Citation: YANGYANG Jia-zi, ZHOU Feng, MA Hui-xia, LI Xue-lei, YUAN Xing-zhou, LIANG Fei-xue, ZHANG Jian. One step synthesis of 2, 5-furandicarboxylic acid from fructose catalyzed by Ce modified Ru/HAP[J]. Journal of Fuel Chemistry and Technology, ;2020, 48(8): 942-948. shu

One step synthesis of 2, 5-furandicarboxylic acid from fructose catalyzed by Ce modified Ru/HAP

1.
Liaoning Petrochemical University, Fushun 113001, China
2.
Dalian Research Institute of Petroleum and Petrochemicals, Dalian 116000, China
3.
Yingkou Institute of Tecnology, Yingkou 115014, China

Corresponding author: ZHANG Jian, zhangjian-lnpu@163.com
Received Date: 9 June 2020
Revised Date: 21 July 2020

Figures(8)

A series of Ce-modified Ru/HAP catalysts with different loadings were prepared by impregnation method, which were applied to the one-step preparation of 2, 5-furandicarboxylic acid with fructose. The catalysts were characterized by XRD, TEM, NH₃-TPD and XPS. The results showed that Ce was highly dispersed on the HAP, and the addition of Ce affected little on the structure of HAP. Ce mainly exists in the form of Ce³⁺ and Ce⁴⁺. The presence of the Ce³⁺ makes a large amount of oxygen holes on the surface of the catalyst, and the electron transfer between Ce³⁺ and Ce⁴⁺ is conducive to the formation of oxygen holes, improves the oxygen storage capacity and the surface catalytic activity. The catalyst is rich in weak acid sites, which inhibits the side reactions. Among the catalysts evaluated, the sample of Ce (8%, mass ratio) -Ru/HAP showed satisfied performance with the 2, 5-FDCA yield of 34.2% at 160℃ for 4 h reaction under a pressure of 2 MPa and a catalyst dosage of 0.1 g. Therefore, the introduction of Ce has greatly improved the catalytic activity of traditional precious metal composite catalysts, and also provided new ideas for the one-step preparation of fructose 2, 5-FDCA.
- Ce modified,
- 2, 5-furandicarboxylic acid,
- Ru/HAP,
- fructose
1. [1]
  SHEN G F, ZHANG S C, LEI Y, SHI J Q, XIA Y, MEI F M, CHEN Z Q, YIN G C. Catalytic carbonylation of renewable furfural derived 5-bromofurfural to 5-formyl-2-furancarboxylic acid in oil/aqueous bi-phase system[J]. Mol Catal, 2019,463:94-98. doi: 10.1016/j.mcat.2018.11.021
2. [2]
  ROMEN Y, CHHEDA A, DUMESIC J. Phase modifiers promote efficient production of Hydroxymethylfurfural from fructose[J]. Sci, 2006,312(5782):1933-1937. doi: 10.1126/science.1126337
3. [3]
  WANG Jian-gang, ZHANG Yun-yun, WANG Yong, ZHU Li-wei, CUI Hong-you, YI Wei-ming. Graded ordered porous sulfonated carbon catalyzed conversion of fructose to 5-hydroxymethylfurfural[J]. J Fuel Chem Technol, 2016,44(11):1341-1348.
4. [4]
  ZHU Li-wei, WANG Jian-gang, ZHAO Ping-ping, SONG Feng, SUN Xiu-yu, WANG Li-hong, CUI Hong-you, YI Wei-ming. Preparation of the Nb-P/SBA-15 catalyst and its performance in the dehydration of fructose to 5-hydroxyme thylfurfural[J]. J Fuel Chem Technol, 2017,45(6):651-659.
5. [5]
  BESSON M, PIERRE G, CATHERINE P. Conversion of biomass into chemicals over metal catalysts[J]. Chem Rev, 2014,114:1827-1870. doi: 10.1021/cr4002269
6. [6]
  DESSBESELL L, SOUZANCHI S, VENKATESWARA R, SADRA S. Production of 2, 5-furandicarboxylic acid (FDCA) from starch, glucose, or high-fructose corn syrup:Techno-economic analysis[J]. Biofuels Bioprod Bior, 2019,4(1):1-12.
7. [7]
  MONICA G, GANDINA A, SILVESTRE A, BRUNO R. Synthesis and characterization of poly (2, 5-furan dicarboxylates) based on a variety of diols[J]. J Polym Sci Poly Chem, 2011,49(17):3759-3768. doi: 10.1002/pola.24812
8. [8]
  KNOOP R, VOGELZANG W, HAVEREN J, VAN E, DAAN S. High molecular weight poly(ethylene-2, 5-furanoate); critical aspects in synthesis and mechanical property determination[J]. J Polym Sci Poly Chem, 2013,51(19):4191-4199. doi: 10.1002/pola.26833
9. [9]
  AMARASEKARA A, GREEN D, WILLIAMS L. Renewable resources based polymers:Synthesis and characterization of 2, 5-diformylfuran-urea resin[J]. Eur Polym J, 2009,45(2):595-598. doi: 10.1016/j.eurpolymj.2008.11.012
10. [10]
  GAO L, DENG K, ZHENG J, LIU B, ZHANG Z. Efficient oxidation of biomass derived 5-hydroxymethylfurfural into 2, 5-furandicarboxylic acid catalyzed by merrifield resin supported cobalt porphyrin[J]. Chem Eng J, 2015,270:444-449. doi: 10.1016/j.cej.2015.02.068
11. [11]
  CHEN Guang-yu, WU Lin-bo, LI Bo-geng. Research progress of synthesis of 2, 5-furandicarboxylic acid based on HMF route[J]. Chem Ind Eng Prog, 2018,37(8):3146-3154.
12. [12]
  YAN D X, WANG G Y, GAO K, LU X M, XIN J Y, ZHANG S J. One-Pot synthesis of 2, 5-Furandicarboxylic acid from fructose in ionic liquids[J]. Ind Eng Chem Res, 2018,57(6):1851-1858. doi: 10.1021/acs.iecr.7b04947
13. [13]
  LI C Z, CAI H L, ZHANG B, LI W Z, PEI G X, DAI T, WANG A Q, ZHANG T. Tailored one-pot production of furan-based fuels from fructose in an ionic liquid biphasic solvent system[J]. Chin J Catal, 2015,47(2):135-146.
14. [14]
  CHIDAMBARAM M, BELL A. A two-step approach for the catalytic conversion of glucose to 2, 5-dimethylfuran in ionic liquids[J]. Green Chem, 2010,12(7):1253-1262. doi: 10.1039/c004343e
15. [15]
  YI G S, TESONG S, LI X K, ZHANG Y G. Purification of biomass-derived 5-hydroxymethylfurfural and its catalytic conversion to 2, 5-Furandicarboxylic acid[J]. ChemSusChem, 2015,7(8):2131-2135.
16. [16]
  HAN X W, GENG L, GUO Y, JIA R, LIU X H, ZHANG Y G, WANG Y Q. Base-free aerobic oxidation of 5-hydroxymethylfurfural to 2, 5-furandicarboxylic acid over a Pt/C-O-Mg catalyst[J]. Green Chem, 2016,18(6):1597-1604. doi: 10.1039/C5GC02114F
17. [17]
  PASINI T, PICCININI M, BIOSI M, BONELLI R, ALBONETTI S, DIMITRATOS N, LOPEZSANCHEZ J. Selective oxidation of 5-hydroxymethyl-2-furfural using supported gold-copper nanoparticles[J]. Green Chem, 2011,13(8):2091-2099. doi: 10.1039/c1gc15355b
18. [18]
  GUPTA N, NISHIMURA S, TAKAGATI A, EBITANI K. Hydrotalcite-supported gold-nanoparticle-catalyzed highly efficient base-free aqueous oxidation of 5-hydroxymethylfurfural into 2, 5-furandicarboxylic acid under atmospheric oxygen pressure[J]. Green Chem, 2011,13(4):824-827.
19. [19]
  YI G S, ZHANG Y, TEONG S. Base-free conversion of 5-hydroxymethylfurfural to 2, 5-furandicarboxylic acid over a Ru/C catalyst[J]. Green Chem, 2016,18:977-983.
20. [20]
  AN J H, WANG Y H, XIN Z, ZHANG Z X, ZHANG J, MARTIN G, RAFAL E, DUNIN-BORKOWSKI R E, WANG F. Linear-regioselective hydromethoxycarbonylation of styrene using Ru-clusters/CeO₂ catalyst[J]. Chin J Catal, 2020,41(06):963-971. doi: 10.1016/S1872-2067(19)63527-8
21. [21]
  GAO T, CHEN J, FANG W, CAO Q, DUMEIGNIL F. Ru/Mn Ce1O catalysts with enhanced oxygen mobility and strong metal-support interaction:Exceptional performances in 5-hydroxymethylfurfural base-free aerobic oxidation[J]. J Catal, 2018,368:53-68. doi: 10.1016/j.jcat.2018.09.034
22. [22]
  YAN D X, XIN J Y, SHI C Y, LU X M, NI L L, WANG G Y, ZHANG S J. Base-free conversion of 5-hydroxymethylfurfural to 2, 5-furandicarboxylic acid in ionic liquids[J]. Chem Eng J, 2017,323:473-482. doi: 10.1016/j.cej.2017.04.021
23. [23]
  WANG S G, ZHANG Z H, LIU B, LI J L. Environmentally friendly oxidation of biomass derived 5-hydroxymethylfurfural into 2, 5-diformylfuran catalyzed by magnetic separation of ruthenium catalyst[J]. Ind Eng Chem Res, 2014,53(14):5820-5827. doi: 10.1021/ie500156d
24. [24]
  GOSWAMI S, MARIE D, RAGHAVAN V. Microwave assisted synthesis of 5-Hydroxymethylfurfural from starch in AlCl₃.6H₂O/DMSO/[BMIM]Cl system[J]. J Ind Eng Chem, 2016,55(16):4473-4481. doi: 10.1021/acs.iecr.6b00201
25. [25]
  CASANOVA , ONOFRE , IBORRA S, CORMA A. Biomass into chemicals:Aerobic oxidation of 5-Hydroxymethyl-2-furfural into 2, 5-Furandicarboxylic acid with gold nanoparticle catalysts[J]. ChemSusChem, 2009,2(12):1138-1144. doi: 10.1002/cssc.200900137
26. [26]
  VUYYURU K, STRASSER P. Oxidation of biomass derived 5-hydroxymethylfurfural using heterogeneous and electrochemical catalysis[J]. Catal Today, 2012,195(1):144-154. doi: 10.1016/j.cattod.2012.05.008
27. [27]
  YANG S X, ZHU W P, WANG J B, CHEN Z X. Catalytic wet air oxidation of phenol over CeO₂-TiO₂ catalyst in the batch reactor and the packed-bed reactor[J]. J Hazard Mater, 2008,153(3):1248-1253. doi: 10.1016/j.jhazmat.2007.09.084
28. [28]
  FEI Z Y, YANG Y R, WANG M B, TAO Z L, LIU Q, CHEN X, CUI M, ZHANG Z X, TANG J H, QIAO X. Precisely fabricating Ce-O-Ti structure to enhance performance of Ce-Ti based catalysts for selective catalytic reduction of NO with NH₃[J]. Chem Eng J, 2018,353:930-939. doi: 10.1016/j.cej.2018.07.198
29. [29]
  SU Y, TANG Z C, HAN W L, ZHANG P, SONG Y, LU G X. Influence of the pore structure of CeO₂ supports on the surface texture and catalytic activity for CO oxidation[J]. Crystengcomm, 2014,16(24):5189-5197. doi: 10.1039/c4ce00182f
30. [30]
  HAN X, LI C Q, LIU X H, XIA Q, WANG Y Q. Selective oxidation of 5-hydroxymethylfurfural to 2, 5-furandicarboxylic acid over MnOx-CeO₂ composite catalysts[J]. Green Chem, 2017,19(4):996-1004. doi: 10.1039/C6GC03304K
31. [31]
  TORRENTE L, GILBANK A, PUERTOLAS B, GARCIA T, SOLSONA B, CHADWICK D. Shape-dependency activity of nanostructured CeO in the total oxidation of polycyclic aromatic hydrocarbons[J]. Appl Catal B:Environ, 2013,132-133(15):116-122.
32. [32]
  NISHIUMI M, MIURA H, WADA K, HOSOKAWA S. Active ruthenium catalysts based on phosphine-modified Ru/CeO₂for the selective addition of carboxylic acids to terminal alkynes[J]. ACS Catal, 2012,2(8):1753-1759. doi: 10.1021/cs300151x
33. [33]
  MA Z X, YANG H S, LI Q, ZHENG Z W, ZHANG X B. Catalytic reduction of NO by NH₃ over Fe-Cu-OX/CNTs-TiO₂ composites at low temperature[J]. Appl Catal A:Gen, 2012,427-428:43-48. doi: 10.1016/j.apcata.2012.03.028
34. [34]
  TIAN W, YANG H S, FAN X Y, ZHANG X B. Catalytic reduction of NO_x with NH₃ over different-shaped MnO₂ at low temperature[J]. J Hazard Mater, 2011,188(1/3):105-109.
35. [35]
  ZHANG Y, WANG J J, LI X C, LIU X H, XIA Y J, HU B C, LU G Z. Direct conversion of biomass-derived carbohydrates to 5-hydroxymethylfurural over water-tolerant niobium-based catalysts[J]. Fuel, 2015,139(1):301-307.
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