Glycerol and derived solvents: New sustainable reaction media for organic synthesis

Chemical Communications

Volumn 47, Issue 22, 2011, Pages 6208-6227

  Díaz Álvarez, Alba E ^a   Francos, Javier ^a   Lastra Barreira, Beatriz ^a   Crochet, Pascale ^a   Cadierno, Victorio ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; AMINOPOLYSACCHARIDE; BENZALDEHYDE; BIODIESEL; CARBON; CARBONIC ACID DERIVATIVE; CARBOXYLIC ACID; CITRAL; DEEP EUTECTIC SOLVENT; DIMETHYL SULFOXIDE; EPOXIDE; ESTER; ETHER DERIVATIVE; GLYCEROL; GLYCEROL DERIVATIVE; HYDROGEN; IONIC LIQUID; MACROGOL 400; NITROMETHANE; ORGANIC SOLVENT; OXYGEN; POLYSACCHARIDE; SODIUM BOROHYDRIDE; SOLVENT; THIOACETAL DERIVATIVE; THIOPHENOL; TOLUENE; TRANSITION ELEMENT; TRIACETIN; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; BIOCATALYSIS; BIODEGRADABILITY; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CULTURE MEDIUM; HECK REACTION; HYDROGEN BOND; HYDROGENATION; LIQUID; MICHAEL ADDITION; ORGANIC CHEMISTRY; PHYSICAL CHEMISTRY; POLYMERIZATION; REACTION TIME; RING CLOSING METATHESIS; RING OPENING; STOICHIOMETRY; SUZUKI REACTION; VISCOSITY;

EID: 79957496356     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c1cc10620a     Document Type: Article

References (173)

1. P. Kruger, Alternative Energy Resources: The Quest for Sustainable Energy, John Wiley & Sons, Hoboken, 2006
2. N. Armaroli V. Balzani Angew. Chem., Int. Ed. 2007 46 52
3. D. A. Coley, Energy and Climate Change Creating a Sustainable Future, John Wiley & Sons, Chichester, 2008
4. F. H. Cocks, Energy Demand and Climate: Change Issues and Resolutions, Wiley-VCH, Weinheim, 2009
5. W. H. Kemp, Biodiesel: Basics and Beyond, Azlext Press, Ontario, 2006
6. A. Demirbas, Biodiesel: A Realistic Fuel Alternative for Diesel Engines, Springer-Verlag, London, 2008
7. G. Pahl, Biodiesel: Growing a New Energy Economy, Chelsea Green Publishing, White River Junction, 2008
8. The Biodiesel Handbook, ed., G. Knothe,,, J. Krahl, and, J. Van Gerpen,, AOCS Publishing, Urbana, 2010
9. A. Hoogendoorn and H. van Kasteren, Transportation Biofuels Novel Pathways for the Production of Ethanol, Biogas and Biodiesel, RSC Publishing, Cambridge, 2010
10. C.-H. Zhou J. N. Beltramini Y.-X. Fan C. Q. Lu Chem. Soc. Rev. 2008 37 527
11. R. Palkovits K. Tajvidi A. M. Ruppert J. Procelewska Chem. Commun. 2011 47 576
12. M. Pagliaro and M. Rossi, The Future of Glycerol: New Usages for a Versatile Raw Material, RSC Publishing, Cambridge, 2008
13. M. Pagliaro R. Ciriminna H. Kimura M. Rossi C. D. Pina Angew. Chem., Int. Ed. 2007 46 4434
14. A. Corma S. Iborra A. Velty Chem. Rev. 2007 107 2411
15. D. T. Johnson K. A. Taconi Environ. Prog. 2007 26 338
16. A. Behr J. Eilting K. Irawadi J. Leschinski F. Lindner Green Chem. 2008 10 13
17. F. Jérôme Y. Pouilloux J. Barrault ChemSusChem 2008 1 586
18. G. P. da Silva M. Mack J. Conteiro Biotechnol. Adv. 2009 27 30
19. C. J. A. Mota C. X. A. da Silva V. L. C. Gonalves Quim. Nova 2009 32 639
20. M. Pagliaro R. Ciriminna H. Kimura M. Rossi C. D. Pina Eur. J. Lipid Sci. Technol. 2009 111 788
21. P. F. F. Amaral T. F. Ferreira G. C. Fontes M. A. Z. Coelho Food Bioprod. Process. 2009 87 179
22. P. D. Vaidya A. E. Rodrigues Chem. Eng. Technol. 2009 32 1463
23. S. Adhikari S. D. Fernando A. Haryanto Energy Convers. Manage. 2009 50 2600
24. N. Rahmat A. Z. Abdullah A. R. Mohamed Renewable Sustainable Energy Rev. 2010 14 987
25. P. T. Anastas, J. C. Warner, Green Chemistry Theory and Practice, Oxford University Press, Oxford, 1998
26. A. S. Matlack, Introduction to Green Chemistry, Marcel Dekker, New York, 2001
27. Handbook of Green Chemistry and Technology, ed., J. H. Clark, and, D. J. Macquarrie,, Blackwell Publishing, Abingdon, 2002
28. M. Lancaster, Green Chemistry: An Introductory Text, RSC Editions, Cambridge, 2002
29. M. Poliakoff J. M. Fitzpatrick T. R. Farren P. T. Anastas Science 2002 297 807
30. A. D. Curzons D. J. C. Constable D. N. Mortimer V. L. Cunningham Green Chem. 2001 3 1
31. J. M. DeSimone Science 2002 297 799
32. W. M. Nelson, Green Solvents for Chemistry: Perspectives and Practice, Oxford University Press, New York, 2003
33. J. H. Clark S. J. Taverner Org. Process Res. Dev. 2007 11 149
34. F. M. Kerton, Alternative Solvents for Green Chemistry, RSC Publishing, Cambridge, 2009
35. C. J. Li and T. H. Chan, in Comprehensive Organic Reactions in Aqueous Media, John Wiley & Sons, New Jersey, 2007
36. Organic Reactions in Water: Principles Strategies, and Applications, ed., U. M. Lindstrom,, Blackwell Publishing Ltd., Oxford, 2007
37. Aqueous-Phase Organometallic Catalysis: Concepts and Applications, ed., B. Cornils, and, W. A. Herrmann,, Wiley-VCH, Weinheim, 1998
38. F. Joó, Aqueous Organometallic Catalysis, Kluwer, Dordrecht, 2001
39. B. W. Cue J. Zhang Green Chem. Lett. Rev. 2009 2 193
40. Y. Gu F. Jérôme Green Chem. 2010 12 1127
41. Microwave Heating as a Tool for Sustainable Chemistry, ed., N. E. Leadbeater,, CRC Press, Boca Raton, 2011
42. Aqueous Microwave Assisted Chemistry, ed., V. Polshettiwar, and, R. S. Varma,, RSC Publishing, Cambridge, 2010
43. J. C. Thompson B. B. He Appl. Eng. Agric. 2006 22 621
44. L. Bournay D. Casanove B. Delfort G. Hillion J. A. Chodorge Catal. Today 2005 106 190
45. J. I. García H. García-Marín J. A. Mayoral P. Pérez Green Chem. 2010 12 426
46. P. Ferreira I. M. Fonseca A. M. Ramos J. Vital J. E. Castanheiro Catal. Commun. 2009 10 481
47. J. Deutsch A. Martin H. Lieske J. Catal. 2007 245 428
48. V. R. Ruiz A. Velty L. L. Santos A. Leyva-Pérez M. J. Sabater S. Iborra A. Corma J. Catal. 2010 271 351
49. T. Coleman and A. Blankenship, PCT Int. Appl., 2010, WO 2010/022263
50. Ger. Off., 1998, DE19648960 (BASF AG)
51. J. M. Fraile R. Mallada J. A. Mayoral M. Menéndez L. Roldán Chem.-Eur. J. 2010 16 3296
52. G. Vicente J. A. Melero G. Morales M. Paniagua E. Martín Green Chem. 2010 12 899
53. H. García, J. I. García, J. M. Fraile and J. A. Mayoral, Focus on Catalysis Applications (Supplement to Chimica Oggi vol. 26, no. 3), 2008, pp. 10-12
54. B. Schäffner F. Schäffner S. P. Verevkin A. Börner Chem. Rev. 2010 110 4554
55. C. Vieville J. W. Yoo S. Pelet M. Mouloungui Catal. Lett. 1998 56 245
56. M. Aresta A. Dibenedetto F. Nocito C. Pastore J. Mol. Catal. A: Chem. 2006 257 149
57. J. George Y. Patel S. M. Pillai M. Munshi J. Mol. Catal. A: Chem. 2009 304 1
58. J. Hu J. Li Y. Gu Z. Guan W. Mo Y. Ni T. Li G. Li Appl. Catal., A 2010 386 188
59. G. Rokicki P. Rakoczy P. Parzuchowski M. Sobieki Green Chem. 2005 7 529
60. S. C. Kim Y. H. Kim H. Lee D. Y. Yoon B. K. Song J. Mol. Catal. B: Enzym. 2007 49 75
61. K. S. Jung, J. H. Kim, J. H. Cho, D. K. Kim, PCT Int. Appl., 2009, WO 2009/035269
62. A. Behr P. Bahke B. Klinger M. Becker J. Mol. Catal. A: Chem. 2007 267 149
63. Handbook of Green Chemistry (Volume 6: Ionic Liquids), ed., P. Wasserscheid, and, A. Stark,, Wiley-VCH, Weinheim, 2010
64. Ionic Liquids in Synthesis, ed., P. Wasserscheid, and, T. Welton,, Wiley-VCH, Weinheim, 2008
65. Ionic Liquids in Organic Synthesis, ed., S. V. Malhotra,, ACS Symposium Series, Washington, 2007
66. P. J. Dyson and T. J. Geldbach, Metal Catalysed Reactions in Ionic Liquids, Springer, Dordrecht, 2005
67. P. J. Scammells J. L. Scott R. D. Singer Aust. J. Chem. 2005 58 155
68. S. Zhu R. Chen Y. Wu Q. Chen X. Zhang Z. Yub Chem. Biochem. Eng. Q. 2009 23 207
69. D. Coleman N. Gathergood Chem. Soc. Rev. 2010 39 600
70. T. P. Thuy Pham C.-W. Cho Y.-S. Yun Water Res. 2010 44 352
71. R. F. M. Frade C. A. M. Afonso Hum. Exp. Toxicol. 2010 29 1038
72. A. Ten Kate, M. J. J. Mayer, C. J. G. Van Strien, B. Kuzmanovic and C. A. M. C. Dirix, PCT Int. Appl., 2008, WO 2008/074733
73. F. Bellina A. Bertoli B. Melai F. Scalesse F. Signori C. Chiappe Green Chem. 2009 11 622
74. C. Chiappe F. Signori G. Valentini L. Marchetti C. S. Pomelli F. Bellina J. Phys. Chem. B 2010 114 5082
75. A. P. Abbott G. Capper D. L. Davies R. K. Rasheed V. Tambyrajah Chem. Commun. 2003 70
76. A. P. Abbott D. Boothby G. Capper D. L. Davies R. K. Rasheed J. Am. Chem. Soc. 2004 126 9142
77. J. Zhang T. Wu S. Chen P. Feng X. Bu Angew. Chem., Int. Ed. 2009 48 3486
78. A. P. Abbott P. M. Cullis M. J. Gibson R. C. Harris E. Raven Green Chem. 2007 9 868
79. A. P. Abbott R. C. Harris K. S. Ryder C. D'Agostino L. F. Gladden M. D. Mantle Green Chem. 2011 13 82
80. C. Reichardt Chem. Rev. 1994 94 2319
81. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, Wiley-VCH, Weinheim, 2003
82. B. Singh H. Lobo G. Shankarling Catal. Lett. 2011 141 178
83. S. B. Phadtare G. S. Shankarling Green Chem. 2010 12 458
84. Z. Chen W. Zhu Z. Zheng X. Zuo J. Fluorine Chem. 2010 131 340
85. Y. A. Sonawane S. B. Phadtare B. N. Borse A. R. Jagtap G. Shankarling Org. Lett. 2010 12 1456
86. A. Wolfson C. Dlugy Y. Shotland Environ. Chem. Lett. 2007 5 67
87. A. Wolfson C. Dlugy Org. Commun. 2009 2 34
88. Y. Gu J. Barrault F. Jérôme Adv. Synth. Catal. 2008 350 2007
89. P. M. Habib V. Kabala C.-W. Kuo C.-F. Yao Tetrahedron Lett. 2008 49 7005
90. A. Wolfson G. Litvak C. Dlugy Y. Shotland D. Tavor Ind. Crops Prod. 2009 30 78
91. E. J. Lenardão D. O. Trecha P. C. Ferreira R. G. Jacob G. Perin J. Braz. Chem. Soc. 2009 20 93
92. F. He P. Li Y. Gu G. Li Green Chem. 2009 11 1767
93. C. C. Silveira S. R. Mendes F. M. Líbero E. J. Lenardão G. Perin Tetrahedron Lett. 2009 50 6060
94. P. J. Kocienski, Protecting Groups, Thieme Verlag, Stuttgart, 3rd edn, 2003
95. T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley-Interscience, New York, 3rd edn, 1999
96. G. Perin L. G. Mello C. S. Radatz L. Savegnago D. Alves R. G. Jacob E. J. Lenardão Tetrahedron Lett. 2010 51 4354
97. See, for example: Multicomponent Reactions, ed., J. Zhu, and, H. Bienaymé,, Wiley-VCH, Weinheim, 2005
98. M. Li C. Chen F. He Y. Gu Adv. Synth. Catal. 2010 352 519
99. J.-N. Tan M. Li Y. Gu Green Chem. 2010 12 908
100. A. Karam N. Villandier M. Delample C. K. Koerkamp J.-P. Douliez R. Granet P. Krausz J. Barrault F. Jérôme Chem.-Eur. J. 2008 14 10196
101. S. Balieu A. El Zein R. De Sousa F. Jérôme A. Tatibouët S. Gatard Y. Pouilloux J. Barrault P. Rollin S. Bouquillon Adv. Synth. Catal. 2010 352 1826
102. D. Alves M. Sachini R. G. Jacob E. J. Lenardão M. E. Contreira L. Savegnago G. Perin Tetrahedron Lett. 2011 52 133
103. E. J. Lenardão M. S. Silva M. Sachini R. G. Lara R. G. Jacob G. Perin ARKIVOC 2009 11 221
104. C. Estévez, N. Bayarri, J. Castells and B. Echeverría, PCT Int. Appl., 2008, WO 2008/080601
105. C. Estévez, in Sustainable Solutions for Modern Economies, ed., R. Höfer,, RSC Publishing, Cambridge, 2009, pp. 407-424
106. H. García-Marín J. C. van der Toorn J. A. Mayoral J. I. García I. W. C. E. Arends Green Chem. 2009 11 1605
107. H. García-Marín J. C. van der Toorn J. A. Mayoral J. I. García I. W. C. E. Arends J. Mol. Catal. A: Chem. 2011 334 83
108. S. Murugesan R. J. Linhardt Curr. Org. Synth. 2005 2 437
109. O. A. El Seoud A. Koschella L. C. Fidale S. Dorn T. Heinze Biomacromolecules 2007 8 2629
110. V. Prasad R. R. Kale V. Kumar V. K. Tiwari Curr. Org. Synth. 2010 7 506
111. X. Tong Y. Ma Y. Li Appl. Catal., A 2010 385 1
112. K. D. O. Vigier F. Jérôme Top. Curr. Chem. 2010 295 63
113. M. Benoit Y. Brissonnet E. Guélou K. D. O. Vigier J. Barrault F. Jérôme ChemSusChem 2010 3 1304
114. A. Wolfson D. Saidkarimov C. Dlugy D. Tavor Green Chem. Lett. Rev. 2009 2 107
115. K. Tarama T. Funabiki Bull. Chem. Soc. Jpn. 1968 41 1744
116. T. Funabiki K. Tarama Bull. Chem. Soc. Jpn. 1971 44 945
117. A. Wolfson C. Dlugy Chem. Pap. 2007 61 228
118. S. B. Park H. Halper Org. Lett. 2003 5 3209
119. G. Zou W. Huang Y. Xiao J. Tang New J. Chem. 2006 30 803
120. M. Delample N. Villandier J.-P. Douliez S. Camy J.-S. Condoret Y. Pouilloux J. Barrault F. Jérôme Green Chem. 2010 12 804
121. L. Botella C. Najera J. Org. Chem. 2005 70 4360
122. S. P. Nolan H. Clavier Chem. Soc. Rev. 2010 39 3305
123. D. Burtscher K. Grela Angew. Chem., Int. Ed. 2009 48 442
124. N. Bakhrou F. Lamaty J. Martinez E. Colacino Tetrahedron Lett. 2010 51 3935
125. A. Behr G. Henze Green Chem. 2011 13 25
126. E. V. Spinacé J. M. Vaz Catal. Commun. 2003 4 91
127. L. Aldea J. M. Fraile H. García-Marín J. I. García C. I. Herrerías J. A. Mayoral I. Pérez Green Chem. 2010 12 435
128. J. S. M. Samec J.-E. Bäckvall P. G. Andersson P. Brandt Chem. Soc. Rev. 2006 35 237
129. T. Ikariya A. J. Blacker Acc. Chem. Res. 2007 40 1300
130. H. Adkins R. M. Elofson A. G. Rossow C. C. Robinson J. Am. Chem. Soc. 1949 71 3622
131. Dihydroxyacetone is used as a component in artificial tanning preparations in the cosmetic industry and as a valuable intermediate in biodegradable polymers synthesis. See, for example: K. Miltenberger, in Ullman's Encyclopedia Industrial Chemistry, ed., B. Elvers,,, S. Hawkins,,, M. Ravenscroft,,, J. F. Rounsaville, and, G. Schulz,, Wiley-VCH, Weinheim, 1989, vol. A13, p. 507
132. E. Farnetti J. Kapar C. Crotti Green Chem. 2009 11 704
133. C. Bianchini E. Farnetti M. Graziani G. Nardin A. Vacca F. Zanobini J. Am. Chem. Soc. 1990 112 9190
134. E. Farnetti N. V. Gulati M. Graziani Gazz. Chim. Ital. 1993 123 165
135. C. Crotti J. Kapar E. Farnetti Green Chem. 2010 12 1295
136. A. Wolfson C. Dlugy Y. Shotland D. Tavor Tetrahedron Lett. 2009 50 5951
137. D. Tavor O. Sheviev C. Dlugy A. Wolfson Can. J. Chem. 2010 88 305
138. D. Tavor S. Popov C. Dlugy A. Wolfson Org. Commun. 2010 3 70
139. Y. Shi W. Dayoub A. Favre-Réguillon G.-R. Chen M. Lemaire Tetrahedron Lett. 2009 50 6891
140. Y. Shi W. Daoub G.-C. Chen M. Lemaire Green Chem. 2010 12 2189
141. M. J. Climent A. Corma A. Veltry Appl. Catal., A 2004 263 155
142. G. Hillion, B. Delfort and I. Durand, PCT Int. Appl., 2005, WO 2005/093015
143. C. Crotti E. Farnetti N. Guidolin Green Chem. 2010 12 2225
144. S. F. Kirsch Org. Biomol. Chem. 2006 4 2076
145. D. M. D'Souza T. J. J. Müller Chem. Soc. Rev. 2007 36 1095
146. G. Balme D. Bouyssi N. Monteiro Heterocycles 2007 73 87
147. V. Cadierno P. Crochet Curr. Org. Synth. 2008 5 343
148. I. Özdemir B. Yiit B. etinkaya D. Ülkü M. N. Tahir C. Arici J. Organomet. Chem. 2001 633 27
149. A. E. Díaz-Álvarez P. Crochet M. Zablocka C. Duhayon V. Cadierno J. Gimeno J. P. Majoral Adv. Synth. Catal. 2006 348 1671
150. S. E. García-Garrido J. Francos V. Cadierno J.-M. Basset V. Polshettiwar ChemSusChem 2011 4 104
151. J. Francos V. Cadierno Green Chem. 2010 12 1552
152. B. Lastra-Barreira J. Francos P. Crochet V. Cadierno Green Chem. 2011 13 307
153. L. C. Gonaves G. F. Fiss G. Perin D. Alves R. G. Jacob E. J. Lenardão Tetrahedron Lett. 2010 51 6772
154. A. Debache W. Ghalem R. Boulcina A. Belfaitah S. Rhouati B. Carboni Tetrahedron Lett. 2009 50 5248
155. A. V. Narsaiah B. Nagaiah Asian J. Chem. 2010 22 8099
156. D. J. Pollard J. M. Woodley Trends Biotechnol. 2007 25 66
157. N. Ran L. Zhao Z. Chen J. Tao Green Chem. 2008 10 361
158. Modern Biocatalysis: Stereoselective and Environmentally Friendly Reactions, ed., W.-D. Fessner, and, T. Anthonsen,, Wiley-VCH, Weinheim, 2009
159. M. J. Hernáiz A. R. Alcántara J. I. García J. V. Sinisterra Chem.-Eur. J. 2010 16 9422
160. G. R. Castro T. Knubovets Crit. Rev. Biotechnol. 2003 23 195
161. S. Torres G. R. Castro Food Technol. Biotechnol. 2004 42 271
162. A. Wolfson C. Dugly D. Tavor J. Blumenfeld Y. Shotland Tetrahedron: Asymmetry 2006 17 2043
163. A. Wolfson N. Haddad C. Dlugy D. Tavor Y. Shotland Org. Commun. 2008 1 9
164. L. H. Andrade L. Piovan M. D. Pasquini Tetrahedron: Asymmetry 2009 20 1521
165. S. S. Yoo S. Park E. Y. Lee Biotechnol. Lett. 2008 30 1807
166. C. Dlugy A. Wolfson Bioprocess Biosyst. Eng. 2007 30 327
167. A. Wolfson A. Atyya C. Dlugy D. Tavor Bioprocess Biosyst. Eng. 2010 33 363
168. J. Gorke F. Srienc R. Kazlauskas Biotechnol. Bioprocess Eng. 2010 15 40
169. H. Zhao J. Chem. Technol. Biotechnol. 2010 85 891
170. J. T. Gorke F. Srienc R. J. Kazlauskas Chem. Commun. 2008 1235
171. J. T. Gorke, R. J. Kazlauskas and F. Srienc, U.S. Pat. Appl. US2009/0117628, 2009
172. J. T. Gorke, F. Srienc and R. J. Kazlauskas, in Ionic Liquid Applications: Pharmaceuticals Therapeutics and Biotechnology, (ACS Symposium Series vol. 1038), ed., S. V. Malhotra,, American Chemical Society, Washington, 2010, pp. 169-180
173. D. Lindberg M. de la Fuente Revenga M. Widersten J. Biotechnol. 2010 147 169