Abstract
CeO2/MWCNTs, Ag/MWCNTs and Ag–CeO2/MWCNTs hybrid composite nanomaterials with 5 wt% active component contents applied as catalysts of dehydrogenation and consecutive bimolecular condensation of a primary alcohol, butan-1-ol, revealed diversified properties. CeO2/MWCNTs showed the catalytic activity of pure cerium oxide despite its much lower content. Products obtained over Ag/MWCNTs did not contain ketone or ester in spite of higher dehydrogenation. Ag–CeO2/MWCNTs showed superior catalytic activity and selectivity towards subsequent C–C coupling, thus significantly higher yield of the symmetrical ketone (heptan-4-one) was achieved (at 400 °C, yield of the ketone over CeO2/MWCNTs and over Ag–CeO2/MWCNTs were 1 and 28%, respectively). The preserved character of the transformations over the CeO2/MWCNTs was shifted by tens of degrees to lower temperatures. It clearly indicates a synergistic interaction between the components.
Similar content being viewed by others
References
Aitchison H, Wingad RL, Wass DF (2016) Homogeneous ethanol to butanol catalysis—Guerbet renewed. ACS Catal 6:7125–7132
Prakash A, Dhabhai R, Sharma V (2016) A review on fermentative production of biobutanol from biomass. Curr Biochem Eng 3:37–46
Johnson E, Sarchami T, Kießlich S, Munch G, Rehmann L (2016) Consolidating biofuel platforms through the fermentative bioconversion of crude glycerol to butanol. World J Microbiol Biotechnol 32:103
Shelepova EV, Ilina LY, Vedyagin AA (2017) Kinetic studies of methanol dehydrogenation. Part I: copper-silica catalysts. Reac Kinet Mech Cat 120:449–458. doi:10.1007/s11144-016-1135-1
Wu L, Moteki T, Gokhale AA, Flaherty DW, Toste FD (2016) Production of fuels and chemicals from biomass: condensation reactions and beyond. Chem 1:32–58
Teterycz H, Klimkiewicz R, Łaniecki M (2004) Study on physico-chemical properties of tin dioxide based gas sensitive materials used in condensation reactions of n-butanol. Appl Catal A-Gen 274:49–60
Pham TN, Sooknoi T, Crossley SP, Resasco DE (2013) Ketonization of carboxylic acids: mechanisms, catalysts, and implications for biomass conversion. ACS Catal 3:2456–2473
Gliński M, Zalewski G, Burno E, Jerzak A (2014) Catalytic ketonization over metal oxide catalysts. xiii. Comparative measurements of activity of oxides of 32 chemical elements in ketonization of propanoic acid. Appl Catal A-Gen 470:278–284
James OO, Maity S, Mesubi MA, Usman LA, Ajanaku KO, Siyanbola TO, Sahu S, Chaubey R (2012) A review on conversion of triglycerides to on-specification diesel fuels without additional inputs. Int J Energy Res 36:691–702
Gaertner CA, Serrano-Ruiz JC, Braden DJ, Dumesic JA (2010) Ketonization reactions of carboxylic acids and esters over ceria–zirconia as biomass-upgrading processes. Ind Eng Chem Res 49:6027–6033
Phung TK, Casazza AA, Aliakbarian B, Finocchio E, Perego P, Busca G (2013) Catalytic conversion of ethyl acetate and acetic acid on alumina as models of vegetable oils conversion to biofuels. Chem Eng J 215–216:838–848
Krasnobaeva ON, Belomestnykh IP, Nosova TA, Elizarova TA, Isagulyants GV, Kolesnikov SP, Danilov VP (2011) Tantalum containing catalysts for oxydehydrogenation of hydrocarbons and alcohols. Russ J Inorg Chem 56:1012–1016
Wang CT, Ro SH (2005) Nanocluster iron oxide-silica aerogel catalysts for methanol partial oxidation. Appl Catal A-Gen 285:196–204
Kamiguchi S, Nishida S, Kodomari M, Chihara T (2005) Catalytic hydrodehydration of cyclohexanone, hydrogenation of 2-cyclohexen-1-one, and dehydrogenation of cyclohexene over a Mo chloride cluster with an octahedral metal framework. J Clust Sci 16:77–91
Jordison TL, Peereboom L, Miller DJ (2016) Impact of water on condensed phase ethanol Guerbet reactions. Ind Eng Chem Res 55:6579–6585
Ballarini N, Cavani F, Maselli L, Montaletti A, Passeri S, Scagliarini D, Flego C, Perego C (2007) The transformations involving methanol in the acid- and base-catalyzed gas-phase methylation of phenol. J Catal 251:423–436
Zawadzki M, Grabowska H, Trawczyński J (2010) Effect of synthesis method of LSCF perovskite on its catalytic properties for phenol methylation. Solid State Ion 181:1131–1139
Pal N, Paul M, Bhaumik A (2011) New mesoporous perovskite ZnTiO3 and its excellent catalytic activity in liquid phase organic transformations. Appl Catal A-Gen 393:153–160
Vivier L, Duprez D (2010) Ceria-based solid catalysts for organic chemistry. Chemsuschem 3:654–678
Gaertner CA, Serrano-Ruiz JC, Braden DJ, Dumesic JA (2009) Catalytic coupling of carboxylic acids by ketonization as a processing step in biomass conversion. J Catal 266:71–78
Deng D, Chen N, Li Y, Xing X, Liu X, Xiao X, Wang Y (2017) Cerium oxide nanoparticles/multi-wall carbon nanotubes composites: facile synthesis and electrochemical performances as supercapacitor electrode materials. Physica E 86:284–291
Ren LP, Dai WL, Cao Y, Li H, Fan K (2003) First observation of highly efficient dehydrogenation of methanol to anhydrous formaldehyde over novel Ag–SiO2–MgO–Al2O3 catalyst. Chem Commun 24:3030–3031
Vakhshouri AR, Azizov A, Aliyeva R, Bagirova S (2012) Synthesis, structure, and thermo-physical properties of Fe2O3. Al2O3 and polyethylene nanocomposites. J Appl Polym Sci 124:5106–5112
Lavkova J, Khalakhan I, Chundak M, Vorokhta M, Potin V, Matolin V, Matolinova I (2015) Growth and composition of nanostructured and nanoporous cerium oxide thin films on a graphite foil. Nanoscale 7:4038–4047
Biniak S, Szymański G, Siedlewski J,Świa̧tkowski A (1997) The characterization of activated carbons with oxygen and nitrogen surface groups. Carbon 35:1799–1810
Gergova K, Eser S, Schobert HH, Klimkiewicz M, Brown PW (1995) Environmental scanning electron microscopy of activated carbon production from anthracite by one-step pyrolysis-activation. Fuel 74:1042–1048
Klimkiewicz R (2010) Catalytic properties of activated carbons derived from lignite. Górnictwo Odkrywkowe 51:60–64
Yang ZH, Pan YM, Mei ZS, Zhang WX (2012) Preparation of mesoporous MnO2/C catalyst for n-hexyl acetate synthesis. Appl Surf Sci 258:4756–4763
Szychowski D, Pacewska B (2012) Methods of preparation and properties of mineral-carbon sorbents obtained from coal-tar pitch-polymer compositions. J Therm Anal Calorim 109:789–795
Klimkiewicz R, Morawski AW, Mista W (1993) Bi-K-graphite intercalation compound as a new catalyst for styrene synthesis. J Catal 144:627–631
Marchiol L (2012) Synthesis of metal nanoparticles in living plants. Ital J Agron 7:274–282. doi:10.4081/ija.2012.e37
Cyganiuk A, Klimkiewicz R, Bumajdad A, Włoch J, Kucinska A, Lukaszewicz JP (2014) Manufacture of a nanostructured CeOx/carbon catalyst for n-butanol conversion. Mater Lett 118:119–122
Narayanan KB, Sakthivel N (2011) Green synthesis of biogenic metal nanoparticles by terrestrial and aquatic phototrophic and heterotrophic eukaryotes and biocompatible agents. Adv Colloid Interface Sci 169:59–79
Zarubina V, Nederlof C, van der Linden B, Kapteijn F, Heeres HJ, Makkee M, Melián-Cabrera I (2014) Making coke a more efficient catalyst in the oxidative dehydrogenation of ethylbenzene using wide-pore transitional aluminas. J Mol Catal A: Chem 381:179–187
Cargnello M, Grzelczak M, Rodriguez-Gonzalez B, Syrgiannis Z, Bakhmutsky K, La Parola V, Liz-Marzan LM, Gorte RJ, Prato M, Fornasiero P (2012) Multiwalled carbon nanotubes drive the activity of metal@oxide core–shell catalysts in modular nanocomposites. J Am Chem Soc 134:11760–11766
Allaedini G, Tasirin SM, Aminayi P (2016) Yield optimization of nanocarbons prepared via chemical vapor decomposition of carbon dioxide using response surface methodology. Diam Relat Mater 66:196–205
Surisetty VR, Dalai AK, Kozinski J (2010) Alkali-promoted trimetallic Co-Rh-Mo sulfide catalysts for higher alcohols synthesis from synthesis gas: comparison of MWCNT and activated carbon supports. Ind Eng Chem Res 49:6956–6963
Almohalla M, Morales MV, Asedegbega-Nieto E, Maroto-Valiente A, Bachiller-Baeza B, Rodríguez-Ramos I, Guerrero-Ruiz A (2014) Bioethanol transformations over active surface sites generated on carbon nanotubes or carbon nanofibers materials. The Open Cat J 7:1–7
Liang XL, Dong X, Lin GD, Zhang HB (2009) Carbon nanotube-supported Pd–ZnO catalyst for hydrogenation of CO2 to methanol. Appl Catal B-Environ 88:315–322
Boncel S, Pattinson SW, Geiser V, Shaffer MSP, Koziol KKK (2014) En route to controlled catalytic CVD synthesis of densely packed and vertically aligned nitrogen-doped carbon nanotube arrays. Beilstein J Nanotechnol 5:219–233
Kovalska E (2013) Catalytic CVD-synthesis of carbon nanotubes, their modification and application. PhD Thesis, National Academy of Sciences of Ukraine, Kiev
Allaedini G, Tasirin SM, Aminayi P (2016) The effects of cerium doping concentration on the properties and photocatalytic activity of bimetallic Mo/Ce catalyst. Russ J Phys Chem A 90:2080–2088
Allaedini G, Aminayi P, Tasirin SM (2016) Methane decomposition for carbon nanotube production: optimization of the reaction parameters using response surface methodology. Chem Eng Res Des 112:163–174
Kundu S, Wang Y, Xia W, Muhler M (2008) Thermal stability and reducibility of oxygen-containing functional groups on multiwalled carbon nanotube surfaces: a quantitative high-resolution XPS and TPD/TPR study. J Phys Chem C 112:16869–16878
Yoo E, Habe T, Nakamura J (2005) Possibilities of atomic hydrogen storage by carbon nanotubes or graphite materials. Sci Technol Adv Mater 6:615–619
Orináková R, Orinák A (2011) Recent applications of carbon nanotubes in hydrogen production and storage. Fuel 90:3123–3140
Larese C, Lopez Granados M, Mariscal R, Fierro JLG, Lambrou PS, Efstathiou AM (2005) The effect of calcination temperature on the oxygen storage and release properties of CeO2 and Ce-Zr-O metal oxides modified by phosphorus incorporation. Appl Catal B-Environ 59:13–25
Ding M, Tang Y, Star A (2013) Understanding interfaces in metal–graphitic hybrid nanostructures. J Phys Chem Lett 4:147–160
Winiarska K, Klimkiewicz R, Winiarski J, Szczygieł I (2017) Mn0.6Zn0.4Fe2O4 ferrites prepared by the modified combustion method as the catalyst for butan-1-ol dehydrogenation. Reac Kinet Mech Cat 120:261–278. doi:10.1007/s11144-016-1095-5
Song S, Yang H, Rao R, Liu H, Zhang A (2010) High catalytic activity and selectivity for hydroxylation of benzene to phenol over multi-walled carbon nanotubes supported Fe3O4 catalyst. Appl Catal A-Gen 375:265–271
Rather S, Naik M, Hwang S, Kim A, Nahm K (2009) Room temperature hydrogen uptake of carbon nanotubes promoted by silver metal catalyst. J Alloys Compd 475:L17–L21
Wang ZX, Li XN, Ren CL, Yong ZZ, Zhu JK, Luo WY, Fang XM (2009) Growth of Ag nanocrystals on multiwalled carbon nanotubes and Ag-carbon nanotube interaction. Sci China Ser E Technol Sci 52:3215–3218
Wang CF, Guo SJ, Pan XL, Chen W, Bao XH (2008) Tailored cutting of carbon nanotubes and controlled dispersion of metal nanoparticles inside their channels. J Mater Chem 18:5782–5786
Arve K, Čapek L, Klingstedt F, Eränen K, Lindfors LE, Murzin DY, Dědeček J, Sobalik Z, Wichterlová B (2004) Preparation and characterisation of Ag/alumina catalysts for the removal of NOx emissions under oxygen rich conditions. Top Catal 30(31):91–95
Aneggi E, Llorca J, de Leitenburg C, Dolcetti G, Trovarelli A (2009) Soot combustion over silver-supported catalysts. Appl Catal B-Environ 91:489–498
Qu Z, Yu F, Zhang X, Wang Y, Gao J (2013) Support effects on the structure and catalytic activity of mesoporous Ag/CeO2 catalysts for CO oxidation. Chem Eng J 229:522–532
Kundakovic L, Flytzani-Stephanopoulos M (1998) Cu- and Ag- modified cerium oxide catalysts for methane oxidation. J Catal 179:203–221
Čičmanec P, Raabová K, Hidalgo JM, Kubička D, Bulánek R (2017) Conversion of ethanol to acetaldehyde over VOX-SiO2 catalysts: the effects of support texture and vanadium speciation. Reac Kinet Mech Cat 121:353–369
Requies J, Güemez MB, Iriondo A, Barrio VL, Cambra JF, Arias PL (2012) Bio n-butanol partial oxidation to butyraldehyde in gas phase on supported Ru and Cu catalysts. Catal Lett 142:417–426
Acknowledgements
This publication was created thanks to the Polish—Ukrainian Joint Research Project for years 2015–2017, under the agreement on scientific cooperation between the Polish Academy of Sciences and the National Academy of Sciences of Ukraine: Hybrid graphene nanomaterials for catalytic applications. The authors wish to thank Dr. Wojciech Gil (Faculty of Chemistry, University of Wrocław) for HRTEM measurements.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Dovbeshko, G., Kovalska, E., Miśta, W. et al. Bimolecular condensation reactions of butan-1-ol on Ag–CeO2 decorated multiwalled carbon nanotubes. Reac Kinet Mech Cat 122, 1063–1080 (2017). https://doi.org/10.1007/s11144-017-1254-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11144-017-1254-3