Mechanocatalytic Approaches to Biomass Conversion
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1 Mechanocatalytic Approaches to Biomass Conversion Carsten Sievers March 10, 2015 Atlanta, GA
2 Sievers Research Group Catalytic Routes for Sustainable Production of Fuels and Chemicals Synthesis Characterization Surface Reactions Process Development Tailored active sites Acidity / Basicity In-situ spectroscopy Catalytic reactions Watertolerant solid acid Multifunctional catalysts Metal particles Porosity Crystallinity Intermediates Reaction pathways Reactor design Deactivation carsten.sievers@chbe.gatech.edu Phone: , Fax:
3 Stability of Solid Catalysts in ot Water bjectives: Understanding the pathways of catalyst deactivation in hot liquid water Elucidating the influence of biomass-derived feedstocks on the stability of solid catalysts Improving the hydrothermal stability of solid catalysts using protective coatings and additives ppm t / h 2θ / ppm t / h Approaches: Kinetic studies on transformations of solid catalysts in hot water and solutions of oxygenates Physicochemical characterization (N 2 physisorption, XRD, TEM, SEM, IR, NMR, XPS, titration) Development of synthesis techniques for improving hydrothermal stability Performance studies with stabilized catalysts Al 3+ + Pt 2 + Cl Al R.M. Ravenelle et al., J. Phys. Chem. C 114 (2010) R.M. Ravenelle et al., ACS Catal. 1 (2011) 552. R.M. Ravenelle et al., Top. Catal. 55 (2012) 162. R.M. Ravenelle et al., ChemCatChem 4 (2012) 492. A.L. Jongerius et al., ACS Catalysis 3 (2013) 464. M.W. ahn et al., ChemSusChem 6 (2013) A.. Van Pelt et al., Carbon 77 (2014) 143.
4 Surface Chemistry of xygenates in Water bjectives: Understanding surface interactions of biomass-derived oxygenates in aqueous media Identification of intermediates and reaction pathways for reactions such as aqueous phase reforming and hydrodeoxygenation (D) Quantification of rates of individual reaction steps Identification of active sites for specific reaction paths Characterization of solvent effects Glycerol on γ-al C3 C2 C Approaches: IR spectroscopy (in vacuum, vapor phase ( 1 atm), and liquid phase) NMR spectroscopy Liquid phase adsorption isotherms Inelastic neutron scattering Raman spectroscopy DFT calculations (in collaboration with David Sholl) Al1 Al2 1 ATR IR setup for in-situ studies in liquid phase under flow conditions IRE Effluent TC eating Element Feed Inlet N 2 Inlet Gasket Window IR utlet IR Inlet J.R. Copeland et al., Langmuir 29 (2013) 581. J.R. Copeland et al., Catal. Today 205 (2013) 49. J.R. Copeland et al., J. Phys. Chem. C 117 (2013) Foo et al., ACS Catalysis 4 (2014) 3180.
5 Continuous Conversion Biomass bjectives: Development of stable solid catalysts Reactivity studies with model compounds and real feedstocks Identification of structure property relationships to improve selectivity Quantitative description of intrinsic kinetics and transport limitations Development of suitable regeneration procedures for spent catalysts Approaches: Synthesis and post-synthesis treatments of of solid catalysts Physicochemical characterization (N 2 physisorption, XRD, SEM, IR, NMR, XPS, Boehm titration) Reactivity studies using a flow reactor setup with automated sample collection + 2 Foo et al., ChemSusChem, 8 (2015) 534. A.. Van Pelt et al., Carbon 77 (2014) 143.
6 Sulfur-Free D Catalysts bjectives: Development of ceria-zirconia based catalysts for hydrodeoxygenation of oxygenates in pyrolysis oils. These catalysts will not contain noble metals and will not require 2 S to be co-fed ptimization of the composition and morphology of the catalysts Analysis of reaction kinetics Identification of structure-property relationships Ce x Zr y z Ce x Zr y z Approaches: Synthesis mixed-metal oxide catalysts with different compositions and morphologies Physicochemical characterization (TPR, isotopic scrambling of 2 /D 2, N 2 physisorption, XRD, TEM, SEM, IR, NMR, XPS, titration) In-situ spectroscopic studies Reactivity studies using a continuously operated trickle bed reactor Ce x Zr y z Ce x Zr y z
7 Mechanocatalytic Reactions Reactants, catalysts, and milling balls are mixed. No solvents are used during the milling. Separation of products can become more efficient. Shaker Mill Q. Zhang, and F. Jerome, ChemSusChem 6 (2013) 2042.
8 Catalytic Sites in Ball Milling Shaker Mill C + 1/2 2 C 2 over Cr 2 3 The rate of C oxidation over a Cr 2 3 catalysts increased dramatically when the shaker mill is running. The effect is completely reversibly and repeatable. Milling creates short lived but highly active catalytic sites. Shaker Mill Plug Flow Reactor S. Immohr, M. Felderhoff, C. Weidenthaler, F. Schüth, Angew. Chem. Int. Ed. 52 (2013)
9 Composition of Biomass Cellulose Lignin C 3 C 2 2 C 2 C emicellulose 2 C 2 C R 2 C R 2 C 2 C 2 C R R R R 2 C 3 C C [ C 2 ] 3 C C C C 2 C C 2 C C C 2 C 3 C C 3 C C 2 C 3 C 2 C C C 2 C C C 2 C C C 3 3 C C 2 3 C C C 3 C 2 C C 2 C C C 2 C C C C 2 C C C C 2 C 3 C C C 3 3 C C 2 C C C 2 3 C C C 3 C C 3 [ C ]
10 ydrolysis of Carbohydrates 2 [ + ] Carbohydrates can be depolymerized by addition of water to the glycosidic bond. ydrolysis of carbohydrates is catalyzed by acids or enzymes.
11 Mechanocatalytic Conversion of Cellulose Solid acid can be used to depolymerize cellulose in a ball mill. Grinding provides intimate contact between reactant and catalytically active sites. Water-soluble compounds are obtained as main products. Dealuminated kaolinite is an efficient catalyst. S.M. ick, C. Griebel, D.T. Restrepo, J.. Truitt, E.J. Buker, C. Bylda, R.G. Blair, Green Chem. 12 (2010) 468. Blair, R. G.; ick, S. M.; Truitt, J.., US patent 8,062,428 (2011).
12 Mechanocatalytic Conversion of Cellulose ESI-MS spectrum of water-soluble products from cellulose Very high yields of water-soluble products can be obtained when cellulose is impregnated with mineral acid before ball milling. ligosaccharides are the main products. Formation of branched oligosaccharides indicates re-polymerization. Monosaccharides can be obtained by hydrolysis under mild conditions. N. Meine, R. Rinaldi, and F. Schüth, ChemSusChem 5 (2012) J. ilgert, N. Meine, R. Rinaldi, and F. Schüth, Energy Environ. Sci. 6 (2013)
13 Lignin Structure J. Zakzeski, P.C.A. Bruijnincx, A.L. Jongerius, B.M. Weckhuysen, Chem. Rev. 110 (2010) 3552.
14 Conversion of Lignin Lignin can be cracked over solid acid catalysts at 350 to 400 C. Initial conversion of non-volatiles to volatiles. Volatiles can be further converted to light gases and chars. Moderate yields of valuable aromatics. Strong bases catalyze hydrolysis of ether linkages. Significant amounts of basic waste are formed. Few processes for the conversion of lignin are economically viable. J. Zakzeski, P.C.A. Bruijnincx, A.L. Jongerius, B.M. Weckhuysen, Chem. Rev. 110 (2010) 3552.
15 Possible Products from Lignin Propyl benzene has an octane rating of and could be used to improve the quality of gasoline. Benzene, toluene, xylene (BTX) are used in many processes in the chemical industry. For example terephthalic acid is produced from p-xylene.
16 Mechanocatalytic Conversion of Lignin Base assisted ball milling facilitates cleavage of β--4 linkages in lignin. Depolymerization of carbohydrates is observed in parallel. Currently the amounts of base (Na) required are too large for an attractive process. T. Kleine, J. Buendia, C. Bolm, Green Chem. 15 (2013) 160.
17 Clay Based Catalysts Natural clays are generally cheap. Certain natural clays are solid acids and bases. Thermal treatments can enhance acid-base properties. Ion exchange of clays can add Lewis acid and base sites. Addition of reduced metal particles (e.g. Ni, Cu) can facilitate reaction involving hydrogen.
18 Adsorption of Probe Molecules bjectives: Quantification of the concentration of acid and base sites on solids Characterization of strength of sites Absorbance / a.u Approaches: Adsorption of probe molecules (e.g. pyridine, C 2 ) on solid acid and bases just before the ball mill is turned of Analysis by IR spectroscopy Analysis of desorption temperatures to obtain a strength distribution Wavenumber / cm -1 Lewis acid sites IR band at 1450 cm -1 IR band at 1540 cm -1 Brønsted acid sites J.R. Copeland, I.A. Santillan, S.M. Schimming, J.L. Ewbank, C. Sievers, J. Phys. Chem. C 117 (2013) M.W. ahn, J.R. Copeland, A.. Van Pelt, C. Sievers, ChemSusChem 6 (2013) Y. Kuwahara, D.-Y. Kang, J.R. Copeland, N.A. Brunelli, S.A. Didas, P. Bollini, C. Sievers, T. Kamegawa,. Yamashita, C.W. Jones, J. Am. Chem. Soc. 134 (2012)
19 Mechanocatalytic ydrotreating Metal sites can dissociate molecular hydrogen to atomic hydrogen. Atomic hydrogen can spillover to other sites. W.C. Conner, J.L. Falconer, Chem. Rev. 95 (1995) 759.
20 Mechanocatalytic ydrotreating Atomic hydrogen can quench dangling bonds and prevent radical reactions like graphitization. + 2 Removal of oxygen containing functional groups is facilitated when bonds angles are distorted. Shear force
21 Continuous Removal of Products 2 feed Lignin feed 2 recycle Ball mill Condenser Liquid products Small and deoxygenated lignin fragments are volatile and can be removed as vapors. ydrogen can be separated from the products using a condenser or membrane.
22 Messages From This Presentation Possible applications of the insights/ techniques/findings/opportunities in this presentation Conversion of lignin into chemicals and fuel additives Utilization of other solid, carbon-based feedstocks Barriers and challenges to success Lack of understanding of mechanocatalytic reactions Energy efficiency of milling processes Additional research opportunities Processes for mechanocatalytic hydrotreating and other approaches to biomass conversion Improving mechanocatalytic processes based on understanding their fundamentals
Production of Renewable Chemicals. Pieter. C. A. Bruijnincx, Joseph Zakzeski, Anna L. Jongerius, and Bert M. Weckhuysen
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