Names | |||
---|---|---|---|
Preferred IUPAC name N,N-Diethylethanamine | |||
Other names (Triethyl)amine Triethylamine (no longer IUPAC name [1] ) | |||
Identifiers | |||
3D model (JSmol) | |||
Abbreviations | TEA [2] | ||
605283 | |||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.004.064 | ||
EC Number |
| ||
KEGG | |||
MeSH | triethylamine | ||
PubChem CID | |||
RTECS number |
| ||
UNII | |||
UN number | 1296 | ||
CompTox Dashboard (EPA) | |||
| |||
| |||
Properties [3] | |||
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 | ||
112.4 g/L at 20 °C [4] | |||
Solubility | miscible with organic solvents | ||
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) [5] | ||
-81.4·10−6 cm3/mol | |||
Refractive index (nD) | 1.401 | ||
Thermochemistry | |||
Heat capacity (C) | 216.43 J K−1 mol−1 | ||
Std enthalpy of formation (ΔfH⦵298) | −169 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) | −4.37763 to −4.37655 MJ mol−1 | ||
Hazards | |||
GHS labelling: | |||
Danger | |||
H225, H302, H312, H314, H332 | |||
P210, P280, P305+P351+P338, P310 | |||
NFPA 704 (fire diamond) | |||
Flash point | −15 °C (5 °F; 258 K) | ||
312 °C (594 °F; 585 K) | |||
Explosive limits | 1.2–8% | ||
Threshold limit value (TLV) | 2 ppm (8 mg/m3) (TWA), 4 ppm (17 mg/m3) (STEL) | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
| ||
LCLo (lowest published) | 1425 ppm (mouse, 2 hr) [6] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible) | TWA 25 ppm (100 mg/m3) [7] | ||
REL (Recommended) | None established [7] | ||
IDLH (Immediate danger) | 200 ppm [7] | ||
Related compounds | |||
Related amines | |||
Related compounds | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et 3N. 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. [8] [9] It 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 is prepared by the alkylation of ammonia with ethanol: [10]
The pKa of protonated triethylamine is 10.75, [5] 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. [4] 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 acids, such as I2 and phenols. Owing to its steric bulk, it forms complexes with transition metals reluctantly. [12] [13] [14]
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. [15] Such reactions lead to the production of hydrogen chloride which combines with triethylamine to form the salt triethylamine hydrochloride, commonly called triethylammonium chloride. (R, R' = alkyl, aryl):
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:
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 commonly used in the production of anionic PUDs. A polyurethane prepolymer is prepared using an isocyanate and polyol with dimethylol propionic acid (DMPA). This molecule contains two hydroxy groups and a carboxylic acid group. This prepolymer is then dispersed in water with triethylamine or other neutralizing agent. The TEA reacts with the carboxylic acid forming a salt which is water soluble. Usually, a diamine chain extender is then added to produce a polyurethane dispersed in water with no free NCO groups but with polyurethane and polyurea segments. [16] [17] [18] Dytek A is commonly used as a chain extender. [19]
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.
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. [20] The Soviet "Scud" Missile used TG-02 ("Tonka-250"), a mixture of 50% xylidine and 50% triethylamine as a starting fluid to ignite its rocket engine. [21]
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. Due to the scent, it is considered unlucky in British culture to bring hawthorn into a house. Gangrene and semen are also said to possess a similar odour. [22]
In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.
The ammonium cation is a positively charged polyatomic ion with the chemical formula NH+4 or [NH4]+. It is formed by the protonation of ammonia. Ammonium is also a general name for positively charged (protonated) substituted amines and quaternary ammonium cations, where one or more hydrogen atoms are replaced by organic or other groups.
In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group. The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH3CH2C≡N is called "propionitrile". The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.
In chemistry, a hydrochloride is an acid salt resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base. An alternative name is chlorhydrate, which comes from French. An archaic alternative name is muriate, derived from hydrochloric acid's ancient name: muriatic acid.
In organic chemistry, a carbamate is a category of organic compounds with the general formula R2NC(O)OR and structure >N−C(=O)−O−, which are formally derived from carbamic acid. The term includes organic compounds, formally obtained by replacing one or more of the hydrogen atoms by other organic functional groups; as well as salts with the carbamate anion H2NCOO−.
Tetraethylammonium (TEA) is a quaternary ammonium cation with the chemical formula [Et4N]+, consisting of four ethyl groups attached to a central nitrogen atom. It is a counterion used in the research laboratory to prepare lipophilic salts of inorganic anions. It is used similarly to tetrabutylammonium, the difference being that its salts are less lipophilic, more easily crystallized and more toxic.
Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.
Polyurea is a type of elastomer that is derived from the reaction product of an isocyanate component and an amine component. The isocyanate can be aromatic or aliphatic in nature. It can be monomer, polymer, or any variant reaction of isocyanates, quasi-prepolymer or a prepolymer. The prepolymer, or quasi-prepolymer, can be made of an amine-terminated polymer resin, or a hydroxyl-terminated polymer resin.
In organic chemistry, quaternary ammonium cations, also known as quats, are positively-charged polyatomic ions of the structure [NR4]+, where R is an alkyl group, an aryl group or organyl group. Unlike the ammonium ion and the primary, secondary, or tertiary ammonium cations, the quaternary ammonium cations are permanently charged, independent of the pH of their solution. Quaternary ammonium salts or quaternary ammonium compounds are salts of quaternary ammonium cations. Polyquats are a variety of engineered polymer forms which provide multiple quat molecules within a larger molecule.
In chemistry, the term phosphonium describes polyatomic cations with the chemical formula PR+
4. These cations have tetrahedral structures. The salts are generally colorless or take the color of the anions.
DABCO (1,4-diazabicyclo[2.2.2]octane), also known as triethylenediamine or TEDA, is a bicyclic organic compound with the formula N2(C2H4)3. This colorless solid is a highly nucleophilic tertiary amine base, which is used as a catalyst and reagent in polymerization and organic synthesis.
N,N-Diisopropylethylamine, or Hünig's base, is an organic compound that is a tertiary amine. It is named after the German chemist Siegfried Hünig. It is used in organic chemistry as a non-nucleophilic base. It is commonly abbreviated as DIPEA,DIEA, or i-Pr2NEt.
In organic chemistry, the Menshutkin reaction converts a tertiary amine into a quaternary ammonium salt by reaction with an alkyl halide. Similar reactions occur when tertiary phosphines are treated with alkyl halides.
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.
Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.
In chemistry, aminolysis (/am·i·nol·y·sis/) is any chemical reaction in which a molecule is lysed by reacting with ammonia or an amine. The case where the reaction involves ammonia may be more specifically referred to as ammonolysis.
Amine alkylation (amino-dehalogenation) is a type of organic reaction between an alkyl halide and ammonia or an amine. The reaction is called nucleophilic aliphatic substitution, and the reaction product is a higher substituted amine. The method is widely used in the laboratory, but less so industrially, where alcohols are often preferred alkylating agents.
Tetraethylammonium chloride (TEAC) is a quaternary ammonium compound with the chemical formula [N(CH2CH3)4]+Cl−, sometimes written as [NEt4]Cl. In appearance, it is a hygroscopic, colorless, crystalline solid. It has been used as the source of tetraethylammonium ions in pharmacological and physiological studies, but is also used in organic chemical synthesis.
Tetraethylammonium iodide is a quaternary ammonium compound with the chemical formula C8H20N+I−. It has been used as the source of tetraethylammonium ions in pharmacological and physiological studies, but is also used in organic chemical synthesis.
In chemistry, a fatty amine is loosely defined as any amine possessing a mostly linear hydrocarbon chain of eight or more carbon atoms. They are typically prepared from the more abundant fatty acids, with vegetable or seed-oils being the ultimate starting material. As such they are often mixtures of chain lengths, ranging up to about C22. They can be classified as oleochemicals. Commercially important members include coco amine, oleylamine, tallow amine, and soya amine. These compounds and their derivatives are used as fabric softeners, froth flotation agents, corrosion inhibitors, lubricants and friction modifiers. They are also the basis for a variety of cosmetic formulations.
{{cite book}}
: CS1 maint: location missing publisher (link) CS1 maint: multiple names: authors list (link)