TRIETHYLAMINE
TRIETHYLAMINE
TRIETHYLAMINE
CAS no.: 121-44-8
EC / List no.: 204-469-4
Mol. formula: C6H15N
SYNONYMS:
(Diethylamino)ethane
Ethanamine, N,N-diethl
N,N,N,triethylamine
N,N-diethylethanamine
TEA
TRIETHYL AMINE
Triethylamin
TRIETHYLAMINE
Triethylamine
(Triethyl)amine
Applications of Triethylamine:
Agriculture Chemical solvents
Agriculture intermediates
Aluminum production
Chemicals & petrochemicals
Electronic chemicals
Insecticides intermediate
Intermediates
Mining
Pharmaceutical chemicals
Resins
Triethylamine Application Areas
Some of its major uses in the industry include:
• Catalyst to cure resin systems incorporated into sand cores for foundry molds.
• Used for the precipitation and purification of antibiotics, such as penicillin.
• Used as a catalyst for isocyanate reactions, for example as a cross-linking catalyst in the production of polyurethane foams.
• Catalyst for epoxy resins.
Triethylamine has a broad range of miscellaneous applications:
• Production of herbicides, such as 2,4-D.
• Production of polycarbonate resins.
• A neutralization agent in waterborne paints based on polyesters, alkyds, acrylic resins and polyurethanes containing acidic groups.
• Curing catalyst in particleboard adhesives.
• Corrosion inhibitor for polymers.
• Production of Diethylhydroxylamine and other amine derivatives.
Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N.
Triethylamine is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia.
Triethylamine is commonly employed, usually as a base, in organic synthesis.
Triethylamine anhydrous is a chemical compound that can be used as a catalyst for isocyanate reactions and as a neutralization agent for anionic stabilized waterborne resins.
Triethylamine is used as a catalyst for the synthesis of polyurethanes and for two-component paints.
Triethylamine is suitable as a neutralization agent in waterborne paints based on polyesters, alkyds, acrylic resins, and polyurethanes containing carboxyl or other acidic groups.
Due to excellent water solubility and lack of active hydrogen atoms, triethylamine is often used for the production of water-borne polyurethane dispersions.
Triethylamine—often abbreviated as TEA or Et3N—is a colorless, volatile liquid used in creating polyurethane dispersions (PUDs).
Triethylamine is commonly employed in organic synthesis as a base for a variety of applications, such as a catalytic solvent in chemical syntheses, a corrosion inhibitor, and a curing and hardening agent for polymers.
In PUDs, Triethylamine functions as a counter ion to the acid in the polymer backbone, allowing for the formation of polymer particles in water.
Triethylamine accomplishes this by ionizing the carboxylic acid in the polyurethane prepolymer.
The Triethylamine neutralizes the acid in the prepolymer, forming an ionized acid-base pair that makes it dispersible—without being ionized, it would not have the required affinity for water necessary for creating a polymeric dispersion.
Triethylamine is used as a neutralization agent for anionic stabilized waterborne resins (polyesters, alkyds, acrylic resins, and polyurethanes containing carboxyl or other acidic groups).
Triethylamine is also utilized as a catalyst in the curing of epoxy and polyurethane systems.
Triethylamine is primarily used as a proton scavenger in synthesis.
Triethylamine is also used in the production of Diethylhydroxylamine and other organic compounds
Triethylamine is mainly used in the production of quaternary ammonium compounds for textile auxiliaries and quaternary ammonium salts of dyes.
Triethylamine is a catalyst and acid neutralizer for condensation reactions and is useful as an intermediate for manufacturing medicines, pesticides, and other chemicals.
Triethylamine Chemical Properties, Uses, and Production
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.
USES OF TRIETHYLAMINE
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, dehydrohalogenation 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, it is used in the automotive casting industry and the textile industry.
Uses
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., core-binding resins); corrosion inhibitor; propellant.
Synthesis and properties of Triethylamine:
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,[3] 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 acid such as I2 and phenols.
Owing to its steric bulk, it forms complexes with transition metals reluctantly.
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.
This reaction removes the hydrogen chloride from the reaction mixture, which can be 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, it catalyzes the formation of urethane foams and epoxy resins. It 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 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.
Niche uses
Triethylamine is used to give salts of various carboxylic acid-containing pesticides, e.g. Triclopyr and 2,4-dichlorophenoxyacetic acid
Triethylamine is the active ingredient in FlyNap, a product for anesthetizing Drosophila melanogaster.
Triethylamine 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.
Also, the bicarbonate salt of triethylamine (often abbreviated TEAB, triethylammonium bicarbonate) is useful in reverse phase chromatography, often in a gradient to purify nucleotides and other biomolecules.[citation needed]
Triethylamine 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.
triethylamin (cs)
triethylamin (da)
Triethylamin (de)
triethylamine (nl)
trietil-amin (hu)
trietilamin (hr)
trietilamin (sl)
trietilamina (es)
trietilamina (it)
trietilamina (pt)
trietilamina (ro)
trietilaminas (lt)
trietilamīns (lv)
trietylamin (no)
trietylamin (sv)
trietylamín (sk)
trietyloamina (pl)
trietyyliamiini (fi)
Trietüülamiin (et)
triéthylamine (fr)
τριαιθυλαμίν (el)
триетиламин (bg)
TRIETHYLAMINE
N,N-Diethylethanamine
121-44-8
Ethanamine, N,N-diethyl-
(Diethylamino)ethane
Triethylamin
triethyl amine
Triaethylamin
Trietilamina
N,N,N-Triethylamine
NEt3
trietylamine
triethyl-amine
tri-ethyl amine
UNII-VOU728O6AY
(C2H5)3N
MFCD00009051
Et3N
N,N-diethyl-ethanamine
VOU728O6AY
CHEBI:35026
Diethylaminoethane
Triethylamine, >=99.5%
Triaethylamin [German]
Trietilamina [Italian]
EINECS 204-469-4
UN1296
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
N, N-diethylethanamine
N,N,N-Triethylamine #
triethylamine, 99.5%
Triethylamine, >=99%
Triethylamine [UN1296] [Flammable liquid]
ACMC-1BP6L
DSSTox_CID_4366
EC 204-469-4
Triethylamine—often abbreviated as TEA or Et3N—is a colorless, volatile liquid used in creating polyurethane dispersions (PUDs).
It is commonly employed in organic synthesis as a base for a variety of applications, such as a catalytic solvent in chemical syntheses, a corrosion inhibitor, and a curing and hardening agent for polymers.
In PUDs, Triethylamine functions as a counter ion to the acid in the polymer backbone, allowing for the formation of polymer particles in water.
It accomplishes this by ionizing the carboxylic acid in the polyurethane prepolymer.
The Triethylamine neutralizes the acid in the prepolymer, forming an ionized acid-base pair that makes it dispersible—without being ionized, it would not have the required affinity for water necessary for creating a polymeric dispersion.
However, Triethylamine has recently faced challenges and regulatory pressure due to its hazardous vapors.
Even short-term exposure to the vapors can cause severe irritation to the eyes and skin.
In addition to its human health concerns, Triethylamine is considered a volatile organic compound (VOC) and has an unpleasant, potent odor that is sometimes described as the smell of expired fish.
While Triethylamine does offer some unique advantages for the production of PUDs, Triethylamine-free PUD formulations can be just as effective with the right formulation changes—without hazards to human health.
One alternative to Triethylamine is dimethylethanolamine (DMEA).
It requires a bit more attention in the processing of PUDs because DMEA has reactive alcohol attached (ethanol substituent).
That means it needs to be added to the water phase, unlike Triethylamine which can be added directly to the prepolymer.
DMEA also has a higher boiling point (less volatile) than Triethylamine, so it takes longer to leave the coating, which can reduce the chemical resistance of the coating when tested.
DMEA can provide a colloidally stable particle size and dispersion; in large part due to its ability not to shock the prepolymer when its added to the water.
However, it is still a relatively undesirable VOC with a poor odor profile.
Inorganic or metal bases, such as sodium and potassium hydroxide, can be used as a Triethylamine alternative for ionizing acid substituents on polymers.
However, these materials can be difficult to work with and can negatively impact final PUD qualities.
Because metals such as sodium form such strong bases, they tend to shock or agglomerate the prepolymer as it is added to water, resulting in a gritty/“dirty” dispersion of poor quality that contains polymer that is not stable in water and result in sediment in the container.
Moreover, metal bases such as sodium are permanent or non-volatile and may be expected to negatively impact coating performance in terms of poorer water resistance.
However, they will not contribute to the VOC emissions of the coating, improving the sustainability of the product.
Another alternative is ammonia, which is commonly used to adjust the pH or create ionized acrylic emulsions.
However, it is difficult to use to prepare PUDs due to their high level of reactivity with isocyanates.
Without taking special precautions, ammonia will react with the isocyanate functional prepolymer during the dispersion process and convert the isocyanate into urea. The resulting urea will not react further to build the molecular weight of the prepolymer.
Polymers need to be a certain molecular weight to function properly and the use of ammonia will likely result in a lower molecular weight polymer.
If the molecular weight becomes too low for the final product, it can impact final performance, possibly to such an extent that the product no longer behaves like a solid, but more like a liquid. In other words – a tacky material that is not useful as a protective coating.
Thus, ammonia, or any amine with hydrogen attached, would be problematic to use to disperse an anionic water-dispersible polyurethane containing active isocyanate for creating a high molecular weight polymer.
Nonionic dispersing groups can be used to make a PUD and avoid using Triethylamine or the need for any other counter ion.
However, these types of polymers are typically inferior to anionic PUDs as protective coatings.
This is due to the permanance of the water-soluble nonionic dispersing material, as well as the relatively large amounts needed to produce polymeric dispersion of a particle size required for a stable dispersion in water.
This results in a coating with significantly higher sensitivity to water and other polar solvents compared to that obtainable from an anionic dispersion.
Synthesis without Triethylamine can be more challenging, but from an application standpoint, it doesn’t change how the PUR could be used.
However, properties such as chemical resistance, hardness, and film formation can be negatively impacted should the formulation or composition not be as robust as that when using Triethylamine-based PUDs.
From an applications standpoint, formulating a Triethylamine-free PUD is no different than formulating one that contains the material.
However, should a formulator change from a Triethylamine-containing PUD to a Triethylamine-free alternative, they should reevaluate other raw material choices, particularly co-solvent selection. Solvent choice is integral to film formation, which in turn will impact coating performance, i.e. hardness, barrier properties, and chemical resistance.
If a decrease in performance in these areas is observed, solvent loading should be reoptimized to restore performance.
When evaluating a Triethylamine free PUD for the first time, a normal formulation methodology should be followed.
Materials should be screened individually for compatibility and effectiveness with the resin.
The best raw materials from each screening study should then be combined into an initial coating formulation for testing.
Based on those results, the formula is refined (optimized) and retested.
This iterative process continues until the desired performance is obtained.
Triethylamine is a tertiary amine that is ammonia in which each hydrogen atom is substituted by an ethyl group.
Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N.
It 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 (TEA, Et3N) is an aliphatic amine.
Its addition to matrix-assisted laser desorption/ionization (MALDI) matrices affords transparent liquid matrices with an enhanced ability for spatial resolution during MALDI mass spectrometric (MS) imaging.
A head-space gas chromatography (GC) procedure for the determination of triethylamine in active pharmaceutical ingredients has been reported.
The viscosity coefficient of triethylamine vapor over a range of density and temperature has been measured.
Triethylamine is mainly used in the production of quaternary ammonium compounds for textile auxiliaries and quaternary ammonium salts of dyes.
It is also a catalyst and acid neutralizer for condensation reactions and is useful as an intermediate for manufacturing medicines, pesticides, and other chemicals.
Triethylamine belongs to the trialkyl amine class.
Triethylamine finds widespread use in the chemical industry.
Coatings
Triethylamine is used as a neutralization agent for anionic stabilized waterborne resins (polyesters, alkyds, acrylic resins and polyurethanes containing carboxyl or other acidic groups).
It is also utilized as a catalyst in the curing of epoxy and polyurethane systems.
CAS No.: 121-44-8
Chemical synonyms: Ethanamine, N,N-diethyl-; Triethylamine
Product description
Triethylamine (TEA) is a colorless liquid with an ammonia-like odor.
Triethylamine is a synthetic chemical compound with the formula: N(CH2CH3)3.
This formula is commonly abbreviated as Et3N or TEA.
The “TEA” abbreviation must be carefully used in order to prevent confusion with triethanolamine or tetraethyl ammonium, however.
As a hydrochloride salt, it is a colorless, volatile liquid substance with a strong “fishy” odor.
Triethylamine is created by alkalizing ethanol with ammonia.
As a hydrochloride salt, triethylamine is an odorless, colorless powder that attracts and holds water molecules very easily.
In this form, Triethylamine decomposes at an ambient temperature of 261 degrees Celsius.
Triethylamine is a commonly used base in the organic synthesis of other chemical compounds.
This is especially true of amides from acyl chlorides and esters.
In the industrial arena, Triethylamine is primarily used to produce quaternary ammoniums (“QAs”) for textiles and the QA salt derivative of various fabric dyes.
Because it also functions as an acid neutralizer and chemical catalyst, it is often used in an intermediate capacity for pesticide and medication manufacturing.
Triethylamine
CAS Number: 121-44-8
Synonym: AI3-15425; N, N-diethylethanamine; TEA
Occurrence/Use
Organic chemical synthesis, rubber accelerator activator, corrosion inhibitor, propellant, seawater desalination; production of urethane foams and epoxy resins, pharmaceuticals, pesticides; component of tobacco smoke
Applications/uses
Ag chem solvents
Agriculture intermediates
Aluminum production
Chemicals & petrochemicals
Electronic chemicals
Insecticides int
Intermediates
Mining
Pharmaceutical chemicals
Resins
Other
In synthesis, Triethylamine is primarily used as a proton scavenger; however, it is also used in the production of Diethylhydroxylamine and other organic compounds
Application
Triethylamine 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)
Other names: Ethanamine, N,N-diethyl-; (C2H5)3N; (Diethylamino)ethane; N,N-Diethylethanamine; TEN; Triaethylamin; Trietilamina; UN 1296; 1069-58-5 (maleate); 554-68-7 (chloride)
It may be used as a homogeneous catalyst for the preparation of glycerol dicarbonate, via transesterification reaction between glycerol and dimethyl carbonate (DMC)
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.
It is colorless to pale yellow transparent liquid, with a strong smell of ammonia, slightly fuming in the air.
Triethylamine is a tertiary amine which is abbreviated as TEA.
It is a colorless liquid and is commonly used in organic synthesis.
ATAMAN CHEMICALS offers high purity triethylamine in a variety of capacities safely stored in amber glass bottles.
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.
The aqueous solution is alkaline, flammable. Vapor and air can form explosive mixtures, the explosion limit is 1.2% to 8.0%. It is toxic, with a strong irritant.
Uses
Triethylamine is a clear, colorless liquid with an Ammonia or fish-like odor.
It is used in making waterproofing agents, and as a catalyst, corrosion inhibitor, and propellant.
It is mainly used as a base, catalyst, solvent, and raw material in organic synthesis and is generally abbreviated as Et3N, NEt3, or TEA.
It can be used to prepare phosgene polycarbonate catalyst, polymerization inhibitor of tetrafluoroethylene, rubber vulcanization accelerator, a 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.
Production
It 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 absorbed by ethanol spray to obtain crude triethylamine, through the final separation, dehydration, and fractionation, pure triethylamine is obtained.
Health Effects
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 Triethylamine 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.
Triethylamine may affect the liver and kidneys.
Triethylamine is a flammable liquid and a dangerous fire hazard.
Category
Flammable liquids
Toxicity grading
Toxic
Applications
Triethylamine is a base used to prepare esters and amides from acyl chlorides as well as in the synthesis of quaternary ammonium compounds.
It acts as a catalyst in the formation of urethane foams and epoxy resins, dehydrohalogeantion reactions, acid neutralizer for condensation reactions and Swern oxidations.
It finds application in reverse phase high-performance liquid chromatography (HPLC) as a mobile-phase modifier.
It 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, it is used in automotive casting industry and textile industry.
It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia.
Like diisopropylethylamine (Hünig’s base), triethylamine is commonly employed, usually as a base, in organic synthesis.
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.
Preferred IUPAC name: N,N-Diethylethanamine
Other names: (Triethyl)amine, Triethylamine, N,N-Diethylethanamine
CAS Number: 121-44-8 check
Chemical formula: C6H15N
Molar mass: 101.193 g·mol−1
Appearance: Colourless liquid
Odor: Fishy, ammoniacal
Density:0.7255 g mL−1
Melting point: −114.70 °C
Boiling point: 88.6 to 89.8 °C
log P: 1.647
Vapor pressure:6.899–8.506 kPa
Henry’s law
constant (kH): 66 μmol Pa−1 kg−1
Acidity (pKa): 10.75 (for the conjugate acid) (H2O), 9.00 (DMSO)
Magnetic susceptibility (χ): -81.4·10−6 cm3/mol
Refractive index (nD): 1.401
(C2H5)3N [Formula]
10575-25-4 [RN]
119618-21-2 [RN]
119618-22-3 [RN]
121-44-8 [RN]
14943-53-4 [RN]
173324-94-2 [RN]
204-469-4 [EINECS]
221-130-6 [EINECS]
234-163-6 [EINECS]
3010-02-4 [RN]
3563-01-7 [RN]
605283 [Beilstein]
Diethylaminoethyl
Et3N [Formula]
Ethanamine, N,N-diethyl- [ACD/Index Name]
MFCD00009051 [MDL number]
N,N,N-triethylamine
N,N-Diethylethanamin [German] [ACD/IUPAC Name]
N,N-Diethylethanamine [ACD/IUPAC Name]
N,N-Diéthyléthanamine [French] [ACD/IUPAC Name]
NEt3 [Formula]
TEA
triethyl amine
Triethylamine [Wiki]
Trietilamina [Italian]
(diethylamino)ethane
109-16-0 [RN]
203-652-6 [EINECS]
204-469-4MFCD00009051
66688-79-7 [RN]
73602-61-6 [RN]
Acid
diethylaminoethane
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:35026
MFCD00008591 [MDL number]
N,N-Diethyl-Ethanamine
N,N-Diethylethanamine, (Diethylamino)Ethane
N,N-Diethylethanamine, TEA
TEN
Triaethylamin [German]
Triaethylamin
Triethylamin
Triethyl-amine
Triethylamine 100 µg/mL in Acetonitrile
Triethylamine, trace metals grade, 99.99%
Triethylamine, 99.7%, extra pure
triethylammonium
三乙胺 [Chinese]
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.
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.
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, 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 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.
This reaction removes the hydrogen chloride from the reaction mixture, which can be 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, it catalyzes the formation of urethane foams and epoxy resins.
It 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.
It 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.
Niche uses
Triethylamine is used to give salts of various carboxylic acid-containing pesticides, e.g. Triclopyr and 2,4-dichlorophenoxyacetic acid
Triethylamine is the active ingredient in FlyNap, a product for anesthetizing Drosophila melanogaster.
Triethylamine 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.
Also, the bicarbonate salt 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 found during the early 1940s to be hypergolic in combination with nitric acid and was considered a possible propellant for early hypergolic rocket engines.
Acute (short-term) exposure of humans to triethylamine vapor causes eye irritation, corneal swelling, and halo vision.
People have complained of seeing “blue haze” or having “smoky vision.”
These effects have been reversible upon cessation of exposure.
Acute exposure can irritate the skin and mucous membranes in humans.
Chronic (long-term) exposure of workers to triethylamine vapor has been observed to cause reversible corneal edema.
Chronic inhalation exposure has resulted in respiratory and hematological effects and eye lesions in rats and rabbits.
No information is available on the reproductive, developmental, or carcinogenic effects of triethylamine in humans.
EPA has not classified triethylamine with respect to potential carcinogenicity.
Chemical Properties
Colorless to yellowish liquid; fishy aroma.
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 (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
In the manufacture of waterproofing agents; as a corrosion inhibitor; as a propellant.
Uses
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.
Definition
ChEBI: A tertiary amine that is ammonia in which each hydrogen atom is substituted by an ethyl group.
Production Methods
Triethylamine 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).
It 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).
Aroma threshold values
High strength odor, fishy type; recommend smelling in a 0.01% solution or less.
General Description
A clear colorless liquid with strong ammonia to fish-like odor.
Flashpoint 20°F.
Vapors irritate the eyes and mucous membranes.
Less dense (6.1 lb / gal) than water.
Vapors are heavier than air.
Produces toxic oxides of nitrogen when burned.
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 the nose, throat, and lungs, causing coughing, choking, and difficult breathing.
Contact with the eyes causes severe burns.
Clothing wet with chemicals causes skin burns.
Health Hazard
Eye irritation and corneal edema have been reported from exposures in the industry (Beard and Noe, 1981; Akesson et al 1985).
Triethylamine may also be irritating to skin and mucous membranes (Windholz et al 1983).
Fire Hazard
Flammable/combustible material. May be ignited by heat, sparks, or flames.
Vapors may form explosive mixtures with air.
Vapors may travel to the source of ignition and flashback.
Most vapors are heavier than air.
They will spread along the 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 hazards.
Containers may explode when heated. Many liquids are lighter than water.
Industrial uses
Triethylamine is used as an anti-livering agent for urea- and melamine-based enamels and in the recovery of gelled paint vehicles (HSDB 1988).
It is also used as a catalyst for polyurethane foams, a flux for copper soldering, and as a catalytic solvent in chemical synthesis (Hawley 1981).
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 (Hamilton and Hardy, 1974).
Safety Profile
Moderately toxic by ingestion and skin contact. Mildly toxic by inhalation. Human systemic effects: visual field changes.
Experimental reproductive effects. Mutation data was 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 oxidizing materials. Incompatible with N2O4.
To fight the fire, use CO2, dry chemicals, alcohol foam.
When heated to decomposition it emits toxic fumes of NOx.
Potential Exposure
Triethylamine 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.
TEA is used to solubilize 2,4,5-T in water and serves as a selective extractant in the purification of antibiotics.
It is used to manufacture quaternary ammonia compounds and octadecyloxymethyltriethylammonium chloride; an agent used in textile treatment.
Carcinogenicity
TEA was not mutagenic in bacterial assays, but it did cause aneuploidy and chromosome aberrations in rats.
Environmental Fate
Photolytic. Low et al. (1991) reported that the photooxidation of aqueous tertiary amine solutions by UV light in the presence of titanium dioxide resulted in the formation of ammonium and nitrate ions.
Chemical/Physical. Triethylamine reacted with NOx in the dark to form diethylnitrosamine.
In an outdoor chamber, photooxidation by natural sunlight yielded the following products: diethylnitramine, diethylformamide, diethylacetamide, ethylacetamide, diethylhydroxylamine, ozone, acetaldehyde, and peroxyacetyl nitrate (Pitts et al., 1978).
Metabolism
There have been few studies on the metabolism of industrially important aliphatic amines such as triethylamine.
It 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).
Shipping
UN1296 Triethylamine, Hazard Class: 3; Labels: 3-Flammable liquid, 8-Corrosive material.
Incompatibilities
A strong base. Violent reaction with strong acids; halogenated compounds; and strong oxidizers.
Attacks some forms of plastics, rubber, and coatings.
Corrosive to aluminum, zinc, copper, and their alloys in the presence of moisture.
Reaction with nitrosating agents (e.g., nitrites, nitrous gases, and nitrous acid) is capable of releasing carcinogenic nitrosamines.
Triethylamine Preparation Products And Raw materials:
Raw materials
Ethanol
Diethylamine
KAOLIN
Ethanol 95%
Hydrogen
Triethanolamine
Ammonia
Triethylamine is a weak cohesive and dipolar/polarizable solvent, moderately hydrogen-bond basic and non-hydrogen-bond acidic.
The triethylamine-dimethyl sulfoxide biphasic system has similar selectivity to the isopentyl ether-propylene carbonate biphasic system, the triethylamine-formamide system to octan-1-ol-formamide, and the triethylamine-ethanolamine biphasic system to 1,2-dichloroethane with either ethylene glycol or formamide as counter solvents
Triethylamine is used as a catalytic solvent in chemical syntheses; as an accelerator activator for rubber; as a corrosion inhibitor; as a curing and hardening agent for polymers; as a propellant; in the manufacture of wetting, penetrating, and waterproofing agents of quaternary ammonium compounds; and for the desalination of seawater.
Triethylamine is a base commonly used in organic chemistry to prepare esters and amides from acyl chlorides. Like other tertiary amines,it catalyzes the formation of urethane foams and epoxy resins.
Triethylamine is commonly employed in organic synthesis as a base, most often in the preparation of esters and amides from acyl chlorides.[2] Such reactions lead to the production of hydrogen chloride which combines with triethylamine 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, it catalyzes the formation of urethane foams and epoxy resins. It is also useful in dehydrohalogenation reactions and Swern oxidations.
Triethylamine is readily alkylated to give the corresponding quaternary ammonium salt:
RI + Et3N → Et3NR+I-
A tertiary amine that is ammonia in which each hydrogen atom is substituted by an ethyl group.
IUPAC Name
N,N-diethylethanamine
Synonyms Sources
(C2H5)3N NIST Chemistry WebBook Indicates when synonyms have been adapted from the specified source i.e. not exact copies.
(diethylamino)ethane NIST Chemistry WebBook Indicates when synonyms have been adapted from the specified source i.e. not exact copies.
N,N,N-triethylamine NIST Chemistry WebBook Indicates when synonyms have been adapted from the specified source i.e. not exact copies.
N,N-Diethylethanamine KEGG COMPOUND
NEt3 IUPAC
TEA
Note: (2011-11-28) Note that TEA is also commonly used as an abbreviation for triethanolamine.
ChemIDplus
TEN ChemIDplus
Triäthylamin Deutsch ChEBI
Triethylamin Deutsch ChEBI
Triethylamine
Triethylamine
N,N-Diethylethanamine
Ethanamine, N,N-diethyl-
121-44-8
Ethanamine, N,N-diethyl-
(Diethylamino)ethane
N,N-Diethylethanamine
TRIETHYLAMIN
Triethylamine
trietilamina
UN 1296
EINECS 204-469-4
UNII-VOU728O6AY
(C2H5)3N
N,N,N-triethylamine
NEt3
TEA
TEN
Triethylamine is a colorless, highly volatile, extremely flammable liquid, that is not soluble in water but is well soluble in the most organic solvents.
It has a strong unpleasant fish odor.
Method of obtaining
Triethylamine is obtained by the alkylation of ammonia with ethanol.
Application
Triethylamine is a commonly used base agent in the synthesis of organic compounds.
It is also used in preparing amides and esters from acyl chlorides.
It is used as a catalyst in producing polyurethane foams and epoxy resins.
It is also useful in the dehydrohalogenation reaction and the oxygenation processes.
It is an intermediate compound in producing drugs, pesticides and other chemicals.
Storage and transport
Triethyloamine should be stored in a cool, dry and well-ventilated place away from any ignition sources, sunlight, electricity sources, in tightly sealed containers.
For transport purposes, it is classified as ADR (ADR classification code: FC, RID/ADR class: 3, hazard label: 3.8, number UN 1296).
triethylamin (cs)
triethylamin (da)
Triethylamin (de)
triethylamine (nl)
trietil-amin (hu)
trietilamin (hr)
trietilamin (sl)
trietilamina (es)
trietilamina (it)
trietilamina (pt)
trietilamina (ro)
trietilaminas (lt)
trietilamīns (lv)
trietylamin (no)
trietylamin (sv)
trietylamín (sk)
trietyloamina (pl)
trietyyliamiini (fi)
Trietüülamiin (et)
triéthylamine (fr)
τριαιθυλαμίν (el)
триетиламин (bg)
CAS names
Ethanamine, N,N-diethyl-
Other
IUPAC names
Ethanamine,N,N-diethl
Ethanamine,N,N-diethyl
N,N,N,triethylamine
N,N-Diethylethanamine
N,N-diethylethanamine
N,N-diethylethanamine
TEA
TRIETHYL AMINE
Triethylamin
TRIETHYLAMINE
Triethylamine
triethylamine
Triethylamine
triethylamine
Trade names
(Diethylamino)ethane
(diethylamino)ethane
ethanamine, N,N-diethyl-
Ethanamine, N,N-diethyl- (9CI)
MISSION MODELS POLYURETHANE MIX ADDITIVE
N,N-Diethylethanamine
TEA
Triethylamin
TRIETHYLAMINE
Triethylamine
Triethylamine (7CI, 8CI)