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


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.


Ring-opening hydrolysis Oxirane content Oligomerization Epoxidized soybean oil 



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


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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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