Names | |
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Preferred IUPAC name 2,2′-Azanediyldi(ethan-1-ol) | |
Other names
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Identifiers | |
3D model (JSmol) | |
3DMet | |
605315 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.003.517 |
EC Number |
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KEGG | |
MeSH | diethanolamine |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C4H11NO2 | |
Molar mass | 105.137 g·mol−1 |
Appearance | Colourless crystals |
Odor | Ammonia odor |
Density | 1.097 g·mL−1 |
Melting point | 28.00 °C; 82.40 °F; 301.15 K |
Boiling point | 271.1 °C; 519.9 °F; 544.2 K |
Miscible | |
log P | -1.761 |
Vapor pressure | <1 Pa (at 20 °C) |
UV-vis (λmax) | 260 nm |
Refractive index (nD) | 1.477 |
Thermochemistry | |
Heat capacity (C) | 137 J·K−1·mol−1 |
Std enthalpy of formation (ΔfH⦵298) | −496.4 – −491.2 kJ·mol−1 |
Std enthalpy of combustion (ΔcH⦵298) | −26.548 – −26.498 MJ·kmol−1 |
Hazards | |
GHS labelling: | |
Danger | |
H302, H315, H318, H373 | |
P280, P305+P351+P338 | |
Flash point | 138 °C (280 °F; 411 K) |
365 °C (689 °F; 638 K) | |
Explosive limits | 1.6–9.8% [1] |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
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NIOSH (US health exposure limits): | |
PEL (Permissible) | None [1] |
REL (Recommended) | TWA: 3 ppm (15 mg/m3) [1] |
IDLH (Immediate danger) | N.D. [1] |
Safety data sheet (SDS) | sciencelab.com |
Related compounds | |
Related alkanols | |
Related compounds | Diethylhydroxylamine |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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 [2] often results in it being found in a colorless, viscous liquid state. Diethanolamine is polyfunctional, being a secondary amine and a diol. Like other organic amines, diethanolamine acts as a weak base. 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).
The reaction of ethylene oxide with aqueous ammonia first produces ethanolamine:
which reacts with a second and third equivalent of ethylene oxide to give DEA and triethanolamine:
About 300M kg are produced annually in this way. [3] The ratio of the products can be controlled by changing the stoichiometry of the reactants. [4]
DEA is used as a surfactant and a corrosion inhibitor. It is used to remove hydrogen sulfide and carbon dioxide 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. [5] In oil refineries, a DEA in water solution is commonly used to remove hydrogen sulfide from sour gas. 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 hydrogen sulfide at a lower circulating amine rate with less overall energy usage.
DEA is a chemical feedstock used in the production of morpholine. [3] [4]
Amides derived from DEA and fatty acids, known as diethanolamides, are amphiphilic.
The reaction of 2-chloro-4,5-diphenyloxazole with DEA gave rise to ditazole. The reaction of DEA and isobutyraldehyde with water removed produces an oxazolidine. [6] [7]
DEA is used in the production of diethanolamides, which are common ingredients in cosmetics and shampoos added to confer a creamy texture and foaming action. Consequently, some cosmetics that include diethanolamides as ingredients contain DEA. [8] Some of the most commonly used diethanolamides include:
DEA is a potential skin irritant in workers sensitized by exposure to water-based metalworking fluids. [9] One study showed that DEA inhibits in baby mice the absorption of choline, which is necessary for brain development and maintenance; [10] 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". [11] 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. [12] A 2009 study found that DEA has potential acute, chronic and subchronic toxicity properties for aquatic species. [13]
Ethylene oxide is an organic compound with the formula C2H4O. 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 sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of a silver catalyst.
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, and in cosmetics as an emulsifying agent. See cocamide for the discussion of the lengths of carbon chains in the molecules in the mixture. The chemical formula of individual components is CH3(CH2)nC(=O)N(CH2CH2OH)2, where n typically ranges from 8 to 18.
Ethanolamine is a naturally occurring organic chemical compound with the formula HOCH
2CH
2NH
2 or C
2H
7NO. The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia.
N-Methylethanolamine is an alkanolamine with the formula CH3NHCH2CH2OH. It is flammable, corrosive, colorless, viscous liquid. It is an intermediate in the biosynthesis of choline.
In organic chemistry, ethoxylation is a chemical reaction in which ethylene oxide adds to a substrate. It is the most widely practiced alkoxylation, which involves the addition of epoxides to substrates.
1,4-Dioxane is a heterocyclic organic compound, classified as an ether. It is a colorless liquid with a faint sweet odor similar to that of diethyl ether. The compound is often called simply dioxane because the other dioxane isomers are rarely encountered.
Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH. This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, treating morpholine with hydrochloric acid makes the salt morpholinium chloride. It is a colorless liquid with a weak, ammonia- or fish-like odor. The naming of morpholine is attributed to Ludwig Knorr, who incorrectly believed it to be part of the structure of morphine.
Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA is also a common abbreviation. It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia. Like diisopropylethylamine (Hünig's base), triethylamine is commonly employed in organic synthesis, usually as a base.
Choline chloride is an organic compound with the formula [(CH3)3NCH2CH2OH]+Cl−. It is a quaternary ammonium salt, consisting of choline cations and chloride anions. It is a bifunctional compound, meaning, it contains both a quaternary ammonium functional group and a hydroxyl functional group. The cation of this salt, choline, occurs in nature in living beings. Choline chloride is a white, water-soluble salt used mainly in animal feed.
Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.
Diethylenetriamine (abbreviated Dien or DETA) and also known as 2,2’-Iminodi(ethylamine)) is an organic compound with the formula HN(CH2CH2NH2)2. This colourless hygroscopic liquid is soluble in water and polar organic solvents, but not simple hydrocarbons. Diethylenetriamine is structural analogue of diethylene glycol. Its chemical properties resemble those for ethylene diamine, and it has similar uses. It is a weak base and its aqueous solution is alkaline. DETA is a byproduct of the production of ethylenediamine from ethylene dichloride.
Triethanolamine, or TEOA, is an organic compound with the chemical formula N(CH2CH2OH)3. It is a colourless, viscous liquid. It 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 may appear yellow because of impurities.
2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.
Glycidol is an organic compound that contains both epoxide and alcohol functional groups. Being bifunctional, it has a variety of industrial uses. The compound is a slightly viscous liquid that is slightly unstable and is not often encountered in pure form.
Cyclohexylamine is an organic compound, belonging to the aliphatic amine class. It is a colorless liquid, although, like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like other amines, it is a weak base, compared to strong bases such as NaOH, but it is a stronger base than its aromatic analog, aniline.
n-Butylamine is an organic compound (specifically, an amine) with the formula CH3(CH2)3NH2. This colourless liquid is one of the four isomeric amines of butane, the others being sec-butylamine, tert-butylamine, and isobutylamine. It is a liquid having the fishy, ammonia-like odor common to amines. The liquid acquires a yellow color upon storage in air. It is soluble in all organic solvents. Its vapours are heavier than air and it produces toxic oxides of nitrogen during combustion.
Aminoethylpiperazine (AEP) is a derivative of piperazine. This ethyleneamine contains three nitrogen atoms; one primary, one secondary and one tertiary. It is a corrosive organic liquid and can cause second or third degree burns. Aminoethylpiperazine can also cause pulmonary edema as a result of inhalation. It is REACH and TSCA registered.
Methyldiethanolamine, also known as N-methyl diethanolamine and more commonly as MDEA, is the organic compound with the formula CH3N(C2H4OH)2. It is a colorless liquid with an ammonia odor. It is miscible with water, ethanol and benzene. A tertiary amine, it is widely used as a sweetening agent in chemical, oil refinery, syngas production and natural gas.
Diethylethanolamine (DEAE) is the organic compound with the molecular formula (C2H5)2NCH2CH2OH. A colorless liquid, is used as a precursor in the production of a variety of chemical commodities such as the local anesthetic procaine.
Dicyclohexylamine is a secondary amine with the chemical formula HN(C6H11)2. It is a colorless liquid, although commercial samples can appear yellow. It has a fishy odor, typical for amines. It is sparingly soluble in water. As an amine, it is an organic base and useful precursor to other chemicals.