Innovative Application of Polyether Amine as a Recyclable Catalyst in Aerobic Thiophenol Oxidation
Abstract
:1. Introduction
2. Materials and Methods
2.1. General Information
2.2. Calculation of the Yield by Internal Standard Using 1H NMR
2.3. Optimization Studies for the Catalyzed Aerobic Oxidation of Thiophenols
2.4. General Procedure for the Catalyzed Aerobic Oxidation of Thiophenols
2.5. A 50 mmol Scale Reaction and the Recycle of Polyether Amine 1 Catalyst
2.6. Mechanistic Investigation
3. Results and Discussion
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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Structure | Properties | Specifications |
---|---|---|
Molecular weight | About 440 | |
Appearance | Colorless-to-pale-yellow liquid | |
Degree of functionality | ~3 | |
Total amine meq/g | 6.1–6.6 | |
Primary amine % | ≥90 | |
Color, Pt-Co (APAH) | ≤50 | |
Water, wt% | ≤0.25 | |
Density g/mL (lb/gal), 25 °C | 0.978 (8.12) | |
Viscosity cSt, 25 °C | 72 | |
Flash point PMCC, °C (°F) | 218.5 (425.3) | |
pH | 11.6 | |
CAS number | 39423-51-3 |
Entry | Base (Equiv.) | Solvent | Time | Atmosphere | Yield a (%) |
---|---|---|---|---|---|
1 | pyridine/100 mol % | CH3CN | 1 h | Air | 16 |
2 | BTMG/100 mol % | CH3CN | 1 h | Air | 11 |
3 | DBU/100 mol % | CH3CN | 1 h | Air | 11 |
4 | triethanolamine/100 mol % | CH3CN | 1 h | Air | 5 |
5 | Et3N/100 mol % | CH3CN | 1 h | Air | >98 |
6 | polyether amine 1/100 mol % | CH3CN | 1 h | Air | >98 |
7 | polyether amine 1/30 mol % | CH3CN | 1 h | Air | >98 |
8 | polyether amine 1/20 mol % | CH3CN | 1 h | Air | >98 |
9 | polyether amine 1/10 mol % | CH3CN | 1 h | Air | >98 |
10 | polyether amine 1/5 mol % | CH3CN | 1 h | Air | >98 |
11 | polyether amine 1/3 mol % | CH3CN | 1 h | Air | 95 |
12 | polyether amine 1/1 mol % | CH3CN | 1 h | Air | 80 |
13 | polyether amine 1/0.5 mol % | CH3CN | 1 h | Air | 62 |
14 | polyether amine 1/0.5 mol % | CH3CN | 1 h | O2 | >98 |
15 | - | CH3CN | 1 h | Air | 3 |
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Chen, L.; Li, J.; Ni, K.; Qin, X.; Wang, L.; Hou, J.; Wang, C.; Li, X.; Wang, M.; An, J. Innovative Application of Polyether Amine as a Recyclable Catalyst in Aerobic Thiophenol Oxidation. Organics 2024, 5, 59-70. https://doi.org/10.3390/org5020005
Chen L, Li J, Ni K, Qin X, Wang L, Hou J, Wang C, Li X, Wang M, An J. Innovative Application of Polyether Amine as a Recyclable Catalyst in Aerobic Thiophenol Oxidation. Organics. 2024; 5(2):59-70. https://doi.org/10.3390/org5020005
Chicago/Turabian StyleChen, Lingxia, Junyu Li, Ke Ni, Xinshu Qin, Lijun Wang, Jiaman Hou, Chao Wang, Xuan Li, Minlong Wang, and Jie An. 2024. "Innovative Application of Polyether Amine as a Recyclable Catalyst in Aerobic Thiophenol Oxidation" Organics 5, no. 2: 59-70. https://doi.org/10.3390/org5020005