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1,5-Hexadiene

From Wikipedia, the free encyclopedia
1,5-Hexadiene
Names
Preferred IUPAC name
Hexa-1,5-diene
Other names
diallyl, biallyl, α,ω-Hexadiene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.008.869Edit this at Wikidata
EC Number
  • 209-754-7
UNII
  • InChI=1S/C6H10/c1-3-5-6-4-2/h3-4H,1-2,5-6H2
    Key: PYGSKMBEVAICCR-UHFFFAOYSA-N
  • C=CCCC=C
Properties
C6H10
Molar mass82.146 g·mol−1
Appearancecolorless liquid
Boiling point59–60 °C (138–140 °F; 332–333 K)
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazard
Danger
H225,H302,H305,H315,H319,H335,H336
P210,P233,P240,P241,P242,P243,P261,P264,P271,P280,P301+P310,P302+P352,P303+P361+P353,P304+P340,P305+P351+P338,P312,P321,P331,P332+P313,P337+P313,P362,P370+P378,P403+P233,P403+P235,P405,P501
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

1,5-Hexadiene is theorganic compound with the formula (CH2)2(CH=CH2)2. It is a colorless, volatile liquid. It is used as acrosslinking agent and precursor to a variety of other compounds.

Synthesis

[edit]

1,5-Hexadiene is produced commercially by theethenolysis of1,5-cyclooctadiene:[1]

(CH2CH=CHCH2)2 + 2 CH2=CH2 → 2 (CH2)2CH=CH2

The catalyst is derived fromRe2O7 on alumina.

A laboratory-scale preparation involves reductive coupling ofallyl chloride using magnesium:[2]

2 ClCH2CH=CH2 + Mg → (CH2CH=CH2)2 + MgCl2

References

[edit]
  1. ^Lionel Delaude; Alfred F. Noels (2005). "Metathesis".Kirk-Othmer Encyclopedia of Chemical Technology. Weinheim: Wiley-VCH.doi:10.1002/0471238961.metanoel.a01.ISBN 9780471484943.
  2. ^Amos Turk; Henry Chanan (1947). "Biallyl".Org. Synth.27: 7.doi:10.15227/orgsyn.027.0007.
Saturated
aliphatic
hydrocarbons
Alkanes
CnH2n + 2
Linear alkanes
Branched alkanes
Cycloalkanes
Alkylcycloalkanes
Bicycloalkanes
Polycycloalkanes
Other
Unsaturated
aliphatic
hydrocarbons
Alkenes
CnH2n
Linear alkenes
Branched alkenes
Alkynes
CnH2n − 2
Linear alkynes
Branched alkynes
Cycloalkenes
Alkylcycloalkenes
Bicycloalkenes
Cycloalkynes
Dienes
Other
Aromatic
hydrocarbons
PAHs
Acenes
Other
Alkylbenzenes
C2-Benzenes
Xylenes
Other
C3-Benzenes
Trimethylbenzenes
Other
C4-Benzenes
Cymenes
Tetramethylbenzenes
Other
Other
Vinylbenzenes
Other
Other
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