Alkylamines
| Alkylamines |
|---|
 Methylamine |
 Ethylamine |
Alkylamines form a group of organochemical compounds that are derived from ammonia (NH 3 ), one of the three hydrogen atoms of which has been replaced by an alkyl radical R. The alkylamines have the general formula C n H 2n +1 NH 2 .
The term alkylamine is not IUPAC compliant, but is widely used. The common names of many aminoalkanes are based on the term alkylamine. The best known are alkylamines
- Methylamine [CH 3 NH 2 ] - also called aminomethane - and
- Ethylamine [C 2 H 5 NH 2 ] - also called aminoethane.
Manufacturing
Potassium phthalimide reacts with a haloalkane to form the corresponding N -alkylphthalimide, which reacts in several reaction steps by hydrolysis or hydrazinolysis to form the alkylamine - a primary amine:
This reaction sequence is called the Gabriel synthesis . It is a purely laboratory process. Because of the formation of stoichiometric amounts of several waste materials , the atom economy of the Gabriel synthesis is so bad that nobody realizes a technical synthesis for primary amines based on this reaction.
Another way of presenting alkylamines with higher atom economy is the reaction of the haloalkane with sodium azide to form the alkyl azide , from which the alkylamine can then be obtained reductively (e.g. with lithium aluminum hydride ). The reaction of the haloalkane with sodium cyanide with subsequent reduction to the alkylamine takes place with chain extension .
properties
Alkylamines form salts with mineral acids. With hydrochloric acid (HCl) react z. B. Methylamine in a neutralization reaction to a hydrochloride :
See also
Individual evidence
- ↑ K. Peter C. Vollhardt: Organic Chemistry , VCH, Weinheim 1990, ISBN 3-527-26912-6 , p. 1100.
- ↑ L. Kürti, B. Czakó: Strategic Applications Of Named Reactions In Organic Synthesis . Elsevier Academic Press, USA 2005, pp. 182 .