Diethanolamine

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Diethanolamine
Skeletal formula of diethanolamine
Other names

2,2'-Iminodiethanol[citation needed]

Identifiers
CAS number 111-42-2 7pxY
PubChem 8113
ChemSpider 13835604 7pxY
UNII AZE05TDV2V 7pxY
EC number 203-868-0
KEGG D02337 7pxY
MeSH diethanolamine
ChEBI CHEBI:28123 7pxY
ChEMBL CHEMBL119604 7pxY
RTECS number KL2975000
Beilstein Reference 605315
3DMet B01050
Jmol-3D images Image 1
Thermochemistry
Std enthalpy of
formation ΔfHo298 		−496.4–−491.2 kJ mol−1
Std enthalpy of
combustion ΔcHo298 		−2.6548–−2.6498 MJ mol−1
Specific heat capacity, C 137 J K−1 mol−1
Hazards
MSDS 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
GHS hazard statements H302, H315, H318, H373
GHS precautionary statements P280, P305+351+338
EU Index 603-071-00-1
EU classification Harmful Xn
R-phrases R22, R38, R41, R48/22
S-phrases (S2), S26, S36/37/39
Flash point 138 °C
Autoignition
temperature 		365 °C
Explosive limits 1.6–10.6%
LD50
  • 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)
Related compounds
Related alkanols
Related compounds
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

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]

400px

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.[citation needed] 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.[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]

References

  1. ↑ 1.0 1.1 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
  2. ↑ 2.0 2.1 Script error
  3. ↑ Script error
  4. ↑ Study Shows Ingredient Commonly Found In Shampoos May Inhibit Brain Development
  5. ↑ Script error
  6. ↑ Script error
  7. ↑ Script error

External links

fa:دی‌اتانول‌آمین fr:Diéthanolamine it:Dietanolammina nl:Diethanolamine ja:ジエタノールアミン pt:Dietanolamina ru:Диэтаноламин


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