Skip to main content
SpringerLink
Log in

Synthesis and characterization of different types of epoxide-based Mannich polyols from low-cost cashew nut shell liquid

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Cashew nut shell liquid (CNSL) is a natural aromatic organic oil consisting of phenolic compounds with interesting structures. Extraction of CNSL was performed in a Soxhlet apparatus. The major (90 %) component of CNSL is anacardic acid, which is easily decarboxylated to cardanol (10 %) by use of conventional methods. In this paper we describe a three-step synthesis of Mannich polyols for rigid foams. The first step is synthesis of N-(2-hydroxyethyl)-1,3-oxazolidine (the Mannich precursor) by condensation of paraformaldehyde and diethanolamine. The second step involves synthesis of the Mannich base phenolic ring of cardanol by reaction with N-(2-hydroxyethyl)-1,3-oxazolidine. The third step is alkoxylation. The synthesized polyols were characterized by FTIR and 1H NMR spectroscopy and thin-layer chromatography.

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

Similar content being viewed by others

References

  1. P. Phani Kumar, J.R.P. Paramashivappa, J. Vithayathil, P.V. Subba, A.S. Rao, J. Agric. Food Chem. 50, 47 (2002)

    Article  Google Scholar 

  2. P. Das, T. Sreelatha, A. Ganesh, J. Biomass Bioenerg. 27, 265 (2004)

    Article  CAS  Google Scholar 

  3. T. Gandhi, M. Patel, B. Dholakiya, J. Nat. Prod. Plant Resour. 2(1), 135 (2012)

    CAS  Google Scholar 

  4. J.H.P. Tyman, I.E. Bruce, J. Surfactants Deterg. 6, 291 (2003)

    Article  CAS  Google Scholar 

  5. E.L. Short, V. Tychopoulos, J.H.P. Tyman, Long chain phenols—part 30. J. Chem. Technol. Biotechnol. 53, 389 (1992)

    Article  CAS  Google Scholar 

  6. R. Ikeda, H. Tanaka, H. Uyama, A.S. Kobayashi, J. Macromol. Rapid Commun. 21, 496 (2000)

    Article  CAS  Google Scholar 

  7. P. Campaner, D. Amico, L. Longo, C. Stifani, A. Tarzia, J. Appl. Polym. Sci. 114, 35 (2009)

    Article  Google Scholar 

  8. T.D. Thien, N. Vankhoi, Q.D. Khang, D. Vanluyen, J. Macromol. Sci. A 33, 19 (1996)

    Article  Google Scholar 

  9. H.P. Bhunia, N.R. Jana, A. Basak, S. Lenka, G.B. Nando, J. Polym. Sci. A. Chem. 36, 391 (1998)

    Article  CAS  Google Scholar 

  10. I. K. Suresh, S.V. Kishanprasad, US Pat. 7, 244, 772

  11. I.K. Suresh, S.V. Kishanprasad, Ind. Eng. Chem. Res. 44, 45 (2005)

    Article  Google Scholar 

  12. M. Ionescu, S. Fu, N. Bilic, I. Javni, S.Z. Petrovic, in CPI Polyurethane Technical Conference, Houston, Texas, 11–13 October (2010)

  13. M. Ionescu, X. Wan, S. Petrovic Z, Cashew Nut Oil Polyols for Polyurethanes, International Chemical Congress of Pacific Basin Societies-PACIFICHEM. Honolulu, Hawaii, Dec 15–20 (2010)

  14. M. Ionescu, Chemistry and technology of polyols for polyurethanes (Rapra Technology Ltd, Shropshire, 2005), pp. 381–400

    Google Scholar 

  15. M. Ionescu, V. Zugravu, I. Mihalache, S. Mihai, Synthesis of New Aromatic Mannich Polyols for Rigid Polyurethane Foams Advances in Urethane Science & Technology, vol 14 (Technomic Publishing Company, Lancaster, 1998), pp. 151–217

    Google Scholar 

  16. M. Ionescu, Chemistry and Technology of Polyols for Polyurethanes, vol 13, 15 (RAPRA, Anglia, 2006)

    Google Scholar 

  17. B. Reichert, Die Mannich-Reaction (Springer, Verlag, Berlin, 1959), p. 8

    Book  Google Scholar 

  18. E. C. Britton, G. H. Coleman, US Pat. 2,022,182

  19. M. Ionescu, I. Mihalache, V. Zugravu, S. Mihai, J. Cell. Polym. 13(1), 57–68 (1994)

    CAS  Google Scholar 

  20. C.K. Frish, L.S. Reegen, J. Mater. Sci. 2, 128 (1969)

    Google Scholar 

  21. ASTM E222 Standard test methods for hydroxyl groups using acetic anhydride acetylation. (2000)

  22. M. Ionescu, S. Mihai, L. Dumitrache, I. Enache, J. Mater. Plast. 1, 45 (2008)

    Google Scholar 

Download references

Acknowledgments

The author wish to thank the Department of Applied Chemistry, SVNIT, Surat, for providing laboratory facilities, and Gujarat Cashew Industrial (Kutch, Gujarat, India), for providing the initial product. Analytical facilities provided by the Centre of Excellence, Vapi, Gujarat, India, and Punjab University, Chandigarh, India, are gratefully acknowledged.

Author information

Authors and Affiliations

  1. Department of Applied Chemistry, Sardar Vallabhbhai National Institute of Technology (SVNIT), Surat, 395007, Gujarat, India

    Tejas S. Gandhi & Bharatkumar Z. Dholakiya

  2. Chemical Sciences Department, N. V. Patel College of Pure & Applied Sciences, Vallabh Vidyanagar, 388120, Gujarat, India

    Mayank R. Patel

Authors
  1. Tejas S. Gandhi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mayank R. Patel
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bharatkumar Z. Dholakiya
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Bharatkumar Z. Dholakiya.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gandhi, T.S., Patel, M.R. & Dholakiya, B.Z. Synthesis and characterization of different types of epoxide-based Mannich polyols from low-cost cashew nut shell liquid. Res Chem Intermed 40, 1223–1232 (2014). https://doi.org/10.1007/s11164-013-1034-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-013-1034-2

Keywords

Search

Navigation