Triethanolamine, or TEOA, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the

chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...

. It is a colourless,

viscous Viscosity is a measure of a fluid's rate-dependent resistance to a change in shape or to movement of its neighboring portions relative to one another. For liquids, it corresponds to the informal concept of ''thickness''; for example, syrup h ...

liquid. It is both a tertiary

amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

and a

triol In chemistry, a triol is an organic compound containing three hydroxyl groups ( functional groups),molecule A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ...

with three

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

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 iden ...

. Approximately 150,000

tonne The tonne ( or ; symbol: t) is a unit of mass equal to 1,000 kilograms. It is a non-SI unit accepted for use with SI. It is also referred to as a metric ton in the United States to distinguish it from the non-metric units of the s ...

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 Ethylene oxide is an organic compound with the chemical formula, formula . It is a cyclic ether and the simplest epoxide: a three-membered ring (chemistry), ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless ...

with aqueous

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

, also produced are

ethanolamine Ethanolamine (2-aminoethanol, monoethanolamine, ETA, or MEA) is a naturally occurring organic chemical compound with the formula or . The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorl ...

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 often results in it being foun ...

. The ratio of the products can be controlled by changing the

stoichiometry Stoichiometry () is the relationships between the masses of reactants and Product (chemistry), products before, during, and following chemical reactions. Stoichiometry is based on the law of conservation of mass; the total mass of reactants must ...

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 or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...

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. Althou ...

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

fatty acid In chemistry, in particular in biochemistry, a fatty acid is a carboxylic acid with an aliphatic chain, which is either saturated and unsaturated compounds#Organic chemistry, saturated or unsaturated. Most naturally occurring fatty acids have an ...

s, adjusts and buffers the pH, and solubilizes

oil An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) and lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturate ...

s 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 The alkali metals consist of the chemical elements lithium (Li), sodium (Na), potassium (K),The symbols Na and K for sodium and potassium are derived from their Latin names, ''natrium'' and ''kalium''; these are still the origins of the names ...

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 lotions, 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 of ...

dishwashing liquid Dishwashing liquid (washing-up liquid or fairy liquid in British English), also known as dishwashing soap, dish detergent, or dish soap, is a detergent used in dishwashing. Dishwashing detergent for dishwashers comes in various forms such a ...

s, general cleaners,

hand sanitizer Hand sanitizer (also known as hand antiseptic, hand disinfectant, hand rub, or handrub) is a liquid, gel, or foam used to kill viruses, bacteria, and other microorganisms on the hands. It can also come in the form of a cream, spray, or wipe. W ...

polishes Polishing is the process of creating a smooth and shiny surface by rubbing it or by applying a chemical treatment, leaving a clean surface with a significant specular reflection (still limited by the index of refraction of the material according ...

metalworking Metalworking is the process of shaping and reshaping metals in order 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 e ...

fluids,

paint Paint is a material or mixture that, when applied to a solid material and allowed to dry, adds a film-like layer. As art, this is used to create an image or images known as a painting. Paint can be made in many colors and types. Most paints are ...

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 ink Ink is a gel, sol, or solution that contains at least one colorant, such as a dye or pigment, and is used to color a surface to produce an image, text, or design. Ink is used for drawing or writing with a pen, brush, reed pen, or quill. ...

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 sinter ...

. 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 waxy substance secreted in the ear canal of humans and other mammals. Earwax can be many colors, including brown, orange, red, yellowish, and gray. Earwax protects the skin of the human ear ...

. It also serves as a pH balancer in many different cosmetic products, ranging from cleansing creams and milks, skin lotions, eye gels,

moisturizer A moisturizer, or emollient, is a Cosmetics, cosmetic preparation used for protecting, moisturizing, and lubricating the Human skin, skin. These functions are normally performed by Sebaceous gland, sebum produced by healthy skin. The word "emollie ...

shampoo Shampoo () is a hair care product, typically in the form of a viscous liquid, that is formulated to be used for cleaning (scalp) hair. Less commonly, it is available in solid bar format. (" Dry shampoo" is a separate product.) Shampoo is use ...

s, shaving foams, TEOA 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 TEOA are particularly good at removing makeup.

Derivatives

# Amustaline #

Trolnitrate Trolnitrate (triethanolamine trinitrate, commonly used in the form of biphosphate salt also known as metamine) is an organic nitrate with vasodilator activity that is used to prevent or ameliorate attacks of angina pectoris. Trolnitrate dilates th ...

# Trimustine

In the laboratory and in amateur photography

Another common use of TEOA is as a

complexing agent A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or ...

for

aluminium Aluminium (or aluminum in North American English) is a chemical element; it has chemical symbol, symbol Al and atomic number 13. It has a density lower than that of other common metals, about one-third that of steel. Aluminium has ...

ions in aqueous solutions. This reaction is often used to mask such ions before

complexometric titration Complexometric titration (sometimes chelatometry) is a form of volumetric analysis in which the formation of a colored complex is used to indicate the end point of a titration. Complexometric titrations are particularly useful for the determinat ...

s with another

chelating Chelation () is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate (multiple bonded) ligand and a single central metal atom. These l ...

agent such as

EDTA Ethylenediaminetetraacetic acid (EDTA), also called EDTA acid, is an aminopolycarboxylic acid with the formula . This white, slightly water-soluble solid is widely used to bind to iron (Fe2+/Fe3+) and calcium ions (Ca2+), forming water-solubl ...

. TEOA has also been used in

photographic Photography is the art, application, and practice of creating 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 in many ...

(

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 wit ...

) processing. It has been promoted as a useful alkali by amateur photographers.

In holography

TEOA is used to provide a sensitivity boost to silver-halide-based

hologram Holography is a technique that allows a wavefront to be recorded and later reconstructed. It is best known as a method of generating three-dimensional images, and has a wide range of other uses, including data storage, microscopy, and interf ...

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 TEOA before squeegee and drying.

In electroless plating

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

In ultrasonic testing

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

In aluminium soldering

Triethanolamine,

and

aminoethylethanolamine Aminoethylethanolamine or AEEA is an organic base used in the industrial manufacture of fuel and oil additives, chelating agents, and surfactants. Synthesis AEEA may be produced by the ethoxylation of ethylenediamine in the presence of water ...

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, are various conditions caused by hypersensitivity of the immune system to typically harmless substances in the environment. These diseases include Allergic rhinitis, hay fever, Food allergy, food al ...

. A 2001 study found TEOA in a

sunscreen Sunscreen, also known as sunblock, sun lotion or sun cream, is a photoprotection, photoprotective topical product for the Human skin, skin that helps protect against sunburn and prevent skin cancer. Sunscreens come as lotions, sprays, gels, fo ...

caused an allergic contact

dermatitis Dermatitis is a term used for different types of skin inflammation, 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 ...

. 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 u ...

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 A patch test is a diagnostic method used to determine which specific substances cause allergic inflammation of a patient's skin. Patch testing helps identify which substances may be causing a delayed-type allergic reaction in a patient and ...

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, although higher-primates are known to have higher resistance to the tumotigenesis. 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 Hydroxyethyl compounds Concrete admixtures