1-Octene: Difference between revisions
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==Synthesis== |
==Synthesis== |
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In industry, 1-octene is commonly manufactured by two main routes: [[oligomerization]] of [[ethylene]] and by [[Fischer–Tropsch process|Fischer–Tropsch synthesis]] followed by purification. Another route to 1-octene that has been used commercially on a small scale is [[Dehydration reaction|dehydration]] of [[alcohol]]s. Prior to the 1970s, 1-octene was also manufactured by thermal cracking of [[wax]]es, whereas linear internal [[octene]]s were also manufactured by [[halogenation|chlorination]]/[[dehydrochlorination]] of [[linear alkane]]s. |
In industry, 1-octene is commonly manufactured by two main routes: [[oligomerization]] of [[ethylene]] and by [[Fischer–Tropsch process|Fischer–Tropsch synthesis]] followed by purification. Another route to 1-octene that has been used commercially on a small scale is [[Dehydration reaction|dehydration]] of [[Alcohol (chemistry)|alcohol]]s. Prior to the 1970s, 1-octene was also manufactured by thermal cracking of [[wax]]es, whereas linear internal [[octene]]s were also manufactured by [[halogenation|chlorination]]/[[dehydrochlorination]] of [[linear alkane]]s. |
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There are five commercial processes that [[oligomerization|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|1-hexene]] content of the entire distribution of alpha-olefins ranges from about 25% of the distribution in the [[Ethyl Corporation|Ethyl]] ([[Innovene]]) process to about 8% of distribution in some modes of the [[Gulf Oil|Gulf]] (CP Chemicals) and [[Idemitsu]] processes. |
There are five commercial processes that [[oligomerization|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|1-hexene]] content of the entire distribution of alpha-olefins ranges from about 25% of the distribution in the [[Ethyl Corporation|Ethyl]] ([[Innovene]]) process to about 8% of distribution in some modes of the [[Gulf Oil|Gulf]] (CP Chemicals) and [[Idemitsu]] processes. |
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The only commercial process to isolate 1-octene from a wide mixture of C<sub>8</sub> hydrocarbons is practiced by [[Sasol]], a [[South Africa]]n oil and gas and petrochemical company. For commercial purposes, Sasol employs [[Fischer–Tropsch process|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, [[alcohol]]s, [[aldehyde]]s, [[carboxylic acid]]s, and [[aromatic hydrocarbon]]s. |
The only commercial process to isolate 1-octene from a wide mixture of C<sub>8</sub> hydrocarbons is practiced by [[Sasol]], a [[South Africa]]n oil and gas and petrochemical company. For commercial purposes, Sasol employs [[Fischer–Tropsch process|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, [[Alcohol (chemistry)|alcohol]]s, [[aldehyde]]s, [[carboxylic acid]]s, and [[aromatic hydrocarbon]]s. |
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In recent years, two on-purpose 1-octene technologies have been commercialised: a butadiene [[telomerization]] plant (Dow, Tarragona), and a 1-heptene to 1-octene plant based on a Fischer-Tropsch-derived C<sub>7</sub> olefin stream (Sasol, Secunda). Sasol is currently in the engineering phase of a new 1-octene technology based on selective tetramerisation of ethylene.<ref>{{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 }}</ref> |
In recent years, two on-purpose 1-octene technologies have been commercialised: a butadiene [[telomerization]] plant (Dow, Tarragona), and a 1-heptene to 1-octene plant based on a Fischer-Tropsch-derived C<sub>7</sub> olefin stream (Sasol, Secunda). Sasol is currently in the engineering phase of a new 1-octene technology based on selective tetramerisation of ethylene.<ref>{{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 }}</ref> |
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Revision as of 11:08, 6 January 2022
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| Names | |
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| Preferred IUPAC name
Oct-1-ene | |
| Other names
Octene-1, octylene; 1-n-octene; hexylethylene; oct-1-ene; octene
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.003.540 |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C8H16 | |
| Molar mass | 112.24 g/mol |
| Density | 0.715 g/cm3 |
| Melting point | −101.7 °C (−151.1 °F; 171.5 K)[1] |
| Boiling point | 121 °C (250 °F; 394 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1-Octene is an organic compound with a formula CH2CHC6H13. The alkene is classified as a higher olefin and 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 important linear alpha olefins in industry. It is a colourless liquid.
Synthesis
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.
In recent years, two on-purpose 1-octene technologies have been commercialised: a butadiene telomerization plant (Dow, Tarragona), and a 1-heptene to 1-octene plant based on a Fischer-Tropsch-derived C7 olefin stream (Sasol, Secunda). Sasol is currently in the engineering phase of a new 1-octene technology based on selective tetramerisation of ethylene.[2]
Applications
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.
References
- ^ a b "1-Octene".
- ^ Bollmann, Annette; Blann, Kevin; Dixon, John T.; Hess, Fiona M.; Killian, Esna; Maumela, Hulisani; McGuinness, David S.; Morgan, David H.; Neveling, Arno; Otto, Stefanus; Overett, Matthew; Slawin, Alexandra M. Z.; Wasserscheid, Peter; Kuhlmann, Sven (2004). "Ethylene Tetramerization: A New Route to Produce 1-Octene in Exceptionally High Selectivities". J. Am. Chem. Soc. 126 (45): 14712–14713. doi:10.1021/ja045602n. PMID 15535683.