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Frontiers in Energy

ISSN 2095-1701

ISSN 2095-1698(Online)

CN 11-6017/TK

邮发代号 80-972

2019 Impact Factor: 2.657

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Frontiers in Energy  2024, Vol. 18 Issue (5): 550-582   https://doi.org/10.1007/s11708-024-0943-7
  本期目录
Catalytic hydrodeoxygenation of pyrolysis bio-oil to jet fuel: A review
Zhongyang Luo(), Wanchen Zhu, Feiting Miao, Jinsong Zhou
State Key Laboratory of Clean Energy Utilization, Zhejiang University, Hangzhou 310027, China
 全文: PDF(10153 KB)   HTML
Abstract：

Bio-oil from biomass pyrolysis cannot directly substitute traditional fuel due to compositional deficiencies. Catalytic hydrodeoxygenation (HDO) is the critical and efficient step to upgrade crude bio-oil to high-quality bio-jet fuel by lowering the oxygen content and increasing the heating value. However, the hydrocracking reaction tends to reduce the liquid yield and increase the gas yield, causing carbon loss and producing hydrocarbons with a short carbon-chain. To obtain high-yield bio-jet fuel, the elucidation of the conversion process of biomass catalytic HDO is important in providing guidance for metal catalyst design and optimization of reaction conditions. Considering the complexity of crude bio-oil, this review aimed to investigate the catalytic HDO pathways with model compounds that present typical bio-oil components. First, it provided a comprehensive summary of the impact of physical and electronic structures of both noble and non-noble metals that include monometallic and bimetallic supported catalysts on regulating the conversion pathways and resulting product selectivity. The subsequent first principle calculations further corroborated reaction pathways of model compounds in atom-level on different catalyst surfaces with the experiments above and illustrated the favored C–O/C=O scission orders thermodynamically and kinetically. Then, it discussed hydrogenation effects of different H-donors (such as hydrogen and methane) and catalysts deactivation for economical and industrial consideration. Based on the descriptions above and recent researches, it also elaborated on catalytic HDO of biomass and bio-oil with multi-functional catalysts. Finally, it presented the challenges and future prospective of biomass catalytic HDO.
Key words： biomass pyrolysis oil    bio-jet fuel    catalytic hydrodeoxygenation (HDO)    metal catalyst    reaction pathways
收稿日期: 2024-01-20      出版日期: 2024-10-16
Corresponding Author(s): Zhongyang Luo   
 引用本文:   
. [J]. Frontiers in Energy, 2024, 18(5): 550-582.
Zhongyang Luo, Wanchen Zhu, Feiting Miao, Jinsong Zhou. Catalytic hydrodeoxygenation of pyrolysis bio-oil to jet fuel: A review. Front. Energy, 2024, 18(5): 550-582.
 链接本文:  
https://academic.hep.com.cn/fie/CN/10.1007/s11708-024-0943-7
https://academic.hep.com.cn/fie/CN/Y2024/V18/I5/550
Fig.1  
Catalyst Feedstock T/°C P/MPa t/h Reaction Products Conv./% Select./% Y/% Ref.
Pt/(Al)-SBA-15 Anisole 200 2 6 Ring HYD and DMO CHA – 92 – Shivhare et al. [35]
Pt/WO3–x VAN 220 4 2 Hydrogen spillover MCH > 99 92.5 – Sun et al. [34]
Pd/ZrO2Pd/TiO2Pd/Nb2O5 GUA 300 0.1 – Dehydroxylation, DMO, DME Benzene and cyclohexanone 11.1–25 13.4–15.7 – Teles et al. [36]
Ru/SBA-15 Phenol 80 2 4 HYD, DMO COL > 99.9 > 99.9 – Feng et al. [37]
Pd/CPt/CRu/CRu/CeO2 GUA 200 1 5 HYD, etheric C–O(R) cleavage COLs 100 100 – Zhang et al. [38]
Pd/CHZSM-5 5-HMF 240 8 – C–C oxidative coupling Bicyclohexane 99.3 90.4 87.4 Cai et al. [39]
SO42−/TiO2,Pd/NbOPO4 2-methylfuran, furfural 80, 180–210 3–6 – Hydroxyalkylation/alkylation, HDO Long-chain alkanes – – 85.0 Yan et al. [40]
Pd-PTA/ZrO2 VAN 80 0.1 1.5 HYD, hydrogenolysis MMP 99 99 – Gao et al. [41]
SAC Pt/Co2AlO4 5-HMF 180 2 3 Activation adsorption of C=O bond, C–O bond dissociation 2,5-DMF – – 99 Wang et al. [42]
Tab.1  
Fig.2  
Catalyst Feedstock T/°C P/MPa t Reaction Product Conv./% Select./% Y/% Ref.
Co/CeO2 Prot lignin 300 0.1 20 s DMO, HYD Aromatic hydrocarbons – – 46.8 Kumar et al. [47]
Co/γ-Al2O3Fe/γ-Al2O3 Saccharina japonica pyrolyzed bio-oil 350 1.5 1 h Decarboxylation and DME C12–14 kerosene-diesel fraction – – 38.62–48.92 wt.% Ly et al. [45]
Co/C@N benzyl phenyl ether 200 2 1 h Selective hydrogenolysis COL 100 98.2 – Song et al. [46]
Ni/ZSM-5Cu/ZrO2 Propionic acid, furfural, phenol, acetaldehyde and acetone 350 6 3 h Ketonization, HYD, aldol condensation, C–C coupling. C7–18 jet-fuel precursors 60.3–99.5 77.1max – Sun et al. [30]
Ni/ZSM-5 Catechol 200 3 2 h Hydrogenolysis, ring HYD Cyclohexane-1,2-diol 100 – 89 Song et al. [48]
Cu/γ-Al2O3 Anisole 500 0.8 3.28 h−1 DMO Benzene 80 47 – Saidi et al. [49]
Fe/HBetaFe/ZrO2 Kraft lignin, phenol compounds 350 0.1 – Dehydration, hydrogenolysis Aromatic hydrocarbons – – 7.1 wt.% Sirous-Rezaei et al. [50]
Fe/ZrO2 Etek lignin 600 0.1 30 s HYD, methanation BTX – 67 34 Lonchay et al. [51]
Zn/HY m-cresol 250 0.1 2.8 h−1 Alkylation Thymol 92 71 – Afreen et al. [52]
Ni/TiO2 Furfural 160 2 6 h HYD FA 98 83 82 Zhang et al. [53]
MoO3/ZSM-5 Lignin (main), phenolics 600 0.1 – DMO, ring alkylation Hydrocarbons – 92 42.24 C% (carbon yield) Xue et al. [54]
Ni/Beta Biocrude oil 330 4 3.3 h Selectively HYD Hydrocarbons – – 15.7 wt.% Yan et al. [55]
Tab.2  
Fig.3  
Catalyst Feedstock T/°C P/MPa t/h Reactions Product Conv./% Select./% Y/wt.% Ref.
Pt/NbOPO4 Raw woods 190 5 20 Hydrogenolysis, alkylation CHA – – 28.1 Xia et al. [70]
RuCoNx/NC 4-propylGUA 280 1 6 Hydrogen spillover 4-propylcyclohexane 100 95 – Zhao et al. [71]
Pd-Cu/ZrO2Pd-Zn/ZrO2 Phenol 300 0.1 120 h−1 Dehydrogenation/ dehydroxylation Cyclohexanone 13.54, 7.74 74.91, 80.36 – Resende et al. [72]
Pd-Ni/HZSM-5 Diphenyl either 220 2 2 Hydrogenolysis, dihydroxylation, HYD CHA 99.9 100 – Zhao et al. [73]
RuCo/SiO2-ZrO2 GUA 260 1 4 HYD, C–C coupling Hydrocarbons 59.9 56 – Shu et al. [74]
Ru-Cu/HY Lignin 250 4 2 Hydrogenolysis, dimerization, ring opening Hydrocarbons 99 – 62 Wang et al. [31]
RuFe/Al2O3-EG GUA 240 3 4 Hydrogenolysis of C–OMe, HYD COL 99 81.35 – Liu et al. [75]
PdNi/CuFe2O4 VAN 180 2 2 DMO, ring reduction 4-methyl COL 99.6 95.8 – Sunil More et al. [76]
RuNi/SiO2-ZrO2 GUA 260 1 4 HYD, deoxygenation CHA 99.9 100 – Li et al. [77]
Pd-Ni/AC VAN 90 1 2 Hydrogenolysis Aldehydes 100 99 – Zhang et al. [78]
Tab.3  
Fig.4  
Catalyst Feedstock T/°C P/MPa t/h Reactions Product Conv./% Select./% Y/wt.% Ref.
NiCo/Al2O3-MgO GUA 300 2 1 DMO, DME, HYD COL 100 80.7 – He et al. [87]
NiMo/γ-Al2O3 Poplar 350 1.5 – HDO Aliphatics – 72.6 6.4 Miao et al. [88]
NiCu/SiO2 Anisole 280 6 – DMO, HYD CHA 100 45 – Khromova et al. [89]
CoNi/Al2O3 VAN 200 1 1 HYD, dehydroxylation MethylCOL 100 100 – Liu et al. [90]
NiCo/GO (graphite oxide) GUA 300 5 4 DDO, HYD COL 100 78 – Blanco et al. [91]
NiFe nanocatalysts GUA 230 1 1 Caryl–OR cleavage, HYD CHA 100 70.5 – Zhang et al. [92]
MoOx-NiMo/NC (-Al2O3) GUA 230 3 1 DMO, HYD, dehydroxylation CHA 100 98.3 – Zhang et al. [93]
NiFe/MCSs Phenol 250 5 10 HYD, hydrogenolysis CHA > 99 49.9 – Han et al. [94]
NiCo/MCM-41-H Jatropha oil 360 3 5 HDO C12–C18 alkanes – 98.2 65.8 (biofuel) Lei et al. [95]
NiCu/TiO2 Furfural 200 0.1 0.87 h–1 Dehydroxylation 2-methylfuran > 99 84.5 – Jaswal et al. [96]
Tab.4  
Fig.5  
Catalytic surfaces Reactants Products Major step Adsorption/eV Ref.
Ptsub-Fe(211)Ptads-Fe(211) Phenolo-cresolGUA BenzeneToluenephenol Horizontal adsorption; Caryl–O activation −1.09/−1.06−0.99/−0.94−0.89/−0.88 Li et al. [100]
Ni(111)NiFe(111)FeOx-Ni(111) GUA CHA Caryl–OCH3 activation on FeOx −2.52−1.95−2.19 Zhang et al. [92]
Ru-CeO2(100) Aromatic compounds COLs Ru–O–Ce sites promoted etheric C–O(R) bond − Zhang et al. [38]
Ru(0001)Co(0001)RuCo(0001) GUA Hydrocarbons Electrons transfer from Ru to Co enhanced Caryl–OCH3 activation −2.83−1.80−4.85 Shu et al. [74]
NiFe(111)PtFe(111) GUA Anisole Caryl–O on NiFe surface and H-addition of benzene ring on PtFe surface −1.82−1.39 Liu et al. [101]
Cu(111) GUA Catechol, anisole Rate-limiting step barrier of catechol is 1.97 eV, and that of anisole is 2.07 eV −1.90 Konadu et al. [102]
Pd(111) GUA Cyclohexanone CTH reaction was affected by H-donor, the threshold step of bicyclohexyl is the elimination of the fourth H (0.2 eV), and that of cyclohexylbenzene is the removal of the first H (0.01 eV) − Fraga et al. [103]
PdNi/CuFe2O4 VAN 4-mehtyl COL DMO (−170 kJ/mol) −2.94 Sunil More et al. [76]
Ru(0001) Phenol COL Direct HYD of COL (1.51 eV) addition of H on α-carbon of cyclohexanone (1.13 eV) −1.51 Gao et al. [104]
M@Ni(111), M=Fe, V, Mo, W, Re Phenol Benzene, CHA OH* binding −0.98, −1.32, −1.25, −1.22, −1.07−1.05, −1.16, −1.12, −1.09, −1.07 Zhou et al. [105]
(Pd-doped)Fe(211)Fe(110)Fe(111) Phenol CHA Direct ring HYD −0.93−1.06−1.00 Nie et al. [106]
Mo3O5/Ni(111) Phenol Benzene Dehydroxylation is rate-limiting step, and the barrier is 0.95 on Mo3O5/Ni −1.86 Wu et al. [107]
MoOx/SBA-15 Phenolics Benzene Activation energy of Caryl–OR and Caryl–OH were 48.57 and 24.68 kJ/mol − Tan et al. [108]
M-MoO3–x/TiO2, M = Pt, Ni, Cu P-cresol Methyl cyclohexane H2 activation on Pt was barrierless and reaction energy is −1.55 eV Metal adsorption−3.16−6.50−5.32 Itthibenchapong et al. [109]
Ru(0001) GUA CHA Cis-isomer (1R, 2S)-2-methoxyCOL formation −1.12 Khan et al. [110]
Ni3/4/5M1, Msurf-alloy/Ni(111), M = Fe, W, Mo GUA CHA DDO of cresol to toluene − Yan et al. [111]
M@Pt(211), M=Co, Fe, Mo Phenolics Benzene Dehydroxylation through M−O (phenol) −0.96−0.97−1.38 Liu et al. [112]
Tab.5  
Fig.6  
Fig.7  
Catalytic surface Reactant Product Major step Adsorption/eV Ref.
Co(111)Fe(110)Ir(111)Ni(111)Pd(111)Pt(111)Rh(111)Ru(001) Furan Hydrocarbons CHx–OHy scission barrier −0.70−0.75−1.15−0.37−0.76−1.18−1.03−0.97 Kanchan & Banerjee [119]
Cu(111)Cu2O(111)Cu3Ni1(111)Cu1Ni3(111) Furfural Tetrahydrofurfuryl alcohol HYD of furan ring on Cu+ RPBE−0.91−1.65−1.18−1.99 Fang & Liu [120]
Mo1/Ni(111)Mo2/Ni(111)MoNi(111) Furfural 2-MF The rate-determining steps on Mo1/Ni for H and OH path were first HYD (1.27 eV) and H2O dissociation (1.13 eV), on Mo2/Ni were H2O formation (1.61 eV) and O* HYD (1.23 eV), on MoNi were H2O formation (1.59 eV) and OH regeneration (1.83 eV) −2.41−2.62−2.89 Chen et al. [121]
Co(110)CoOx(110) Furfural 2-MF Formyl group adsorbed on Co0 and C–O adsorbed on CoOx −0.731.61 Zhang et al. [122]
NiH_CeO2(111)NiHOH_CeO2(111) Levoglucosan Aliphatic compounds H transfer to ether bridge and water ejection were rate-determining steps − Hamid et al. [123]
Dimeric Mo/TiO2(101) 1,4-anhydroerythritol Tetrahydrofuran MoIV–MoV and MoV–MoV presented low energy barrier (~1.0 eV) of C–O bond cleavage relatively − Asada et al. [124]
Ru(001) Furfural MF C–O scission on ring (64 kJ/mol) and HYD of carbon atom on formyl group (81 kJ/mol) were preferred −0.96 Banerjee & Mushrif [125]
Pt(111) Dibenzofuran Bicyclohexane Intermediate tetrahydrodibenzofuran partly determined deoxygenation reaction −1.93 Wang et al. [126]
Ni/MgO(111) Furfural Furan Rate-determining step was dehydrogenation of carbon atom on carbonyl group (2.02 eV) −0.43 Chen et al. [127]
Cu4/MgO(111) Furfural FA C=O bond adsorbed down on the Cu+ (−4.78 eV). The rate-limiting step was *CHO hydrogenated to *CHOH (0.98 eV) −4.70 Zhang et al. [128]
Pd(111)Pd3-Fe1(111)Pd2-Fe2(111) Furfural 2-MF Pd-Fe alloy weaken the ring HYD while Fe enhanced C=O HYD and C–O cleavage −0.87−0.75−0.73 Pino et al. [129]
Ni(111)Re Ox/Ni(111) Furfural Tetrahydrofurfuryl a lcohol Adsorption energy of FA was higher on ReOx/Ni(111) (−2.19 eV vs. −1.89 eV), but H2 activation barrier was lower on Ni (111) (0.39 eV vs. 1.43 eV) −1.89−2.04 Lin et al. [130]
Cu38Cu(111) Furfural 2-MF Dissociation of isopropanol was −0.23 and 0.09 eV, respectively. Thus, Cu38 clusters promoted hydrogenolysis of isopropanol −0.70−0.72 Luo et al. [131]
Cu3Co1(111) Furfural FA H2 adsorption was highest on Cu3Co1 (−2.66 eV), while H* was lowest (−0.61 eV) −5.51 Zhao et al. [132]
Pd6/Co(101) Furfural Cyclopentanone/ cyclopentanol Electron transfer from Pd to Co resulted in the downshift of d-band center of Co, facilitating H desorption (3.7 eV) −1.40 Yuan et al. [133]
Tab.6  
Fig.8  
Fig.9  
Catalysts Feedstock T/°C P/MPa t/h Product Main sites Conv./% Select./% Y Ref.
Pd/h-BN Aldehydes/ketones 60 0.1 1 Alcohols N vacancies, Pd sites 100 100 – Zhang et al. [140]
Ru/TiO2 GUA 100 5 1 2-methoxyCOL Ru NPs ~92 80–100 – Kim et al. [141]
Pt/CeO2-ZrO2 Carbonyl compounds 20 0.1 2 Alcohols Ce3+, defects on ZrO2 96 70–99 – Redina et al. [142]
Pd-CuO/CeO2 Phenols 90 1 5 COL Ov on metal oxide, Pd0 99 88 – Kasabe et. [143]
Ni5 Fe1/CNT GUA 300 3 6 h−1 CHA Fe2+, Fe0, Ni0 96.8 83.4 – Yung et al. [144]
Pd/H-Nb2O5 phenol 350 0.1 – Benzene Pd cluster, Ov 100 74.2 – Rong et al. [145]
NiRu/TiO2 Anisole 300 4 4 CHA Ti3+, Ni0 59.5 46.5 – Rios-Escobedo et al. [146]
FePt/SiO2 Furfural 300 0.1 3 h−1 2-MF Fe–Pt alloy – 64.3 40.6% Zanuttini et al. [147]
PtNi/ZSM-5 Anisole 200 3 3.5 CHA Pd0, Ni0,2+ 99.1 – 90 wt.% Guo et al. [148]
Pt/TiO2 m-cresol 350 0.1 0.5 Toluene Pt–Ov–Ti3+ > 90 > 90 – Wu et al. [149]
Tab.7  
Fig.10  
Catalyst Feedstock T/°C P/MPa t/h Product Main site Conv./% Select./% Y Ref.
Ga/HZSM-5 Poplar 550 0.1 – BTEX (GaO)+ – – 9.58 wt.% Moogi et al. [159]
Zn–Mo/HZSM-5 Food waste 550 0.1 – BTEX Zn–Mo alloy – – 19.93 wt.% Moogi et al. [160]
Zn–Cu–Ga/ZSM-5 Glycerol 400 0.5 – Alkyl aromatics Cu1+, Br?nsted acid sites 100 > 70 – Austin et al. [161]
Zn-Cr/ZSM-5 Xylose 400 1 1 Aromatics Lewis acid sites on Zn–Cr – 63.1 (BTEX) 57.6% Peng et al. [162]
ZSM-5 Olefins and furanic compound 600 0.1 5.7 h−1 BTX Diels-Alder condensation on acid sites 84 80.4 – Cheng & Huber [163]
Zn/ZSM-5 Pyrolysis oil 300–600 0.1 3600 h−1 GHSV Upgraded oil ZnO particles (< 10 nm) – – 9.84 wt.% He et al. [164]
Zn–Ga/ZSM-5 Furfural 400 2.5 1 BTX Zn2+, Ga3+ – 71.4 (aromatics) 68.4 C% Wang et al. [165]
MoZn/HZSM-5 Red cedar 650 0.1 – Bio-oil Mo–Zn alloy – 16.5 53.4 Tshikesho et al. [166]
Tab.8  
Fig.11  
Catalyst Feedstock T/°C P/MPa Cycles Reasons for (in)stability Ref.
PtRu/HZSM-5 4-propylphenol 110 0.1 4 Hierarchical structure of HZSM-5 Salakhum et al. [81]
Ru/Zn@Beta Kraft lignin 290 0.8 5 Carbonaceous deposition reduced yield to 88% Zhu et al. [68]
NiCo/MCM-41 Jatropha oil 360 3 5 H2 pretreatment reduced coke formation Lei et al. [95]
PdRu/HAP-ZrP Lignocellulose-derived C15 oxygenate 150 4 5 Unstable oligomers covered over the active sites Li [69]
CoFe/AC Bio-oils from wood pallet sawdust 350 6 Surface area and pore volumes decreased Carbonaceous compounds on the external surface Khanh Tran et al. [190]
Pt/HBEA Pine pyrolysis vapors 500 0.1 Surface area and pore volumes decreased Polyaromatic hydrocarbons transformed into coke Yung et al. [144]
NiMo/HZSM-5 Arundo donax 400 3.45 Surface area reduced Coke formation Chandler et al. [83]
PtNi@HZ Anisole and GUA 150, 200 3 5 Metal loss or aggregation Tian et al. [191]
PdNi/HZSM-5 Diphenyl ether 220 2 4 Metal agglomeration reduced conversion to 32.8% Zhao [73]
PdNi/AC VAN 90 0.2 8 Metal aggregation Li et al. [77]
Ru-ZnO/SBA-15 lignin 220 2 4 Metal aggregation and sites blocked Chen et al. [192]
NiFe/MCSs Lignin-derived phenols 250 5 4 Metal loss Han et al. [94]
PdM/ZrO2 (M = Cu, Ag, Zn, Sn) Phenol 300 0.1 24 h continuously Pd sintering Resende et al. [72]
Tab.9  
Fig.12  
2,5-DMF 2,5-dimethylfuran
4-MP 4-methylphenol
5-HMF 5-hydroxymethylfurfural
5-MFA 5-methylfurfuryl alcohol
5-MFF 5-methylfurfural
BTEX Benzene, toluene, ethylbenzene and xylenes
CHA Cyclohexane
CTH Catalytic transfer hydrogenaration
DCO Decarboxylation and/or decarbonylation
DDO Direct deoxygenation
DFT Density functional theory
DME Demethylation
DMO Demethoxylation
FA Furfuryl alcohol
FF Furfrual
H/C Hydrogen to carbon ratio
HAD Hydroxyalkylation
HCR Hydrocracking
HDO Hydrodeoxygenation
HHV Higher heating value
HYD Hydrogenation
MCH Methylcyclohexane
MF Methylfuran
MMP 2-methoxy-4-methylphenol
MTHF Methyltetrahydrofuran
Ov Oxygen vacancy
THFA Tetrahydrofurfuryl alcohol
  
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