1-Hexene

1-Hexene
General
Chemical name	Hex-1-ene
Chemical formula	C6H12
SMILES	C=CCCCC
Molecular mass	84.1608 g/mol
CAS number	[592-41-6]
DOT #:	UN 2370
Properties
State at STP	Liquid
Water solubility	insoluble
Density	0.673 g/cm³
Melting point	-139.8 °C
Boiling point	63 °C
Flashpoint	-26 °C
vapor density	3
vapor pressure	2.6 PSIA
Critical temperature	447.40 °F
Critical pressure	458 psi
Critical density	0.241 g/ml
Refractive index	1.3879
Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references

1-Hexene
1-Hexene
General
Systematic name	?
Other names	?
Molecular formula	?
SMILES	?
Molar mass	?.?? g/mol
Appearance	?
CAS number	[?-?-?]
Properties
Density and phase	? g/cm³, ?
Solubility in water	? g/100 ml (?°C)
Melting point	?°C (? K)
Boiling point	?°C (? K)
Acidity (pKa)	?
Basicity (pKb)	?
Chiral rotation [α]D	?°
Viscosity	? cP at ?°C
Structure
Molecular shape	?
Coordination geometry	?
Crystal structure	?
Dipole moment	? D
Hazards
MSDS	External MSDS
Main hazards	?
NFPA 704
Flash point	?°C
R/S statement	R: ? S: ?
RTECS number	?
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Related compounds
Other anions	?
Other cations	?
Related ?	?
Related compounds	?
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

1-hexene is a higher olefin, or alkene, with a formula C₆H₁₂. 1-hexene is an alpha-olefin, meaning that the double bond is located at the alpha (primary) position, endowing the compound with higher reactivity and thus useful chemical properties. 1-hexene is an industrially significant linear alpha olefin.

Synthesis

Industrially, 1-hexene is commonly manufactured by two main routes: oligomerization of ethene and by Fischer-Tropsch synthesis followed by purification. Another route to 1-hexene, used commercially on small scale, is dehydration of alcohols. Prior to the 1970's 1-hexene was also manufactured by the thermal cracking of waxes. Linear internal hexenes were manufactured by chlorination/dehydrochlorination of linear paraffins.

There are five commercial processes which oligomerize ethene to 1-hexene. Four of these processes produce 1-hexene as a part of a wide distribution of alpha-olefins. Typically, 1-hexene content ranges from about twenty percent distribution in the Ethyl (Innovene) process, whereas only twelve percent of distribution in the Gulf (CP Chemicals) and Idemitsu processes.

The only commercial process to isolate 1-hexene from a wide mixture of C₆ hydrocarbons is practiced by Sasol Ltd., a South African oil and gas and petrochemical company. Sasol commercially employs Fischer-Tropsch synthesis to make fuels from synthesis gas derived from coal. The synthesis recovers 1-hexene from the afformentioned fuel streams, where the initial 1-hexene concentration cut may be 60% in a narrow distillation, with the remainder being vinylidenes, linear and branched internal olefins, linear and branched paraffins, alcohols, aldehydes, carboxylic acids and aromatic compounds.

Synthesis of 1-hexene as a part of multi-product ethene oligomerization process or a Fischer-Tropsch process is covered in an article on Linear alpha olefins.

One process, the Phillips ethene trimerization process, produces only 1-hexene.

Applications

The primary use of 1-hexene is as a comonomer in production of polyethene. High density polyethene (HDPE) and linear low density polyethene (LLDPE) use approximately 2-4% and 8-10% of comonomers.

Another significant use of 1-hexene is the production of linear aldehyde via hydroformylation ( oxo synthesis ) for later production of the short-chain fatty acid heptanoic acid.

Synonyms

• Hex-1-ene
• Hexene-1
• Hexene
• Hexylene
• 1-n-hexene
• Nutylethene
• C6