Diethanolamine, often abbreviated as DEA or DEOA, is an

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 ...

with the formula HN(CH₂CH₂OH)₂. Pure diethanolamine is a white solid at

room temperature Colloquially, "room temperature" is a range of air temperatures that most people prefer for indoor settings. It feels comfortable to a person when they are wearing typical indoor clothing. Human comfort can extend beyond this range depending on ...

, but its tendencies to absorb water and to

supercool Supercooling, also known as undercooling, is the process of lowering the temperature of a liquid or a gas below its melting point without it becoming a solid. It achieves this in the absence of a seed crystal or nucleus around which a crystal ...

meaning that it is often encountered as a colorless, viscous liquid. Diethanolamine is polyfunctional, being a secondary

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 Amines are formally derivatives of ammonia (), wherein one or more hydrogen atoms have been replaced by a substituent ...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

diol A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. The most common industrial diol is e ...

. Like other organic amines, diethanolamine acts as a

weak base A weak base is a base that, upon dissolution in water, does not dissociate completely, so that the resulting aqueous solution contains only a small proportion of hydroxide ions and the concerned basic radical, and a large proportion of undissociat ...

. Reflecting the hydrophilic character of the secondary amine and hydroxyl groups, DEA is soluble in water. Amides prepared from DEA are often also hydrophilic. In 2013, the chemical was classified by the International Agency for Research on Cancer as "possibly carcinogenic to humans" ( Group 2B).

Production

The reaction of

ethylene oxide Ethylene oxide is an organic compound with the formula . It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sw ...

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 ...

first produces ethanolamine: :C₂H₄O + NH₃ → H₂NCH₂CH₂OH which reacts with a second and third equivalent of ethylene oxide to give DEA and

triethanolamine 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 groups. Approximately 150,000 tonnes were produced in 1999. It is a colourless compound although samples m ...

: :C₂H₄O + H₂NCH₂CH₂OH → HN(CH₂CH₂OH)₂ :C₂H₄O + HN(CH₂CH₂OH)₂ → N(CH₂CH₂OH)₃ About 300M kg are produced annually in this way.Matthias Frauenkron, Johann-Peter Melder, Günther Ruider, Roland Rossbacher, Hartmut Höke “Ethanolamines and Propanolamines” in Ullmann's Encyclopedia of Industrial Chemistry 2002 by Wiley-VCH, Weinheim 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.

Uses

DEA is used as a surfactant and a

corrosion inhibitor In chemistry, a corrosion inhibitor or anti-corrosive is a chemical compound that, when added to a liquid or gas, decreases the corrosion rate of a material, typically a metal or an alloy, that comes into contact with the fluid. The effectiveness ...

. It is used to remove

hydrogen sulfide Hydrogen sulfide is a chemical compound with the formula . It is a colorless chalcogen-hydride gas, and is poisonous, corrosive, and flammable, with trace amounts in ambient atmosphere having a characteristic foul odor of rotten eggs. The under ...

and

carbon dioxide Carbon dioxide ( chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is t ...

from natural gas. Diethanolamine is widely used in the preparation of diethanolamides and diethanolamine salts of long-chain fatty acids that are formulated into soaps and surfactants used in liquid laundry and dishwashing detergents, cosmetics, shampoos and hair conditioners. In oil refineries, a DEA in water solution is commonly used to remove

from

sour gas Sour gas is natural gas or any other gas containing significant amounts of hydrogen sulfide (H2S). Natural gas is usually considered sour if there are more than 5.7 milligrams of H2S per cubic meter of natural gas, which is equivalent to approxim ...

. It has an advantage over a similar amine, ethanolamine, in that a higher concentration may be used for the same corrosion potential. This allows refiners to scrub

at a lower circulating amine rate with less overall energy usage. DEA is a chemical feedstock used in the production of

morpholine Morpholine is an organic chemical compound having the chemical formula O( C H2CH2)2 NH. This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. Fo ...

. :

Amides derived from DEA and

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, known as diethanolamides, are

amphiphilic An amphiphile (from the Greek αμφις amphis, both, and φιλíα philia, love, friendship), or amphipath, is a chemical compound possessing both hydrophilic (''water-loving'', polar) and lipophilic (''fat-loving'') properties. Such a compo ...

. The reaction of 2-chloro-4,5-diphenyloxazole with DEA gave rise to

Ditazole Ditazole is a non-steroidal anti-inflammatory agent with analgesic and antipyretic activity similar to phenylbutazone. It is also a platelet aggregation inhibitor Inhibitor or inhibition may refer to: In biology * Enzyme inhibitor, a substance ...

. The reaction of DEA and

Isobutyraldehyde Isobutyraldehyde is the chemical compound with the formula (CH3)2CHCHO. It is an aldehyde, isomeric with n-butyraldehyde (butanal). Isobutyraldehyde is made, often as a side-product, by the hydroformylation of propene. Its odour is described as ...

with water removed produces an Oxazolidine.

Commonly used ingredients that may contain DEA

DEA is used in the production of diethanolamides, which are common ingredients in

cosmetics Cosmetics are constituted mixtures of chemical compounds derived from either natural sources, or synthetically created ones. Cosmetics have various purposes. Those designed for personal care and skin care can be used to cleanse or protec ...

and

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 ...

s added to confer a creamy texture and foaming action. Consequently, some cosmetics that include diethanolamides as ingredients contain DEA. Some of the most commonly used diethanolamides include: :*

Cocamide DEA Cocamide DEA, or cocamide diethanolamine, is a diethanolamide made by reacting the mixture of fatty acids from coconut oils with diethanolamine. It is a viscous liquid and is used as a foaming agent in bath products like shampoos and hand soaps, a ...

:* DEA-Cetyl Phosphate :* DEA Oleth-3 Phosphate :* Lauramide DEA :* Myristamide DEA :* Oleamide DEA

Safety

DEA is a potential skin irritant in workers sensitized by exposure to water-based metalworking fluids. One study showed that DEA inhibits in baby mice the absorption of

choline Choline is an essential nutrient for humans and many other animals. Choline occurs as a cation that forms various salts (X− in the depicted formula is an undefined counteranion). Humans are capable of some ''de novo synthesis'' of choline but r ...

, which is necessary for brain development and maintenance; however, a study in humans determined that dermal treatment for 1 month with a commercially available skin lotion containing DEA resulted in DEA levels that were "far below those concentrations associated with perturbed brain development in the mouse". In a mouse study of chronic exposure to inhaled DEA at high concentrations (above 150 mg/m³), DEA was found to induce body and organ weight changes, clinical and histopathological changes, indicative of mild blood, liver, kidney and testicular systemic toxicity. A 2009 study found that DEA has potential acute, chronic and subchronic toxicity properties for aquatic species.

References

{{Reflist

External links

Chemical safety card for DEA

Products containing diethanolamine, from U.S. Department of Health & Human Services

Brief technical specification of diethanolamine

Brief technical specification of diethanolamine pure
Diols Endocrine disruptors IARC Group 2B carcinogens Secondary amines Ethanolamines