Skeletal formula | |||
Ball and stick diagram | |||
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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]
DEA has potential toxicity properties for aquatic species. [10]
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 of surface-active agent, coined c. 1950. As they consist of a water-repellent and a water-attracting part, they enable water and oil to mix; they can form foam and facilitate the detachment of dirt.
Corrosion is a natural process that converts a refined metal into a more chemically stable oxide. It is the gradual deterioration of materials by chemical or electrochemical reaction with their environment. Corrosion engineering is the field dedicated to controlling and preventing corrosion.
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.
Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.
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 generates 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.
Maleic anhydride is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a large scale for applications in coatings and polymers.
Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.
Polypropylene glycol or polypropylene oxide is the polymer of propylene glycol. Chemically it is a polyether, and, more generally speaking, it's a polyalkylene glycol (PAG) H S Code 3907.2000. The term polypropylene glycol or PPG is reserved for polymer of low- to medium-range molar mass when the nature of the end-group, which is usually a hydroxyl group, still matters. The term "oxide" is used for high-molar-mass polymer when end-groups no longer affect polymer properties. Between 60 and 70% of propylene oxide is converted to polyether polyols by the process called alkoxylation.
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.
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.
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.
Paint has four major components: pigments, binders, solvents, and additives. Pigments serve to give paint its color, texture, toughness, as well as determining if a paint is opaque or not. Common white pigments include titanium dioxide and zinc oxide. Binders are the film forming component of a paint as it dries and affects the durability, gloss, and flexibility of the coating. Polyurethanes, polyesters, and acrylics are all examples of common binders. The solvent is the medium in which all other components of the paint are dissolved and evaporates away as the paint dries and cures. The solvent also modifies the curing rate and viscosity of the paint in its liquid state. There are two types of paint: solvent-borne and water-borne paints. Solvent-borne paints use organic solvents as the primary vehicle carrying the solid components in a paint formulation, whereas water-borne paints use water as the continuous medium. The additives that are incorporated into paints are a wide range of things which impart important effects on the properties of the paint and the final coating. Common paint additives are catalysts, thickeners, stabilizers, emulsifiers, texturizers, biocides to fight bacterial growth, etc.
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.