5-hexenonitrilo - 5-hexenonitrilo
|Molecular formula||C 6 H 9 N|
|Appearance||Liquid colorless or pale yellow|
|Density||837 kg/m³; 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|
|Solubility in water||2,3 g/L|
|Flash point||313,15 K (40 °C)|
|nitrilos|| hexanonitrile |
|dinitrilos|| adiponitrilo |
|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 ]
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 ]
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 ]
The following nitriles are isomers of 5-hexenonitrile:
- CAS number
- 5-Hexenenitrile (ChemSpider)
- 5-Hexenenitrile (PubChem)
- 5-Hexenenitrile (Chemical Book)
- 5-hexenenitrile. MSDS (AlfaAesar)
- 5-Hexenenitrile (EPA)
- Indane-2-mercaptoacetylamide disulfide derivatives useful as inhibitors of enkephalinase (1997). Gary A. Flynn, Douglas W. Beight, Alan M. Warshawsky, Shujaath Mehdi, John H. Kehne. Patente US5604221 A
- Thoma, G.; Giese, B. (1989). «Generation and synthetic use of alkyl radicals with [CpFe(CO)2]2 as mediator». Tetrahedron Letters 30 (22): 2907-2910. Consultado el 23 de marzo de 2017.
- Costa, A.; Deya, P.M.; Sinisterra, J.V.; Marinas, J.M. (1980). «Vapor phase Beckmann rearrangement of the cyclohexanone oxime catalyzed by AlPO4–γAl2O3 Systems». Canadian Journal of Chemistry 58 (12): 1266-1270. Consultado el 23 de marzo de 2017.
- Bakale, Roger P.; Scialdone, Mark A.; Johnson, Carl R. (1990). «Tin-directed Baeyer-Villiger and Beckmann fragmentations». J. Chem. Am. Soc. 112 (18): 6729-6731. Consultado el 23 de marzo de 2017.
- POLYMERS FUNCTIONALIZED WITH NITRILE COMPOUNDS CONTAINING A PROTECTED AMINO GROUP (2015). Luo, Steven; et al. Patente US 20150148489
- Mastelić, J.; Blažević, I.; Kosalec, I. (2010). «Chemical composition and antimicrobial activity of volatiles from Degenia velebitica, a European stenoendemic plant of the Brassicaceae family». Chem. Biodivers. 7 (11): 2755-2765. Consultado el 23 de marzo de 2017.