Skip to main content
Log in

Urethane-forming reaction kinetics of natural oil polyols versus petroleum-based polyether polyol

  • Published:
Reaction Kinetics, Mechanisms and Catalysis Aims and scope Submit manuscript


Urethane-forming reaction kinetics of isocyanate with natural oil polyols (NOPs) with pendant reactive hydroxyls was compared to that of the petroleum based polyether polyol with terminal hydroxyls. The non-catalyzed urethane forming kinetic study in toluene shows lower activation energy for pendant hydroxyls of the synthetic and naturally occurring NOP compared to terminal hydroxyls of the polyether polyol. At low temperatures in the non-catalyzed reaction in toluene, the NOPs showed higher reactivity with isocyanate, which was correlated with faster gel time in bulk polymerization. However, in toluene, the reactivity of polyether polyol increases at a faster rate with temperature, and in toluene and bulk reactions the polyether polyol shows higher response to dibutyltin dilaurate catalyst. The results indicate that relative reactivities of NOPs compared to polyether polyols are not necessarily lower in urethane forming reactions, and in fact under certain conditions can be higher, which needs to be taken into consideration during the incorporation of NOPs in polyurethanes.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others


  1. Hill K (2000) Fats and oils as oleochemical raw materials. Pure Appl Chem 72(7):1255–1264

    Article  CAS  Google Scholar 

  2. Petrović ZS (2010) Polymers from biological oils. Contemp Mater I–1:39–50

    Article  Google Scholar 

  3. Desroches M, Escouvois M, Auvergne R, Caillol S, Boutevin B (2012) From vegetable oils to polyurethanes: synthetic routes to polyols and main industrial products. Polym Rev 52(1):38–79

    Article  CAS  Google Scholar 

  4. Petrović ZS (2008) Polyurethanes from vegetable oils. Polym Rev 48(1):109–155

    Article  Google Scholar 

  5. Kong X, Liu G, Qi H, Curtis JM (2013) Preparation and characterization of high-solid polyurethane coating systems based on vegetable oil derived polyols. Prog Org Coat 76:1151–1160

    Article  CAS  Google Scholar 

  6. Kong X, Liu G, Qi H, Curtis JM (2012) Novel polyurethane produced from canola oil based poly(ether ester) polyols: synthesis, characterization, and properties. Eur Polym J 48:2097–2106

    Article  CAS  Google Scholar 

  7. Ionescu M (2005) Chemistry and technology of polyols for polyurethanes. Rapra Technology Limited, Shawbury

    Google Scholar 

  8. Sendijarevic V (2011) Natural oil polyols in polyurethane industry—design for performance. Int Palm Oil Cong-Oleo Spec Chem Conf OS 3:59–71

    Google Scholar 

  9. American Chemistry Council (2012) End-use market survey on the polyurethanes industry in the United States, Canada and Mexico. American Chemistry Council, Washington

    Google Scholar 

  10. Oertel G (1985) Polyurethane handbook. Hanser, Munich

    Google Scholar 

  11. Saunders JH, Kurt CF (1962) Polyurethanes: chemistry and technology. Interscience, New York

    Google Scholar 

  12. Herrington R, Hock K (1997) Flexible polyurethane foams. The Dow Chemical Company, Midland

    Google Scholar 

  13. Ionescu M, Petrović ZS, Wan X (2007) Ethoxylated soybean polyols for polyurethanes. J Polym Environ 15(4):237–243

    Article  CAS  Google Scholar 

  14. Pawlik H, Prociak A (2012) Influence of palm oil-based polyol on the properties of flexible polyurethane foams. J Polym Environ 29:438–445

    Article  Google Scholar 

  15. Tan S, Abraham T, Ference D, Macosko CW (2011) Rigid polyurethane foams from a soybean oil-based polyols. Polymer 52(13):2840–2846

    Article  CAS  Google Scholar 

  16. John J, Bhattacharya M, Turner RB (2002) Characterization of polyurethane foams from soybean oil. J Appl Polym Sci 86(12):3097–3107

    Article  CAS  Google Scholar 

  17. Guo A, Zhang W, Petrović ZS (2006) Structure-property relationships in polyurethanes derived from soybean oil. J Mater Sci 41(15):4914–4920

    Article  CAS  Google Scholar 

  18. Campanella A, Bonnaillie LM, Wool RP (2009) Polyurethane foams from soyoil-based polyols. J Appl Polym Sci 112(4):2567–2578

    Article  CAS  Google Scholar 

  19. Tuan Noor Maznee TI, Kosheela Devi PP, Abu Bakar ZB, Seng Soi H, Yeong SK, Hazimah AH, Schiffman C, Sendijarevic A, Sendijarevic V, Sendijarevic I (2015) Urethane-forming reaction kinetics and catalysis of model palm olein polyols: quantified impact of primary and secondary hydroxyls. J Appl Polym Sci 133(5):42955

    Google Scholar 

  20. Fijolka P (1971) Eine methode zur quantitativen differenzierten bestimmung von primären und sekundären hydroxylendgrupper. Plaste Kautsch 18(6):431–432

    CAS  Google Scholar 

  21. Mohd Noor MA, Sendijarevic V, Abu Hassan H, Sendijarevic I, Tuan Ismail TN, Seng Soi H, Hanzah NA, Ghazali R (2015) Polyether polyols as GPC calibration standards for determination of molecular weight distribution of polyether polyols. J Appl Polym Sci 132(43):42698

    Article  Google Scholar 

  22. Noor MA, Sendijarevic V, Hoong SS, Sendijarevic I, Ismail TN, Hanzah NA, Noor NM, Palam KD, Ghazali R, Hassan HA (2016) Molecular weight determination of palm olein polyols by gel permeation chromatography using polyether polyols calibration. JAOCS 93(5):721–730

    Google Scholar 

  23. Yoon HK (1987) Fast-setting casting tape. US Patent 4,655,208

  24. Saurabh T, Patnaik M, Bhagt SL, Renge VC (2011) Epoxidation of vegetable oils: a review. Int J Adv Eng Technol 2:491–501

    Google Scholar 

  25. Derawi D, Salimon J (2010) Optimization of epoxidation of palm olein by using performic acid. J Chem 7(4):1440–1448

    CAS  Google Scholar 

  26. Hazimah AH, Tuan Noor Maznee TI, Mohd Norhisham S, Seng Soi H, Tian Lye O, Salmiah A, Kosheela Devi PP, Mei Yee C (2011) Process to produced polyols. US Patent 7,932,409 B2

  27. Delebecq E, Pascault J, Boutevin B, Ganachaud F (2012) On the versatility of urethane/urea bonds: reversability, blocked isocyanate, and non-isocyanate polyurethanes. Chem Rev 113(1):80–118

    Article  Google Scholar 

  28. Sardon H, Pascual A, Mecerreyes D, Taton D, Cramail H, Hedrick JL (2015) Synthesis of polyurethanes using organocatalysis: a perspective. Macromolecules 48:3153–3165

    Article  CAS  Google Scholar 

Download references


The authors would like to thank Malaysian Palm Oil Board (MPOB) and the Director General of MPOB for providing the financial support for this research work. We would also like to thank our colleagues at Advanced Oleochemical Technology Division and colleagues at Troy Polymers, Inc. for their valuable contributions to this work.

Author information

Authors and Affiliations


Corresponding author

Correspondence to Ibrahim Sendijarevic.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Devi, P.P.K., Maznee, T.I.T.N., Hoong, S.S. et al. Urethane-forming reaction kinetics of natural oil polyols versus petroleum-based polyether polyol. Reac Kinet Mech Cat 119, 93–106 (2016).

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: