Diethanolamine
| Diethanolamine | |
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2,2'-Iminodiethanol |
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Other names
Diethanolamine, 2,2'-Iminobisethanol, Iminodiethanol, Bis(hydroxyethyl)amine, N,N-Bis(2-hydroxyethyl)amine, 2-[(2-Hydroxyethyl)amino]ethanol, 2,2'-Dihydroxydiethylamine, β,β'-Dihydroxydiethylamine, Diolamine, N-Ethylethanamine, DEA |
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| Identifiers | |
| CAS number | 111-42-2  |
| PubChem | 8113 |
| ChemSpider | 13835604 |
| UNII | AZE05TDV2V |
| EC number | 203-868-0 |
| KEGG | D02337 |
| ChEBI | CHEBI:28123 |
| ChEMBL | CHEMBL119604 |
| RTECS number | KL2975000 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H11NO2 |
| Molar mass | 105.14 g/mol |
| Density | 1.090 g/cm3 |
| Melting point |
28 °C, 301 K, 82 °F |
| Boiling point |
217 °C, 490 K, 423 °F |
| Solubility in water | Soluble |
| Vapor pressure | < 0.01 hPa (20 °C) |
| Hazards | |
| MSDS | ScienceLab.com |
| R-phrases | R20/21/22 R36/37/38 |
| Flash point | 169 °C c.c. |
| Autoignition temperature |
370 °C |
| Explosive limits | 1.7 - 6.4 % |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Diethanolamine, often abbreviated as DEA, is an organic compound with the formula HN(CH2CH2OH)2. This colorless liquid 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 alcohol groups, DEA is soluble in water, and is even hygroscopic. Amides prepared from DEA are often also hydrophilic.
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[edit] Production and uses
The reaction of ethylene oxide with aqueous ammonia first produces ethanolamine:
- C2H4O + NH3 → H2NCH2CH2OH
which reacts with a second and third equivalent of ethylene oxide to give DEA and triethanolamine:
- C2H4O + H2NCH2CH2OH → HN(CH2CH2OH)2
- C2H4O + HN(CH2CH2OH)2 → N(CH2CH2OH)3
About 300M kg are produced annually in this way.[1] The ratio of the products can be controlled by changing the stoichiometry of the reactants.[2]
DEA is used as a surfactant and a corrosion inhibitor. It is used to remove hydrogen sulfide and carbon dioxide from natural gas.
In oil refineries, a DEA in water solution is commonly used to remove hydrogen sulfide from various process gases. 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 versatile chemical intermediate, principal derivatives include ethyleneimine and ethylenediamine.[1] Dehydration of DEA with sulfuric acid gives morpholine:[2]
Amides derived from DEA and fatty acids, known as diethanolamides, are amphiphilic.
[edit] Commonly used ingredients that may contain DEA
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 may contain traces of DEA.[citation needed] Some of the most commonly used diethanolamides include:
[edit] Safety
DEA is a potential skin irritant in workers sensitized by exposure to water-based metalworking fluids.[3] One study showed that DEA inhibits in baby mice the absorption of choline, which is necessary for brain development and maintenance;[4] 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".[5] 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.[6] A 2009 study found that DEA has potential acute, chronic and subchronic toxicity properties for aquatic species.[7]
[edit] References
- ^ a b Matthias Frauenkron, Johann-Peter M elder, Günther Ruider, Roland Rossbacher, Hartmut Höke “Ethanolamines and Propanolamines” in Ullmann's Encyclopedia of Industrial Chemistry 2002 by Wiley-VCH, Weinheim doi:10.1002/14356007.a10_001
- ^ a b Klaus Weissermel, Hans-Jürgen Arpe, Charlet R. Lindley, Stephen Hawkins (2003). "Chap. 7. Oxidation Products of Ethylene". Industrial Organic Chemistry. Wiley-VCH. pp. 159–161. ISBN 3527305785.
- ^ Lessmann H, Uter W, Schnuch A, Geier J (2009). "Skin sensitizing properties of the ethanolamines mono-, di-, and triethanolamine. Data analysis of a multicentre surveillance network (IVDK*) and review of the literature". Contact Dermatitis 60 (5): 243–255. doi:10.1111/j.1600-0536.2009.01506.x. PMID 19397616.
- ^ Study Shows Ingredient Commonly Found In Shampoos May Inhibit Brain Development
- ^ Craciunescu, CN; Niculescu, MD; Guo, Z; Johnson, AR; Fischer, L; Zeisel, SH (2009). "Dose response effects of dermally applied diethanolamine on neurogenesis in fetal mouse hippocampus and potential exposure of humans.". Toxicological sciences : an official journal of the Society of Toxicology 107 (1): 220–6. doi:10.1093/toxsci/kfn227. PMC 2638646. PMID 18948303. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2638646.
- ^ Gamer AO, Rossbacher R, Kaufmann W, van Ravenzwaay B (2008). "The inhalation toxicity of di- and triethanolamine upon repeated exposure". Food Chem Toxicol 46 (6): 2173–83. doi:10.1016/j.fct.2008.02.020. PMID 18420328.
- ^ Libralato G, Volpi Ghirardini A, Avezzù F (2009). "Seawater ecotoxicity of monoethanolamine, diethanolamine and triethanolamine". J Hazard Mater 176 (1–3): 535–9. doi:10.1016/j.jhazmat.2009.11.062. PMID 20022426.
