Triethanolamine

Triethanolamine
Skeletal formula of triethanolamine
Ball-and-stick model of the triethanolamine molecule
Colorless liquid in a stoppered glass bottle
Names
IUPAC name
Tris(2-hydroxyethyl)amine
Other names
  • Triethylolamine
  • 2,2',2"-Trihydroxy-triethylamine
  • Trolamine
  • TEA
  • TEOA
Identifiers
102-71-6 YesY
3DMet B01049
1699263
ChEBI CHEBI:28621 YesY
ChEMBL ChEMBL446061 YesY
ChemSpider 13835630 YesY
EC Number 203-049-8
Jmol interactive 3D Image
KEGG D00215 YesY
MeSH Biafine
PubChem 7618
RTECS number KL9275000
UNII 9O3K93S3TK YesY
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[1]
UV-vis (λmax) 280 nm
1.485
Thermochemistry
389 J K−1 mol−1
−665.7–−662.7 kJ mol−1
−3.8421–−3.8391 MJ mol−1
Pharmacology
ATC code D03AX12
Hazards
Safety data sheet hazard.com
GHS pictograms
GHS signal word WARNING
H319
P305+351+338
Xi
R-phrases R36/37/38
S-phrases S26
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
2
0
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):
  • 2.2 g kg−1 (oral, guinea pig)
  • 2.2 g kg−1 (oral, rabbit)
  • 5.53 g kg−1 (oral, rat)
  • 5.846 g kg−1 (oral, mouse)
  • 22.5 g kg−1 (dermal, rabbit)
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).
YesY verify (what is YesYN ?)
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.[2] Triethanolamine can also be abbreviated as TEOA, which can help to distinguish it from triethylamine. Approximately 150,000 metric tons were produced in 1999.[3] 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.[4]

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 solubilises 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 cleaners, polishes, metalworking fluids, paints, shaving cream and printing inks.[5]

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.[6]

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 ear drops 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 etc. TEA is a fairly strong base: a 1% solution has a pH of approximately 10, whereas the pH of skin is below pH 7, more or less 5.5-6.0. Cleansing milk/cream emulsions based on TEA are particularly good at removing makeup.

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. 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.[7]

In electroless plating

TEA is now commonly and very effectively used as a complexing agent in electroless plating.

Safety and regulation

Allergic reactions

A 1996 study found that triethanolamine (TEA) occasionally causes contact allergy.[8] A 2001 study found TEA in a sunscreen caused an allergic contact dermatitis.[9] A 2007 study found TEA in ear drops caused a contact allergy.[10] 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.[11]

A 2009 study stated 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.[12]

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.[13] 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."[13]

Environmental toxicity

A 2009 study found that TEA has potential acute, sub-chronic and chronic toxicity properties in respect to aquatic species.[14]

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.

References

  1. ↑ 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.
  2. ↑ O'Neil, MJ. The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. (13th ed.). Whitehouse Station, NJ: Merck and Co., Inc. p. 1722.
  3. ↑ Matthias Frauenkron, Johann-Peter Melder, Günther Ruider, Roland Rossbacher, Hartmut Höke "Ethanolamines and Propanolamines" in Ullmann's Encyclopedia of Industrial Chemistry, 2002 Wiley-VCH, Weinheim doi:10.1002/14356007.a10_001
  4. ↑ Klaus Weissermel, Hans-Jürgen Arpe, Charlet R. Lindley, Stephen Hawkins (2003). "Chap. 7. Oxidation Products of Ethylene". Industrial Organic Chemistry. Wiley-VCH. pp. 159–161. ISBN 3-527-30578-5.
  5. ↑ Ashford’s Dictionary of Industrial Chemicals, third edition, 2011, page 9252
  6. ↑ Sohoni, S.; R. Sridhar; G. Mandal (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.
  7. ↑ http://holoforum.org/oldforum/viewtopic.php?f=17&t=5058
  8. ↑ Hamilton TK, Zug KA (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.
  9. ↑ Chu CY, Sun CC (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.
  10. ↑ Schmutz JL, Barbaud A, Tréchot P (2007). "[Contact allergy to triethanolamine in ear drops and shampoo]". Ann Dermatol Venereol 134 (1): 105. PMID 17384563.
  11. ↑ Gamer AO, Rossbacher R, Kaufmann W, van Ravenzwaay B (2008). "The inhalation toxicity of di- and triethanolamine upon repeated exposure". Food Chem Toxicol 46 (6): 2173–83. doi:10.1016/j.fct.2008.02.020. PMID 18420328.
  12. ↑ 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): 243–55. doi:10.1111/j.1600-0536.2009.01506.x. PMID 19397616.
  13. 1 2 Stott WT, Radtke BJ, Linscombe VA, Mar MH, Zeisel SH (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.
  14. ↑ 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.

See also

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