One-Step Catalytic or Photocatalytic Oxidation of Benzene to Phenol: Possible Alternative Routes for Phenol Synthesis?
Abstract
:1. Introduction
- (1)
- PHENOLIC RESINS: by the reaction of phenol or substituted phenol with formaldehyde, phenol–formaldehyde resins or phenolic resins can be obtained. The first example was Bakelite as a commercial synthetic resin [2].
- (2)
- POLYCARBONATES (a very pure phenol feed is required): polycarbonates are thermoplastic polymers containing carbonate groups in their chains [3].
- (3)
- EPOXY RESINS: epoxy phenolic resins are resins modified at the phenolic hydroxyl group to include an epoxide functional group. This addition increases the ability of the resin to crosslink, creating a stronger polymer [4].
- (4)
- INTERMEDIATE FOR CAPROLACTAM (nylon production): caprolactam is a monomer for nylon production. Among the routes for its manufacture, one is via cyclohexanone and cyclohexanone oxime. Cyclohexanone can be prepared either from phenol or from cyclohexane. The phenol route is a two-stage process, in which the first stage foresees the reaction among phenol and hydrogen in the presence of a nickel catalyst at around 180 °C to form cyclohexanol, subsequently dehydrogenated at around 400 °C in the presence of a copper catalyst to yield the cyclohexanone [5].
2. Homogeneous and Heterogeneous Catalysts for the One-Step Catalytic Oxidation of Benzene to Phenol in Liquid Phase
3. Homogeneous and Heterogeneous Photocatalysts for the One-Step Catalytic Oxidation of Benzene to Phenol in Liquid Phase
- (1)
- hydroxylation of benzene with water;
- (2)
- coupling of benzene;
- (3)
- reduction of the produced phenol and successive oxidation of the produced cyclohexanol to cyclohexanone;
- (4)
- decomposition of benzene with water.
4. Concluding Remarks and Perspectives
- the immobilization of the catalysts or photocatalysts on macroscopic supports (i.e., the development of structured catalysts) to avoid the separation of catalyst powders from the liquid phase containing phenol at the end of the oxidation step;
- the development of structured catalysts or photocatalysts with high stability and which are easily recyclable;
- the development of novel selective oxidation systems (e.g., highly efficient photoanodes for the photoelectrocatalytic oxidation of benzene to phenol);
- the design of efficient and low-cost systems to recover the produced phenol from the liquid phase.
Author Contributions
Funding
Conflicts of Interest
References
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Component | ∆H° at 298 K (kJ/mol) | ∆G° at 298 K (kJ/mol) | |
---|---|---|---|
Reagent | Benzene (l) | 48.99464 | 124.34848 |
Benzene (g) | 82.92688 | 129.66216 | |
Oxidant | H2O2 (l) | −136.10552 | −105.47864 |
N2O (g) | 82.04824 | 104.1816 | |
O2(g) | |||
H2(g) | |||
Product | Phenol (s) | −165.01696 | −50.4172 |
Phenol (g) | −96.35752 | −32.88624 | |
H2O | −285.82996 | −237.178408 |
Catalyst | t (h) | T (°C) | P (atm) | Operating Conditions | Benzene Conversion (%) X | Phenol Yield (%) η | Selectivity to Phenol (%) Sp | Ref. |
---|---|---|---|---|---|---|---|---|
CuO/Al2O3 | - | 80 | 1 | 80 vol% acetic acid, benzene: 22.5 mmol; ascorbic acid: 4 mmol. | - | 1.2 | - | [47] |
V/Al2O3 | - | 30 | 4 | 80 vol% acetic acid; benzene: 5.6 mmol; ascorbic acid: 1 mmol. | - | 8.4 | - | [48] |
V2O5–Al2O3 | 6 | 60 | 1 | Catalyst: 0.2 g (14 wt%V2O5); benzene: 1.46 mmol; acetonitrile: 4 mL; H2O2: 11.68 mmol. | 13 | - | 100 | [44] |
Fe3+–Al2O3 | 6 | 60 | 1 | Catalyst: 0.20 g; acetonitrile: 4 mL; benzene: 1.24 mmol; H2O2: 6 mmol. | 12 | 12 | - | [21] |
Ru/SiO2 Rh/SiO2 Pd/SiO2 Ir/SiO2 Pt/SiO2 | - | 20 | 1 | Catalyst: 0.5 wt.-% metal/SiO2:1.0 g; H2/O2 = 3; benzene: 20 mL; acetic acid: 25 mL. | - | - | 0 99.7 88.2 64.5 63.9 | [49] |
Ru/SiO2 Rh/SiO2 Pd/SiO2 Ir/SiO2 Pt/SiO2 | - | 60 | 1 | Catalyst: 0.5 wt.-%; metal: 20wt.-%; V2O5/SiO2: 1.0 g; H2/O2: 3; benzene: 20 mL; acetic acid: 25 mL. | - | - | 100 100 99.7 100 100 | [49] |
0.1%V/SiO2 | - | 70 | 1 | Catalyst: 0.204 g; benzene: 40 mmol benzene/H2O2 mole ratio: 1; acetonitrile: - mL. | 10 | - | 81 | [50] |
Fe5V2.5Cu2.5/TiO2 | 4 | 30 | 1 | Catalyst: 0.2 g; benzene: 11 mL; benzene/H2O2 mole ratio: 0.5; acetonitrile: 40 mL. | 9.8 | 7.154 | 73 | [51] |
FePt/TiO2 (5%;1%) | 4 | 30 | 1 | Catalyst: 0.2 g; benzene: 11 mL; benzene/H2O2 mole ratio: 0.5; acetonitrile: 40 mL. | 6.5 | 5.92 | 91 | [52] |
V/MCM-41 [Si/V = 1/9.4] | 6 | 60 | 1 | Catalyst: 0.05 g; benzene: 6 mL; benzene/H2O2 mole ratio: 1/1.15; acid acetic: 6 mL. | 1.4 | - | 93 | [53] |
4%Cu/MCM-41 | 1.6 | 30 | 1 | Catalyst: 0.05 g; benzene: 1 mL; benzene/H2O2 mole ratio: 1/2; acid acetic: 7.5 mL. | 21 | 19.7 | 94 | [18] |
Ti-MCM-41 [Si/Ti = 25] | 3.5 | 65 | 1 | Catalyst: 0.05 g; benzene: 0.045 mol; benzene/H2O2 mole ratio: 1/3; acetone: 15 g. | 98 | - | >95 | [54] |
VOx/FeSBA-15 VOx/CoSBA-15 VOx/NiSBA-15 VOx/CrSBA-15 VOx/MnSBA-15 VOx/ZnSBA-15 VOx/AgSBA-15 VOx/CuSBA-15 | 5 | 80 | 1 | Catalyst: 0.05 g; benzene: 1mL; solvent (acetic acid/H2O v/v): 36 mL; ascorbic acid: 11.9 mmol. | - | 12.8 11.3 15.8 10.2 17.2 17.9 18.1 24.7 | - | [55] |
Fe/SBA-16 | 8 | 65 | 1 | Catalyst: 0.1 g; benzene: 1 mL; H2O2: 2 mL; acetonitrile: 20 mL; | 12.1 | 11.7 | 96.4 | [56] |
1.4wt%Cu(II)-NaY | 6 | 70 | 1 | Catalyst: 0.025 g; benzene: 0.02 mol; H2O2: 0.02 mol. | 33.2 | - | 100 | [57] |
Graphene (CCG) | 16 | 60 | 1 | Catalyst: 0.02 g; benzene: 130 mg; H2O2: 2.4 mL; acetonitrile: 1.2 mL. | 17.8 | 17 | > 99 | [58] |
4.2V/NC-600 | 3 | 70 | 1 | Catalyst: 0.02 g; benzene: 0.4 mL; H2O2: 1.4 mL; acetic acid: 5 mL. | 27.7 | 26.8 | 96.7 | [59] |
4V/MCN-S | 3 | 70 | 1 | Catalyst: 0.02 g; benzene: 0.4 mL; H2O2: 1.4 mL; acetic acid: 5 mL. | 38.2 | 36.7 | 96.1 | [60] |
Fe3O4/CMK-3 | 4 | 60 | 1 | Catalyst: 0.02 g; benzene: 1 mL; H2O2: 2 mL; acetonitrile: 6 mL. | 18 | - | 92 | [61] |
10V/mp-C3N4 | 3 | 60 | 1 | Catalyst: 0.06 g; benzene: 1.5 mL; H2O2: 3 mL; acetonitrile: 6 mL. | 18 | 18 | 93 | [62] |
Ce0.07-0.07V-g-C3N4 | 4 | 70 | Catalyst: 0.04 g; benzene: 1 mL; H2O2: 3.5 mL; acid acetic: 10 mL. | 33.7 | 32.3 | 95.9 | [63] | |
Cr/g-C3N4-300 | 7 | 65 | Catalyst: 0.04 g; benzene: 3.36 mmol; H2O2: 1.2 mL; acetonitrile: 2 mL. | 31.1 | 30.9 | 99.5 | [64] | |
FeCl3/eg-C3N4 | 3 | 60 | 1 | Catalyst: 0.05 g; benzene: 11.2 mmol; H2O2: 3 mL; acetonitrile: 5 mL. | 22 | 22 | 99 | [65] |
Fe-TBAPy | 3 | 60 | 1 | Catalyst: 0.05 g; benzene: 11.2 mmol; H2O2: 3 mL; acetonitrile: 5 mL. | - | 64.5 | 92.9 | [66] |
Cu-SA/HCNS | 12 | 60 | Catalyst: 0.05 g; benzene: 0.4 mL; H2O2: 6 mL; acetonitrile: 6 mL. | 86 | - | 96.7 | [67] |
Photocatalyst | t * (h) | Light Source | Operating Conditions | Benzene Conversion (%) X | Phenol Yield (%) η | Selectivity to Phenol (%) Sp | Ref. |
---|---|---|---|---|---|---|---|
nTiO2 mTiO2 mTiO2 | 2 2 6 | Hg lamp λ > 320 nm | Photocatalyst: 10 mg + nitrogen flow H2O: 10 mL benzene: 20 μmol pH 7 | 26 23 42 | 2 19 34 | 8 83 81 | [88] |
TiO2 | 6 | 450 W Xe arc lamp | Photocatalyst:25 mg Benzene: 20 mM [Fe3+]: 1.47 mM [Ag+ ]: 0.98 mM H2O2: 9.4 mM | - | <1 | 96 | [9] |
Pt-TiO2 | 1.5 | λ > 385 nm | Photocatalyst: 0.2 g benzene: 0.05 mL H2O: 4 mL | - | 2.1 | 91 | [89] |
Au-P25: in 100 kPa air in 230 kPa CO2 P25: in 100 kPa air in 230 kPa CO2 | 24 | Solar simulator | Photocatalyst: 60 mg aqueous benzene solution: 20 mL C0benzene: 600 ppm dry ice:0-200 mg closed container: 50 mL | 13 14 34 31 | 8 13 7 7 | 62 89 21 22 | [90] |
Au-V-TiO2 | 18 | 400 W Hg lamp λ = 200−400 nm | Photocatalyst: 30 mg CH3CN: 2 mL benzene: 1 mL (25 wt%) H2O2: 2 mL | 18 | 16 | 88 | [86] |
Pt/WO3-K | a 1 b 4 e 0.25 | 300 W Xe lamp λ>300 nm c λ>400 nm | Photocatalyst: 50 mg C0benzene: 2.5 mmolL−1 H2O: 7.5 mL 279 K O2 dAr | [91] | |||
Pt/WO3-K | |||||||
WO3-K | 16.4 b | 84.6 b | |||||
Pt/WO3-Y | 40.6a | 58.8 a | |||||
Pt/WO3-S | 32.4 a | 48.7 a | |||||
Pt/TiO2-P25 | |||||||
TiO2-P25 | 85.2 b | 20.6 b | |||||
Pt/TiO2-M | 43 a | 31 a | |||||
Pt/TiO2-J. | |||||||
Fe3+ impregnated TiO2 | 1–2 | 125 W Hg lamp UV light | Photocatalyst: 50 mg aqueous benzene (1 to 20 mM): 5 mL | - | 9–15 | 80–86 | [87] |
Fe-Cr-TiO2 | 12 | 450 W mercury lamp λ = 200–400 nm | Photocatalyst: 30 mg CH3CN: 2 mL benzene: 1 mL (25 wt%) H2O2: 2 mL | 28 ± 0.5 | 25.2 ± 0.5 | 90 ± 0.5 | [86] |
Fe-V-Cu supported on TiO2 | 4 | black light blue fluorescent bulb (8W) | Photocatalyst: 0.2 g benzene: 11 cm3 benzene/H2O2 mole ratio: 0.5 (30 wt%) H2O2: 30 cm3 solvent: 40 cm3 acetone a, acetonitrile b, pyridine c ascorbic acid: 0.5 | 18.61 a 14.27 b 7.9 c | 9.68 a 9.7 b 7.11 c | 52 a 68 b 90 c | [92] |
LT-550 LT-750 Cu(OH)2/LT-550 Cu(OH)2/LT-750 Cu(OH)2/LT-750a Cu(OH)2/LT-750b | 6 | UV light | Photocatalyst: 5 mg Benzene: 100 μL CH3CN: 500 μL H2O: 13 mL (30 wt%) H2O2: 87 μL | 38.7 47.1 42 49.9 a 55.0 b 41 | 36.3 45.2 40.7 48.4 a 47.9 b 36.5 | 94 96 97 97 a 87 b 89 | [93] |
CuPd/g-C3N4 | 1.5 | solar simulator | Solution A: -photocatalyst: 20 mg - deionized water: 30 mL Solution B: - benzene: 0.5 mL - acetonitrile: 30 mL. (30 wt%) H2O2: 5 mmol added to the two mixed solutions. | 98.1 | 87.8 | 89.6 | [94] |
Fe2O3/g-C3N4 Pd/g-C3N4 Cu/g-C3N4 Ni/g-C3N4 Ag/g-C3N4 FePd/g-C3N4 FeCu/g-C3N4 FeAg/g-C3N4 FeNi/g-C3N4 PdCu/g-C3N4 PdNi/g-C3N4 PdAg/g-C3N4 CuNi/g-C3N4 CuAg/g-C3N4 CuAg/g-C3N4a CuAg/g-C3N4b CuAg/g-C3N4c CuAg/g-C3N4d CuAg/g-C3N4e CuAg/g-C3N4f | 12 12 12 12 12 12 12 12 12 12 12 12 12 0.5 0.5 0.5 3 0.5 0.5 0.5 | Visible light 20 W domestic bulb | Photocatalyst: 100 mg Benzene:1 mmol CH3CN: 5.0 mL (30 wt%) H2O2: 1.1 mmol a50 mg of catalyst b 25 mg of catalyst c 15 mg of catalyst d methanol as a solvent e water as a solvent f ethanol as a solvent | 15 43 39 20 32 70 67 41 29 81 72 77 57 99 99 a 99 b 99 c 86 d 83 e 99 f | − | − | [95] |
mpg-C3N4 3%FeCl3/mpg-C3N4 5%FeCl3/mpg-C3N4 10%FeCl3/mpg-C3N4 20%FeCl3/mpg-C3N4 5%FeCl3/mpg-C3N4a 5%FeCl3/mpg-C3N4b 5%FeCl3/mpg-C3N4c 5%FeCl3/mpg-C3N4d 5%FeCl3/mpg-C3N4e | 4 | 100 W mercury lamp λ > 420nm | Photocatalyst: 25 mg benzene: 4.5 mmol (30 wt%) H2O2: 0.255 mL 60 °C a T = 25 °C b T = 40 °C c T = 80 °C d H2O2: 0.510 mL e H2O2: 0.765 mL | 2 17 38 23 25 4 a 10 b 21 c 44 d 47 e | − | 95 98 97 94 80 99 a 96 b 81 c 85 d 60 e | [75] |
g-C3N4 mpg-C3N4 FeCl3 5%Fe-g-C3N4 10%Fe-g-C3N4 20%Fe-g-C3N4Cu-g-C3N4 Ti-g-C3N4 Ni-g-C3N4 Zn-g-C3N4 Fe/SBA-15 g-C3N4/SBA-15 Fe-g-C3N4/SBA-15 | 4 | 500 W Xenon lamp λ > 420 nm | Photocatalyst: 50 mg CH3CN: 4 mL benzene: 0.8 mL H2O: 4 mL (30 wt%)H2O2: 0.51 mL | − | 0 2.0 0.5 1.8 4.8 2.5 1.4 0.1 0.1 0.1 1.0 0.1 11.9 | − | [73] |
10%Fe-g-C3N4 20%Fe-g-C3N4 30%Fe-g-C3N4 10%Fe-g-C3N4-LUS-1 20%Fe-g-C3N4-LUS-1 | 4 | sunlight | Photocatalyst: 0.05 g benzene: 1 mL CH3CN: 4 mL H2O2: 0.5 mL T = 60 °C | − | 6.5 8 10.5 10 16 | >90 ~90 ~ 90 >90 >90 | [96] |
Fe-CN TS-1 Fe-CN/TS-1–1 a Fe-CN/TS-1–2 b Fe-CN/TS-1–3 c Fe-CN/TS-1–4 d Fe-CN/TS-1–5 e Fe-CN/TS-1–6 f Fe-CN/TS-1–2 g Fe-CN/TS-1–7 h Fe-CN/TS-1–8 i Fe/TS-1 | 4 | 300 W Xenon lamp λ> 420 nm | CH3CN: 4 mL benzene: 0.8 mL H2O: 4 mL (30 wt%) H2O2: 0.51 mL 60 °C pH = 7 Fe-CN/TS-1-X a X = 1 for 10% dicyandiamide/TS-1 b X = 2 for 20% dicyandiamide/TS-1 c X = 3 for 50% dicyandiamide/TS-1 d X = 4 for 100% dicyandiamide/TS-1 e X = 5 for 200% dicyandiamide/TS-1 Fe-CN/TS-1-X f X = 6 for 5% FeCl3/dicyandiamide g X = 2 for 10% FeCl3/dicyandiamide h X = 7 for 20% FeCl3/dicyandiamide i X = 8 for 50% FeCl3/dicyandiamide | − | 1.1 2.4 2.8 a 10 b 8.8 c 1.3 d 0.1 e 1.4 f 10 g 5 h 1.6 i 7.6 | − | [97] |
MIL-100(Fe) MIL-68(Fe)i | 8 | Visible light irradiation λ≥ 420 nm | Photocatalyst: 10 mg H2O2: 0.5 mmol Solvent: 4 mL a CH3CN solvent H2O2:benzene(1:2) b Acetone solvent H2O2:benzene(1:2) c H2O solvent H2O2:benzene(1:2) d DMF solvent H2O2:benzene(1:2) e CH3CN:H2O (1:1) H2O2:benzene(1:2) f CH3CN:H2O (1:1) H2O2:benzene(3:4) g CH3CN:H2O (1:1) H2O2:benzene(2:2) h CH3CN:H2O (1:1) H2O2:benzene(3:2) i CH3CN:H2O (1:1) H2O2:benzene(3:4) | 10.3 a 2.4 b 8.3 c 3.3 d 13.6 e 20.1 f 21.7 g 22.5 h 14i | 10.3 a 2.38 b 7.1 c 2.5 d 13.3 e 14.77 f 20.8 g 31.05 h 9.45 i | >99 a 99 b 85 c 76 d 98 e 98 f 96 g 92 h 90 i | [98] |
Ti/CNT Cu/Ti/CNT | 0.75 | Low-pressure mercury lamp | Photocatalyst: 100 mg benzene: 20 mL H2O: 20 mL | 53.8 68.3 | 35.1 51.8 | 65.3 75.8 | [99] |
Zn-Ti-LDH | 3 | 300 W Xenon lamp | Photocatalyst: 20 mg Benzene: 0.2 mmol H2O: 20 mL | 5.65 | 4.59 | 87.18 | [100] |
Bi2WO6/CdWO4 composite | 3 | 300 W Xe lamp λ ≥4 00nm | Photocatalyst: 50 mg benzene: 0.5 mmol CH3CN: 3 mL H2O: 100 μL O2: 3 mL min−1 | 5.8 | − | >99 | [72] |
QuCN+ ion | 1 | 500 W xenon lamp λ = 290–600 nm | [QuCN+]: 2.0 mM [C6H6]: 30 mM [H2O]: 3.0 M | 31 | 30 | 98 | [76] |
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Mancuso, A.; Sacco, O.; Sannino, D.; Venditto, V.; Vaiano, V. One-Step Catalytic or Photocatalytic Oxidation of Benzene to Phenol: Possible Alternative Routes for Phenol Synthesis? Catalysts 2020, 10, 1424. https://doi.org/10.3390/catal10121424
Mancuso A, Sacco O, Sannino D, Venditto V, Vaiano V. One-Step Catalytic or Photocatalytic Oxidation of Benzene to Phenol: Possible Alternative Routes for Phenol Synthesis? Catalysts. 2020; 10(12):1424. https://doi.org/10.3390/catal10121424
Chicago/Turabian StyleMancuso, Antonietta, Olga Sacco, Diana Sannino, Vincenzo Venditto, and Vincenzo Vaiano. 2020. "One-Step Catalytic or Photocatalytic Oxidation of Benzene to Phenol: Possible Alternative Routes for Phenol Synthesis?" Catalysts 10, no. 12: 1424. https://doi.org/10.3390/catal10121424