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A novel hydrogen-bonded silica-supported acidic ionic liquid: An efficient, recyclable and selective heterogeneous catalyst for the synthesis of diesters

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Abstract

In this study, two novel acidic ionic liquids, including a hydroxyl functionalized diacidic ionic liquid [HFDAIL] and a sulfonated diacidic ionic liquid [SFDAIL], were prepared and immobilized on the surface of silica nanoparticles (SNPs) via hydrogen bonding. The materials were characterized by FT-IR, NMR, SEM, nitrogen physisorption measurement, TGA and acid-base titration. The catalytic activity of the prepared catalysts was investigated in the synthesis of phthalate, maleate and succinate diesters under solvent-free conditions. It was found that nanosilica@[HFDAIL] with higher availability of acidic sites and higher hydrophilicity was more efficient compared to the nanosilica@[SFDAIL]. Notably, nanosilica@[HFDAIL] catalyst has also demonstrated excellent selectivity for the diester product while the monoester product was predominant in the case of nanosilica@[SFDAIL] even after prolonged reaction time or higher catalyst loading. In addition, the nanosilica@[HFDAIL] catalyst could be separated by simple filtration and reused several times without any significant loss of catalytic performance, but a remarkable decrease in activity was observed for nanosilica@[SFDAIL] in the next runs.

GRAPHICAL ABSTRACT 

SYNOPSIS Two novel acidic ionic liquids, including a hydroxyl functionalized diacidic ionic liquid [HFDAIL] and a sulfonated diacidic ionic liquid [SFDAIL], were prepared and immobilized on the surface of silica nanoparticles via hydrogen bonding. The catalytic activity of the catalysts was investigated in the synthesis of diesters under solvent-free conditions.

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References

  1. Lee A F, Bennett J A, Manayila J C and Wilson K 2014 Heterogeneous catalysis for sustainable biodiesel production via esterification and transesterification Chem. Soc. Rev. 43 7887

    Article  CAS  PubMed  Google Scholar 

  2. Joseph T, Sahoo S and Halligudi S B 2005 Brønsted acidic ionic liquids: a green, efficient and reusable catalyst system and reaction medium for Fischer esterification J. Mol. Catal. A-Chem. 234 107

    Article  CAS  Google Scholar 

  3. Kulawska M, Moroz H and Kasprzyk A 2011 Kinetic investigations on the esterification of phthalic anhydride with n-heptyl, n-nonyl or n-undecyl alcohol over sulfuric acid catalyst React. Kinet. Mech. Cat. 104 9

    Article  CAS  Google Scholar 

  4. Patil M S, Gurudasani V D and Usmani G A 2010 Esterification of phthalic anhydride with n-Butanol using eco-friendly solid acid catalyst-sulfamic acid Curr. World Environ. 5 107

    Article  CAS  Google Scholar 

  5. Awang R, Basri M, Ahmad S and Salleh A B 2000 Enzymatic esterification of dihydroxystearic acid J. Am. Oil Chem. Soc. 77 609

    Article  CAS  Google Scholar 

  6. Xing H B, Wang T, Zhou Z H and Dai Y Y 2005 Novel Brønsted- acidic ionic liquids for esterification Ind. Eng. Chem. Res. 44 4147

    Article  CAS  Google Scholar 

  7. Gui J Z, Cong X H, Liu D, Zhang X T, Hu Z D and Sun Z L 2004 Novel Brønsted acidic ionic liquid as efficient and reusable catalyst system for esterification Catal. Commun. 5 473

    Article  CAS  Google Scholar 

  8. Yang J, Zhou L, Guo X, Li L, Zhang P, Hong R and Qiu T 2015 Study on the esterification for ethylene glycol diacetate using supported ionic liquids as catalyst: catalysts preparation, characterization, and reaction kinetics Chem. Eng. J. 280 147

    Article  CAS  Google Scholar 

  9. Muskawar P N, Thenmozhi K, Gajbhiye J M and Bhagat P R 2014 Facile esterification of carboxylic acid using amide functionalized benzimidazolium dicationic ionic liquids Appl. Catal. A-Gen 482 214

    Article  CAS  Google Scholar 

  10. Liu B, Zhou R, Bu N, Wang Q, Zhong S, Wang B and Hidetoshi K 2017 Room-temperature ionic liquids modified zeolite SSZ-13 membranes for \(\text{ CO }_{2}/\text{ CH }_{4}\) separation J. Membr. Sci. 524 12

    Article  CAS  Google Scholar 

  11. Vekariya R L 2017 A review of ionic liquids: applications towards catalytic organic transformations J. Mol. Liq. 227 44

    Article  CAS  Google Scholar 

  12. Toniolo R, Bortolomeazzi R, Svigelj R, Dossi N, Casella I G, Bragato C and Daniele S 2017 Use of an electrochemical room temperature ionic liquid-based microprobe for measurements in gaseous atmospheres Sensor. Actuat. B-Chem. 240 239

    Article  CAS  Google Scholar 

  13. Fareghi-Alamdari R, Ghorbani-Zamani F and Zekri N 2014 An efficient and highly selective ortho-tert-butylation of p-cresol with methyl tert-butyl ether catalyzed by sulfonated ionic liquids J. Serb. Chem. Soc. 79 1337

    Article  CAS  Google Scholar 

  14. Romero C and Baldelli S 2006 Sum frequency generation study of the room-temperature ionic liquids/quartz interface J. Phys. Chem. B 110 6213

    Article  CAS  PubMed  Google Scholar 

  15. Welton T 2004 Ionic liquids in catalysis Coordin. Chem. Rev. 248 2459

    CAS  Google Scholar 

  16. Brennecke J F and Maginn E J 2001 Ionic liquids: innovative fluids for chemical processing AlChE J. 47 2384

    Article  CAS  Google Scholar 

  17. Olivier-Bourbigou H and Magna L 2002 Ionic liquids: perspectives for organic and catalytic reactions J. Mol. Catal. A-Chem. 182-183 419

    Article  Google Scholar 

  18. Marsh K N, Boxall J A and Lichtenthaler R 2004 Room temperature ionic liquids and their mixtures- a review Fluid Phase Equilibr. 219 93

    Article  CAS  Google Scholar 

  19. Sahoo S, Kumar P, Lefebvre F and Halligudi S B 2009 Oxidative kinetic resolution of alcohols using chiral Mn–salen complex immobilized onto ionic liquid modified silica Appl. Catal. A-Gen 354 17

    Article  CAS  Google Scholar 

  20. Chen W, Zhang Y Y, Zhu L B, Lan J B, Xie R G and You J S 2007 A concept of supported amino acid ionic liquids and their application in metal scavenging and heterogeneous catalysis J. Am. Chem. Soc. 129 13879

    Article  CAS  PubMed  Google Scholar 

  21. Giacalone F and Gruttadauria M 2016 Covalently supported ionic liquid phases: an advanced class of recyclable catalytic systems ChemCatChem 8 664

    Article  CAS  Google Scholar 

  22. Sidhpuria K, Daniel-da-silva L, Trindade T and Coutinho A P 2011 Supported ionic liquid silica nanoparticles (SILnPs) as an efficient and recyclable heterogeneous catalyst for the dehydration of fructose to 5- hydroxymethylfural Green Chem. 13 340

    Article  CAS  Google Scholar 

  23. Karimi B and Vafaeezadeh M 2012 SBA-15-functionalized sulfonic acid confined acidic ionic liquid: a powerful and water-tolerant for solvent-free esterifications Chem. Commun. 48 3327

    Article  CAS  Google Scholar 

  24. Vafaeezadeh M, Bahrami Dizicheh Z and Mahmoodi Hashemi M 2013 Mesoporous silica-functionalized dual Brønsted acidic ionic liquid as an efficient catalyst for thioacetalization of carbonyl compounds in water Catal. Commun. 41 96

    Article  CAS  Google Scholar 

  25. Karimi B and Vafaeezadeh M 2013 SBA-15 functionalized sulfonic acid containing a confined hydrophobic and acidic ionic liquid: a highly efficient catalyst for solvent-free thioacetalization of carbonyl compounds at room temperature RSC Adv. 3 23207

    Article  CAS  Google Scholar 

  26. Miao J, Wan H and Guan G 2011 Synthesis of immobilized Brønsted acidic ionic liquid on silica gel as heterogeneous catalyst for esterification Catal. Commun. 12 353

    Article  CAS  Google Scholar 

  27. Miao J, Wan H, Shao Y, Guan G and Xu B 2011 Acetalization of carbonyl compounds catalyzed by acidic ionic liquid immobilized on silica gel J. Mol. Catal. A-Chem. 348 77

    Article  CAS  Google Scholar 

  28. Shao Y, Wan H, Miao J and Guan G 2013 Synthesis of an immobilized Brønsted acidic ionic liquid catalyst on chloromethyl polystyrene grafted silica gel for esterification React. Kinet. Mech. Cat. 109 149

    Article  CAS  Google Scholar 

  29. Fareghi-Alamdari R, Ghorbani-Zamani F and Shekarriz M 2016 Surface passivation of bare boron nanoparticles using new dicyanamide-based dicationic ionic liquid Energ. Fuel 30 551

    Article  CAS  Google Scholar 

  30. Fareghi-Alamdari R, Ghorbani-Zamani F and Zekri N 2016 Synthesis and hypergolic activity evaluation of some new ammonium-imidazolium based ionic liquids RSC Adv. 6 26386

    Article  CAS  Google Scholar 

  31. Fareghi-Alamdari R, Ghorbani Zamani F and Shekarriz M 2015 Synthesis and thermal characterization of new ammonium–imidazolium dual dicyanamide-based ionic liquids J. Mol. Liq. 211 831

    Article  CAS  Google Scholar 

  32. Fareghi-Alamdari R, Hatefipour R, Rakhshi M and Zekri N 2016 Novel diol functionalized dicationic ionic liquids: synthesis, characterization and DFT calculations on H-bonding influence on thermophysical properties RSC Adv. 6 78636

    Article  CAS  Google Scholar 

  33. Fareghi-Alamdari R and Hatefipour R 2016 Detonation nanodiamond as a new option for reduction of the viscosity of one novel di-azide functionalized monocationic ionic liquid ChemistrySelect. 1 6277

    Article  CAS  Google Scholar 

  34. Fareghi-Alamdari R and Hatefipour R 2015 Synthesis and thermophysical characterization of novel azide functionalized imidazolium based ionic liquids Thermochim. Acta 617 172

    Article  CAS  Google Scholar 

  35. Zekri N, Fareghi-Alamdari R and Khodarahmi Z 2016 Functionalized dicationic ionic liquids: green and efficient alternatives for catalysts in phthalate plasticizers preparation J. Chem. Sci. 128 1277

    Article  CAS  Google Scholar 

  36. Leng Y, Jiang P and Wang J 2012 A novel Brønsted acidic heteropolyanion-based polymeric hybrid catalyst for esterification Catal. Commun. 25 41

    Article  CAS  Google Scholar 

  37. Yingwei Z, Zhen L and Chungu X 2011 Alkyl sulfonate functionalized ionic liquids: synthesis, properties, and their application in esterification Chin. J. Catal. 32 440

    Article  CAS  Google Scholar 

  38. Xie C, Li H, Li L, Yu S and Liu F 2008 Synthesis of plasticizer ester using acid-functionalized ionic liquid as catalyst J. Hazard. Mater. 151 847

    Article  CAS  PubMed  Google Scholar 

  39. Khalili E 2012 Efficient synthesis of symmetrical phthalate and maleate diesters using phosphinite ionic liquids J. Iran. Chem. Soc. 9 529

    Article  CAS  Google Scholar 

  40. Zhao D, Liu M, Zhang J, Li J and Ren P 2013 Synthesis, characterization and properties of imidazole dicationic ionic liquids and their application in esterification Chem. Eng. J. 221 99

    Article  CAS  Google Scholar 

  41. Li H, Yu S, Liu F, Xie C and Li L 2007 Synthesis of dioctyl phthalate using acid functionalized ionic liquid as catalyst Catal. Commun. 8 1759

    Article  CAS  Google Scholar 

  42. Zhu H, Yang F, Tang J and He M 2003 Brønsted acidic ionic liquid 1-methylimidazolium tetrafluoroborate: a green catalyst and recyclable medium for esterification Green Chem. 5 38

    Article  CAS  Google Scholar 

  43. Dubreuil J, Bourahla K, Rahmouni M, Bazureau J P and Hamelin J 2002 Catalysed esterifications in room temperature ionic liquids with acidic counteranion as recyclable reaction media Catal. Commun. 3 185

    Article  Google Scholar 

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Acknowledgements

The financial assistance from the Malek-Ashtar University of Technology (MUT), Tehran, Iran, is gratefully acknowledged.

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Authors and Affiliations

  1. Faculty of Chemistry and Chemical Engineering, Malek-Ashtar University of Technology, Tehran, Iran

    Reza Fareghi-Alamdari & Mehri Nadiri Niri

  2. Center for Research and Science Education, Organization for Educational Research and Planning, Tehran, Iran

    Hassan Hazarkhani

Authors
  1. Reza Fareghi-Alamdari
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  2. Mehri Nadiri Niri
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  3. Hassan Hazarkhani
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Corresponding author

Correspondence to Reza Fareghi-Alamdari.

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Fareghi-Alamdari, R., Niri, M.N. & Hazarkhani, H. A novel hydrogen-bonded silica-supported acidic ionic liquid: An efficient, recyclable and selective heterogeneous catalyst for the synthesis of diesters. J Chem Sci 130, 48 (2018). https://doi.org/10.1007/s12039-018-1454-z

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  • DOI: https://doi.org/10.1007/s12039-018-1454-z

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