1,5-hexadiene

Structural formula
General
Surname	1,5-hexadiene
other names	Hexa-1,5-diene; Diallyl;
Molecular formula	C 6 H 10
Brief description	colorless liquid
External identifiers / databases
EC number	209-754-7
ECHA InfoCard	100,008,869
PubChem	11598
ChemSpider	11110
Wikidata	Q161551
properties
Molar mass	82.15 g mol −1
Physical state	liquid
density	0.69 g cm −3
Melting point	−141 ° C
boiling point	60 ° C
Vapor pressure	223 h Pa (20 ° C)
solubility	very heavy in water (170 mg / l at 25 ° C)
Refractive index	1.404
safety instructions
H and P phrases	H: 225-304-315-319-335
	P: 261-302 + 352-280-305 + 351 + 338-210
	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

1,5-hexadiene is an organic chemical compound with the empirical formula C ₆ H ₁₀ . It belongs to the group of dienes .

Extraction and presentation

1,5-Hexadiene can be produced from the gas phase reaction between propene and 3-bromopropene . Another possibility is the oxidative gas phase reaction between two molecules of propene with hydrogen peroxide .

{\ displaystyle \ mathrm {2 \ H_ {2} C {=} CH {-} CH_ {3} \ {\ xrightarrow [{H_ {2} O_ {2}}] {630 ^ {\ circ} C}} \ \ C_ {6} H_ {10}}}

properties

It is a colorless liquid that solidifies at −141 ° C and boils at 60 ° C. The flash point is −46 ° C. In the range of 2 to 6.1 percent by volume of the gas in air, explosive mixtures form.

use

1,5-Hexadiene can be used to synthesize other hexane derivatives . This includes, for example, the synthesis of 1,6-hexanediol , which can be produced from 1,5-hexadiene by hydroboration .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 1,5-hexadiene in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ Data sheet 1,5-hexadiene from Sigma-Aldrich , accessed on February 27, 2010 ( PDF ). .
↑ Patent Shell Devel US 2,755,322 1952 .
↑ ER Bell, WE Vaughan, FF Rust: Hydrogen Peroxide-Olefin Reactions in the Vapor Phase , in: J. Am. Chem. Soc. , 1957 , 79 (15) , pp. 3997-4000; doi : 10.1021 / ja01572a011 .
↑ Data sheet 1,5-hexadiene (PDF) from Merck , accessed on February 27, 2010.
^ HC Brown, G. Zweifel: The Hydroboration of Dienes , in: J. Am. Chem. Soc. , 1959 , 81 (21) , pp. 5832-5833; doi : 10.1021 / ja01530a071 .

[gestis-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on 1,5-hexadiene in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[sigma-2] Data sheet 1,5-hexadiene from Sigma-Aldrich , accessed on February 27, 2010 ( PDF ). .

[3] Patent Shell Devel US 2,755,322 1952 .

[4] ER Bell, WE Vaughan, FF Rust: Hydrogen Peroxide-Olefin Reactions in the Vapor Phase , in: J. Am. Chem. Soc. , 1957 , 79 (15) , pp. 3997-4000; doi : 10.1021 / ja01572a011 .

[merck-5] Data sheet 1,5-hexadiene (PDF) from Merck , accessed on February 27, 2010.

[6] HC Brown, G. Zweifel: The Hydroboration of Dienes , in: J. Am. Chem. Soc. , 1959 , 81 (21) , pp. 5832-5833; doi : 10.1021 / ja01530a071 .