Novel Palm Oil Based Polyols with Amide functionality

Sabrina Soloi, Rohah Abdul Majid, Abdul Razak Rahmat, Jamarosliza Jamaluddin


In polymer chemistry, polyol usually used as starting materials for polyurethane (PU) production in which upon reacted with isocyanate will affect the physical and chemical properties of the obtained PU. Polyols that are mostly derived from petrochemical resources are facing the issues such as depletion of petroleum sources as well as the increasing in market price. Ring opening reaction (ROR) of epoxidized palm oil (EPO) had been carried out using isopropanolamine (IPA) to impart polyol with amide functionality. The effect of reaction time on the opening of oxirane ring was investigated. FTIR spectra showed that the oxirane ring of EPO can occurs at 6 hours reaction time, corresponding to the deacreasing intensity of  oxirane band at 824-830 cm-1. The OH value of the amide- functionalized-polyol was calculated at around 240-253 mg KOH/g. By prolonging the reaction time the OH value has slightly reduced. Mass spectroscopy analysis revealed that the polyol has a molecular weight in the range of oligo-polyols (400 – 500 Da).


Ring opening reaction; epoxidized palm oil; isopropanolamine; bio-based polyols; amide polyol.

Full Text:



M. Alam, D. Akram, E. Sharmin, F. Zafar, and S. Ahmad, “Vegetable oil based eco-friendly coating materials: A review article,” Arab. J. Chem., vol. 7, no. 4, pp. 469–479, Sep. 2014.

M. Desroches, M. Escouvois, R. Auvergne, S. Caillol, and B. Boutevin, “From Vegetable Oils to Polyurethanes: Synthetic Routes to Polyols and Main Industrial Products,” Polymer Reviews, vol. 52, no. 1. Taylor & Francis, pp. 38–79, 01-Jan-2012.

G. Lligadas, J. C. Ronda, M. Galià, and V. Cádiz, “Plant Oils as Platform Chemicals for Polyurethane Synthesis: Current State-of-the-Art,” Biomacromolecules, vol. 11, no. 11, pp. 2825–2835, 2010.

M. Jalilian, H. Yeganeh, and M. N. Haghighi, “Synthesis and properties of polyurethane networks derived from new soybean oil-based polyol and a bulky blocked polyisocyanate,” Polym. Int., vol. 57, no. 12, pp. 1385–1394, Dec. 2008.

E. A. Ismail, A. M. Motawie, and E. M. Sadek, “Synthesis and characterization of polyurethane coatings based on soybean oil–polyester polyols,” Egypt. J. Pet., vol. 20, no. 2, pp. 1–8, 2011.

H. Bakhshi, H. Yeganeh, S. Mehdipour-Ataei, M. A. Shokrgozar, A. Yari, and S. N. Saeedi-Eslami, “Synthesis and characterization of antibacterial polyurethane coatings from quaternary ammonium salts functionalized soybean oil based polyols,” Mater. Sci. Eng. C, vol. 33, no. 1, pp. 153–164, 2013.

X. Kong, G. Liu, and J. M. Curtis, “Characterization of canola oil based polyurethane wood adhesives,” Int. J. Adhes. Adhes., vol. 31, no. 6, pp. 559–564, Sep. 2011.

A. S. A. Hazmi, M. M. Aung, L. C. Abdullah, M. Z. Salleh, and M. H. Mahmood, “Producing Jatropha oil-based polyol via epoxidation and ring opening,” Ind. Crops Prod., vol. 50, no. 0, pp. 563–567, 2013.

S. N. Khot et al., “Development and application of triglyceride-based polymers and composites,” J. Appl. Polym. Sci., vol. 82, pp. 703–723, 2001.

M. a R. Meier, J. O. Metzger, and U. S. Schubert, “Plant oil renewable resources as green alternatives in polymer science.,” Chem. Soc. Rev., vol. 36, no. 11, pp. 1788–1802, 2007.

A. Dotan, Handbook of Thermoset Plastics. Elsevier, 2014.

P. D. Meshram, R. G. Puri, A. L. Patil, and V. V. Gite, “Synthesis and characterization of modified cottonseed oil based polyesteramide for coating applications,” Prog. Org. Coatings, vol. 76, no. 9, pp. 1144–1150, 2013.

R. D. Kulkarni, P. S. Deshpande, S. U. Mahajan, and P. P. Mahulikar, “Epoxidation of mustard oil and ring opening with 2-ethylhexanol for biolubricants with enhanced thermo-oxidative and cold flow characteristics,” Ind. Crops Prod., vol. 49, pp. 586–592, Aug. 2013.

A. Guo, D. Demydov, W. Zhang, and Z. S. Petrovic, “Polyols and polyurethanes from hydroformylation of soybean oil,” J. Polym. Environ., vol. 10, pp. 49–52, 2002.

Z. S. Petrović, W. Zhang, and I. Javni, “Structure and properties of polyurethanes prepared from triglyceride polyols by ozonolysis,” Biomacromolecules, vol. 6, no. 2, pp. 713–719, 2005.

V. V. Goud, S. Dinda, A. V. Patwardhan, and N. C. Pradhan, “Epoxidation of Jatropha (Jatropha curcas) oil by peroxyacids,” Asia-Pacific J. Chem. Eng., vol. 5, no. 2, pp. 346–354, 2010.

FOASTAT, “Food and Agriculture Organization of The United Nations,” 2014.

M. Z. Arniza et al., “Synthesis of Transesterified Palm Olein-Based Polyol and Rigid Polyurethanes from this Polyol,” J. Am. Oil Chem. Soc., vol. 92, no. 2, pp. 243–255, 2015.

L. H. Gan, S. H. Goh, and K. S. Ooi, “Kinetic studies of epoxidation and oxirane cleavage of palm olein methyl esters,” J. Am. Oil Chem. Soc., vol. 69, no. 4, pp. 347–351, 1992.

C. S. Lee, T. L. Ooi, C. H. Chuah, and S. Ahmad, “Rigid Polyurethane Foam Production from Palm Oil-Based Epoxidized Diethanolamides,” J. Am. Oil Chem. Soc., vol. 84, no. 12, pp. 1161–1167, Oct. 2007.

K. H. Badri, S. H. Ahmad, and S. Zakaria, “Production of a high-functionality RBD palm kernel oil-based polyester polyol,” J. Appl. Polym. Sci., vol. 81, no. 2, pp. 384–389, Jul. 2001.

D. Lumcharoen and O. Saravari, “Preparation and Characterization of Flexible Polyurethane Foams from Palm Oil-Based Polyol,” Adv. Mater. Res., vol. 911, pp. 352–356, 2014.

J. G. Smith, “Oxidation and Reduction,” in Organic Chemistry, 2006, p. 419.

D. Derawi and J. Salimon, “Optimization on Epoxidation of Palm Olein by Using Performic Acid,” E-Journal Chem., vol. 7, no. 4, pp. 1440–1448, 2010.

S. S. Narine, J. Yue, and X. Kong, “Production of polyols from canola oil and their chemical identification and physical properties,” JAOCS, J. Am. Oil Chem. Soc., vol. 84, pp. 173–179, 2007.

S. H. Feairheller, R. G. Bistline Jr., A. Bilyk, R. L. Dudley, M. F. Kozempel, and M. J. Haas, “A novel technique for the preparation of secondary fatty amides,” J. Am. Oil Chem. Soc., vol. 71, no. 8, pp. 863–866, 1994.

T. F. Garrison, M. R. Kessler, and R. C. Larock, “Effects of unsaturation and different ring-opening methods on the properties of vegetable oil-based polyurethane coatings,” Polymer (Guildf)., vol. 55, no. 4, pp. 1004–1011, 2014.

S. Miao, S. Zhang, Z. Su, and P. Wang, “Synthesis of bio-based polyurethanes from epoxidized soybean oil and isopropanolamine,” J. Appl. Polym. Sci., vol. 127, pp. 1929–1936, 2013.

B. J. K. Ahn, S. Kraft, and X. S. Sun, “Solvent-free acid-catalyzed ring-opening of epoxidized oleochemicals using stearates/stearic acid, and its applications,” J. Agric. Food Chem., vol. 60, pp. 2179–2189, 2012.

H. Dai, L. Yang, B. Lin, C. Wang, and G. Shi, “Synthesis and Characterization of the Different Soy-Based Polyols by Ring Opening of Epoxidized Soybean Oil with Methanol, 1,2-Ethanediol and 1,2-Propanediol,” J. Am. Oil Chem. Soc., vol. 86, no. 3, pp. 261–267, Jan. 2009.

Z. Lozada, G. J. Suppes, Y. C. Tu, and F. H. Hsieh, “Soy-based polyols from oxirane ring opening by alcoholysis reaction,” J. Appl. Polym. Sci., vol. 113, no. 4, pp. 2552–2560, Aug. 2009.

W. R. Morrison and L. M. Smith, “Preparation of fatty acid methyl esters and dimethylacetals from lipids with boron fluoride–methanol,” J. Lipid Res. , vol. 5, no. 4, pp. 600–608, Oct. 1964.

Z. S. Petrović, “Polymers From Biological Oils,” Contemp. Mater., vol. I, no. 1, pp. 39–50, 2010.

“AOCS.” [Online]. Available: [Accessed: 15-Aug-2016].

J. G. Smith, Organic Chemistry, Internatio. New York: Mc Graw Hill, 2006.

A. Biswas, A. Adhvaryu, S. H. Gordon, S. Z. Erhan, and J. L. Willett, “Synthesis of diethylamine-functionalized soybean oil.,” J. Agric. Food Chem., vol. 53, no. 24, pp. 9485–90, Nov. 2005.

H. a Mohamed, B. M. Badran, and H. a Aglan, “Waterborne Methylamine Adduct as Corrosion Inhibitor for,” pp. 286–296, 2000.

E. Deffense, “Fractionation of palm oil,” J. Am. Oil Chem. Soc., vol. 62, no. 2, pp. 376–385, 1985.

T. Ollevier and G. Lavie-Compin, “Bismuth triflate-catalyzed mild and efficient epoxide opening by aromatic amines under aqueous conditions,” Tetrahedron Lett., vol. 45, no. 1, pp. 49–52, 2004.

L. G. Butler, “An Introduction to Solution, Solid-State, and Imaging NMR Spectroscopy,” in Handbook of Spectroscopy, Wiley-VCH Verlag GmbH & Co. KGaA, 2003, pp. 177–208.

Mihail Ionescue, Chemistry and Technology of Polyols for Polyurethanes. Shropshire, UK: Rapra Technology Limited, 2005.

K. P. Ang, C. S. Lee, S. F. Cheng, and C. H. Chuah, “Synthesis of palm oil-based polyester polyol for polyurethane adhesive production,” J. Appl. Polym. Sci., vol. 131, no. 6, p. 39967 (1 0f 8), Mar. 2014.


  • There are currently no refbacks.





About IJSBAR | Privacy PolicyTerms & Conditions | Contact Us | DisclaimerFAQs 

IJSBAR is published by (GSSRR).