Phenol hydrogenation to cyclohexanone over palladium nanoparticles loaded on charming activated carbon adjusted by facile heat treatment

doi:10.1016/j.cjche.2020.06.005

Chinese Journal of Chemical Engineering ›› 2020, Vol. 28 ›› Issue (10): 2600-2606.DOI: 10.1016/j.cjche.2020.06.005

• Catalysis, Kinetics and Reaction Engineering • Previous Articles Next Articles

Phenol hydrogenation to cyclohexanone over palladium nanoparticles loaded on charming activated carbon adjusted by facile heat treatment

Chunhua Zhang^1,2, Guangxin Yang¹, Hong Jiang¹, Yefei Liu¹, Rizhi Chen¹, Weihong Xing¹

1 State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing 210009, China;
2 Changzhou Key Laboratory of Eco-Textile Technology, Changzhou Vocational Institute of Textile and Garment, Changzhou 213164, China

Received:2020-04-08 Revised:2020-05-26 Online:2020-12-03 Published:2020-10-28
Contact: Rizhi Chen, Weihong Xing
Supported by:
The financial supports from the National Key R&D Program (2016YFB0301503), the National Natural Science Foundation of China (21776127, 21921006), the Jiangsu Province Key R&D Program (BE2018009-2), a project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and the State Key Laboratory of Materials-Oriented Chemical Engineering (ZK201902) of China are gratefully acknowledged.

Phenol hydrogenation to cyclohexanone over palladium nanoparticles loaded on charming activated carbon adjusted by facile heat treatment

Chunhua Zhang^1,2, Guangxin Yang¹, Hong Jiang¹, Yefei Liu¹, Rizhi Chen¹, Weihong Xing¹

1 State Key Laboratory of Materials-Oriented Chemical Engineering, Nanjing Tech University, Nanjing 210009, China;
2 Changzhou Key Laboratory of Eco-Textile Technology, Changzhou Vocational Institute of Textile and Garment, Changzhou 213164, China

通讯作者: Rizhi Chen, Weihong Xing
基金资助:
The financial supports from the National Key R&D Program (2016YFB0301503), the National Natural Science Foundation of China (21776127, 21921006), the Jiangsu Province Key R&D Program (BE2018009-2), a project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and the State Key Laboratory of Materials-Oriented Chemical Engineering (ZK201902) of China are gratefully acknowledged.

Abstract

Abstract: Selective phenol hydrogenation is a green approach to produce cyclohexanone. It still remains a big challenge to prepare efficient supports of the catalysts for the phenol hydrogenation via a simple and cost-effective approach. Herein, a facile approach was developed, i.e., direct calcination of activated carbon (AC) under argon at high temperature, to improve its structure and surface properties. The modified AC materials were supported with Pd nanoparticles (NPs) to fabricate the Pd/C catalysts. The as-prepared Pd/C600 catalyst exhibits superior catalytic performance in the phenol hydrogenation, and its turnover frequency (TOF) value is 199.2 h^-1, 1.31 times to that of Pd/C-raw. The Pd/C600 catalyst presents both better hydrophobicity and more structural defects, contributing to the improved dispersibility in the reaction solution (phenol-cyclohexane), the better Pd dispersion and the smaller Pd size, which result in the enhancement of the catalytic performance. Furthermore, the as-prepared Pd/C600 catalyst shows a good recyclability.

Key words: Cyclohexanone, Phenol, Hydrogenation, Activated carbon, Catalyst

摘要： Selective phenol hydrogenation is a green approach to produce cyclohexanone. It still remains a big challenge to prepare efficient supports of the catalysts for the phenol hydrogenation via a simple and cost-effective approach. Herein, a facile approach was developed, i.e., direct calcination of activated carbon (AC) under argon at high temperature, to improve its structure and surface properties. The modified AC materials were supported with Pd nanoparticles (NPs) to fabricate the Pd/C catalysts. The as-prepared Pd/C600 catalyst exhibits superior catalytic performance in the phenol hydrogenation, and its turnover frequency (TOF) value is 199.2 h^-1, 1.31 times to that of Pd/C-raw. The Pd/C600 catalyst presents both better hydrophobicity and more structural defects, contributing to the improved dispersibility in the reaction solution (phenol-cyclohexane), the better Pd dispersion and the smaller Pd size, which result in the enhancement of the catalytic performance. Furthermore, the as-prepared Pd/C600 catalyst shows a good recyclability.

关键词: Cyclohexanone, Phenol, Hydrogenation, Activated carbon, Catalyst

Chunhua Zhang, Guangxin Yang, Hong Jiang, Yefei Liu, Rizhi Chen, Weihong Xing. Phenol hydrogenation to cyclohexanone over palladium nanoparticles loaded on charming activated carbon adjusted by facile heat treatment[J]. Chinese Journal of Chemical Engineering, 2020, 28(10): 2600-2606.

References

[1] M.M. Li, Y. Li, L. Lu, Y. Wang, Tuning the selectivity of phenol hydrogenation on Pd/C with acid and basic media, Catal. Commun. 103(2018) 88-91.
[2] S.S. Ding, C.H. Zhang, Y.F. Liu, H. Jiang, R.Z. Chen, Selective hydrogenation of phenol to cyclohexanone in water over Pd@N-doped carbons derived from ZIF-67:Role of dicyandiamide, Appl. Surf. Sci. 425(2017) 484-491.
[3] X. Zhang, Y. Du, H. Jiang, Y.F. Liu, R.Z. Chen, Matching relationship between carbon material and Pd precursor, Catal. Lett. 149(3) (2019) 813-822.
[4] J.Y. Wang, H. Zhao, X.J. Zhang, R.J. Liu, Y.Q. Hu, Oxidation of cyclohexane catalyzed by TS-1 in ionic liquid with tert-butyl-hydroperoxide, Chin. J. Chem. Eng. 16(3) (2008) 373-375.
[5] H.Z. Liu, T. Jiang, B.X. Han, S.G. Liang, Y.X. Zhou, Selective phenol hydrogenation to cyclohexanone over a dual supported Pd-Lewis acid catalyst, Science 326(5957) (2009) 1250-1252.
[6] S. Scire, S. Minico, C. Crisafulli, Selective hydrogenation of phenol to cyclohexanone over supported Pd and Pd-Ca catalysts:An investigation on the influence of different supports and Pd precursors, Appl. Catal. A Gen. 235(1) (2002) 21-31.
[7] H. Zhou, B.B. Han, T.Z. Liu, X. Zhong, G.L. Zhuang, J.G. Wang, Selective phenol hydrogenation to cyclohexanone over alkali-metal-promoted Pd/TiO₂ in aqueous media, Green Chem. 19(15) (2017) 3585-3594.
[8] X. Xu, H.R. Li, Y. Wang, Selective hydrogenation of phenol to cyclohexanone in water over Pd@N-doped carbon derived from lonic-liquid precursors, ChemCatChem 6(12) (2014) 3328-3332.
[9] E. Auer, A. Freund, J. Pietsch, T. Tacke, Carbons as supports for industrial precious metal catalysts, Appl. Catal. A Gen. 173(1998) 259-271.
[10] F.Y. Ye, D.M. Zhang, T. Xue, Y.M. Wang, Y.J. Guan, Enhanced hydrogenation of ethyl levulinate by Pd-AC doped with Nb₂O₅, Green Chem. 16(8) (2014) 3951-3957.
[11] J.Y. Li, L. Ma, X.N. Li, C.S. Lu, H.Z. Liu, Effect of nitric acid pretreatment on the properties of activated carbon and supported palladium catalysts, Ind. Eng. Chem. Res. 44(15) (2005) 5478-5482.
[12] Z.Z. Wei, Y.T. Gong, P.F. Zhang, H.R. Li, Y. Wang, Highly efficient and chemoselective hydrogenation of α,β-unsaturated carbonyls over Pd/N-doped hierarchically porous carbon, Catal. Sci. Technol. 5(1) (2015) 397-404.
[13] M.H. Tang, J. Deng, M.M. Li, X.F. Li, H.R. Li, Z.R. Chen, Y. Wang, 3D-interconnected hierarchical porous N-doped carbon supported ruthenium nanoparticles as an efficient catalyst for toluene and quinolone hydrogenation, Green Chem. 18(22) (2016) 6082-6090.
[14] X.M. Ning, Y.H. Li, B.Q. Dong, H.J. Wang, H. Yu, F. Peng, Y.H. Yang, Electron transfer dependent catalysis of Pt on N-doped carbon nanotubes:Effects of synthesis method on metal-support interaction, J. Catal. 348(2017) 100-109.
[15] D. Hulicova-Jurcakova, M. Seredych, Q.L. Gao, T.J. Bandosz, Combined effect of nitrogen-and oxygen-containing functional groups of microporous activated carbon on its electrochemical performance in supercapacitors, Adv. Funct. Mater. 19(3) (2009) 438-447.
[16] Y.Y. Bu, Z.Y. Chen, Effect of oxygen-doped C₃N₄ on the separation capability of the photoinduced electron-hole pairs generated by O-C₃N₄@TiO₂ with quasi-shell-core nanostructure, Electrochim. Acta 144(2014) 42-49.
[17] J.P. Du, C. Song, J.H. Zhao, Z.P. Zhu, Effect of chemical treatment to hollow carbon nanoparticles (HCNP) on catalytic behaviors of the platinum catalysts, Appl. Surf. Sci. 255(2008) 2898-2993.
[18] Y.Z. Xiang, L.N. Kong, P.Y. Xie, T.Y. Xu, J.G. Wang, X.N. Li, Carbon nanotubes and activated carbons supported catalysts for phenol in situ hydrogenation:Hydrophobic/hydrophilic effect, Ind. Eng. Chem. Res. 53(6) (2014) 2197-2203.
[19] G.X. Yang, J.X. Zhang, H. Jiang, Y.F. Liu, R.Z. Chen, Turning surface properties of Pd/Ndoped porous carbon by trace oxygen with enhanced catalytic performance for selective phenol hydrogenation to cyclohexanone, Appl. Catal. A Gen. 558(2019) 117306-117314.
[20] C. Wang, B.D. Li, H.Q. Lin, Y.Z. Yuan, Carbon nanotube-supported Pt-Co bimetallic catalysts for preferential oxidation of CO in a H₂-rich stream with CO₂ and H₂O vapor, J. Power Sources 202(2012) 200-208.
[21] X. Xu, M.H. Tang, M.M. Li, H.R. Li, Y. Wang, Hydrogenation of benzoic acid and derivatives over Pd nanoparticles supported on N-doped carbon derived from glucosamine hydrochloride, ACS Catal. 4(9) (2014) 3132-3135.
[22] N. Zhou, Y. Du, C.Y. Wang, R.Z. Chen, Facile synthesis of hierarchically porous carbons by controlling the initial oxygen concentration in-situ carbonization of ZIF-8 for efficient water treatment, Chin. J. Chem. Eng. 26(12) (2016) 446-452.
[23] I. Abdullahi, T.J. Davis, D.M. Yun, J.E. Herrera, Partial oxidation of ethanol to acetaldehyde over surface-modified single-walled carbon nanotubes, Appl. Catal. A Gen. 469(2014) 8-17.
[24] F.F. Jia, C. Liu, B.Q. Yang, S.X. Song, Microscale control of edge defect and oxidation on molybdenum disulfide through thermal treatment in air and nitrogen atmospheres, Appl. Surf. Sci. 462(2018) 471-479.
[25] X. Wang, J.L. Zhang, J.Y. Chen, Q.X. Ma, S.B. Su, T.S. Zhao, Effect of preparation methods on the structure and catalytic performance of Fe-Zn/K catalysts for CO₂ hydrogenation to light olefins, Chin. J. Chem. Eng. 26(4) (2018) 761-767.
[26] T.Y. Xu, Q.F. Zhang, J. Cen, Y.Z. Xiang, X.N. Li, Selectivity tailoring of Pd/CNTs in phenol hydrogenation by surface modification:Role of C-O oxygen species, Appl. Surf. Sci. 324(2015) 634-639.
[27] D.P. Qiu, N.N. Guo, A. Gao, L. Zheng, W.J. Xu, M. Li, F. Wang, R. Yang, Preparation of oxygen-enriched hierarchically porous carbon by KMnO₄ one-pot oxidation and activation:Mechanism and capacitive energy storage, Electrochim. Acta 294(2019) 398-405.
[28] J.L. Zhu, P.C. Wei, K.K. Li, S.B. He, Z.Y. Pan, S.X. Nie, Self-assembled nanofiber networks of well-separated B and N co-doped carbon as Pt supports for highly efficient and stable oxygen reduction electrocatalysis, ACS Sustain. Chem. Eng. 7(1) (2019) 660-668.
[29] S. Zhang, C.R. Chang, Z.Q. Huang, J. Li, Z.M. Wu, Y.Y. Ma, Z.Y. Zhang, Y. Wang, Y.Q. Qu, High catalytic activity and chemoselectivity of sub-nanometric Pd clusters on porous nanorods of CeO₂ for hydrogenation of nitroarenes, J. Am. Chem. Soc. 138(8) (2016) 2629-2637.

Phenol hydrogenation to cyclohexanone over palladium nanoparticles loaded on charming activated carbon adjusted by facile heat treatment

Phenol hydrogenation to cyclohexanone over palladium nanoparticles loaded on charming activated carbon adjusted by facile heat treatment

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jinlong Liu, Chenye Wang, Xingrui Wang, Chen Zhao, Huiquan Li, Ganyu Zhu, Jianbo Zhang. Reconstruction and recovery of anatase TiO₂ from spent selective catalytic reduction catalyst by NaOH hydrothermal method [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 53-60.
[2]	Yifan Jiang, Bingqi Xie, Jisong Zhang. Highly reactive and reusable heterogeneous activated carbons-based palladium catalysts for Suzuki-Miyaura reaction [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 165-172.
[3]	Peipei Ai, Huiqing Jin, Jie Li, Xiaodong Wang, Wei Huang. Ultra-stable Cu-based catalyst for dimethyl oxalate hydrogenation to ethylene glycol [J]. Chinese Journal of Chemical Engineering, 2023, 60(8): 186-193.
[4]	Yuehua Liu, Lili Chen, Shoujun Liu, Song Yang, Ju Shangguan. Role of iron-based catalysts in reducing NO_x emissions from coal combustion [J]. Chinese Journal of Chemical Engineering, 2023, 59(7): 1-8.
[5]	Fei Li, Xuemei Wang, Pengze Zhang, Qinqin Wang, Mingyuan Zhu, Bin Dai. Nitrogen and phosphorus co-doped activated carbon induces high density Cu⁺ active center for acetylene hydrochlorination [J]. Chinese Journal of Chemical Engineering, 2023, 59(7): 193-199.
[6]	Qunfeng Zhang, Bingcheng Li, Yuan Zhou, Deshuo Zhang, Chunshan Lu, Feng Feng, Jinghui Lv, Qingtao Wang, Xiaonian Li. Regulation of the selective hydrogenation performance of sulfur-doped carbon-supported palladium on chloronitrobenzene [J]. Chinese Journal of Chemical Engineering, 2023, 58(6): 69-75.
[7]	Masoumeh Sheikh Hosseini Lori, Mohammad Delnavaz, Hoda Khoshvaght. Synthesizing and characterizing the magnetic EDTA/chitosan/CeZnO nanocomposite for simultaneous treating of chromium and phenol in an aqueous solution [J]. Chinese Journal of Chemical Engineering, 2023, 58(6): 76-88.
[8]	Chaobo Zhang, Xiaoyong Yang, Jian Dai, Wenxia Liu, Hang Yang, Zhishan Bai. Efficient extraction of phenol from wastewater by ionic micro-emulsion method: Anionic and cationic [J]. Chinese Journal of Chemical Engineering, 2023, 58(6): 137-145.
[9]	Jiajia Chen, Xinyu Lu, Dandan Wang, Pengcheng Xiu, Xiaoli Gu. Effective depolymerization of alkali lignin using an attapulgite-Ce_0.75Zr_0.25O₂(ATP-CZO)-supported cobalt catalyst in ethanol/isopropanol media [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 50-62.
[10]	Bin Gao, Junwen Chen, Qi Zuo, Hongyan Wang, Wenlin Li. The critical role of Zr in controlling the activity of Pd/Beta on the hydrogenation of phenol to cyclohexanone [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 79-87.
[11]	Linlin Su, Meijun Chen, Li Gong, Hua Yang, Chao Chen, Jun Wu, Ling Luo, Gang Yang, Lulu Long. Boost activation of peroxymonosulfate by iron doped K_2-xMn₈O₁₆: Mechanism and properties [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 88-97.
[12]	Qi Yang, Weikang Dai, Maoshuai Li, Jie Wei, Yi Feng, Cheng Yang, Wanxin Yang, Ying Zheng, Jie Ding, Mei-Yan Wang, Xinbin Ma. Enhanced selective hydrogenation of glycolaldehyde to ethylene glycol over Cu⁰-Cu⁺ sites [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 141-150.
[13]	Bingxiao Feng, Lining Hao, Chaoting Deng, Jiaqiang Wang, Hongbing Song, Meng Xiao, Tingting Huang, Quanhong Zhu, Hengjun Gai. A highly hydrothermal stable copper-based catalyst for catalytic wet air oxidation of m-cresol in coal chemical wastewater [J]. Chinese Journal of Chemical Engineering, 2023, 57(5): 338-348.
[14]	Shujun Peng, Song Lei, Sisi Wen, Jian Xue, Haihui Wang. A Ruddlesden–Popper oxide as a carbon dioxide tolerant cathode for solid oxide fuel cells that operate at intermediate temperatures [J]. Chinese Journal of Chemical Engineering, 2023, 56(4): 25-32.
[15]	Da Ke, Minjia Wang, Jiancheng Ruan, Xinzhi Chen, Shaodong Zhou. Efficient, continuous oxidation of durene to pyromellitic dianhydride mediated by a V-Ti-P ternary catalyst: The remarkable doping effect [J]. Chinese Journal of Chemical Engineering, 2023, 55(3): 156-164.