Esterification and transesterification of renewable chemicals

Topics in Catalysis

Volumn 27, Issue 1-4, 2004, Pages 83-96

  Hoydonckx, Hans E ^a   De Vos, Dirk E ^a   Chavan, Suhas A ^a   Jacobs, Pierre A ^a  

^a Centre for Surface Chemistry and Catalysis   (Belgium)

Author keywords

Acid catalyzed esterification; Ester exchange; Esterification

Indexed keywords

CATALYSTS; ESTERIFICATION; ESTERS; TRANSESTERIFICATION;

BASE CATALYST; ESTER EXCHANGE; INTERCHANGE REACTIONS; RENEWABLE CHEMICALS; RENEWABLE RESOURCE;

OILS AND FATS;

EID: 3543078712     PISSN: 10225528     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:TOCA.0000013543.96438.1a     Document Type: Article

References (178)

1. Ullmann's Encyclopedia of Technical Chemistry, 6th ed. Electronic release (Wiley-VCH, 2000);
2. Y.H. Hui (ed.) Bailey's Industrial Oil & Fat Products (Wiley-Interscience, New York, 1996).
3. A.L. Ayyagari, V. Penumarthy and N.B. Thengumpillil, U.S. 6,500,974 (2002).
4. L.J. Karas, U.S. 6,242,640 (2001).
5. M. Zirnstein, G.H. Grosch, E. Bohres, A. Oftring, S. Birnbach, W. Bochnitschek, O. Borzyk, R. Corell, H. Würz, T. Heidemann and M. Sigl, WO 02/081423 (2002).
6. J. Otera, Angew. Chem. 113 (2001) 2099.
7. K. Wakasugi, T. Misaki, K. Yamada and Y. Tanabe, Tetrahedron Lett. 41 (2000) 5249.
8. W.W. Lowrance, Tetrahedron Lett. 37 (1971) 3453.
9. K. Ishihara, S. Ohara and H. Yamamoto, J. Org. Chem. 61 (1996) 4196.
10. K. Manabe, S. Iimura, X. Sun and S. Kobayashi, J. Am. Chem. Soc. 124 (2002) 11971.
11. P.K. Kadaba, Synthesis (1972) 628.
12. A.C. Currie, EP 0037172 (1981).
13. H. Dalibor, DE 1185611 (1965).
14. L. Thil, B. Breitscheidel, W. Disteldorf, K. Dornik and B. Morsbach, DE 19924339 (2000).
15. W. Disteldorf, C. Übler, B. Morsbach, J. Peters, G. Golfier, DE 10128306 (2002).
16. A.K. Kumar and T.K. Chattopadhyay, Tetrahedron Lett. 28 (1987) 3713.
17. J. Otera, N. Dan-oh and H. Nozaki, J. Org. Chem. 56 (1991) 5307.
18. K. Steliou, A. Szczygielska-Nowosielska, A. Favre, M.A. Poupart, S. Hanessian, J. Am. Chem. Soc. 102 (1980) 7578.
19. J. Xiang, A. Orita and J. Otera, Angew. Chem. 114 (2002) 4291.
20. K. Ishihara, S. Ohara and H. Yamamoto, Science 290 (2000) 1140.
21. K. Ishihara, M. Nakayama, S. Ohara and H. Yamamoto, Synlett (2001) 1117.
22. K. Ishihara, M. Nakayama, S. Ohara and H. Yamamoto, Tetrahedron 58 (2002) 8179.
23. R.N. Ram and I. Charles, Tetrahedron 53 (1997) 7335.
24. T. Ogawa, T. Hikasa, T. Ikegami, N. Ono and H. Suzuki, J. Chem. Soc., Perkin Trans. 1 (1994) 3473.
25. S. Chandrasekhar, S.S. Sultana, Ch. Narsihmulu, J.S. Yadav, R. Gree and J.C. Guillemin, Tetrahedron Lett. 43 (2002) 8335.
26. N. Iranpoor and M. Shekarriz, Bull. Chem. Soc. Jpn. 72 (1999) 455.
27. A. Corma, H. Garcia, S. Iborra and J. Primo, J. Catal. 120 (1989) 78.
28. J. Aracil, M. Martinez, N. Sanchez and A. Corma, Zeolites 12 (1992) 233.
29. N. Sanchez, M. Martinez, J. Aracil and A. Corma, J. Am. Oil Chem. Soc. 69 (1992) 1150.
30. E. Heykants, W.H. Verrelst, R.F. Parton and P.A. Jacobs, Stud. Surf. Sci. Catal. 105 (1997) 1277.
31. W. Van Rhijn, D.E. De Vos, B.F. Sels, W.D. Bossaert and P.A. Jacobs, Chem. Commun. (1999) 317.
32. W.D. Bossaert, D.E. De Vos, W. Van Rhijn, J. Bullen, P.J. Grobet and P.A. Jacobs, J. Catal. 182 (1999) 156.
33. I. Diaz, F. Mohino, J. Perez-Pariente and E. Sastre, Appl. Catal. A 242 (2003) 161.
34. T. Okuhara, M. Kimura, T. Kawai, Z. Xu and T. Nakato, Catal. Today 45 (1998) 73.
35. T. Okuhara, Chem. Rev. 102 (2002) 3641.
36. M. Hino and K. Arata, Chem. Lett. (1981) 1671.
37. G.A. Olah, T. Keumi and D. Meidar, Synthesis (1978) 929.
38. Y. Izumi and K. Urabe, Chem. Lett. (1981) 663.
39. A. Takagaki, M. Sugisawa, D. Lu, J.N. Kondo, M. Hara, K. Domen and S. Hayashi, J. Am. Chem. Soc. 125 (2003) 5479.
40. J. Bertin, H.B. Kagan, J.-L. Luche and R. Setton, J. Am. Chem. Soc. 96 (1974) 8113.
41. B. Das, B. Venkataiah and P. Madhusudhan, Synlett (2000) 59.
42. H. Dalibor, DE 1173473 (1964).
43. K. Schmitt, W. Flakus and J. Disteldorf, DE 1593503 (1969).
44. Z. Chen, T. Iizuka and K. Tanabe, Chem. Lett. (1984) 1085.
45. S. Storck, W.F. Maier, I.M. Salvado, J.M. Ferreira, D. Guhl, W. Souverijns and J.A. Martens, J. Catal. 172 (1997) 414.
46. A.B. Gainer and L.E. McMakin, DE 1618639 (1971).
47. T. Mimura, J. Kaita, N. Fukuoka and Y. Hattori, DE 10033951 (2001).
48. F. List and K. Wember, DE 2243240 (1974).
49. E.C. Blossey, L.M. Turner and D.C. Neckers, Tetrahedron Lett. 21 (1973) 1823.
50. J. Otera, Chem. Rev. 93 (1993) 1449.
51. P. Ilankumaran and G. Verkade, J. Org. Chem. 64 (1999) 3086.
52. D.P. Roelofsen, J.W.M. De Graaf, J.A. Hagendoorn, H.M. Verschoor and H. van Bekkum, Recl. Trav. Chim. Pays-Bas 89 (1970) 193.
53. M.G. Stanton and M.R. Gagné, J. Org. Chem. 62 (1997) 8240.
54. M.G. Stanton, C.B. Allen, R.M. Kissling, A.L. Lincoln and M.R. Gagné, J. Am. Chem. Soc. 120 (1998) 5981.
55. J.H. Haslam, U.S. 2,822,348 (1958).
56. D. Seebach, E. Hungerbühler, R. Naef, D. Schnurrenberger, B. Weidmann and M. Züger, Synthesis (1982) 138.
57. P. Krasik, Tetrahedron Lett. 39 (1998) 4223.
58. G. Shapiro and M. Marzi, J. Org. Chem. 62 (1997) 7096.
59. H. Fincke, H. Bohr and S. Staeger, DE 1292140 (1966).
60. H. Ruschke and K. Grentzenberg, DE 1005947 (1957).
61. P. Baumhof, R. Mazitschek and A. Giannis, Angew. Chem. 113 (2001) 3784.
62. R.L.E. Furlan, E.G. Mata and O.A. Mascaretti, Tetrahedron Lett. 39 (1998) 2257.
63. J. Otera, S. Ioka and H. Nozaki, J. Org. Chem. 54 (1989) 4013.
64. A. Orita, A. Mitsutome and J. Otera, J. Org. Chem. 63 (1998) 2420.
65. A. Orita, K. Sakamoto, Y. Hamada, A. Mitsutome and J. Otera, Tetrahedron 55 (1999) 2899.
66. J. Xiang, S. Toyoshima, A. Orita and J. Otera, Angew. Chem. 113 (2001) 3782.
67. R.H. Stanley, D.W. Brook and V. Prenna, DE 1807103 (1969).
68. D. Tashiro, Y. Kawasaki, S. Sakaguchi and Y. Ishii, J. Org. Chem. 62 (1997) 8141.
69. B.C. Ranu, P. Dutta and A. Sarkar, J. Org. Chem. 63 (1998) 6027.
70. B.S. Balaji, M. Sasidharan, R. Kumar and B. Chanda, Chem. Commun. (1996) 707.
71. D.E. Ponde, V.H. Deshpande, V.J. Bulbule, A. Sudalai and A.S. Gajare, J. Org. Chem. 63 (1998) 1058.
72. S.P. Chavan, P.K. Zubaidha, S.W. Dantale, A. Keshavaraja, A.V. Ramaswamy and T. Ravindranathan, Tetrahedron Lett. 37 (1996) 233.
73. Y.V.S. Rao, D.E. De Vos and P.A. Jacobs, Angew. Chem., Int. Ed. Engl. 36 (1997) 2661.
74. F. Ma and M.A. Hanna, Bioresour. Technol. 70 (1999) 1.
75. A. Demirbas, Energy Convers. Manage. 44 (2003) 2093.
76. H. Fukuda, A. Kondo and H. Noda, J. Biosci. Bioeng. 63 (1992) 405.
77. G. Kilidran, S.O. Yücel and S. Türkay, J. Am. Oil Chem. Soc. 73 (1996) 225.
78. S. Özgül and S. Türkay, J. Am. Oil Chem. Soc. 70 (1993) 145.
79. M. Diosakou, A. Louloudi and N. Papayannakos, Fuel 77 (1998) 1297.
80. A. Demirbas, Energy Convers. Manage. 43 (2002) 2349.
81. S. Saka and D. Kusdiana, Fuel 80 (2001) 225.
82. D. Kusdiana and S. Saka, Fuel 80 (2001) 693.
83. E. Leclerq, A. Finiels and C. Moreau, J. Am. Oil Chem. Soc. 78 (2001) 1161 .
84. R. Sercheli, R.M. Vargas and U. Schuchardt, J. Am. Oil Chem. Soc. 76 (1999) 1207.
85. S.K.F. Peter, R. Ganswindt, H.P. Neuner and E. Weidner, Eur. J. Lipid Sci. Technol. 104 (2002) 324.
86. Y. Shimada, Y. Watanabe, T. Samukawa, A. Sugihara, H. Noda, H. Fukuda and Y. Tominaga, J. Am. Oil Chem. Soc. 76 (1999) 789.
87. Y. Watanabe, Y. Shimada, T. Samukawa, A. Sugihara, H. Noda, H. Fukuda and Y. Tominaga, J. Am. Oil Chem. Soc. 77 (2000) 355.
88. T. Samukawa, M. Kaieda, T. Matsumoto, K. Ban, A. Kondo, Y. Shimada, H. Noda and H. Fukuda, J. Biosci. Bioeng. 90 (2000) 180.
89. M. Kaieda, T. Samukawa, A. Kondo and H. Fukuda, J. Biosci. Bioeng. 91 (2001) 12.
90. M.A. Jackson and J.W. King, J. Am. Oil Chem. Soc. 73 (1996) 353.
91. M.S. Machado, J. Perez-Pariente, E. Sastre, D. Cardoso, A.M. de Guerenu, Appl. Catal. A 203 (2000) 321.
92. N. Sanchez, M. Martinez and J. Aracil, Ind. Eng. Chem. Res. 36 (1997) 1524.
93. N. Sanchez, M. Martinez and J. Aracil, Ind. Eng. Chem. Res. 36 (1997) 1529.
94. S. Abro, Y. Pouilloux and J. Barrault, Stud. Surf. Sci. Catal. 108 (1997) 539.
95. Y. Pouilloux, S. Abro, C. Vanhove and J. Barrault, J. Mol. Catal. A 149 (1999) 243.
96. I. Diaz, C. Marquez-Alvarez, F. Mohino, J. Perez-Pariente and E. Sastre, J. Catal. 193 (2000) 295.
97. I. Diaz, F. Mohino, J. Perez-Pariente and E. Sastre, Appl. Catal. A 205 (2001) 19.
98. A. Corma, S. Iborra, S. Miquel and J. Primo, J. Catal. 173 (1998) 315.
99. S. Banquart, C. Vanhove, Y. Pouilloux and J. Barrault, Appl. Catal. A 218 (2001) 1.
100. J. Barrault, Y. Pouilloux, J.M. Clacens, C. Vanhove and S. Banquart, Catal. Today 75 (2002) 177.
101. A. Cauvel, G. Renard and D. Brunel, J. Org. Chem. 62 (1997) 749.
102. X. Lin, G.K. Chuah and S. Jaenicke, J. Mol. Catal. A 150 (1999) 287.
103. S. Jaenicke, G.K. Chuah, X.H. Lin and X.C. Hu, Microporous Mesoporous Mater. 35-36 (2000) 143.
104. M.A. Jackson and J.W. King, J. Am. Oil Chem. Soc. 74 (1997) 103.
105. A. Coteron, M. Martinez and J. Aracil, J. Am. Oil Chem. Soc. 75 (1998) 657.
106. I. Elfman-Börjesson and M. Härröd, J. Am. Oil Chem. Soc. 76 (1999) 701.
107. X. Rendon, A. Lopez-Munguia and E. Castillo, J. Am. Oil Chem. Soc. 78 (2001) 1061.
108. W.F. Huber, GB 966541 (1964).
109. H. Sawada, N. Nishikawa and T. Kurosaki, DE 3729335 (1988).
110. G.J. Stockburger, U.S. 4,297,290 (1981).
111. J.M.H. Ellis, J.J. Lewis and J. Beattie, U.S. 6,362,353 (2002).
112. N. Milstein, WO 9200947 (1992).
113. J. Giacometti, C. Milin, N. Wolf and F. Giacometti, J. Agric. Food Chem. 44 (1996) 3950.
114. D. Van Es, A.E. Frissen and H. Luitjes, WO 0183488 (2001).
115. C. Limousin, J. Cléophax, A. Loupy and A. Petit, Tetrahedron 54 (1998) 13567.
116. C. Otero, J.A. Arcos, M.A. Berrendero and C. Torres, J. Mol. Catal. B 11 (2001) 883.
117. A.R.M. Yahya, W.A. Anderson and M. Moo-Young, Enzyme Microb. Technol. 23 (1998) 438.
118. F.W. Wagner, R.S. de la Motte and M.A. Dean, U.S. 4,927,920 (1990).
119. F.H. Mattson and R.A. Volpenhein, U.S. 3,954,976 (1976).
120. R.G. Schafermeyer, P.J. Corrigan, C.J. Kenneally and J.E. Trout, U.S. 5,767,257 (1998).
121. J.E. Trout and R.G. Schafermeyer, U.S. 6,504,003 (2003).
122. C.A. Crampton, F. Schild and R.J. Wicker, GB 890206 (1962).
123. W.A. Farone and R. Serfass, WO 06/40699 (1996).
124. R.A. Volpenhein, U.S. 4,517,360 (1985).
125. M.G. Buter, B. Barmentlo and U. Eiken, U.S. 5,580,966 (1996).
126. P.J. Corrigan, C.J. Kenneally and E.P. Granberg, U.S. 5,945,529 (1999).
127. L.I. Osipow and W. Rosenblatt, U.S. 3,644,333 (1972).
128. J. Kao, J.K. Howie, P.J. Corrigan, R.G. Schafermeyer, K.E. Flynn, N.J. Holzschuh and D.J. Bruno, U.S. 6,303,777 (2001).
129. R.S. Silver and G.L. Hasenhuettl, U.S. 5,596,085 (1997).
130. H. Seino, T. Uchibori, S. Inamasu and T. Nishitani, U.S. 4,614,718 (1986).
131. S. Soultani, J.-M. Engasser and M. Ghoul, J. Mol. Catal. B 11 (2001) 725.
132. R.T. Otto, H. Scheib, U.T. Bornscheuer, J. Pleiss, C. Syldatk and R.D. Schmid, J. Mol. Catal. B 8 (2000) 201.
133. Y. Yan, U.T. Bornscheuer, L. Cao and R.D. Schmid, Enzyme Microb. Technol. 25 (1999) 725.
134. A.T.J.W. de Goede, M. van Oosterom, M.P.J. van Deurzen, R.A. Sheldon, H. van Bekkum and F. van Rantwijk, Biocatalysis 9 (1994) 145.
135. M. Suchy, M. Zeller and P. Winternitz, WO 9100287 (1991).
136. K.T. Narayana, U.S. 6,342,626 (2002).
137. M. Alas, P. Redien and A. Bouniot, EP 0287426 (1988).
138. M.H.M. Arnold and C.G. Childs, GB 907322 (1958).
139. P. Walkup, C. Rohrmann, R. Hallen and D. Eakin, U.S. 5,252,473 (1993).
140. T.S. Wheeler and W.R.H. Hurtley, GB 346486 (1931).
141. K. Bodenbrenner, K. Hermann, G. Hochstadt and E. Junghanns, DE 3222837 (1983).
142. L.D. Brake, U.S. 5,264,617 (1993).
143. H. Satou, JP 61063637 (1986).
144. K. Bott, W Boehm, G. Fritz, C. Martin and H. Siegel, EP 0174624 (1985).
145. H.J. Sterzel, H. Vogel, H. Exner, D. Kratz and M. Bruder, U.S. 5,453,365 (1995).
146. C. Torres and C. Otero, Enzyme Microb. Technol. 25 (1999) 745.
147. K. Tanaka, R. Yoshikawa, C. Ying, H. Kita and K. Okamoto, Chem. Eng. Sci. (2002) 1577.
148. J. Jafar, P.M. Budd and R. Hughes, J. Membr. Sci. 199 (2002) 117.
149. H. Bohnen, K. Bergrath and T. Klein, U.S. 2002/0198402 A1 (2002).
150. K. Bergrath, T. Klein and H. Bohnen, U.S. 2002/0111508 A1 (2002).
151. T. Klein, H. Bohnen and Bergrath et al, DE 10133743 (2001).
152. E.H. Hull, DE 3520750 (1986).
153. A.G. Pereira, K.F. Gallagher, P.G. Abend and J.C. Carson Jr., U.S. 5,302,377 (1994).
154. L. Turchini, S. Garlisi and A. Albanini, EP 0199131 (1986).
155. P. Bernardi, D. Fornara and S. Garlisi, EP 0510564 (1992).
156. K. Stork, K. Oppenländer, K. Seib and P. Nägale, DE 2834645 (1980).
157. R. Bunte, H.C. Raths and R. Müller, DE 4025925 (1990).
158. F. Perron, T.C. Gahman and K.F. Albizati, Tetrahedron Lett. 29 (1988) 2023.
159. D.E. Ponde, V.H. Deshpande, V.J. Bulbule, A. Sudalai and A.S. Gajare, J. Org. Chem. 63 (1988) 1058.
160. P. Kumar and R.K. Pandey, Synlett 2 (2000) 251.
161. A. Orita, C. Tanahashi, A. Kakuda and J. Otera, Angew. Chem. 39 (2000) 2877.
162. Y. Nakae, I. Kusaki and T. Sato, Synlett 10 (2001) 1584.
163. P. Kumar, R.K. Pandey, M.S. Bodas, S.D. Dagade, M.K. Dongare and A.V. Ramaswamy, J. Mol. Catal. A 181 (2002) 207.
164. A. Orita, K. Sakamoto, Y. Hamada, A. Mitsutome and J. Otera, Tetrahedron 55 (1999) 2899.
165. A. Pelter and B. Singaram, J. Chem. Soc., Perkin Trans. (1983) 1383.
166. H. Buchold, F. Gaertner, G. Mallok, E. Schlichting and H. Stönner, U.S. 5,608,122.
167. D. Beuke, U.S. 4,659,514 (1987).
168. M.K. Karvo, U.S. 5,969,092 (1999).
169. W.R. Smith, U.S. 3,780,013 (1973).
170. R.W. Johnson, U.S. 4,962,186 (1990).
171. Y. Honma, F. Kawamoto and S. Tanaka, EP 0376075 (1990).
172. D. Gubisch, U. Ernst and W. Bueschken, U.S. 2002/0028963 (2002).
173. B.A. Salka, B.W. Gesslein and N. Milstein, WO 96/04987 (1996).
174. Y. Pouilloux, G. Courtois, M. Boisseau, A. Piccirilli and J. Barrault, Green Chem. 5 (2003) 89.
175. N. Milstein, M. Biermann, P. Leidl and R. von Kries, U.S. 6,394,230 (2002).
176. P. Nayler, GB 878680 (1961).
177. H. Pasedach, DE 1768980 (1971).
178. K. Bauer, D. Garbe and H. Surburg, Common Fragrance and Flavor Materials (Wiley-VCH, Weinheim, 1997).