Triethanolamine, or TEA is a

viscous The viscosity of a fluid is a measure of its resistance to deformation at a given rate. For liquids, it corresponds to the informal concept of "thickness": for example, syrup has a higher viscosity than water. Viscosity quantifies the in ...

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

that is both a tertiary

amine In chemistry, amines (, ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent ...

and a triol. A triol is a

molecule A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and b ...

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 A group is a number of persons or things that are located, gathered, or classed together. Groups of people * Cultural group, a group whose members share the same cultural identity * Ethnic group, a group whose members share the same ethnic ide ...

. Approximately 150,000

tonne The tonne ( or ; symbol: t) is a unit of mass equal to 1000 kilograms. It is a non-SI unit accepted for use with SI. It is also referred to as a metric ton to distinguish it from the non-metric units of the short ton ( United State ...

s 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 Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous ...

, also produced are ethanolamine and

diethanolamine Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH2CH2OH)2. Pure diethanolamine is a white solid at room temperature, but its tendencies to absorb water and to supercool meaning that it is often encou ...

. 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 equ ...

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, emulsion#Emulsifiers , ...

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. Althoug ...

. It is a common ingredient in formulations used for both industrial and consumer products. The triethanolamine neutralizes

fatty acid In chemistry, particularly in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated or unsaturated. Most naturally occurring fatty acids have an unbranched chain of an even number of carbon atoms, f ...

s, adjusts and buffers the pH, and solubilizes oils and other ingredients that are not completely

soluble In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution. The extent of the solubi ...

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 an ...

s, liquid

laundry detergent Laundry detergent is a type of detergent (cleaning agent) used for cleaning dirty laundry (clothes). Laundry detergent is manufactured in powder (washing powder) and liquid form. While powdered and liquid detergents hold roughly equal share o ...

s, 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 g ...

s, polishes,

metalworking Metalworking is the process of shaping and reshaping metals to create useful objects, parts, assemblies, and large scale structures. As a term it covers a wide and diverse range of processes, skills, and tools for producing objects on every scale ...

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 ...

shaving cream 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 shaving cream (also kn ...

and printing inks.

Cement production

Triethanolamine is also used as organic additive (0.1 wt%) in the grinding of

cement clinker 200px, Typical clinker nodules 200px, Hot clinker Cement clinker is a solid material produced in the manufacture of Portland cement as an intermediary product. Clinker occurs as lumps or nodules, usually to in diameter. It is produced by sinte ...

. 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 Earwax, also known by the medical term cerumen, is a brown, orange, red, yellowish or gray waxy substance secreted in the ear canal of humans and other mammals. It protects the skin of the human ear canal, assists in cleaning and lubrication, ...

. 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,

moisturizer A moisturizer, or emollient, is a cosmetic preparation used for protecting, moisturizing, and lubricating the skin. These functions are normally performed by sebum produced by healthy skin. The word "emollient" is derived from the Latin verb ''m ...

shampoo Shampoo () is a hair care product, typically in the form of a viscous liquid, that is used for cleaning hair. Less commonly, shampoo is available in solid bar format. Shampoo is used by applying it to wet hair, massaging the product into the ...

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 shaving cream (also kno ...

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 nitroglyce ...

# Trimustine

In the laboratory and in amateur photography

Another common use of TEA is as a complexing agent for

aluminium Aluminium (aluminum in American and Canadian English) is a chemical element with the symbol Al and atomic number 13. Aluminium has a density lower than those of other common metals, at approximately one third that of steel. It ha ...

ions in aqueous solutions. This reaction is often used to mask such ions before complexometric titrations with another chelating agent such as

EDTA Ethylenediaminetetraacetic acid (EDTA) is an aminopolycarboxylic acid with the formula H2N(CH2CO2H)2sub>2. This white, water-soluble solid is widely used to bind to iron (Fe2+/Fe3+) and calcium ions (Ca2+), forming water-soluble complexes ev ...

. TEA has also been used in

photographic Photography is the art, application, and practice of creating durable images by recording light, either electronically by means of an image sensor, or chemically by means of a light-sensitive material such as photographic film. It is employed ...

(

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

) 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

hologram Holography is a technique that enables a wavefront to be recorded and later re-constructed. Holography is best known as a method of generating real three-dimensional images, but it also has a wide range of other applications. In principle, i ...

s, 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 Electroless plating, also known as chemical plating or autocatalytic plating, is a class of industrial chemical processes that create metal coatings on various materials by autocatalytic chemical reduction of metal cations in a liquid bath. This ...

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,

and aminoethylethanolamine 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 Allergies, also known as allergic diseases, refer a number of conditions caused by the hypersensitivity of the immune system to typically harmless substances in the environment. These diseases include hay fever, food allergies, atopic derm ...

. 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 sunbur ...

caused an allergic contact

dermatitis Dermatitis is inflammation of the skin, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened. The area of skin involved c ...

. A 2007 study found TEOA 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; TEOA seems to be less potent in regard to systemic toxicity and RT irritancy than

(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