Journal of the American Oil Chemists' Society

, Volume 88, Issue 8, pp 1143–1151

Bidirectional Conversion Between 3-Monochloro-1,2-propanediol and Glycidol in Course of the Procedure of DGF Standard Methods


  • Naoki Kaze
    • Ueda Oils and Fats MFG Co. Ltd
  • Hirofumi Sato
    • Osaka Municipal Technical Research Institute
  • Hiroshi Yamamoto
    • Ueda Oils and Fats MFG Co. Ltd
    • Osaka Municipal Technical Research Institute
Original Paper

DOI: 10.1007/s11746-011-1802-3

Cite this article as:
Kaze, N., Sato, H., Yamamoto, H. et al. J Am Oil Chem Soc (2011) 88: 1143. doi:10.1007/s11746-011-1802-3


NMR observation revealed that bidirectional conversion occurred between 3-monochloropropane-1,2-diol (3-MCPD) and glycidol in the course of the analytical procedure of DFG standard method C-III 18 (09), option A; 3-MCPD was partly converted to glycidol at the transesterification step, and glycidol was converted partly to 3-MCPD at the derivatization step conducted at 80 °C under acidic condition in the presence of NaCl. Based on the proton numbers observed by 1H NMR, the degrees of the conversion were estimated to be 37 and >70%, respectively. In addition, epoxide ring-opening of glycidol and its esters was found to be ca. 90% by the acid treatment described in the method, option B. Thus, it was concluded that the standard method, option A, did not correctly give the combined amount of 3-MCPD esters and glycidyl esters in oils containing glycidyl esters, and the difference of the values obtained by options A and B did not correspond to the amount of glycidyl esters, either. In addition, derivatives of 3-MCPD with phenylboronic acid were not observed by NMR at the derivatization step, although they were detected by GC-MS in the organic phase at the following extraction step.


3-Monochloropropane-1,2-diol (3-MCPD)DFG standard methodGlycidolGlycidyl esterNaCl

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© AOCS 2011