Journal of the American Oil Chemists' Society

, Volume 84, Issue 10, pp 929–935 | Cite as

Hydrolysis of Epoxidized Soybean Oil in the Presence of Phosphoric Acid

  • Yinzhong Guo
  • Jon H. Hardesty
  • Vijay M. Mannari
  • John L. MassingillJr
Original Paper

Abstract

Ring-opening hydrolysis of epoxidized soybean oil in the presence of phosphoric acid was studied under varying experimental conditions. The influence of type and amount of solvents, phosphoric acid content and water content on the rate of ring-opening reactions and the characteristics of the derived products were studied. The soy-polyols prepared were characterized by determination of hydroxyl content, viscosity measurements, determination of average molecular weight and polydispersity index (GPC). The structural confirmation was done by FT-IR and 1H-NMR spectroscopy. The study shows that under the reaction conditions employed, a substantial degree of oligomerization due to oxirane-oxirane, and/or oxirane-hydroxyl reaction takes place. It is possible to synthesize soy-polyols having varying hydroxyl content and phosphate-ester functionality by controlling the type and amount of polar solvent and phosphoric acid content.

Keywords

Ring-opening hydrolysis Oxirane content Oligomerization Epoxidized soybean oil 

Notes

Acknowledgments

The authors would like to acknowledge the United Soybean Board for the financial support for this research project.

References

  1. 1.
    Saad ALG, Sayed WM, Ahmed GM (1999) Preparation and properties of some filled poly(vinyl chloride) compositions. J Appl Polym Sci 73:2657–2670CrossRefGoogle Scholar
  2. 2.
    Jia S, Chen GB, Kahar P (1999) Effect of soybean oil on oxygen transfer in the production of tetracycline with an airlift bioreactor. J Biosci Bioeng 87:825–827CrossRefGoogle Scholar
  3. 3.
    Jiratumnukul N, Van de Mark MR (2000) Preparation of glycol esters of soybean oil fatty acids and their potential as coalescent aids in paint formulations. J Am Oil Chem Soc 77:691–697CrossRefGoogle Scholar
  4. 4.
    Jira Sato, Peloggia SH, Hunt T, Schwarzer J, Bueno RC, Lovald RA (2000) Process for the preparation of polyamides. US Patent 6:011–131Google Scholar
  5. 5.
    Erhan SZ, Bagby MO (1994) Polymerization of vegetable-oil and their uses in printing inks. J Am Oil Chem Soc 71:1223–1226CrossRefGoogle Scholar
  6. 6.
    Gibbons WS, Kusy RP (1996) Effects of plasticization on the dielectric properties of poly(vinyl chloride) membranes. Thermochim Acta 284:21–45CrossRefGoogle Scholar
  7. 7.
    Zhang Y, Hourston DJ (1988) Rigid interpenetrating polymer network foams prepared from rosin-based polyurethane and epoxy resin. J Appl Polym Sci 69:271–281CrossRefGoogle Scholar
  8. 8.
    Roy TK, Mannari VM, Raval DA (1997) Synthesis and applications of oil-modified polyesteramide resins for surface coatings. J Sci Ind Res 56:159–163Google Scholar
  9. 9.
    Ahmed S, Ashraf SM, Sharmin E, Zafar F, Hasnat A (2002) Studies on ambient cured polyurethane modified epoxy coatings synthesized from sustainable resources. Prog Cryst Growth Charac Mat 45:83–88CrossRefGoogle Scholar
  10. 10.
    Guo A, Javni I, Petrovic Z (2000) Rigid polyurethane foams based on soybean oil. J Appl Polym Sci 77:467–473CrossRefGoogle Scholar
  11. 11.
    Petrovic ZS, Guo A, Javni A, Zhang W (2000) Optimization of composition of soy-based polyols for rigid polyurethane foams. Annual Technical Conference-Society of Plastics Engineers, 58th 3:3732–3736Google Scholar
  12. 12.
    Petrovic ZS, Javni I, Guo A (1999) Rigid polyurethane foams based on soybean oil, 217th ACS National Meeting, Anaheim, March 21–25Google Scholar
  13. 13.
    Gruber B, Hoefer R, Kluth H, Meffert A (1987) Polyols on the basis of oleochemical raw materials. Fat Sci Technol 89:147–151Google Scholar
  14. 14.
    Daute P, Gruetzmacher R, Hoefer R, Westfechtel A (1993) Saponification-resistant polyols for polyurethane applications based on oleochemical raw materials. Fett Wiss Technol 95:91–4CrossRefGoogle Scholar
  15. 15.
    Khoe TH, Otey FH, Frankel EN (1972) Rigid urethane foams from hydroxymethylated linseed oil and polyol esters. J Am Oil Chem Soc 49:615–618CrossRefGoogle Scholar
  16. 16.
    Lyon CK, Garrett VH, Frankel EN (1974) Rigid urethane foams from hydroxymethylated castor oil, safflower oil, oleic safflower oil, and polyol esters of castor acids. J Am Oil, Chem Soc 51:331–334CrossRefGoogle Scholar
  17. 17.
    Bilyk A, Monroe HA Jr, Saggese EJ, Wrigley (1974) Urethane foams from animal fats. VII. Reaction of epoxidized tallow with trimethylolpropane and TMP [trimethylolpropane]-hydrogen bromide A N. J Am Oil Chem Soc 51:119–122CrossRefGoogle Scholar
  18. 18.
    Saggese EJ, Zubillaga M, Bilyk A, Riser GR, Wrigley AN (1974) Urethane foams from animal fats. VIII. Properties of foams from epoxidized tallow trimethylolpropane polyols. J Am Oil Chem Soc 51:123–125CrossRefGoogle Scholar
  19. 19.
    Scholnick F, Saggese EJ, Wrigley AN, Riser GR (1971) Urethane foams from animal fats. VI. Improved properties of lard and tallow-based foams. J Am Oil Chem Soc 48(11):715–17CrossRefGoogle Scholar
  20. 20.
    Guo A, Cho YJ, Petrovic ZS (2000) Non-halogenated Soy-based Polyols. J Polym Sci A Polym Chem 38:3900–3910CrossRefGoogle Scholar
  21. 21.
    Petrovic ZS, Guo A, Zhang W (2000) Structure and properties of polyurethanes based on halogenated and nonhalogenated soy-polyols. J Polym Sci A Polym Chem 38:4062–4069CrossRefGoogle Scholar
  22. 22.
    Crivello JV, Varlemann U (1995) J Polym Sci A 33:2463–2471CrossRefGoogle Scholar
  23. 23.
    Tokizawa M, Okada H, Wakabayashi N, Kimura T (1993) J Appl Polym Sci 50:627–635CrossRefGoogle Scholar
  24. 24.
    Monte D, Galia M, Cadiz V, Mantecon A, Serra A (1995) Makromol Chem 199:1051–1061Google Scholar
  25. 25.
    Wu S, Soucek MD (1998) Oligomerization mechanism of cyclohexene oxide. Polymer 39:3583–3586CrossRefGoogle Scholar

Copyright information

© AOCS 2007

Authors and Affiliations

  • Yinzhong Guo
    • 1
    • 2
  • Jon H. Hardesty
    • 1
  • Vijay M. Mannari
    • 1
    • 3
  • John L. MassingillJr
    • 1
  1. 1.Institute for Environmental and Industrial ScienceTexas State UniversitySan MarcosUSA
  2. 2.The Dow Chemical Co.MidlandUSA
  3. 3.Eastern Michigan UniversityYpsilantiUSA

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