Study on the Condensation Reaction of Alkyl Glycidyl Ethers and Fatty Acids

알킬 글리시딜에테르와 지방산의 축합반응 연구

  • Kim, Ji-Hyun (Department of Fine Chemical Engineering and Chemistry, BK21-E2M, Chungnam National University) ;
  • Hwang, Hyun Ah (Department of Green Chemistry and Environmental Biotechnology, University of Science & Technology) ;
  • Lee, Young-Seak (Department of Fine Chemical Engineering and Chemistry, BK21-E2M, Chungnam National University) ;
  • Lee, Byung Min (Environment and Resources Research Center, Korea Research Institute of Chemical Technology)
  • 김지현 (충남대학교 바이오응용화학과) ;
  • 황현아 (과학기술연합대학원대학교 청정화학 및 생물학) ;
  • 이영석 (충남대학교 바이오응용화학과) ;
  • 이병민 (한국화학연구원 그린화학공정연구본부)
  • Published : 2012.08.10

Abstract

A convenient procedure for the synthesis of fatty acid diesters was studied. Long chain diesters have been used as biolubricant and transformer oils. The series of octyl, dodecyl, hexadecyl, octadecyl, and octadec-9-enyl glycidyl ether were used to synthesize those diesters. Alkyl glycidyl ethers were reacted with fatty acid such as oleic acid and octanoic acid, and octanoic acid. The one-step / two-step reactions were compared during the condensation reaction. The products were confirmed by $^{1}H-NMR$, FT-IR, and HR/MS spectra. The yield of the product 1-O-acyl-2-O, 3-O-dioctadec-9-enoylglycerol was 55~60%.

지방산 디에스테르 합성의 편리한 방법을 연구하였다. 긴 사슬 디에스테르는 천연윤활제와 절연유로서 많이 사용된다. 옥틸, 도데실, 헥사데실, 옥타데실 그리고 옥타-9-엔일 글리시딜 에테르 계열을 이러한 디에스터 구조를 합성하기 위해 사용하였다. 알킬 글리시딜에테르를 올레인산 그리고 옥타노익산과 같은 지방산과 반응시켰으며, one-step / two-step 축합반응을 비교하였다. 생성물인 1-O-acyl-2-O, 3-O-dioctadec-9-enoylglycerol은 $^{1}H-NMR$, FT-IR 그리고 HR/MS 스펙트럼을 통해 확인하였으며, 수율은 55~60%이었다.

Keywords

References

  1. J. Salimon, N. Salih, and E. Yousif, Eur. J. Lipid Sci. Technol., 112, 519 (2010).
  2. J. Salimon, N. Salih, and E. Yousif, J. King Saud Uni. Sci., 24, 11 (2012). https://doi.org/10.1016/j.jksus.2010.08.008
  3. J. Salimon, N. Salih, and E. Yousif, Kem. Ind., 60, 127 (2011).
  4. J. Salimon, N. Salih, and E. Yousif, J. Saudi Chem. Soci., 15, 195 (2011). https://doi.org/10.1016/j.jscs.2010.08.004
  5. U. S. Patent 7,867,959 (2011).
  6. R. Yunus, A. Rakhru'l-Razi, T. L. Ooi, S. E. lyuke, and A. Idris, J. Oil Palm Res., 15, 35 (2003).
  7. Y. Linko, T. Tervakangas, M. Lamsa, and P. Linko, Biotechnol. Tech., 11, 889 (1995).
  8. V. Eychenne, Z. Mouloungui, and A. Gaset, J. Am. Oil Chem. Soc., 75, 293 (1998). https://doi.org/10.1007/s11746-998-0044-5
  9. S. Cryglewicz, W. Piechocki, and G. Cryglewicz, Bioresour. Techonol., 87, 35 (2003). https://doi.org/10.1016/S0960-8524(02)00203-1
  10. A. Igartua, X. Fernandez, O. Areitioaurtena, R. Luther, C. Seyfert, and J. Fausch, Tribology Inter., 42, 561 (2009). https://doi.org/10.1016/j.triboint.2008.10.015
  11. H. C. Kang, B. M. Lee, J. Yoon, and M. Yoon, J. Am. Oil Chem. Soc., 78, 423 (2000).
  12. D. H. Wang and H. S. Weng, Chem. Eng. Sci., 50, 3477 (1995). https://doi.org/10.1016/0009-2509(95)00178-8
  13. D. M. Dishong, C. J. Diamond, M. I. Cinoman, and G. W. Gokel, J. Am. Chem. Soc., 105, 586 (1983). https://doi.org/10.1021/ja00341a045