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1-Octene



1-Octene
IUPAC name Oct-1-ene
Other names Octene-1, octylene; 1-n-ctene; hexylethylene; oct-1-ene; octene
Identifiers
CAS number 111-66-0
SMILES C=CCCCCCC
Properties
Molecular formula C8H16
Molar mass 112.24 g/mol
Density 0.715 g/cm³
Melting point

-101.7 °C

Boiling point

121 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

1-Octene is a higher olefin, or alkene, with a formula C8H16. 1-Octene is an alpha-olefin, meaning that the double bond is located at the alpha (primary) position, endowing this compound with higher reactivity and thus useful chemical properties. 1-Octene is one of the industrially important linear alpha olefins.

Additional recommended knowledge

Synthesis

Industrially, 1-octene is commonly manufactured by two main routes: oligomerization of ethylene and by Fischer-Tropsch synthesis followed by purification. Another route to 1-octene which has been used commercially on a small scale is dehydration of alcohols. Prior to the 1970s 1-octene was also manufactured by thermal cracking of waxes, whereas linear internal octenes were also manufactured by chlorination/dehydrochlorination of linear paraffins.

There are five commercial processes which oligomerize ethylene to 1-octene. Four of these processes produce 1-octene as a part of a wide distribution of alpha-olefins. Typically, 1-hexene content of the entire distribution of alpha-olefins ranges from about 25% of the distribution in the Ethyl (Innovene) process to about 8% of distribution in some modes of the Gulf (CP Chemicals) and Idemitsu processes.

The only commercial process to isolate 1-octene from a wide mixture of C8 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 and recovers 1-octene from these fuel streams, where the initial 1-octene concentration in a narrow distillation cut may be 60%, with the remainder being vinylidenes, linear and branched internal olefins, linear and branched paraffins, alcohols, aldehydes, carboxylic acids and aromatic compounds.

Synthesis of 1-octene as a part of multi-product ethylene oligomerization process or a Fischer-Tropsch process is covered in an article on linear alpha olefins.

Although several processes have been proposed in patents or in technical literature, there is not a viable commercial process which produces only 1-octene.

Applications

The primary, even overwhelming, use of 1-octene is as a comonomer in production of polyethylene. High density polyethylene (HDPE) and linear low density polyethylene (LLDPE) use approximately 2-4% and 8-10% of comonomers, respectively.

Another significant use of 1-octene is for production of linear aldehyde via OXO Synthesis (hydroformulation) for later production of the short-chain fatty acid nonanoic acid, a carboxylic acid, by oxidation of an intermediate aldehyde or linear alcohols for plasticizer application by hydrogenation of the aldehyde.

References

     
    This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "1-Octene". A list of authors is available in Wikipedia.
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