Triethanolamine

Triethanolamine

Skeletal formula of triethanolamine
Ball-and-stick model of the triethanolamine molecule
Liquid form
Names
IUPAC name Tris(2-hydroxyethyl)amine
Other names Triethylolamine 2,2',2"-Trihydroxy-triethylamine Trolamine TEA TEOA
Identifiers
CAS Number	102-71-6 Y
3DMet	B01049
Beilstein Reference	1699263
ChEBI	CHEBI:28621 Y
ChEMBL	ChEMBL446061 Y
ChemSpider	13835630 Y
EC Number	203-049-8
Jmol 3D model	Interactive image
KEGG	D00215 Y
MeSH	Biafine
PubChem	7618
RTECS number	KL9275000
UNII	9O3K93S3TK Y
InChI InChI=1S/C6H15NO3/c8-4-1-7(2-5-9)3-6-10/h8-10H,1-6H2 Y Key: GSEJCLTVZPLZKY-UHFFFAOYSA-N Y
SMILES OCCN(CCO)CCO
Properties
Chemical formula	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
Solubility in water	149 g L−1 (at 20 °C)
log P	−0.988
Vapor pressure	1 Pa (at 20 °C)
Acidity (pKa)	7.74
UV-vis (λmax)	280 nm
Refractive index (nD)	1.485
Thermochemistry
Specific heat capacity (C)	389 J K−1 mol−1
Std enthalpy of formation (ΔfHo298)	−665.7–−662.7 kJ mol−1
Std enthalpy of combustion (ΔcHo298)	−3.8421–−3.8391 MJ mol−1
Pharmacology
ATC code	D03AX12
Vapor pressure	{{{value}}}
Related compounds
Related alkanols	N-Methylethanolamine Dimethylethanolamine Diethylethanolamine Diethanolamine N,N-Diisopropylaminoethanol Methyl diethanolamine Bis-tris methane
Related compounds	Diethylhydroxylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
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. Triethanolamine can also be abbreviated as TEOA, which can help to distinguish it from triethylamine. Approximately 150,000 metric tons were produced in 1999. 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.

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.

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.

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.

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. A 2001 study found TEA in a sunscreen caused an allergic contact dermatitis. A 2007 study found TEA in ear drops caused a contact allergy. 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.

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.

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. 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."

Environmental toxicity

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

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

• Complexometric titration
• Ethanolamine
• Ethanol
• Triethanolamine salicylate