TRIETHYLAMINE

Cas no : 121-44-8
N,N-Diethylethanamine;Ethanamine, N,N-diethyl-(Diethylamino)ethane;Triethylamin;triethyl amine;Triaethylamin;Trietilamina;N,N,N-Triethylamine;NEt3;trietylamine;Triaethylamin [German];Trietilamina [Italian];triethyl-amine;tri-ethyl amine;Et3N;N,N-diethyl-ethanamine;EINECS 204-469-4;UN1296;AI3-15425;CHEBI:35026;Triethylamine, 99.7%, extra pure;Triethylamine [UN1296] [Flammable liquid];Diethylaminoethane;Triethylamine, for analysis;Triethylamine, 99%, pure;Triethylamine, >=99.5%; triethylamine; ethanamine; n,n-diethyl; diethylamino ethane; triaethylamin; triethylamin; trietilamina; triethyl amine; n,n,n-triethylamine; net3; diethylaminoethane
triehtylamineTriethylamine 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.[7][8] 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 is prepared by the alkylation of ammonia with ethanol:[9]
NH3 + 3 C2H5OH → N(C2H5)3 + 3 H2O
Triethylamine, 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. Triethylamine is a very strong basic compound (based on its pKa). Triethylamine is an ammoniacal and fishy tasting compound.
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.[10] 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.[11]
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, it is commonly used as a base during the preparation of esters and amides from acyl chlorides.[12] 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.
Triethylamine is used to give salts of various carboxylic acid-containing pesticides, e.g. Triclopyr and 2,4-dichlorophenoxyacetic acid[citation needed]
Triethylamine is the active ingredient in FlyNap, a product for anesthetizing Drosophila melanogaster.[citation needed] 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.[13]
Hawthorn flowers have a heavy, complicated scent, the distinctive part of which is triethylamine, which is also one of the first chemicals produced by a dead human body when it begins to decay. For this reason, it is considered as unlucky to bring Hawthorn (or May blossom) into the house. Gangrene is also said to possess a similar odour. On a brighter note, it is also described as 'the smell of sex', specifically of semen.[14]
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.
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.
Hazard Summary
Acute (short-term) exposure of humans to triethylamine vapor causes eye irritation, corneal swellng, 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 membranesin humans.  Chronic (long-term) exposure f workers to triethylamine vapor has been observed to causereversible 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.
Please Note: The main source of information for this fact sheet is EPA's Integrated Risk Information System (IRIS)(2), which contains information on inhalation chronic toxicity of triethylamine and the RfC.
Uses
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 ofwetting, penetrating, and waterproofing agents of quaternary ammonium compounds; and for the desalination of seawater. (1,3)
Sources and Potential Exposure
Occupational exposure may occur primarily via inhalation and dermal contact during its manufacture and use. (1)
The general population may be exposed to triethylamine from ingesting contaminated food; triethylamine has been identified in broiled beef. (1)
Assessing Personal Exposure
No information was located regarding the measurement of personal exposure to triethylamine.
Health Hazard Information
Acute Effects:
Acute 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. (1,2)
Acute exposure can irritate the skin and mucous membranes in humans. (1,3)
Acute animal tests in rats, mice, and rabbits, have demonstrated triethylamine to have moderate acute toxicity from inhalation, moderate to high acute toxicity from oral exposure, and high acute toxicity from dermal exposure. (4)
Chronic Effects (Noncancer):
Chronic exposure of workers to triethylamine vapor has been observed to cause reversible corneal edema.
Chronic exposure of workers to triethylamine vapor has been observed to cause reversible corneal edema.
(1,2)
Chronic inhalation exposure has resulted in inflammation of the nasal passage in rats.Thickening of the interalveolar walls of the lungs, mucous accumulation in the alveolar spaces of the lungs, and hematological effects have also been reported in rats chronically exposed by inhalation. (2)
Chronic inhalation exposure of rabbits has been reported to cause irritation of the lungs, edema, moderate peribronchitis, vascular thickening, eye lesions, and, at higher levels, liver, kidney, and heart eff 3 ects. (2)
The Reference Concentration (RfC) for triethylamine is 0.007 milligrams per cubic meter (mg/m ) based on inflammation of the nasal passages in rats. The RfC is an estimate (with uncertainty spanning perhaps an order of magnitude) of a continuous inhalation exposure to the human population (including sensitive
subgroups) that is likely to be without appreciable risk of deleterious noncancer effects during a lifetime. It is not a direct estimator of risk but rather a reference point to gauge the potential effects.  At exposures increasingly greater than the RfC, the potential for adverse health effects increases.  Lifetime exposure
above the RfC does not imply that an adverse health effect would necessarily occur. (2)
EPA has medium confidence in the studies on which the RfC was based because a concentration-response was evident, although a lowest-observed-adverse-effect level (LOAEL) could not be identified and a second species was not used; low confidence in the database as only a single reproductive/developmental study
exists, hich is by the oral route and is therefore not useful for inhalation risk assessment, and no chronic studies exist; and, consequently, low confidence in the RfC. (2)EPA has not established a Reference Dose (RfD) for triethylamine. (2)
Reproductive/Developmental Effects:
No information is available on the reproductive or developmental effects of triethylamine in humans.
No reproductive or developmental effects were reported in a 3-generation study in rats exposed to triethylamine in drinking water; however, this study had limitations. (2)
Cancer Risk:
No information is available on the carcinogenic effects of triethylamine in humans or animals.
EPA has not classified triethylamine with respect to potential carcinogenicity. (2)
Physical Properties
The chemical formula for triethylamine is C6 H1 N5, and its molecular weight is 101.19 g/mol. (3)
Triethylamine occurs as a colorless flammable liquid that is slightly soluble in water. (1,3,5)
Triethylamine has a strong fishy ammonia-like odor, with an odor threshold of 0.48 parts per million (ppm). (1,3,5)
The vapor pressure for triethylamine is 400 mm Hg at 31.5 °C, and its log octanol/water partition coefficient (log Kow) is 1.45. (1)
Triethylamine Formula
Triethylamine (also know as TEA) is an organic base used in organic synthesis. It is largely used in esters and amides synthesis from acyl chlorides.
Formula and structure: The chemical and molecular formula of triethylamine are N(CH2CH3)3 and C6H15N, respectively. It is also represented as Et3N and its molecular mass is 101.19 g mol-1. Triethylamine is a tertiary amine consisting in three ethyl groups (-CH2CH3) linked to a nitrogen atom (N). Its chemical structure can be written as below, in the common representations used for organic molecules.
Occurrence: Triethylamine is not easily found in nature. However, it is present in some living organism as xenobiotic compounds. These organisms catalyze the excretion trough monoamine oxidase enzymes, through deamination processes.
Preparation: Triethylamine can be prepared by various methods. However, the most extended method is the alkylation of ammonia with ethanol, in the presence of hydrogen and Cu-Ni catalyst:
NH3 + 3 C2H5OH → N(C2H5)3 + 3 H2O
Ethylamine and diethylamine are secondary products of this reaction. Triethylamine can also be synthesized from acetaldehyde, ammonia and hydrogen, through hydrogenation catalyst.
Physical properties: It is a colorless volatile liquid with a fishy and ammoniacal odor. Its density is 0.726 g mL-1 and its boiling point is 88.8 ºC. It is slightly soluble in water at 20 ºC. It is soluble in ethanol, carbon tetrachloride and ethyl ether and very soluble in acetone, benzene and chloroform.
Chemical properties: Triethylamine is an aliphatic amine considered a weak base (pKah is 10.75). Triethylamine is widely used in organic syntheses due its the most simple tri-substituted uniformly amines liquid (trimethylamine is a colorless gas at room temperature). Triethylamine emits toxic vapors of nitrogen oxides when heated.
Uses: Triethylamine is used as organic base, removing the hydrogen from the secondary amine, in the synthesis of esters and amides from acyl chlorides. The reaction products include a quaternary ammonium salt:
R2NH + R'C(O)Cl + Et3N → R'C(O)NR2 + Et3NH+Cl-
Triethylamine is use to manufacture a great variety of chemical compounds like fuels, aditives, intermediats, preservatives, surfactants and fungicides.
Health effects/safety hazards: Triethylamine is extremely flammable and corrosive. Moreover, it forms explosive mixtures with air. Triethylamine can burn skin, eyes and respiratory system. It is incompatible with strong oxidizers, strong acids and halogenated compounds.
Hazard statements:
H225 Highly flammable liquid and vapor.
H302 Harmful if swallowed.
H311 Toxic in contact with skin.
H331 Toxic if inhaled.
H314 Causes severe skin burns and eye damage.
H335 May cause respiratory irritation.
Precautionary statements:
Prevention:
P210 Keep away from heat / sparks / open flames / hot surfaces. No smoking.
P280 Wear protective gloves / protective clothing / eye protection / face protection.
P260 Do not breathe dust / smoke / gas / mist / vapor / spray.
Intervention:
P303 + P361 + P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse your skin with water / shower.
P304 + P340 IF INHALED: Remove injured person to fresh air and keep in a comfortable position for easy breathing.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for a few minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P310 Immediately call the NATIONAL POISON CONSULTANCY NUMBER 114 or the doctor / physician.
Storage:
P403 + P233 Store in a well-ventilated area. Keep container tightly closed.
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.[12] 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