:1-Octene

In industry, 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 that 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 alkanes.

There are five commercial processes that oligomerize ethylene to 1-octene. Four of these processes produce 1-octene as a part of a wide distribution of alpha-olefins. In typical circumstances, 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, a South African oil and gas and petrochemical company. For commercial purposes, Sasol 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 hydrocarbons.

Another route to 1-octene involves butadiene telomerization of butadiene. This technology was commercialized by Dow in a facility in Tarragona. 1-Methoxy-

2,7-octadiene is an intermediate in this process.{{cite journal |doi=10.1039/D3IM00009E |title=Industrially applied and relevant transformations of 1,3-butadiene using homogeneous catalysts |date=2023 |last1=Yang |first1=Ji |last2=Wang |first2=Peng |last3=Neumann |first3=Helfried |last4=Jackstell |first4=Ralf |last5=Beller |first5=Matthias |journal=Industrial Chemistry & Materials |volume=1 |issue=2 |pages=155–174 |s2cid=258122761 |doi-access=free }}

Yet another route converts 1-heptene to 1-octene plant based on a Fischer-Tropsch-derived C₇ olefin stream (Sasol, Secunda).

Other 1-octene technologies exist based on selective tetramerisation of ethylene.{{cite journal |last1=Bollmann |first1=Annette |last2=Blann |first2=Kevin |last3=Dixon |first3=John T. |last4=Hess |first4=Fiona M. |last5=Killian |first5=Esna |last6=Maumela |first6=Hulisani |last7=McGuinness |first7=David S. |last8=Morgan |first8=David H. |last9=Neveling |first9=Arno |last10=Otto |first10=Stefanus |last11=Overett |first11=Matthew |last12=Slawin |first12=Alexandra M. Z. |last13=Wasserscheid |first13=Peter |last14=Kuhlmann |first14=Sven |year=2004 |title=Ethylene Tetramerization: A New Route to Produce 1-Octene in Exceptionally High Selectivities |journal=J. Am. Chem. Soc. |volume=126 |issue=45 |pages=14712–14713 |doi=10.1021/ja045602n|pmid=15535683 }}

The main 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 (hydroformylation) to give the C9 aldehyde (nonanal). Oxidation of this aldehyde gives the short-chain fatty acid nonanoic acid. Hydrogenation of the same aldehyde gives the fatty alcohol 1-nonanol, which is used as a plasticizer.

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Category:Alkenes