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).
 Skeletal formula
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 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)
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| 605315 | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider | |||
| ECHA InfoCard | 100.003.517 | ||
| EC Number |
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| KEGG | |||
| MeSH | diethanolamine | ||
PubChem CID
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| 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)
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1.477 | ||
| Thermochemistry | |||
Heat capacity (C)
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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: | |||
  
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| 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)
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None[1] | ||
REL (Recommended)
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TWA: 3 ppm (15 mg/m3)[1] | ||
IDLH (Immediate danger)
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N.D.[1] | ||
| Safety data sheet (SDS) | sciencelab.com | ||
| Related compounds | |||
Related alkanols
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Related compounds
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Diethylhydroxylamine | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Production
editThe 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.[3] The ratio of the products can be controlled by changing the stoichiometry of the reactants.[4]
Uses
editDEA 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]
Commonly used ingredients that may contain DEA
editDEA 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:
Safety and environment
editDEA 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]
References
edit- ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0208". National Institute for Occupational Safety and Health (NIOSH).
- ^ "Akzo-Nobel data sheet" (PDF). Archived from the original (PDF) on 2018-09-20. Retrieved 2013-08-14.
- ^ a b 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 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 978-3-527-30578-0.
- ^ Diethanolamine. International Agency for Research on Cancer. 2013.
- ^ Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" Master of Science Thesis April 1997 Imperial College London
- ^ Howarth, GA (2003). "Polyurethanes, polyurethane dispersions and polyureas: Past, present and future". Surface Coatings International Part B: Coatings Transactions. 86 (2): 111–118. doi:10.1007/BF02699621.
- ^ "Lauramide DEA | Cosmetics Info".
- ^ 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.
- ^ 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.