5-hexenonitrilo - 5-hexenonitrilo

5-hexenonitrilo
5-hexenonitrilo.tif
5-hexenonitrilo-3D.gif
IUPAC name
hex-5-enonitrilo
General
Other names 5-cyano-1-pentene
4-pentenyl cyanide
Semi-developed formula CH2=CH-(CH2)3-C≡N
Molecular formula C 6 H 9 N
Identifiers
CAS number 5048-19-1[1]
ChemSpider 109837
PubChem 123222
Physical properties
Appearance Liquid colorless or pale yellow
Density 837 kg/; 0,837 g/cm³
Molar mass 95.15 g / mol
Melting point −64 °C (209 K)
Boiling point 162 °C (435 K)
Vapor pressure 2,5 mmHg
Refractive index (n D ) 1,426
Chemical properties
Solubility in water 2,3 g/L
log P 1,29
Family Nitrilo
Dangerousness
Flash point 313,15 K (40 °C)
Related compounds
nitrilos hexanonitrile
5-hexynonitrile
dinitrilos adiponitrilo
b-hidromucononitrilo
Values ​​in the SI and under standard conditions
(25 and 1 atm ), unless otherwise indicated.

The 5-hexenenitrile , also called 5-cyano-1-pentene and 4-pentenyl cyanide , [ 2 ] [ 3 ] [ 4 ] is a nitrile whose molecular formula is C 6 H 9 N . Its structure is similar to that of hexanonitrile but, unlike it, it has a double bond between carbons 5 and 6.

Physical and chemical properties

A room temperature , 5-hexenenitrile is a liquid colorless or pale yellow with a characteristic odor. [ 5 ] [ 4 ] Its density is lower than that of the water (ρ = 0.837 g / cm³ ). It has its boiling point at 162 ° C and its melting point - theoretical and non-experimental value - at -64 ° C. It is very soluble in water, only 2 g / L . The value of the logarithm of yourpartition coefficient , log P = 1.29, indicates that is more soluble in solvents apolar in solvents polar . [ 6 ] [ 2 ]

Regarding its reactivity , 5-hexenonitrile is incompatible with oxidizing agents . [ 5 ]

Synthesis and uses

5-hexenonitrile can be synthesized by reacting 5-bromo-1-pentene with potassium cyanide in ethylene glycol at 100 ° C; the final product, after being cooled and diluted with water, is extracted into ethyl ether . The yield of this procedure reaches 82%. [ 7 ] Likewise, the reaction between allyl bromide and acrylonitrile , using [CpFe (CO) 2 ] 2 as a mediator , is another way of making 5-hexenonitrile. [ 8 ] The Beckmann rearrangement of cyclohexanone oximea ε-caprolactam , carried out in the vapor phase by means of a pulse reactor unit coupled to a gas chromatograph , also produces 5-hexenonitrile; AlPO 4 –γAl 2 O 3 can be used as a catalyst . [ 9 ] Finally, the fragmentation of the tin compound 3- (tributylstannyl) cyclohexanone oxime is another alternative for the synthesis of 5-hexenonitrile. [ 10 ]

Regarding its uses, the use of 5-hexenonitrile has been proposed for the «functionalization» of polymers , a chemical process by which reactive functional groups are incorporated into a polymer chain; such polymers reduce hysteresis of rubber vulcanizates used in tire manufacturing. [ 11 ]

In nature, this nitrile has been identified in Degenia velebitica , an endemic European plant of the genus Brassica . [ 12 ]

Precautions

This compound is a combustible product that has its flash point at 40ºC. When burning it may emit harmful gases such as nitrogen oxides , carbon monoxide and hydrogen cyanide . It is a toxic product if ingested or inhaled and its contact causes irritation to the skin and eyes. [ 5 ]

See also

The following nitriles are isomers of 5-hexenonitrile:

References