Skip to main content
Log in

Acidic ionic liquid polymers: poly(bis-imidazolium-p-phenylenesulfonic acid) and applications as catalysts in the preparation of 1-amidoalkyl-2-naphthols

  • SHORT COMMUNICATION
  • Published:
Journal of Polymer Research Aims and scope Submit manuscript

Abstract

A new class of polymeric acidic ionic liquids with imidazolium hydrogen sulfate and p-phenylene sulfonic acid units built into the main polymer chain were prepared by a simple two step method in 87–89% yield. These new polymers were characterized by elemental analysis, 1H, 13C NMR, FT-IR, TGA and GPC. The catalytic activity of sulfonic acid group functionalized ionic liquid polymers was demonstrated through the synthesis of 1-amidoalkyl-2-naphthols in 78–90% yield by condensation of 2-naphthol, benzaldehyde and amides without a solvent at 100 °C.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

References

  1. Wu J, Gao Y, Zhang W, Tan Y, Tang A, Men Y, Tang B (2014) Deep oxidation desulfurization with a new imidazole-type acidic ionic liquid polymer. RSC Adv 4(102):58800–58804

    Article  CAS  Google Scholar 

  2. Hsieh YN, Ho WY, Horng RS, Huang PC, Hsu CY, Huang HH, Kuei CH (2007) Study of anion effects on separation phenomenon for the vinyloctylimidazolium based ionic liquid polymer stationary phases in GC. Chromatographia 66(7–8):607–611

    Article  CAS  Google Scholar 

  3. Ricks-Laskoski HL, Snow AW (2006) Synthesis and electric field actuation of an ionic liquid polymer. J Am Chem Soc 128(38):12402–12403

    Article  CAS  Google Scholar 

  4. Hu X, Huang J, Zhang W, Li M, Tao C, Li G (2008) Photonic ionic liquids polymer for naked-eye detection of anions. Adv Mater 20(21):4074–4078

    Article  CAS  Google Scholar 

  5. Sato T, Marukane S, Narutomi T, Akao T (2007) High rate performance of a lithium polymer battery using a novel ionic liquid polymer composite. J Power Sources 164(1):390–396

    Article  CAS  Google Scholar 

  6. Zhang Y, Chen X, Lan J, You J, Chen L (2009) Synthesis and biological applications of imidazolium-based polymerized ionic liquid as a gene delivery vector. Chem Biol Drug Des 74(3):282–288

    Article  CAS  Google Scholar 

  7. Bara JE, Lessmann S, Gabriel CJ, Hatakeyama ES, Noble RD, Gin DL (2007) Synthesis and performance of polymerizable room-temperature ionic liquids as gas separation membranes. Ind Eng Chem Res 46(16):5397–5404

    Article  CAS  Google Scholar 

  8. Chen H, Choi JH, Cruz DSDL, Winey KI, Elabd YA (2009) Polymerized ionic liquids: the effect of random copolymer composition on ion conduction. Macromolecules 42(13):4809–4816

    Article  CAS  Google Scholar 

  9. Chen H, Elabd YA (2009) Polymerized ionic liquids: solution properties and electrospinning. Macromolecules 42(9):3368–3373

    Article  CAS  Google Scholar 

  10. Fang Y, Xiang W, Zhou X, Lin Y, Fang S (2011) High-performance novel acidic ionic liquid polymer/ionic liquid composite polymer electrolyte for dye-sensitized solar cells. Electrochem Commun 13(1):60–63

    Article  CAS  Google Scholar 

  11. Freitas FS, Freitas JND, Ito BI, Paoli MAD, Nogueira AF (2009) Electrochemical and structural characterization of polymer gel electrolytes based on a PEO copolymer and an imidazolium-based ionic liquid for dye-sensitized solar cells. ACS Appl Mater Interfaces 1(12):2870–2877

    Article  CAS  Google Scholar 

  12. Amarasekara AS (2016) Acidic Ionic Liquids. Chem Rev 116(10):6133–6183

    Article  CAS  Google Scholar 

  13. Wang J, Zong Y, Fu R, Niu Y, Yue G, Quan Z, Wang X, Pan Y (2014) Poly(4-vinylpyridine) supported acidic ionic liquid: a novel solid catalyst for the efficient synthesis of 2,3-dihydroquinazolin-4(1H)-ones under ultrasonic irradiation. Ultrason Sonochem 21(1):29–34

    Article  CAS  Google Scholar 

  14. Liu F, Kamat RK, Noshadi I, Peck D, Parnas RS, Zheng A, Qi C, Lin Y (2013) Depolymerization of crystalline cellulose catalyzed by acidic ionic liquids grafted onto sponge-like nanoporous polymers. Chem Commun 49(76):8456–8458

    Article  CAS  Google Scholar 

  15. Yasuda T, Watanabe M (2013) Protic ionic liquids: Fuel cell applications. MRS Bull 38(7):560–566

    Article  CAS  Google Scholar 

  16. Liang X (2013) Novel acidic ionic liquid polymer for biodiesel synthesis from waste oils. Appl Catal A Gen 455:206–210

    Article  CAS  Google Scholar 

  17. Liang X, Xiao H, Qi C (2013) Efficient procedure for biodiesel synthesis from waste oils using novel solid acidic ionic liquid polymer as catalysts. Fuel Process Technol 110:109–113

    Article  CAS  Google Scholar 

  18. Amarasekara AS, Owereh OS (2009) Hydrolysis and decomposition of cellulose in bron̈sted acidic ionic liquids under mild conditions. Ind Eng Chem Res 48(22):10152–10155

    Article  CAS  Google Scholar 

  19. Amarasekara AS, Owereh OS (2010) Synthesis of a sulfonic acid functionalized acidic ionic liquid modified silica catalyst and applications in the hydrolysis of cellulose. Catal Commun 11(13):1072–1075

    Article  CAS  Google Scholar 

  20. Amarasekara AS, Wiredu B (2011) Degradation of cellulose in dilute aqueous solutions of acidic ionic liquid 1-(1-propylsulfonic)-3-methylimidazolium chloride, and p-toluenesulfonic acid at moderate temperatures and pressures. Ind Eng Chem Res 50(21):12276–12280

    Article  CAS  Google Scholar 

  21. Amarasekara AS, Shanbhag P (2013) Degradation of untreated Switchgrass biomass into reducing sugars in 1-(Alkylsulfonic)-3-methylimidazolium Brönsted acidic ionic liquid medium under mild conditions. Bioenerg Res 6(2):719–724

    Article  CAS  Google Scholar 

  22. Amarasekara AS, Wiredu B (2014) Single reactor conversion of corn Stover biomass to C5–C20 furanic biocrude oil using sulfonic acid functionalized Brönsted acidic ionic liquid catalysts. Biomass Conv Bioref 4(2):149–155

  23. Amarasekara AS, Owereh OS (2011) Thermal properties of sulfonic acid group functionalized Brönsted acidic ionic liquids. J Therm Anal Calorim 103(3):1027–1030

    Article  CAS  Google Scholar 

  24. Amarasekara AS, Shanbhag P (2011) Synthesis and characterization of polymeric ionic liquid poly(imidazolium chloride-1,3-diylbutane-1,4-diyl). Polym Bull 67(4):623–629

    Article  CAS  Google Scholar 

  25. Amarasekara AS, Callis B, Wiredu B (2012) Synthesis and characterization of branched polymeric ionic liquids with imidazolium chloride segments. Polym Bull 68(4):901–908

    Article  CAS  Google Scholar 

  26. Ma JF, Yang J, Zheng GL, Li L, Zhang YM, Li FF, Liu JF (2004) Four new coordination polymers of Cu(II) with 1,1′-(1,4-butanediyl) bis(imidazole). Polyhedron 23(4):553–559

    Article  CAS  Google Scholar 

  27. Amarasekara AS, Razzaq A, Caballero R, Wiredu B (2014) Sol-gel synthesis, characterization and water vapor adsorption properties of 1,1′-(1,6-hexanediyl)-bis(imidazolium)dichloride-silica hybrid material. J Sol-Gel Sci Technol 69:345–350

  28. Kotadia DA, Soni SS (2012) Silica gel supported –SO3H functionalised benzimidazolium based ionic liquid as a mild and effective catalyst for rapid synthesis of 1-amidoalkyl naphthols. J Mol Catal A Chem 353–354:44–49

    Article  Google Scholar 

  29. Shaterian HR, Mohammadnia M (2013) Nanocrystalline TiO2-HClO4 catalyzed three-component preparation of derivatives of 1-amidoalkyl-2-naphthol, 1-carbamato-alkyl-2- naphthol, 1-(α-aminoalkyl)-2-naphthol, and 12-aryl-8,9,10,12- tetrahydrobenzo[a]-xanthen-11-one. Res Chem Intermed 39(9):4221–4237

    Article  CAS  Google Scholar 

  30. Brennecke JFR, R.D; Seddon, K.R (2007) Ionic liquids IV; not just solvents any more. Oxford University press, USA

  31. Rogers RD, Voth GA (2007) Ionic Liquids. Acc Chem Res 40(11):1077–1078

    Article  CAS  Google Scholar 

  32. Rogers RD, Seddon KR (2003) Ionic liquids - solvents of the future? Science 302(5646):792–793

    Article  Google Scholar 

  33. Varma RS, Namboodiri VV (2001) Solvent-free preparation of ionic liquids using a household microwave oven. Pure Appl Chem 73(8):1309–1313

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank National Science Foundation grants CBET-0929970, CBET-1336469, HRD-1036593, and United States Department of Agriculture grant CBG-2010-38821-21569 for financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ananda S. Amarasekara.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Amarasekara, A.S., Nguyen, J. & Razzaq, A. Acidic ionic liquid polymers: poly(bis-imidazolium-p-phenylenesulfonic acid) and applications as catalysts in the preparation of 1-amidoalkyl-2-naphthols. J Polym Res 24, 52 (2017). https://doi.org/10.1007/s10965-017-1216-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10965-017-1216-5

Keywords

Navigation