Reaction Kinetics, Mechanisms and Catalysis

, Volume 121, Issue 2, pp 523–537 | Cite as

Multilayer-stacked paper-structured catalysts for microflow Suzuki–Miyaura cross-coupling reaction

  • Yuki Ishihara
  • Kyohei Kanomata
  • Taichi Homma
  • Takuya Kitaoka
Article

Abstract

Paper-like porous composites of ceramic fibers and ZnO whiskers were prepared using a papermaking technique, followed by the in situ synthesis of a Pd catalyst on the ZnO whiskers using a facile impregnation method. The flexible Pd@ZnO papers had micrometer-sized pores of average diameter ca. 25 μm, which promoted the effective diffusion of reactants passing through an assembly of vertically stacked papers in a flow reactor. The catalytic efficiency of the stacked Pd@ZnO papers in a flow Suzuki–Miyaura cross-coupling (SMC) reaction to synthesize 4-methylbiphenyl from phenylboronic acid and 4-iodotoluene was higher than that of a bead-type Pd particulate catalyst in a reactor. Microchannels originating from the porous fiber-network microstructures in the stacked papers contributed to effective heterogeneous catalysis, possibly by enabling smooth diffusion of substrates to the surfaces of the Pd catalysts, as in a microreactor system. K2CO3, which was used as the base in the SMC reaction, was also immobilized in the paper-structured fibrous composites. Stacks of two types of paper, i.e., containing either Pd catalysts or K2CO3, significantly affected the SMC catalytic activity in a continuous microflow reaction. A combination of K2CO3 papers upstream and Pd@ZnO papers downstream in the flow system provided higher catalytic efficiency via on-site K2CO3-mediated borate formation of phenylboronic acid in the initial stage in the reactor. Tailoring of the stacking patterns of the paper-structured composites is expected to be effective for sequential SMC reaction and to improve catalytic process engineering.

Keywords

Flow reactor Microchannel Paper Porous material Sequential reaction 

Supplementary material

11144_2017_1178_MOESM1_ESM.docx (2.8 mb)
Supplementary material 1 (DOCX 2879 kb)

References

  1. 1.
    Pastre JC, Browne DL, Ley SV (2013) Flow chemistry syntheses of natural products. Chem Soc Rev 42:8849–8869CrossRefGoogle Scholar
  2. 2.
    Wegner J, Ceylan S, Kirschning A (2012) Flow chemistry—A key enabling technology for (multistep) organic synthesis. Adv Synth Catal 354:17–57CrossRefGoogle Scholar
  3. 3.
    DeMello AJ (2006) Control and detection of chemical reactions in microfluidic systems. Nature 442:394–402CrossRefGoogle Scholar
  4. 4.
    Sellin MF, Webb PB, Cole-hamilton DJ (2001) Continuous flow homogeneous catalysis: hydroformylation of alkenes in supercritical fluid–ionic liquid biphasic mixtures. Chem Commun 8:781–782CrossRefGoogle Scholar
  5. 5.
    Jensen KF (2001) Microreaction engineering—Is small better? Chem Eng Sci 56:293–303CrossRefGoogle Scholar
  6. 6.
    Carroccia L, Musio B, Degennaro L, Romanazzi G, Luisi R (2013) Microreactor-mediated organocatalysis: towards the development of sustainable domino reactions. J Flow Chem 3:29–33CrossRefGoogle Scholar
  7. 7.
    Yoshida J, Nagaki A, Yamada T (2008) Flash chemistry: fast chemical synthesis by using microreactors. Chem Eur J 14:7450–7459CrossRefGoogle Scholar
  8. 8.
    Mason BP, Price KE, Steinbacher JL, Bogdan AR, McQuade DT (2007) Greener approaches to organic synthesis using microreactor technology. Chem Rev 107:2300–2318CrossRefGoogle Scholar
  9. 9.
    Kobayashi J, Mori Y, Okamoto K, Akiyama R, UenoM Kitamori T, Kobayashi S (2004) A microfluidic device for conducting gas-liquid-solid hydrogenation reactions. Science 304:1305–1308CrossRefGoogle Scholar
  10. 10.
    Bogdan AR, Poe SL, Kubis DC, Broadwater SJ, McQuade DT (2009) The continuous-flow synthesis of ibuprofen. Angew Chem Int Ed 48:8547–8550CrossRefGoogle Scholar
  11. 11.
    Noël T, Buchwald SL (2011) Cross-coupling in flow. Chem Soc Rev 40:5010–5029CrossRefGoogle Scholar
  12. 12.
    Kikutani Y, Ueno M, Hisamoto H, Tokeshi M, Kitamori T (2005) Continuous-flow chemical processing in three-dimensional microchannel network for on-chip integration of multiple reactions in a combinatorial mode. QSAR Comb Sci 24:742–757CrossRefGoogle Scholar
  13. 13.
    Matatov-Meytal Y, Sheintuch M (2002) Catalytic fibers and cloths. Appl Catal A 231:1–16CrossRefGoogle Scholar
  14. 14.
    Höller V, Rådevik K, YuranovI Kiwi-Minsker L, Renken A (2001) Reduction of nitrite-ions in water over Pd-supported on structured fibrous materials. Appl Catal B 32:143–150CrossRefGoogle Scholar
  15. 15.
    Semagina N, Grasemann M, Xanthopoulos N, Renken A, Kiwi-Minsker L (2007) Structured catalyst of Pd/ZnO on sintered metal fibers for 2-methyl-3-butyn-2-ol selective hydrogenation. J Catal 251:213–222CrossRefGoogle Scholar
  16. 16.
    Matatov-Meytal Y, Barelko V, Yuranov I, Sheintuch M (2000) Cloth catalysts in water denitrification. I. Pd on glass fibers. Appl Catal B 27:127–135CrossRefGoogle Scholar
  17. 17.
    Jiao L, Jin BY (2013) Ceramic fiber application research. Appl Mech Mater 271–272:102–106Google Scholar
  18. 18.
    Bosko ML, Marchesini FA, Cornaglia LM, Miró EE (2013) Controlled Pd deposition on carbon fi bers by electroless plating. The effects of the support for the reduction of nitrite in water. Catal Today 212:16–22CrossRefGoogle Scholar
  19. 19.
    Cecchini JP, Banús ED, Leonardi SA, Zanuttini MA, Ulla MA, Milt VG (2014) Flexible-structured systems made of ceramic fibers containing Pt-NaY zeolite used as CO oxidation catalysts. J Mater Sci 50:755–768CrossRefGoogle Scholar
  20. 20.
    Höller V, Yuranov I, Kiwi-Minsker L, Renken A (2001) Structured multiphase reactors based on fibrous catalysts: nitrite hydrogenation as a case study. Catal Today 69:175–181CrossRefGoogle Scholar
  21. 21.
    Koga H, Fukahori S, Kitaoka T, Tomoda A, Suzuki R, Wariishi H (2006) Autothermal reforming of methanol using paper-like Cu/ZnO catalyst composites prepared by a papermaking technique. Appl Catal A 309:263–269CrossRefGoogle Scholar
  22. 22.
    Koga H, Umemura Y, Ishihara H, Kitaoka T, Tomoda A, Suzuki R, Wariishi H (2009) Paper-structured fiber composites impregnated with platinum nanoparticles synthesized on a carbon fiber matrix for catalytic reduction of nitrogen oxides. Appl Catal B 90:699–704CrossRefGoogle Scholar
  23. 23.
    Koga H, Kitaoka T, Wariishi H (2009) On-paper synthesis of Au nanocatalysts from Au(III) complex ions for low-temperature CO oxidation. J Mater Chem 19:5244–5249CrossRefGoogle Scholar
  24. 24.
    Koga H, Kitaoka T, Nakamura M, Wariishi H (2009) Influence of a fiber-network microstructure of paper-structured catalyst on methanol reforming behavior. J Mater Sci 44:5836–5841CrossRefGoogle Scholar
  25. 25.
    Koga H, Kitaoka T, Wariishi H (2009) In situ synthesis of silver nanoparticles on zinc oxide whiskers incorporated in a paper matrix for antibacterial applications. J Mater Chem 19:2135–2140CrossRefGoogle Scholar
  26. 26.
    Homma T, Kitaoka T (2014) Preparation of porous paper composites with ruthenium hydroxide and catalytic alcohol oxidation in a multiphase gas-liquid-solid reaction. Mater Sci Eng B 184:7–13CrossRefGoogle Scholar
  27. 27.
    Koga H, Umemura Y, Kitaoka T (2011) In situ synthesis of bimetallic hybrid nanocatalysts on a paper-structured matrix for catalytic applications. Catalysts 1:69–82CrossRefGoogle Scholar
  28. 28.
    Fukahori S, Koga H, Kitaoka T, Nakamura M, Wariishi H (2008) Steam reforming behavior of methanol using paper-structured catalysts: experimental and computational fluid dynamic analysis. Int J Hydrog Energy 33:1661–1670CrossRefGoogle Scholar
  29. 29.
    Miura S, Umemura Y, Shiratori Y, Kitaoka T (2013) In situ synthesis of Ni/MgO catalysts on inorganic paper-like matrix for methane steam reforming. Chem Eng J 229:515–521CrossRefGoogle Scholar
  30. 30.
    Shiratori Y, Quang-Tuyen T, Umemura Y, Kitaoka T, Sasaki K (2013) Paper-structured catalyst for the steam reforming of biodiesel fuel. Int J Hydrog Energy 38:11278–11287CrossRefGoogle Scholar
  31. 31.
    Koga H, Umemura Y, Kitaoka T (2011) Design of catalyst layers by using paper-like fiber/metal nanocatalyst composites for efficient NOX reduction. Compos Part B 42:1108–1113CrossRefGoogle Scholar
  32. 32.
    Koga H, Ishihara H, Kitaoka T, Tomoda A, Suzuki R, Wariishi H (2010) NOX reduction over paper-structured fiber composites impregnated with Pt/Al2O3 catalyst for exhaust gas purification. J Mater Sci 45:4151–4157CrossRefGoogle Scholar
  33. 33.
    Homma T, Kitaoka T (2016) Solvent-free alcohol oxidation using paper-structured catalysts: flow dynamics and reaction kinetics. Chem Eng J 285:467–476CrossRefGoogle Scholar
  34. 34.
    Homma T, Kitaoka T (2014) Multiphase catalytic oxidation of alcohols over paper-structured catalysts with micrometer-size pores. Appl Catal A 486:201–209CrossRefGoogle Scholar
  35. 35.
    Saimura A, Shiratori Y, Kitaoka T (2017) Dual-layered paper-structured catalysts for sequential desulfurization and methane-steam reforming of simulated biogas containing hydrogen sulfide. J Mater Sci 52:314–325CrossRefGoogle Scholar
  36. 36.
    Martin R, Buchwald SL (2008) Palladium-catalyzed Suzuki–Miyaura cross-coupling reactions employing dialkylbiaryl phosphine ligands. Acc Chem Res 41:1461–1473CrossRefGoogle Scholar
  37. 37.
    Sakurai H, Tsukuda T, Hirao T (2002) Pd/C as a reusable catalyst for the coupling reaction of halophenols and arylboronic acids in aqueous media. J Org Chem 67:2721–2722CrossRefGoogle Scholar
  38. 38.
    Chemler SR, Trauner D, Danishefsky SJ (2001) The B-alkyl Suzuki-Miyaura cross-coupling reaction: development, mechanistic study, and applications in natural product synthesis. Angew Chem Int Ed 40:4544–4568CrossRefGoogle Scholar
  39. 39.
    Ichiura H, Kubota Y, Wu ZH, Tanaka H (2001) Preparation of zeolite sheets using a papermaking technique, I. Dual polymer system for high retention of stock components. J Mater Sci 36:913–917CrossRefGoogle Scholar
  40. 40.
    Ichiura H, Kitaoka T, Tanaka H (2002) Preparation of composite TiO2–zeolite sheets using a papermaking technique and their application to environmental improvement, I. Removal of acetaldehyde with and without UV irradiation. J Mater Sci 37:2937–2941CrossRefGoogle Scholar
  41. 41.
    Ichiura H, Okamura N, Tanaka H, Kitaoka T (2001) Preparation of zeolite sheets using a papermaking technique, II. The strength of zeolite sheet and its hygroscopic characteristics. J Mater Sci 36:4921–4926CrossRefGoogle Scholar
  42. 42.
    Yacou C, Sunarso J, Lin CXC, Smart S, Liu S, Diniz da Costa JC (2011) Palladium surface modified La0.6Sr0.4Co0.2Fe0.8O3-δ hollow fibres for oxygen separation. J Membr Sci 380:223–231CrossRefGoogle Scholar
  43. 43.
    Yang X, Li Q, Wang H, Huang J, Lin L, Wang W, Sun D, Su Y, Opiyo JB, Hong L, Wang Y, He N, Jia L (2010) Green synthesis of palladium nanoparticles using broth of Cinnamomum camphora leaf. J Nanopart Res 12:1589–1598CrossRefGoogle Scholar
  44. 44.
    Hong CT, Yeh CT, Yu FH (1989) Effect of reduction and oxidation treatments on Pd/ZnO catalysts. Appl Catal 48:385–396CrossRefGoogle Scholar
  45. 45.
    Iwasa N, Mayanagi T, Nomura W, Arai M, Takezawa N (2003) Effect of Zn addition to supported Pd catalysts in the steam reforming of methanol. Appl Catal A 248:153–160CrossRefGoogle Scholar
  46. 46.
    Liu S, Takahashi K, Uematsu K, Ayabe M (2005) Hydrogen production by oxidative methanol reforming on Pd/ZnO. Appl Catal A 283:125–135CrossRefGoogle Scholar
  47. 47.
    Liu S, Takahashi K, Uematsu K, Ayabe M (2004) Hydrogen production by oxidative methanol reforming on Pd/ZnO catalyst: effects of the addition of a third metal component. Appl Catal A 277:265–270CrossRefGoogle Scholar
  48. 48.
    Hosseini-Sarvari M, Razmi Z (2015) Palladium supported on zinc oxide nanoparticles as efficient heterogeneous catalyst for Suzuki-Miyaura and Hiyama reactions under normal laboratory conditions. Helv Chim Acta 98:805–818CrossRefGoogle Scholar
  49. 49.
    Larrosa I, Somoza C, Banquy A, Goldup SM (2011) Two flavors of PEPPSI-IPr: activation and diffusion control in a single NHC-ligated Pd catalyst? Org Lett 13:146–149CrossRefGoogle Scholar
  50. 50.
    Deverell JA, Rodemann T, Smith JA, CantyAJ Guijt RM (2011) UV initiated formation of polymer monoliths in glass and polymer microreactors. Sens Actuators B 155:388–396CrossRefGoogle Scholar
  51. 51.
    Comer E, Organ MG (2005) A microreactor for microwave-assisted capillary (continuous flow) organic synthesis. J Am Chem Soc 127:8160–8167CrossRefGoogle Scholar
  52. 52.
    Greenway GM, Haswell SJ, Morgan DO, Skelton V, Styring P (2000) Use of a novel microreactor for high throughput continuous flow organic synthesis. Sens Actuators B 63:153–158CrossRefGoogle Scholar
  53. 53.
    Braga AAC, Ujaque G, Maseras F (2006) A DFT Study of the full catalytic cycle of the Suzuki-Miyaura cross-coupling on a model system. Organometallics 25:3647–3658CrossRefGoogle Scholar
  54. 54.
    Braga AAC, Morgon NH, Ujaque G, Maseras F (2005) Computational characterization of the role of the base in the Suzuki-Miyaura cross-coupling reaction. J Am Chem Soc 127:9298–9307CrossRefGoogle Scholar
  55. 55.
    Carrow BP, Hartwig JF (2011) Distinguishing between pathways for transmetallation in Suzuki-Miyuara reactions. J Am Chem Soc 133:2116–2119CrossRefGoogle Scholar

Copyright information

© Akadémiai Kiadó, Budapest, Hungary 2017

Authors and Affiliations

  • Yuki Ishihara
    • 1
  • Kyohei Kanomata
    • 1
  • Taichi Homma
    • 1
    • 2
  • Takuya Kitaoka
    • 1
  1. 1.Department of Agro-Environmental Sciences, Graduate School of Bioresource and Bioenvironmental SciencesKyushu UniversityFukuokaJapan
  2. 2.Processing Development Research LaboratoryKao CorporationTochigiJapan

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