Diethanolamine

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Diethanolamine
Skeletal formula of diethanolamine
Ball-and-stick model of the diethanolamine molecule
Names
Preferred IUPAC name
2,2′-Azanediyldi(ethan-1-ol)
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
)
3DMet
605315
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.003.517 Edit this at Wikidata
EC Number
  • 203-868-0
KEGG
MeSH diethanolamine
RTECS number
  • KL2975000
UNII
  • InChI=1S/C4H11NO2/c6-3-1-5-2-4-7/h5-7H,1-4H2 checkY
    Key: ZBCBWPMODOFKDW-UHFFFAOYSA-N checkY
  • OCCNCCO
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
1.477
Thermochemistry
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:
GHS05: Corrosive GHS07: Exclamation mark GHS08: Health hazard
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):
  • 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)
NIOSH (US health exposure limits):
PEL (Permissible)
 None[1]
REL (Recommended)
 TWA: 3 ppm (15 mg/m3)[1]
IDLH
(Immediate danger)
 N.D.[1]
Safety data sheet (SDS) sciencelab.com
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).
checkY verify (what is checkY☒N ?)

Diethanolamine, often abbreviated as DEA or DEOA, is an

Group 2B
).

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.

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

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

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 contain DEA.[8] 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.[9] One study showed that DEA inhibits in baby mice the absorption of choline, which is necessary for brain development and maintenance;[10] 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".[11] 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.[12] A 2009 study found that DEA has potential acute, chronic and subchronic toxicity properties for aquatic species.[13]

References

  1. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0208". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "Akzo-Nobel data sheet" (PDF). Archived from the original (PDF) on 2018-09-20. Retrieved 2013-08-14.
  3. ^
    doi:10.1002/14356007.a10_001
  4. ^
    ISBN 978-3-527-30578-0
    .
  5. ^ Diethanolamine. International Agency for Research on Cancer. 2013.
  6. ^ 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
  7. doi:10.1007/BF02699621
    .
  8. ^ "Lauramide DEA | Cosmetics Info".
  9. PMID 19397616
    .
  10. ^ Study Shows Ingredient Commonly Found In Shampoos May Inhibit Brain Development
  11. PMID 18948303
    .
  12. PMID 18420328
    .
  13. PMID 20022426
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Diethanolamine&oldid=1214529280"