Selective Catalytic Epoxidation–Hydration of α-Pinene with Hydrogen Peroxide to Sobrerol by Durable Ammonium Phosphotungstate Immobilized on Imidazolized Activated Carbon
Abstract
:1. Introduction
2. Experimental Procedure
2.1. Materials and Reagents
2.2. Catalyst Preparation
2.3. Catalytic Materials Characterization
2.4. Catalytic Performance Test
3. Results and Discussion
3.1. Characterization
3.2. Construction of Catalytic Sites for Tandem Epoxidation–Hydration
3.3. Solvent Modification of Catalytic Performance
3.4. Effect of Reaction Conditions on the Process
3.5. Catalytic Stability
3.6. Catalytic Mechanism
3.7. Comparison of Catalytic Performance with the Literature
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Cat. | Conv. /% | Sel. a/% | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | Others b | ||
None | 5.4 | - | <0.1 | 4.2 | 37.1 | 37.3 | 5.8 | 2.2 | 1.6 | 0.4 | 11.4 |
AC | 8.4 | - | <0.1 | 4.2 | 32.6 | 38.3 | 6.8 | 2.8 | 1.8 | 0.4 | 13.0 |
AC-O | 17.9 | - | 0.2 | 4.2 | 8.1 | 7.3 | 2.8 | 3.2 | 2.6 | 0.8 | 71.8 |
AC-COIMI | 2.4 | - | 2.1 | 0.2 | 47.1 | 46.9 | 1.8 | 0.5 | - | - | 1.4 |
AC-COIMI-HPW | 89.3 | 4.3 | 0.1 | 3.2 | 10.1 | 7.7 | 2.2 | 10.5. | 4.3 | 2.1 | 55.8 |
AC-COIMI-NH4PW | 90.6 | 2.6 | 0.8 | 7.5 | 8.6 | 8.3 | 5.6 | 40.5 | 6.6 | 3.4 | 16.0 |
Solvents a | Conv. /% | Sel./% | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | Others | ||
None | 5.4 | - | <0.1 | 4.2 | 37.1 | 37.3 | 5.8 | 2.2 | 1.6 | 0.4 | 11.4 |
DCM (1.60) | 8.7 | - | <0.1 | 4.7 | 40.6 | 21.2 | <0.1 | 2.6 | 7.7 | 0.4 | 22.8 |
HAC (1.74) | 31.5 | - | <0.1 | 11.8 | 3.2 | 17.1 | 1.7 | 19.1 | 8.9 | 2.3 | 35.9 |
EA (1.78) | 22.1 | - | <0.1 | 10.7 | 24.6 | 22.1 | 4.3 | 18.8 | 4.6 | 1.3 | 13.6 |
THF (1.63) | 52.0 | 6.9 | 11.6 | 7.5 | 14.1 | 31.9 | 1.2 | 9.7 | 3.1 | 0.9 | 13.1 |
Dioxane (0) | 45.3 | 4.6 | 12.3 | 8.2 | 15.8 | 27.4 | 2.3 | 8.3 | 2.5 | 2.2 | 16.4 |
Acetone (2.88) | 66.2 | 3.3 | <0.1 | 16.0 | 4.8 | 8.8 | 3.1 | 28.8 | 6.7 | 3.8 | 24.8 |
Butanone (2.78) | 46.1 | 9.6 | 10.0 | 6.7 | 11.8 | 2.1 | 2.0 | 24.5 | 11. | 5.1 | 12.9 |
CAN (3.92) | 90.6 | 2.6 | 0.8 | 7.5 | 8.6 | 8.3 | 5.6 | 40.5 | 6.6 | 3.4 | 16.0 |
Substrate/Catalyst | T/°C | t/h | Conv.% | Sel./% | Times a | Ref. |
---|---|---|---|---|---|---|
α-Pinene/AC-COIMI-NH4PW | 40 | 3 | 90.6 | 40.5 | 6 | This work |
α-Epoxypinane/Ce/SiO2 | 25 | 3 | 98 | 72 | 1 | [20] |
α-Epoxypinane/HPW | 60 | 3 | 100 | 38 | 1 | [22] |
α-Epoxypinane/CsPW | 25 | 5 | 100 | 48 | 1 | [23] |
α-Pinene/V2O5 | 25 | 2 | 85.7 | 38.0 | 1 | [25] |
α-Epoxypinane/MIL-100 | 30 | 0.5 | 98 | 7 | 1 | [30] |
α-Epoxypinane/acidic clays | 50 | 2 | 99.9 | 8.3 | 1 | [31] |
α-Epoxypinane/Fe2+-MCM | 40 | 3 | 96 | 56 | 1 | [32] |
α-Epoxypinane/12%Al-SiO2 | 30 | 0.5 | 80 | 8 | 1 | [33] |
α-Pinene/V-M(x) | 70 | 7 | 84.5 | 36.3 | 4 | [34] |
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Zheng, M.; Li, X.; Xun, Y.; Wang, J.; Yin, D. Selective Catalytic Epoxidation–Hydration of α-Pinene with Hydrogen Peroxide to Sobrerol by Durable Ammonium Phosphotungstate Immobilized on Imidazolized Activated Carbon. Nanomaterials 2023, 13, 1554. https://doi.org/10.3390/nano13091554
Zheng M, Li X, Xun Y, Wang J, Yin D. Selective Catalytic Epoxidation–Hydration of α-Pinene with Hydrogen Peroxide to Sobrerol by Durable Ammonium Phosphotungstate Immobilized on Imidazolized Activated Carbon. Nanomaterials. 2023; 13(9):1554. https://doi.org/10.3390/nano13091554
Chicago/Turabian StyleZheng, Min, Xiangzhou Li, Youyi Xun, Jianhua Wang, and Dulin Yin. 2023. "Selective Catalytic Epoxidation–Hydration of α-Pinene with Hydrogen Peroxide to Sobrerol by Durable Ammonium Phosphotungstate Immobilized on Imidazolized Activated Carbon" Nanomaterials 13, no. 9: 1554. https://doi.org/10.3390/nano13091554