Cyclohexene

Structural formula
General
Surname	Cyclohexene
other names	1,2,3,4-tetrahydrobenzene
Molecular formula	C 6 H 10
Brief description	colorless liquid with a phenolic odor
External identifiers / databases
EC number	203-807-8
ECHA InfoCard	100.003.462
PubChem	8079
ChemSpider	7788
Wikidata	Q413328
properties
Molar mass	82.15 g · mol -1
Physical state	liquid
density	0.81 g cm −3
Melting point	−104 ° C
boiling point	83 ° C
Vapor pressure	90 h Pa (20 ° C) ; 140 hPa (30 ° C); 225 hPa (40 ° C); 333 hPa (50 ° C);
solubility	practically insoluble in water (0.21 g l −1 at 20 ° C)
Refractive index	1.446 (20 ° C)
safety instructions
H and P phrases	H: 225-302-304-411
	P: 210-262-273
MAK	Switzerland: 300 ml m −3 or 1015 mg m −3
	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

Cyclohexene (1,2,3,4-tetrahydrobenzene) is a colorless liquid with the empirical formula C ₆ H ₁₀ . It belongs to the cycloalkenes (cyclic hydrocarbons with at least one double bond ).

presentation

Starting from cyclohexanol , cyclohexene can be prepared by acid -catalyzed elimination :

It is a 1,2-elimination according to the mechanism of an E1 reaction.

properties

The colorless liquid has a characteristic phenol-like smell, at low concentrations in the ambient air it has a natural gas smell. With a density of 0.81 g · cm ⁻³ , it is lighter than water. The vapors are much heavier than air.

Safety-related parameters

Cyclohexene forms highly flammable vapor-air mixtures. The compound has a flash point of −17 ° C. The explosion range is between 1.09% by volume (37 g / m ³ ) as the lower explosion limit (LEL) and 7.7% by volume as the upper explosion limit (UEL). This results in an upper explosion point of −18 ° C. The limit gap width was determined to be 0.85 mm. This results in an assignment to explosion group IIB. The ignition temperature is 265 ° C. The substance therefore falls into temperature class T3.

use

Cyclohexene is used to synthesize adipic acid and maleic acid , and some derivatives are used to make drugs . Cyclohexene is also a good solvent in the chemical industry and for adhesives .

safety instructions

Cyclohexene is harmful to health. Cyclohexene is slightly hazardous to water (WGK 1).

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s Entry on cyclohexene in the GESTIS substance database of the IFA , accessed on April 24, 2018(JavaScript required) .

↑ Cyclohexene data sheet from Sigma-Aldrich , accessed on November 7, 2016 ( PDF ).

↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 110-83-8 or cyclohexene ), accessed on November 2, 2015.

↑ ^a ^b ^c E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q ^r ^s Entry on cyclohexene in the GESTIS substance database of the IFA , accessed on April 24, 2018(JavaScript required) .