journal article·2017-01Open access

Tuning the acidic–basic properties by Zn-substitution in Mg–Al hydrotalcites as optimal catalysts for the aldol condensation reaction

Willinton Y. Hernández, Funda Aliç, An Verberckmoes, Pascal Van Der Voort

Journal of Materials Science· Volume 52· Issue 1

Abstract

Mg–Zn–Al hydrotalcites and derived mixed oxides with different Mg2+-to-Zn2+ ratios were prepared by co-precipitation in super-saturated conditions, followed by thermal decomposition at 500 °C. The synthesized materials were evaluated as catalysts for the self-condensation of octanal in order to establish structure-to-functionality properties of the prepared materials. The presence of zinc affects the structural and textural properties of the as-synthesized hydrotalcites and derived mixed oxides, and provokes a remarkable modification on the acidic–basic properties of the materials as studied by CO2 and NH3-TPD. The presence of Zn2+ caused an increment in the concentration of surface acidic sites compared to the binary Mg–Al system. The samples characterized by a Zn/Mg ratio ≤1 showed the optimal ratio of acidic and basic sites and the best catalytic performance for the production of the α,β-unsaturated aldehyde. The reconstruction of the layered materials (starting from the mixed oxides) caused an increment in the concentration of surface OH− groups, further modifying the selectivity of the reaction.
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Research context

OpenAlex topics: Layered Double Hydroxides Synthesis and Applications · Magnesium Oxide Properties and Applications · Inorganic Chemistry and Materials

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (44)

Show source-provided references
1. Climent MJ, Corma A, Iborra S, Sabater MJ (2014) Heterogeneous catalysis for tandem reactions. ACS Catal 4(3):870–891. doi: 10.1021/cs401052k10.1021/cs401052k ↗
2. Filice M, Palomo JM (2014) Cascade reactions catalyzed by bionanostructures. ACS Catal 4(5):1588–1598. doi: 10.1021/cs401005y10.1021/cs401005y ↗
3. Vaccari A (1999) Clays and catalysis: a promising future. Appl Clay Sci 14(4):161–198. doi: 10.1016/S0169-1317(98)00058-110.1016/S0169-1317(98)00058-1 ↗
4. Cavani F, Trifirò F, Vaccari A (1991) Hydrotalcite-type anionic clays: preparation, properties and applications. Catal Today 11(2):173–301. doi: 10.1016/0920-5861(91)80068-K10.1016/0920-5861(91)80068-K ↗
5. Fan G, Li F, Evans DG, Duan X (2014) Catalytic applications of layered double hydroxides: recent advances and perspectives. Chem Soc Rev 43(20):7040–7066. doi: 10.1039/c4cs00160e10.1039/c4cs00160e ↗
6. Debecker DP, Gaigneaux EM, Busca G (2009) Exploring, tuning, and exploiting the basicity of hydrotalcites for applications in heterogeneous catalysis. Chem-Eur J 15(16):3920–3935. doi: 10.1002/chem.20090006010.1002/chem.200900060 ↗
7. Tichit D, Coq B (2003) Catalysis by hydrotalcites and related materials. Cattech 7(6):206–217. doi: 10.1023/b:catt.0000007166.65577.3410.1023/b:catt.0000007166.65577.34 ↗
8. Abello S, Medina F, Tichit D, Perez-Ramirez J, Cesteros Y, Salagre P, Sueiras JE (2005) Nanoplatelet-based reconstructed hydrotalcites: towards more efficient solid base catalysts in aldol condensations. Chem Commun 11:1453–1455. doi: 10.1039/b417322h10.1039/b417322h ↗
9. Abello S, Medina F, Tichit D, Perez-Ramirez J, Groen JC, Sueiras JE, Salagre P, Cesteros Y (2005) Aldol condensations over reconstructed Mg-Al hydrotalcites: structure-activity relationships related to the rehydration method. Chem-Eur J 11(2):728–739. doi: 10.1002/chem.20040040910.1002/chem.200400409 ↗
10. Álvarez MG, Chimentão RJ, Barrabés N, Föttinger K, Gispert-Guirado F, Kleymenov E, Tichit D, Medina F (2013) Structure evolution of layered double hydroxides activated by ultrasound induced reconstruction. Appl Clay Sci 83–84:1–11. doi: 10.1016/j.clay.2013.08.00610.1016/j.clay.2013.08.006 ↗
11. Chimentão RJ, Abelló S, Medina F, Llorca J, Sueiras JE, Cesteros Y, Salagre P (2007) Defect-induced strategies for the creation of highly active hydrotalcites in base-catalyzed reactions. J Catal 252(2):249–257. doi: 10.1016/j.jcat.2007.09.01510.1016/j.jcat.2007.09.015 ↗
12. Capps SM, Clarke TP, Charmant JPH, Hoppe HAF, Lloyd-Jones GC, Murray M, Peakman TM, Stentiford RA, Walsh KE, Worthington PA (2000) Highly substituted homoallylvinylcyclopropanes by indium-mediated reaction of alpha, beta-unsaturated ketones and aldehydes with allylic halides. Eur J Org Chem 6:963–97410.1002/(SICI)1099-0690(200003)2000:6<963::AID-EJOC963>3.0.CO;2-1 ↗
13. H-f Xu, Zhong H, Wang S, F-x Li (2015) One-pot synthesis of cyclic aldol tetramer and alpha, beta-unsaturated aldol from linear aldehydes using quaternary ammonium combined with sodium hydroxide as catalysts. J Cent South Univ 22(6):2081–2087. doi: 10.1007/s11771-015-2732-210.1007/s11771-015-2732-2 ↗
14. Sels BF, De Vos DE, Jacobs PA (2001) Hydrotalcite-like anionic clays in catalytic organic reactions. Catal Rev-Sci Eng 43(4):443–488. doi: 10.1081/cr-12000180910.1081/cr-120001809 ↗
15. Barrett CJ, Chheda JN, Huber GW, Dumesic JA (2006) Single-reactor process for sequential aldol-condensation and hydrogenation of biomass-derived compounds in water. Appl Catal B 66(1–2):111–118. doi: 10.1016/j.apcatb.2006.03.00110.1016/j.apcatb.2006.03.001 ↗
16. Hora L, Kelbichova V, Kikhtyanin O, Bortnovskiy O, Kubicka D (2014) Aldol condensation of furfural and acetone over Mg-Al layered double hydroxides and mixed oxides. Catal Today 223:138–147. doi: 10.1016/j.cattod.2013.09.02210.1016/j.cattod.2013.09.022 ↗
17. Yadav GD, Aduri P (2012) Aldol condensation of benzaldehyde with heptanal to jasminaldehyde over novel Mg-Al mixed oxide on hexagonal mesoporous silica. J Mol Catal A 355:142–154. doi: 10.1016/j.molcata.2011.12.00810.1016/j.molcata.2011.12.008 ↗
18. Hora L, Kikhtyanin O, Čapek L, Bortnovskiy O, Kubička D (2015) Comparative study of physico-chemical properties of laboratory and industrially prepared layered double hydroxides and their behavior in aldol condensation of furfural and acetone. Catal Today 241:221–230. doi: 10.1016/j.cattod.2014.03.010 Part B10.1016/j.cattod.2014.03.010 ↗
19. Tichit D, Lutic D, Coq B, Durand R, Teissier R (2003) The aldol condensation of acetaldehyde and heptanal on hydrotalcite-type catalysts. J Catal 219(1):167–175. doi: 10.1016/S0021-9517(03)00192-110.1016/S0021-9517(03)00192-1 ↗
20. Corma A, Garcia H (2003) Lewis acids: from conventional homogeneous to green homogeneous and heterogeneous catalysis. Chem Rev 103(11):4307–4365. doi: 10.1021/cr030680z10.1021/cr030680z ↗
21. Climent MJ, Corma A, Iborra S, Epping K, Velty A (2004) Increasing the basicity and catalytic activity of hydrotalcites by different synthesis procedures. J Catal 225(2):316–326. doi: 10.1016/j.jcat.2004.04.02710.1016/j.jcat.2004.04.027 ↗
22. Crespo I, Barriga C, Ulibarri MA, Gonzalez-Bandera G, Malet P, Rives V (2001) An X-ray diffraction and absorption study of the phases formed upon calcination off Zn-Al-Fe hydrotalcites. Chem Mater 13(5):1518–1527. doi: 10.1021/cm001085610.1021/cm0010856 ↗
23. Kloprogge JT, Hickey L, Frost RL (2004) The effects of synthesis pH and hydrothermal treatment on the formation of zinc aluminum hydrotalcites. J Solid State Chem 177(11):4047–4057. doi: 10.1016/j.jssc.2004.07.01010.1016/j.jssc.2004.07.010 ↗
24. Yang K, LG Yan, Yang YM, Yu SJ, Shan RR, Yu HQ, Zhu BC, Du B (2014) Adsorptive removal of phosphate by Mg–Al and Zn–Al layered double hydroxides: kinetics, isotherms and mechanisms. Sep Purif Technol 124:36–42. doi: 10.1016/j.seppur.2013.12.04210.1016/j.seppur.2013.12.042 ↗
25. Vieira AC, Moreira RL, Dias A (2009) Raman scattering and fourier transform infrared spectroscopy of Me6Al2(OH)16Cl2·4H2O (Me=Mg, Ni, Zn Co, and Mn) and Ca2Al(OH)6Cl·4H2O Hydrotalcites. J Phys Chem C 113(30):13358–13368. doi: 10.1021/jp902566r10.1021/jp902566r ↗
26. Shannon RD (1976) Revised effective ionic radii and systematic studies of interatomic distances in halides and chalcogenides. Acta Crystallogr A 32:751–76710.1107/S0567739476001551 ↗
27. Valente JS, Tzompantzi F, Prince J, Cortez JGH, Gomez R (2009) Adsorption and photocatalytic degradation of phenol and 2,4 dichlorophenoxiacetic acid by Mg–Zn–Al layered double hydroxides. Appl Catal B 90(3–4):330–338. doi: 10.1016/j.apcatb.2009.03.01910.1016/j.apcatb.2009.03.019 ↗
28. Vaccari A (1998) Preparation and catalytic properties of cationic and anionic clays. Catal Today 41(1–3):53–71. doi: 10.1016/S0920-5861(98)00038-810.1016/S0920-5861(98)00038-8 ↗
29. Sanchez-Cantu M, Perez-Diaz LM, Rubio-Rosas E, Abril-Sandoval VH, Merino-Aguirre JG, Reyes-Cruz FM, Orea L (2014) MgZnAl hydrotalcite-like compounds preparation by a green method: effect of zinc content. Chem Papers 68(5):638–649. doi: 10.2478/s11696-013-0491-910.2478/s11696-013-0491-9 ↗
30. Lee G, Jeong Y, Takagaki A, Jung JC (2014) Sonication assisted rehydration of hydrotalcite catalyst for isomerization of glucose to fructose. J Mol Catal A 393:289–295. doi: 10.1016/j.molcata.2014.06.01910.1016/j.molcata.2014.06.019 ↗
31. Dębek R, Radlik M, Motak M, Galvez ME, Turek W, Da Costa P, Grzybek T (2015) Ni-containing Ce-promoted hydrotalcite derived materials as catalysts for methane reforming with carbon dioxide at low temperature—on the effect of basicity. Catal Today 257:59–65. doi: 10.1016/j.cattod.2015.03.017 Part 110.1016/j.cattod.2015.03.017 ↗
32. Pavel OD, Tichit D, Marcu I-C (2012) Acido-basic and catalytic properties of transition-metal containing Mg–Al hydrotalcites and their corresponding mixed oxides. Appl Clay Sci 61:52–58. doi: 10.1016/j.clay.2012.03.00610.1016/j.clay.2012.03.006 ↗
33. Di Cosimo JI, Díez VK, Xu M, Iglesia E, Apesteguía CR (1998) Structure and surface and catalytic properties of Mg-Al basic oxides. J Catal 178(2):499–510. doi: 10.1006/jcat.1998.216110.1006/jcat.1998.2161 ↗
34. Liu P, Derchi M, Hensen EJM (2014) Promotional effect of transition metal doping on the basicity and activity of calcined hydrotalcite catalysts for glycerol carbonate synthesis. Appl Catal B 144:135–143. doi: 10.1016/j.apcatb.2013.07.01010.1016/j.apcatb.2013.07.010 ↗
35. Di Cosimo JI, Apesteguía CR, Ginés MJL, Iglesia E (2000) Structural requirements and reaction pathways in condensation reactions of alcohols on MgyAlOx catalysts. J Catal 190(2):261–275. doi: 10.1006/jcat.1999.273410.1006/jcat.1999.2734 ↗
36. Shen J, Tu M, Hu C (1998) Structural and surface acid/base properties of hydrotalcite-derived MgAlO oxides calcined at varying temperatures. J Solid State Chem 137(2):295–301. doi: 10.1006/jssc.1997.773910.1006/jssc.1997.7739 ↗
37. Bezen MCI, Breitkopf C, Lercher JA (2011) On the acid–base properties of Zn–Mg–Al mixed oxides. Appl Catal A 399(1–2):93–99. doi: 10.1016/j.apcata.2011.03.05310.1016/j.apcata.2011.03.053 ↗
38. Rossi TM, Campos JC, Souza MMVM (2016) CO2 capture by Mg-Al and Zn-Al hydrotalcite-like compounds. Adsorption 22(2):151–158. doi: 10.1007/s10450-015-9732-210.1007/s10450-015-9732-2 ↗
39. Climent MJ, Corma A, Iborra S, Velty A (2004) Activated hydrotalcites as catalysts for the synthesis of chalcones of pharmaceutical interest. J Catal 221(2):474–482. doi: 10.1016/j.jcat.2003.09.01210.1016/j.jcat.2003.09.012 ↗
40. Sharma SK, Parikh PA, Jasra RV (2007) Solvent free aldol condensation of propanal to 2-methylpentenal using solid base catalysts. J Mol Catal A 278(1–2):135–144. doi: 10.1016/j.molcata.2007.09.00210.1016/j.molcata.2007.09.002 ↗
41. Díez VK, Di Cosimo JI, Apesteguía CR (2008) Study of the citral/acetone reaction on MgyAlOx oxides: effect of the chemical composition on catalyst activity, selectivity and stability. Appl Catal A 345(2):143–151. doi: 10.1016/j.apcata.2008.04.03510.1016/j.apcata.2008.04.035 ↗
42. Aramendia MA, Borau V, Jimenez C, Marinas JM, Ruiz JR, Urbano F (2003) Reduction of alpha, beta-unsaturated aldehydes with basic MgO/M2O3 catalysts (M=Al, Ga, In). Appl Catal A 249(1):1–9. doi: 10.1016/s0926-860x(03)00163-710.1016/s0926-860x(03)00163-7 ↗
43. Hidalgo JM, Jimenez-Sanchidrian C, Rafael Ruiz J (2014) Delaminated layered double hydroxides as catalysts for the Meerwein-Ponndorf-Verley reaction. Appl Catal A 470:311–317. doi: 10.1016/j.apcata.2013.11.00710.1016/j.apcata.2013.11.007 ↗
44. Mora M, Isabel Lopez M, Jimenez-Sanchidrian C, Rafael Ruiz J (2010) Ca/Al mixed oxides as catalysts for the Meerwein-Ponndorf-Verley Reaction. Catal Lett 136(3–4):192–198. doi: 10.1007/s10562-010-0329-910.1007/s10562-010-0329-9 ↗