An Investigation of N-Hydroxyphthalimide Catalyzed Aerobic Oxidation of Toluene without Metal Ions in Liquid Phase: Effect of Solvents and Phase Transfer Catalysts
Abstract
:1. Introduction
2. Results and Discussion
2.1. Effect of Solvents on Metal-Free Oxofunctionalization of Toluene
2.2. Role of Phase Transfer Catalysts on Metal-Free Oxofunctionalization of Toluene under Solvent-Free Conditions
3. Experimental Section
3.1. Aerobic Oxidation of Toluene in Different Solvents
3.2. Solvent-Free Aerobic Oxidation of Toluene Mediated by Different Phase Transfer Catalysts
3.3. Identification of Products and Intermediates by GC-MS
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Starting Material | Conversion (%) | Selectivity (%) | ||||
---|---|---|---|---|---|---|
BAH | BAL | BAC | DBE | Others | ||
BAH | 63.3 | - | 1.7 | 94.6 | 3.5 | 0.2 |
BAL | 6.0 | 100 | - | 0.0 | 0.0 | 0.0 |
BAC | 0.0 | - | - | - | - | - |
DBE | 33.2 | 71.8 | 23.6 | 4.0 | - | 0.6 |
Toluene | 29.8 | 73.3 | 16.9 | 4.6 | 5.0 | 0.2 |
Entry | Phase Transfer Catalyst | Toluene Conversion (%) | Selectivity (%) | ||||
---|---|---|---|---|---|---|---|
BAH | BAL | BAC | DBE | Others | |||
1 | - | 2.2 | 79.7 | 20.3 | 0.0 | 0.0 | 0.0 |
2 | OP-10 | 2.3 | 80.1 | 19.9 | 0.0 | 0.0 | 0.0 |
3 | SDBS | 2.4 | 79.3 | 19.9 | 0.0 | 0.0 | 0.8 |
4 | BS-12 | 11.2 | 26.9 | 6.1 | 59.6 | 5.1 | 2.4 |
5 | DDAB | 29.4 | 9.4 | 3.9 | 80.9 | 2.1 | 3.6 |
Starting Material | Conversion (%) | Selectivity (%) | |||||
---|---|---|---|---|---|---|---|
BAH | BAL | BAC | DBE | BBE | Others | ||
Toluene | 29.4 | 9.4 | 3.9 | 80.9 | 2.1 | 0.0 | 3.6 |
BAL | 100 | 11.3 | - | 71.4 | 0.9 | 7.4 | 9.0 |
DBE | 96.9 | 6.5 | 3.0 | 28.2 | - | 28.8 | 33.5 |
Catalyst | Conversion (%) | Selectivity (%) | ||||
---|---|---|---|---|---|---|
BAH | BAL | BAC | DBE | Others | ||
None | 0.3 | 86.8 | 13.2 | 0.0 | 0.0 | 0.0 |
NHPI | 2.2 | 79.7 | 20.3 | 0.0 | 0.0 | 0.0 |
DDAB | 0.2 | 100 | 0.0 | 0.0 | 0.0 | 0.0 |
NHPI, DDAB | 29.4 | 9.4 | 3.9 | 80.9 | 2.1 | 3.6 |
NHPI, DDAB, TEMPO b | 0.0 | - | - | - | - | - |
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Shi, G.; Dong, L.; Feng, Y. An Investigation of N-Hydroxyphthalimide Catalyzed Aerobic Oxidation of Toluene without Metal Ions in Liquid Phase: Effect of Solvents and Phase Transfer Catalysts. Molecules 2024, 29, 3066. https://doi.org/10.3390/molecules29133066
Shi G, Dong L, Feng Y. An Investigation of N-Hydroxyphthalimide Catalyzed Aerobic Oxidation of Toluene without Metal Ions in Liquid Phase: Effect of Solvents and Phase Transfer Catalysts. Molecules. 2024; 29(13):3066. https://doi.org/10.3390/molecules29133066
Chicago/Turabian StyleShi, Guojun, Longsheng Dong, and Ya Feng. 2024. "An Investigation of N-Hydroxyphthalimide Catalyzed Aerobic Oxidation of Toluene without Metal Ions in Liquid Phase: Effect of Solvents and Phase Transfer Catalysts" Molecules 29, no. 13: 3066. https://doi.org/10.3390/molecules29133066