Advertisement

Topics in Catalysis

, Volume 27, Issue 1–4, pp 105–117 | Cite as

Solid Catalysts for the Synthesis of Fatty Esters of Glycerol, Polyglycerols and Sorbitol from Renewable Resources

  • Carlos Márquez-Alvarez
  • Enrique Sastre
  • Joaquín Pérez-Pariente
Article

Abstract

Partial esters of polyols such as glycerol, polyglycerols and sorbitol are nonionic surfactants used as emulsifiers in the food, detergents and cosmetics industries. The commercial large-scale production of these chemicals relies on traditional homogeneous catalysis processes making use of strong mineral acids or alkalis. This technology possesses severe drawbacks, related to the generation of large amounts of by-products, high energy demand, and heterogeneity of the ester mixtures obtained. The development of new processes based on more selective solid catalysts has, therefore, a great economical interest. This contribution reviews the scientific and technical literature in this field. It is proposed that solid catalysts based on MCM-41 and other mesostructures could give rise to the development of new, more efficient processes for the large-scale synthesis of fatty acid esters of polyols.

fatty acid esters polyols monoglycerides sorbitol polyglycerol nonionic surfactants emulsifiers heterogeneous catalysts zeolites mesoporous catalysts esterification transesterification glycerolysis 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. [1]
    W.C. Griffin, J. Soc. Cosmetic Chem. 1 (1949) 311.Google Scholar
  2. [2]
    G. Dieckelmann and H.J. Heinz, The Basics of Industrial Oleochemistry (Petr Pomp, Essen, 1988).Google Scholar
  3. [3]
    U.T. Bornscheuer, Enzyme Microb. Technol. 17 (1995) 578.Google Scholar
  4. [4]
    F.J. Plou, M. Barandiaran, M.V. Calvo, A. Ballesteros and E. Pastor, Enzyme Microb. Technol. 18 (1996) 66.Google Scholar
  5. [5]
    C. Otero, J.A. Arcos, M.A. Berrendero and C. Torres, J. Mol. Catal. B 11 (2001) 883.Google Scholar
  6. [6]
    W. Tsuzuki, Y. Kitamura, T. Suzuki and S. Kobayashi, Biotechnol. Bioeng. 64 (1999) 267.PubMedGoogle Scholar
  7. [7]
    D. Charlemagne and M.D. Legoy, J. Am. Oil Chem. Soc. 72 (1995) 61.Google Scholar
  8. [8]
    A. Brock, B. Grüning and G. Hills, European Patent Appl. EP 1250917 (2003).Google Scholar
  9. [9]
    N.O.V. Sonntag, J. Am. Oil Chem. Soc. 59 (1982) 795A.Google Scholar
  10. [10]
    A. Corma, S. Iborra, S. Miquel and J. Primo, J. Catal. 173 (1998) 315.Google Scholar
  11. [11]
    S. Bancquart, C. Vanhove, Y. Pouilloux and J. Barrault, Appl. Catal. A 218 (2001) 1.Google Scholar
  12. [12]
    A. Corma, H. García, S. Iborra and J. Primo, J. Catal. 120 (1989) 78.Google Scholar
  13. [13]
    S. Abro, Y. Pouilloux and J. Barrault, Stud. Surf. Sci. Catal. 108 (1997) 539.Google Scholar
  14. [14]
    I. Díaz, A. Martínez-Guerenu, F. Mohíno, J. Pérez-Pariente and E. Sastre, Actas do XVII Simpósio Ibero-americano de Catálise (FEUP, Porto, 2000) p. 559.Google Scholar
  15. [15]
    N. Sánchez, M. Martínez and J. Aracil, Ind. Eng. Chem. Res. 36 (1997) 1524.Google Scholar
  16. [16]
    E. Heykants, W.H. Verrelst, R.F. Parton and P.A. Jacobs, Stud. Surf. Sci. Catal. 105 (1997) 1277.Google Scholar
  17. [17]
    M. da Silva-Machado, J. Pérez-Pariente, E. Sastre, D. Cardoso and A. Martínez-Guereñu, Appl. Catal. A 203 (2000) 321.Google Scholar
  18. [18]
    M. da Silva-Machado, D. Cardoso and J. Pérez-Pariente, Stud. Surf. Sci. Catal. 130 (2000) 3417.Google Scholar
  19. [19]
    Y. Pouilloux, S. Abro, C. Vanhove and J. Barrault, J. Mol. Catal. A 149 (1999) 243.Google Scholar
  20. [20]
    A. Corma, V. Fornés, M.T. Navarro and J. Pérez-Pariente, J. Catal. 148 (1994) 569.Google Scholar
  21. [21]
    J. Pérez-Pariente, I. Díaz, F. Mohíno and E. Sastre, Appl. Catal. A in press.Google Scholar
  22. [22]
    W.D. Bossaert, D.E. de Vos, W.M. Van Rhijn, J. Bullen, P.J. Grobet and P.A. Jacobs, J. Catal. 182 (1999) 156.Google Scholar
  23. [23]
    I. Díaz, F. Mohíno, J. Pérez-Pariente and E. Sastre, Appl. Catal. A 205 (2001) 19.Google Scholar
  24. [24]
    I. Díaz, C. Márquez-Alvarez, F. Mohíno, J. Pérez-Pariente and E. Sastre, Microporous Mesoporous Mater. 44–45 (2001) 295.Google Scholar
  25. [25]
    I. Díaz, C. Márquez-Alvarez, F. Mohíno, J. Pérez-Pariente and E. Sastre, J. Catal. 193 (2000) 283.Google Scholar
  26. [26]
    I. Díaz, C. Márquez-Alvarez, F. Mohíno, J. Pérez-Pariente and E. Sastre, J. Catal. 193 (2000) 295.Google Scholar
  27. [27]
    F. Mohíno, I. Díaz, J. Pérez-Pariente and E. Sastre, Stud. Surf. Sci. Catal. 142 (2002) 1275.Google Scholar
  28. [28]
    I. Díaz, F. Mohíno, J. Pérez-Pariente and E. Sastre, Appl. Catal. A 242 (2003) 161.Google Scholar
  29. [29]
    I. Díaz, F. Mohíno, M.T. Blasco, E. Sastre and J. Pérez-Pariente, 4th International Mesostructured Materials Symposium, submitted.Google Scholar
  30. [30]
    K. Wilson, A.F. Lee, D.J. Macquarrie and J.H. Clark, Appl. Catal. A 228 (2002) 151.Google Scholar
  31. [31]
    M. Boveri, J. Agúndez, I. Díaz, J. Pérez-Pariente and E. Sastre, Actas de la Reunión de la SECAT (Málaga-Torremolinos, 2003).Google Scholar
  32. [32]
    I. Díaz, F. Mohíno, E. Sastre and J. Pérez-Pariente, Stud. Surf. Sci. Catal. 135 (2001) 1383.Google Scholar
  33. [33]
    Y. Sakamoto, I. Díaz, O. Terasaki, D. Zhao, J. Pérez-Pariente, J.M. Kim and G.D. Stucky, J. Phys. Chem. B 106 (2002) 3118.Google Scholar
  34. [34]
    I. Díaz, F. Mohíno, J. Pérez-Pariente, E. Sastre, P.A. Wright and W. Zhou, Stud. Surf. Sci. Catal. 135 (2001) 1248.Google Scholar
  35. [35]
    A. Cauvel, G. Renard and D. Brunel, J. Org. Chem. 62 (1997) 749.PubMedGoogle Scholar
  36. [36]
    X. Lin, G.K. Chuah and S. Jaenicke, J. Mol. Catal. A 150 (1999) 287.Google Scholar
  37. [37]
    N. Garti, A. Aserin and B. Zaidman, J. Am. Oil Chem. Soc. 58 (1981) 878.Google Scholar
  38. [38]
    E. Symmes, U.S. Patent Appl. U.S. 1,696,337 (1928).Google Scholar
  39. [39]
    H.A. Bruson, U.S. Patent Appl. U.S. 2,284,127 (1942).Google Scholar
  40. [40]
    K. Babayan, U.S. Patent Appl. U.S. 3,637,774 (1972).Google Scholar
  41. [41]
    R.T. McIntyre, J. Am. Oil Chem. Soc. 56 (1979) 835A.Google Scholar
  42. [42]
    J. Van Heteren, P. Cornelis, F. Reckweg and M.F. Stewart, European Patent Appl. EP 0070080 (1983).Google Scholar
  43. [43]
    J. Klein, P. Daute, U. Hees and B. Beuer, PCT Int. Appl. WO 9302124 (1993).Google Scholar
  44. [44]
    G. Hillion and R. Stern, European Patent Appl. EP 0518765 (1992).Google Scholar
  45. [45]
    European Parliament and Council Directive No. 95/2/EC.Google Scholar
  46. [46]
    Code of Federal Regulation, Vol. 3, Title 21, Food and Drug Administration, US Government (2002).Google Scholar
  47. [47]
    H. Helfert, A. Hettche, S. Weiss, W.D. Balzer, W. Dietsche and G. Hatzmann, German Patent Appl. DE 3118417 (1982).Google Scholar
  48. [48]
    K.S. Dobson, K.D. Williams and C.J. Boriack, J. Am. Oil Chem. Soc. 70 (1993) 1089.Google Scholar
  49. [49]
    S. Akimoto, Japanese Patent Appl. JP58198429 (1983).Google Scholar
  50. [50]
    S. Uda and E. Takemoto, Japanese Patent Appl. JP61140534 (1986).Google Scholar
  51. [51]
    S. Uda and E. Takemoto, Japanese Patent Appl. JP61043627 (1986).Google Scholar
  52. [52]
    U. Hees, R. Bunte, J.W. Hachgenei, P. Kuhm and E.G. Harris, PCT Int. Appl. WO9325511 (1993).Google Scholar
  53. [53]
    K. Cottin, J.M. Clacens, Y. Pouilloux and J. Barrault, Ol. Corps Gras, Lipides 5 (1998) 407.Google Scholar
  54. [54]
    J.M. Clacens, Y. Pouilloux, J. Barrault, C. Linares and M. Goldwasser, Stud. Surf. Sci. Catal. 118 (1998) 895Google Scholar
  55. [55]
    J.M. Clacens, Y. Pouilloux and J. Barrault, Appl. Catal. A 227 (2002) 181.Google Scholar
  56. [56]
    T. Nakamura and M. Yamashita, U.S. Patent Appl. U.S. 2002/ 0035238 (2002).Google Scholar
  57. [57]
    N. Garti, G.F. Remon and B. Zaidman, Tenside Deterg. 23 (1986) 6.Google Scholar
  58. [58]
    S.B. Harvey, U.S. Patent Appl. U.S. 5,585,506 (1996).Google Scholar
  59. [59]
    D. Lemke, PCT Int. Appl. WO 0236534 (2002).Google Scholar
  60. [60]
    UK Patent Appl. GB1025265 (1966).Google Scholar
  61. [61]
    M. Ishitobi, U.S. Patent Appl. U.S. 2002/123439 (2002).Google Scholar
  62. [62]
    H. Tomokazu and Y. Akifumi, Japanese Patent Appl. JP 8217725 (1996).Google Scholar
  63. [63]
    P. Seiden and R.A. Woo, Patent Appl. CA 1185610 (1985).Google Scholar
  64. [64]
    B.K. Tjurin, German Patent Appl. DE 2511807 (1976).Google Scholar
  65. [65]
    K. Matsuda and M. Kitao, U.S. Patent Appl. U.S. 5,773,073 (1998).Google Scholar
  66. [66]
    G. Jakobson, W. Siemanowski and K.H. Uhlig, U.S. Patent Appl. U.S. 5,424,469 (1995).Google Scholar
  67. [67]
    P. Denecke, G. Börner and V. Von Allmen, UK Patent Appl. GB 2073232 (1981).Google Scholar
  68. [68]
    G. Jakobson, W. Siemanowski and K.H. Uhlig, U.S. Patent Appl. U.S. 5,466,719 (1995).Google Scholar
  69. [69]
    V.R. Kaufman and N. Garti, J. Am. Oil Chem. Soc. 59 (1982) 471.Google Scholar
  70. [70]
    I. Beseda and P.E. de Detrich, U.S. Patent Appl. U.S. 4,950,441 (1990).Google Scholar
  71. [71]
    V. Eychenne, L. Debrauwer and Z. Mouloungui, J. Surfact. Deterg. 3 (2000) 173.Google Scholar
  72. [72]
    E. Ulsperger, L. Richter and F. Mainas, Patent Appl. DD 41661 (1965).Google Scholar
  73. [73]
    T. Endo and T. Daito, European Patent Appl. EP0758641 (1997).Google Scholar
  74. [74]
    T. Endo and K. Maruo, Japanese Patent Appl. JP 2000143794 (2000).Google Scholar
  75. [75]
    T. Endo and T. Ueno, Japanese Patent Appl. JP 2000143584 (2000).Google Scholar
  76. [76]
    K. Maruo and H. Omori, Japanese Patent Appl. JP 11222521 (1999).Google Scholar
  77. [77]
    G. Vanlerberghe and H. Sebag, U.S. Patent Appl. U.S. 4,515,775 (1985).Google Scholar
  78. [78]
    K.R. Brown, U.S. Patent Appl. U.S. 2,322,820 (1943).Google Scholar
  79. [79]
    L.D. D'Hinterland, G. Mouzin and H. Cousse, French Patent Appl. FR 2176487 (1973).Google Scholar
  80. [80]
    G.J. Stockburger, U.S. Patent Appl. U.S. 4,297,290 (1981).Google Scholar
  81. [81]
    T. Masuda, M. Honjiyou and K. Watanabe, Japanese Patent Appl. JP 57133197 (1982).Google Scholar
  82. [82]
    S. Ropuszynski and E. Sczesna, Tenside Deterg. 22 (1985) 190.Google Scholar
  83. [83]
    N. Milstein, PCT Int. Appl. WO 9200947 (1992).Google Scholar
  84. [84]
    G.O. Gruetzmacher, J.W. Raggon and B. Wlodecki, U.S. Patent Appl. U.S. 5,612,080 (1997).Google Scholar
  85. [85]
    W.M. Van Rhijn, D.E. De Vos, B.F. Sels, W.D. Bossaert and P.A. Jacobs, Chem. Commun. (1998) 317.Google Scholar
  86. [86]
    J.M.H. Ellis, J.J. Lewis and R.J. Beattie, PCT Int. Appl. WO 9804540 (1998).Google Scholar
  87. [87]
    PCT Int. Appl. WO 0128961 (2001).Google Scholar
  88. [88]
    L. Szotyori, A. Ujhidy, I. Szabo, G. Bozoki and J. Bathory, Hungarian Patent Appl. HU 5159 (1972).Google Scholar
  89. [89]
    R.V. Vladea, M.A. Vineze, T.L. Simandan, L.M. Rusnac, A.T. Fenesiu and M. Mosincat, Romanian Patent Appl. RO 87381 (1985).Google Scholar
  90. [90]
    H. Luitjes and J.C. Jansen, PCT Int. Appl. WO 9945060 (1999).Google Scholar
  91. [91]
    A. Velty, Ph.D. Thesis (Universidad Politécnica de Valencia, 2003).Google Scholar

Copyright information

© Plenum Publishing Corporation 2004

Authors and Affiliations

  • Carlos Márquez-Alvarez
    • 1
  • Enrique Sastre
    • 1
  • Joaquín Pérez-Pariente
    • 1
  1. 1.Instituto de Catálisis y Petroleoquímica, CSICMadridSpain

Personalised recommendations