Citation: LIU Ning, WANG Danfeng, WU Suyun, LIU Shuilin, FU Lin, LIU Yuejin. Catalytic Synthesis of Bisphenol F over Short-Channeled Mesoporous Molecular Sieve Zr-Ce-SBA-15 Supported Acidic Ionic Liquids[J]. Chinese Journal of Applied Chemistry, ;2020, 37(9): 1038-1047. doi: 10.11944/j.issn.1000-0518.2020.09.200055 shu

Catalytic Synthesis of Bisphenol F over Short-Channeled Mesoporous Molecular Sieve Zr-Ce-SBA-15 Supported Acidic Ionic Liquids

LIU Ning ^a,, ,
WANG Danfeng ^b ,
WU Suyun ^a ,
LIU Shuilin ^a ,
FU Lin ^b ,
LIU Yuejin ^b,,

a.
Department of Materials and Chemical Engineering, New Building Materials Academy, Hunan Institute of Technology, Hengyang, Hunan 421002, China
b.
School of Chemical Engineering, National&Local United Engineering Research Centre for Chemical Process Simulation and Intensification, Xiangtan University, Xiangtan, Hunan 411105, China

Corresponding author: LIU Ning, liuning0731@163.com LIU Yuejin, xdlyj@163.com
Received Date: 28 February 2020
Revised Date: 24 April 2020
Accepted Date: 3 June 2020

Fund Project: Supported by the National Natural Science Foundation of China(No.21878255.), the Hunan Provincial Natural Science Foundation of China(No.2020JJ5117, No.2019JJ50107, No.2016JJ4028), the Foundation of Hunan Educational Committee(No.18B465), the Talent Scientific Research Fund of Hunan Institute of Technology(No.HQ 17014, No.HQ 17011), the Foundation of Key Laboratory of Functional Metal-Organic Compounds of Hunan Province(No.MO20K02), and the Characteristic Application Discipline of Material Science and Engineering in Hunan(No.Xiang-Jiao-Tong[2018]369)

Figures(7)

Two supported acidic ionic liquids (ILs) consisting of SBA-15-ILs (SILs) and Zr-Ce-SBA-15-ILs(ZCSILs) were prepared by combining acidic ionic liquids with the silica-based support. The physio-chemical properties of the obtained catalysts were characterized by Fourier transform infrared (FT-IR) spectroscopy, thermalgravimetry-differential thermal gravimetry (TG-DTG), X-ray diffraction (XRD), Brunauer Emmett Teller (BET), transimition electron microscopy (TEM), scanning electron microscopy (SEM) and organic elemental analysis (OEA) measurements. The catalytic activity of the prepared catalysts was evaluated in the hydroxyalkylation of phenol and aqueous formaldehyde to bisphenol F. The effects of operating variables, such as type of catalysts, molar ratio of phenol to formaldehyde, reaction temperature, reaction time and addition of catalysts on the yield of BPF and selectivity were investigated. Under the optimum conditions (catalyst/formaldehyde mass ratio 0.36, phenol/formaldehyde molar ratio 30:1, reaction temperature 80 ℃ and reaction time 60 min), a high bisphenol F yield of 95.6% with 44.8% selectivity to 4, 4'-BPF can be achieved over the short-channeled ZCSILs catalyst with large specific surface area and high loading amount of ionic liquids and its catalytic activity is still good after being reused for 5 times.
- short channeled,
- acid ionic liquids,
- Zr-Ce-SBA-15,
- bisphenol F,
- selectivity
1. [1]
  Li C, Cai H, Zhang B. Tailored One-Pot Production of Furan-Based Fuels from Fructose in an Ionic Liquid Biphasic Solvent System[J]. Chinese J Catal, 2015,36:1638-1646. doi: 10.1016/S1872-2067(15)60927-5
2. [2]
  LI Changzhi, WANG Aiqin, ZHANG Tao. Progress of Conversion of Cellulose Resource in Ionic Liquids[J]. CIESC J, 2013,64(1):182-197.
3. [3]
  QU Haonan, BAO Chong, MA Wenjing. Hydrolysis of Cellulose by Solid Carbon Sulfonic acid Supported 1-Butyl-3-methylimidazolium Chloride[J]. Chinese J Appl Chem, 2019,36(1):58-64.
4. [4]
  SHAN Ruoni, CUI Xing, DING Qi. Racemic Metoprolol Separation by Enantioselective Liquid-Liquid Extraction with Amino Acid Ionic Liquids[J]. J Chem Eng Chinese Uinv, 2019,33(6):1444-1449.
5. [5]
  Li T, Yan X, Liu J. Friedel-Crafts Alkylation Route for Preparation of Pendent Side Chain Imidazolium-Functionalized Polysulfone Anion Exchange Membranes for Fuel Cells[J]. J Membr Sci, 2019,573:157-166. doi: 10.1016/j.memsci.2018.11.079
6. [6]
  Yang J, Feng Y, Zeng T. Synthesis of Biodiesel via Transesterification of Tung Oil Catalyzed by New Brönsted Acidic Ionic Liquid[J]. Chem Eng Res Des, 2017,117:584-592. doi: 10.1016/j.cherd.2016.09.038
7. [7]
  Miao C, Hou Q, Wen Y. Long-Chained Acidic Ionic Liquids-Catalyzed Cyclization of 2-Substituted Aminoaromatics with β-Diketones:A Metal-Free Strategy to Construct Benzoazoles[J]. ACS Sustainable Chem Eng, 2019,7(14):12008-12013.
8. [8]
  Yue S, Wang P, Hao X. Synthesis of Cyclic Carbonate from CO₂ and Epoxide Using Bifunctional Imidazolium Ionic Liquid Under Mild Conditions[J]. Fuel, 2019,251:233-241. doi: 10.1016/j.fuel.2019.04.039
9. [9]
  Chiappe C, Rodriguez Douton M J, Mezzetta A. Recycle and Extraction:Cornerstones for an Efficient Conversion of Cellulose into 5-Hydroxymethylfurfural in Ionic Liquids[J]. ACS Sustainable Chem Eng, 2017,5(6):5529-5536. doi: 10.1021/acssuschemeng.7b00875
10. [10]
  Jiang B, Yang H, Zhang L. Efficient Oxidative Desulfurization of Diesel Fuel Using Amide-Based Ionic Liquids[J]. Chem Eng J, 2016,283:89-96. doi: 10.1016/j.cej.2015.07.070
11. [11]
  Yang H, Jiang B, Sun Y. Synthesis and Oxidative Desulfurization of Novel Lactam-Based Brönsted-Lewis Acidic Ionic Liquids[J]. Chem Eng J, 2016,306:131-138. doi: 10.1016/j.cej.2016.07.044
12. [12]
  Sarma B, Srivastava R. Highly Efficient and Recyclable Basic Ionic Liquids Supported on SBA-15 for the Synthesis of Substituted Styrenes, Carbinolamides, and Naphthopyrans[J]. Mol Catal, 2017,427:62-72. doi: 10.1016/j.molcata.2016.11.030
13. [13]
  Zhao Q, Yang C, Fang M. Performance of Brönsted-Lewis Acidic Ionic liquids Supported Ti-SBA-15 for the Esterification of Acetic Acid to Benzyl Alcohol[J]. Appl Catal A:Gen, 2020117470.
14. [14]
  Zhou Y, Liu J, Huang R. Covalently Immobilized Ionic Liquids on Single Layer Nanosheets for Heterogeneous Catalysis Applications[J]. Dalton Trans, 2017,46(38):13126-13134. doi: 10.1039/C7DT01510K
15. [15]
  Zhou Q, Chen F, Wu W. Reactive Orange 5 Removal from Aqueous Solution Using Hydroxyl Ammonium Ionic Liquids/Layered Double Hydroxides Intercalation Composites[J]. Chem Eng J, 2016,285:198-206. doi: 10.1016/j.cej.2015.10.004
16. [16]
  Yoshida Y, Fujie K, Lim D W. Superionic Conduction over a Wide Temperature Range in a Metal-Organic Framework Impregnated with Ionic Liquids[J]. Angew Chem Int Ed, 2019,58(32):10909-10913. doi: 10.1002/anie.201903980
17. [17]
  Jiang T, Fang M, Li Y. Alkylation of Phenol/tert-Butyl Alcohol on Ionic Liquid-Immobilized SBA-15 with Different Pore Sizes[J]. J Taiwan Inst Chem E, 2017,80:1031-1040. doi: 10.1016/j.jtice.2017.09.029
18. [18]
  He Y, Zhang Q, Zhan X. Synthesis of Efficient SBA-15 Immobilized Ionic Liquid Catalyst and Its Performance for Friedel-Crafts Reaction[J]. Catal Today, 2016,276:112-120. doi: 10.1016/j.cattod.2016.01.045
19. [19]
  Dai L, Zhao Q, Fang M. Catalytic Activity Comparison of Zr-SBA-15 Immobilized by a Brönsted-Lewis Acidic Ionic Liquid in Different Esterifications[J]. RSC Adv, 2017,7(51):32427-32435. doi: 10.1039/C7RA04950A
20. [20]
  Wang Y, Chen Z, Yu F. Preparation of Epoxy-Acrylic Latex Based on Bisphenol F Epoxy Resin[J]. J Macromol Sci A, 2018,55(2):205-212. doi: 10.1080/10601325.2017.1410065
21. [21]
  Tan Y, Li Y, Wei Y. The Hydroxyalkylation of Phenol with Formaldehyde over Mesoporous M (Al, Zr, Al-Zr)-SBA-15 Catalysts:The Effect on the Isomer Distribution of Bisphenol F[J]. Catal Commun, 2015,67:21-25. doi: 10.1016/j.catcom.2015.03.019
22. [22]
  Wei Y, Li Y, Tan Y. Short-channeled Mesoporous Zr-Al-SBA-15 as a Highly Efficient Catalyst for Hydroxyalkylation of Phenol with Formaldehyde to Bisphenol F[J]. Chem Eng J, 2016,298:271-280. doi: 10.1016/j.cej.2016.04.038
23. [23]
  Wang D, He Z, Wu Z. Highly Selective Synthesis for 4, 4'-Bisphenol F from Phenol and Formaldehyde Catalyzed with[J]. Chinese J Chem Eng, 2016,24(9):1166-1170. doi: 10.1016/j.cjche.2016.02.005
24. [24]
  Çitak A, Erdem B, Erdem S. Synthesis, Characterization and Catalytic Behavior of Functionalized Mesoporous SBA-15 with Various Organo-silanes[J]. J Colloid Interface Sci, 2012,369(1):160-163. doi: 10.1016/j.jcis.2011.11.070
25. [25]
  Halamová D, Badaničová M, Zeleňák V. Naproxen Drug Delivery Using Periodic Mesoporous Silica SBA-15[J]. Appl Surf Sci, 2010,256:6489-6494. doi: 10.1016/j.apsusc.2010.04.044
26. [26]
  Xie W, Fan M. Biodiesel Production by Transesterification Using Tetraalkylammonium Hydroxides Immobilized onto SBA-15 as a Solid Catalyst[J]. Chem Eng J, 2014,239:60-67. doi: 10.1016/j.cej.2013.11.009
27. [27]
  Garade A C, Kshirsagar V S, Rode C V. Selective Hydroxyalkylation of Phenol to Bisphenol F over Dodecatungstophosphoric Acid(DTP) Impregnated on Fumed Silica[J]. Appl Catal A:Gen, 2009,354(1):176-182.
28. [28]
  Jana S K, Kugita T, Namba S. Aluminum-Grafted MCM-41 Molecular Sieve:An Active Catalyst for Bisphenol F Synthesis Process[J]. Appl Catal A:Gen, 2004,266(2):245-250. doi: 10.1016/j.apcata.2004.02.013
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