Triethanolamine
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| Names | |
|---|---|
| Preferred IUPAC name
2,2',2''-Nitrilotri(ethan-1-ol)[1] | |
Other names
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| Identifiers | |
102-71-6  | |
| 3D model (Jmol) | Interactive image |
| 3DMet | B01049 |
| 1699263 | |
| ChEBI | CHEBI:28621 |
| ChEMBL | ChEMBL446061 |
| ChemSpider | 13835630 |
| ECHA InfoCard | 100.002.773 |
| EC Number | 203-049-8 |
| KEGG | D00215 |
| MeSH | Biafine |
| PubChem | 7618 |
| RTECS number | KL9275000 |
| UNII | 9O3K93S3TK |
| |
| |
| Properties | |
| C6H15NO3 | |
| Molar mass | 149.19 g·mol−1 |
| Appearance | Colourless liquid |
| Odor | Ammoniacal |
| Density | 1.124 g mL−1 |
| Melting point | 21.60 °C; 70.88 °F; 294.75 K |
| Boiling point | 335.40 °C; 635.72 °F; 608.55 K |
| 149 g L−1 (at 20 °C) | |
| log P | −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 |
−665.7 – −662.7 kJ mol−1 |
| Std enthalpy of combustion (ΔcH |
−3.8421 – −3.8391 MJ mol−1 |
| Pharmacology | |
| D03AX12 (WHO) | |
| Hazards | |
| Safety data sheet | hazard.com |
| GHS pictograms |  |
| GHS signal word | WARNING |
| H319 | |
| P305+351+338 | |
| EU classification (DSD) |
 Xi |
| R-phrases | R36/37/38 |
| S-phrases | S26 |
| NFPA 704 | |
| 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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| Related compounds | |
| Related alkanols |
|
| Related compounds |
Diethylhydroxylamine |
| 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 | |
Triethanolamine, often abbreviated as TEA, is a viscous organic compound that is both a tertiary amine and a triol. A triol is a molecule with three alcohol groups. Triethanolamine is a strong base.[3] Triethanolamine can also be abbreviated as TEOA, which can help to distinguish it from triethylamine. Approximately 150,000 tonnes were produced in 1999.[4] It is a colourless compound although samples may appear yellow because of impurities.
Production
Triethanolamine is produced from the reaction of ethylene oxide with aqueous ammonia, also produced are ethanolamine and diethanolamine. The ratio of the products can be controlled by changing the stoichiometry of the reactants.[5]
Applications
Triethanolamine is used primarily as an emulsifier and surfactant. It is a common ingredient in formulations used for both industrial and consumer products. The triethanolamine neutralizes fatty acids, adjusts and buffers the pH, and solubilizes oils and other ingredients that are not completely soluble in water. Some common products in which triethanolamine is found are liquid laundry detergents, dishwashing liquids, general cleaners, hand sanitizers, polishes, metalworking fluids, paints, shaving cream and printing inks.[6]
Cement production
Triethanolamine is also used as organic additive (0.1 wt%) in the grinding of cement clinker. It facilitates the grinding process by preventing agglomeration and coating of the powder at the surface of balls and mill wall.[7]
Cosmetics and medicine
Various ear 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 impacted earwax. It also serves as a pH balancer in many different cosmetic products, ranging from cleansing creams and milks, skin lotions, eye gels, moisturizers, shampoos, shaving foams, and so on. TEA is a fairly strong base: a 1% solution has a pH of approximately 10, whereas the pH of skin is below pH 7, approximately 5.5−6.0. Cleansing milk–cream emulsions based on TEA are particularly good at removing makeup. (HOCH2)3N was used in the synthesis of amustaline.
In the laboratory and in amateur photography
Another common use of TEA is as a complexing agent for aluminium ions in aqueous solutions. This reaction is often used to mask such ions before complexometric titrations with another chelating agent such as EDTA. TEA has also been used in photographic (silver halide) processing. It has been promoted as a useful alkali by amateur photographers.
In holography
TEA is used to provide a sensitivity boost to silver-halide-based holograms, and also as a swelling agent to color shift holograms. You can get the sensitivity boost without the color shift by rinsing out the TEA before squeegee and drying.[8]
In electroless plating
TEA is now commonly and very effectively used as a complexing agent in electroless plating.
In ultrasonic testing
2-3% in water TEA is used as an corrosion inhibitor (anti-rust) agent in immersion ultrasonic testing.
Safety and regulation
Allergic reactions
A 1996 study found that triethanolamine (TEA) occasionally causes contact allergy.[9] A 2001 study found TEA in a sunscreen caused an allergic contact dermatitis.[10] A 2007 study found TEA in ear drops caused a contact allergy.[11] Systemic and respiratory tract (RT) toxicity was analyzed for 28 days in a nose specific inhalation 2008 study in Wistar rats; TEA seems to be less potent in regard to systemic toxicity and RT irritancy than diethanolamine (DEA). Exposure to TEA resulted in focal inflammation, starting in single male animals from 20 mg/m3 concentrations.[12]
A 2009 study stated that patch 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 TEA seems to be very low.[13]
Tumors
Reports indicated that TEA causes an increased incidence of tumor growth in the liver in female B6C3F1 mice, but not in male mice or in Fischer 344 rats.[14] A 2004 study concluded "TEA 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."[14]
Environmental toxicity
A 2009 study found that TEA has potential acute, sub-chronic and chronic toxicity properties in respect to aquatic species.[15]
Regulation
TEA is listed under Schedule 3, part B of the Chemical Weapons Convention as it can be used in the manufacture of nitrogen mustards, particularly HN3.
See also
References
- ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 79, 128. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
- ↑ Simond, M. R. (2012). "Dissociation Constants of Protonated Amines in Water at Temperatures from 293.15 K to 343.15 K". Journal of Solution Chemistry. 41: 130. doi:10.1007/s10953-011-9790-3.
- ↑ Budavari, Susan, ed. (2001), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (13th ed.), Merck, ISBN 0911910131
- ↑ Frauenkron, Matthias; Melder, Johann-Peter; Ruider, Günther; Rossbacher, Roland; Höke, Hartmut (2005), "Ethanolamines and Propanolamines", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a10_001
- ↑ Weissermel, Klaus; Arpe, Hans-Jürgen; Lindley, Charlet R.; Hawkins, Stephen (2003). "Chapter 7. Oxidation Products of Ethylene". Industrial Organic Chemistry. Wiley-VCH. pp. 159–161. ISBN 3-527-30578-5.
- ↑ Ashford, Robert D. (2011). Ashford’s Dictionary of Industrial Chemicals (3rd ed.). Saltash, Cornwall: Wavelength Publications. p. 9252. ISBN 978-0-9522674-3-0.
- ↑ Sohoni, S.; Sridhar, R.; Mandal, G. (1991). "Effect of grinding aids on the fine grinding of limestone, quartz and portland cement clinker". Powder Technology. 67 (3): 277–286. doi:10.1016/0032-5910(91)80109-V.
- ↑ "Holoforum.org". Holoforum.org. Retrieved 2016-07-16.
- ↑ Hamilton, T. K.; Zug, K. A. (1996). "Triethanolamine allergy inadvertently discovered from a fluorescent marking pen". Am. J. Contact Dermat. 7 (3): 164–5. doi:10.1016/S1046-199X(96)90006-8. PMID 8957332.
- ↑ Chu, C. Y.; Sun, C. C. (2001). "Allergic contact dermatitis from triethanolamine in a sunscreen". Contact Dermatitis. 44 (1): 41–2. doi:10.1034/j.1600-0536.2001.440107-8.x. PMID 11156016.
- ↑ Schmutz, J. L.; Barbaud, A.; Tréchot, P. (2007). "Contact allergy to triethanolamine in ear drops and shampoo". Ann. Dermatol. Venereol. 134 (1): 105. PMID 17384563.
- ↑ Gamer, A. O.; Rossbacher, R.; Kaufmann, W.; van Ravenzwaay, B. (2008). "The inhalation toxicity of di- and triethanolamine upon repeated exposure". Food Chem. Toxicol. 46 (6): 2173–2183. doi:10.1016/j.fct.2008.02.020. PMID 18420328.
- ↑ Lessmann, H.; Uter, W.; Schnuch, A.; Geier, J. (2009). "Skin sensitizing properties of the ethanolamines mono-, di-, and triethanolamine. Data analysis of a multicentre surveillance network (IVDK*) and review of the literature". Contact Dermatitis. 60 (5): 243–255. doi:10.1111/j.1600-0536.2009.01506.x. PMID 19397616.
- 1 2 Stott, W. T.; Radtke, B. J.; Linscombe, V. A.; Mar, M. H.; Zeisel, S. H. (2004). "Evaluation of the potential of triethanolamine to alter hepatic choline levels in female B6C3F1 mice". Toxicol. Sci. 79 (2): 242–7. doi:10.1093/toxsci/kfh115. PMC 1592523
. PMID 15056812. - ↑ Libralato, G.; Volpi Ghirardini, A.; Avezzù, F. (2009). "Seawater ecotoxicity of monoethanolamine, diethanolamine and triethanolamine". J. Hazard. Mater. 176 (1-3): 535–9. doi:10.1016/j.jhazmat.2009.11.062. PMID 20022426.