Triethylamine

Triethylamine
Ball and stick model of triethylamine	Spacefill model of triethylamine
Names
	Preferred IUPAC name N,N-Diethylethanamine
	Other names (Triethyl)amine; Triethylamine (no longer IUPAC name)
Identifiers
CAS Number	121-44-8 ;
3D model (JSmol)	Interactive image;
Abbreviations	TEA
Beilstein Reference	605283
ChEBI	CHEBI:35026 ;
ChEMBL	ChEMBL284057 ;
ChemSpider	8158 ;
ECHA InfoCard	100.004.064
EC Number	204-469-4;
KEGG	C14691 ;
MeSH	triethylamine
PubChem CID	8471;
RTECS number	YE0175000;
UNII	VOU728O6AY ;
UN number	1296
CompTox Dashboard (EPA)	DTXSID301024181 DTXSID3024366, DTXSID301024181 ;
	InChI InChI=1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3 Key: ZMANZCXQSJIPKH-UHFFFAOYSA-N ;
	SMILES CCN(CC)CC;
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
Solubility in water	112.4 g/L at 20 °C
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)
Magnetic susceptibility (χ)	-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:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H312, H314, H332
Precautionary statements	P210, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)	3 3 0
Flash point	−15 °C (5 °F; 258 K)
Autoignition; temperature	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)	580 mg kg−1 (dermal, rabbit); 730 mg kg−1 (oral, rat);
LCLo (lowest published)	1425 ppm (mouse, 2 hr)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 25 ppm (100 mg/m3)
REL (Recommended)	None established
IDLH (Immediate danger)	200 ppm
Related compounds
Related amines	Dimethylamine; Trimethylamine; N-Nitrosodimethylamine; Diethylamine; Diisopropylamine; Dimethylaminopropylamine; Diethylenetriamine; N,N-Diisopropylethylamine; Triisopropylamine; Tris(2-aminoethyl)amine; Mechlorethamine; HN1 (nitrogen mustard); HN3 (nitrogen mustard);
Related compounds	Unsymmetrical dimethylhydrazine; Biguanide; Dithiobiuret; Agmatine;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[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.

Quick Facts Names, Identifiers ...

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

NH₃ + 3 C₂H₅OH → N(C₂H₅)₃ + 3 H₂O

The pK_a 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):

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]

[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]
"MSDS - 471283". www.sigmaaldrich.com. Retrieved 2020-06-17.
[5]
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]
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

[1] [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] [2]
X. Bories-Azeau, S. P. Armes, and H. J. W. van den Haak, Macromolecules 2004, 37, 2348 PDF

[Merck-3] [3]
The Merck Index (11th ed.). 9582.

[solubility-4] [4]
"MSDS - 471283". www.sigmaaldrich.com. Retrieved 2020-06-17.

[David_Evans_Research_Group-5] [5]
David Evans Research Group Archived 2012-01-21 at the Wayback Machine

[6] [6]
"Triethylamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[PGCH-7] [7]
NIOSH Pocket Guide to Chemical Hazards. "#0633". National Institute for Occupational Safety and Health (NIOSH).

[8] [8]
"Ethanolamine Compounds (MEA, DEA, TEA And Others)". Safe Cosmetics. Retrieved 2020-06-17.

[9] [9]
"tetraethylammonium | Ligand page | IUPHAR/BPS Guide to PHARMACOLOGY". www.guidetopharmacology.org. Retrieved 2020-06-17.

[Ullmann-10] [10]
Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). Amines, Aliphatic. doi:10.1002/14356007.a02_001. ISBN 3-527-30673-0.

[11] [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] [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] [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] [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] [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.

[Clark2018-16] [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] [17]
Brügge, Norbert (24 February 2020). "The Soviet "Scud" missile family". b14643.de. Retrieved 29 July 2022.

[18] [18]
The book of general ignorance. John Lloyd & John Mitchinson. Faber & Faber 2006, The Hawthorn, BBC

[8]

[9]

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[4]

[5]

[6]

[7]

[10]

[11]

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[13]

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[15]

[16]

[17]

[18]

Triethylamine

Niche uses

Natural occurrence

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Triethylamine

Niche uses

Natural occurrence

Wikiwand in your browser!

Synthesis and properties

Applications

References

External links