Ethylamine
| Names | |
|---|---|
| IUPAC name
Ethanamine
| |
| Other names
Aminoethane
Monoethylamine | |
| Properties | |
| C2H7N CH3CH2NH2 | |
| Molar mass | 45.085 g/mol |
| Appearance | Colorless gas/liquid |
| Odor | Fishy, ammoniacal |
| Density | 688 g/cm3 (15 °C) (liquid) 1.61 g/cm3 (20 °C) (gas) 0.81 g/cm3 (20 °C) (70% aq. sol.) |
| Melting point | −81.2 °C (−114.2 °F; 192.0 K) |
| Boiling point | 16.6 °C (61.9 °F; 289.8 K) |
| Miscible | |
| Solubility | Reacts with acids Miscible with acetone, benzene, diethyl ether, ethanol, isopropanol, methanol, pyridine, toluene |
| Vapor pressure | 874 mmHg (20 °C) |
| Acidity (pKa) | 10.8 |
| Thermochemistry | |
| Std enthalpy of
formation (ΔfH |
−57.7 kJ/mol |
| Hazards | |
| Safety data sheet | Sigma-Aldrich (anhydrous) Sigma-Aldrich (70% aq. solution) |
| Flash point | −37 °C (−35 °F; 236 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
400 mg/kg (rat, oral) 265 mg/kg (rabbit, dermal) |
| LC50 (Median concentration)
|
1230 ppm (mammal) |
| Related compounds | |
| Related compounds
|
Methylamine Propylamine |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Ethylamine is an organic compound with the formula CH3CH2NH2 or just EtNH2.
Contents
Properties
Chemical
Like other simple aliphatic amines, ethylamine is a weak base, with a pKa of 10.8.
Ethylamine reacts with acids to form their respective salts.
Reaction with sulfuryl chloride followed by oxidation of the sulfonamide gives diethyldiazene or azoethane (EtN=NEt).[1]
Ethylamine may be oxidized using a strong oxidizer such as potassium permanganate to form acetaldehyde.
Physical
Ethylamine is a colorless gas that condenses just below room temperature to a liquid. It has a strong fish-like odor. Ethylamine is miscible with a variety of solvents, but reacts with acids. Sol. of 70% aq. ethylamine have a density of 0.81 g/mL at 20 °C.
Availability
Ethylamine is sold by chemical suppliers. Since it's classified as List I drug precursor in most countries, it's almost impossible to be acquired by the hobby chemist without a permit. In the United States it is classified as a DEA List I chemical.
Preparation
Ethylamine is produced industrially from the reaction of ethanol and ammonia, in the presence of an oxide catalyst:
- CH3CH2OH + NH3 → CH3CH2NH2 + H2O
In this reaction, ethylamine is coproduced together with diethylamine and triethylamine. Fractional distillation is often used to purify the components.
A simpler route involves reductive amination of acetaldehyde:
- CH3CHO + NH3 + H2 → CH3CH2NH2 + H2O
Other routes involve reacting ethylene and ammonia in the presence of catalyst, such as sodium amide or other related basic catalysts.[2]
- H2C=CH2 + NH3 → CH3CH2NH2
Hydrogenation of acetonitrile, acetamide and nitroethane will also yield ethylamine. These reactions can be effected stoichiometrically using lithium aluminium hydride.
In another route, ethylamine can be synthesized via nucleophilic substitution of a haloethane (such as chloroethane or bromoethane) with ammonia, utilizing a strong base such as potassium hydroxide. Side products, such as diethylamine and triethylamine are also produced.[3]
- CH3CH2Cl + NH3 + KOH → CH3CH2NH2 + KCl + H2O
Projects
- Make ethylammonium salts
- Make simazine
Handling
Safety
Ethylamine is toxic in high concentrations. It's also flammable and mixtures with air in a confined place can be explosive.
Storage
Ethylamine can be stored in compressed cylinders at standard conditions. Alternatively, it may be stored as salt or dissolved in a solvent of choice. Storing it in a fridge or freezer as liquid in a bottle is not recommended.
Disposal
Ethylamine and its salts aren't harmful to the environment and usually don't require special disposal. If you have small amounts, you can dilute the salt and pour it down the drain or in the ground, where it will break down into less harmful products.
References
- ↑ https://web.archive.org/web/20070930230511/http://www.orgsyn.org/orgsyn/pdfs/CV6P0078.pdf
- ↑ https://www.freepatentsonline.com/7161039.pdf
- ↑ http://www.docbrown.info/page06/OrgMechs2b.htm
