TRIETHYLAMINE

CAS NO:121-44-8
EC NO:204-469-4

Triethylamine is 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, usually as a base, in organic synthesis.

Properties
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; −174.46 °F; 158.45 K
Boiling point    88.6 to 89.8 °C; 191.4 to 193.5 °F; 361.7 to 362.9 K
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

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 acid 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. 
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.

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.

Natural occurrence
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.

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.

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 of wetting, penetrating, and waterproofing agents of quaternary ammonium compounds; and for the desalination of seawater.
-CHEMICAL INTERMEDIATE; ANTI-LIVERING AGENT FOR UREA & MELAMINE BASED ENAMELS; RECOVERY OF GELLED PAINT VEHICLES; CATALYST FOR POLYURETHANE FOAMS; FLUX FOR COPPER SOLDERING
-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.
-Catalyst for epoxy resins

Industry Uses    
Adhesives and sealant chemicals
Intermediates
Paint additives and coating additives not described by other categories
Photosensitive chemicals
Process regulators
Processing aids, not otherwise listed

Consumer Uses    
Adhesives and sealants
Building/construction materials not covered elsewhere
Formulated into Surface Active Agent
Fuels and related products
Paints and coatings
Personal care products
Photographic supplies, film, and photo chemicals
Plastic and rubber products not covered elsewhere

Industry Processing Sectors
Adhesive manufacturing
All other basic organic chemical manufacturing
All other chemical product and preparation manufacturing
Computer and electronic product manufacturing
Fabricated metal product manufacturing
Miscellaneous manufacturing
Organic fiber manufacturing
Paint and coating manufacturing
Pesticide, fertilizer, and other agricultural chemical manufacturing
Petrochemical manufacturing
Pharmaceutical and medicine manufacturing
Photographic film paper, plate, and chemical manufacturing
Plastic material and resin manufacturing
Plastics product manufacturing
Primary metal manufacturing
Rubber product manufacturing
Soap, cleaning compound, and toilet preparation manufacturing
Synthetic dye and pigment manufacturing
Textiles, apparel, and leather manufacturing
Wholesale and retail trade

IDENTIFICATION AND USE: Triethylamine (TEA) is a colorless liquid. 
Triethylamine is used as catalytic solvent in chemical synthesis; accelerator activators for rubber; wetting, penetrating, and waterproofing agents of quaternary ammonium types; curing and hardening of polymers; corrosion inhibitor; propellant.

Triethylamine is a mobile-phase modifier in RP-HPLC separation of acidic, basic, and neutral drugs. Improves resolution of amino acids and amino acid amides by HPLC by suppressing tailing. 
Triethylamine is commonly employed in organic synthesis in the preparation of esters and amides from acyl chlorides. 
Triethylamine is also useful in dehydrohalogenation reactions and Swern oxidations.

Formula: C6H15N / (C2H5)3N
Molecular mass: 101.2
Boiling point: 89°C
Melting point: -115°C
Relative density (water = 1): 0.7
Solubility in water, g/100ml at 20°C: 17 (good)
Vapour pressure, kPa at 20°C: 7.2
Relative vapour density (air = 1): 3.5
Relative density of the vapour/air-mixture at 20°C (air = 1): 1.2
Flash point: -17°C c.c.
Auto-ignition temperature: 230°C
Explosive limits, vol% in air: 1.2-8
Octanol/water partition coefficient as log Pow: 1.45  

Product description
Triethylamine (TEA) is a colorless liquid with an ammonia-like odor.

Applications/uses
Ag chem solvents
Agriculture intermediates
Aluminum production
Chemicals & petrochemicals
Electronic chemicals
Insecticides int
Intermediates
Mining
Pharmaceutical chemicals
Resins

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 neutralizer 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 automotive casting industry and textile industry.

Formula
C6H15N
Formula Weight
101.19
Melting point
-115°
Boiling Point
89-90°
Flash Point
-11°(12°F)
Density
0.726
Refractive Index
1.4005
Storage & Sensitivity
Ambient temperatures.
Solubility
Miscible with water, ether and ethanol.

Triethylamine is a water-soluble flammable liquid tertiary amine (C2H5)3N that is used chiefly in synthesis (as of quaternary ammonium compounds)

Application    
Pharmaceuticals&subquo; Dyes & pigments&subquo; Rubber chemicals&subquo; Agricultural Chemicals&subquo; Surfactant&subquo; Paints & varnishes&subquo; Paint removers

General description
Triethylamine (TEA, Et3N) is an aliphatic amine. Its 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 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 the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. 
Triethylamine is a commonly encountered in organic synthesis probably because it is the simplest symmetrically trisubstituted amine, i.e. a tertiary amine, that is liquid at room temperature. 
Triethylamine possesses a strong fishy odor reminiscent of ammonia. Diisopropylethylamine (Hünig’s base, CAS # 7087-68-5) is a widely used relative of triethylamine. 
Triethylamine is also the smell of the hawthorn plant, and semen, among others 

Triethylamine is a tertiary amine which is abbreviated as TEA. It is a colorless liquid and is commonly used in organic synthesis. VWR offers high purity triethylamine in a variety of capacities safely stored in amber glass bottles.

Outline
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. 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.

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.

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.

Chemical Properties
Triethylamine is a colorless liquid. Strong ammonia odor.

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 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.

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.

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). 
Triethylamine 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). 

About this substance
Triethylamine is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 000 to < 100 000 tonnes per annum.

Triethylamine is used in articles, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.

Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which this substance is most likely to be released to the environment.

Article service life
Other release to the environment of Triethylamine is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials) and indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment).
Triethylamine can be found in products with material based on: leather (e.g. gloves, shoes, purses, furniture).

Widespread uses by professional workers
Triethylamine 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.
Triethylamine is used for the manufacture of: chemicals, pulp, paper and paper products and rubber products.
Release to the environment of Triethylamine 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 Triethylamine 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.

Formulation or re-packing
Triethylamine is used in the following products: polymers, metal working fluids, pH regulators and water treatment products, lubricants and greases, coating products, laboratory chemicals, adhesives and sealants, metal surface treatment products and paper chemicals and dyes.
Release to the environment of Triethylamine can occur from industrial use: formulation of mixtures, formulation in materials, manufacturing of the substance and in the production of articles.

Uses at industrial sites
Triethylamine is 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.
Triethylamine has an industrial use resulting in manufacture of another substance (use of intermediates).
Triethylamine is used in the following areas: mining.
Triethylamine is used for the manufacture of: chemicals, textile, leather or fur, rubber products, plastic products and fabricated metal products.
Release to the environment of Triethylamine 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.

Manufacture
Release to the environment of Triethylamine can occur from industrial use: manufacturing of the substance, formulation of mixtures and in processing aids at industrial sites.

polymers
Triethylamine  is used to give larger masses to certain particulars in its nucleophilicity, which are used for them. For example, it is part of the synthesis of polycarbonate jams, polyurethane columns and epoxy jams.

Chromatography
Triethylamine s remote amphilicity and volatility allow its derivatized salts to be used for use in utility chromatography. Another implicit use of triethylamine is that various aged amine salts such as triethylamine bicarbonate, NHEt, 3HCO3 (or TEAB).

Commercial Products
Cigarettes and tobacco, food preservatives, floor cleaners, sweeteners, pesticides, colorants, etc. It has been used as a regulation in formulations.

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

SYNONYMS:
(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]
66688-79-7 [RN]
73602-61-6 [RN]
diethylaminoethane
MFCD00008591 [MDL number]
N,N-Diethyl-Ethanamine
Triaethylamin [German]
Triaethylamin
Triethylamin
Triethyl-amine
triethylammonium