Skip to main content
SpringerLink
Log in

Tetraalkylammonium Ionic Liquids as Dual Solvents–Catalysts for Direct Synthesis of Sugar Fatty Acid Esters

  • Original Article
  • Published:
Journal of Surfactants and Detergents

Abstract

As nonionic surfactants derived from naturally renewable resources such as sugars and fatty acids, sugar fatty acid esters have been widely utilized in food, cosmetic and pharmaceutical industries. Our present study has demonstrated that the inexpensive and halogen-free tetraalkylammonium salts (e.g., [Bu4N][Ac], [Et4N][Ac] and [Me4N][Ac]) can act as dual solvents–catalysts for regioselective acylation to produce glucose laurate. This non-enzymatic synthesis can proceed under mild conditions with high specificity, and the conversions obtained were superior to that when an enzyme catalyst (lipase, EC 3.1.1.3) was added. A higher yield was obtained in the ammonium salt with a longer alkyl chain on the cation, while no product was obtained in [Bu4N][HSO4] and [Bu4P][Ac]. A reaction mechanism has been proposed, which is supported by phase-transfer catalysis and law of matching water affinity.

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

Fig. 1
Fig. 2
Scheme 1
Fig. 3
Fig. 4
Fig. 5
Scheme 2

Similar content being viewed by others

References

  1. Kobayashi T (2011) Lipase-catalyzed syntheses of sugar esters in non-aqueous media. Biotechnol Lett 33:1911–1919

    Article  CAS  Google Scholar 

  2. Gumel AM, Annuar MSM, Heidelberg T, Chisti Y (2011) Lipase mediated synthesis of sugar fatty acid esters. Process Biochem 46:2079–2090

    Article  CAS  Google Scholar 

  3. Plat T, Linhardt RJ (2001) Syntheses and applications of sucrose-based esters. J Surfactants Deterg 4:415–421

    Article  Google Scholar 

  4. Yang Z, Pan W (2005) Ionic liquids: green solvents for nonaqueous biocatalysis. Enzyme Microb Technol 37:19–28

    Article  CAS  Google Scholar 

  5. Domínguez de María P (2012) Ionic liquids in biotransformations and organocatalysis: solvents and beyond. Wiley, Hoboken

    Book  Google Scholar 

  6. Nowicki J, Muszyñski M (2014) Ionic liquids as catalysts and reaction media in oleochemical raw materials processing: a review. Curr Org Chem 18:2797–2807

    Article  CAS  Google Scholar 

  7. Forsyth SA, MacFarlane DR, Thomson RJ, von Itzstein M (2002) Rapid, clean, and mild O-acetylation of alcohols and carbohydrates in an ionic liquid. Chem Commun 714–715

  8. Cole AC, Jensen JL, Ntai I, Tran KLT, Weaver KJ, Forbes DC, Davis JH (2002) Novel Brønsted acidic ionic liquids and their use as dual solvent–catalysts. J Am Chem Soc 124:5962–5963

    Article  CAS  Google Scholar 

  9. Zhu H-P, Yang F, Tang J, He M-Y (2003) Brønsted acidic ionic liquid 1-methylimidazolium tetrafluoroborate: a green catalyst and recyclable medium for esterification. Green Chem 5:38–39

    Article  CAS  Google Scholar 

  10. Gui J, Cong X, Liu D, Zhang X, Hu Z, Sun Z (2004) Novel Brønsted acidic ionic liquid as efficient and reusable catalyst system for esterification. Catal Commun 5:473–477

    Article  CAS  Google Scholar 

  11. Fang D, Zhou X-L, Ye Z-W, Liu Z-L (2006) Brønsted acidic ionic liquids and their use as dual solvent–catalysts for Fischer esterifications. Ind Eng Chem Res 45:7982–7984

    Article  CAS  Google Scholar 

  12. Li H, Yu S, Liu F, Xie C, Li L (2007) Synthesis of dioctyl phthalate using acid functionalized ionic liquid as catalyst. Catal Commun 8:1759–1762

    Article  CAS  Google Scholar 

  13. Zhang H, Xu F, Zhou X, Zhang G, Wang C (2007) A Brønsted acidic ionic liquid as an efficient and reusable catalyst system for esterification. Green Chem 9:1208–1211

    Article  CAS  Google Scholar 

  14. Xie C, Li H, Li L, Yu S, Liu F (2008) Synthesis of plasticizer ester using acid-functionalized ionic liquid as catalyst. J Hazard Mater 151:847–850

    Article  CAS  Google Scholar 

  15. Zhang L, Xian M, He Y, Li L, Yang J, Yu S, Xu X (2009) A Brønsted acidic ionic liquid as an efficient and environmentally benign catalyst for biodiesel synthesis from free fatty acids and alcohols. Bioresour Technol 100:4368–4373

    Article  CAS  Google Scholar 

  16. Junming XU, Jiang J, Zuo Z, Li J (2010) Synthesis of tributyl citrate using acid ionic liquid as catalyst. Process Saf Environ Prot 88:28–30

    Article  Google Scholar 

  17. Yang Y, He W, Jia C, Ma Y, Zhang X, Feng B (2012) Efficient synthesis of phytosteryl esters using the Lewis acidic ionic liquid. J Mol Catal A Chem 357:39–43

    Article  CAS  Google Scholar 

  18. Lin X-S, Cai Y-Z, Halling PJ, Yang Z (2015) Impacts of ionic liquids on enzymatic synthesis of glucose laurate and optimization with superior productivity by response surface methodology. Process Biochem 50:1852–1858

    Article  CAS  Google Scholar 

  19. Reichardt C (2005) Polarity of ionic liquids determined empirically by means of solvatochromic pyridinium N-phenolate betaine dyes. Green Chem 7:339–351

    Article  CAS  Google Scholar 

  20. Laane C, Boeren S, Vos K, Veeger C (1987) Rules for optimization of biocatalysis in organic solvents. Biotechnol Bioeng 30:81–87

    Article  CAS  Google Scholar 

  21. Benfenati E, Gini G, Piclin N, Roncaglioni A, Varí MR (2003) Predicting log P of pesticides using different software. Chemosphere 53:1155–1164

    Article  CAS  Google Scholar 

  22. Miller GL (1959) Use of dinitrosalicylic acid reagent for determination of reducing sugar. Anal Chem 31:426–428

    Article  CAS  Google Scholar 

  23. Collins KD (2004) Ions from the Hofmeister series and osmolytes: effects on proteins in solution and in the crystallization process. Methods 34:300–311

    Article  CAS  Google Scholar 

  24. Starks CM (1971) Phase-transfer catalysis. I. Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts. J Am Chem Soc 93:195–199

    Article  CAS  Google Scholar 

  25. Ooi T, Maruoka K (2007) Recent advances in asymmetric phase-transfer catalysis. Angew Chem Int Ed 46:4222–4266

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are grateful to the National Natural Science Foundation of China for its financial support (No. 21276159).

Author information

Authors and Affiliations

  1. College of Life Sciences, Shenzhen University, Shenzhen, 518060, Guangdong, China

    Xiao-Sheng Lin, Kai-Hua Zhao, Tao-Xiang Yang & Zhen Yang

  2. School of Pharmaceutical Sciences, Sun Yat-Sen University, Guangzhou, 510006, Guangdong, China

    Yong Zou

  3. Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, UK

    Peter Halling

Authors
  1. Xiao-Sheng Lin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yong Zou
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kai-Hua Zhao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tao-Xiang Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Peter Halling
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Zhen Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zhen Yang.

Electronic supplementary material

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lin, XS., Zou, Y., Zhao, KH. et al. Tetraalkylammonium Ionic Liquids as Dual Solvents–Catalysts for Direct Synthesis of Sugar Fatty Acid Esters. J Surfact Deterg 19, 511–517 (2016). https://doi.org/10.1007/s11743-016-1798-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-016-1798-7

Keywords

Search

Navigation