Diethanolamine
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| Diethanolamine | |
|---|---|
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| IUPAC name | 2,2'-Iminodiethanol |
| 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 |
| Identifiers | |
| CAS number | [111-42-2] |
| PubChem | |
| EINECS number | |
| ChEBI | |
| RTECS number | KL2975000 |
| SMILES | OCCNCCO |
| InChI | 1/C4H11NO2/c6-3-1-5-2-4-7/h5-7H,1-4H2 |
| Properties | |
| Molecular formula | C4H11NO2 |
| Molar mass | 105.14 g/mol |
| Density | 1.090 g/cm3 |
| Melting point |
28.0 °C |
| Boiling point |
217 °C |
| Solubility in water | Soluble |
| Vapor pressure | < 0.01 hPa (20 °C) |
| Hazards | |
| MSDS | Oxford MSDS |
| R-phrases | R20/21/22, R36/37/38 |
| Flash point | 169 °C c.c. |
| Autoignition temperature |
370 °C |
| Explosive limits | 1.7 - 6.4 % |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Diethanolamine, often abbreviated as DEA, is an organic chemical compound which is both a secondary amine and a dialcohol. A dialcohol has two hydroxyl groups in its molecule. Like other amines, diethanolamine acts as a weak base.
Other names or synonyms are bis(hydroxyethyl)amine, diethylolamine, hydroxydiethylamine, diolamine, and 2,2'-iminodiethanol.
DEA and its chemical variants are common ingredients in cosmetics and shampoos, where they are used as to create a creamy texture and foaming action. Variants of DEA include lauramide diethanolamine, coco diethanolamide, cocoamide diethanolamine or coconut oil amide of diethanolamine, lauramide DEA, lauric diethanolamide, lauroyl diethanolamide, and lauryl diethanolamide.
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[edit] Production
Monoethanolamine is produced by reacting ethylene oxide with aqueous ammonia; the reaction also produces diethanolamine and triethanolamine. the ratio of the products can be controlled by changing the stoichiometry of the reactants.[1]
[edit] Reactions
Morpholine may be produced by the dehydration of DEA with sulfuric acid:[1]
[edit] Safety
DEA and its variants are suspected of increasing the risk of cancer. DEA can combine with amines present in cosmetic formulations to form nitrosamines (N-nitrosodiethanolamine), which are known to be highly carcinogenic.[2] Studies also show that DEA directly inhibits fetal brain development in mice by blocking the absorption of choline, a nutrient required for brain development and maintenance.[3] DEA is also associated with miscarriages in laboratory studies.
It is also hygroscopic, so should be stored in an anhydrous environment whenever possible.
[edit] References
- ^ a b Klaus Weissermel, Hans-Jürgen Arpe, Charlet R. Lindley, Stephen Hawkins (2003). "Chap. 7. Oxidation Products of Ethylene", Industrial Organic Chemistry. Wiley-VCH, 159-161. ISBN 3527305785.
- ^ Prevent Cancer website entry on DEA
- ^ Study Shows Ingredient Commonly Found In Shampoos May Inhibit Brain Development
[edit] External links
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