Saturday 31 March 2018

Diethanolamine


Diethanolamine

From Wikipedia, the free encyclopedia
Diethanolamine
Skeletal formula of diethanolamine
Ball-and-stick model of the diethanolamine molecule
Names
IUPAC name
2,2'-Iminodiethanol
Other names
  • Bis(hydroxyethyl)amine
  • N,N-Bis(2-hydroxyethyl)amine
  • 2,2'-Dihydroxydiethylamine
  • β,β'-Dihydroxydiethylamine
  • Diolamine
  • 2-[(2-Hydroxyethyl)amino]ethanol
  • 2,2'-Iminobisethanol
  • Iminodiethanol
  • Di(2-hydroxyethyl)amine
  • bis(2-Hydroxyethyl)amine
  • 2,2'-Iminodiethanol
Identifiers
3D model (JSmol)
3DMetB01050
605315
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.003.517
EC Number203-868-0
KEGG
MeSHdiethanolamine
PubChem CID
RTECS numberKL2975000
UNII
Properties
C4H11NO2
Molar mass105.14 g·mol−1
AppearanceColourless crystals
OdorAmmonia odor
Density1.097 g·mL−1
Melting point28.00 °C; 82.40 °F; 301.15 K
Boiling point271.1 °C; 519.9 °F; 544.2 K
Miscible
log P1.761
Vapor pressure<1 Pa (at 20 °C)
UV-vis (λmax)260 nm
1.477
Thermochemistry
137 J·K−1·mol−1
−496.4 – −491.2 kJ·mol−1
−26.548 – −26.498 MJ·kmol−1
Hazards
Safety data sheetsciencelab.com
GHS pictogramsThe corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal wordDANGER
H302, H315, H318, H373
P280, P305+351+338
Flash point138 °C (280 °F; 411 K)
365 °C (689 °F; 638 K)
Explosive limits1.6–9.8%[1]
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 120 mg·kg−1 (intraperitoneal, rat)
  • 710 mg·kg−1 (oral, rat)
  • 778 mg·kg−1 (intravaneous, rat)
  • 12.2 g·kg−1 (dermal, rabbit)
US health exposure limits (NIOSH):
PEL(Permissible)
None[1]
REL(Recommended)
TWA: 3 ppm (15 mg/m3)[1]
IDLH (Immediate danger)
N.D.[1]
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).
Yes verify (what is Yes ?)
Infobox references
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 tendency to absorb water and to supercool[2] mean it is often encountered as a colorless, viscous liquid. 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. Recently, the chemical has been classified by the International Agency for Research on Cancer as "possibly carcinogenic to humans (Group 2B)".

Production[edit]

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.[3] The ratio of the products can be controlled by changing the stoichiometry of the reactants.[4]

Uses[edit]

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 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]
Morpholine from DEA.png
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.

Commonly used ingredients that may contain DEA[edit]

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:

Safety[edit]

DEA is a potential skin irritant in workers sensitized by exposure to water-based metalworking fluids.[5] One study showed that DEA inhibits in baby mice the absorption of choline, which is necessary for brain development and maintenance;[6] 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".[7] 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.[8] A 2009 study found that DEA has potential acute, chronic and subchronic toxicity properties for aquatic species.[9]

References[edit]

  1. ^ Jump up to:a b c d "NIOSH Pocket Guide to Chemical Hazards #0208". National Institute for Occupational Safety and Health (NIOSH).
  2. Jump up^ "Akzo-Nobel data sheet" (PDF). Retrieved 2013-08-14.
  3. ^ Jump up to: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
  4. ^ Jump up to: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 3-527-30578-5.
  5. Jump up^ 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.
  6. Jump up^ Study Shows Ingredient Commonly Found In Shampoos May Inhibit Brain Development
  7. Jump up^ 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. 107 (1): 220–6. doi:10.1093/toxsci/kfn227. PMC 2638646 Freely accessible. PMID 18948303.
  8. Jump up^ 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.
  9. Jump up^ 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.

External links[edit]

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