Immobilization of Rh(I)-N-Xantphos and Fe(II)-C-Scorpionate onto Magnetic Nanoparticles: Reusable Catalytic System for Sequential Hydroformylation/Acetalization
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization of Catalysts
2.2. Homogeneous Hydroformylation/Acetalization of Olefins
2.3. Sequential Heterogeneous Hydroformylation/Acetalization of Olefins
2.4. Reutilization of Heterogeneous Catalysts
3. Experimental
3.1. Chemicals and Materials
3.2. Instrumentation
3.3. Synthesis of New Catalysts
3.3.1. CAT1 Synthesis
3.3.2. Magnetic Nanoparticles Synthesis and Functionalization
3.3.3. CAT5 Synthesis
3.3.4. CAT6 Synthesis
3.4. General Methods for the Hydroformylation/Acetalization of Alkenes
3.4.1. Homogeneous Bimetallic System
3.4.2. Heterogeneous One-Pot Bimetallic System
3.4.3. Heterogeneous Sequential Process
3.4.4. Reutilization Process
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Entry. | Catalytic System | Conversion (%) [b] | Selectivity (%) [b] (l:b) | ||
---|---|---|---|---|---|
6 | 7 | 8 | |||
1 | [Rh(acac)(CO)2] | 93 | 60 | 21 (38:62) | 19 (23:77) |
2 | [Rh(acac)(CO)2] HC(pz)3 (1) | 95 | 46 | 34 (44:56) | 20 (18:82) |
3 | [Rh(acac)(CO)2] CAT1 | 99 | 36 | 47 (61:39) | 17 (27:73) |
4 | CAT2 CAT1 | 99 | 3 | 82 (93:7) | 15 (80:20) |
5 | CAT3 CAT1 | 97 | 1 | 87 (66:34) | 12 (24:76) |
6 | CAT4 CAT1 | 99 | - | 91 (69:31) | 9 (32:68) |
7 | CAT1 | 1 | - | - | - |
8 [c] | CAT1 | 95 | - | 100 | - |
Entry. | Olefin | Reaction Yield (%) [a] | |
---|---|---|---|
Major Product (Isolated Yield) | Minor Products | ||
1 [b] | Oct-1-ene isomers: 4 Aldehydes: 11 Branched acetal: 6 | ||
2 [c] | Aldehydes: 20 | ||
3 [c] | Difunctionalized acetal (isomers): 33 |
Entry | Substrate | Catalyst | Conversion (%) [b] | Selectivity (%) [b] (l:b) | ||
---|---|---|---|---|---|---|
6 | 7 | 8 | ||||
1 [c] | Oct-1-ene | CAT5 | 99 | 3 | - | 96(98:2) |
2 [d] | Nonanal | CAT6 | 90 | - | 90(100:0) | 10 |
3 [c],[d] | Oct-1-ene | CAT5 CAT6 | 92 | 54 | - | 38(75:25) |
4 [e] | Nonanal | CAT6 | 90 | 2 | 87(99:1) | 10(98:2) |
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Rodrigues, F.M.S.; Dias, L.D.; Calvete, M.J.F.; Maria, T.M.R.; Rossi, L.M.; Pombeiro, A.J.L.; Martins, L.M.D.R.S.; Pereira, M.M. Immobilization of Rh(I)-N-Xantphos and Fe(II)-C-Scorpionate onto Magnetic Nanoparticles: Reusable Catalytic System for Sequential Hydroformylation/Acetalization. Catalysts 2021, 11, 608. https://doi.org/10.3390/catal11050608
Rodrigues FMS, Dias LD, Calvete MJF, Maria TMR, Rossi LM, Pombeiro AJL, Martins LMDRS, Pereira MM. Immobilization of Rh(I)-N-Xantphos and Fe(II)-C-Scorpionate onto Magnetic Nanoparticles: Reusable Catalytic System for Sequential Hydroformylation/Acetalization. Catalysts. 2021; 11(5):608. https://doi.org/10.3390/catal11050608
Chicago/Turabian StyleRodrigues, Fábio M. S., Lucas D. Dias, Mário J. F. Calvete, Teresa M. R. Maria, Liane M. Rossi, Armando J. L. Pombeiro, Luísa M. D. R. S. Martins, and Mariette M. Pereira. 2021. "Immobilization of Rh(I)-N-Xantphos and Fe(II)-C-Scorpionate onto Magnetic Nanoparticles: Reusable Catalytic System for Sequential Hydroformylation/Acetalization" Catalysts 11, no. 5: 608. https://doi.org/10.3390/catal11050608