Diethylamine

Diethylamine is an organic compound with the formula (CH3CH2)2NH. It is a secondary amine. It is a flammable, weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear brown due to impurities. It has a strong ammonia-like odor.

Diethylamine[1]
Names
Preferred IUPAC name
N-Ethylethanamine
Other names
(Diethyl)amine
Diethylamine (deprecated[2])
Identifiers
3D model (JSmol)
605268
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.380
EC Number
  • 203-716-3
MeSH diethylamine
RTECS number
  • HZ8750000
UNII
UN number 1154
Properties
C4H11N
Molar mass 73.139 g·mol−1
Appearance Colourless liquid
Odor fishy, ammonical
Density 0.7074 g mL−1
Melting point −49.80 °C; −57.64 °F; 223.35 K
Boiling point 54.8 to 56.4 °C; 130.5 to 133.4 °F; 327.9 to 329.5 K
Miscible
log P 0.657
Vapor pressure 24.2–97.5 kPa
150 μmol Pa−1 kg−1
Acidity (pKa) 10.98 (of ammonium form)
-56.8·10−6 cm3/mol
1.385
Thermochemistry
178.1 J K−1 mol−1
Std enthalpy of
formation (ΔfH⦵298)
 −131 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −3.035 MJ mol−1
Hazards
Safety data sheet hazard.com
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H225, H302, H312, H314, H332
P210, P280, P305+351+338, P310
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
3
1
Flash point −23 °C (−9 °F; 250 K)
312 °C (594 °F; 585 K)
Explosive limits 1.8–10.1%
Lethal dose or concentration (LD, LC):
540 mg/kg (rat, oral)
500 mg/kg (mouse, oral)[3]
4000 ppm (rat, 4 hr)[3]
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 25 ppm (75 mg/m3)[4]
REL (Recommended)
 TWA 10 ppm (30 mg/m3) ST 25 ppm (75 mg/m3)[4]
IDLH (Immediate danger)
 200 ppm[4]
Related compounds
Related amines
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Production and uses

Diethylamine is made by the alumina-catalyzed reaction of ethanol and ammonia. It is obtained together with ethylamine and triethylamine. Annual production of three ethylamines was estimated in 2000 to be 80,000,000 kg.[5]

It is used in the production of corrosion inhibitor N,N-diethylaminoethanol, by reaction with ethylene oxide. It is also a precursor to a wide variety of other commercial products.

Diethylamine is also sometimes used in the illicit production of LSD[6].

Supramolecular structure
Supramolecular helix of diethylamine

Diethylamine is the smallest and simplest molecule that features a supramolecular helix as its lowest energy aggregate. Other similarly sized hydrogen-bonding molecules favor cyclic structures.[7]

Safety

Diethylamine has low toxicity, but the vapor causes transient impairment of vision.[5]

gollark: I assume it's just because it is not trendy™.
gollark: Although that's maybe not guaranteed, I suppose.
gollark: So it looks like I can in fact get away with underscores, fun.
gollark: Some are metamorphic.
gollark: Only igneous apiopyroforms.

References
  1. Merck Index, 12th Edition, 3160
  2. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 671. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  3. "Diethylamine". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. NIOSH Pocket Guide to Chemical Hazards. "#0209". National Institute for Occupational Safety and Health (NIOSH).
  5. Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke (2005). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.CS1 maint: multiple names: authors list (link)
  6. Shulgin, Alexander. "Erowid Online Books:"TIHKAL" - #26 LSD-25". www.erowid.org. Retrieved 12 August 2019.
  7. Felix Hanke; Chloe J. Pugh; Ellis F. Kay; Joshua B. Taylor; Stephen M. Todd; Craig M. Robertson; Benjamin J. Slater; Alexander Steiner (2018). "The simplest supramolecular helix". Chemical Communications. 54. doi:10.1039/C8CC03295E.
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