Hydrodeoxygenation of Phenolic Model Compounds over MoS2 Catalysts with Different Structures

摘要/Abstract

摘要： Several MoS₂ catalysts of different structure,prepared by in situ decomposition of ammonium heptamolybdate(AHM)and molybdenum naphthenate(MoNaph),and by MoS₂ exfoliation(TDM),were characterized by BET, X-ray diffraction(XRD),Energy Dispersive X-ray(EDX)and transmission electron microscopy(TEM).The analysis showed that MoS₂ structure was dependant upon the preparation procedure.The activity of the catalysts was determined by measuring the hydrodeoxygenation(HDO)of phenol,4-methylphenol and 4-methoxyphenol using a batch autoclave reactor operated at 2.8 MPa of hydrogen and temperatures ranging from 320-370℃.By comparing the conversion,the reactivity order of the catalysts was:AHM>TDM-D>MoNaph>thermal>MoS₂ powder>TDM-W.Also,the effect of reaction temperature on the HDO conversion was explained in terms of equilibrium of reversible reaction kinetics.The main products of the HDO for phenolic compounds were identified by gas chromatography/mass spectrometry(GC/MS).The results showed that the product distribution and the HDO selectivity were correlated with the reaction temperature.Two parallel reaction routes,direct hydrogenolysis and combined hydrogenation-hydrogenolysis,were confirmed by the analysis of the product distribution.High temperature favored hydrogenolysis over hydrogenation for HDO of phenol and 4-methoxyphenol,whereas for 4-methylphenol the reverse was true.

关键词: ammonium heptamolybdate derived MoS₂, structure effect, characterization, hydrodeoxygenation, reactivity, product distribution

Abstract: Several MoS₂ catalysts of different structure,prepared by in situ decomposition of ammonium heptamolybdate(AHM)and molybdenum naphthenate(MoNaph),and by MoS₂ exfoliation(TDM),were characterized by BET, X-ray diffraction(XRD),Energy Dispersive X-ray(EDX)and transmission electron microscopy(TEM).The analysis showed that MoS₂ structure was dependant upon the preparation procedure.The activity of the catalysts was determined by measuring the hydrodeoxygenation(HDO)of phenol,4-methylphenol and 4-methoxyphenol using a batch autoclave reactor operated at 2.8 MPa of hydrogen and temperatures ranging from 320-370℃.By comparing the conversion,the reactivity order of the catalysts was:AHM>TDM-D>MoNaph>thermal>MoS₂ powder>TDM-W.Also,the effect of reaction temperature on the HDO conversion was explained in terms of equilibrium of reversible reaction kinetics.The main products of the HDO for phenolic compounds were identified by gas chromatography/mass spectrometry(GC/MS).The results showed that the product distribution and the HDO selectivity were correlated with the reaction temperature.Two parallel reaction routes,direct hydrogenolysis and combined hydrogenation-hydrogenolysis,were confirmed by the analysis of the product distribution.High temperature favored hydrogenolysis over hydrogenation for HDO of phenol and 4-methoxyphenol,whereas for 4-methylphenol the reverse was true.

Key words: ammonium heptamolybdate derived MoS₂, structure effect, characterization, hydrodeoxygenation, reactivity, product distribution

杨运泉, 罗和安, 童刚生, Kevin J.Smith, TYE Ching Thian. Hydrodeoxygenation of Phenolic Model Compounds over MoS₂ Catalysts with Different Structures[J]. , 2008, 16(5): 733-739.

YANG Yunquan, LUO He'an, TONG Gangsheng, Kevin J. Smith, TYE Ching Thian. Hydrodeoxygenation of Phenolic Model Compounds over MoS₂ Catalysts with Different Structures[J]. , 2008, 16(5): 733-739.

参考文献

1 Speight, J., Chemistry and Technology of Petroleum, Marcel Dekker, New York (1991).
2 Furimsky, E., “Catalytic hydrodeoxygenation”, Appl. Catal. A, 199, 147-190 (2000).
3 Viljava, T.R., Komulainen, R.S., Krause, A.O.I., “Effect of H₂S on the stability of CoMo/Al₂O₃ catalysts during hydrodeoxygenation”, Catal. Today, 60, 83-92 (2000).
4 Li, C.L., Xu, Z., Gates, B.C., Petrakis, L., “Catalytic hydroprocessing of SRC-I I heavy distillate fractions (4) Hydrodeoxygmation of phenolic compounds in the acidic fractions”, Ind. Eng. Chem. Proc. Des. Dev., 24, 92-97 (1985).
5 Daage, M., Chianelli, R.R., “Structure-function relations in molybdenum sulfide catalysts:The rim-edge model”, J. Catal., 149, 414-427 (1994).
6 Farag, H., Sakanishi, K., Kouzu, M., Matsumura, A., Sugimoto, Y., Saito, I., “Dibenzothiophene hydrodesulfurization over synthesized MoS₂ catalysts”, J. Mol. Catal. A, 206, 399-408 (2003).
7 Devers, E., Afanasiev, P., Jouguet, B., Vrinat, M., “Hydrothermal syntheses and catalytic properties of dispersed molybdenum sulfides”, Catalysis Letters, 82 (1/2), 13-17 (2002).
8 Del Bianco, A., Panariti, N., Marchionna, M., “Upgrading heavy oil using slurry processes”, Chemtech., 25, 35-43 (1995) .
9 Tye, C.T., Smith, K.J., “Hydrodesulfurization of dibenzothiophene over exfoliated MoS₂ catalyst”, Catalysis Today, 116, 461-468 (2006).
10 Hall, A.G., Chan, A.D., Smith, K.J., “Characterization of dispersed hydroprocessing catalysts prepared in reversed micelles”, Can. J. Chem. Eng., 76 (4), 744-752 (1998).
11 Alonso, G., Valle, M.D., Cruz, J., Licea-Claverie, A., Petranovskii V., Fuentes, S., “Preparation of MoS₂ and WS₂ catalysts by in situ decomposition of ammonium thiosalts”, Catal. Lett., 52, 55-61 (1998).
12 Tye, C.T., Smith, K.J., “Cold Lake bitumen upgrading using exfloliated MoS₂”, Catal. Lett., 95, 203-209 (2004).
13 Del Valle, M., Avalos-Borja, M.J., Cruz, S.F., “Exfoliation of MoS₂ catalysts:structural and catalytic changes”, Mater. Res. Soc. Symp. Proc., 351, 287-292 (1994).
14 Laurent, E., Delmon, B., “Influence of oxygen, nitrogen, and sulfur-containing compounds on the hydrodeoxygenation of phenols over sulfided CoMo/γ-A1₂O₃ and NiMo/γ-A1₂O₃ Catalysts”, Ind. Eng. Chem. Res., 32, 2516-2524 (1993).
15 Girgis, M.J., Gates, B.C., “Reactivities, reaction networks, and kinetics in high pressure catalytic hydroprocessing”, Ind. Eng. Chem. Res., 30, 2021-2058 (1991).
16 Wandas, R., Surygala, J., Sliwka, E., “Conversion of cresols and naphthalene in the hydroprocessing of three-component model mixtures simulating fast pyrolysis tars”, Fuel, 75, 687-694 (1996).
17 Massoth, F.E., Politzer, P., Concha, M.C., “Catalytic hydrodeoxygenation of methyl-substituted phenols:Correlations of kinetic parameters with molecular properties”, J. Phys. Chem. B, 110, 14283-14291 (2006).
18 Odebunmi, E.O., Ollis, D.F., “Catalytic hydrodeoxygenation (I) Conversion of o-, p-, and m-cresols”, J. Catal., 80, 56-64 (1983).
19 Furimsky, E., Massoth, F.E., “Hydrodenitrogenation of petroleum”, Catal. Rev., 47, 297-489 (2005).
20 Chon S., Allen, D.T., “Catalytic hydroprocessing of chlorophenols”, AIChE J., 37 (11), 1730-1732 (1991).
21 Li, C.L., Xu, Z.R., Cao, Z.A., Gates, B.C., “Hydrodeoxygenation of 1-naphthol catalyzed by sulfided Ni-Mo/γ-A1₂O₃ :Reaction network”, AIChE J., 31, 170-174 (1985).
22 Bredenberg, J.B., Huuska, M., R ty, J., Korpio, M., “Hydrogenolysis and hydrocracking of the carbon-oxygen bond (I) Hydrocracking of some simple aromatic O-compounds”, J. Catal., 77, 242-247 (1982).
23 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”, Catal. Today, 29 (1-4), 297-301 (1996).
24 Yang, Y.Q., Tye, C.T., Smith, K.J., “Inflenece of MoS₂ catalyst morphology on the hydrodeoxygenation of phenols”, Catal. Comm., 9, 1364-1368 (2008).
25 Joensen, P., Frindt, R.F., Morrison, S.R., “Single-layer MoS₂”, Mater. Res. Bull., 21, 457-461 (1986).
26 Iwata, Y., Sato, K., Yoneda, T., Miki, Y., Sugimoto, Y., Nishijima, A., Shimada, H., “Catalytic functionality of unsupported molybdenum sulfide catalysts prepared with different methods”, Catal. Today, 45 (1-4), 353-359 (1998).
27 Kirby, S.R., Song, C., Schobert, H.H., “Hydrodeoxygenation of O-containing polycyclic model compounds using a novel organometallic catalyst precursor”, Catal. Today, 31, 121-135 (1996).
28 Perry, R., Chilton, C.H., Chemical Engineers' Handbook, McGrew-Hill, New York (1973). 29 Levenspiel, O., Chemical Reaction Engineering, 3rd ed., John Wiley, New York (2002).

[1]	Juan Xu, Ping Zhu, Islam H. El Azab, Ben Bin Xu, Zhanhu Guo, Ashraf Y. Elnaggar, Gaber A.M. Mersal, Xiangyi Liu, Yunfei Zhi, Zhiping Lin, Hassan Algadi, Shaoyun Shan. An efficient bifunctional Ni-Nb₂O₅ nanocatalysts for the hydrodeoxygenation of anisole[J]. 中国化学工程学报, 2022, 49(9): 187-197.
[2]	N. M'hanni, T. Anik, R. Touir, M. Galai, M. Ebn Touhami, E.H. Rifi, Z. Asfari, S. Bakkali. Effect of additives on nickel-phosphorus deposition obtained by electroless plating: Characterization and corrosion resistance in 3%(mass) sodium chloride medium[J]. 中国化学工程学报, 2022, 44(4): 341-350.
[3]	Yichao Wu, Zhiwei Xie, Xiaofeng Gao, Xian Zhou, Yangzhi Xu, Shurui Fan, Siyu Yao, Xiaonian Li, Lili Lin. The highly selective catalytic hydrogenation of CO₂ to CO over transition metal nitrides[J]. 中国化学工程学报, 2022, 43(3): 248-254.
[4]	Wei Guo, Bo Zhang, Jie Zhang, Zhiqiang Wu, Yaowu Li, Bolun Yang. Liquid chemical looping gasification of biomass: Thermodynamic analysis on cellulose[J]. 中国化学工程学报, 2021, 37(9): 79-88.
[5]	Saeed Nahidi, Iraj Jafari Gavzan, Seyfolah Saedodin, Mahmoud Salari. Experimental investigation on the effect of surface characterization of electrodes on the gas bubble dynamics in electrolyte flow and performance of FLA batteries by using PIV[J]. 中国化学工程学报, 2021, 33(5): 30-39.
[6]	Yan Zhang, Bekir Engin Eser, Peter Kristensen, Zheng Guo. Fatty acid hydratase for value-added biotransformation: A review[J]. 中国化学工程学报, 2020, 28(8): 2051-2063.
[7]	M. Ajdar, A. Azdarpour, A. Mansourizadeh, B. Honarvar. Improvement of porous polyvinylidene fluoride-co-hexafluropropylene hollow fiber membranes for sweeping gas membrane distillation of ethylene glycol solution[J]. 中国化学工程学报, 2020, 28(12): 3002-3010.
[8]	Changhong Yu, Litao Chen, Baojiang Sun. Experimental characterization of guest molecular occupancy in clathrate hydrate cages: A review[J]. 中国化学工程学报, 2019, 27(9): 2189-2206.
[9]	Imran Ali, Changsheng Peng, Iffat Naz. Removal of lead and cadmium ions by single and binary systems using phytogenic magnetic nanoparticles functionalized by 3-marcaptopropanic acid[J]. 中国化学工程学报, 2019, 27(4): 949-964.
[10]	Andrew Ng Kay Lup, Faisal Abnisa, Wan Mohd Ashri Wan Daud, Mohamed Kheireddine Aroua. Synergistic interaction of metal–acid sites for phenol hydrodeoxygenation over bifunctional Ag/TiO₂ nanocatalyst[J]. Chinese Journal of Chemical Engineering, 2019, 27(2): 349-361.
[11]	Canan Onac, Ahmet Kaya, Duygu Ataman, Nefise Ayhan Gunduz, H. Korkmaz Alpoguz. The removal of Cr(VI) through polymeric supported liquid membrane by using calix[4]arene as a carrier[J]. Chinese Journal of Chemical Engineering, 2019, 27(1): 85-91.
[12]	Haimin Shen, Yan Wang, Jinhui Deng, Long Zhang, Yuanbin She. Catalyst-free and solvent-free oxidation of cycloalkanes (C5-C8) with molecular oxygen: Determination of autoxidation temperature and product distribution[J]. Chinese Journal of Chemical Engineering, 2018, 26(5): 1064-1070.
[13]	Guodong Wang, Jianchun Jiang, Kang Sun, Jianzhong Wu. An improved theoretical procedure for the pore-size analysis of activated carbon by gas adsorption[J]. Chinese Journal of Chemical Engineering, 2018, 26(3): 551-559.
[14]	Guozhang Chang, Ximin Yan, Pengyu Qi, Mei An, Xiude Hu, Qingjie Guo. Characteristics of reactivity and structures of palm kernel shell (PKS) biochar during CO₂/H₂O mixture gasification[J]. Chinese Journal of Chemical Engineering, 2018, 26(10): 2153-2161.
[15]	Zhihui Sun, Weihong Zhang. Chemical composition and structure characterization of distillation residues of middle-temperature coal tar[J]. , 2017, 25(6): 815-820.

Hydrodeoxygenation of Phenolic Model Compounds over MoS₂ Catalysts with Different Structures

Hydrodeoxygenation of Phenolic Model Compounds over MoS₂ Catalysts with Different Structures

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价