Research progress on the heterogeneous photocatalytic selective oxidation of benzene to phenol

doi:10.1016/S1872-2067(23)64430-4

Chinese Journal of Catalysis ›› 2023, Vol. 49: 16-41.DOI: 10.1016/S1872-2067(23)64430-4

Research progress on the heterogeneous photocatalytic selective oxidation of benzene to phenol

Mengistu Tulu Gonfa^a, Sheng Shen^a^,^*(), Lang Chen^a^,^*(), Biao Hu^a, Wei Zhou^a, Zhang-Jun Bai^a, Chak-Tong Au^b, Shuang-Feng Yin^a^,^*()

^aAdvanced Catalytic Engineering Research Center of the Ministry of Education, State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, Hunan, China
^bCollege of Chemical Engineering, Fuzhou University, Fuzhou 350002, Fujian, China

Received:2023-02-23 Accepted:2023-04-10 Online:2023-06-18 Published:2023-06-05
Contact: ^*E-mail: sshen@hnu.edu.cn (S. Shen), huagong042cl@163.com (L. Chen), sf_yin@hnu.edu.cn (S. F. Yin).
About author:Sheng Shen received her bachelors’ degree from Wuhan University, China, in 2012. Then she moved to the United States and received her Ph.D. degree in chemistry from the University of Georgia, working on the electrodepostion of semiconductor materials under the supervision of Prof. John L. Stickney. She is currently an associate professor at Hunan University, China, where she focuses on the development of efficient photoelectrodes for solar based energy harvesting and conversion.
Lang Chen received his bachelors’ degree from Henan University of Science and Technology in 2008 and then obtained his Ph.D. in Hunan University under the supervisor of Prof. Shuang-Feng Yin. He is currently an associate professor in Hunan University. His research interests focus on the design, synthesis, and application of efficient heterogeneous photocatalysts/photo-electro-catalyst.
Shuang-Feng Yin obtained his bachelors’ degree in 1996 from Beijing University of Chemical Technology. He subsequently received his Ph.D. from Tsinghua University in 2003. He was promoted to full Professor in Hunan University in 2006. He worked as a senior visiting scholar in the Hong Kong Baptist University and Japan Institute of Integrated Industrial Technology from 2008 to 2009. He is Distinguished Young Scholars Recipients of the National Natural Science Foundation of China (2017). His research interests focus on photo/electrocatalytic energy conversion and C‒H bond activation.
Supported by:
National Natural Science Foundation of China(22008059);National Natural Science Foundation of China(21938002);National Natural Science Foundation of China(21725602);National Natural Science Foundation of China(21975069)

Abstract

Abstract:

Phenol is important for the manufacture of phenolic chemicals. The current cumene process for phenol production requires harsh conditions and suffers from unwanted side products. Nowadays, the one step conversion of benzene to phenol has received much attention. However, because of the obscurity in benzene C(sp²)-H bond activation and the easy oxidation of phenol, the direct oxidation of benzene to phenol is challenging. As an alternative, the photocatalytic selective oxidation of benzene into phenol under mild conditions is considered promising. In this review, we systematically summarize the recent advance of heterogeneous photocatalytic oxidation of benzene, including those of design principles and various modification strategies, mechanistic understanding determined based on in situ characterization and density functional theory calculation, factors affecting kinetics of the reaction, reactor design and photocatalyst deactivation. It is envisaged that photocatalysts made up of single atoms, layered double hydroxides, and metal clusters are good candidates. At the end of this article, the perspective of catalyst design and strategies for the exploration of reaction mechanism are discussed, emphasizing on the use of state-of-the-art techniques. Moreover, the design of photocatalytic reactors for the realization of the photocatalytic process is considered.

Key words: Benzene, Phenol, Direct oxidation, Photocatalyst, Photocatalytic reactor

Mengistu Tulu Gonfa, Sheng Shen, Lang Chen, Biao Hu, Wei Zhou, Zhang-Jun Bai, Chak-Tong Au, Shuang-Feng Yin. Research progress on the heterogeneous photocatalytic selective oxidation of benzene to phenol[J]. Chinese Journal of Catalysis, 2023, 49: 16-41.

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Figures/Tables 37

Fig. 1. (a) Global phenol market demand by its derivatives in 2019. Adapted with permission from Ref. [3]. Copyright 2021, American Chemical Society. Representation of catalytic processes of benzene oxidation to phenol: (b) Sulfonation; (c) Chlorination; (d) Toulene benzoic acid process; (e) Cumene process; (f) Direct conversion to phenol [9].

Fig. 2. (a) Heterogeneous catalysis process approaches. (b) Schematic process of selective benzene oxidation to phenol.

Fig. 3. Band-edges, band gap energy positions of some semiconductors and relative redox potentials of the couples used to generate reactive oxygen species.

Fig. 4. Mechanisms of benzene oxidation to phenol by reactive oxygen species.

Fig. 5. Proposed reaction mechanism of the photocatalytic hydroxylation of benzene in (a) neutral or acidic conditions and (b) basic conditions. (c,d) Schematic of isotopic effect. Adapted with permission from Ref. [50]. Copyright 2012, American Chemical Society.

Fig. 6. (a) In situ ESR spectra of C16Qu-PW in reaction system (containing benzene 1.28 mmol, acetonitrile 10 mL, water 1 mL). (b) UV-vis spectra of recovered C16Qu-PW with different exposure time in air. (c) Proposed reaction route for C16Qu-PW photocatalyzed selective oxidation of benzene to phenol. Adapted with permission from Ref. [63]. Copyright 2021, Elsevier.

Fig. 7. Optimized structures of reactant, TS and product among benzene, H2O and H2O2 in the absence (a) and the presence (b) of Pt3 as co-catalyst for the hydroxylation of benzene to phenol. (c) Energy potentials for intrinsic reaction coordinates. Adapted with permission from Ref. [67]. Copyright 2020, MDPI. The author(s) and Catalysts published by the MDPI under the terms of the Creative Commons CC BY license (https://creative commons.org/licenses/by-ncnd/4.0/).

Fig. 8. Model for simulating the interface between g-C3N4-CuWO4 heterojunction for geometry optimization before optimization (a) and after (b) optimization. (c) Projected density of states (PDOS) of the pure g-C3N4 surface and g-C3N4-CuWO4 heterojunction surface from top to bottom, the dotted line represents the Fermi level. (d,e) Γ-point orbital-isoamplitude surface of the respective orbitals. Adapted with permission from Ref. [68]. Copyright 2022, Royal Society of Chemistry.

Fig. 9. Fundamental considerations for photocatalyst design for selective benzene oxidation to phenol.

Fig. 10. Catalytic research trends of one-step selective benzene oxidation to phenol.

Fig. 11. (a) UV/Vis diffuse-reflectance spectra of Au@TiO2-microsphere composites. (b) Visible-light-induced catalytic oxidation of benzene with Au@TiO2 of 1 wt%-3 wt% of Au. (c) Mechanism of photocatalytic reaction for Au/TiO2 composed photocatalyst. Adapted with permission from Ref. [90]. Copyright 2011, Royal Society of Chemistry. (d) TEM images of 1Au/TV2, HRTEM images of 1Au/TV2, 3Au/TV2, SEM image of 1Au/TV2. (e) Possible mechanism of the photocatalytic oxidation of benzene to phenol proposed on the basis of experimental observations for Au/TV2. Adapted with permission from Ref. [22]. Copyright 2014, American Chemical Society.

Fig. 12. (a) Reaction scheme of surface modification of MCF by silylation. (b) Titanium oxide entrapped in cage-like mesopores of hydrophobically modified MCF for the hydroxylation of benzene. (c) Images of water contact angles on catalyst samples. Adapted with permission from [92]. Copyright 2011, Elsevier.

Fig. 13. Proposed reaction mechanisms for phenol production over Pt/WO3 (a) and Pt/TiO2 (b) photocatalysts. Adapted with permission from Ref. [16]. Copyright 2014, Royal Society of Chemistry. (c) Proposed mechanism of photocatalytic benzene hydroxylation to phenol over the hierarchical heterostructure of Bi2WO6/CdWO4. Adapted with permission from Ref. [102]. Copyright 2018, Elsevier.

Table 1 Summary of photocatalytic performances based on hybridized TiO2 for the selective transformation of benzene to Phenol.

Oxidant	Catalyst	Reaction condition	Yield (%)	Sel. (%)	Ref.
H₂O	Au@TiO₂	300 W Xe lamp (λ ≥ 400 nm), RT, 3 h, H₂O (50 mL), catal. (50 mg), benzene (0.07 mL)	63	91	[90]
H₂O₂	Au/Ti_0.98V_0.02O₂	UV light (200 nm ≤ λ ≤ 400 nm), RT, 18 h, CH₃CN (2 mL), H₂O₂ (25%, catal. (30 mg), 2 mL), benzene (1 mL)	16	88	[22]
H₂O₂	Pd/CeO₂/TiO₂	Xe lamp λ > 420 nm, 80 °C, 10 h, CH₃CN (10 mL), catal. (100 mg), benzene (1.36 mL), benzene:H₂O₂ (molar ratio) = 1:5	69.4	95	[94]
N₂O	Pt/TiO₂	450 W Xe lamp (λ > 300 nm), 4 h, benzene: H₂O:CH₃CN (0.05 mL: 24 mL: 1 mL), PH (3.5), air, catal. (25 mg), benzene (0.05 mL)	2	100	[50]
H₂O	Cu/Ti/CNT	Low pressure Hg light source, (λ > 254 nm), H₂O (20 mL), catal. (100 mg), benzene (20 mL)	52	76	[63]
	TiO₂/MCF	300W Xe lamp (λ > 320 m), 2 h, CH₃CN (0.3 mL), and H₂O (29.7 mL), catal. (30 mg), benzene (2.6 × 10^-4 mL)	—	50	[64]
	Pt/TiO₂	300 W Xe lamp, RT, 3 h, H₂O (1 mL), catal. (20 mg), benzene (1 mL).	9	75	[65]
H₂O₂	FeVCu/TiO₂	Black light blue fluorescent bulb, 30 °C, 4 h, CH₃CN (40 mL), catal. (10 mg), benzene:H₂O₂ = 0.5	9.7	52	[80]
	Ti_0.98Fe_0.01Cr_0.01O₂	450 W Hg lamp (200 nm ≤ λ ≤ 400 nm), RT, 12 h, CH₃CN (2 mL), H₂O₂ (25%, 2 mL), catal. (30 mg), benzene (1 mL)	25.2	90	[79]

Table 2 Summary of photocatalytic performances based on hybridized tungsten compounds for the selective transformation of benzene to Phenol.

Oxidant	Catalyst	Reaction condition	Yield (%)	Sel. (%)	Ref.
O₂	C₁₆Qu-PW (IL-POM)	500 W Hg lamp (λ ≤ 365 nm), room temp. 10 h, CH₃CN (10 mL) and H₂O (1 mL), air, catal. (0.15 mg), benzene (0.1 mL)	21	99	[48]
O₂	Bi₂WO₆/CdWO₄	300 W Xenon lamp (λ ≥ 400 nm), 3 h, H₂O (0.1 mL) and CH₃CN (3 mL), O₂ (3 mL min^‒1), catal. (50 mg), benzene (0.04 mL)	5.8	99	[49]
H₂O	Pt/WO₃	300 W Xe lamp (400 < λ < 500 nm), 4 h, H₂O (7.5 mL), catal. (10 mg), benzene (0.002 mL)	—	79	[16]
H₂O	WO₃QD	Hg lamp (270 < λ < 410 nm), 40 h, H₂O (29 mL), catal. (10 mg), benzene (0.1 mL).	8.3	99	[66]

Fig. 14. (a) Illustration of the structural benefits of FeVO4@OS for photocatalytic benzene hydroxylation reaction. (b) ICP results of iron leaching across five runs. (c) Selective hydroxylation of benzene to phenol over FeVO4 and silylated FeVO4. Adapted with permission from Ref. [104]. Copyright 2021, Royal Society of Chemistry.

Fig. 16. (a) Topological view of MIL-100 with MTN-type zeolitic architecture and view of the structure of MIL-68 involving two types (hexagonal and trigonal) of channels running through the c-axis. (b) Possible reaction mechanism for the photocatalytic benzene hydroxylation over MIL-100(Fe). Adapted with permission from Ref. [106]. Copyright 2021, American Chemical Society. (c) Preparation of the NH2-MIL-88/PMo10V2-3 catalyst, Adapted with permission from Ref. [108]. Copyright 2021, Royal Society of Chemistry.

Fig. 17. (a) Possible reaction mechanism for photocatalytic benzene hydroxylation over CNTs@FcPOP. Adapted with permission from Ref. [108]. Copyright 2021, Royal Society of Chemistry. (b) Proposed reaction mechanism for benzene hydroxylation by Fc-CN.

Table 3 Summary of photocatalytic performances based on hybridized iron compounds for the selective transformation of benzene to phenol.

Catalyst	Reaction condition	Yield (%)	Sel. (%)	Ref.
NH₂-MIL-88/PMo₁₀V₂-₃	5 W LED (≥ 320 nm), 60 °C, 3 h, CH₃CN (2 mL), CH₃COOH (3 mL), H₂O₂ (1 mL), catal. (50 mg), benzene (1 mL)	12.4	99	[59]
MIL-68 (Fe)	300 W Xe lamp (λ ≥ 420 nm), 8 h, solvent (4 mL), H₂O₂ (30%, 0.039 mL), catal. (10 mg), benzene (0.044 mL)	—	98	[53]
CNTs@Fc-POP	300 W, 4 h, CH₃CN (4 mL), H₂O (4 mL), H₂O₂ (0.8 mL), catal. (50 mg), benzene (0.2 mL)	25	—	[60]
FeVO₄@TMOS	300 W Xe lamp (λ > 420 nm), 24 °C, CH₃CN (3 mL), H₂O (3 mL), H₂O₂ (30%, 2 mL), catal. (30 mg), benzene (0.1 mL)	20	98	[57]
FePc	Hg lamp, RT, 6 h, CH₃CN (5 mL), H₂O₂ (3 mL), catal. (30 mg), benzene (1 mL),	15.2	99	[111]
ZFO@C-2	300 W Xe lamp (λ < 420 nm), RT, CH₃CN (3 mL), H₂O (3 mL), H₂O₂ (30 wt%, 0.5 mL), catal. (30 mg), benzene (0.1 mL).	15.5	99.4	[60]

Fig. 18. Schematic of the synthesis of g-C3N4 by thermal polymerization of melamine, cyanamide, dicyanamide, urea, and thiourea [118].

Fig. 19. (a) Ultraviolet-visible diffuse reflectance spectra (UV-vis DRS) of h-BCNx and h-BN. (b) Tauc plots of h-BN and h-BCNx by UV-vis DRS. (c) Proposed mechanism for photocatalytic hydroxylation of benzene by h-BCN combined with FeCl3. (d) Time course of catalytic performance for benzene oxidation to phenol under visible light irradiation (λ ≥ 420 nm). (e) Cyclic runs in the photocatalytic oxidation of benzene to phenol. Adapted with permission from Ref. [120]. Copyright 2019, Elsevier.

Fig. 20. (a) Proposed mechanism for the oxidation of benzene by the Au-Pd/g-C3N4 catalyst under visible light irradiation. Adapted with permission from Ref. [121]. Copyright 2018, American Chemical Society. Copyright 2018, American Chemical Society. (b,c) Optical absorption spectra of FeCl3/mpg-C3N4. (d) Possible reaction mechanism for the catalytic oxidation of benzene by FeCl3/mpg-C3N4 hybrids. Adapted with permission from Ref. [12]. Copyright 2013, Royal Society of Chemistry.

Fig. 21. (a) Stacked g-C3N4 sheets function as an all-organic solid-state photocatalyst promoting redox reactions with visible light. (b) Chemical interaction of benzene and defective g-C3N4 via HOMO-LUMO hybridization of melem and benzene. Adapted with permission from Ref. [123]. Copyright 2009, American Chemical Society.

Fig. 22. (a) N2 adsorption-desorption isotherms of TS-1 and Fe-CN/TS-1-2. The inset is the corresponding BJH pore-size distribution curves. (b) Electrochemical impedance in the dark. (c) STEM images of Fe-CN/TS-1 (a,b), elemental mapping images of C, N, and Fe. Adapted with permission from Ref. [125]. Copyright 2014, Elsevier.

Fig. 24. (a) Illustration of the preparation of SA-Cu-TCN. (b,c) Calculated charge difference surfaces of the Cu-N3 and Cu-N4 coordination systems. Adapted with permission from Ref. [127]. Copyright 2020, Wiley-VCH.

Table 4 Summary of photocatalytic performances based on hybridized g-C3N4 compounds for the selective transformation of benzene to Phenol.

Catalyst	Reaction condition	Yield (%)	Sel. (%)	Ref.
FeCl₃/mpg-C₃N₄	100 W Hg lamp (λ > 420 nm), 60 °C, 4 h, H₂O (2 mL) and CH₃CN (2 mL), H₂O₂ (30%, 0.255 mL), catal. (25 mg), benzene (0.39 mL).	—	97	[12]
h-BCN/FeCl₃	300 W Xe, lamp (λ > 420 nm), 60 °C, 2 h, H₂O (4 mL) and CH₃CN (4 mL), H₂O₂(0.15 mL), catal. (50 mg) with FeCl₃ (3 wt%), benzene (0.8 mL)	14	88	[51]
Fe@NC	60 °C, 12 h, CH₃CN (3 mL), H₂O (3 mL), H₂O₂ (2 mL), catal. (30 mg), benzene (0.25 mL)	14.5	95	[121]
Au-Pd/g-C₃N₄	100 W Hg lamp, light source 10 cm, 50 °C, 2 h, CH₃CN (5 mL), H₂O₂ (25%, 2 mL), catal. (10 mg), benzene (1 mL).	26	100	[52]
Fe-g-C₃N₄/SBA-15	500 W Xe lamp (λ > 420 nm), 60 °C, 4 h, H₂O (4 mL), C₂H₅OH (5 mL) and CH₃CN (4 mL), H₂O₂ (30%, 0.51 mL), catal. (50 mg), benzene (0.8 mL).	—	21	[54]
Fe-g-C₃N₄-LUS-1	125 W Mercury lamp, 60 °C, 4 h, CH₃CN (4 mL), H₂O₂ (30%, 0.5 mL), catal. (0.05 g), benzene (1 mL).	5	64	[55]
Fe-CN/TS-1	300 W Xe lamp (λ > 420 nm), 60 °C, 4 h, CH₃CN (4 mL) and H₂O (4 mL), H₂O₂ (30%, 0.51 mL), catal. (50 mg), benzene (0.8 mL).	10	18	[56]
SA-Cu-TCN	Visible light (λ > 420 nm), 50 °C, 12 h, CH₃CN (6 mL), H₂O₂ (6 mL, 30 wt%), catal. (20.0 mg), benzene (0.4 mL).	—	99.9	[35]
Ni-CuWO₄/g-C₃N₄	Sun light, 0.25 h, H₂O (0.2 mL), H₂O₂ (30%), (0.5 mL), catal. (20 mg), benzene (1 mL)	81.5	98.5	[62]

Fig. 27. Effect of solvents on catalyst performance [146].

Fig. 29. Classification of photocatalytic reactors based on attributes like photon, catalyst, and reactor type [152].

Fig. 30. Two-phase membrane reactor: non membrane zone (1), lamp (2), non-membrane zone stirred solution (3), peristaltic pump that withdraws the solution from the photocatalytic zone to the separation zone (4), permeation module (5), aqueous phase compartment (6), Organic strip containing compartment (7). Adapted with permission from Ref. [137]. Copyright 209, Elsevier.

Fig. 32. (a) Representation of photocatalyst modification strategies. (b) Categories of photocatalyst design strategies.

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Research progress on the heterogeneous photocatalytic selective oxidation of benzene to phenol

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