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Erschienen in: Biomass Conversion and Biorefinery 4/2014

01.12.2014 | Original Article

Hydrogenation of levulinic acid and γ-valerolactone: steps towards biofuels

verfasst von: Sandip N. Derle, Parimal A. Parikh

Erschienen in: Biomass Conversion and Biorefinery | Ausgabe 4/2014

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Abstract

Several bifunctional catalysts (Pt, Au, Ni supported on ZSM-5, zeolite Beta, silica and alumina) were evaluated for hydrogenation of levulinic acid (LA) and γ-valerolactone (GVL). Among these, Pt supported on parent- and desilicated-zeolite Beta showed better catalytic activity for hydrogenation of gamma valerolactone to valeric acid (VA) with >98 % selectivity. Noteworthy catalytic activity of Au supported on desilicated zeolite Beta in GVL to VA hydrogenation was observed. Other catalysts such as Pt/γ-alumina, Ni/desilicated zeolite Beta and Ni/SiO2 did not exhibit significant catalytic activity in GVL hydrogenation. Pt and Au-supported zeolite catalysts were also tested for hydrogenation of LA to GVL. Pt supported on zeolites decomposed formic acid (FA) to CO2 and H2 and in situ produced H2 hydrogenated LA to GVL. Pt impregnated desilicated zeolite Beta was found to retain its integrity even after prolonged exposure to hot VA solution and neither Pt nor Al leached into solution.

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Literatur
1.
Zurück zum Zitat Centi G, Lanzafame P, Perathoner S (2011) Analysis of the alternative routes in the catalytic transformation of lignocellulosic materials. Catal Today 167:14–30CrossRef Centi G, Lanzafame P, Perathoner S (2011) Analysis of the alternative routes in the catalytic transformation of lignocellulosic materials. Catal Today 167:14–30CrossRef
2.
Zurück zum Zitat Serrano-Ruiz JC, Pineda A, Balu AM, Luque R, Campelo JM, Romero AA, Ramos-Fernandez JM (2012) Catalytic transformations of biomass-derived acids into advanced biofuels. Catal Today 195:162–168CrossRef Serrano-Ruiz JC, Pineda A, Balu AM, Luque R, Campelo JM, Romero AA, Ramos-Fernandez JM (2012) Catalytic transformations of biomass-derived acids into advanced biofuels. Catal Today 195:162–168CrossRef
3.
Zurück zum Zitat Serrano-Ruiz JC, Braden DJ, West RM, Dumesic JA (2010) Conversion of cellulose to hydrocarbon fuels by progressive removal of oxygen. Appl Catal B Environ 100:184–189CrossRef Serrano-Ruiz JC, Braden DJ, West RM, Dumesic JA (2010) Conversion of cellulose to hydrocarbon fuels by progressive removal of oxygen. Appl Catal B Environ 100:184–189CrossRef
4.
Zurück zum Zitat Stefanidis SD, Kalogiannis KG, Iliopoulou EF, Lappas AA, Pilavachi PA (2011) In-situ upgrading of biomass pyrolysis vapors: catalyst screening on a fixed bed reactor. Bioresour Technol 102:8261–8267CrossRef Stefanidis SD, Kalogiannis KG, Iliopoulou EF, Lappas AA, Pilavachi PA (2011) In-situ upgrading of biomass pyrolysis vapors: catalyst screening on a fixed bed reactor. Bioresour Technol 102:8261–8267CrossRef
5.
Zurück zum Zitat Lange J, Price R, Ayoub PM, Louis J, Petrus L, Clarke L, Gosselink H (2010) Valeric biofuels: a platform of cellulosic transportation Fuels. Angew Chem Int Ed 49:4479–4483CrossRef Lange J, Price R, Ayoub PM, Louis J, Petrus L, Clarke L, Gosselink H (2010) Valeric biofuels: a platform of cellulosic transportation Fuels. Angew Chem Int Ed 49:4479–4483CrossRef
6.
Zurück zum Zitat Buitrago-Sierra R, Serrano-Ruiz JC, Rodríguez-Reinoso F, Sepúlveda-Escribano A, Dumesic JA (2012) Ce promoted Pd–Nb catalysts for γ-valerolactone ring-opening and hydrogenation. Green Chem 14:3318–3324CrossRef Buitrago-Sierra R, Serrano-Ruiz JC, Rodríguez-Reinoso F, Sepúlveda-Escribano A, Dumesic JA (2012) Ce promoted Pd–Nb catalysts for γ-valerolactone ring-opening and hydrogenation. Green Chem 14:3318–3324CrossRef
7.
Zurück zum Zitat Rackemann DW, Doherty WO (2011) Biofuels: the conversion of lignocellulosics to levulinic acid. Bioprod Bioref 5:115–126CrossRef Rackemann DW, Doherty WO (2011) Biofuels: the conversion of lignocellulosics to levulinic acid. Bioprod Bioref 5:115–126CrossRef
8.
Zurück zum Zitat Alonso DM, Wettstein SG, Dumesic JA (2013) Gamma-valerolactone, a sustainable platform molecule derived from lignocellulosic biomass. Green Chem 15:584–595CrossRef Alonso DM, Wettstein SG, Dumesic JA (2013) Gamma-valerolactone, a sustainable platform molecule derived from lignocellulosic biomass. Green Chem 15:584–595CrossRef
9.
Zurück zum Zitat Alonso DM, Bond JQ, Dumesic JA (2010) Catalytic conversion of biomass to biofuels. Green Chem 12:1493–1513CrossRef Alonso DM, Bond JQ, Dumesic JA (2010) Catalytic conversion of biomass to biofuels. Green Chem 12:1493–1513CrossRef
10.
Zurück zum Zitat Hayes D (2009) An examination of biorefining processes, catalysts and challenges. Catal Today 145:138–151CrossRef Hayes D (2009) An examination of biorefining processes, catalysts and challenges. Catal Today 145:138–151CrossRef
11.
Zurück zum Zitat Wettstein SG, Alonso DM, Gurbuz EI, Dumesic JA (2012) A roadmap for conversion of lignocellulosic biomass to chemicals and fuels. Curr Opin Chem Eng 1:218–224CrossRef Wettstein SG, Alonso DM, Gurbuz EI, Dumesic JA (2012) A roadmap for conversion of lignocellulosic biomass to chemicals and fuels. Curr Opin Chem Eng 1:218–224CrossRef
12.
Zurück zum Zitat Chan-Thaw CE, Marelli M, Psaro R, Ravasio N, Zaccheriaa F (2013) New generation biofuels: γ-valerolactone into valeric esters in one pot. RSC Adv 3:1302–1306CrossRef Chan-Thaw CE, Marelli M, Psaro R, Ravasio N, Zaccheriaa F (2013) New generation biofuels: γ-valerolactone into valeric esters in one pot. RSC Adv 3:1302–1306CrossRef
13.
Zurück zum Zitat Upare PP, Lee JM, Hwang DW, Halligudi SB, Hwang YK, Chang JS (2011) Selective hydrogenation of levulinic acid to g-valerolactone over carbon-supported noble metal catalysts. J Ind Eng Chem 17:287–292CrossRef Upare PP, Lee JM, Hwang DW, Halligudi SB, Hwang YK, Chang JS (2011) Selective hydrogenation of levulinic acid to g-valerolactone over carbon-supported noble metal catalysts. J Ind Eng Chem 17:287–292CrossRef
14.
Zurück zum Zitat Raspolli Galletti AM, Antonetti C, Ribechini E, Colombini MP, Nasso NN, Bonari E (2012) From giant reed to levulinic acid and gamma-valerolactone: a high yield catalytic route to valeric biofuels. Appl Energy 102:157–162CrossRef Raspolli Galletti AM, Antonetti C, Ribechini E, Colombini MP, Nasso NN, Bonari E (2012) From giant reed to levulinic acid and gamma-valerolactone: a high yield catalytic route to valeric biofuels. Appl Energy 102:157–162CrossRef
15.
Zurück zum Zitat Braden DJ, Henao CA, Heltzel J, Maravelias CC, Dumesic JA (2011) Production of liquid hydrocarbon fuels by catalytic conversion of biomass-derived levulinic acid. Green Chem 13:1755–1765CrossRef Braden DJ, Henao CA, Heltzel J, Maravelias CC, Dumesic JA (2011) Production of liquid hydrocarbon fuels by catalytic conversion of biomass-derived levulinic acid. Green Chem 13:1755–1765CrossRef
16.
Zurück zum Zitat Wettstein SG, Bond JQ, Alonso DM, Pham HN, Datye AK, Dumesic JA (2012) RuSn bimetallic catalysts for selective hydrogenation of levulinic acid to γ-valerolactone. Appl Catal B Environ 117–118:321–329CrossRef Wettstein SG, Bond JQ, Alonso DM, Pham HN, Datye AK, Dumesic JA (2012) RuSn bimetallic catalysts for selective hydrogenation of levulinic acid to γ-valerolactone. Appl Catal B Environ 117–118:321–329CrossRef
17.
Zurück zum Zitat Luo W, Deka U, Beale AM, van Eck ERH, Bruijnincx PCA, Weckhuysen BM (2013) Ruthenium-catalyzed hydrogenation of levulinic acid: influence of the support and solvent on catalyst selectivity and stability. J Catal 301:175–186CrossRef Luo W, Deka U, Beale AM, van Eck ERH, Bruijnincx PCA, Weckhuysen BM (2013) Ruthenium-catalyzed hydrogenation of levulinic acid: influence of the support and solvent on catalyst selectivity and stability. J Catal 301:175–186CrossRef
18.
Zurück zum Zitat Modhera BK, Chakraborty M, Bajaj HC, Parikh PA (2011) Influences of mesoporosity generation in ZSM-5 and zeolite beta on catalytic performance during n-hexane isomerization. Catal Lett 141:1182–1190CrossRef Modhera BK, Chakraborty M, Bajaj HC, Parikh PA (2011) Influences of mesoporosity generation in ZSM-5 and zeolite beta on catalytic performance during n-hexane isomerization. Catal Lett 141:1182–1190CrossRef
19.
Zurück zum Zitat Curtis Conner Jr W, Falconer JL (1995) Spillover in heterogeneous catalysis. Chem Rev 95:759–788CrossRef Curtis Conner Jr W, Falconer JL (1995) Spillover in heterogeneous catalysis. Chem Rev 95:759–788CrossRef
20.
Zurück zum Zitat Corma A, Serna P (2006) Chemoselective hydrogenation of nitro compounds with supported gold catalysts. Science 313:332–334CrossRef Corma A, Serna P (2006) Chemoselective hydrogenation of nitro compounds with supported gold catalysts. Science 313:332–334CrossRef
21.
Zurück zum Zitat Riahi G, Guillemot D, Polisset-Thfoin M, Khodadadi AA, Fraissard J (2002) Preparation, characterization and catalytic activity of gold-based nanoparticles on HY zeolites. Catal Today 72:115–121CrossRef Riahi G, Guillemot D, Polisset-Thfoin M, Khodadadi AA, Fraissard J (2002) Preparation, characterization and catalytic activity of gold-based nanoparticles on HY zeolites. Catal Today 72:115–121CrossRef
22.
Zurück zum Zitat Caillot T, Gauthier G, Delichère P, Cayron C, Cadete Santos Aires FJ (2012) Evidence of anti-coking behaviour of La0.8Sr0.2Cr0.98Ru0.02O3as potential anode material for solid oxide fuel cells directly fed under methane. J Catal 290:158–164CrossRef Caillot T, Gauthier G, Delichère P, Cayron C, Cadete Santos Aires FJ (2012) Evidence of anti-coking behaviour of La0.8Sr0.2Cr0.98Ru0.02O3as potential anode material for solid oxide fuel cells directly fed under methane. J Catal 290:158–164CrossRef
23.
Zurück zum Zitat Batalha N, Pinard L, Pouilloux Y, Guisnet M (2013) Bifunctional hydrogenating /acid catalysis: quantification of the intimacy criterion. Catal Lett 143(6):587–591CrossRef Batalha N, Pinard L, Pouilloux Y, Guisnet M (2013) Bifunctional hydrogenating /acid catalysis: quantification of the intimacy criterion. Catal Lett 143(6):587–591CrossRef
24.
Zurück zum Zitat Yu WA, Mullen GM, Mullins CB (2013) Hydrogen adsorption and absorption with Pd−Au bimetallic surfaces. J Phys Chem C 117:19535–19543, and references therein Yu WA, Mullen GM, Mullins CB (2013) Hydrogen adsorption and absorption with Pd−Au bimetallic surfaces. J Phys Chem C 117:19535–19543, and references therein
25.
Zurück zum Zitat Bond JQ, Wang D, Alonso DM, Dumesic JA (2011) Interconversion between γ-valerolactone and pentenoic acid combinedwith decarboxylation to form butene over silica/alumina. J Catal 281:290–299CrossRef Bond JQ, Wang D, Alonso DM, Dumesic JA (2011) Interconversion between γ-valerolactone and pentenoic acid combinedwith decarboxylation to form butene over silica/alumina. J Catal 281:290–299CrossRef
26.
Zurück zum Zitat Bond JQ, Alonso DM, Wang D, West RM, Dumesic JA (2010) Integrated catalytic conversion of gamma-valerolactone to liquid alkenes for transportation fuels. Science 327:1110–1114CrossRef Bond JQ, Alonso DM, Wang D, West RM, Dumesic JA (2010) Integrated catalytic conversion of gamma-valerolactone to liquid alkenes for transportation fuels. Science 327:1110–1114CrossRef
27.
Zurück zum Zitat Palkovits R (2010) Cellulosic Biofuels. Angew Chem Int Ed 49:4336–4338CrossRef Palkovits R (2010) Cellulosic Biofuels. Angew Chem Int Ed 49:4336–4338CrossRef
28.
Zurück zum Zitat Palkovits R (2013) Personal communication Palkovits R (2013) Personal communication
29.
Zurück zum Zitat Hengne AM, Rode CV (2012) Cu–ZrO2 nanocomposite catalyst for selective hydrogenation of levulinic acid and its ester to γ-valerolactone. Green Chem 14:1064–1072CrossRef Hengne AM, Rode CV (2012) Cu–ZrO2 nanocomposite catalyst for selective hydrogenation of levulinic acid and its ester to γ-valerolactone. Green Chem 14:1064–1072CrossRef
30.
Zurück zum Zitat Yan ZP, Lin L, Liu SJ (2009) Synthesis of γ-valerolactone by hydrogenation of biomass-derived levulinic acid over ru/c catalyst. Energy Fuel 23:3853–3858CrossRef Yan ZP, Lin L, Liu SJ (2009) Synthesis of γ-valerolactone by hydrogenation of biomass-derived levulinic acid over ru/c catalyst. Energy Fuel 23:3853–3858CrossRef
31.
Zurück zum Zitat Li DJ, Lai DM, Fu Y, Guo QX (2009) Catalytic conversion of biomass-derived carbohydrates into γ-valerolactone without using an external H2 supply. Angew Chem Int Ed 48:6529–6532CrossRef Li DJ, Lai DM, Fu Y, Guo QX (2009) Catalytic conversion of biomass-derived carbohydrates into γ-valerolactone without using an external H2 supply. Angew Chem Int Ed 48:6529–6532CrossRef
32.
Zurück zum Zitat Hengne AM, Biradar NS, Rode CV (2012) Surface species of supported ruthenium catalysts in selective hydrogenation of levulinic esters for bio-refinery application. Catal Lett 142:779–787CrossRef Hengne AM, Biradar NS, Rode CV (2012) Surface species of supported ruthenium catalysts in selective hydrogenation of levulinic esters for bio-refinery application. Catal Lett 142:779–787CrossRef
33.
Zurück zum Zitat Bozell JJ (2010) Connecting biomass and petroleum refining with a chemical bridge. Science 329:522–523CrossRef Bozell JJ (2010) Connecting biomass and petroleum refining with a chemical bridge. Science 329:522–523CrossRef
Metadaten
Titel
Hydrogenation of levulinic acid and γ-valerolactone: steps towards biofuels
verfasst von
Sandip N. Derle
Parimal A. Parikh
Publikationsdatum
01.12.2014
Verlag
Springer Berlin Heidelberg
Erschienen in
Biomass Conversion and Biorefinery / Ausgabe 4/2014
Print ISSN: 2190-6815
Elektronische ISSN: 2190-6823
DOI
https://doi.org/10.1007/s13399-013-0111-5

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