Robust acidic pseudo-ionic liquid catalyst with self-separation ability for esterification and acetalization

  • Yingxia Shi
  • Xuezheng LiangEmail author
Original Paper


The novel acidic pseudo-ionic liquid catalyst with self-separation ability has been synthesized through the quaternization of triphenylphosphine and the acidification with silicotungstic acid. The pseudo-IL showed high activities for the esterification with average conversions over 90%. The pseudo-IL showed even higher activities for acetalization than traditional sulfuric acid. The homogeneous catalytic process benefited the mass transfer efficiency. The pseudo-IL separated from the reaction mixture automatically after reactions, which was superior to other IL catalysts. The high catalytic activities, easy reusability and high stability were the key properties of the novel catalyst, which hold great potential for green chemical processes.


Acidic pseudo-ionic liquid Self-separation Esterification Acetalization 



The work was supported by Public Welfare Project from Science and technology department of Zhejiang province no. 2017C31109 and National Undergraduate Training Program for Innovation and Entrepreneurship no. 201610349004.


  1. Chen G, Zhou Y, Long Z, Wang X, Li J, Wang J (2014) Mesoporous polyoxometalate-based ionic hybrid as a triphasic catalyst for oxidation of benzyl alcohol with H2O2 on water. ACS Appl Mater Interfaces 6:4438–4446. CrossRefGoogle Scholar
  2. Cole AC, Jensen JL, Ntai I, Tran KLT, Weaver KJ, Forbes DC et al (2002) Novel brønsted acidic ionic liquids and their use as dual solvent–catalysts. J Am Chem Soc 124:5962–5963. CrossRefGoogle Scholar
  3. Da Silveira Neto BA, Ebeling G, Goncalves RS, Gozzo FC, Eberlin MN, Dupont J (2004) Organoindate room temperature ionic liquid: synthesis, physicochemical properties and application. Synthesis. Google Scholar
  4. Dupont J, Souza RF, Suarez PAZ (2002) Ionic liquid (molten salt) phase organometallic catalysis. Chem Rev 102:3667–3692. CrossRefGoogle Scholar
  5. Greaves TL, Drummond CJ (2008) Protic ionic liquids: properties and applications. Chem Rev 108:206–237. CrossRefGoogle Scholar
  6. Isahak W, Ramli Z, Ismail M, Yarmo M (2014) Highly selective glycerol esterification over silicotungstic acid nanoparticles on ionic liquid catalyst. Ind Eng Chem Res 53:10285–10293. CrossRefGoogle Scholar
  7. Leng Y, Wang J, Zhu DR, Ren XQ, Ge HQ, Shen L (2009) Heteropolyanion-based ionic liquids: reaction-induced self-separated catalysts for esterification. Angew Chem Int Ed 48:168–171. CrossRefGoogle Scholar
  8. Li G, Ding Y, Wang J, Wang X, Suo J (2007) New progress of Keggin and Wells–Dawson type polyoxometalates catalyze acid and oxidation reactions. J Mol Catal A Chem 262:67–76. CrossRefGoogle Scholar
  9. Li H, Qiao Y, Hua L, Hou Z, Feng B, Pan Z, Hu Y, Wang X, Zhao X, Yu Y (2010) Imidazolium polyoxometalate: an ionic liquid catalyst for esterification and oxidative esterification. ChemCatChem 2:1165–1170. CrossRefGoogle Scholar
  10. Liang XZ (2013a) Synthesis of biodiesel from waste oil under mild conditions using novel acidic ionic liquid immobilization on poly divinylbenzene. Energy 63:103–108. CrossRefGoogle Scholar
  11. Liang XZ (2013b) Novel efficient procedure for biodiesel synthesis from waste oils using solid acidic ionic liquid polymer as the catalyst. Ind Eng Chem Res 52(2013):6894–6900. CrossRefGoogle Scholar
  12. Liang XZ (2013c) Novel acidic ionic liquid polymer for biodiesel synthesis from waste oils. Appl Catal A Gen 455:206–210. CrossRefGoogle Scholar
  13. Liang XZ, Xiao HQ, Qi CZ (2013) Efficient procedure for biodiesel synthesis from waste oils using novel solid acidic ionic liquid polymer as catalysts. Fuel Process Technol 110:109–113. CrossRefGoogle Scholar
  14. Men Y, Li XH, Antonietti M, Yuan J (2012) Poly(tetrabutylphosphonium 4-styrenesulfonate): a poly(ionic liquid) stabilizer for graphene being multi-responsive. Polym Chem 3:871–873. CrossRefGoogle Scholar
  15. Miao J, Wan H, Shao Y, Guan G, Xu B (2011) Acetalization of carbonyl compounds catalyzed by acidic ionic liquid immobilized on silica gel. J Mol Catal A Chem 348:77–82. CrossRefGoogle Scholar
  16. Pauline P, Clarence C, Jean M, Lucy P, Francisco G, Frederic L, Evelina C (2010) Synthesis of a new hydrophilic poly(ethylene glycol)-ionic liquid and its application in peptide synthesis. Chem Commun 46:8842–8843. CrossRefGoogle Scholar
  17. Rashinkar G, Kamble S, Kumbhar A, Salunkhe R (2011) An expeditious synthesis of homoallylic alcohols using Brønsted acidic supported ionic liquid phase catalyst with pendant ferrocenyl group. Catal Commun 12:1442–1447. CrossRefGoogle Scholar
  18. Sheldon R (2001) Catalytic reactions in ionic liquids. Chem Commun. Google Scholar
  19. Sugimura R, Qiao K, Tomida D, Yokoyama C (2007) Immobilization of acidic ionic liquids by copolymerization with styrene and their catalytic use for acetal formation. Catal Commun 8:770–772. CrossRefGoogle Scholar
  20. Wasserscheid P, Keim W (2000) Ionic liquids-new “solutions” for transition metal catalysis. Angew Chem Int Ed 39:3772–3789.;2-5 CrossRefGoogle Scholar
  21. Zhao D, Wu M, Kou Y, Min E (2002) Ionic liquids: applications in catalysis. Catal Today 74:157–189. CrossRefGoogle Scholar

Copyright information

© Institute of Chemistry, Slovak Academy of Sciences 2019

Authors and Affiliations

  1. 1.School of Chemistry and Chemical EngineeringShaoxing UniversityShaoxingChina

Personalised recommendations