Propionitrile

Structural formula
General
Surname	Propionitrile
other names	Ethyl cyanide; Propionic acid nitrile; Propanoic acid nitrile; Cyanoethane;
Molecular formula	C 3 H 5 N
Brief description	colorless liquid with an ethereal odor
External identifiers / databases
EC number	203-464-4
ECHA InfoCard	100.003.151
PubChem	7854
Wikidata	Q414458
properties
Molar mass	55.08 g mol −1
Physical state	liquid
density	0.78 g cm −3 (at 20 ° C )
Melting point	−103 ° C
boiling point	97 ° C
Vapor pressure	49 h Pa (20 ° C )
solubility	moderate in water (103 g l −1 at 25 ° C )
Refractive index	1.3655 (20 ° C)
safety instructions
H and P phrases	H: 225-300-310-331-319
	P: 210-280-302 + 350-304 + 340-305 + 351 + 338-310-330
Toxicological data	40–56 mg kg −1 ( LD 50 , rabbit , transdermal )
Thermodynamic properties
ΔH f 0	15.5 kJ / mol
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Propionitrile (systematic name propanenitrile ) is a chemical compound from the group of nitriles . The common name is derived from propionic acid .

properties

Propionitrile is a colorless liquid that is readily soluble in water and has a characteristic odor. It is highly flammable and the vapors form explosive mixtures with the air (3.1–14%). At high temperatures, propionitrile decomposes to form hydrocyanic acid and various nitrogen oxides, among other things .

use

Propionitrile is well suited for the further reaction via hydrolysis to propionic acid amide and further to propionic acid, or via reduction to propylamine .

Manufacturing

Propionitrile is usually produced via the Kolbe nitrile synthesis , in which in this case ethane halides (–Cl, –Br, –I) are reacted with alkali metal cyanides in polar, aprotic solvents ( DMSO , acetone ). Since the cyanide used is an ambident nucleophile , the isomeric isonitrile is also formed . The ratio of nitrile to isonitrile depends on the type of reaction and the reaction conditions.

Further synthetic routes to propionitrile can be followed with hydrocyanation and also generally with the catalytic oxidation of hydrocarbons with air in the presence of ammonia . In the case of propionitrile, the latter method initially only leads to acrylonitrile .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on propionitrile in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-440.
↑ Propionitril data sheet (PDF) from Merck , accessed on January 19, 2011.

↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-23.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on propionitrile in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[CRC90_3_440-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-440.

[Merck-3] Propionitril data sheet (PDF) from Merck , accessed on January 19, 2011.

[CRC90_5_23-4] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-23.