Real-Time Raman monitoring and control of the catalytic acetalization of glycerol with acetone over modified mesoporous cellular foams

Journal of Physical Chemistry C

Volumn 118, Issue 20, 2014, Pages 10780-10791

  Calvino Casilda, V ^a   Stawicka, K ^a,b   Trejda, M ^b   Ziolek, M ^b   Banares M A ^a  

^a INSTITUTO DE CATÁLISIS Y PETROLEOQUÍMICA   (Spain)

^b ADAM MICKIEWICZ UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; CATALYSTS; GLYCEROL; MESOPOROUS MATERIALS; RAMAN SPECTROSCOPY; REAL TIME CONTROL;

ACETALIZATION REACTION; CHEMOMETRIC ANALYSIS; HETEROGENEOUS CATALYST; IN-SITU RAMAN SPECTROSCOPY; OPTIMAL REACTION CONDITION; REACTION CONDITIONS; REACTION PARAMETERS; REACTION TEMPERATURE;

REACTION INTERMEDIATES;

EID: 84901374750     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp500651e     Document Type: Article

References (38)

1. Leoneti, A. B.; Aragão-Leoneti, V.; de Oliveira, S. V. W. B. Glycerol as a By-product of Biodiesel Production in Brazil: Alternatives for the Use of Unrefined Glycerol Renewable Energy 2012, 45, 138-145
2. Pagliaro, M.; Ciriminna, R.; Kimura, H.; Rossi, M.; Della Pina, C. From Glycerol to Value-Added Products Angew. Chem., Int. Ed. 2007, 46 (24) 4434-4440 (Pubitemid 46954591)
3. Pagliaro, M.; Rossi, M. The Future of Glycerol: New Usages for a Versatile Raw Material; Royal Society of Chemistry: Cambridge, U.K., 2008.
4. Crotti, C.; Farnetti, E.; Guidolin, N. Alternative Intermediates for Glycerol Valorization: Iridium-Catalyzed Formation of Acetals and Ketals Green Chem. 2010, 12, 2225-2231
5. Nair, G. S.; Adrijanto, E.; Alsalme, A.; Kozhevnikov, I. V.; Cooke, D. J.; Brown, D. R.; Shiju, N. R. Glycerol Utilization: Solvent-Free Acetalisation over Niobia Catalysts Catal. Sci. Technol. 2012, 2, 1173-1179
6. Ferreira, P.; Fonseca, I. M.; Ramos, A. M.; Vital, J.; Castanheiro, J. E. Valorisation of Glycerol by Condensation with Acetone over Silica-Included Heteropolyacids Appl. Catal., B 2010, 98, 94-99
7. Piasecki, A.; Sokolowski, A.; Burczyk, B.; Kotlewska, U. Synthesis and Surface Properties of Chemodegradable Anionic Surfactants: Sodium (2- n -alkyl-1,3-dioxan-5-yl)sulfates J. Am. Oil Chem. Soc. 1997, 74, 33-37 (Pubitemid 127551875)
8. Climent, M. J.; Corma, A.; Velty, A. Synthesis of Hyacinth, Vanilla, and Blossom Orange Fragrances: The Benefit of Using Zeolites and Delaminated Zeolites as Catalysts Appl. Catal., A 2004, 263, 155-161
9. Garcia, E.; Laca, M.; Pérez, E.; Garrido, A.; Peinado, J. New Class of Acetal Derived from Glycerin as a Biodiesel Fuel Component Energy Fuels 2008, 22, 4274-4280
10. Garcia, H.; Garcia, J. I.; Fraile, J. M.; Mayoral, J. A. Solketal: Green and Catalytic Synthesis and its Classification as a Solvent. 2,2-Dimethyl-4-hidroxymethyl-1,3-dioxolane, an Interesting Green Solvent Produced through Heterogeneous Catalysis Chim. Oggi 2008, 26 (3) 10-12
11. Ray, P. C.; Roberts, S. M. Overcoming Intrinsic Diastereoselection using Polyleucine as a Chiral Epoxidation Catalyst Tetrahedron Lett. 1999, 40, 1779-1782 (Pubitemid 29087298)
12. Monbaliu, J.-C.; Winter, M.; Chevalier, B.; Schmidt, F.; Jiang, Y.; Hoogendoorn, R.; Kousemaker, M. A.; Stevens, C. Feasibility Study for Industrial Production of Fuel Additives from Glycerol Chem. Today (Milano, Italy) 2010, 28, 8-11
13. Deutsch, J.; Martin, A.; Lieske, H. Investigations on Heterogeneously Catalysed Condensations of Glycerol to Cyclic Acetals J. Catal. 2007, 245, 428-435 (Pubitemid 46037693)
14. da Silva, C. X. A.; Goncalves, V. L. C.; Mota, C. J. A. Watertolerant Zeolite Catalyst for the Acetalisation of Glycerol Green Chem. 2009, 1, 38-41
15. Roldán, L.; Mallada, R.; Fraile, J. M.; Mayoral, J. A.; Menéndez, M. Glycerol Upgrading by Ketalization in a Zeolite Membrane Reactor Asia-Pac. J. Chem. Eng. 2009, 4, 279-284
16. Vicente, G.; Melero, J. A.; Morales, G.; Paniagua, M.; Martin, E. Acetalisation of Bio-glycerol with Acetone to Produce Solketal over Sulfonic Mesostructured Silicas Green Chem. 2010, 12, 899-907
17. Stawicka, K.; Trejda, M.; Ziolek, M. The Production of Biofuels Additives on Sulphonated MCF Materials Modified with Nb and Ta-Towards Efficient Solid Catalysts of Esterification Appl. Catal., A 2013, 467, 325-334
18. Trejda, M.; Stawicka, K.; Ziolek, M. The role of Nb in the Formation of Sulphonic Species in SBA-15 and MCF Functionalised with MPTMS Catal. Today 2012, 192, 130-135
19. Stawicka, K.; Trejda, M.; Ziolek, M. New Phospho-silicate and Niobo-phospho-silicate MCF Materials Modified with MPTMS-Structure, Surface and Catalytic Properties Microporous Mesoporous Mater. 2013, 181, 88-98
20. Lettow, J. S.; Han, Y. J.; Schmidt-Winkel, P.; Yang, P.; Zhao, D.; Stucky, G. D.; Ying, J. Y. Hexagonal to Mesocellular Foam Phase Transition in Polymer-Templated Mesoporous Silicas Langmuir 2000, 16, 8291-8295
21. Li, L.; Koranyi, T. I.; Sels, B. F.; Percarmona, P. P. Highly-efficient Conversion of Glycerol to Solketal over Heterogeneous Lewis Acid Catalysts Green Chem. 2012, 14, 1611-1619
22. Calvino-Casilda, V.; Bañares, M. A. Recent Advances in Imaging and Monitoring of Heterogeneous Catalysts with Raman Spectroscopy Catalysis 2012, 24, 1-47 Specialist Periodical Report, Royal Society of Chemistry (RSC)
23. Bennici, S. M.; Vogelaar, B. M.; Nijhuis, T. A.; Weckhuysen, B. M. Real-Time Control of a Catalytic Solid in a Fixed-Bed Reactor Based on In Situ Spectroscopy Angew. Chem., Int. Ed. 2007, 46, 5412-5416 (Pubitemid 47067646)
24. Stavitski, E.; Weckhuysen, B. M. Infrared and Raman Imaging of Heterogeneous Catalysts Chem. Soc. Rev. 2010, 39, 4615-4625
25. Pivonka, D. E.; Sparks, R. B. Implementation of Raman Spectroscopy as an Analytical Tool throughout the Synthesis of Solid-Phase Scaffolds Appl. Spectrosc. 2000, 54, 1584-1590 (Pubitemid 32074743)
26. Schmink, J. R.; Holcomb, J. L.; Leadbeater, N. E. Use of Raman Spectroscopy as an In Situ Tool to Obtain Kinetic Data for Organic Transformations Chem.-Eur. J. 2008, 32 (14) 9943-9950
27. Calvino-Casilda, V.; Pérez-Mayoral, E.; Bañares, M. A.; Lozano Diz, E. Real-Time Raman Monitoring of Dry Media Heterogeneous Alkylation of Imidazole with Acidic and Basic Catalysts Chem. Eng. J. (Amsterday, Neth.) 2010, 161, 371-376
28. Mikolajska, E.; Calvino-Casilda, V.; Bañares, M. A. Real-Time Raman Monitoring of Liquid-Phase Cyclohexene Epoxidation over Alumina-Supported Vanadium and Phosphorous Catalysts Appl. Catal., A 2012, 421- 422, 164-171
29. Calvino-Casilda, V.; Bañares, M. A. In situ Raman Monitoring of Michael Addition for the Synthesis of 1-Substituted Imidazoles Intermediates with Antiviral Properties Catal. Today 2012, 187, 191-194
30. Schmidt-Winkel, P.; Lukens, W. W.; Yang, P., Jr.; Margolese, D. I.; Lettow, J. S.; Ying, J. Y.; Stucky, G. D. Microemulsion Templating of Siliceous Mesostructured Cellular Foams with Well-Defined Ultralarge Mesopores Chem. Mater. 2000, 12, 686-696
31. Lukens, W. W.; Schmidt-Winkel, P., Jr.; Zhao, D.; Feng, J.; Stucky, G. D. Evaluating Pore Sizes in Mesoporous Materials: A Simplified Standard Adsorption Method and a Simplified Broekhoff de Boer Method Langmuir 1999, 15, 5403-5409
32. Zhao, D.; Feng, J.; Huo, Q.; Melosh, N.; Fredrickson, G. H.; Chmelka, B. F.; Stucky, G. D. Triblock Copolymer Syntheses of Mesoporous Silica with Periodic 50 to 300 Angstrom Pores Science 1998, 279, 548-522
33. 2 Solid Acid Catalysts Heterocycles 2012, 85, 2977-2986
34. 2 Solid Acids for Heterogeneous Catalysis: Acetalization of Bio-glycerol Green Chem. 2013, 15, 478-489
35. Ozorio, L. P.; Pianzolli, R.; Mota, M. B. S.; Mota, C. J. A. Reactivity of Glycerol/Acetone Ketal (Solketal) and Glycerol/Formaldehyde Acetals toward Acid-Catalyzed Hydrolysis J. Braz. Chem. Soc. 2012, 23, 931-937
36. Chandrasekhar, S. Product Stability in Kinetically-Controlled Organic Reactions Chem. Soc. Rev. 1987, 16, 313-338
37. da Silva, C. X. A.; Goncalves, V. L. C.; Mota, C. J. A. Water-Tolerant Zeolite Catalyst for the Acetalisation of Glycerol Green Chem. 2009, 11, 38-41
38. Kojima, S. Anomalous Behaviour of the O-H Stretching Vibrational Mode in the Liquid-Glass Transition of Glycerol J. Mol. Struct. 1993, 294, 193-195