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Revision as of 14:02, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 468763706 of page Triethanolamine for the Chem/Drugbox validation project (updated: '').		Latest revision as of 00:39, 8 December 2024 edit Innerstream (talk | contribs)Autopatrolled, Extended confirmed users4,070 editsm →Production
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			{{Distinguish|Triethylamine}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 411796364
			| verifiedrevid = 470613986
	| ImageFile = Triethanolamine.png		| ImageFile = Triethanolamine.png
			| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageSize =
			| ImageSize = 180
	| IUPACName = 2,2',2"-Nitrilotriethanol
			| ImageAlt = Skeletal formula of triethanolamine
	| OtherNames = Tris(2-hydroxyethyl)amine, 2,2',2"-Trihydroxy-triethylamine, Triethylolamine, Trolamine, TEA, TEOA
			| ImageFile1 = Triethanolamine 3D ball.png
	| Section1 = {{Chembox Identifiers
			| ImageSize1 = 160
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ImageAlt1 = Ball-and-stick model of the triethanolamine molecule
			| ImageFile2 = Sample of Triethanolamine.jpg
			| ImageSize2 = 140
			| ImageName2 = Liquid form
			| ImageAlt2 = Colorless liquid in a stoppered glass bottle
			| PIN = 2,2′,2′′-Nitrilotri(ethan-1-ol)<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | pages = P001–P004 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>
			| OtherNames = {{ubl|2,2′,2′′-Nitrilotriethanol|Tris(2-hydroxyethyl)amine|Triethylolamine|2,2′,2′′-Trihydroxytriethylamine|Trolamine|TEA|TELA|TEOA}}
			|Section1={{Chembox Identifiers
			| CASNo = 102-71-6
			| CASNo_Ref = {{cascite|correct|CAS}}
			| PubChem = 7618
	| ChemSpiderID = 13835630		| ChemSpiderID = 13835630
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| UNII = 9O3K93S3TK
			| UNII_Ref = {{fdacite|correct|FDA}}
			| EINECS = 203-049-8
			| KEGG = D00215
			| KEGG_Ref = {{keggcite|correct|kegg}}
			| MeSHName = Biafine
			| ChEBI = 28621
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 446061		| ChEMBL = 446061
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
			| RTECS = KL9275000
			| Beilstein = 1699263
			| 3DMet = B01049
			| SMILES = OCCN(CCO)CCO
	| StdInChI = 1S/C6H15NO3/c8-4-1-7(2-5-9)3-6-10/h8-10H,1-6H2		| StdInChI = 1S/C6H15NO3/c8-4-1-7(2-5-9)3-6-10/h8-10H,1-6H2
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = GSEJCLTVZPLZKY-UHFFFAOYSA-N		| StdInChIKey = GSEJCLTVZPLZKY-UHFFFAOYSA-N
	| CASNo_Ref = {{cascite|correct|CAS}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			}}
	| CASNo = 102-71-6
			|Section2={{Chembox Properties
	| EINECS = 203-049-8
			| Formula = {{chem2|N(CH2CH2OH)3}}
	| PubChem = 7618
			| C=6|H=15|N=1|O=3
	| SMILES = OCCN(CCO)CCO
			| Appearance = Colourless, viscous liquid
	| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 9O3K93S3TK		| Odor = Ammoniacal
			| Density = 1.124 g/mL
	| InChI = 1/C6H15NO3/c8-4-1-7(2-5-9)3-6-10/h8-10H,1-6H2
	| RTECS = KL9275000		| MeltingPtK = 294.75
			| BoilingPtK = 608.55
	| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 28621		| Solubility = miscible
			| LogP = −0.988
	| KEGG_Ref = {{keggcite|correct|kegg}}
			| VaporPressure = 1 Pa (at 20&nbsp;°C)
	| KEGG = D00215
			| pKa = 7.74<ref>{{cite journal|author = Simond |first= M. R.| title=Dissociation Constants of Protonated Amines in Water at Temperatures from 293.15 K to 343.15 K|journal = Journal of Solution Chemistry |year = 2012|volume = 41|page = 130|doi=10.1007/s10953-011-9790-3|s2cid= 95755026}}</ref>
			| LambdaMax = 280 nm
			| RefractIndex = 1.485
			}}
			|Section5={{Chembox Thermochemistry
			| DeltaHf = −665.7 – −662.7 kJ mol<sup>−1</sup>
			| DeltaHc = −3.8421 – −3.8391 MJ mol<sup>−1</sup>
			| HeatCapacity = 389 J K<sup>−1</sup> mol<sup>−1</sup>
			}}
			|Section6={{Chembox Pharmacology
			| ATCCode_prefix = D03
			| ATCCode_suffix = AX12
			}}
			|Section7={{Chembox Hazards
			| ExternalSDS =
			| GHSPictograms = {{gHS exclamation mark}}
			| GHSSignalWord = '''WARNING'''
			| HPhrases = {{h-phrases|319}}
			| PPhrases = {{p-phrases|305+351+338}}
			| NFPA-H = 2
			| NFPA-F = 1
			| NFPA-R = 0
			| FlashPtC = 179
			| AutoignitionPtC = 325
			| ExploLimits = 1.3–8.5%
			| LD50 = {{ubl|2.2 g/kg (oral, guinea pig)|2.2 g/kg (oral, rabbit)|5.53 g/kg (oral, rat)|5.846 g/kg (oral, mouse)|22.5 g/kg (dermal, rabbit)}}
			}}
			|Section8={{Chembox Related
			| OtherFunction_label = alkanols
			| OtherFunction = {{ubl|]|]|]|]|]|]|]}}
			| OtherCompounds = ]
			}}
	}}		}}
	| Section2 = {{Chembox Properties
			'''Triethanolamine''', or '''TEOA''', is an ] with the ] {{chem2|N(CH2CH2OH)3}}. It is a colourless, ] liquid. It is both a tertiary ] and a ]. A triol is a ] with three ] ]. Approximately 150,000 ]s were produced in 1999.<ref name=Ullmann>{{Ullmann|first1=Matthias |last1=Frauenkron |first2=Johann-Peter |last2=Melder |first3=Günther |last3=Ruider |first4=Roland |last4=Rossbacher |first5=Hartmut |last5=Höke |title=Ethanolamines and Propanolamines |doi=10.1002/14356007.a10_001}}</ref> It is a colourless compound although samples may appear yellow because of impurities.
	| Formula = C<sub>6</sub>H<sub>15</sub>NO<sub>3</sub>
	| MolarMass = 149.188 g/mol
			==Production==
	| Appearance = Pale yellow liquid, ]
			Triethanolamine is produced from the reaction of ] with aqueous ], also produced are ] and ]. The ratio of the products can be controlled by changing the ] of the reactants.<ref name = weissermel>{{cite book | title = Industrial Organic Chemistry |first1=Klaus |last1=Weissermel |first2=Hans-Jürgen |last2=Arpe |first3=Charlet R. |last3=Lindley |first4=Stephen |last4=Hawkins | publisher = ] | year = 2003 | isbn = 978-3-527-30578-0 | pages = 159–161 | chapter = Chapter 7. Oxidation Products of Ethylene}}</ref>
	| Density = 1.126 g/cm<sup>3</sup>
			:]
	| MeltingPtC = 20.5
	| BoilingPtC = 335.4
			==Applications==
	| Boiling_notes = 208 °C at 20 hPa
			Triethanolamine is used primarily in making ]s, such as for ]. It is a common ingredient in formulations used for both industrial and consumer products. The triethanolamine neutralizes ]s, adjusts and ] the ], and solubilizes ]s and other ingredients that are not completely ] in water. Triethanolammonium salts in some cases are more soluble than salts of ] that might be used otherwise, and results in less alkaline products than would from using alkali metal hydroxides to form the salt. Some common products in which triethanolamine is found are ]s, liquid ]s, ]s, general cleaners, ]s, ], ] fluids, ]s, ] and ]s.<ref>{{cite book|first=Robert D. |last=Ashford |title=Ashford's Dictionary of Industrial Chemicals |edition=3rd |publisher=Wavelength Publications |location=Saltash, Cornwall |date=2011 |page=9252 |isbn=978-0-9522674-3-0}}</ref>
	| Solubility = Miscible
	| VapourPressure = 0.01 hPa (20 °C)
			===Cement production===
	}}
			Triethanolamine is also used as organic additive (0.1&nbsp;wt%) in the grinding of ]. It facilitates the grinding process by preventing agglomeration and coating of the powder at the surface of balls and mill wall.<ref>
	| Section3 = {{Chembox Hazards
			{{Cite journal
	| ExternalMSDS =
			| last1 = Sohoni
	| MainHazards = Irritant
	| FlashPt = 179 °C		| first1 = S.
	| Autoignition = 325 °C		| first2 = R.
			| last2 = Sridhar
	| ExploLimits = 3.6 - 7.2 %
	| NFPA-H = 2		| first3 = G.
	| NFPA-F = 1		| last3 = Mandal
	| NFPA-R =		| year = 1991
			| title = Effect of grinding aids on the fine grinding of limestone, quartz and portland cement clinker
	| NFPA-O =
			| journal = Powder Technology
	| RPhrases = {{R36}} {{R37}} {{R38}}
			| volume = 67
	| SPhrases = {{S26}} {{S36}}
			| issue = 3
	}}
			| pages = 277–286
			| doi = 10.1016/0032-5910(91)80109-V
	}}		}}
			</ref>
			===Cosmetics and medicine===
			Various ] are treated with eardrops containing triethanolamine polypeptide oleate-condensate, such as Cerumenex in the United States. In pharmaceutics, triethanolamine is the active ingredient of some eardrops used to treat impacted ]. It also serves as a ] balancer in many different cosmetic products, ranging from cleansing creams and milks, ]s, eye gels, ]s, ]s, ]s, TEOA is a fairly strong base: a 1% solution has a pH of approximately 10, whereas the pH of skin is less than pH&nbsp;7, approximately 5.5−6.0. Cleansing milk–cream emulsions based on TEOA are particularly good at removing makeup.
			===Derivatives===
			#]
			#]
			#]
			===In the laboratory and in amateur photography===
			Another common use of TEOA is as a ] for ] ions in aqueous solutions. This reaction is often used to mask such ions before ]s with another ] agent such as ]. TEOA has also been used in ] (]) processing. It has been promoted as a useful alkali by amateur photographers.
			===In holography===
			TEOA is used to provide a sensitivity boost to silver-halide-based ]s, and also as a swelling agent to color shift holograms. It is possible to get the sensitivity boost without color shift by rinsing out the TEOA before squeegee and drying.<ref>{{cite web|url=http://holoforum.org/oldforum/viewtopic.php?f=17&t=5058 |title=Holoforum.org |website=Holoforum.org |access-date=2016-07-16}}</ref>
			===In electroless plating===
			TEOA is now commonly and very effectively used as a complexing agent in ].
			===In ultrasonic testing===
			2-3% in water TEOA is used as an corrosion inhibitor (anti-rust) agent in immersion ultrasonic testing.
			===In aluminium soldering===
			Triethanolamine, ] and ] are major components of common liquid organic fluxes for the soldering of aluminium alloys using tin-zinc and other tin or lead-based soft solders.<ref>{{cite web |title=Kapp Liquid Flux SDS |url=https://www.kappalloy.com/pub/media/pdf/SDS_551_GHS_R12_Liquid_Golden_FLux.pdf |website=kappalloy.com |access-date=9 April 2019}}</ref><ref>{{cite web |title=Harris Stay-Clean Aluminum Flux SDS |url=http://www.lincolnelectric.com/assets/US/EN/MSDS_lib/ZLE_SDS_NA-EN-200000007463.pdf |website=lincolnelectric.com |access-date=9 April 2019}}</ref><ref>{{cite web |title=Superior #1260 Flux SDS |url=http://www.superiorflux.com/sds/1260.pdf |website=superiorflux.com |access-date=9 April 2019}}</ref>
			==Safety and regulation==
			===Allergic reactions===
			A 1996 study found that triethanolamine (TEOA) occasionally causes contact ].<ref>{{cite journal |doi=10.1016/S1046-199X(96)90006-8 |journal=Am. J. Contact Dermat. |year=1996 |volume=7 |issue=3 |pages=164–5 |title=Triethanolamine allergy inadvertently discovered from a fluorescent marking pen |last1=Hamilton |first1=T. K. |last2=Zug |first2=K. A. |pmid=8957332}}</ref> A 2001 study found TEOA in a ] caused an allergic contact ].<ref>{{cite journal |journal=Contact Dermatitis |year=2001 |volume=44 |issue=1 |pages=41–2 |title=Allergic contact dermatitis from triethanolamine in a sunscreen |last1=Chu |first1=C. Y. |last2=Sun |first2=C. C. |pmid=11156016|doi=10.1034/j.1600-0536.2001.440107-8.x |s2cid=7174704 }}</ref> A 2007 study found TEOA in ] caused a contact allergy.<ref>{{cite journal |journal=Ann. Dermatol. Venereol. |year=2007 |volume=134 |issue=1 |page=105 |title=Contact allergy to triethanolamine in ear drops and shampoo |last1=Schmutz |first1=J. L. |last2=Barbaud |first2=A. |last3=Tréchot |first3=P. |pmid=17384563|doi=10.1016/S0151-9638(07)89009-0 }}</ref> Systemic and respiratory tract (RT) toxicity was analyzed for 28 days in a nose specific inhalation 2008 study in Wistar rats; TEOA seems to be less potent in regard to systemic toxicity and RT irritancy than ] (DEA). Exposure to TEOA resulted in focal inflammation, starting in single male animals from 20&nbsp;mg/m<sup>3</sup> concentrations.<ref>{{cite journal |journal=Food Chem. Toxicol. |year=2008 |volume=46 |issue=6 |pages=2173–2183 |title=The inhalation toxicity of di- and triethanolamine upon repeated exposure |last1=Gamer |first1=A. O. |last2=Rossbacher |first2=R. |last3=Kaufmann |first3=W. |last4=van Ravenzwaay |first4=B. |pmid=18420328 |doi=10.1016/j.fct.2008.02.020}}</ref>
			A 2009 study stated that ] reactions reveal a slight irritant potential instead of a true allergic response in several cases, and also indicated the risk of skin sensitization to TEOA seems to be very low.<ref>{{cite journal |journal=Contact Dermatitis |year=2009 |volume=60 |issue=5 |pages=243–255 |title=Skin sensitizing properties of the ethanolamines mono-, di-, and triethanolamine. Data analysis of a multicentre surveillance network (IVDK*) and review of the literature |last1=Lessmann |first1=H. |last2=Uter |first2=W. |last3=Schnuch |first3=A. |last4=Geier |first4=J. |pmid=19397616 |doi=10.1111/j.1600-0536.2009.01506.x|doi-access=free }}</ref>
			===Tumors===
			Reports indicated that TEOA causes an increased incidence of ] in the liver in female B6C3F1 mice, but not in male mice or in Fischer 344 rats.<ref name="Stott WT"/> A 2004 study concluded "TEOA may cause liver tumors in mice via a choline-depletion mode of action and that this effect is likely caused by the inhibition of choline uptake by cells."<ref name="Stott WT">{{cite journal |journal=Toxicol. Sci. |year=2004 |volume=79 |issue=2 |pages=242–7 |title=Evaluation of the potential of triethanolamine to alter hepatic choline levels in female B6C3F1 mice |last1=Stott |first1=W. T. |last2=Radtke |first2=B. J. |last3=Linscombe |first3=V. A. |last4=Mar |first4=M. H. |last5=Zeisel |first5=S. H. |pmid=15056812 |doi=10.1093/toxsci/kfh115 |pmc=1592523}}</ref>
			===Environmental toxicity===
			A 2009 study found that TEOA has potential acute, sub-chronic and chronic toxicity properties in respect to aquatic species.<ref>{{cite journal |journal=J. Hazard. Mater. |year=2009 |volume= 176|issue= 1–3|pages= 535–9|title=Seawater ecotoxicity of monoethanolamine, diethanolamine and triethanolamine |last1=Libralato |first1=G. |last2=Volpi Ghirardini |first2=A. |last3=Avezzù |first3=F. |pmid=20022426 |doi=10.1016/j.jhazmat.2009.11.062}}</ref>
			===Regulation===
			TEOA is listed under ] of the ] as it can be used in the manufacture of ].
			==See also==
			*]
			*]
			*]
			*]
			==References==
			{{Reflist}}
			{{Authority control}}
			]
			]
			]
			]
			]
			]