Skip to main content
SpringerLink
Log in

Cardanol Polymerization Under Acid Conditions By Addition And Condensation Reactions

  • Original Paper
  • Published:
Journal of Polymers and the Environment Aims and scope Submit manuscript

Abstract

Cashew nut shell liquid (CNSL) is a byproduct of the cashew nut industry and consists predominantly of phenolic compounds that have an side chain with different degrees of unsaturation. Cardanol, one of these components, is biodegradable and widely available. Studies have revealed several polymerization reactions involving cardanol. However, the mechanisms and detailed structures of polymerization reactions have not been explored, although the final product shows different applications. In this work, we evaluated the mechanism and the products structure of the reaction of cardanol with: (i) boron trifluoride diethyl etherate (BF3O(CH2CH3)2), and (ii) formaldehyde. The characterizations were performed by FTIR, 1H NMR, SEC and TGA. The results show that the reaction of cardanol with aldehyde produces the expected like-comb structure with a long hydrocarbon pendent chain. Nevertheless, the reaction of cardanol with BF3O(CH2CH3)2 can exhibits a more complex structure since it was identified aromatic ring linkages, besides the expected polymerization through C=C.

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
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

References

  1. Voirin C, Caillol S, Sadavarte NV, Tawade BV, Boutevin B, Wadgaonkar PP (2014) Polym Chem 5:3142.

    Article  CAS  Google Scholar 

  2. Lima AF, Mansur CRE, Lucas EF, González G (2010) Energy Fuels 24:2369

    Article  CAS  Google Scholar 

  3. Ferreira SR, Louzada HF, Dip RMM, González G, Lucas EF (2015) Energy Fuels 29:7213

    Article  CAS  Google Scholar 

  4. Zhou Q, Cho D, Ho Park W, Keun Song B, Kim H-J (2011) J Appl Polym Sci 122:2774

    Article  CAS  Google Scholar 

  5. Ionescu M, Wan X, Bilić N, Petrović ZS (2012) J Polym Environ 20:647

    Article  CAS  Google Scholar 

  6. Souza FG, Pinto JC, Rodrigues MV, Anzai TK, Richa P, Melo PA, Nele M, Oliveira GE, Soares BG (2008) Polym Eng Sci 48:1947

    Article  CAS  Google Scholar 

  7. Sakulsaknimitr W, Wirasate S, Pipatpanyanugoon K, Atorngitjawat P (2015) J Polym Environ 23:216

    Article  CAS  Google Scholar 

  8. Moreira LFB, Lucas EF, González G (1999) J Appl Polym Sci 73:29

    Article  CAS  Google Scholar 

  9. Rios Façanha MA, Mazzetto SE, Beserra Carioca JO, de Barros GG (2007) Fuel 86:2416

    Article  Google Scholar 

  10. Antony R, Pillai CKS, Scariah KJ (1990) J Appl Polym Sci 41:1765

    Article  CAS  Google Scholar 

  11. Devi A, Srivastava D (2006) J Appl Polym Sci 102:2730

    Article  CAS  Google Scholar 

  12. Sood SK, Tyman JHP, Durrani A, Johnson RA (1986) Lipids 21:241

    Article  CAS  Google Scholar 

  13. Rodrigues FHA, Souza RJR, França FCF, Nágila MPSR, Judith PAFE (2006) Polymers 6:1027

    Google Scholar 

  14. Kim YH, Won K, Kwon JM, Jeong HS, Park SY, An ES, Song BK (2005) J Mol Catal B 34:33

    Article  CAS  Google Scholar 

  15. Rao BS, Palanisamy A (2013) Eur Polym J 49:2365

    Article  CAS  Google Scholar 

  16. Kiratitanavit W, Ravichandran S, Xia Z, Kumar J, Nagarajan R (2013) J Renew Mat 1:289

    Article  CAS  Google Scholar 

  17. Bai W, Xiao X, Chen Q, Xu Y, Zheng S, Lin J (2012) Prog Org Coat 75:184

  18. Cheremisinoff NP (1997).) Handbook of Engineering polymeric materials. CRC Press, New York

    Google Scholar 

  19. Chuayjuljit S, Rattanametangkool P, Potiyaraj P (2007) J Appl Polym Sci 104:1997

    Article  CAS  Google Scholar 

  20. Yadav R, Srivastava D (2007) Mater Chem Phys 106:74

    Article  CAS  Google Scholar 

  21. Srivastava R, Srivastava D (2015) J Polym Environ 23:283

    Article  CAS  Google Scholar 

  22. Lubi MC, Thachil ET (2000) Des Monomers Polym 3:123

    Article  CAS  Google Scholar 

  23. Natarajan M, Murugavel SC (2013) High Perform Polym 25:685

    Article  Google Scholar 

  24. Sultania M, Rai JSP, Srivastava D (2010) Eur Polym J 46:2019

    Article  CAS  Google Scholar 

  25. Shibata M, Itakura Y, Watanabe H (2013) Polym J 45:758

    Article  CAS  Google Scholar 

  26. Kim YH, An ES, Park SY, Song BK (2007) J Mol Catal B 45:39

    Article  CAS  Google Scholar 

  27. Bruice PY (2004) Organic chemistry. Pearson/Prentice Hall, New Jersey

    Google Scholar 

  28. Ravichandran S, Bouldin RM, Kumar J, Nagarajan R (2011) J Clean Prod 19:454

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank CAPES, CNPq and FAPERJ for financial support.

Author information

Authors and Affiliations

  1. Universidade Federal do Rio de Janeiro, Instituto de Macromoléculas, Laboratório de Macromoléculas e Colóides na Indústria de Petróleo, Av. Horácio Macedo, 2030, Rio de Janeiro, RJ, 21941-598, Brazil

    Tatiana Loureiro, Rocio Macarena Moyano Dip, Elizabete Lucas & Luciana Spinelli

  2. Universidade Federal do Rio de Janeiro, Instituto Alberto Luiz Coimbra de Pós-Graduação e Pesquisa em Engenharia, Programa de Engenharia Metalúrgica e de Materiais, Av. Horácio Macedo, 2030, Bl. K, Ilha do Fundão, Rio de Janeiro, 21941-598, Brazil

    Elizabete Lucas

  3. Universidade Federal do Rio de Janeiro, Instituto Alberto Luiz Coimbra de Pós-Graduação e Pesquisa em Engenharia, Programa de Engenharia de Nanotecnologia, Av. Horácio Macedo, 2030, Bl. G, Ilha do Fundão, Rio de Janeiro, 21941-598, Brazil

    Luciana Spinelli

Authors
  1. Tatiana Loureiro
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rocio Macarena Moyano Dip
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Elizabete Lucas
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Luciana Spinelli
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Tatiana Loureiro.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Loureiro, T., Dip, R.M.M., Lucas, E. et al. Cardanol Polymerization Under Acid Conditions By Addition And Condensation Reactions. J Polym Environ 26, 555–566 (2018). https://doi.org/10.1007/s10924-017-0969-6

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10924-017-0969-6

Keywords

Search

Navigation