 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,Triethylamine is used in the automotive casting industry and the textile industry.
Triethylamine is used as an anti-livering agent for urea- and melamine-based enamels and in the recovery of gelled paint vehicles.
Triethylamine is also used as a catalyst for polyurethane foams, a flux for copper soldering, and as a catalytic solvent in chemical synthesis.
Triethylamine 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.
Triethylamine is commonly employed in organic synthesis as a base.
For example, Triethylamine 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 triethylamine to form the salt triethylamine 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, it catalyzes the formation of urethane foams and epoxy resins.
Triethylamine is also useful in dehydrohalogenation reactions and Swern oxidations.
Triethylamine is readily alkylated to give the corresponding quaternary ammonium salt:
RI + Et3N → Et3NR+I−
Triethylamine is mainly used in the production of quaternary ammonium compounds for textile auxiliaries and quaternary ammonium salts of dyes.
Triethylamine is also a catalyst and acid neutralizer for condensation reactions and is useful as an intermediate for manufacturing medicines, pesticides 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 can be used while performing analysis.
Production
Triethylamine 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 triethylamine, through the final separation, dehydration and fractionation, pure triethylamine is obtained.
Synthesis and properties
Triethylamine is prepared by the alkylation of ammonia with ethanol:
NH3 + 3 C2H5OH → N(C2H5)3 + 3 H2O
The pKa of protonated triethylamine is 10.75, and it can be used to prepare buffer solutions at that pH.
The hydrochloride salt, triethylamine hydrochloride (triethylammonium chloride), is a colorless, odorless, and hygroscopic powder, which decomposes when heated to 261 °C.
Triethylamine is soluble in water to the extent of 112.4 g/L at 20 °C.
Triethylamine 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 triethylamine is a Lewis base that forms adducts with a variety of Lewis acids, such as I2 and phenols.
Owing to its steric bulk, Triethylamine forms complexes with transition metals reluctantly.
Health Effects
Triethylamine is a flammable liquid and a dangerous fire hazard.
Triethylamine 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.
Triethylamine may cause a skin allergy and affect the liver and kidneys.
Production Methods
Triethylamine is prepared by a vapor phase reaction of ammonia with ethanol or reaction of N,N-diethylacetamide with lithium aluminum hydride.
Triethylamine may also be produced from ethyl chloride and ammonia under heat and pressure or by vapor phase alkylation of ammonia with ethanol.
U.S. production is estimated at greater than 22,000 tons in 1972.
Reactivity Profile
Triethylamine 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.
Health Hazard
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.
Triethylamine may also be irritating to skin and mucous membranes.
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
Triethylamine is known to drive polymerization reaction.
Triethylamine acts as a source of carbon and nitrogen for bacterial cultures.
Triethylamine is used in pesticides.
Triethylamine can serve as an organic solvent.
Purification Methods
Dry triethylamine with CaSO4, LiAlH4, Linde type 4A molecular sieves, CaH2, KOH, or K2CO3, then distil it, either alone or from BaO, sodium, P2O5 or CaH2.
Triethylamine has also been distilled from zinc dust, under nitrogen.
To remove traces of primary and secondary amines, triethylamine 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 triethylamine (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.
Triethylamine was then refluxed with, and distilled from, stirred molten potassium.
Triethylamine 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.
Synonyms
TRIETHYLAMINE
N,N-Diethylethanamine
121-44-8
(Diethylamino)ethane
Ethanamine, N,N-diethyl-
triethyl amine
Triaethylamin
Triethylamin
Trietilamina
N,N,N-Triethylamine
NEt3
trietylamine
tri-ethyl amine
(C2H5)3N
MFCD00009051
N,N-diethyl-ethanamine
VOU728O6AY
DTXSID3024366
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]
TRIETHYLAMINE [MI]
EC 204-469-4
N(Et)3
NCIOpen2_006503
TRIETHYLAMINE [FHFI]
TRIETHYLAMINE [HSDB]
TRIETHYLAMINE [INCI]
BIDD:ER0331
Triethylamine (Reagent Grade)
Triethylamine, LR, >=99%
TRIETHYLAMINE [USP-RS]
(CH3CH2)3N
CHEMBL284057
DTXCID204366
N(CH2CH3)3
FEMA NO. 4246
Triethylamine, HPLC, 99.6%
Triethylamine, p.a., 99.0%
Triethylamine, analytical standard
ADAL1185352
BCP07310
N(C2H5)3
Triethylamine, for synthesis, 99%
Tox21_200873
Triethylamine, 99.7%, extra pure
STL282722
AKOS000119998
Triethylamine, purum, >=99% (GC)
Triethylamine, ZerO2(TM), >=99%
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
