Skip to main content
Erschienen in: Biomass Conversion and Biorefinery 5/2021

02.01.2020 | Original Article

Conversion of biorenewably available acetone and butanol to liquid fuels using base catalysts

verfasst von: Tarun Pratap Singh Jadon, Arun Kumar Jana, Parimal A. Parikh

Erschienen in: Biomass Conversion and Biorefinery | Ausgabe 5/2021

Einloggen

Aktivieren Sie unsere intelligente Suche, um passende Fachinhalte oder Patente zu finden.

search-config
loading …

Abstract

We studied acetone butylation over KF/Na-ZSM-5 and ZSM-5 impregnated with other K-compounds which impart basicity. These base catalysts have, so far, not been reported for ketone alkylation. These catalysts did not contain any metal any of metal which are conventionally used to affect dehydrogenation-hydrogenation reactions which have been reported to be involved in mechanism of acetone alkylation. Absence of such metals reduces catalyst costs and eliminates metal sintering. Catalyst basicity was determined by FTIR of pyrrole-adsorbed samples and CO2 adsorption method. Coke deposited after reaction for 20 h time-on-stream on promising catalyst, namely, 10 wt% KF/Na-ZSM-5, was characterized by TGA and GCMS. This confirmed stability of KF on Na-ZSM-5, without leaching of F. Acetone conversion (60%) and ketone plus alcohol selectivity (exceeding 90%) surpassed reported performance at comparable operating conditions.

Sie haben noch keine Lizenz? Dann Informieren Sie sich jetzt über unsere Produkte:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literatur
1.
Zurück zum Zitat Dürre P (2007) Biobutanol: an attractive biofuel. Biotechnology Journal: Healthcare Nutrition Technology 2(12):1525–1534 Dürre P (2007) Biobutanol: an attractive biofuel. Biotechnology Journal: Healthcare Nutrition Technology 2(12):1525–1534
2.
Zurück zum Zitat Jin C, Yao M, Liu H, Chia-fon FL, Ji J (2011) Progress in the production and application of n-butanol as a biofuel. Renew Sust Energ Rev 15(8):4080–4106 Jin C, Yao M, Liu H, Chia-fon FL, Ji J (2011) Progress in the production and application of n-butanol as a biofuel. Renew Sust Energ Rev 15(8):4080–4106
3.
Zurück zum Zitat Zhang X, Deng Q, Han P, Xu J, Pan L, Wang L, Zou JJ (2017) Hydrophobic mesoporous acidic resin for hydroxyalkylation/alkylation of 2-methylfuran and ketone to high-density biofuel. AICHE J 63(2):680–688 Zhang X, Deng Q, Han P, Xu J, Pan L, Wang L, Zou JJ (2017) Hydrophobic mesoporous acidic resin for hydroxyalkylation/alkylation of 2-methylfuran and ketone to high-density biofuel. AICHE J 63(2):680–688
4.
Zurück zum Zitat Anbarasan P, Baer ZC, Sreekumar S, Gross E, Binder JB, Blanch HW, Clark DS, Toste FD (2012) Integration of chemical catalysis with extractive fermentation to produce fuels. Nature 491:235–239 Anbarasan P, Baer ZC, Sreekumar S, Gross E, Binder JB, Blanch HW, Clark DS, Toste FD (2012) Integration of chemical catalysis with extractive fermentation to produce fuels. Nature 491:235–239
5.
Zurück zum Zitat Donnelly J, Horton R, Gopalan K, Bannister CD, Chuck CJ (2015) Branched ketone biofuels as blending agents for jet-A1 aviation kerosene. Energy Fuel 30(1):294–301 Donnelly J, Horton R, Gopalan K, Bannister CD, Chuck CJ (2015) Branched ketone biofuels as blending agents for jet-A1 aviation kerosene. Energy Fuel 30(1):294–301
6.
Zurück zum Zitat Onyestyák G, Novodárszki G, Wellisch AF, Pilbath A (2016) Upgraded biofuel from alcohol–acetone feed stocks over a two-stage flow-through catalytic system. Catalysis Science & Technology 6(12):4516–4524 Onyestyák G, Novodárszki G, Wellisch AF, Pilbath A (2016) Upgraded biofuel from alcohol–acetone feed stocks over a two-stage flow-through catalytic system. Catalysis Science & Technology 6(12):4516–4524
7.
Zurück zum Zitat Kim M, Park J, Kannapu HPR, Suh YW (2017) Cross-Aldol condensation of acetone and n-butanol into aliphatic ketones over supported cu catalysts on ceria-zirconia. Catalysts 7(9):249–262 Kim M, Park J, Kannapu HPR, Suh YW (2017) Cross-Aldol condensation of acetone and n-butanol into aliphatic ketones over supported cu catalysts on ceria-zirconia. Catalysts 7(9):249–262
8.
Zurück zum Zitat Xu G, Li Q, Feng J, Liu Q, Zhang Z, Wang X, Zhang X, Mu X (2014) Direct α-alkylation of ketones with alcohols in water. ChemSusChem 7(1):105–109 Xu G, Li Q, Feng J, Liu Q, Zhang Z, Wang X, Zhang X, Mu X (2014) Direct α-alkylation of ketones with alcohols in water. ChemSusChem 7(1):105–109
9.
Zurück zum Zitat Xue C, Liu M, Guo X, Hudson EP, Chen L, Bai F, Liu F, Yang ST (2017) Bridging chemical-and bio-catalysis: high-value liquid transportation fuel production from renewable agricultural residues. Green Chem 19(3):660–669 Xue C, Liu M, Guo X, Hudson EP, Chen L, Bai F, Liu F, Yang ST (2017) Bridging chemical-and bio-catalysis: high-value liquid transportation fuel production from renewable agricultural residues. Green Chem 19(3):660–669
10.
Zurück zum Zitat Vo HT, Yeo SM, Dahnum D, Jae J, Hong CS, Lee H (2017) Pd/C-CaO-catalyzed α-alkylation and hydrodeoxygenation of an acetone-butanol-ethanol mixture for biogasoline synthesis. Chem Eng J 313:1486–1493 Vo HT, Yeo SM, Dahnum D, Jae J, Hong CS, Lee H (2017) Pd/C-CaO-catalyzed α-alkylation and hydrodeoxygenation of an acetone-butanol-ethanol mixture for biogasoline synthesis. Chem Eng J 313:1486–1493
11.
Zurück zum Zitat Reddy CB, Bharti R, Kumar S, Das P (2017) Supported palladium nanoparticle catalyzed α-alkylation of ketones using alcohols as alkylating agents. ACS Sustain Chem Eng 5(11):9683–9691 Reddy CB, Bharti R, Kumar S, Das P (2017) Supported palladium nanoparticle catalyzed α-alkylation of ketones using alcohols as alkylating agents. ACS Sustain Chem Eng 5(11):9683–9691
12.
Zurück zum Zitat Chan LK, Poole DL, Shen D, Healy MP, Donohoe TJ (2014) Rhodium-catalyzed ketone methylation using methanol under mild conditions: formation of α-branched products. Angew Chem Int Ed 53(3):761–765 Chan LK, Poole DL, Shen D, Healy MP, Donohoe TJ (2014) Rhodium-catalyzed ketone methylation using methanol under mild conditions: formation of α-branched products. Angew Chem Int Ed 53(3):761–765
13.
Zurück zum Zitat Kwon MS, Kim N, Seo SH, Park IS, Cheedrala RK, Park J (2005) Recyclable palladium catalyst for highly selective α alkylation of ketones with alcohols. Angew Chem Int Ed 44(42):6913–6915 Kwon MS, Kim N, Seo SH, Park IS, Cheedrala RK, Park J (2005) Recyclable palladium catalyst for highly selective α alkylation of ketones with alcohols. Angew Chem Int Ed 44(42):6913–6915
14.
Zurück zum Zitat Novodarszki G, Onyestyak G, Barthos R, Wellisch AF, Thakur AJ, Deka D, Valyon J (2017) Guerbet alkylation of acetone by ethanol and reduction of product alkylate to alkane over tandem nickel/mg, Al-hydrotalcite and nickel molybdate/γ-alumina catalyst systems. React Kinet Mech Catal 121(1):69–81 Novodarszki G, Onyestyak G, Barthos R, Wellisch AF, Thakur AJ, Deka D, Valyon J (2017) Guerbet alkylation of acetone by ethanol and reduction of product alkylate to alkane over tandem nickel/mg, Al-hydrotalcite and nickel molybdate/γ-alumina catalyst systems. React Kinet Mech Catal 121(1):69–81
15.
Zurück zum Zitat Novodarszki G, Onyestyak G, Wellisch AF, Pilbath A (2016) Catalytic alkylation of acetone with ethanol over Pd/carbon catalyst in flow-through system via borrowing hydrogen route. Acta Chim Slov 63(2):251–257 Novodarszki G, Onyestyak G, Wellisch AF, Pilbath A (2016) Catalytic alkylation of acetone with ethanol over Pd/carbon catalyst in flow-through system via borrowing hydrogen route. Acta Chim Slov 63(2):251–257
16.
Zurück zum Zitat Onyestyak G, Novodarszki G, Barthos R, Klebert S, Wellisch AF, Pilbath A (2015) Acetone alkylation with ethanol over multifunctional catalysts by a borrowing hydrogen strategy. RSC Adv 5(120):99502–99509 Onyestyak G, Novodarszki G, Barthos R, Klebert S, Wellisch AF, Pilbath A (2015) Acetone alkylation with ethanol over multifunctional catalysts by a borrowing hydrogen strategy. RSC Adv 5(120):99502–99509
17.
Zurück zum Zitat Jang JS, Kwon MS, Kim HG, Park JW, Lee JS (2012) Preparation and catalytic application of Pd loaded titanate nanotube: highly selective α alkylation of ketones with alcohols. Bull Kor Chem Soc 33(5):1617–1621 Jang JS, Kwon MS, Kim HG, Park JW, Lee JS (2012) Preparation and catalytic application of Pd loaded titanate nanotube: highly selective α alkylation of ketones with alcohols. Bull Kor Chem Soc 33(5):1617–1621
18.
Zurück zum Zitat Chaudhari C, Siddiki SH, Shimizu KI (2014) Self-coupling of secondary alcohols and α-alkylation of methyl ketones with secondary alcohols by Pt/CeO2 catalyst. Top Catal 57(10–13):1042–1048 Chaudhari C, Siddiki SH, Shimizu KI (2014) Self-coupling of secondary alcohols and α-alkylation of methyl ketones with secondary alcohols by Pt/CeO2 catalyst. Top Catal 57(10–13):1042–1048
19.
Zurück zum Zitat Ogawa S, Obora Y (2014) Iridium-catalyzed selective α-methylation of ketones with methanol. Chem Commun 50(19):2491–2493 Ogawa S, Obora Y (2014) Iridium-catalyzed selective α-methylation of ketones with methanol. Chem Commun 50(19):2491–2493
20.
Zurück zum Zitat Jana SK, Kubota Y, Tatsumi T (2007) Selective α-alkylation of ketones with alcohols catalyzed by highly active mesoporous Pd/MgO-Al2O3 type basic solid derived from Pd-supported MgAl-hydrotalcite. Studies in Surface Science and Catalysis 165:701–704 Jana SK, Kubota Y, Tatsumi T (2007) Selective α-alkylation of ketones with alcohols catalyzed by highly active mesoporous Pd/MgO-Al2O3 type basic solid derived from Pd-supported MgAl-hydrotalcite. Studies in Surface Science and Catalysis 165:701–704
21.
Zurück zum Zitat Devi R, Borah R, Deka RC (2014) Investigation of structural change and basicity of NaY zeolite upon loading KF and their application in henry nitroaldol reaction under microwave irradiation condition. Catal Lett 144(10):1751–1758 Devi R, Borah R, Deka RC (2014) Investigation of structural change and basicity of NaY zeolite upon loading KF and their application in henry nitroaldol reaction under microwave irradiation condition. Catal Lett 144(10):1751–1758
22.
Zurück zum Zitat Murugan C, Bajaj HC, Jasra RV (2010) Transesterification of propylene carbonate by methanol using KF/Al2O3 as an efficient base catalyst. Catal Lett 137(3–4):224–231 Murugan C, Bajaj HC, Jasra RV (2010) Transesterification of propylene carbonate by methanol using KF/Al2O3 as an efficient base catalyst. Catal Lett 137(3–4):224–231
23.
Zurück zum Zitat Khalilzadeh MA, Hosseini A, Pilevar A (2011) Potassium fluoride supported on natural nanoporous zeolite: a new solid base for the synthesis of diaryl ethers. Eur J Org Chem 2011(8):1587–1592 Khalilzadeh MA, Hosseini A, Pilevar A (2011) Potassium fluoride supported on natural nanoporous zeolite: a new solid base for the synthesis of diaryl ethers. Eur J Org Chem 2011(8):1587–1592
24.
Zurück zum Zitat Hattori H (1995) Heterogeneous basic catalysis. Chem Rev 95(3):537–558 Hattori H (1995) Heterogeneous basic catalysis. Chem Rev 95(3):537–558
25.
Zurück zum Zitat Hunger M, Schenk U, Weitkamp J (1998) Mechanistic studies of the side-chain alkylation of toluene with methanol on basic zeolites Y by multi-nuclear NMR spectroscopy. J Mol Catal A Chem 134(1–3):97–109 Hunger M, Schenk U, Weitkamp J (1998) Mechanistic studies of the side-chain alkylation of toluene with methanol on basic zeolites Y by multi-nuclear NMR spectroscopy. J Mol Catal A Chem 134(1–3):97–109
26.
Zurück zum Zitat Palomares AE, Eder-Mirth G, Rep M, Lercher JA (1998) Alkylation of toluene over basic catalysts-key requirements for side chain alkylation. J Catal 180(1):56–65 Palomares AE, Eder-Mirth G, Rep M, Lercher JA (1998) Alkylation of toluene over basic catalysts-key requirements for side chain alkylation. J Catal 180(1):56–65
27.
Zurück zum Zitat Tayade RJ, Kulkarni RG, Jasra RV (2007) Enhanced photocatalytic activity of TiO2-coated NaY and HY zeolites for the degradation of methylene blue in water. Ind Eng Chem Res 46(2):369–376 Tayade RJ, Kulkarni RG, Jasra RV (2007) Enhanced photocatalytic activity of TiO2-coated NaY and HY zeolites for the degradation of methylene blue in water. Ind Eng Chem Res 46(2):369–376
28.
Zurück zum Zitat Valyon J, Papp J, Kallo D (1981) Adsorption properties of Hungarian rhyolite tuffs containing mordenite and clinoptilolite. Acta Chimica Academiae Scientarium Hungaricae 106(2):131–146 Valyon J, Papp J, Kallo D (1981) Adsorption properties of Hungarian rhyolite tuffs containing mordenite and clinoptilolite. Acta Chimica Academiae Scientarium Hungaricae 106(2):131–146
29.
Zurück zum Zitat Kucera J, Nachtigall P (2003) Theoretical study of pyrrole interaction with alkali metal exchanged zeolites: investigation of the reliability of cluster and periodic models. Collect Czechoslov Chem Commun 68(10):1848–1860 Kucera J, Nachtigall P (2003) Theoretical study of pyrrole interaction with alkali metal exchanged zeolites: investigation of the reliability of cluster and periodic models. Collect Czechoslov Chem Commun 68(10):1848–1860
30.
Zurück zum Zitat Loveless BT, Gyanani A, Muggli DS (2008) Discrepancy between TPD-and FTIR-based measurements of Brønsted and Lewis acidity for sulfated zirconia. Appl Catal B Environ 84(3–4):591–597 Loveless BT, Gyanani A, Muggli DS (2008) Discrepancy between TPD-and FTIR-based measurements of Brønsted and Lewis acidity for sulfated zirconia. Appl Catal B Environ 84(3–4):591–597
31.
Zurück zum Zitat Huang M, Kaliaguine S (1992) Zeolite basicity characterized by pyrrole chemisorption: an infrared study. Journal of the Chemical Society Faraday Transactions 88(5):751–758 Huang M, Kaliaguine S (1992) Zeolite basicity characterized by pyrrole chemisorption: an infrared study. Journal of the Chemical Society Faraday Transactions 88(5):751–758
32.
Zurück zum Zitat Scokart PO, Rouxhet PG (1981) Characterization of the basic properties of sodium exchanged zeolites through the infrared study of pyrrole adsorption. Bulletin des Sociétés Chimiques Belges 90(9):983–984 Scokart PO, Rouxhet PG (1981) Characterization of the basic properties of sodium exchanged zeolites through the infrared study of pyrrole adsorption. Bulletin des Sociétés Chimiques Belges 90(9):983–984
33.
Zurück zum Zitat Chen WH, Pradhan A, Jong SJ, Lee TY, Wang I, Tsai TC, Liu SB (1996) Roles of carrier gases on deactivation and coking in zeolite beta during cumene disproportionation. J Catal 163(2):436–446 Chen WH, Pradhan A, Jong SJ, Lee TY, Wang I, Tsai TC, Liu SB (1996) Roles of carrier gases on deactivation and coking in zeolite beta during cumene disproportionation. J Catal 163(2):436–446
34.
Zurück zum Zitat Junke X, Wei Z, Jihui W, Zhaojing L, Jianxin MA (2009) Characterization and analysis of carbon deposited during the dry reforming of methane over Ni/La2O3/Al2O3 catalysts. Chin J Catal 30(11):1076–1084 Junke X, Wei Z, Jihui W, Zhaojing L, Jianxin MA (2009) Characterization and analysis of carbon deposited during the dry reforming of methane over Ni/La2O3/Al2O3 catalysts. Chin J Catal 30(11):1076–1084
35.
Zurück zum Zitat Aho A, Kumar N, Eränen K, Salmi T, Hupa M, Murzin DY (2008) Catalytic pyrolysis of woody biomass in a fluidized bed reactor: influence of the zeolite structure. Fuel 87(12):2493–2501 Aho A, Kumar N, Eränen K, Salmi T, Hupa M, Murzin DY (2008) Catalytic pyrolysis of woody biomass in a fluidized bed reactor: influence of the zeolite structure. Fuel 87(12):2493–2501
36.
Zurück zum Zitat Jenner G, Salem RB (2005) High pressure base-catalyzed oligomerization of ketones. High Pressure Res 25(1):1–9 Jenner G, Salem RB (2005) High pressure base-catalyzed oligomerization of ketones. High Pressure Res 25(1):1–9
37.
Zurück zum Zitat Di Cosimo JI, Apesteguıa CR (1998) Study of the catalyst deactivation in the base-catalyzed oligomerization of acetone. Journal of Molecular Catalysis A: Chemical 130:177–185 Di Cosimo JI, Apesteguıa CR (1998) Study of the catalyst deactivation in the base-catalyzed oligomerization of acetone. Journal of Molecular Catalysis A: Chemical 130:177–185
38.
Zurück zum Zitat Bleken FL, Barbera K, Bonino F, Olsbye U, Lillerud KP, Bordiga S, Beato P, Janssens TV, Svelle S (2013) Catalyst deactivation by coke formation in microporous and desilicated zeolite H-ZSM-5 during the conversion of methanol to hydrocarbons. J Catal 307:62–73 Bleken FL, Barbera K, Bonino F, Olsbye U, Lillerud KP, Bordiga S, Beato P, Janssens TV, Svelle S (2013) Catalyst deactivation by coke formation in microporous and desilicated zeolite H-ZSM-5 during the conversion of methanol to hydrocarbons. J Catal 307:62–73
39.
Zurück zum Zitat Breck DW (1976) Zeolite molecular sieves. Wiley, London Breck DW (1976) Zeolite molecular sieves. Wiley, London
40.
Zurück zum Zitat Zheng J, Zhou J, Lin H, Duan X, Williams CT, Yuan Y (2015) CO-mediated deactivation mechanism of SiO2-supported copper catalysts during dimethyl oxalate hydrogenation to ethylene glycol. J Phys Chem C 119(24):13758–13766 Zheng J, Zhou J, Lin H, Duan X, Williams CT, Yuan Y (2015) CO-mediated deactivation mechanism of SiO2-supported copper catalysts during dimethyl oxalate hydrogenation to ethylene glycol. J Phys Chem C 119(24):13758–13766
41.
Zurück zum Zitat Hu L, Yang M, Xu N, Xu J, Zhou S, Chu X, Zhao Y (2018) Selective transformation of biomass-derived 5-hydroxymethylfurfural into 2,5-dihydroxymethylfuran via catalytic transfer hydrogenation over magnetic zirconium hydroxides. Korean J Chem Eng 35(1):99–109 Hu L, Yang M, Xu N, Xu J, Zhou S, Chu X, Zhao Y (2018) Selective transformation of biomass-derived 5-hydroxymethylfurfural into 2,5-dihydroxymethylfuran via catalytic transfer hydrogenation over magnetic zirconium hydroxides. Korean J Chem Eng 35(1):99–109
42.
Zurück zum Zitat Shen Z, Jin F, Zhang Y, Wu B, Cao J (2009) Hydrogen transfer reduction of ketones using formic acid as a hydrogen donor under hydrothermal conditions. Journal of Zhejiang University SCIENCE A10(11):1631–1635 Shen Z, Jin F, Zhang Y, Wu B, Cao J (2009) Hydrogen transfer reduction of ketones using formic acid as a hydrogen donor under hydrothermal conditions. Journal of Zhejiang University SCIENCE A10(11):1631–1635
43.
Zurück zum Zitat Shen Z, Zhang Y, Jin F, Zhou X, Kishita A, Tohji K (2010) Hydrogen-transfer reduction of ketones into corresponding alcohols using formic acid as a hydrogen donor without a metal catalyst in high-temperature water. Ind Eng Chem Res 49(13):6255–6259 Shen Z, Zhang Y, Jin F, Zhou X, Kishita A, Tohji K (2010) Hydrogen-transfer reduction of ketones into corresponding alcohols using formic acid as a hydrogen donor without a metal catalyst in high-temperature water. Ind Eng Chem Res 49(13):6255–6259
44.
Zurück zum Zitat Chen GW, Li SL, Jiao FJ, Yuan Q (2007) Catalytic dehydration of bioethanol to ethylene over TiO2/γ-Al2O3 catalysts in microchannel reactors. Catal Today 125:111–119 Chen GW, Li SL, Jiao FJ, Yuan Q (2007) Catalytic dehydration of bioethanol to ethylene over TiO2/γ-Al2O3 catalysts in microchannel reactors. Catal Today 125:111–119
45.
Zurück zum Zitat Kochar NK, Merims R, Padia AS (1981) Ethylene from ethanol. Chem. Eng. Process 77:66–70 Kochar NK, Merims R, Padia AS (1981) Ethylene from ethanol. Chem. Eng. Process 77:66–70
46.
Zurück zum Zitat Scott Fogler H (2004) Elements of chemical reaction engineering, 3rd edn. Prentice-Hall of India Private Limited, New Delhi Scott Fogler H (2004) Elements of chemical reaction engineering, 3rd edn. Prentice-Hall of India Private Limited, New Delhi
Metadaten
Titel
Conversion of biorenewably available acetone and butanol to liquid fuels using base catalysts
verfasst von
Tarun Pratap Singh Jadon
Arun Kumar Jana
Parimal A. Parikh
Publikationsdatum
02.01.2020
Verlag
Springer Berlin Heidelberg
Erschienen in
Biomass Conversion and Biorefinery / Ausgabe 5/2021
Print ISSN: 2190-6815
Elektronische ISSN: 2190-6823
DOI
https://doi.org/10.1007/s13399-019-00563-6

Weitere Artikel der Ausgabe 5/2021

Biomass Conversion and Biorefinery 5/2021 Zur Ausgabe