MPa H2 Pressure Research Articles

Furfural hydrogenation to 2‐methylfuran over efficient sol‐gel copper‐cobalt/zirconia catalyst

Abstract2‐Methylfuran (MF) is a candidate to be a high‐quality fuel additive. For the first time, efficient Co‐Cu/ZrO2 catalysts were prepared by the sol‐gel method and herein used for MF synthesis from furfural. Although a 9.2% MF yield and no MF was obtained using Cu/ZrO2 and Co/ZrO2, respectively, a 77.5% MF yield was observed at 200°C, under 1.5 MPa initial H2 pressure for 4 hours using a Co‐Cu/ZrO2 catalyst. The Co amount was changed in the catalyst structure and the effect of the Co amount on furfural hydrogenation was investigated. The most effective catalyst was the Co‐Cu/ZrO2 catalyst, with 0.08 g/g (8 mass%) Cu and 0.118 g/g (11.8 mass%) Co. The activity tests of the catalysts were carried out for hydrogenation of furfural to MF by changing reaction parameters such as pressure, loading of catalyst, temperature, and time. A 94.1% MF yield was achieved in the presence of the Co‐Cu/ZrO2 catalyst with 0.08 g/g (8 mass%) Cu and 0.118 g/g (11.8 mass%) Co at 200°C for 6 hours under 1.5 MPa H2 pressure. The catalyst also showed good reusability properties after the fifth use. The catalysts were characterized by Brunauer‐Emmet‐Teller method, X‐ray diffraction, X‐ray photoelectron spectroscopy, and temperature programmed reduction techniques.

Functional group hydrogenation of cinnamaldehyde to hydrocinnamyl alcohol over nickel-ruthenium containing hydrotalcite

Functional group hydrogenation of α-β unsaturated aldehydes to fine chemicals is a potential process in organic synthesis. In this study, we demonstrate the complete functional group hydrogenation of cinnamaldehyde (CAL) to hydrocinnamyl alcohol (HCOL) over magnesium aluminium hydrotalcite (MAHT) having bimetallic nickel/ruthenium (1.3% Ni and 0.74% Ru) species (MANR–HT). The catalyst shows complete conversion of CAL with 97.5% selectivity of HCOL at 150 °C and 1 MPa H2 pressure. The synergic effect of bimetallic Ni/Ru and basicity of the HT material facilitated the high catalytic activity of MANR–HT in the CAL hydrogenation. The catalyst also demonstrated comparable activity even after several runs.

Catalytic hydrocracking of a Mexican heavy oil on a MoS2/al2o3catalyst: II. Study of the transformation of isolated aromatics fraction obtained from SARA analysis

Catalytic hydrocracking of isolated aromatics fraction from a heavy crude oil was studied on a slurry batch reactor at isothermal conditions using 8.27 MPa H2 pressure, different temperatures (380 °C, 390 °C, and 400 °C), different reaction times (1.0 h, 2.5 h, and 4.0 h) and employing a sulfided Mo/γ-Al2O3 catalyst. The ASTM D2007 method had been applied to a Mexican heavy oil to obtain the aromatics fraction. Feedstock and products (gas and liquid) were analyzed by GC-MSD and GC-FID. Additionally, the liquid phase was analyzed by the ASTM D7169 method. A kinetic model was proposed to establish the effect of the processing the heavy cuts (gasoil, atmospheric residue, and vacuum residue) to light distillate cuts production (gas, naphtha and, kerosene). It was determined that the feedstock is composed of aromatics (mono, di, tri, or tetra-cycle) with alkyl tails, oxygenated aromatics, nitrogen aromatics, and sulfur aromatics. The catalytic hydrocracking products were saturate compounds and lower molecular weight aromatics; no coke was detected. The produced gas was composed by saturated compounds. The fitted kinetic parameters and the chromatographic analyses indicate that aromatics in feedstock were transformed following primary reactions in series. The main producers of naphtha were aromatics in kerosene and atmospheric residue, the reactions were dealkylation or hydrogenation; this after the opening of aromatic rings in the high molecular aromatics. The gas producers were substituted aromatics in the kerosene cut that is kept at the liquid phase during reaction, also, at high temperatures the hydrotreatment reactions of aromatic compounds in gasoil produces gas.

Hydrogenation of furfural to furfuryl alcohol over efficient sol-gel nickel-copper/zirconia catalyst

Furfuryl alcohol (FA), a valuable compound from furfural (FF) was synthesized by efficient Ni-Cu/ZrO2 catalysts. The catalysts with varying Ni and Cu loading were developed by sol-gel method and characterized by Brunauer-Emmet-Teller (BET) method, X-ray diffraction, Temperature Programmed Reduction (TPR), X-ray photoelectron spectroscopy techniques. Cu/ZrO2 and Ni/ZrO2 catalysts were also tested to compare the effect of the Ni-Cu/ZrO2 catalyst. Both Ni and Cu showed the synergistic effect on FA formation. The Ni-Cu/ZrO2 catalyst was used for hydrogenation of FF by changing pressure, catalyst loading, temperature and time. A 93% FA yield was achieved over the 7Ni-Cu/ZrO2 catalyst with 0.07 g Ni and 0.1 g Cu/1 g ZrO2 at 200 °C for 4 h under 1.5 MPa H2 pressure. The sol-gel Ni-Cu/ZrO2 catalyst without the use of expensive noble metals is effective on the hydrogenation of FF to FA relatively in mildly reaction pressure. The Ni-Cu/ZrO2 catalyst was used for hydrogenation of FF by changing pressure, catalyst loading, temperature and time. A 93% FA yield was achieved over the 7Ni-Cu/ZrO2 catalyst with 0.07 g Ni and 0.1 g Cu/1 g ZrO2 at 200 °C for 4 h under 1.5 MPa H2 pressure. The sol-gel Ni-Cu/ZrO2 catalyst without the use of expensive noble metals is effective on the hydrogenation of FF to FA relatively in mildly reaction pressure.

Enhanced activity of Ru-Ir nanoparticles over SiC for hydrogenation of levulinic acid at room-temperature

The hydrogenation of levulinic acid (LA) to γ-valerolactone (GVL) under mild condition is a promising but challenging process. Herein, SiC supported Ru-Ir bimetallic catalyst exhibit enhanced catalytic activity for aqueous hydrogenation of LA into GVL under mild conditions. Comparing with monometallic Ir3/SiC and Ru3/SiC, the conversion of LA over bimetallic Ru0.5-Ir2.5/SiC catalyst increase from 51.2 % and 45.9% to 100% at 25 °C and 0.2 MPa of H2 pressure. The enhanced catalytic activity of Ru0.5-Ir2.5/SiC catalyst originates from the electronic synergistic effect among Ru, Ir and SiC. Due to the electron transfer, electron-richened Ir nanoparticles show stronger ability for H2 dissociation, and the SiC surface produces more active sites to accommodate hydrogen species that spill over from Ir and Ru. The adsorption and hydrogenation of LA molecules occur on the surface of SiC.

Efficient Synthesis of Sugar Alcohols under Mild Conditions Using a Novel Sugar-Selective Hydrogenation Catalyst Based on Ruthenium Valence Regulation

Sugar alcohols are the prominent alternatives of sugars in food, medical, and health industries. The ruthenium supported on multiwalled carbon nanotubes (Ru/MWCNTs) catalysts were prepared based on the Ru valence regulation strategy and applied for selective sugar hydrogenation to prepare various sugar alcohols including xylitol, arabinitol, sorbitol, mannitol, and galactitol for the first time, with high selectivity (>99.0%) and yield (>98.0%) under mild conditions (≤110 °C, 3.0 MPa H2 pressure). The hydrogenation reaction of xylose was further optimized and under mild conditions (100 °C, 3.0 MPa H2 pressure, and 500 rpm), which were lower than ever reported for high efficient synthesis of xylitol, 99.8% xylose conversion and 99.0% xylitol yield were achieved after 120 min of reaction.

Green process for hydrogenation of methyl ricinoleate to methyl 12-hydroxystearate over diatomite supported Cu/Ni bimetallic catalyst

A series of diatomite supported Cu/Ni bimetallic catalysts were prepared using the co-impregnation method to improve the efficiency and selectivity toward methyl 12-hydroxystearate in the hydrogenation of methyl ricinoleate. The catalysts were characterized using X-ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy and energy dispersive X-ray spectroscopy (SEM-EDS), X-ray photoelectron spectroscopy (XPS) and temperature programmed reduction (H2-TPR). All the characterization results verified the formation of highly dispersed Cu/Ni alloy on support. Moreover, by subtly regulating the Ni/Cu molar ratio as well as the reaction parameters, the hydrogenation of methyl ricinoleate to methyl 12-hydroxystearate proceeded efficiently and selectively, affording 97% yield of methyl 12-hydroxystearate and nearly equivalent conversion of methyl ricinoleate under 2 MPa H2 pressure and at 130 °C in 4 h with only 1 wt% of the catalyst Ni7Cu1/diatomite (based on methyl ricinoleate). Besides, the supported Cu–Ni bimetallic catalyst is stable during recycle and reuse. After five cycles of reuse, much catalytic activity is still preserved. Therefore, this low-cost and stable bimetallic catalyst would be promising for the hydrogenation of methyl ricinoleate to methyl 12-hydroxystearate, representing an example of green catalysis for efficiently conversion of biomass to value-added chemicals and materials.

C9 Petroleum Resin Hydrogenation over a PEG1000-Modified Nickel Catalyst Supported on a Recyclable Fluid Catalytic Cracking Catalyst Residue.

A PEG1000-modified nickel-based catalyst (Ni-PEG1000/FC3R) supported on an activated fluid catalytic cracking catalyst residue (FC3R) was synthesized and applied to C9 petroleum resin (C9PR) hydrogenation. The results of the Brunauer–Emmett–Teller method, X-ray diffraction, H2 temperature-programmed reduction, and scanning electron microscopy–energy-dispersive X-ray spectroscopy show that the Ni-PEG1000/FC3R catalyst had a smaller crystallite size and higher Ni dispersion than those of a Ni/FC3R catalyst. The prepared Ni-PEG1000/FC3R catalyst was applied in a hydrogenation of C9PR at 270 °C and 6 MPa H2 pressure for 3 h. Under these conditions, the bromine value of C9PR was decreased from 46.1 g Br/100 g (Gardner color grade no. 11) to 0.72 g Br/100 g (Gardner color grade no. 1), and the sulfur content was reduced from 25.7 to 1.66 mg kg–1. Experimental results show that the Ni-PEG1000/FC3R catalyst exhibited high activity and stability for C9PR hydrogenation.

Selective aqueous-phase hydrogenation of glucose and xylose over ruthenium-based catalysts: influence of the support

Sorbitol and xylitol are value-added renewable chemicals that can be obtained from biomass through the hydrogenation of monosaccharides (glucose and xylose, respectively) using ruthenium-based catalysts. This paper reports an in depth study on the activity and selectivity of Ru catalysts supported on different materials, gamma alumina (A), zirconia (Z), zirconia-alumina (Z-A), phosphated zirconia (ZP) and phosphated zirconia-alumina (ZP-A), focusing on the effect of the support. Catalyst performance was evaluated under relatively mild reaction conditions, 90 °C, 1.25 MPa H2 pressure and water as solvent. The results showed that the activity greatly depends on the support used. The most active catalyst analyzed in the present paper, Ru/ZP-A, gave a selectivity of 97% and 97.5% towards sorbitol and xylitol, at high conversion levels of glucose and xylose (over 85%), respectively. Characterization of the catalysts by N2 physisorption, XRD, TGA, SEM, TEM, TPR and XPS provided valuable insight in the relation between the catalyst structure and its activity.

Preparation of reduced Ni-Nb-O composite hydrogenation catalysts for highly selective conversion of free fatty acids to n-alkanes

Catalytic deoxygenation of fatty acids to alkanes is an ideal route to produce biodiesel with high heating value. However, traditional transition-metal sulfide and noble metal catalysts are sulfide-contaminated, high cost, or easily poisoned. To overcome the above issues, this work developed a non-noble and sulfide-free reduced transition-metal composite NixNbyOz, which was effective to selectively hydrogenate stearic acid, a typical fatty acid model compound, to diesel-range alkanes. By using a simple slurry method, reduced NixNbyOz catalysts have been successfully prepared with an outstanding catalytic performance. The results showed that catalyst Ni0.5Nb0.5Oz effectively converted stearic acid to n-alkanes with nearly 100% conversion and >99% n-alkanes selectivity at mild conditions (513 K and 3.5 MPa of H2 pressure). Appropriate Nb species improved the dispersion of Ni species, which may supply more hydrogenation active sites. Two possible reaction routes of stearic acid were proposed, and the hydrogenolysis of stearyl stearate was confirmed as the rate-determining step based on the kinetics experiments. Because of moderate acidity of Nb species, the ratio of C17/C18 alkane was not markedly affected by reaction conditions when the conversion of stearic acid was higher than 99%. Moreover, catalyst Ni0.5Nb0.5Oz showed a high recycle ability and compatibility for other long-chain fatty acids, demonstrating that catalyst Ni0.5Nb0.5Oz is a promising green catalyst for producing biodiesel from fatty acids.

Selective conversion of biomass-derived furfural to cyclopentanone over carbon nanotube-supported Ni catalyst in Pickering emulsions

A well-characterized carbon nanotube-supported nickel catalyst (Ni/CNTox) was assembled at the liquid-liquid interface and evaluated for the conversion of furfural. The nanoparticles were found to be mainly distributed on the interface of the emulsion droplets, forming stable Pickering emulsion. Catalytic activity was studied under different reaction conditions to determine an optimal condition for the rearrangement of furfural to cyclopentanone, an important precursor to valuable chemicals. It was found that the highest furfural conversion (35%) and cyclopentanone yield (25%) was obtained at 200 °C, 2 MPa of H2 pressure, and with the same dodecane/water ratio after 1 h of reaction.

Biomass-derived furfural conversion over Ni/CNT catalysts at the interface of water-oil emulsion droplets

Carbon nanotubes-supported Ni catalysts were investigated for the hydrogenation of furfural as a biomass-derived furanic model compound at the liquid-liquid interface of Pickering emulsions in a batch reactor at 200 °C and 2.0 MPa of H2 pressure. The catalysts were characterized by N2 physisorption, He-TPD/MS, NH3-TPD/MS, TEM, CO chemisorption, H2-TPR, contact angle and optical/fluorescent microscopy. It was found that an increase of surface oxygen groups allows for the formation of amphiphilic particles. The amphiphilic 10%Ni/CNTox particles were homogeneous dispersed at the water-oil interface of the emulsion droplets thus enhancing the catalytic activity in furfural conversion.

Transition-metal influence (Fe, Co, Ni, Cu) on the MoWS catalyst for biphenyl hydrogenation

The hydrogenation of aromatic hydrocarbon compounds derived of hydrocarbon fuels is crucial to avoid the current environment pollution, harmful to human health. Also, the hydrogenated products can be used as chemical intermediates, additives, and in other chemical processes. The search of efficient and cost-effective catalysts for the hydrogenation of aromatic hydrocarbon compounds is a current challenge in the industrial and scientific community. In this study, trimetallic unsupported MMoW (M = Fe, Co, Ni, and Cu) sulfide catalysts were synthetized and tested in the liquid-phase biphenyl (BP) hydrogenation at 300 °C and 5.5 MPa of H2 pressure. The catalysts were characterized by XRD, SEM-EDX, TEM-SAED and adsorption–desorption of N2. The presence of NiS, CoSx, MoFe2S4, Cu9S5 crystalline sulfide phases together with Mo(W)S2 crystalline sulfide phase, as well as the crystallite size and the surface area, influenced the catalytic performance. Ni-based catalysts were the most active in the BP hydrogenation. A BP conversion value of ~99% of biphenyl and selectivity of 52% towards cyclohexylbenzene (CHB) and 47% towards bicyclohexyl were reached using NiMoWS catalyst. The presence of NiS crystals, stacked curve-shape Mo(W)S2 crystalline phases and larger surface area values increased the catalytic activity using NiMoWS catalysts.

Promoting selective hydrodeoxygenation of guaiacol over amorphous nanoporous NiMnO2

Nanoporous Ni (NP-Ni) and NiMnO2 (NP- NiMnO2) were prepared with mechanical alloying method and compared for the hydrodeoxygenation (HDO) of guaiacol. It was shown that MnO2 as an additive has a significant influence on the catalytic performance as it could accordingly change the material properties. Results of characterization demonstrated that NP-NiMnO2 had a unique structure with higher degree of amorphization than NP-Ni, which significantly facilitated the activity of HDO. Under the optimal reaction conditions of 150 °C and 0.5 MPa of H2 pressure, guaiacol was completely converted into cyclohexanol with 95.6% selectivity and NP-NiMnO2 was recycled 6 times without obvious deactivation.

Highly active Ir/SiC catalyst for aqueous hydrogenation of levulinic acid to γ-valerolactone

A 3 wt% Ir/SiC catalyst prepared by the wet impregnation method showed excellent catalytic activity and stability for the aqueous hydrogenation of levulinic acid (LA) to γ-valerolactone (GVL) in a batch reactor system. LA was completely converted to GVL at 50 °C and 0.2 MPa of H2 pressure with 100% selectivity and a high turnover frequency (TOF) of 333 h−1. The high activity of Ir/SiC catalyst could be related to the Schottky-type contact between Ir and SiC solid phases, which promotes electron transfer between support and metal. Due to the excellent acid resistance of SiC support, the Ir/SiC catalyst showed high catalytic stability and nearly no loss of activity after 5 consecutive catalytic operation cycles.

One-Step Encapsulation of Bimetallic Pd–Co Nanoparticles Within UiO-66 for Selective Conversion of Furfural to Cyclopentanone

The design of efficient catalysts is of important significance for the transformation of biomass into chemicals. In this work, bimetallic Pd–Co nanoparticles were encapsulated within UiO-66 to form a core–shell Pd–Co@UiO-66 catalyst via a facile one-step strategy. The as-synthesized Pd–Co@UiO-66 catalysts were characterized and applied to the selective hydrogenation of furfural (FUR) to cyclopentanone (CPO). Compared with the monometallic Pd@UiO-66, the Pd–Co@UiO-66 could demonstrate excellent performance with 96% CPO selectivity and 99% FUR conversion at 120 °C under 3 MPa H2 pressure for 12 h. It was found that trace Co had synergetic and promoting effects on the catalytic performance. The core–shell catalysts showed more outstanding recyclability than the supported catalysts, which could maintain high CPO yield after 5th runs.

Facile synthesis of small MgH2 nanoparticles confined in different carbon materials for hydrogen storage

We introduce a facile chemical solid state method to in situ grow MgH2 nanoparticles in various carbon materials. Commercial carbon materials, containing coconut shell charcoal (CSC), multi-walled carbon nanotube (CNT), graphite (G) and activated carbon (AC) are employed as the templates. The MgH2@X (X = CSC, CNT, G and AC) composites were successfully obtained by the simple solid state method. The hydrogen storage properties of MgH2@X (X = CSC, CNT, G and AC) composites are systematically studied by temperature-programmed desorption system, isothermal de/hydrogenation apparatus and differential scanning calorimetry measurements. Experimental results reveal that the MgH2@CSC composites have the most fascinating hydrogen absorption and desorption performance, followed by MgH2@CNT, MgH2@G and MgH2@AC composites. The dehydrogenation of MgH2@CSC composites begins at 245 °C. Moreover, the MgH2@CSC composites exhibit superior de/hydrogenation kinetic performance. The composites could desorb 5.4 wt% hydrogen within 10 min at 325 °C, and the dehydrogenated composites take up 5.0 wt% hydrogen within 5 min at 250 °C under 2 MPa H2 pressure. Among the carbon materials, CSC with layered structure composed of interconnected wrinkles is most beneficial to maintain the high dispersity and nano size of MgH2 nanoparticles, resulting in the superior de/hydrogenation performance.

Silica/titania composite-supported NiCo catalysts with combined catalytic effects for phenol hydrogenation under fast and mild conditions

The effect of titanium as a promoter for the nickel-cobalt/silica-titania (NiCo/Si-Ti) catalyst in the hydrogenation of phenol was comparatively studied. In the phenol hydrogenation under mild reaction conditions (1 MPa H2 pressure and 100 °C), the Ti-promoter induces the formation of the Coδ−−OV−Ti3+ active sites and enhances the hydrogenation activity of the NiCo/Si catalyst to convert phenol to cyclohexanol. The catalytic hydrogenation with the optimal composition of the NiCo/Si-1.0Ti (Si:Ti ratio of 8.5:1) catalyst was completed within 1 h (conversion 98.2 % and selectivity >99 %), which was more efficiently than that with other Ti-doped catalysts and NiCo/Si as baseline, indicating a strong positive synergistic effect between the metal (Ni-Co) and support (Ti-Si) components of the catalyst in this reaction. Additionally, the kinetics, pathway and catalytic mechanism of the hydrogenation of phenol are also examined. Furthermore, the NiCo/Si-1.0Ti catalysts also showed a good performance at reducing the unstable oxygenated compounds in the bio-oil.

Hydroprocessing of Oleic Acid for Production of Jet-Fuel Range Hydrocarbons over Cu and FeCu Catalysts

In the present study, a series of monometallic Cu/SiO2-Al2O3 catalysts exhibited immense potential in the hydroprocessing of oleic acid to produce jet-fuel range hydrocarbons. The synergistic effect of Fe on the monometallic Cu/SiO2-Al2O3 catalysts of variable Cu loadings (5–15 wt%) was ascertained by varying Fe contents in the range of 1–5 wt% on the optimized 13% Cu/SiO2-Al2O3 catalyst. At 340 °C and 2.07 MPa H2 pressure, the jet-fuel range hydrocarbons yield and selectivities of 51.8% and 53.8%, respectively, were recorded for the Fe(3)-Cu(13)/SiO2-Al2O3 catalyst. To investigate the influence of acidity of support on the cracking of oleic acid, ZSM-5 (Zeolite Socony Mobil–5) and HZSM-5(Protonated Zeolite Socony Mobil–5)-supported 3% Fe-13% Cu were also evaluated at 300–340 °C and 2.07 MPa H2 pressure. Extensive techniques including N2 sorption analysis, pyridine- Fourier Transform Infrared Spectroscopy (Pyridine-FTIR), X-ray Diffraction (XRD), X-ray Photoelectron Spectroscopy (XPS), and H2-Temperature Programmed Reduction (H2-TPR) analyses were used to characterize the materials. XPS analysis revealed the existence of Cu1+ phase in the Fe(3)-Cu(13)/SiO2-Al2O3 catalyst, while Cu metal was predominant in both the ZSM-5 and HZSM-5-supported FeCu catalysts. The lowest crystallite size of Fe(3)-Cu(13)/SiO2-Al2O3 was confirmed by XRD, indicating high metal dispersion and corroborated by the weakest metal–support interaction revealed from the TPR profile of this catalyst. CO chemisorption also confirmed high metal dispersion (8.4%) for the Fe(3)-Cu(13)/SiO2-Al2O3 catalyst. The lowest and mildest Brønsted/Lewis acid sites ratio was recorded from the pyridine–FTIR analysis for this catalyst. The highest jet-fuel range hydrocarbons yield of 59.5% and 73.6% selectivity were recorded for the Fe(3)-Cu(13)/SiO2-Al2O3 catalyst evaluated at 300 °C and 2.07 MPa H2 pressure, which can be attributed to its desirable textural properties, high oxophilic iron content, high metal dispersion and mild Brønsted acid sites present in this catalyst.

Enhancement of bio-oil hydrodeoxygenation activity over Ni-based bimetallic catalysts supported on SBA-15

Three Ni-based bimetallic catalysts were prepared on hexagonally structured mesoporous SBA-15 supports(NiCu/SBA-15, NiMn/SBA-15, NiZn/SBA-15). Hydrodeoxygenation (HDO) of biooil was performed at 250–350 °C for 45 min with 3 MPa H2 pressure in the presence of the three catalysts. HDO reaction yielded a primary products of gas, two immiscible liquids (light oil and heavy oil) and char. High catalyst surface area resulted in a high heavy oil yield (40.8–60.6 wt%). Bimetallic catalysts decreased yield of light oil (3.6–11.7 wt%), while increased the gas fraction (16.3–43.7 wt%) compared with the data from the monometallic Ni/SBA-15 catalyst (20.3–30.4 and 6.6–26.2 wt% yields, respectively). Use of bimetallic catalysts instead of monometallic catalyst enhanced fuel properties of heavy oil; such as moisture content (from 11.4 to 2.0–8.8 wt%), acidity (from 62.2 to 49.2–59.8 mg KOH/g oil), viscosity (from 7.1 to 3.2–4.3 cSt) and oxygen content (from 32.2 to 26.2–34.6 wt%). Cyclohexanone, 4-ethylphenol, and methyl-cyclopentenone, which were lack in the bio-oil, were detected after HDO reaction and these components could be produced via demethoxylation, hydrogenation, dehydration, and dehydroxylation under the presence of bimetallic catalysts, thereby improving the fuel properties of the heavy oil.