8-chloro-1-octene - 8-cloro-1-octeno

8-chloro-1-octene
8-cloro-1-octeno.tif
8-cloro-1-octeno-3D.gif
IUPAC name
8-chlorooct-1-eno
General
Other names 7-octenyl chloride
Semi-developed formula Cl CH 2 - (CH 2 ) 5 -CH = CH 2
Molecular formula C8H15Cl
Identifiers
CAS number 871-90-9[1]
ChemSpider 9519035
PubChem 11344097
Physical properties
Appearance liquid colorless
Density 916 kg/; 0,916 g/cm³
Molar mass 146.66 g / mol
Melting point −38 °C (235 K)
Boiling point 181 °C (454 K)
Vapor pressure 1,2 ± 0,3 mmHg
Refractive index (n D ) 1,435
Chemical properties
Solubility in water 14 mg / L
log P 4,24
Family Haloalkene
Dangerousness
Flash point 332 K (59 °C)
Related compounds
chloroalkenes 6-cloro-1-hexeno
10-cloro-1-deceno
cloroalcanos 1-clorooctano
dichloroalkanes 1,8-dichlorooctane
Values ​​in the SI and under standard conditions
(25 and 1 atm ), unless otherwise indicated.

The 8-chloro-1-octene , also called 8-clorooct-1-ene or chloride 7-octenyl , is an organic compound of formula molecular C 8 H 15 Cl . It is a haloalkane linear eight carbons with one atom of chlorine bonded to one of the terminal carbons and one double bond at the opposite end of the carbon chain . [ 2 ] [ 3 ] [ 4 ]

Physical and chemical properties

At room temperature , 8-chloro-1-octene is a colorless liquid with a density lower than that of water, ρ = 0.916 g / cm³ . It has its boiling point at 181 ° C and its melting point at -38 ° C, these values ​​being estimated. The value of the logarithm of the partition coefficient , log P = 4.24, it indicates that it is much more soluble in solvents apolar than in polar solvents. [ 3 ] Thus, it is soluble in the usual organic solvents such asbenzene or alkanes but is essentially insoluble in water. [ 5 ]

Synthesis

8-Chloro-1-octene is prepared starting from 8-bromo-1-octene , which, unlike 8-chloro-1-octene, can be obtained from 1,7-octadiene . Subsequent heating of 8-bromo-1-octene in the presence of a quaternary ammonium chloride or lithium chloride and a miscible aqueous alkaline medium leads to the formation of 8-chloro-1-octene. The yields obtained are between 10% and 100%: for example, using tetramethylammonium chloride in ethanol , the yield reaches 92%. [ 5 ]

8-Chloro-1-octene can also be synthesized starting from lithium tris (5-chloropentyl) (methyl) borate in tetrahydrofuran and allyl chloride , in the presence of copper (I) bromide at 0 ° C. The yield in this case is 91%. [ 6 ]

Finally, the reaction between 1-bromo-5-chloropentane and allyl (bromo) magnesium in the presence of lithium tetrachlorocuprate allows to obtain 8-chloro-1-octene with a yield of 83%. [ 7 ]

Applications

8-chloro-1-octene comonomer is useful as an additive in the production of polymers of Ziegler type of hydrocarbons solid high molecular weight , such as polyethylene , polypropylene or poly-4-methyl-1-pentene . The incorporation of a relatively small amount of this compound to the polymer does not modify its physical characteristics, but makes it suitable for dyeing or vulcanization . [ 5 ] In this sense, 8-chloro-1-octene has been used in the preparation of polymers modified with aromatic groups. [ 8 ]It can also be used as a halogenated alkene in the manufacture of heat resistant polylactic acid continuous extrusion foam . [ 9 ]

Another use of this chloroalkene is in the production of silane compounds that contain a mercapto group . [ 10 ]

References