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| Names | |
|---|---|
| Preferred IUPAC name 2,2′,2′′-Nitrilotri(ethan-1-ol)[1] | |
Other names
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| Identifiers | |
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3D model (JSmol) | |
| 1699263 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.002.773 |
| EC Number |
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| KEGG |
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| MeSH | Biafine |
| RTECS number |
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| UNII | |
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| Properties | |
| N(CH2CH2OH)3 | |
| Molar mass | 149.190 g·mol−1 |
| Appearance | Colourless, viscous liquid |
| Odor | Ammoniacal |
| Density | 1.124 g/mL |
| Melting point | 21.60 °C; 70.88 °F; 294.75 K |
| Boiling point | 335.40 °C; 635.72 °F; 608.55 K |
| miscible | |
| logP | −0.988 |
| Vapor pressure | 1 Pa (at 20 °C) |
| Acidity (pKa) | 7.74[2] |
| UV-vis (λmax) | 280 nm |
Refractive index (nD) | 1.485 |
| Thermochemistry | |
| 389 J K−1 mol−1 | |
Std enthalpy of formation(ΔfH⦵298) | −665.7 – −662.7 kJ mol−1 |
Std enthalpy of combustion(ΔcH⦵298) | −3.8421 – −3.8391 MJ mol−1 |
| Pharmacology | |
| D03AX12 (WHO) | |
| Hazards | |
| GHS labelling: | |
 | |
| Warning | |
| H319 | |
| P305+P351+P338 | |
| NFPA 704 (fire diamond) | |
| Flash point | 179 °C (354 °F; 452 K) |
| 325 °C (617 °F; 598 K) | |
| Explosive limits | 1.3–8.5% |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
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| Safety data sheet (SDS) | hazard.com |
| Related compounds | |
Related alkanols | |
Related compounds | Diethylhydroxylamine |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Triethanolamine, orTEOA, is anorganic compound with thechemical formulaN(CH2CH2OH)3. It is a colourless,viscous liquid. It is both a tertiaryamine and atriol. A triol is amolecule with threealcoholgroups. Approximately 150,000tonnes were produced in 1999.[3] It is a colourless compound although samples may appear yellow because of impurities.
Triethanolamine is produced from the reaction ofethylene oxide with aqueousammonia, also produced areethanolamine anddiethanolamine. The ratio of the products can be controlled by changing thestoichiometry of the reactants.[4]
Triethanolamine is used primarily in makingsurfactants, such as foremulsifier. It is a common ingredient in formulations used for both industrial and consumer products. The triethanolamine neutralizesfatty acids, adjusts andbuffers thepH, and solubilizesoils and other ingredients that are not completelysoluble in water. Triethanolammonium salts in some cases are more soluble than salts ofalkali metals 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 aresunscreen lotions, liquidlaundry detergents,dishwashing liquids, general cleaners,hand sanitizers,polishes,metalworking fluids,paints,shaving cream andprinting inks.[5]
Triethanolamine is also used as organic additive (0.1 wt%) in the grinding ofcement clinker. It facilitates the grinding process by preventing agglomeration and coating of the powder at the surface of balls and mill wall.[6]
Variousear diseases and infections 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 impactedearwax. It also serves as apH balancer in many different cosmetic products, ranging from cleansing creams and milks,skin lotions, eye gels,moisturizers,shampoos,shaving foams, TEOA is a fairly strong base: a 1% solution has a pH of approximately 10, whereas the pH of skin is less than pH 7, approximately 5.5−6.0. Cleansing milk–cream emulsions based on TEOA are particularly good at removing makeup.
Another common use of TEOA is as acomplexing agent foraluminium ions in aqueous solutions. This reaction is often used to mask such ions beforecomplexometric titrations with anotherchelating agent such asEDTA. TEOA has also been used inphotographic (silver halide) processing. It has been promoted as a useful alkali by amateur photographers.
TEOA is used to provide a sensitivity boost to silver-halide-basedholograms, 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.[7]
TEOA is now commonly and very effectively used as a complexing agent inelectroless plating.
2-3% in water TEOA is used as an corrosion inhibitor (anti-rust) agent in immersion ultrasonic testing.
Triethanolamine,diethanolamine andaminoethylethanolamine 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.[8][9][10]
A 1996 study found that triethanolamine (TEOA) occasionally causes contactallergy.[11] A 2001 study found TEOA in asunscreen caused an allergic contactdermatitis.[12] A 2007 study found TEOA inear drops caused a contact allergy.[13] 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 thandiethanolamine (DEA). Exposure to TEOA resulted in focal inflammation, starting in single male animals from 20 mg/m3 concentrations.[14]
A 2009 study stated thatpatch test 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.[15]
Reports indicated that TEOA causes an increased incidence oftumor growth in the liver in female B6C3F1 mice, but not in male mice or in Fischer 344 rats.[16] 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."[16]
A 2009 study found that TEOA has potential acute, sub-chronic and chronic toxicity properties in respect to aquatic species.[17]
TEOA is listed underSchedule 3, part B of theChemical Weapons Convention as it can be used in the manufacture ofHN3 nitrogen mustard.
| Authority control databases: National |
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