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Triethylamine

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.[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 in organic synthesis, usually as a base.

Triethylamine
Names
Preferred IUPAC name
N,N-Diethylethanamine
Other names
(Triethyl)amine
Triethylamine (no longer IUPAC name[1])
Identifiers
  • 121-44-8 Y
3D model (JSmol)
  • Interactive image
Abbreviations TEA[2]
605283
ChEBI
  • CHEBI:35026 Y
ChEMBL
  • ChEMBL284057 Y
ChemSpider
  • 8158 Y
ECHA InfoCard 100.004.064
EC Number
  • 204-469-4
KEGG
  • C14691 Y
MeSH triethylamine
  • 8471
RTECS number
  • YE0175000
UNII
  • VOU728O6AY Y
UN number 1296
  • DTXSID3024366
  • InChI=1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3 Y
    Key: ZMANZCXQSJIPKH-UHFFFAOYSA-N Y
  • CCN(CC)CC
Properties[4]
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
66 μmol Pa−1 kg−1
Acidity (pKa) 10.75 (for the conjugate acid) (H2O), 9.00 (DMSO)[3]
-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:
Danger
H225, H302, H312, H314, H332
P210, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
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)[5]
REL (Recommended)
None established[5]
IDLH (Immediate danger)
200 ppm[5]
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).
Y verify (what is YN ?)

Synthesis and properties

Triethylamine is prepared by the alkylation of ammonia with ethanol:[9]

NH3 + 3 C2H5OH → N(C2H5)3 + 3 H2O

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 acids, such as I2 and phenols. Owing to its steric bulk, it forms complexes with transition metals reluctantly.[citation needed]

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.[12] Such reactions lead to the production of hydrogen chloride which combines with triethylamine to form the salt triethylamine hydrochloride, commonly called triethylammonium chloride. Hydrogen chloride may then evaporate from the reaction mixture, which drives the reaction. (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 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.[13] The Soviet "Scud" Missile used TG-02 ("Tonka-250"), a mixture of 50% xylidine and 50% triethlyamine as a starting fluid to ignite its rocket engine.[14]

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 to bring hawthorn into a house. Gangrene and semen are also said to possess a similar odour.[15]

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. ^ a b David Evans Research Group 2012-01-21 at the Wayback Machine
  4. ^ The Merck Index (11th ed.). 9582.
  5. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0633". National Institute for Occupational Safety and Health (NIOSH).
  6. ^ "Triethylamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  7. ^ "Ethanolamine Compounds (MEA, DEA, TEA And Others)". Safe Cosmetics. Retrieved 2020-06-17.
  8. ^ "tetraethylammonium | Ligand page | IUPHAR/BPS Guide to PHARMACOLOGY". www.guidetopharmacology.org. Retrieved 2020-06-17.
  9. ^ Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). Amines, Aliphatic. doi:10.1002/14356007.a02_001. ISBN 3527306730.
  10. ^ "MSDS - 471283". www.sigmaaldrich.com. Retrieved 2020-06-17.
  11. ^ F., Armarego, W. L. (2012-10-17). Purification of Laboratory Chemicals. Chai, Christina Li Lin (Seventh ed.). Amsterdam. ISBN 9780123821621. OCLC 820853648.
  12. ^ Sorgi, K. L. (2001). "Triethylamine". Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/047084289X.rt217. ISBN 978-0471936237.
  13. ^ Clark, John (1972). Ignition!: An Informal History of Liquid Rocket Propellants (PDF). Rutgers University, the State University of New Jersey. p. 13. ISBN 0-8135-0725-1.
  14. ^ Brügge, Norbert (24 February 2020). "The Soviet "Scud" missile family". b14643.de. Retrieved 29 July 2022.
  15. ^ The book of general ignorance. John Lloyd & John Mitchinson. Faber & Faber 2006, The Hawthorn, BBC

External links

  • US EPA - Air Toxics Website
  • CDC - NIOSH Pocket Guide to Chemical Hazards

triethylamine, confused, with, triethanolamine, chemical, compound, with, formula, ch2ch3, commonly, abbreviated, et3n, also, abbreviated, this, abbreviation, must, used, carefully, avoid, confusion, with, triethanolamine, tetraethylammonium, which, also, comm. Not to be confused with Triethanolamine 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 7 8 It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia Like diisopropylethylamine Hunig s base triethylamine is commonly employed in organic synthesis usually as a base Triethylamine NamesPreferred IUPAC name N N DiethylethanamineOther names Triethyl amineTriethylamine no longer IUPAC name 1 IdentifiersCAS Number 121 44 8 Y3D model JSmol Interactive imageAbbreviations TEA 2 Beilstein Reference 605283ChEBI CHEBI 35026 YChEMBL ChEMBL284057 YChemSpider 8158 YECHA InfoCard 100 004 064EC Number 204 469 4KEGG C14691 YMeSH triethylaminePubChem CID 8471RTECS number YE0175000UNII VOU728O6AY YUN number 1296CompTox Dashboard EPA DTXSID3024366InChI InChI 1S C6H15N c1 4 7 5 2 6 3 h4 6H2 1 3H3 YKey ZMANZCXQSJIPKH UHFFFAOYSA N YSMILES CCN CC CCProperties 4 Chemical formula C 6H 15NMolar mass 101 193 g mol 1Appearance Colourless liquidOdor Fishy ammoniacalDensity 0 7255 g mL 1Melting point 114 70 C 174 46 F 158 45 KBoiling point 88 6 to 89 8 C 191 4 to 193 5 F 361 7 to 362 9 Klog P 1 647Vapor pressure 6 899 8 506 kPaHenry s lawconstant kH 66 mmol Pa 1 kg 1Acidity pKa 10 75 for the conjugate acid H2O 9 00 DMSO 3 Magnetic susceptibility x 81 4 10 6 cm3 molRefractive index nD 1 401ThermochemistryHeat capacity C 216 43 J K 1 mol 1Std enthalpy offormation DfH 298 169 kJ mol 1Std enthalpy ofcombustion DcH 298 4 37763 to 4 37655 MJ mol 1HazardsGHS labelling PictogramsSignal word DangerHazard statements H225 H302 H312 H314 H332Precautionary statements P210 P280 P305 P351 P338 P310NFPA 704 fire diamond 330Flash point 15 C 5 F 258 K Autoignitiontemperature 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 6 NIOSH US health exposure limits PEL Permissible TWA 25 ppm 100 mg m3 5 REL Recommended None established 5 IDLH Immediate danger 200 ppm 5 Related compoundsRelated amines DimethylamineTrimethylamineN NitrosodimethylamineDiethylamineDiisopropylamineDimethylaminopropylamineDiethylenetriamineN N DiisopropylethylamineTriisopropylamineTris 2 aminoethyl amineMechlorethamineHN1 nitrogen mustard HN3 nitrogen mustard Related compounds Unsymmetrical dimethylhydrazineBiguanideDithiobiuretAgmatineExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Synthesis and properties 2 Applications 2 1 Niche uses 2 2 Natural occurrence 3 References 4 External linksSynthesis and properties EditTriethylamine is prepared by the alkylation of ammonia with ethanol 9 NH3 3 C2H5OH N C2H5 3 3 H2OThe 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 acids such as I2 and phenols Owing to its steric bulk it forms complexes with transition metals reluctantly citation needed Applications EditTriethylamine 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 Hydrogen chloride may then evaporate from the reaction mixture which drives the reaction 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 Edit 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 13 The Soviet Scud Missile used TG 02 Tonka 250 a mixture of 50 xylidine and 50 triethlyamine as a starting fluid to ignite its rocket engine 14 Natural occurrence Edit 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 to bring hawthorn into a house Gangrene and semen are also said to possess a similar odour 15 References Edit 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 X Bories Azeau S P Armes and H J W van den Haak Macromolecules 2004 37 2348 PDF a b David Evans Research Group Archived 2012 01 21 at the Wayback Machine The Merck Index 11th ed 9582 a b c NIOSH Pocket Guide to Chemical Hazards 0633 National Institute for Occupational Safety and Health NIOSH Triethylamine Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH Ethanolamine Compounds MEA DEA TEA And Others Safe Cosmetics Retrieved 2020 06 17 tetraethylammonium Ligand page IUPHAR BPS Guide to PHARMACOLOGY www guidetopharmacology org Retrieved 2020 06 17 Eller Karsten Henkes Erhard Rossbacher Roland Hoke Hartmut 2000 Amines Aliphatic doi 10 1002 14356007 a02 001 ISBN 3527306730 MSDS 471283 www sigmaaldrich com Retrieved 2020 06 17 F Armarego W L 2012 10 17 Purification of Laboratory Chemicals Chai Christina Li Lin Seventh ed Amsterdam ISBN 9780123821621 OCLC 820853648 Sorgi K L 2001 Triethylamine Encyclopedia of Reagents for Organic Synthesis New York John Wiley amp Sons doi 10 1002 047084289X rt217 ISBN 978 0471936237 Clark John 1972 Ignition An Informal History of Liquid Rocket Propellants PDF Rutgers University the State University of New Jersey p 13 ISBN 0 8135 0725 1 Brugge Norbert 24 February 2020 The Soviet Scud missile family b14643 de Retrieved 29 July 2022 The book of general ignorance John Lloyd amp John Mitchinson Faber amp Faber 2006 The Hawthorn BBCExternal links EditUS EPA Air Toxics Website CDC NIOSH Pocket Guide to Chemical Hazards Retrieved from https en wikipedia org w index php title Triethylamine amp oldid 1113892851, wikipedia, wiki, book, books, library,

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