Skip to main content
SpringerLink
Log in

Thermal properties of sulfonic acid group functionalized Brönsted acidic ionic liquids

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

Abstract

Thermal decomposition onset temperatures have been measured for a total of 24 methylimidazolium, triethanolammonium, and pyridinium type sulfonic acid groups functionalized Brönsted acidic ionic liquids with Cl−, Br−, SO4 2−, PO4 3−, BF4 − , CH3CO2 −, and CH3SO3 − anions, using thermogravimetric analysis. Thermal stabilities of these sulfonic acid group functionalized ionic liquids decreases in the order, methylimidazolium > triethanolammonium > pyridinium. The methylimidazolium, pyridinium, and triethanolammonium ionic liquids investigated showed decomposition onset temperatures (air) in the 213–353, 167–240, and 230–307 °C ranges, respectively. Additionally, the decomposition temperatures of these ionic liquids are highly dependent on the nature of the anion.

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

References

  1. Wasserscheid P, Welton T. Ionic liquids in synthesis. Weinheim: Wiley-VCH Verlag GmbH; 2008.

    Google Scholar 

  2. Welton T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev. 1999;99:2071–83.

    Article  CAS  Google Scholar 

  3. Lee SG. Functionalized imidazolium salts for task-specific ionic liquids and their applications. Chem Commun. 2006;10:1049–63.

    Article  Google Scholar 

  4. Plechkova NV, Seddon KR. Applications of ionic liquids in the chemical industry. Chem Soc Rev. 2008;37:123–50.

    Article  CAS  Google Scholar 

  5. Zhao H, Malhotra SV. Applications of ionic liquids in organic synthesis. Aldrichim Acta. 2002;35:75–83.

    Article  CAS  Google Scholar 

  6. Huddleston JG, Visser AE, Reichert WM, Willauer HD, Broker GA, Rogers RD. Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chem. 2001;3:156–64.

    Article  CAS  Google Scholar 

  7. Kamavaram V, Reddy RG. Thermal stabilities of di-alkylimidazolium chloride ionic liquids. Int J Therm Sci. 2008;47:773–7.

    Article  CAS  Google Scholar 

  8. Arellano IHJ, Guarino JG, Paredes FU, Arco SD. Thermal stability and moisture uptake of 1-alkyl-3-methylimidazolium bromide. J Therm Anal Calorim. 2010. doi:10.1007/s10973-010-0992-5.

  9. Ngo HL, LeCompte K, Hargens L, McEwen AB. Thermal properties of imidazolium ionic liquids. Thermochim Acta. 2000;357–358:97–102.

    Article  Google Scholar 

  10. Kosmulski M, Gustafsson J, Rosenholm JB. Thermal stability of low temperature ionic liquids revisited. Thermochim Acta. 2004;412:47–53.

    Article  CAS  Google Scholar 

  11. Del Sesto RE, McCleskey TM, Macomber C, Ott KC, Koppisch AT, Baker GA, Burrell AK. Limited thermal stability of imidazolium and pyrrolidinium ionic liquids. Thermochim Acta. 2009;491:118–20.

    Article  CAS  Google Scholar 

  12. Davis JH. Task-specific ionic liquids. Chem Lett. 2004;33:1072–7.

    Article  CAS  Google Scholar 

  13. Fei ZF, Geldbach TJ, Zhao DB, Dyson PJ. From dysfunction to bis-function: on the design and applications of functionalised ionic liquids. Chem Eur J. 2006;12:2122–30.

    Article  CAS  Google Scholar 

  14. Li X, Zhao D, Fei Z, Wang L. Applications of functionalized ionic liquids. Sci China Ser B. 2006;49:385–401.

    Article  CAS  Google Scholar 

  15. Jiang D, Wang YY, Tu M, Dai LY. Esterification of acetonitrile with alcohols in novel Brönsted acidic ionic liquids. React Kinet Catal Lett. 2008;95:265–71.

    Article  CAS  Google Scholar 

  16. Zhao Y, Long J, Deng F, Liu X, Li Z, Xia C, Peng J. Catalytic amounts of Brønsted acidic ionic liquids promoted esterification: study of acidity–activity relationship. Catal Commun. 2009;10:732–6.

    Article  CAS  Google Scholar 

  17. Qiao K, Yokoyama C. Novel acidic ionic liquids catalytic systems for Friedel-crafts alkylation of aromatic compounds with alkenes. Chem Lett. 2004;33:472–3.

    Article  CAS  Google Scholar 

  18. Qiao K, Yokoyama C. Nitration of aromatic compounds with nitric acid catalyzed by ionic liquids. Chem Lett. 2004;33:808–9.

    Article  CAS  Google Scholar 

  19. Qiao K, Deng Y, Yokoyama C, Sato H, Yamashina M. Preparation of ε-caprolactam via Beckmann rearrangement of cyclohexanone oxime: a mild and recyclable process. Chem Lett. 2004;33:1350–4.

    Article  CAS  Google Scholar 

  20. Gu Y, Shi F, Deng Y. SO3H-functionalized ionic liquid as efficient, green and reusable acidic catalyst system for oligomerization of olefins. Catal Commun. 2003;4:597–601.

    Article  CAS  Google Scholar 

  21. Amarasekara AS, Owereh OS. Hydrolysis and decomposition of cellulose in Brönsted acidic ionic liquids under mild conditions. Ind Eng Chem Res. 2009;48:10152–5.

    Article  CAS  Google Scholar 

  22. Amarasekara AS, Owereh OS. Synthesis of a sulfonic acid functionalized acidic ionic liquid modified silica catalyst and applications in the hydrolysis of cellulose. Catal Commun. 2010;11:1072–5.

    Article  CAS  Google Scholar 

  23. Yang Q, Wei Z, Xing H, Ren Q. Brönsted acidic ionic liquids as novel catalysts for the hydrolyzation of soybean isoflavone glycosides. Catal Commun. 2008;9:1307–11.

    Article  CAS  Google Scholar 

  24. Zhu GY, Wang R, Liu GH, Xu LQ, Zhang B, Wu XQ. Synthesis of multi-hydroxyl and sulfonyl dual-functionalized room temperature ionic liquids. Chin Chem Lett. 2007;18:633–5.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Authors would like to thank Center for Environmentally Beneficial Catalysis (CEBC), University of Kansas, American Chemical Society-PRF grant UR1-49436 and NSF grant CBET-0929970 for financial support.

Author information

Authors and Affiliations

  1. Department of Chemistry, Prairie View A&M University, Prairie View, TX, 77446, USA

    Ananda S. Amarasekara & Onome S. Owereh

Authors
  1. Ananda S. Amarasekara
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Onome S. Owereh
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ananda S. Amarasekara.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Amarasekara, A.S., Owereh, O.S. Thermal properties of sulfonic acid group functionalized Brönsted acidic ionic liquids. J Therm Anal Calorim 103, 1027–1030 (2011). https://doi.org/10.1007/s10973-010-1101-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-010-1101-5

Keywords

Search

Navigation