Solvent-Free Microwave-Induced Oxidation of Alcohols Catalyzed by Ferrite Magnetic Nanoparticles
Abstract
:1. Introduction
2. Results and Discussion
2.1. Catalysts Characterization
2.1.1. FT-IR Spectra (Infrared Spectroscopy)
2.1.2. XRD (X-ray Diffraction Pattern)
2.1.3. TEM (Transmission Electron Microscopy)
2.1.4. SEM–EDS (Scanning Electron Microscopy-Energy Dispersive X-ray Spectroscopy)
2.1.5. VSM (Vibrating Sample Magnetometry)
2.2. Catalytic Performance
3. Experimental Section
3.1. Materials and Instrumentation
3.2. Catalyst Preparation
3.3. General Procedure for the Peroxidative Oxidation of Alcohols
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Entry | Catalyst | M (mg) | Cat/Alcohol Molar Ratio | Yield b (%) |
---|---|---|---|---|
1 | none | - | - | 1.8 |
2 | FeCl2·6H2O | 19.9 | 0.04 | 12.9 |
3 | FeCl3 | 16.2 | 0.04 | 22.7 |
4 | FeCl2·6H2O + 2FeCl3 | 5.3 + 13.3 | 0.01 + 0.03 | 15.2 |
5 | Fe3O4 (2) | 2.9 | 0.005 | 3.1 |
6 | Fe3O4 (2) | 29.6 | 0.05 | 17.8 |
7 c | Fe3O4 (2) | 29.7 | 0.05 | 12.2 |
Entry | Oxidant | Additive | Yield b (%) |
---|---|---|---|
§ | - | - | no reaction |
2 | O2 (1 atm) | - | 1.3 |
3 | H2O2 30% | - | 11.1 |
4 | t-BuOOH 70% | - | 17.8 |
5 c | t-BuOOH 70% | TEMPO 2.5% mol vs. subs | 7.3 |
6 d | t-BuOOH 70% | Ph2NH 100% mol vs. subs | 0.2 |
7 d | t-BuOOH 70% | CBrCl3 100% mol vs. subs | 0.7 |
Entry | Temperature (°C) | Yield b (%) |
---|---|---|
1 | 50 | 9.2 |
2 | 80 | 17.8 |
3 | 100 | 18.3 |
4 | 120 | 21.2 |
5 | 150 | 18.6 |
Entry | Substrate | Product | Yield b (%) |
---|---|---|---|
1 | 1-Phenylethanol | Acetophenone | 58.3 |
2 | Benzyl alcohol | Benzaldehyde | 51.2 |
3 | Benzhydrol | Benzophenone | 53.5 |
4 | Cinnamyl alcohol | Cinnamaldehyde | 38.3 |
5 | Cyclopentanol | Cyclopentanone | 39.2 |
6 | Cyclohexanol | Cyclohexanone | 41.1 |
7 | Cycloheptanol | Cycloheptanone | 45.1 |
8 | Cyclooctanol | Cyclooctanone | 46.8 |
Catalyst | Acetophenone Yield b (%) | Benzaldehyde Yield b (%) |
---|---|---|
MnFe2O4 (1) | 80.8 | 79.1 |
Fe3O4 (2) | 58.3 | 51.2 |
CoFe2O4 (3) | 93.7 | 88.9 |
NiFe2O4 (4) | 52.4 | 46.2 |
CuFe2O4 (5) | 93.5 | 86.7 |
ZnFe2O4 (6) | 48.0 | 44.7 |
Entry | Catalyst | Reaction Conditions | Conversion a (%) | Selectivity b (%) | Reference |
---|---|---|---|---|---|
1 | Au/Mg-350 | Methanol, 10 atm (O2), 110 °C, 10 h | 96 | 33 | [51] |
2 | Au/Mg-500 | Methanol, 10 atm (O2), 110 °C, 10 h | 78 | 66 | [51] |
3 | VPO | MeCN, t-BuOOH, 90 °C (reflux), 8 h | 50 | 100 | [49] |
4 | VPO-Co-n (0.01) | MeCN, t-BuOOH, 90 °C (reflux), 8 h | 70 | 84 | [49] |
5 | VPO-Co-n (0.03) | MeCN, t-BuOOH, 90 °C (reflux), 8 h | 67 | 67 | [49] |
6 | VPO-Co-n (0.06) | MeCN, t-BuOOH, 90 °C (reflux), 8 h | 56 | 100 | [49] |
7 | VPO-Co-n (0.1) | MeCN, t-BuOOH, 90 °C (reflux), 8 h | 65 | 77 | [49] |
8 | VPO-Co-a (0.2) | MeCN, t-BuOOH, 90 °C (reflux), 8 h | 66 | 74 | [49] |
9 | VPO-Co-a (0.5) | MeCN, t-BuOOH, 90 °C (reflux), 8 h | 57 | 93 | [49] |
10 | VPO-Co-a (1) | MeCN, t-BuOOH, 90 °C (reflux), 8 h | 66 | 82 | [49] |
11 | SIL-FeCl3 (loading FeCl3 = 0.71) | Solvent-free, H2O2, 90 °C, 5 h | 62.2 | 70.7 | [52] |
12 | Au@1Pd/SiO2 | Solvent-free, O2, 90 °C, 6 h | 8.8 | 91 | [53] |
13 | Au@5Pd/SiO2 | Solvent-free, O2, 90 °C, 6 h | 54 | 93 | [53] |
14 | Au@8Pd/SiO2 | Solvent-free, O2, 90 °C, 6 h | 91 | 87 | [53] |
15 | Au@10Pd/SiO2 | Solvent-free, O2, 90 °C, 6 h | 88 | 91 | [53] |
16 | Au@15Pd/SiO2 | Solvent-free, O2, 90 °C, 6 h | 90 | 88 | [53] |
17 | Au@20Pd/SiO2 | Solvent-free, O2, 90 °C, 6 h | 94 | 88 | [53] |
18 | CuAl2O4 | MeCN, H2O2, 80 °C, 8 h | 99 | 98 | [54] |
19 | AgNPs/rGO | MeCN, NHPI, O2, 80 °C, 24 h | 12 | 8 | [55] |
20 | Ag NPs/GO | MeCN, NHPI, O2, 80 °C, 24 h | 33 | 55 | [55] |
21 | Ag NPs/GOSH | MeCN, NHPI, O2, 80 °C, 24 h | 61 | 58 | [55] |
22 | CoAl2O4 | MeCN, O2, 80 °C, 5 h | 80.9 | 96.7 | [56] |
23 | CdS-MTA | MeCN, O2, 5 °C, UV–vis, 1 h | 65 | >99 | [57] |
24 | Au/HT-3 | O2, in visible light, 24 h | 57.4 | 93.8 | [58] |
25 | Au/HT-3 | O2, in the dark, 24 h | 3.7 | 91.5 | [58] |
26 | Co2Al-LDH | MeCN, t-BuOOH, 60 °C, 30 min | 26.9 | 91.1 | [50] |
27 | Co2Mg0.5Al-LDH | MeCN, t-BuOOH, 60 °C, 30 min | 38.1 | 88.9 | [50] |
28 | Co2MgAl-LDH | MeCN, t-BuOOH, 60 °C, 30 min | 39.5 | 89.2 | [50] |
29 | Co2Mg1.5Al-LDH | MeCN, t-BuOOH, 60 °C, 30 min | 33.8 | 92.0 | [50] |
30 | Co2Mg2Al-LDH | MeCN, t-BuOOH, 60 °C, 30 min | 32.1 | 94.9 | [50] |
31 | Pd@PBFS-500 | H2O, O2, 80 °C, 0.1 MPa, 0.5 h | 87 | >99 | [59] |
32 | Pd/CB | H2O, O2, 80 °C, 0.1 MPa, 2 h | 10 | >99 | [60] |
33 | Pd/AC | H2O, O2, 80 °C, 0.15 MPa, 3 h | 18 | 91 | [61] |
34 | Pd/CMK-3 | 1,4-Dioxane, O2, 80 °C, 0.1 MPa, 1 h | 55 | 80 | [62] |
35 | Pd@hmC | H2O, K2CO3, O2, 80 °C, 0.1 MPa, 1 h | 48 | 77 | [63] |
36 | Pd/Fe@C | H2O, K2CO3, O2, 80 °C, 0.1 MPa, 1 h | 63 | 67 | [64] |
37 | Cu-FPZ | MeCN, NaHCO3, TEMPO, O2, 60 °C, 12 h | 99 | 99 | [43] |
38 | Fe3O4 | Toluene, O2, 80 °C, 12 h | 80 | 100 | [29] |
39 | Fe3O4/Cu3(BTC)2 | MeCN, Na2CO3, TEMPO, O2, 75 °C, 6 h | >99 | >99 | [44] |
40 | CoFe2O4 | Solvent-free, H2O2, 110 °C, 5 h | >99 | 100 | [30] |
41 | MnFe2O4 (1) | Solvent-free, t-BuOOH, MW 120 °C, 2 h | 79.1 | >99 | This work |
42 | Fe3O4 (2) | Solvent-free, t-BuOOH, MW 120 °C, 2 h | 51.2 | >99 | This work |
43 | CoFe2O4 (3) | Solvent-free, t-BuOOH, MW 120 °C, 2 h | 88.9 | >99 | This work |
44 | NiFe2O4 (4) | Solvent-free, t-BuOOH, MW 120 °C, 2 h | 46.2 | >99 | This work |
45 | CuFe2O4 (5) | Solvent-free, t-BuOOH, MW 120 °C, 2 h | 86.7 | >99 | This work |
46 | ZnFe2O4 (6) | Solvent-free, t-BuOOH, MW 120 °C, 2 h | 44.7 | >99 | This work |
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Martins, N.M.R.; Martins, L.M.D.R.S.; Amorim, C.O.; Amaral, V.S.; Pombeiro, A.J.L. Solvent-Free Microwave-Induced Oxidation of Alcohols Catalyzed by Ferrite Magnetic Nanoparticles. Catalysts 2017, 7, 222. https://doi.org/10.3390/catal7070222
Martins NMR, Martins LMDRS, Amorim CO, Amaral VS, Pombeiro AJL. Solvent-Free Microwave-Induced Oxidation of Alcohols Catalyzed by Ferrite Magnetic Nanoparticles. Catalysts. 2017; 7(7):222. https://doi.org/10.3390/catal7070222
Chicago/Turabian StyleMartins, Nuno M. R., Luísa M. D. R. S. Martins, Carlos O. Amorim, Vitor S. Amaral, and Armando J. L. Pombeiro. 2017. "Solvent-Free Microwave-Induced Oxidation of Alcohols Catalyzed by Ferrite Magnetic Nanoparticles" Catalysts 7, no. 7: 222. https://doi.org/10.3390/catal7070222