Mild hydrogenation of simulated bio-oil based on molecular distillation
- Corresponding author: WANG Shu-rong, zzk@zjut.edu.cn
Citation:
CHEN Jun-hao, LU Liang, WANG Shu-rong. Mild hydrogenation of simulated bio-oil based on molecular distillation[J]. Journal of Fuel Chemistry and Technology,
;2017, 45(9): 1056-1063.
CZERNIK S, BRIDGWATER A V. Overview of applications of biomass fast pyrolysis oil[J]. Energy Fuels, 2004,18(2):590-598. doi: 10.1021/ef034067u
WANG Qi, LIU Qian, HE Bo, WANG Shu-rong, LUO Zhong-yang, CEN Ke-fa. Experimental research on biomass flash pyrolysis for bio-oil in a fluidized bed reactor[J]. J Eng Thermophys, 2008,29(5):885-888.
ZHANG Q, CHANG J, WANG T J, XU Y. Review of biomass pyrolysis oil properties and upgrading research[J]. Energy Convers Manage, 2007,48(1):87-92. doi: 10.1016/j.enconman.2006.05.010
XIU S, SHAHBAZI A. Bio-oil production and upgrading research:A review[J]. Renewable Sustainable Energy Rev, 2012,16(7):4406-4414. doi: 10.1016/j.rser.2012.04.028
GUO Xiao-ya, YAN Yong-jie. Catalytic cracking of biomass fast pyrolysis oil[J]. Chem React Eng Technol, 2005,21(3):227-233.
CHEN Jiao-jiao, CHEN Guan-yi, MA Wen-chao, MA Long-long, WANG Tie-jun, ZHANG Qi, LÜ Wei. Experimental study of aromatics production from catalytic cracking of bio-oil model compounds[J]. J Fuel Chem Technol, 2013,41(2):183-188.
GAYUBO A G, AGUAYO A T, ATUTXA A, AGUADO R, BILBAO J. Transformation of oxygenate components of biomass pyrolysis oil on a HZSM-5 zeolite. I. Alcohols and phenols[J]. Ind Eng Chem Res, 2004,43(11):2610-2618. doi: 10.1021/ie030791o
GAYUBO A G, AGUAYO A T, ATUTXA A, AGUADO R, OLAZAR M, BILBAO J. Transformation of oxygenate components of biomass pyrolysis oil on a HZSM-5 zeolite.Ⅱ. Aldehydes, ketones, and acids[J]. Ind Eng Chem Res, 2004,43(11):2619-2626. doi: 10.1021/ie030792g
CARLSON T R, JAE J, LIN Y C, TOMPSETT G A, HUBER G W. Catalytic fast pyrolysis of glucose with HZSM-5:The combined homogeneous and heterogeneous reactions[J]. J Catal, 2010,270(1):110-124. doi: 10.1016/j.jcat.2009.12.013
WANG Yu-rong, WANG Shu-rong, WANG Xiang-yu, GUO Zuo-gang. Molecular distillation separation characteristic of bio-oil under different pressures[J]. J Fuel Chem Technol, 2013,41(2):177-182.
GUO Z G, WANG S R, GU Y L, XU G H, LI X, LUO Z Y. Separation characteristics of biomass pyrolysis oil in molecular distillation[J]. Sep Purif Technol, 2010,76(1):52-57. doi: 10.1016/j.seppur.2010.09.019
MENTZEL U V, HOLM M S. Utilization of biomass:Conversion of model compounds to hydrocarbons over zeolite H-ZSM-5[J]. Appl Catal A, 2011,396(1/2):59-67.
WANG S R, CAI Q J, WANG X Y, ZHANG L, WANG Y R, LUO Z Y. Biogasoline production from the Co-cracking of the distilled fraction of bio-oil and ethanol[J]. Energy Fuels, 2014,28(1):115-122. doi: 10.1021/ef4012615
WANG S R, CAI Q J, WANG X Y, ZHANG L, WANG Y R, LUO Z Y. Biogasoline production by co-cracking of model compound mixture of bio-oil and ethanol over HSZM-5[J]. Chin J Catal, 2014,35(5):709-722. doi: 10.1016/S1872-2067(14)60046-2
WANG S R, CAI Q J, CHEN J H, ZHANG L, WANG X Y, YU C J. Green aromatic hydrocarbon production from cocracking of a bio-oil model compound mixture and ethanol over Ga2O3/HZSM-5[J]. Ind Eng Chem Res, 2014,53(36):13935-13944. doi: 10.1021/ie5024029
WANG S R, CAI Q J, CHEN J H, ZHANG L, ZHU L J, LUO Z Y. Co-cracking of bio-oil model compound mixtures and ethanol over different metal oxide-modified HZSM-5 catalysts[J]. Fuel, 2015,160:534-543. doi: 10.1016/j.fuel.2015.08.011
VENDERBOSCH R H, ARDIYANTI A R, WILDSCHUT J, OASMAA A, HEERES H J. Stabilization of biomass-derived pyrolysis oils[J]. J Chem Technol Biotechnol, 2010,85(5):674-686. doi: 10.1002/jctb.v85:5
WILDSCHUT J, MAHFUD F H, VENDERBOSCH R H, HEERES H J. Hydrotreatment of fast pyrolysis oil using heterogeneous noble-metal catalysts[J]. Ind Eng Chem Res, 2009,48(23):10324-10334. doi: 10.1021/ie9006003
ARDIYANTI A R, GUTIERREZ A, HONKELA M L, KRAUSE A O I, HEERES H J. Hydrotreatment of wood-based pyrolysis oil using zirconia-supported mono-and bimetallic (Pt, Pd, Rh) catalysts[J]. Appl Catal A, 2011,407(1/2):56-66.
ELLIOTT D C, HART T R. Catalytic hydroprocessing of chemical models for bio-oil[J]. Energy Fuels, 2009,23(2):631-637. doi: 10.1021/ef8007773
CHEN J H, CAI Q J, LU L, LENG F R, WANG S R. Upgrading of the acid-rich fraction of bio-oil by catalytic hydrogenation-esterification[J]. ACS Sustainable Chem Eng, 2016,5(1):1073-1081.
YAO Yan, WANG Shu-rong, LUO Zhong-yang, CEN Ke-fa. Experimental research on catalytic hydrogenation of light fraction of bio-oil[J]. J Eng Thermophys, 2008,29(4):715-719.
YU W J, TANG Y, MO L Y, CHEN P, LOU H, ZHENG X M. One-step hydrogenation-esterification of furfural and acetic acid over bifunctional Pd catalysts for bio-oil upgrading[J]. Bioresour Technol, 2011,102(17):8241-8246. doi: 10.1016/j.biortech.2011.06.015
YU WJ, TANG Y, MO L Y, CHEN P, LOU H, ZHENG X M. Bifunctional Pd/Al-SBA-15 catalyzed one-step hydrogenation-esterification of furfural and acetic acid:A model reaction for catalytic upgrading of bio-oil[J]. Catal Commun, 2011,13(1):35-39. doi: 10.1016/j.catcom.2011.06.004
ZHONG Wei-cheng, GUO Qing-jie, WANG Xu-yun, ZHANG Liang. Catalytic hydroprocessing of fast pyrolysis bio-oil from Chlorella[J]. J Fuel Chem Technol, 2013,41(5):571-578.
ELLIOTT D C. Historical Developments in Hydroprocessing Bio-oils[J]. Energy Fuels, 2007,21(3):1792-1815. doi: 10.1021/ef070044u
WEI Hong-ge, ZHONG Zhao-ping, LI Rui, JIN Li-wei. Research on solid catalysts base hydrogenation for bio-oil model compounds[J]. Renewable Energy Resour, 2010,28(1):52-62.
ZHAO H Y, LI D, BUI P, OYAMA S T. Hydrodeoxygenation of guaiacol as model compound for pyrolysis oil on transition metal phosphide hydroprocessing Catalysts[J]. Appl Catal A, 2011,391(1/2):305-310.
VISPUTE T P, ZHANG H Y, SANNA A, XIAO R, HUBER G W. Renewable chemical commodity feedstocks from integrated catalytic processing of pyrolysis oils[J]. Science, 2010,330(6008):1222-1227. doi: 10.1126/science.1194218
BECK A, HORVATH A, SZUCS A, SCHAY Z, HORVATH Z E, ZSOLDOS Z, DEKANY I, GUCZI L. Pd nanoparticles prepared by "controlled colloidal synthesis" in solid/liquid interfacial layer on silica. I. Particle size regulation by reduction time[J]. Catal Lett, 2000,65(1/3):33-42. doi: 10.1023/A:1019048701152
LI B, WENG W Z, ZHANG Q, WANG Z W, WAN H L. Sinter-resistant Pd/SiO2 nanocatalyst prepared by impregnation method[J]. ChemCatChem, 2011,3(8):1277-1280. doi: 10.1002/cctc.201100043
GRANGE P, LAURENT E, MAGGI R, CENTENO A, DELMON B. Hydrotreatment of pyrolysis oils from biomass:Reactivity of the various categories of oxygenated compounds and preliminary techno-economical study[J]. Catal Today, 1996,29(1/4):297-301.
LI Qi-yi, WAN Lei, ZHANG Su-ping, XU Qing-li, YAN Yong-jie. Hydrodeoxygenation of bio-oil under mild conditions[J]. Petrochem Technol, 2011,40(9):954-958.
KREUZER K, KRAMER R. Support effects in the hydrogenolysis of tetrahydrofuran on platinum catalysts[J]. J Catal, 1997,167(2):391-399. doi: 10.1006/jcat.1997.1608
ZHAO C, HE J Y, LEMONIDOU A A, LI X B, LERCHER J A. Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes[J]. J Catal, 2011,280(1):8-16. doi: 10.1016/j.jcat.2011.02.001
SHAFAGHAT H, REZAEI P S, DAUD W M A W. Catalytic hydrogenation of phenol, cresol and guaiacol over physically mixed catalysts of Pd/C and zeolite solid acids[J]. RSC Adv, 2015,5(43):33990-33998. doi: 10.1039/C5RA00367A
ADJAYE J D, BAKHSHI N N. Catalytic conversion of a biomass-derived oil to fuels and chemicals Ⅰ:Model compound studies and reaction pathways[J]. Biomass Bioenergy, 1995,8(3):131-149. doi: 10.1016/0961-9534(95)00018-3
NI Y M, PENG W Y, SUN A M, MO W L, HU J L, LI T, LI G X. High selective and stable performance of catalytic aromatization of alcohols and ethers over La/Zn/HZSM-5 catalysts[J]. J Ind Eng Chem, 2010,16(4):503-505. doi: 10.1016/j.jiec.2010.03.011
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(a): the effect of reaction pressure (200℃); (b): the effect of reaction temperature (4MPa)
a: 2MPa; b: 3MPa; c: 4MPa