Skip to main content
SpringerLink
Log in

The synthesis of Fe-containing ionic liquid and its catalytic performance for the dehydration of fructose

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

Four Fe-containing ionic liquids (ILs) were synthesized by coupling of conventional imidazole ionic liquids [Cxmim]Cl (x = 4, 8, 12, 16) with FeCl3 and were characterized by FT-IR, Raman, ESI–MS and TG. All of the Fe-containing ILs were applied to the conversion of fructose into 5-hydroxymethylfurfural (HMF) in 1-butyl-3-methylimidazolium chloride ([Bmim]Cl) subsequently and the result showed that [C16mim]FeCl4 exhibited excellent catalytic performance. Then the different reaction parameters with [C16mim]FeCl4 as catalyst were studied in detail. A 92.8% yield of HMF was obtained with 0.03 g [C16mim]FeCl4 and 0.1 g fructose in 1.0050 g [Bmim]Cl at 80 °C for 40 min in fructose/[Bmim]Cl solution.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  • Alexander MV, Khandekar AC, Samant SD (2004) Sulfonylation reactions of aromatics using FeCl3-based ionic liquids. J Mol Catal A 223:75–83. doi:10.1016/j.molcata.2003.10.066

    Article  CAS  Google Scholar 

  • Bahr JL, Yang JP, Kosynkin DV, Bronikowski MJ, Smalley RE, Tour JM (2001) Functionalization of carbon nanotubes by electrochemical reduction of aryl diazonium salts: a bucky paper electrode. J Am Chem Soc 123:6536–6542. doi:10.1021/Ja010462s

    Article  CAS  Google Scholar 

  • Bica K, Gaertner P (2006) An iron-containing ionic liquid as recyclable catalyst for aryl grignard cross-coupling of alkyl halides. Org Lett 8:733–735. doi:10.1021/ol052965z

    Article  CAS  Google Scholar 

  • Cao Q, Guo XC, Yao SX, Guan J, Wang XY, Mu XD, Zhang DK (2011) Conversion of hexose into 5-hydroxymethylfurfural in imidazolium ionic liquids with and without a catalyst. Carbohydr Res 346:956–959. doi:10.1016/j.carres.2011.03.015

    Article  CAS  Google Scholar 

  • Chheda JN, Dumesic JA (2007) An overview of dehydration, aldol-condensation and hydrogenation processes for production of liquid alkanes from biomass-derived carbohydrates. Catal Today 123:59–70. doi:10.1016/j.cattod.2006.12.006

    Article  CAS  Google Scholar 

  • Choudhary V, Burnett RI, Vlachos DG, Sandler SI (2012) Dehydration of glucose to 5-(hydroxymethyl)furfural and anhydroglucose: thermodynamic insights. J Phys Chem C 116:5116–5120. doi:10.1021/jp2113895

    Article  CAS  Google Scholar 

  • Csihony S, Mehdi H, Horvath IT (2001) In situ infrared spectroscopic studies of the Friedel-Crafts acetylation of benzene in ionic liquids using AlCl3 and FeCl3. Green Chem 3:307–309. doi:10.1039/B107515m

    Article  CAS  Google Scholar 

  • De S, Dutta S, Saha B (2011) Microwave assisted conversion of carbohydrates and biopolymers to 5-hydroxymethylfurfural with aluminium chloride catalyst in water. Green Chem 13:2859–2868. doi:10.1039/C1GC15550D

    Article  CAS  Google Scholar 

  • Del Sesto RE, McCleskey T, Burrell AK, Baker GA, Thompson JD, Scott BL, Wilkes JS, Williams P (2008) Structure and magnetic behavior of transition metal based ionic liquids. Chem Commun 4:447–449. doi:10.1039/b711189d

    Article  Google Scholar 

  • Dornath P, Fan W (2014) Dehydration of fructose into furans over zeolite catalyst using carbon black as adsorbent. Microporous Mesoporous Mater 191:10–17. doi:10.1016/j.micromeso.2014.02.031

    Article  CAS  Google Scholar 

  • Dutta S, De S, Saha B (2012) A brief summary of the synthesis of polyester building-block chemicals and biofuels from 5-hydroxymethylfurfural. ChemPlusChem 77:259–272. doi:10.1002/cplu.201100035

    Article  CAS  Google Scholar 

  • Gallezot P (2012) Conversion of biomass to selected chemical products. Chem Soc Rev 41:1538–1558. doi:10.1039/c1cs15147a

    Article  CAS  Google Scholar 

  • Guo XC, Cao Q, Jiang YJ, Guan J, Wang XY, Mu XD (2012) Selective dehydration of fructose to 5-hydroxymethylfurfural catalyzed by mesoporous SBA-15-SO3H in ionic liquid BmimCl. Carbohydr Res 351:35–41. doi:10.1016/j.carres.2012.01.003

    Article  CAS  Google Scholar 

  • Harmer MA, Junk CP, Rostovtsev VV, Marshall WJ, Grieco LM, Vickery J, Miller R, Work S (2009) Catalytic reactions using superacids in new types of ionic liquids. Green Chem 11:517–525. doi:10.1039/b818788f

    Article  CAS  Google Scholar 

  • HoangTran P, Do NB, NgocLe T (2014) Improvement of the Friedel-Crafts benzoylation by using bismuth trifluoromethanesulfonate in 1-butyl-3-methylimidazolium trifluoromethanesulfonate ionic liquid under microwave irradiation. Tetrahedron Lett 55:205–208. doi:10.1016/j.tetlet.2013.10.155

    Article  CAS  Google Scholar 

  • Kim JY, Kim JT, Song EA, Min YK, Hamaguchi H (2008) Polypyrrole nanostructures self-assembled in magnetic ionic liquid as a template. Macromolecules 41:2886–2889. doi:10.1021/ma01333k

    Article  CAS  Google Scholar 

  • Lee SH, Ha SH, You CY, Koo YM (2007) Recovery of magnetic ionic liquid [bmim]FeCl4 using electromagnet. Korean J Chem Eng 24:436–437. doi:10.1007/s11814-007-0075-x

    Article  CAS  Google Scholar 

  • Li Y, Liu H, Song CH, Gu XM, Li HM, Zhu WS, Yin S, Han CR (2013) The dehydration of fructose to 5-hydroxymethylfurfural efficiently catalyzed by acidic ion-exchange resin in ionic liquid. Bioresour Technol 133:347–353. doi:10.1016/j.biortech.2013.01.038

    Article  CAS  Google Scholar 

  • Liu H, Hua C, Song CH, Dai SF, Wang HW, Zhu WS, Li HM (2015) Commercially available ammonium salt-catalyzed efficient dehydration of fructose to 5-hydroxymethylfurfural in ionic liquid. Inorg Chim Acta 428:32–36. doi:10.1016/j.ica.2015.01.016

    Article  CAS  Google Scholar 

  • Martinez-Magadan JM, Oviedo-Roa R, Garcia P, Martinez-Palou R (2012) DFT study of the interaction between ethanethiol and Fe-containing ionic liquids for desulfuration of natural gasoline. Fuel Process Technol 97:24–29. doi:10.1016/j.fuproc.2012.01.007

    Article  CAS  Google Scholar 

  • Melero JA, Iglesias J, Garcia A (2012) Biomass as renewable feedstock in standard refinery units. Feasibility, opportunities and challenges. Energy Environ Sci 5:7393–7420. doi:10.1039/c2ee21231e

    Article  CAS  Google Scholar 

  • Nguyen MD, Nguyen LV, Jeon EH, Kim JH, Cheong M, Kim HS, Lee JS (2008) Fe-containing ionic liquids as catalysts for the dimerization of bicyclo[2.2.1]hepta-2,5-diene. J Catal 258:5–13. doi:10.1016/j.jcat.2008.05.008

    Article  CAS  Google Scholar 

  • Pei XW, Yan YH, Yan LY, Yang P, Wang JL, Xu R, Chan-Park MB (2010) A magnetically responsive material of single-walled carbon nanotubes functionalized with magnetic ionic liquid. Carbon 48:2501–2505. doi:10.1016/j.carbon.2010.03.023

    Article  CAS  Google Scholar 

  • Qi XH, Watanabe M, Aida TM, Smith RL (2009) Efficient process for conversion of fructose to 5-hydroxymethylfurfural with ionic liquids. Green Chem 11:1327–1331. doi:10.1039/b905975j

    Article  CAS  Google Scholar 

  • Qi XH, Guo HX, Li LY (2011) Efficient conversion of fructose to 5-hydroxymethylfurfural catalyzed by sulfated zirconia in ionic liquids. Ind Eng Chem Res 50:7985–7989. doi:10.1021/ie200488k

    Article  CAS  Google Scholar 

  • Rosatella AA, Simeonov SP, Frade RFM, Afonso CAM (2011) 5-Hydroxymethylfurfural (HMF) as a building block platform: biological properties, synthesis and synthetic applications. Green Chem 13:754–793. doi:10.1039/c0gc00401d

    Article  CAS  Google Scholar 

  • Shang SM, Li L, Yang XM, Zheng L (2009) Synthesis and characterization of poly(3-methyl thiophene) nanospheres in magnetic ionic liquid. J Colloid Interface Sci 333:415–418. doi:10.1016/j.jcis.2009.01.021

    Article  CAS  Google Scholar 

  • Sun Y, Liu P, Liu Z (2016) Catalytic conversion of carbohydrates to 5-hydroxymethylfurfural from the waste liquid of acid hydrolysis NCC. Carbohydr Polym 142:177–182. doi:10.1016/j.carbpol.2016.01.053

    Article  CAS  Google Scholar 

  • Takagaki A, Nishimura S, Ebitani K (2012) Catalytic transformations of biomass-derived materials into value-added chemicals. Catal Surv Asia 6:164–182. doi:10.1007/s10563-012-9142-3

    Article  Google Scholar 

  • Van Putten RJ, van der Waal JC, de Jong E, Rasrendra CB, Heeres HJ, de Vries JG (2013) Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chem Rev 113:1499–1597. doi:10.1021/cr300182k

    Article  Google Scholar 

  • Wang H, Yan RY, Li ZX, Zhang XP, Zhang SJ (2010) Fe-containing magnetic ionic liquid as an effective catalyst for the glycolysis of poly(ethylene terephthalate). Catal Commun 11:763–767. doi:10.1016/j.catcom.2010.02.011

    Article  CAS  Google Scholar 

  • Wang JL, Yao HW, Nie Y, Bai L, Zhang XP, Li JW (2012) Application of iron-containing magnetic ionic liquids in extraction process of coal direct liquefaction residues. Ind Eng Chem Res 51:3776–3782. doi:10.1021/ie202940k

    Article  CAS  Google Scholar 

  • Warnke Z, Styczen E, Wyrzykowski D, Sikorski A, Klak J, Mrozinski J (2010) Structural and physico-chemical characteristics of tetraethylammonium tetrachloridoferrate(III). Struct Chem 21:285–289. doi:10.1007/s11224-009-9537-6

    Article  CAS  Google Scholar 

  • Wei YY, Zhao Y, Li LA, Yang XM, Yu XH, Yan GP (2010) Magnetic ionic liquid-assisted synthesis of polypyrrole/AgCl nanocomposites. Polym Adv Technol 21:742–745. doi:10.1002/pat.1682

    Article  CAS  Google Scholar 

  • Xia Y, Yan CH, Li Z, Gao HH, Sun HM, Shen Q, Zhang Y (2012) Synthesis, structure of iron(III)-containing imidazolium salts and their catalytic activity in the alkylation of aryl Grignard reagents. Chin Sci Bull 58:493–499. doi:10.1007/s11434-012-5513-4

    Article  Google Scholar 

  • Yang FL, Liu QS, Yue M, Bai XF, Du YG (2011) Tantalum compounds as heterogeneous catalysts for saccharide dehydration to 5-hydroxymethylfurfural. Chem Commun 47:4469–4471. doi:10.1039/c0cc05138a

    Article  CAS  Google Scholar 

  • Yao AN, Chu TW (2013) Fe-containing ionic liquids as effective and recoverable oxidants for dissolution of UO2 in the presence of imidazolium chlorides. Dalton Trans 42:8413–8419. doi:10.1039/c3dt32832e

    Article  CAS  Google Scholar 

  • Zhao HB, Holladay JE, Brown H, Zhang ZC (2007) Metal chlorides in ionic liquid solvents convert sugars to 5-hydroxymethylfurfural. Science 316:1597–1600. doi:10.1126/science.1141199

    Article  CAS  Google Scholar 

  • Zhao J, Zhou CM, He C, Dai YH, Jia XL, Yang YH (2016) Efficient dehydration of fructose to 5-hydroxymethylfurfural over sulfonated carbon sphere solid acid catalysts. Catal Today 264:123–130. doi:10.1016/j.cattod.2015.07.005

    Article  CAS  Google Scholar 

  • Zhou XM, Zhang ZH, Liu B, Zhou Q, Wang SG, Deng KJ (2014) Catalytic conversion of fructose into furans using FeCl3 as catalyst. J Ind Eng Chem 20:644–649. doi:10.1016/j.jiec.2013.05.028

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors thank the financial support for this study by the National Natural Science Foundation of China (21106057, 21406092, 21506080, 31170672), and Advanced Talents of Jiangsu University (10JDG143), China Postdoctoral Science Foundation (2014T70489, 2013M541621, 1302152C).

Author information

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, People’s Republic of China

    Hui Liu, Yue Wang, Wanxia Ma, Hongwei Wang, Deping Wang & Huaming Li

  2. Institute for Energy Research, Jiangsu University, Zhenjiang, 212013, People’s Republic of China

    Wei Jiang & Ming Zhang

  3. School of Food and Biological Engineering, Jiangsu University, Zhenjiang, 212013, People’s Republic of China

    Cunshan Zhou

Authors
  1. Hui Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yue Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Wanxia Ma
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hongwei Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Deping Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Wei Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Ming Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Cunshan Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Huaming Li
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Hui Liu or Huaming Li.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liu, H., Wang, Y., Ma, W. et al. The synthesis of Fe-containing ionic liquid and its catalytic performance for the dehydration of fructose. Chem. Pap. 71, 1541–1549 (2017). https://doi.org/10.1007/s11696-017-0148-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11696-017-0148-1

Keywords

Search

Navigation