Vapour-Phase Selective O-Methylation of Catechol with Methanol over Metal Phosphate Catalysts
Abstract
:1. Introduction
2. Results
2.1. Basic Physicochemical Properties of Metal Phosphates Samples
2.2. Catalytic Performance
2.3. TPD Characterization
2.4. Catalytic Stability and Catalyst Regeneration
3. Discussion
4. Materials and Methods
4.1. Materials
4.2. Sample Preparation
4.3. Catalyst Characterization
4.4. Catalytic Evaluation
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
References
- Dorothea, G.; Barbara, E. Ullmann´s Encyclopaedia of Industrial Chemistry; Verlagsgesellschaft: Weinheim, Germany, 1991; Volume A19. [Google Scholar]
- Vishwanathan, V.; Balakrishna, G.; Rajesh, B.; Jayasri, V.; Sikhwivhilu, L.M.; Coville, N.J. Alkylation of catechol with methanol to give guaiacol over sulphate-modified zirconia solid acid catalysts: The influence of structural modification of zirconia on catalytic performance. Catal. Commun. 2008, 9, 2422–2427. [Google Scholar] [CrossRef]
- Stoochnoff, B.A.; Benoiton, N.L. The methylation of some phenols and alcohols with sodium hydride / methyl iodide in tetrahydrofuran at room temperature. Tetrahedron Lett. 1973, 14, 21–24. [Google Scholar] [CrossRef]
- Luque, R.; Campelo, J.M.; Conesa, T.D.; Luna, D.; Marinas, J.M.; Romero, A.A. Catechol O-methylation with dimethyl carbonate over different acid-base catalysts. New J. Chem. 2006, 30, 1228–1234. [Google Scholar] [CrossRef]
- Jafari, A.A.; Khodadadi, A.; Mortazavi, Y. Vapor-phase selective O-alkylation of catechol with methanol over lanthanum phosphate and its modified catalysts with Ti and Cs. J. Mol. Catal. A 2013, 372, 79–83. [Google Scholar] [CrossRef]
- Vishwanathan, V.; Ndou, S.; Sikhwivhilu, L.; Plint, N.; Raghavan, K.V.; Coville, N.J. Evidence for weak base site participation in the vapour phase methylation of catechol over solid base catalysts. Chem. Commun. 2001, 10, 893–894. [Google Scholar] [CrossRef]
- Fu, Z.H.; Yu, Y.; Yin, D.L.; Xu, Y.Z.; Liu, H.P.; Liao, H.Y.; Xu, Q.; Tan, F.Q.; Wang, J. Vapor-phase highly selective O-methylation of catechol with methanol over ZnCl2 modified gamma-Al2O3 catalysts. J. Mol. Catal. A 2005, 232, 69–75. [Google Scholar] [CrossRef]
- Li, X.M.; Zhang, W.X.; Liu, G.; Jiang, L.; Zhu, X.M.; Pan, C.L.; Jiang, D.Z.; Tang, A.Q. Effect of the P/Al ratio of Al-P-O on the catalytic activity of O-methylation of catechol with methanol. React. Kinet. Catal. Lett. 2003, 79, 365–371. [Google Scholar] [CrossRef]
- Zhu, X.M.; Li, X.M.; Jia, M.J.; Liu, G.; Zhang, W.X.; Jiang, D.Z. Vapour-phase selective O-methylation of catechol with methanol over Ti-containing aluminium phosphate catalysts. Appl. Catal. A 2005, 282, 155–161. [Google Scholar] [CrossRef]
- Zhu, X.M.; Li, X.M.; Zou, X.J.; Wang, Y.L.; Jia, M.J.; Zhang, W.X. Supported ammonium metatungstate as highly efficient catalysts for the vapour-phase O-methylation of catechol with methanol. Catal. Commun. 2006, 7, 579–582. [Google Scholar] [CrossRef]
- Takita, Y.; Qing, X.; Takami, A.; Nishiguchi, H.; Nagaoka, K. Oxidative dehydrogenation of isobutane to isobutene III reaction mechanism over CePO4 catalyst. Appl. Catal. A 2005, 296, 63–69. [Google Scholar] [CrossRef]
- Bautista, F.M.; Campelo, J.M.; Luna, D.; Marinas, J.M.; Quiros, R.A.; Romero, A.A. Screening of amorphous metal-phosphate catalysts for the oxidative dehydrogenation of ethylbenzene to styrene. Appl. Catal. B 2007, 70, 611–620. [Google Scholar] [CrossRef]
- Takita, Y.; Moriyama, J.; Yoshinaga, Y.; Nishiguchi, H.; Ishihara, T.; Yasuda, S.; Ueda, Y.; Kubo, M.; Miyamoto, A. Adsorption of water vapor on the AlPO4-based catalysts and reaction mechanism for CFCs decomposition. Appl. Catal. A 2004, 271, 55–60. [Google Scholar] [CrossRef]
- Takubo, T.; Hirose, Y.; Kashiwagi, D.; Inoue, T.; Yamada, H.; Nagaoka, K.; Takita, Y. Metal phosphate and fluoride catalysts active for hydrolysis of NF3. Catal. Commun. 2009, 11, 147–150. [Google Scholar] [CrossRef]
- Takita, Y.; Tanabe, T.; Ito, M.; Ogura, M.; Muraya, T.; Yasuda, S.; Nishiguchi, H.; Ishihara, T. Decomposition of CH2FCF3 (134a) over metal phosphate catalysts. Ind. Eng. Chem. Res. 2002, 41, 2585–2590. [Google Scholar] [CrossRef]
- Kashiwagi, D.; Takai, A.; Takubo, T.; Nagaoka, K.; Inoue, T.; Takita, Y. Metal phosphate catalysts effective for degradation of sulfur hexafluoride. Ind. Eng. Chem. Res. 2009, 48, 632–640. [Google Scholar] [CrossRef]
- Devi, G.S.; Giridhar, D.; Reddy, B.M. Vapour phase O-alkylation of phenol over alkali promoted rare earth metal phosphates. J. Mol. Catal. A 2002, 181, 173–178. [Google Scholar] [CrossRef]
- Li, F.; Zhang, Y.B.; Xiao, D.H.; Wang, D.Q.; Pan, X.Q.; Yang, X.G. Hydrothermal method prepared Ce-P-O catalyst for the selective catalytic reduction of NO with NH3 in a broad temperature range. ChemCatChem 2010, 2, 1416–1419. [Google Scholar] [CrossRef]
- Zhang, Y.J.; Wang, J.H.; Zhang, T. Novel Ca-doped CePO4 supported ruthenium catalyst with superior catalytic performance for aerobic oxidation of alcohols. Chem. Commun. 2011, 47, 5307–5309. [Google Scholar] [CrossRef]
- Danjo, Y.; Kikuchi, I.; Ino, Y.; Ohshima, M.; Kurokawa, H.; Miura, H. Support effect of Pd/AlPO4 catalyst in hydrogen storage of organic hydride method in the presence of CO. React. Kinet. Mech. Cat. 2012, 105, 381–389. [Google Scholar] [CrossRef]
- Ma, Z.; Yin, H.; Overbury, S.H.; Dai, S. Metal phosphates as a new class of supports for gold nanocatalysts. Catal. Lett. 2008, 126, 20–30. [Google Scholar] [CrossRef]
- Qian, X.S.; Qin, H.M.; Meng, T.; Lin, Y.; Ma, Z. Metal phosphate-supported Pt catalysts for CO oxidation. Materials 2014, 7, 8105–8130. [Google Scholar] [CrossRef] [Green Version]
- Cui, Y.W.; Liu, H.; Lin, Y.; Ma, Z. Metal phosphate-supported RuOx catalysts for N2O decomposition. J. Taiwan Inst. Chem. E. 2016, 67, 254–262. [Google Scholar] [CrossRef]
- Liu, G.; Wang, Z.; Jia, M.; Zou, X.; Zhu, X.; Zhang, W.; Jiang, D. Thermally stable amorphous mesoporous aluminophosphates with controllable P/Al ratio: Synthesis, characterization, and catalytic performance for selective O-methylation of catechol. J. Phys. Chem. B 2006, 110, 16953–16960. [Google Scholar] [CrossRef]
- Liao, X.Z.; Zhou, Z.; Wang, Z.L.; Zou, X.J.; Liu, G.; Jia, M.J.; Zhang, W.X. Preformed precursor of microporous aluminophosphate coating on mesoporous SBA-15: Synthesis, characterization, and catalytic property for selective O-methylation of catechol. J. Colloid Interface Sci. 2007, 308, 176–181. [Google Scholar] [CrossRef]
- Rajesh, K.; Mukundan, P.; Pillai, P.K.; Nair, V.R.; Warrier, K.G.K. High-surface-area nanocrystalline cerium phosphate through aqueous sol-gel route. Chem. Mater. 2004, 16, 2700–2705. [Google Scholar] [CrossRef]
- Rajesh, K.; Shajesh, P.; Seidel, O.; Mukundan, P.; Warrier, K.G.K. A facile sol-gel strategy for the synthesis of rod-shaped, nanocrystalline, high-surface-area lanthanum phosphate powders and nanocoatings. Adv. Funct. Mater. 2007, 17, 1682–1690. [Google Scholar] [CrossRef]
- Qi, C.; Zhu, Y.J.; Wu, C.T.; Sun, T.W.; Chen, F.; Wu, J. Magnesium phosphate pentahydrate nanosheets: Microwave-hydrothermal rapid synthesis using creatine phosphate as an organic phosphorus source and application in protein adsorption. J. Colloid Interface Sci. 2016, 462, 297–306. [Google Scholar] [CrossRef]
- Zhou, X.M.; Du, H.J.; Ma, H.; Sun, L.N.; Cao, R.; Li, H.S.; Zhang, P.X. Facile preparation and characterization of zinc phosphate with self-assembled flower-like micro-nanostructures. J. Phys. Chem. Solids 2015, 78, 1–7. [Google Scholar] [CrossRef]
- Campelo, J.M.; Jaraba, M.; Luna, D.; Luque, R.; Marinas, J.M.; Romero, A.A.; Navio, J.A.; Macias, M. Effect of phosphate precursor and organic additives on the structural and catalytic properties of amorphous mesoporous AlPO4 materials. Chem. Mater. 2003, 15, 3352–3364. [Google Scholar] [CrossRef]
- Srilakshmi, C.; Lingaiah, N.; Nagaraju, P.; Prasad, P.S.S.; Narayana, K.V.; Martin, A.; Luecke, B. Studies on bulk metal phosphate catalysts for the ammoxidation of 2-methylpyrazine. Appl. Catal. A 2006, 309, 247–253. [Google Scholar] [CrossRef]
- Chada, R.R.; Ketike, T.; Boilla, A.R.; Gangadharam, S.D.; Kamaraju, S.R.R.; Burri, D.R. Preparation and characterization of lanthanum phosphate catalysts for O-methylation of phenol to anisole in gas phase. Mol. Catal. 2017, 438, 224–229. [Google Scholar] [CrossRef]
- Lin, Y.; Meng, T.; Ma, Z. Catalytic decomposition of N2O over RhOx supported on metal phosphates. J. Ind. Eng. Chem. 2015, 28, 138–146. [Google Scholar] [CrossRef]
- Lee, H.; Lee, S.; Ryoo, R.; Choi, M. Revisiting side-chain alkylation of toluene to styrene: Critical role of microporous structures in catalysts. J. Catal. 2019, 373, 25–36. [Google Scholar] [CrossRef]
- Nguyen, T.T.N.; Ruaux, V.; Massin, L.; Lorentz, C.; Afanasiev, P.; Mauge, F.; Belliere-Baca, V.; Rey, P.; Millet, J.M.M. Synthesis, characterization and study of lanthanum phosphates as light alcohols dehydration catalysts. Appl. Catal. B 2015, 166, 432–444. [Google Scholar] [CrossRef]
Catalyst | BET Surface Area (m2/g) | Pore Volume (cm3/g) |
---|---|---|
CP | 68 | 0.09 |
LP | 88 | 0.20 |
MP | 64 | 0.35 |
ALP | 29 | 0.11 |
ZP | 7 | 0.02 |
Catalyst | Peak Temperature (°C) | Intensity (a.u.) |
---|---|---|
CP | 215 | 391.24 |
426 | 42.66 | |
LP | 233 | 381.51 |
— | — | |
MP | 199 | 128.91 |
525 | 740.59 | |
ALP | 224 | 351.23 |
426 | 408.90 | |
ZP | 179 | 35.40 |
450 | 734.60 |
Catalyst | Desorption Temperature (°C) | Intensity (a.u.) |
---|---|---|
CP | 150 | 3.71 |
LP | 94 | 4.24 |
MP | 147 | 0.50 |
ALP | 154 | 5.46 |
ZP | - | - |
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Mao, H.; Li, X.; Xu, F.; Xiao, Z.; Zhang, W.; Meng, T. Vapour-Phase Selective O-Methylation of Catechol with Methanol over Metal Phosphate Catalysts. Catalysts 2021, 11, 531. https://doi.org/10.3390/catal11050531
Mao H, Li X, Xu F, Xiao Z, Zhang W, Meng T. Vapour-Phase Selective O-Methylation of Catechol with Methanol over Metal Phosphate Catalysts. Catalysts. 2021; 11(5):531. https://doi.org/10.3390/catal11050531
Chicago/Turabian StyleMao, Haifang, Xiaolei Li, Fen Xu, Zuobing Xiao, Wenxiang Zhang, and Tao Meng. 2021. "Vapour-Phase Selective O-Methylation of Catechol with Methanol over Metal Phosphate Catalysts" Catalysts 11, no. 5: 531. https://doi.org/10.3390/catal11050531