1-Octene

December 2023 changed 477208427 1-Octene octene.png 220px 1-Octene 1-Octene-3D-balls.png 220px 1-Octene molecule Oct-1-ene Octene-1, octylene; 1-n-octene; hexylethylene; oct-1-ene; octene; caprylene correct chemspider correct EBI 46708 7833 8125 1/C8H16/c1-3-5-7-8-6-4-2/h3H,1,4-8H2,2H3 KWKAKUADMBZCLK-UHFFFAOYAN correct chemspider 1S/C8H16/c1-3-5-7-8-6-4-2/h3H,1,4-8H2,2H3 correct chemspider KWKAKUADMBZCLK-UHFFFAOYSA-N correct CAS 111-66-0 correct FDA E5VK21B9RC C=CCCCCCC C8H16 112.24 g/mol 0.715 g/cm3 -101.7 https://webbook.nist.gov/cgi/cbook.cgi?ID=C111660&Units=SI&Mask=1EFF 1-Octene 121 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. 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.10.1039/D3IM00009E Industrially applied and relevant transformations of 1,3-butadiene using homogeneous catalysts 2023 Yang Ji Wang Peng Neumann Helfried Jackstell Ralf Beller Matthias Industrial Chemistry & Materials 1 2 155–174 258122761 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.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 10.1021/ja045602n 15535683 2004JAChS.12614712B 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 Category:Alkenes