Triethylamine

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Triethylamine
Triethylamine distilled by NurdRage.jpg
Freshly distilled triethylamine
Triethylamine structure.gif
Structure of triethylamine
Names
Preferred IUPAC name
N,N-Diethylethanamine
Other names
(Diethylamino)ethane
(Triethyl)amine
Properties
C6H15N
N(CH2CH3)3
NEt3
Molar mass 101.19 g/mol
Appearance Colorless liquid
Odor Fishy
Density 0.7255 g/cm3
Melting point −114.7 °C (−174.5 °F; 158.5 K)
Boiling point 88.8 °C (191.8 °F; 361.9 K)
Miscible (<18.7 °C)
5.5 g/100 ml (20 °C)
6.86 g/100 ml (25 °C)
Solubility Miscible with acetone, diethyl ether, ethanol
Soluble in benzene, carbon tetrachloride, chloroform, mineral and natural oils
Vapor pressure 6.899–8.506 kPa
Thermochemistry
−169 kJ/mol
Hazards
Safety data sheet Sigma-Aldrich
Flash point −15 °C (5 °F; 258 K)
Lethal dose or concentration (LD, LC):
580 mg/kg (rabbit, dermal)
730 mg/kg (rat, oral)
Related compounds
Related compounds
Methylamine
Diethylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Triethylamine is an amine, with the formula N(CH2CH3)3 or NEt3. Pure triethylamine exists as a liquid at room temperature.

Properties

Physical

Triethylamine is a colorless liquid with a melting point of -114.7 °C and a boiling point around 88.6 °C. It has a strong, fishy odor reminiscent of ammonia.

Chemical

Triethylamine is a base commonly used in organic chemistry to prepare esters and amides from acyl chlorides.Like other tertiary amines,it catalyzes the formation of urethane foams and epoxy resins.

Availability

It is sold by chemical suppliers.

Preparation

There are many ways to make triethylamine, though only a few are efficient.

THIS SIMPLIFIED OUTLINE STILL NEEDS IMPROVEMENT. FOR A FULL PROCEDURE,SEE THE LINKED REFERENCE.

Triethylamine can be prepared by heating ethyl bromide and anhydrous ammonia in absolute ethanol in an oven for three hours, removing the product, distilling off the alcohol, and adding hydrochloric acid to the product to convert it to its hydrochloride salt. Melt the triethylamine hydrochloride and filter off the ammonium chloride crystals that remain. After filtering, freebase the triethylamine and once again add ethyl bromide. Heat in a steam oven for three hours and allow it to slowly cool. Remove the resulting liquid.[1]

Projects

  • Quaternary ammonium compounds
  • Anesthetize mosquitoes

Handling

Safety and toxicity

Triethylamine is a toxic liquid.

Legal issues

Storage

Triethylamine should be stored in a special cabinet, away from any heat source.

Disposal

Triethylamine can be diluted with a flammable solvent and burned in an open place.

Adding an acid will convert it to salt, which is easier to dispose of.

References

  1. http://www.sciencemadness.org/talk/files.php?pid=233855&aid=17257

Relevant Sciencemadness threads