Triethylamine

Last updated
Triethylamine
Et3N showing pyramidal-ness.svg
Ball and stick model of triethylamine Triethylamine-3D-balls.png
Ball and stick model of triethylamine
Spacefill model of triethylamine Triethylamine-3D-vdW.png
Spacefill model of triethylamine
Names
Preferred IUPAC name
N,N-Diethylethanamine
Other names
(Triethyl)amine
Triethylamine (no longer IUPAC name [1] )
Identifiers
3D model (JSmol)
AbbreviationsTEA [2]
605283
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.064 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-469-4
KEGG
MeSH triethylamine
PubChem CID
RTECS number
  • YE0175000
UNII
UN number 1296
  • InChI=1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3 Yes check.svgY
    Key: ZMANZCXQSJIPKH-UHFFFAOYSA-N Yes check.svgY
  • CCN(CC)CC
Properties [3]
C6H15N
Molar mass 101.193 g·mol−1
AppearanceColourless 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
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
1.401
Thermochemistry
216.43 J K−1 mol−1
−169 kJ mol−1
−4.37763 to −4.37655 MJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H225, H302, H312, H314, H332
P210, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
3
0
Flash point −15 °C (5 °F; 258 K)
312 °C (594 °F; 585 K)
Explosive limits 1.2–8%
2 ppm (8 mg/m3) (TWA), 
4 ppm (17 mg/m3) (STEL)
Lethal dose or concentration (LD, LC):
  • 580 mg kg−1(dermal, rabbit)
  • 730 mg kg−1(oral, rat)
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Synthesis and properties

Triethylamine is prepared by the alkylation of ammonia with ethanol: [10]

NH3 + 3 C2H5OH → N(C2H5)3 + 3 H2O

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]

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. [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):

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 commonly used in the production of anionic Polyurethane dispersions (resins dispersed in water rather than solvents) as a neutralizing agent.

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 fruit flies.[ citation needed ] It is also 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.[ citation needed ][ how? ]

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 discovered by the Germans during the early 1940s to be hypergolic in combination with nitric acid, and was used as a component in the German Wasserfall rocket. [16] The Soviet Scud missile used TONKA-250, a mixture of 50% xylidine and 50% triethylamine as a starting fluid to ignite its rocket engine. [17] [ better source needed ]

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. 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. [18]

Related Research Articles

<span class="mw-page-title-main">Amine</span> Chemical compounds and groups containing nitrogen with a lone pair (:N)

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Formally, amines are 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.

<span class="mw-page-title-main">Ammonium</span> Chemical compound

Ammonium is a modified form of ammonia that has an extra hydrogen atom. It is a positively charged (cationic) molecular ion with the chemical formula NH+4 or [NH4]+. It is formed by the addition of a proton to 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. Not only is ammonium a source of nitrogen and a key metabolite for many living organisms, but it is an integral part of the global nitrogen cycle. As such, human impact in recent years could have an effect on the biological communities that depend on it.

<span class="mw-page-title-main">Hydrochloride</span> Any salt of an organic base and hydrochloric acid

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.

<span class="mw-page-title-main">Methylamine</span> Organic chemical compound

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.

<span class="mw-page-title-main">Quaternary ammonium cation</span> Polyatomic ions of the form N(–R)₄ (charge +1)

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.

<span class="mw-page-title-main">Phosphonium</span> Family of polyatomic cations containing phosphorus

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.

Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH. This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, treating morpholine with hydrochloric acid generates the salt morpholinium chloride. It is a colorless liquid with a weak, ammonia- or fish-like odor. The naming of morpholine is attributed to Ludwig Knorr, who incorrectly believed it to be part of the structure of morphine.

<span class="mw-page-title-main">Dimethylamine</span> Chemical compound

Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

<i>N</i>,<i>N</i>-Diisopropylethylamine Chemical compound

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.

<span class="mw-page-title-main">Ethylenediamine</span> Chemical compound

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.

<span class="mw-page-title-main">Ethylamine</span> Chemical compound

Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

<span class="mw-page-title-main">Diethylamine</span> Chemical compound

Diethylamine is an organic compound with the formula (CH3CH2)2NH. It is a secondary amine. It is a flammable, weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear brown due to impurities. It has a strong ammonia-like odor.

<span class="mw-page-title-main">Sulfamide</span> Organosulfur compound

Sulfamide is a compound with the chemical formula SO2(NH2)2 and structure H2N−S(=O)2−NH2. Sulfamide is produced by the reaction of sulfuryl chloride with ammonia. Sulfamide was first prepared in 1838 by the French chemist Henri Victor Regnault.

In chemistry, work-up refers to the series of manipulations required to isolate and purify the product(s) of a chemical reaction. The term is used colloquially to refer to these manipulations, which may include:

<span class="mw-page-title-main">Potassium tetrachloroplatinate</span> Chemical compound

Potassium tetrachloroplatinate(II) is the chemical compound with the formula K2PtCl4. This reddish orange salt is an important reagent for the preparation of other coordination complexes of platinum. It consists of potassium cations and the square planar dianion PtCl42−. Related salts are also known including Na2PtCl4, which is brown-colored and soluble in alcohols, and quaternary ammonium salts, which are soluble in a broader range of organic solvents.

<span class="mw-page-title-main">Tetramethylammonium chloride</span> Chemical compound

Tetramethylammonium chloride is one of the simplest quaternary ammonium salts, with four methyl groups tetrahedrally attached to the central N. The chemical formula (CH3)4N+Cl− is often abbreviated further as Me4N+Cl−. It is a hygroscopic colourless solid that is soluble in water and polar organic solvents. Tetramethylammonium chloride is a major industrial chemical, being used widely as a chemical reagent and also as a low-residue bactericide in such processes as hydrofracking. In the laboratory, it has fewer synthetic chemical applications than quaternary ammonium salts containing longer N-alkyl substituents, which are used extensively as phase-transfer catalysts.

<span class="mw-page-title-main">Tetraethylammonium chloride</span> Chemical compound

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.

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.

References

  1. ↑ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 671. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.
  2. ↑ X. Bories-Azeau, S. P. Armes, and H. J. W. van den Haak, Macromolecules 2004, 37, 2348 PDF
  3. ↑ The Merck Index (11th ed.). 9582.
  4. 1 2 "MSDS - 471283". www.sigmaaldrich.com. Retrieved 2020-06-17.
  5. 1 2 David Evans Research Group Archived 2012-01-21 at the Wayback Machine
  6. ↑ "Triethylamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  7. 1 2 3 NIOSH Pocket Guide to Chemical Hazards. "#0633". National Institute for Occupational Safety and Health (NIOSH).
  8. ↑ "Ethanolamine Compounds (MEA, DEA, TEA And Others)". Safe Cosmetics. Retrieved 2020-06-17.
  9. ↑ "tetraethylammonium | Ligand page | IUPHAR/BPS Guide to PHARMACOLOGY". www.guidetopharmacology.org. Retrieved 2020-06-17.
  10. ↑ Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). Amines, Aliphatic. doi:10.1002/14356007.a02_001. ISBN   3-527-30673-0.
  11. ↑ F., Armarego, W. L. (2012-10-17). Purification of Laboratory Chemicals. Chai, Christina Li Lin (Seventh ed.). Amsterdam. ISBN   978-0-12-382162-1. OCLC   820853648.{{cite book}}: CS1 maint: location missing publisher (link) CS1 maint: multiple names: authors list (link)
  12. ↑ DeLaive, Patricia J.; Sullivan, B. P.; Meyer, T. J.; Whitten, D. G. (July 1979). "Applications of light-induced electron-transfer reactions. Coupling of hydrogen generation with photoreduction of ruthenium(II) complexes by triethylamine". Journal of the American Chemical Society. 101 (14): 4007–4008. doi:10.1021/ja00508a070. ISSN   0002-7863.
  13. ↑ DeLaive, Patricia J.; Foreman, Thomas K.; Giannotti, Charles; Whitten, David G. (August 1980). "Photoinduced electron transfer reactions of transition-metal complexes with amines. Mechanistic studies of alternate pathways to back electron transfer". Journal of the American Chemical Society. 102 (17): 5627–5631. doi:10.1021/ja00537a037. ISSN   0002-7863.
  14. ↑ Seligson, Allen L.; Trogler, William C. (March 1991). "Cone angles for amine ligands. X-ray crystal structures and equilibrium measurements for ammonia, ethylamine, diethylamine, and triethylamine complexes with the [bis(dimethylphosphino)ethane]methylpalladium(II) cation". Journal of the American Chemical Society. 113 (7): 2520–2527. doi:10.1021/ja00007a028. ISSN   0002-7863.
  15. ↑ Sorgi, K. L. (2001). "Triethylamine". Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/047084289X.rt217. ISBN   978-0-471-93623-7.
  16. ↑ Clark, John Drury (23 May 2018). Ignition!: An Informal History of Liquid Rocket Propellants. Rutgers University Press. p. 302. ISBN   978-0-8135-9918-2.
  17. ↑ Brügge, Norbert (24 February 2020). "The Soviet "Scud" missile family". b14643.de. Retrieved 29 July 2022.
  18. ↑ The book of general ignorance. John Lloyd & John Mitchinson. Faber & Faber 2006, The Hawthorn, BBC
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