Production of Linear Octenes from Oligomerization of 1-Butene over Carbon-Supported Cobalt Catalysts

Xu, Zhuoran; Chada, Joseph P.; Zhao, Dongting; Carrero, Carlos A.; Kim, Yong Tae; Rosenfeld, Devon C.; Rogers, Jessica L.; Rozeveld, Steven J.; Hermans, Ive; Huber, George W.

doi:10.1021/acscatal.6b00655

Production of Linear Octenes from Oligomerization of 1-Butene over Carbon-Supported Cobalt Catalysts

Journal Article · Wed May 04 00:00:00 EDT 2016 · ACS Catalysis

DOI:https://doi.org/10.1021/acscatal.6b00655· OSTI ID:1257483

Xu, Zhuoran ^[1]; Chada, Joseph P. ^[1]; Zhao, Dongting ^[1]; Carrero, Carlos A. ^[1]; Kim, Yong Tae ^[1]; Rosenfeld, Devon C. ^[2]; Rogers, Jessica L. ^[2]; Rozeveld, Steven J. ^[2]; Hermans, Ive ^[1]; Huber, George W. ^[1]

Univ. of Wisconsin, Madison, WI (United States)
The Dow Chemical Company, Freeport, TX (United States)

Here, linear octenes were produced in high (70–85%) selectivity from oligomerization of liquid 1-butene using carbon-supported cobalt oxide catalysts in a continuous flow reactor. The liquid products were characterized by two-dimensional gas chromatography–mass spectrometry. Above 95% of the oligomers were C8 olefins, with the other products primarily being branched C12 olefins. The linear octene products at a conversion of 9.77% decreased in selectivity according to 3-octene > trans-2-octene > cis-2-octene > 4-octene. Methyl-heptenes including trans/cis-5-methyl-2-heptene > trans/cis-5-methyl-3-heptene > trans-3-methyl-2-heptene (at the lowest conversion) were the other major products summing to 15.6%. The selectivity of linear octenes decreased from 84 to 78% as the conversion increased from 10% to 29%. The product distribution suggests the reaction pathway involves a head-to-head coupling of two 1-butene molecules to form internal linear octenes. Head-to-tail coupling of two 1-butene molecules or a coupling between 1-butene and 2-butene forms the observed methyl-heptenes. The rate of head-to-head coupling is higher than the rate of head-to-tail or the rate of 1-butene to 2-butene coupling as indicated by the higher selectivity of linear octenes. The activated catalyst contained both Co₃O₄ and CoO as confirmed by X-ray diffraction (XRD), in situ Raman spectroscopy, and X-ray absorption spectroscopy. The cobalt oxide particle size was estimated to be between 5 and 10 nm by high-resolution transmission electron microscopy and XRD. The Co₃O₄/CoO ratio decreased with increasing pretreatment temperature. Metallic cobalt, which has a low catalytic activity, formed at 550 °C.

View Accepted Manuscript (DOE)

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: The Dow Chemical Company

OSTI ID:: 1257483

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 6 Vol. 6; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: ENGLISH

References (32)

Oligomerization of Ethylene to α-Olefins: Discovery and Development of the Shell Higher Olefin Process (SHOP) Keim, Wilhelm Angewandte Chemie International Edition, Vol. 52, Issue 48 https://doi.org/10.1002/anie.201305308	journal	October 2013
Design of a Cobalt-Zeolite Catalyst for Semi-Linear Higher-Olefin Synthesis Franken, Joris; Kirschhock, Christine E. A.; Mathys, Georges M. ChemCatChem, Vol. 4, Issue 9 https://doi.org/10.1002/cctc.201200267	journal	July 2012
Comparative Dimerization of 1-Butene with a Variety of Metal Catalysts, and the Investigation of a New Catalyst for CH Bond Activation Small, Brooke L.; Schmidt, Roland Chemistry - A European Journal, Vol. 10, Issue 4 https://doi.org/10.1002/chem.200304945	journal	February 2004
Co/CNF Catalysts Tailored by Controlling the Deposition of Metal Colloids onto CNFs: Preparation and Catalytic Properties Qiu, Jieshan; Zhang, Hongzhe; Liang, Changhai Chemistry - A European Journal, Vol. 12, Issue 8 https://doi.org/10.1002/chem.200500960	journal	March 2006
Olefin oligomerization via zeolite catalysis Knifton, John F.; Sanderson, John R.; Dai, P. Eugene Catalysis Letters, Vol. 28, Issue 2-4 https://doi.org/10.1007/BF00806051	journal	January 1994
Olefin dimerization over cobalt-oxide-on-carbon catalysts I. Propylene dimerization Schultz, R. Journal of Catalysis, Vol. 6, Issue 3 https://doi.org/10.1016/0021-9517(66)90164-3	journal	December 1966
Olefin dimerization over cobalt-oxide-on-carbon catalysts II. Butene and hexene dimerization Schultz, R. Journal of Catalysis, Vol. 6, Issue 3 https://doi.org/10.1016/0021-9517(66)90167-9	journal	December 1966
Nickel-based heterogeneous catalysts for olefin oligomerization Chauvin, Y.; Commereuc, D.; Hugues, F. Applied Catalysis, Vol. 42, Issue 2 https://doi.org/10.1016/0166-9834(88)80002-2	journal	September 1988
Dimerization of 1-butene over nickel zeolitic catalysts: A search for linear dimers Beltrame, Paolo; Forni, Lucio; Talamini, Antonello Applied Catalysis A: General, Vol. 110, Issue 1 https://doi.org/10.1016/0926-860X(94)80103-7	journal	March 1994
Aqueous-phase reforming of methanol and ethylene glycol over alumina-supported platinum catalysts Shabaker, J. Journal of Catalysis, Vol. 215, Issue 2 https://doi.org/10.1016/S0021-9517(03)00032-0	journal	April 2003
Characterization of metal nitrates and clay supported metal nitrates by thermal analysis Cseri, T.; Békássy, S.; Kenessey, G. Thermochimica Acta, Vol. 288, Issue 1-2 https://doi.org/10.1016/S0040-6031(96)03037-7	journal	October 1996
Ziegler-Natta Catalysis Sinn, Hansjörg; Kaminsky, Walter Advances in Organometallic Chemistry, Vol. 18, p. 99-149 https://doi.org/10.1016/S0065-3055(08)60307-X	book	January 1980
Ethene oligomerization on Ni-SiO2-Al2O3: Experimental investigation and Single-Event MicroKinetic modeling Toch, K.; Thybaut, J. W.; Marin, G. B. Applied Catalysis A: General, Vol. 489 https://doi.org/10.1016/j.apcata.2014.10.036	journal	January 2015
Carbon nanofiber supported Ni catalysts for the hydrogenation of chloronitrobenzenes Wang, Chuang; Qiu, Jieshan; Liang, Changhai Catalysis Communications, Vol. 9, Issue 8 https://doi.org/10.1016/j.catcom.2008.02.003	journal	April 2008
Selective ethylene oligomerization: Recent advances in chromium catalysis and mechanistic investigations Agapie, Theodor Coordination Chemistry Reviews, Vol. 255, Issue 7-8 https://doi.org/10.1016/j.ccr.2010.11.035	journal	April 2011
Solid phosphoric acid catalyst for propene oligomerization: Effect of silicon phosphate composition Zhang, Jichang; Yan, Yaru; Chu, Qi Fuel Processing Technology, Vol. 135 https://doi.org/10.1016/j.fuproc.2014.09.007	journal	July 2015
A new approach to high performance Co/C catalysts for selective hydrogenation of chloronitrobenzenes Xing, L.; Qiu, J.; Liang, C. Journal of Catalysis, Vol. 250, Issue 2 https://doi.org/10.1016/j.jcat.2007.06.008	journal	September 2007
Low-temperature oligomerization of 1-butene with H-ferrierite Kim, Yong Tae; Chada, Joseph P.; Xu, Zhuoran Journal of Catalysis, Vol. 323 https://doi.org/10.1016/j.jcat.2014.12.025	journal	March 2015
Stabilizing cobalt catalysts for aqueous-phase reactions by strong metal-support interaction Lee, Jechan; Burt, Samuel P.; Carrero, Carlos A. Journal of Catalysis, Vol. 330 https://doi.org/10.1016/j.jcat.2015.07.003	journal	October 2015
Characterization of cobalt oxides studied by FT-IR, Raman, TPR and TG-MS Tang, Chih-Wei; Wang, Chen-Bin; Chien, Shu-Hua Thermochimica Acta, Vol. 473, Issue 1-2, p. 68-73 https://doi.org/10.1016/j.tca.2008.04.015	journal	July 2008
Chemistry of olefin oligomerization over ZSM-5 catalyst Quann, Richard J.; Green, Larry A.; Tabak, Samuel A. Industrial & Engineering Chemistry Research, Vol. 27, Issue 4 https://doi.org/10.1021/ie00076a006	journal	April 1988
Ethylene Tetramerization: A New Route to Produce 1-Octene in Exceptionally High Selectivities Bollmann, Annette; Blann, Kevin; Dixon, John T. Journal of the American Chemical Society, Vol. 126, Issue 45 https://doi.org/10.1021/ja045602n	journal	November 2004
Cobalt-Catalyzed Dimerization of α-Olefins to Give Linear α-Olefin Products Broene, Richard D.; Brookhart, Maurice; Lamanna, William M. Journal of the American Chemical Society, Vol. 127, Issue 49 https://doi.org/10.1021/ja056655n	journal	December 2005
Iron-Based Catalysts with Exceptionally High Activities and Selectivities for Oligomerization of Ethylene to Linear α-Olefins Small, Brooke L.; Brookhart, Maurice Journal of the American Chemical Society, Vol. 120, Issue 28 https://doi.org/10.1021/ja981317q	journal	July 1998
Thermal Studies of Nickel, Cobalt, Iron and Copper Oxides and Nitrates. Keely, W. M.; Maynor, Harry W. Journal of Chemical & Engineering Data, Vol. 8, Issue 3 https://doi.org/10.1021/je60018a008	journal	July 1963
1-Butene Oligomerization in Brönsted Acidic Zeolites: Mechanistic Insights from Low-Temperature in Situ FTIR Spectroscopy Bjørgen, Morten; Lillerud, Karl-Petter; Olsbye, Unni The Journal of Physical Chemistry B, Vol. 108, Issue 23 https://doi.org/10.1021/jp0377836	journal	June 2004
Selective Dimerization/Oligomerization of α-Olefins by Cobalt Bis(imino)pyridine Catalysts Stabilized by Trifluoromethyl Substituents: Group 9 Metal Catalysts with Productivities Matching Those of Iron Systems Tellmann, Kilian P.; Gibson, Vernon C.; White, Andrew J. P. Organometallics, Vol. 24, Issue 2 https://doi.org/10.1021/om049297q	journal	January 2005
Iron(II) and Cobalt(II) 2-(Benzimidazolyl)-6-(1-(arylimino)ethyl)pyridyl Complexes as Catalysts for Ethylene Oligomerization and Polymerization Sun, Wen-Hua; Hao, Peng; Zhang, Shu Organometallics, Vol. 26, Issue 10 https://doi.org/10.1021/om0700819	journal	May 2007
Magnetically recoverable Ni/C catalysts with hierarchical structure and high-stability for selective hydrogenation of nitroarenes Zhang, Peng; Yu, Chang; Fan, Xiaoming Physical Chemistry Chemical Physics, Vol. 17, Issue 1 https://doi.org/10.1039/C4CP03978E	journal	January 2015
Anomalous reactivity of supported V2O5 nanoparticles for propane oxidative dehydrogenation: influence of the vanadium oxide precursor Carrero, Carlos A.; Keturakis, Christopher J.; Orrego, Andres Dalton Transactions, Vol. 42, Issue 35 https://doi.org/10.1039/c3dt50611h	journal	January 2013
Standard Chemical Thermodynamic Properties of Alkene Isomer Groups Alberty, Robert A.; Gehrig, Catherine A. Journal of Physical and Chemical Reference Data, Vol. 14, Issue 3 https://doi.org/10.1063/1.555737	journal	July 1985
Direct Fabrication of Cobalt Oxide Nanoparticles Employing Sucrose as a Combustion Fuel Makhlouf, M. Th.; Abu-Zied, B. M.; Mansoure, T. H. Journal of Nanoparticles, Vol. 2013 https://doi.org/10.1155/2013/384350	journal	March 2013

Similar Records

Selective conversion of n-butene to isobutylene at extremely high space velocities on ZSM-23 zeolites

Journal Article · Mon Oct 31 23:00:00 EST 1994 · Journal of Catalysis · OSTI ID:28668

Epoxidation of lower olefins with hydrogen peroxide and titanium silicalite

Journal Article · Sun Feb 28 23:00:00 EST 1993 · Journal of Catalysis; (United States) · OSTI ID:7369081

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
heterogeneous catalysis
linear octene
oligomerization
pretreatment temperature
selectivity

Production of Linear Octenes from Oligomerization of 1-Butene over Carbon-Supported Cobalt Catalysts

Citation Formats

References (32)

Similar Records

Related Subjects