Triethanolamine, or TEA is a viscous organic compound that is both a tertiary amine and a triol. A triol is a molecule with three

alcohol Alcohol most commonly refers to: * Alcohol (chemistry), an organic compound in which a hydroxyl group is bound to a carbon atom * Alcohol (drug), an intoxicant found in alcoholic drinks Alcohol may also refer to: Chemicals * Ethanol, one of sev ...

groups. Approximately 150,000 tonnes 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 Stoichiometry refers to the relationship between the quantities of reactants and products before, during, and following chemical reactions. Stoichiometry is founded on the law of conservation of mass where the total mass of the reactants equal ...

of the reactants. : Reaction of ethylene oxide with ammonia

Applications

Triethanolamine is used primarily in making

surfactant Surfactants are chemical compounds that decrease the surface tension between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming ...

s, such as for

emulsifier An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Altho ...

. 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. Triethanolammonium salts in some cases are more soluble than salts of alkali 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 are

sunscreen lotion Sunscreen, also known as sunblock or sun cream, is a photoprotective topical product for the skin that mainly absorbs, or to a much lesser extent reflects, some of the sun's ultraviolet (UV) radiation and thus helps protect against sunburn and ...

s, liquid laundry detergents, dishwashing liquids, general cleaners,

hand sanitizer Hand sanitizer (also known as hand antiseptic, hand disinfectant, hand rub, or handrub) is a liquid, gel or foam generally used to kill many viruses/bacteria/microorganisms on the hands. In most settings, hand washing with soap and water is ge ...

s, polishes, metalworking fluids,

paint Paint is any pigmented liquid, liquefiable, or solid mastic composition that, after application to a substrate in a thin layer, converts to a solid film. It is most commonly used to protect, color, or provide texture. Paint can be made in many ...

s, 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 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 lotion Lotion is a low-viscosity topical preparation intended for application to the skin. By contrast, creams and gels have higher viscosity, typically due to lower water content. Lotions are applied to external skin with bare hands, a brush, a clean ...

s, eye gels, moisturizers, shampoos,

shaving foam Shaving cream or shave cream is a category of cream cosmetics used for shaving preparation. The purpose of shaving cream is to soften the hair by providing lubrication. Different types of shaving creams include Aerosol spray, aerosol shaving ...

s, TEA 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 TEA are particularly good at removing makeup.

Derivatives

# Amustaline #

Trolnitrate Trolnitrate is an organic nitrate with vasodilator activity that is used to prevent or ameliorate attacks of angina pectoris. Trolnitrate dilates the coronary vessels because of its basic action as a smooth muscle depressant, just as do nitrogly ...

# Trimustine

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 A silver halide (or silver salt) is one of the chemical compounds that can form between the element silver (Ag) and one of the halogens. In particular, bromine (Br), chlorine (Cl), iodine (I) and fluorine (F) may each combine with silver to prod ...

) 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. It is possible to get the sensitivity boost without 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.

In ultrasonic testing

2-3% in water TEA is used as an corrosion inhibitor (anti-rust) agent in immersion ultrasonic testing.

In aluminium soldering

Triethanolamine, diethanolamine and

aminoethylethanolamine Aminoethylethanolamine or AEEA is an organic base used in the industrial manufacture of fuel and oil additives, chelating agent Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or ...

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.

Safety and regulation

Allergic reactions

A 1996 study found that triethanolamine (TEOA) occasionally causes contact allergy. A 2001 study found TEOA in a

sunscreen Sunscreen, also known as sunblock or sun cream, is a photoprotective topical product for the skin that mainly absorbs, or to a much lesser extent reflects, some of the sun's ultraviolet (UV) radiation and thus helps protect against sunburn and ...

caused an allergic contact dermatitis. A 2007 study found TEOA in

ear drops Ear drops are a form of topical medication for the ears used to treat infection, inflammation, impacted ear wax and local anesthesia. They are commonly used for short-term treatment and can be purchased with or without a prescription. Before ...

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; TEOA seems to be less potent in regard to systemic toxicity and RT irritancy than diethanolamine (DEA). Exposure to TEOA resulted in focal inflammation, starting in single male animals from 20 mg/m³ concentrations. 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 TEOA seems to be very low.

Tumors

Reports indicated that TEOA 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 "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."

Environmental toxicity

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

Regulation

TEOA is listed under Schedule 3, part B of the

Chemical Weapons Convention The Chemical Weapons Convention (CWC), officially the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction, is an arms control treaty administered by the Organisation for ...

as it can be used in the manufacture of HN3 nitrogen mustard.

References

{{Authority control Triols Tertiary amines Cosmetics chemicals Tripodal ligands Ethanolamines Concrete admixtures