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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]
Skeletal formula of diethylamine
Ball and stick model of the diethylamine molecule
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, ammoniacal
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
−131 kJ mol−1
−3.035 MJ mol−1
Hazards
Safety data sheet hazard.com
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) 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)
GHS signal word DANGER
H225, H302, H312, H314, H332
P210, P280, P305+351+338, P310
NFPA 704
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 codeNFPA 704 four-colored diamond
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)[4]
4000 ppm (rat, 4 hr)[4]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 25 ppm (75 mg/m3)[3]
REL (Recommended)
TWA 10 ppm (30 mg/m3) ST 25 ppm (75 mg/m3)[3]
IDLH (Immediate danger)
200 ppm[3]
Related compounds
Related amines
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Contents

Production and usesEdit

Diethylamine is manufactured 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.

Supramolecular structureEdit

 
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.[6]

SafetyEdit

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

ReferencesEdit

  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. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0209". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ a b "Diethylamine". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  5. ^ a b Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke "Amines, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a02_001
  6. ^ 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.

External linksEdit