Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Triethylamine: Difference between pages

{{Distinguish|Triethanolamine}}

|Watchedfields = changed

|verifiedrevid = 470614173

|ImageFile = Et3N showing pyramidal-ness.svg

|ImageFile_Ref = {{chemboximage|correct|??}}

|ImageSize = 200

|ImageName = Skeletal formula of triethylamine

|ImageFileL1 = Triethylamine-3D-balls.png

|ImageFileL1_Ref = {{chemboximage|correct|??}}

|ImageNameL1 = Ball and stick model of triethylamine

|ImageFileR1 = Triethylamine-3D-vdW.png

|ImageFileR1_Ref = {{chemboximage|correct|??}}

|ImageNameR1 = Spacefill model of triethylamine

|PIN = ''N'',''N''-Diethylethanamine <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) corrected according to http://www.chem.qmul.ac.uk/iupac/bibliog/BBerrors.html -->

|OtherNames = (Triethyl)amine<br>Triethylamine (no longer IUPAC name<ref>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 671 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>)

|Section1={{Chembox Identifiers

|Abbreviations = TEA<ref>X. Bories-Azeau, S. P. Armes, and H. J. W. van den Haak, Macromolecules 2004, 37, 2348 [http://pubs.acs.org/cgi-bin/article.cgi/mamobx/2004/37/i07/pdf/ma035904u.pdf PDF]</ref>

|CASNo = 121-44-8

|CASNo_Ref = {{cascite|correct|CAS}}

|PubChem = 8471

|ChemSpiderID = 8158

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|UNII = VOU728O6AY

|UNII_Ref = {{fdacite|correct|FDA}}

|EINECS = 204-469-4

|UNNumber = 1296

|KEGG = C14691

|KEGG_Ref = {{keggcite|correct|kegg}}

|MeSHName = triethylamine

|ChEBI = 35026

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 284057

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|RTECS = YE0175000

|Beilstein = 605283

|SMILES = CCN(CC)CC

|StdInChI = 1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = ZMANZCXQSJIPKH-UHFFFAOYSA-N

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}}}

|Section2={{Chembox Properties

| Properties_ref = <ref name=Merck>{{ cite book | title = The Merck Index | edition = 11th | id = 9582 | title-link = The Merck Index }}</ref>

|C=6 | H=15 | N=1

|Appearance = Colourless liquid

|Odor = Fishy, ammoniacal

|Density = 0.7255 g mL⁻¹

|BoilingPtK = 361.7 to 362.9

|MeltingPtK = 158.45

|Solubility = 112.4 g/L at 20 °C<ref name="solubility">{{Cite web|title=MSDS - 471283|url=https://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=CA&language=en&productNumber=471283&brand=SIAL&PageToGoToURL=https://www.sigmaaldrich.com/catalog/product/sial/471283?lang=en|access-date=2020-06-17|website=www.sigmaaldrich.com}}</ref>

|SolubleOther = miscible with organic solvents

|pKa = 10.75 (for the conjugate acid) (H₂O), 9.00 (DMSO)<ref name="David Evans Research Group"/>

|LogP = 1.647

|VaporPressure = 6.899–8.506 kPa

|HenryConstant = 66 μmol Pa⁻¹ kg⁻¹

|RefractIndex = 1.401

|MagSus = -81.4·10⁻⁶ cm³/mol

|Section3={{Chembox Thermochemistry

|DeltaHf = −169 kJ mol⁻¹

|DeltaHc = −4.37763 to −4.37655 MJ mol⁻¹

|HeatCapacity = 216.43 J K⁻¹ mol⁻¹

}}

|Section4={{Chembox Hazards

|GHSPictograms = {{gHS flame}} {{gHS corrosion}} {{gHS exclamation mark}}

|GHSSignalWord = '''DANGER'''

|HPhrases = {{h-phrases|225|302|312|314|332}}

|PPhrases = {{p-phrases|210|280|305+351+338|310}}

|NFPA-H = 3

|NFPA-F = 3

|NFPA-R = 0

|FlashPtC = -15

|AutoignitionPtC = 312

|ExploLimits = 1.2–8%

|TLV-TWA = 2 ppm (8 mg/m³)

|TLV-STEL =<BR/>4 ppm (17 mg/m³)

|LD50 = {{unbulleted list|580 mg kg⁻¹ <small>(dermal, rabbit)</small>|730 mg kg⁻¹ <small>(oral, rat)</small>}}

|IDLH = 200 ppm<ref name=PGCH>{{PGCH|0633}}</ref>

|REL = None established<ref name=PGCH/>

|PEL = TWA 25 ppm (100 mg/m³)<ref name=PGCH/>

|LCLo = 1425 ppm (mouse, 2 hr)<ref>{{IDLH|121448|Triethylamine}}</ref>

}}

|Section5={{Chembox Related

|OtherFunction_label = amines

|OtherFunction = {{unbulleted list|[[Dimethylamine]]|[[Trimethylamine]]|[[n-Nitrosodimethylamine|''N''-Nitrosodimethylamine]]|[[Diethylamine]]|[[Diisopropylamine]]|[[Dimethylaminopropylamine]]|[[Diethylenetriamine]]|[[n,N-Diisopropylethylamine|''N'',''N''-Diisopropylethylamine]]|[[Triisopropylamine]]|[[Tris(2-aminoethyl)amine]]|[[Mechlorethamine]]|[[HN1 (nitrogen mustard)]]|[[HN3 (nitrogen mustard)]]}}

|OtherCompounds = {{unbulleted list|[[Unsymmetrical dimethylhydrazine]]|[[Biguanide]]|[[Dithiobiuret]]|[[Agmatine]]}}

}}

}}

'''Triethylamine''' is the [[chemical compound]] with the [[chemical formula|formula]] N(CH₂CH₃)₃, commonly abbreviated [[ethyl group|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.<ref>{{Cite web|title=Ethanolamine Compounds (MEA, DEA, TEA And Others)|url=http://www.safecosmetics.org/get-the-facts/chemicals-of-concern/ethanolamine-compounds/|access-date=2020-06-17|website=Safe Cosmetics|language=en-US}}</ref><ref>{{Cite web|title=tetraethylammonium {{!}} Ligand page {{!}} IUPHAR/BPS Guide to PHARMACOLOGY|url=https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=2343|access-date=2020-06-17|website=www.guidetopharmacology.org}}</ref> It is a colourless [[Volatility (chemistry)|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 (chemistry)|base]].

==Synthesis and properties==

Triethylamine is prepared by the [[alkylation]] of ammonia with [[ethanol]]:<ref name=Ullmann>{{cite book|doi=10.1002/14356007.a02_001|title=Amines, Aliphatic|year=2000|last1=Eller|first1=Karsten|last2=Henkes|first2=Erhard|last3=Rossbacher|first3=Roland|last4=Höke|first4=Hartmut|isbn=3-527-30673-0}}</ref>

:NH₃ + 3 C₂H₅OH → N(C₂H₅)₃ + 3 H₂O

The pK_a of protonated triethylamine is 10.75,<ref name="David Evans Research Group">[http://www2.lsdiv.harvard.edu/labs/evans/pdf/evans_pKa_table.pdf David Evans Research Group] {{Webarchive|url=https://web.archive.org/web/20120121150933/http://www2.lsdiv.harvard.edu/labs/evans/pdf/evans_pKa_table.pdf |date=2012-01-21 }}</ref> and it can be used to prepare buffer solutions at that pH. The [[hydrochloride]] [[salt (chemistry)|salt]], triethylamine hydrochloride (triethylammonium chloride), is a colorless, odorless, and [[hygroscopic]] powder, which decomposes when heated to 261&nbsp;°C.

Triethylamine is soluble in water to the extent of 112.4 g/L at 20 °C.<ref name="solubility"/> 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]].<ref>{{Cite book|title=Purification of Laboratory Chemicals|last=F.|first=Armarego, W. L.|others=Chai, Christina Li Lin|isbn=978-0-12-382162-1|edition= Seventh |location=Amsterdam|oclc=820853648|date = 2012-10-17}}</ref>

In alkane solvents triethylamine is a [[Lewis base]] that forms adducts with a variety of Lewis acids, such as [[iodine|I₂]] and [[Phenol|phenols]]. Owing to its steric bulk, it forms complexes with transition metals reluctantly.<ref>{{Cite journal |last1=DeLaive |first1=Patricia J. |last2=Sullivan |first2=B. P. |last3=Meyer |first3=T. J. |last4=Whitten |first4=D. G. |date=July 1979 |title=Applications of light-induced electron-transfer reactions. Coupling of hydrogen generation with photoreduction of ruthenium(II) complexes by triethylamine |url=https://pubs.acs.org/doi/abs/10.1021/ja00508a070 |journal=Journal of the American Chemical Society |language=en |volume=101 |issue=14 |pages=4007–4008 |doi=10.1021/ja00508a070 |issn=0002-7863}}</ref><ref>{{Cite journal |last1=DeLaive |first1=Patricia J. |last2=Foreman |first2=Thomas K. |last3=Giannotti |first3=Charles |last4=Whitten |first4=David G. |date=August 1980 |title=Photoinduced electron transfer reactions of transition-metal complexes with amines. Mechanistic studies of alternate pathways to back electron transfer |url=https://pubs.acs.org/doi/abs/10.1021/ja00537a037 |journal=Journal of the American Chemical Society |language=en |volume=102 |issue=17 |pages=5627–5631 |doi=10.1021/ja00537a037 |issn=0002-7863}}</ref><ref>{{Cite journal |last1=Seligson |first1=Allen L. |last2=Trogler |first2=William C. |date=March 1991 |title=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 |url=https://pubs.acs.org/doi/abs/10.1021/ja00007a028 |journal=Journal of the American Chemical Society |language=en |volume=113 |issue=7 |pages=2520–2527 |doi=10.1021/ja00007a028 |issn=0002-7863}}</ref>

==Applications==

Triethylamine is commonly employed in organic synthesis as a [[base (chemistry)|base]]. For example, it is commonly used as a base during the preparation of [[ester]]s and [[amide]]s from [[acyl chloride]]s.<ref>{{cite encyclopedia | author = Sorgi, K. L. | encyclopedia = Encyclopedia of Reagents for Organic Synthesis | year = 2001 | publisher = John Wiley & Sons | location = New York | doi = 10.1002/047084289X.rt217 | chapter = Triethylamine | isbn = 978-0-471-93623-7 }}</ref> 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 oxidation]]s.

Triethylamine is readily alkylated to give the corresponding [[Quaternary ammonium cation|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 [[dye]]s. It is also a [[catalyst]] and acid neutralizer for [[condensation reaction]]s and is useful as an intermediate for manufacturing medicines, [[pesticide]]s 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 [[Amphiphile|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 dispersion|PUDs]]. A polyurethane [[prepolymer]] is prepared using an [[isocyanate]] and [[polyol]] with [[dimethylol propionic acid]] (DMPA). This molecule contains two [[hydroxy group]]s 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.<ref>{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/2_2-Bis_hydroxymethyl_propionic_acid#section=Top|title=Dimethylolpropionic acid|last=Pubchem|website=pubchem.ncbi.nlm.nih.gov|access-date=2018-08-21}}</ref><ref>{{cite journal|last1=Jang|first1=JY|last2=Jhon|first2=YK|last3=Cheong|first3=IW|last4=Kim|first4=JH|date=2002-01-01|title=Colloids and Surfaces A: Physicochem|url=https://www.researchgate.net/publication/286005163|journal=Eng. Aspects|volume=196|pages=135–143}}</ref><ref>{{Cite journal |last=Howarth |first=GA |date=2003-06-01 |title=Polyurethanes, polyurethane dispersions and polyureas: Past, present and future |url=https://doi.org/10.1007/BF02699621 |journal=Surface Coatings International Part B: Coatings Transactions |language=en |volume=86 |issue=2 |pages=111–118 |doi=10.1007/BF02699621 |s2cid=93574741 |issn=1476-4865}}</ref> [[2-Methylpentamethylenediamine|Dytek A]] is commonly used as a chain extender.<ref>{{Cite journal |last1=Madbouly |first1=Samy A. |last2=Otaigbe |first2=Joshua U. |last3=Nanda |first3=Ajaya K. |last4=Wicks |first4=Douglas A. |date=2005-05-01 |title=Rheological Behavior of Aqueous Polyurethane Dispersions: Effects of Solid Content, Degree of Neutralization, Chain Extension, and Temperature |url=https://pubs.acs.org/doi/10.1021/ma050453u |journal=Macromolecules |language=en |volume=38 |issue=9 |pages=4014–4023 |doi=10.1021/ma050453u |bibcode=2005MaMol..38.4014M |issn=0024-9297}}</ref>

Triethylamine is used to give salts of various carboxylic acid-containing pesticides, e.g. [[Triclopyr]] and [[2,4-dichlorophenoxyacetic acid]].{{citation needed|date=July 2018}}

Triethylamine is the active ingredient in [[FlyNap]], a product for anesthetizing ''[[Drosophila melanogaster]]''.{{citation needed|date=July 2018}} 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 (chemistry)|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|date=July 2018}}

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.<ref name=Clark>{{cite book |last=Clark |first=John |date=1972 |title=Ignition!: An Informal History of Liquid Rocket Propellants |url=http://www.sciencemadness.org/library/books/ignition.pdf |publisher=Rutgers University, the State University of New Jersey |page=13 |isbn=0-8135-0725-1 }}</ref>

The Soviet [[Scud_missile|"Scud" Missile]] used [[Tonka_(fuel)|TG-02]] ("Tonka-250"), a mixture of 50% [[xylidine]] and 50% triethylamine as a starting fluid to ignite its rocket engine.<ref>{{cite web

|url=http://www.b14643.de/Spacerockets/Specials/Scud/

|title=The Soviet "Scud" missile family

|date=24 February 2020

|author=Brügge, Norbert

|website=b14643.de

|access-date=29 July 2022}}</ref>

===Natural occurrence===

[[Crataegus|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 [[Corpse decomposition|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.<ref>The book of general ignorance. John Lloyd & John Mitchinson. Faber & Faber 2006, [https://web.archive.org/web/20220426050027/https://h2g2.com/edited_entry/A34170932 The Hawthorn], BBC</ref>

==References==

{{reflist}}

==External links==

* [http://www.epa.gov/ttn/atw/hlthef/tri-lami.html US EPA - Air Toxics Website]

* [https://www.cdc.gov/niosh/npg/npgd0633.html CDC - NIOSH Pocket Guide to Chemical Hazards]

{{Authority control}}

[[Category:Alkylamines]]

[[Category:Tertiary amines]]