Synthesis of glycerol 1-monooleate by condensation of oleic acid with glycidol catalyzed by anion-exchange resin in aqueous organic polymorphic system

Industrial and Engineering Chemistry Research

Volumn 48, Issue 15, 2009, Pages 6949-6956

  Mouloungui, Zéphirin ^a   Rakotondrazafy, Vony ^a   Valentin, Romain ^a   Zebib, Bachar ^a  

^a UNIVERSITÉ DE TOULOUSE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM GROUPS; ANION EXCHANGE RESINS; AQUEOUS MEDIUM; CATALYTIC EFFICIENCIES; CATALYTIC ROLE; DISCONTINUOUS PROCESS; FACTORIAL DESIGN; FRACTIONAL FACTORIALS; FUNCTIONAL FORMS; GLYCIDOL; MACROPOROUS; MAIN PARAMETERS; MOLAR RATIO; POLYMORPHIC SYSTEM; SELECTIVE SYNTHESIS; STIRRED REACTORS;

AMMONIUM COMPOUNDS; CONDENSATION; FUNCTIONAL POLYMERS; GLYCEROL; ION EXCHANGE RESINS; MICROEMULSIONS; NEGATIVE IONS; OLEIC ACID;

CONDUCTING POLYMERS;

EID: 68849088041     PISSN: 08885885     EISSN: None     Source Type: Journal    
DOI: 10.1021/ie900101k     Document Type: Article

References (31)

1. Hartunian-Sowa, S. M.; White, P. J.; Batres, L. V. Influence of Monoglycerides of Different Chain Lengths on Texture and Flavor of Breads Made with Waxy Cornstarch. Starch-Stärke 1990, 42 (2), 53-56.
2. 1990, 42, 2, 53.
3. Fujimura, M.; Yamauchi, H.; Matsushita, T.; Oshima, M.; Oya, K. Shortenings Containing Glycerides and Amylase and/or Protease and Their Manufacture. Japanese Patent JP 03 292 848, 1991.
4. Rieger, M. Glyceryl stearate, chemistry and use. Cosmet. Toiletries 1990, 105, 51.
5. Kabara, J. J.; Lie, M. S. F. Antimicrobial Lipids: Natural and Synthetic Fatty Acids and Monoglycerides. Lipids 1977, 12 (9), 753.
6. Kato, N. Antimicrobial Activity of Fatty Acids and Their Esters against a Film-Forming Yeast in Soy Sauce. J. Food Safety 1981, 3 (2), 121.
7. Kamei, T.; Teraoka, T.; Hirano, H. Antistatic Acrylic Polymer or Polycarbonate Laminate Sheets. Japanese Patent JP 02 276 636, 1990.
8. Mc Intire, R. T. Fatty Acids in Industry; Marcel Dekker: New York, 1989.
9. Mouloungui, Z.; Gauvrit, C. Synthesis and influence of fatty acid esters on the foliar penetration of herbicides. Ind. Crops Prod. 1998, 8, 01.
10. Lok, C. M. Glyceride Esters. U.S. Patent 4,234,498, 1980.
11. Burgos, C. E.; Ayer, D. E.; Johnson, R. A. A new, asymmetric synthesis of lipids and phospholipids. J. Org. Chem. 1987, 52 (22), 4973.
12. Caron, M.; Sharpless, K. B. Titanium isopropoxide-mediated nucleophilic openings of 2,3-epoxy alcohols. A mild procedure for regioselective ring-opening. J. Org. Chem. 1985, 50 (9), 1557.
13. Tamura, T. Preparation of Higher Fatty Acid Monoglycerides from Fatty Acids and Glycidol. Japanese Patent JP 04182451, 1992.
14. Cauvel, A.; Renard, G.; Brunel, D. Monoglyceride Synthesis by Heterogeneous Catalysis Using MCM-41 Type Silicas Functionalized with Amino Groups. J. Org. Chem. 1997, 62 (3), 749.
15. Janis, J.; Krejc, J.; Klásek, K. Preparation of 1-monoacylglycerois from glycidoI and fatty acids catalyzed by the chromium(III)-fatty acid system. Eur. J. Lipid Sci. Technol. 2000, 102 (5), 351.
16. Jaenicke, S.; Chuah, G. K.; Lin, X. H.; Hu, X. C. Organic-inorganic hybrid catalysts for acid-and base-catalyzed reactions. Microporous Mesoporous Mater. 2000, 35-36, 143.
17. Mouloungui, Z.; Rakotondrazafy, V.; Peyrou, G.; Gachen, C.; Eychenne, V. Pure R-monoglycerides for industrial applications. Agro Food Ind. Hi-Tech. 1998, 9 (4), 10-14.
18. Jamet, J.-P.; Mouloungui, Z.; Peyrou, G.; Gachen, C.; Rakotondrazafy, V.; Gaset, A. Process and equipment for the synthesis of monoglycérides. French Patent FR 2723088, 1995.
19. Chapelle, S.; Baudrand, V.; Rakotondrazafi, V.; Mouloungui, Z.; Gaset, A. Deacidification of lipophilic media by binding free fatty acids to anion exchange resins. Riv. Ital. Sost. Grasse 1995, 72, 153.
20. Zlatanos, S.; Sagredos, A.; Papageorgiou, V. High yield monoglycerides preparation from glycidol and carboxylic acids, Society. J. Am. Oil Chem. Soc. 1985, 62 (11), 1575.
21. Dooley, K. M.; Williams, J. A.; Gates, B. C.; Albright, L. Sulfonated poly(styrene-divinylbenzene) catalysts: II. Diffusion and the influence of macroporous polymer physical properties on the rate of reesterification. J. Catal. 1982, 74, 361.
22. Jiang, X.-K. Hydrophobic-Lipophilic Interactions. Aggregation and Self-Coiling of Organic Molecules. Acc. Chem. Res. 1988, 21, 362.
23. Harris, D. C. Quantitative Chemical Analysis, 3rd ed.; W. H. Freeman & Company: New York, 1991; p 734.
24. Ihm, S.-K.; Oh, I.-H. Correlation of a two-phase model for macroreticular resin catalyst. J. Chem. Eng. Jpn. 1984, 17, 58.
25. Satterfield, C. N. Heterogeneous Catalysts in Industrial Practice, 2nd ed.; McGraw-Hill: New York, 1991.
26. Ljusberg-Wahren, H.; Herslöf, M.; Larsson, K. A comparison of the phase behaviour of the monoolein isomers in excess water. Chem. Phys. Lipids 1983, 33 (2), 211.
27. Krog, N.; Larsson, K. Phase behaviour and rheological properties of aqueous systems of industrial distilled monoglycérides. Chem. Phys. Lipids 1968, 2 (1), 129.
28. Garti, N. Microemulsions as microreactors for food applications. Curr. Opin. Colloid Interface Sci. 2003, 8 (2), 197.
29. Larsson K. Lipids: Molecular Organization, Physical Functions and Technical Applications, The Oily Press: Dundee, Scotland, 1994.
30. Hinze, W. L. Utilization of surfactant systems in chemical separation. Ann. Chim. (Roma) 1987, 77, 167.
31. Peyrou, G.; Rakotondrazafy, V.; Mouloungui, Z.; Gaset, A. Separation and quantitation of mono-, di-, and triglycerides and free oleic acid using thin-layer chromatography with flame-ionization detection. Lipids 1996, 31 (1), 27.