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Diethanolamine

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Diethanolamine

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
 Y
3DMet
605315
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
EC number 203-868-0
Jmol-3D images Image
KEGG  Y
MeSH
PubChem
RTECS number KL2975000
UNII  Y
Properties
C4H11NO2
Molar mass 105.14 g·mol−1
Appearance Colourless crystals
Odor Odourless
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-vismax) 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 sheet sciencelab.com
GHS pictograms The 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 word DANGER
H302, H315, H318, H373
P280, P305+351+338
Harmful Xn
R-phrases R22, R38, R41, R48/22
S-phrases (S2), S26, S36/37/39
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)
  • 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]
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).
 Y  (: Y/N?)

Diethanolamine, often abbreviated as DEA or DEOA, is an weak base. Reflecting the hydrophilic character of the alcohol groups, DEA is soluble in water. Amides prepared from DEA are often also hydrophilic.

Contents

  • Production 1
  • Uses 2
  • Commonly used ingredients that may contain DEA 3
  • Safety 4
  • References 5
  • External links 6

Production

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

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]

Amides derived from DEA and fatty acids, known as diethanolamides, are amphiphilic.

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. Some of the most commonly used diethanolamides include:

Safety

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

  • Chemical safety card for DEA
  • CDC - NIOSH Pocket Guide to Chemical Hazards
  • Toxicology and Carcinogenesis Studies
  • Products containing diethanolamine, from U.S. Department of Health & Human Services
  • Brief technical specification of diethanolamine
  • Brief technical specification of diethanolamine pure

External links

  1. ^ a b c d "NIOSH Pocket Guide to Chemical Hazards #0208".  
  2. ^ "Akzo-Nobel data sheet" (PDF). Retrieved 2013-08-14. 
  3. ^ 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. ^ a b Klaus Weissermel, Hans-Jürgen Arpe, Charlet R. Lindley, Stephen Hawkins (2003). "Chap. 7. Oxidation Products of Ethylene". Industrial Organic Chemistry.  
  5. ^ 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.  
  6. ^ Study Shows Ingredient Commonly Found In Shampoos May Inhibit Brain Development
  7. ^ 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.".  
  8. ^ 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.  
  9. ^ Libralato G, Volpi Ghirardini A, Avezzù F (2009). "Seawater ecotoxicity of monoethanolamine, diethanolamine and triethanolamine". J Hazard Mater 176 (1–3): 535–9.  

References

[9] A 2009 study found that DEA has potential acute, chronic and subchronic toxicity properties for aquatic species.[8]

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