Oxidation of reactive alcohols with hydrogen peroxide catalyzed by manganese complexes

Catalysis Letters

Volumn 138, Issue 3-4, 2010, Pages 193-204

  Shul'Pin, Georgiy B ^a   Kozlov, Yuriy N ^a   Shul'Pina, Lidia S ^b   Strelkova, Tatyana V ^b   Mandelli, Dalmo ^c  

^a SEMENOV INSTITUTE OF CHEMICAL PHYSICS   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c PONTIFÍCIA UNIVERSIDADE CATÓLICA DE CAMPINAS   (Brazil)

Author keywords

Alcohols; Glycerol; Heterogenized catalysts; Homogeneous catalysis; Manganese complexes; Renewables

Indexed keywords

1-PHENYLETHANOL; ACETONITRILE SOLUTIONS; ACETOPHENONES; ACTIVE SPECIES; DIHYDROXYACETONE; GLYCEROL OXIDATION; GLYCOLIC ACIDS; HETEROGENEOUS CATALYST; HETEROGENIZED CATALYSTS; HOMOGENEOUS CATALYSIS; HOMOGENEOUS SYSTEM; HYDROXYL RADICALS; INITIAL RATE; KINETIC STUDY; MANGANESE COMPLEXES; OXALIC ACID; OXIDATION OF GLYCEROL; OXIDIZING SPECIES; RENEWABLES; ROOM TEMPERATURE; SOLUBLE CATALYSTS; TRIAZACYCLONONANE; TRIMETHYL; TURNOVER NUMBER; YIELDS OF PRODUCTS;

ACETONITRILE; CATALYSIS; CATALYSTS; ETHANOL; GLYCEROL; HYDROGEN; HYDROGEN PEROXIDE; KETONES; LEACHING; MANGANESE; MANGANESE COMPOUNDS; METAL COMPLEXES; REACTION KINETICS;

CATALYTIC OXIDATION;

EID: 77956526855     PISSN: 1011372X     EISSN: 1572879X     Source Type: Journal    
DOI: 10.1007/s10562-010-0398-9     Document Type: Article

References (116)

1. Strukul G (ed) (1992) Catalytic oxidations with hydrogen peroxide as oxidant. Kluwer Academic Publishers, Dordrecht
2. J Muzart 2003 Tetrahedron 59 5789 5816
3. Marko IE, Giles PR, Tsukazaki M, Gautier A, Dumeunier R, Doda K, Philippart F, Chellé-Regnault I, Mutonkole J-L, Brown SM, Urch CJ (2004) Aerobic, metal-catalyzed oxidation of alcohols. In: Beller M, Bolm C (eds) Transition metals for organic synthesis, vol 2, 2nd edn. Wiley-VCH: Weinheim/New York, pp 437-478
4. T Mallat A Baiker 2004 Chem Rev 104 3037 3058
5. Tojo G, Fernandez M (2006) Oxidation of alcohols to aldehydes and ketones. Springer Science, Business Media, Inc, New York
6. T Seki A Baiker 2009 Chem Rev 109 2409 2454
7. L Prati F Porta 2005 Appl Catal A: General 291 199 203
8. P Korovchenko C Donze P Gallezot M Besson 2007 Catal Today 121 13 21
9. PJ Figiel AM Kirillov YY Karabach MN Kopylovich AJL Pombeiro 2009 J Mol Catal A: Chem 305 178 182
10. N Jiang D Vinci CL Liotta CA Eckert AJ Ragauskas 2008 Ind Eng Chem Res 47 627 631
11. P Haider J-D Grunwaldt A Baiker 2009 Catal Today 141 349 354
12. PJ Figiel JM Sobczak 2009 J Catal 263 167 172
13. BM Pérez J Hartung 2009 Tetrahedron Lett 50 960 962
14. A Villa N Janjic P Spontoni D Wang DS Su L Prati 2009 Appl Catal A: General 364 221 228
15. V Lecomte C Bolm 2005 Adv Synth Catal 347 1666 1672
16. F Shi MK Tse M-M Pohl J Radnik A Brückner S Zhang M Beller 2008 J Mol Catal A: Chem 292 28 35
17. T Hida H Nogusa 2009 Tetrahedron 65 270 274
18. Z Ye Z Fu S Zhong F Xie X Zhou F Liu D Yin 2009 J Catal 261 110 115
19. Z Lounis A Riahi F Djafri J Muzart 2006 Appl Catal A: General 309 270 272
20. A Tarlani A Riahi M Abedini MM Amini J Muzart 2006 Appl Catal A: General 315 150 152
21. C Della Pina E Falletta M Rossi 2008 J Catal 260 384 386
22. P Haider B Kimmerle F Krumeich S Kleist J-D Grunwaldt A Baiker 2008 Catal Lett 125 169 176
23. S Xu X Yan Y Yao X He Y Chen 2009 Shiyou Huagong (Petrochemical Technology) 38 193 196
24. N Dimitratos JA Lopez-Sanchez D Morgan AF Carley R Tiruvalam CJ Kiely D Bethell GJ Hutchings 2009 Phys Chem Chem Phys 11 5142 5153
25. J Van Gerpen 2005 Fuel Process Technol 86 1097 1107
26. CRB da Silva VLC Gonçalves ER Lachter CJA Mota 2009 J Braz Chem Soc 20 201 204
27. SM de Rezende M de Castro Reis MG Reid PL Silva Jr FMB Coutinho RASS Gil ER Lachter 2008 Appl Catal A: General 349 198 203
28. Sels B, D'Hondt E, Jacobs P (2007) Catalytic transformation of glycerol. In: Centi G, van Santen RA (eds) Catalysis for renewables. Wiley-VCH Verlag, Weinheim, pp 223-255
29. A Corma S Iborra A Velty 2007 Chem Rev 107 2411 2502
30. C-H Zhou JN Beltramini Y-X Fan GQ Lu 2008 Chem Soc Rev 37 527 549
31. Y Zheng X Chen Y Shen 2008 Chem Rev 108 5253 5277
32. A Behr J Eilting K Irawadi J Leschinski F Lindner 2008 Green Chem 10 13 30
33. Pagliaro M, Rossi M (2008) The future of glycerol. New usages for a versatile raw material. RSC Publishing, Cambridge, p 128
34. A Behr 2008 ChemSusChem 1 653
35. R Garcia M Besson P Gallezot 1995 Appl Catal A: General 127 165 176
36. S Carrettin P McMorn P Johnston K Griffin CJ Kiely GJ Hutchings 2003 Phys Chem Chem Phys 5 1329 1336
37. CL Bianchi P Canton N Dimitratos F Porta L Prati 2005 Catal Today 102-103 203 212
38. N Dimitratos JA Lopez-Sanchez D Lennon F Porta L Prati A Villa 2006 Catal Lett 108 147 153
39. WC Ketchie M Murayama RJ Davis 2007 J Catal 250 264 273
40. E Taarning AT Madsen JM Marchetti K Egeblad CH Christensen 2008 Green Chem 10 408 414
41. V Maurino A Bedini M Minella F Rubertelli E Pelizetti C Minero 2008 J Adv Oxid Tech 11 184 192
42. SD Pollington DI Enache P Landon S Meenakshisundaram N Dimitratos A Wagland GJ Hutchings EH Stitt 2009 Catal Today 145 169 175
43. L Prati P Spontoni A Gaiassi 2009 Top Catal 52 288 296
44. JM Thomas JC Hernandez-Garrido RG Bell 2009 Top Catal 52 1630 1639
45. D Liang J Gao J Wang P Chen Z Hou X Zheng 2009 Catal Commun 10 1586 1590
46. N Dimitratos A Villa L Prati 2009 Catal Lett 133 334 340
47. DC Rennard JS Kruger LD Schmidt 2009 ChemSusChem 2 89 98
48. S Demirel-Gülen M Lucas P Claus 2005 Catal Today 102-103 166 172
49. S Demirel P Kern M Lucas P Claus 2007 Catal Today 122 292 300
50. S Demirel M Lucas J Wärnå T Salmi D Murzin P Claus 2007 Top Catal 44 299 305
51. AA Herzing CJ Kiely AF Carley P Landon GJ Hutchings 2008 Science 321 1331 1335
52. JA Lopez-Sanchez N Dimitratos P Miedziak E Ntainjua JK Edwards D Morgan AF Carley R Tiruvalam CJ Kiely GJ Hutchings 2008 Phys Chem Chem Phys 10 1921 1930
53. N Dimitratos JA Lopez-Sanchez JM Anthonykutty G Brett AF Carley RC Tiruvalam AA Herzing CJ Kiely DW Knight GJ Hutchings 2009 Phys Chem Chem Phys 11 4952 4961
54. N Dimitratos JA Lopez-Sanchez JM Anthonykutty G Brett AF Carley SH Taylor DW Knight GJ Hutchings 2009 Green Chem 11 1209 1216
55. LA Clejan AI Cederbaum 1992 FASEB J 6 765 770
56. J Rashba-Step E Step NJ Turro AI Cederbaum 1994 Biochemistry 33 9504 9510
57. S Liebminger M Siebenhofer G Guebitz 2009 Bioresour Technol 100 4541 4545
58. GP da Silva M Mack J Contiero 2009 Biotechnol Adv 27 30 39
59. R Bauer N Katsikis S Varga D Hekmat 2005 Bioprocess Biosyst Eng 28 37 43
60. P McMorn G Roberts GJ Hutchings 1999 Catal Lett 63 193 197
61. R Luque V Budarin JH Clark DJ Macquarrie 2008 Appl Catal B: Environ 82 157 162
62. M Sankar N Dimitratos DW Knight AF Carley R Tiruvalam CJ Kiely D Thomas GJ Hutchings 2009 ChemSusChem 2 1145 1151
63. VF Laurie AL Waterhouse 2006 J Agric Food Chem 54 4668 4673
64. N Dimitratos C Messi F Porta L Prati A Villa 2006 J Mol Catal A: Chem 256 21 28
65. H Kimura K Tsuto T Wakisaka Y Kazumi Y Inaya 1993 Appl Catal A: General 96 217 228
66. S Demirel K Lehnert M Lucas P Claus 2007 Appl Catal B: Environ 70 637 643
67. A Brandner K Lehnert A Bienholz M Luca P Claus 2009 Top Catal 52 278 287
68. Brandner A, Claus P (2009) 6th World congress on oxidation catalysis, Lille, France, report 3B-552
69. N Wörz A Brandner P Claus 2010 J Phys Chem C 114 1164 1172
70. GB Shul'pin JR Lindsay Smith 1998 Russ Chem Bull 47 2379 2386
71. GB Shul'pin G Süss-Fink JR Lindsay Smith 1999 Tetrahedron 55 5345 5358
72. GB Shul'pin G Süss-Fink LS Shul'pina 2001 J Mol Catal A: Chem 170 17 34
73. GB Shul'pin GV Nizova YN Kozlov IG Pechenkina 2002 New J Chem 26 1238 1245
74. CB Woitiski YN Kozlov D Mandelli GV Nizova U Schuchardt GB Shul'pin 2004 J Mol Catal A: Chem 222 103 119
75. GB Shul'pin GV Nizova YN Kozlov VS Arutyunov ACM dos Santos ACT Ferreira D Mandelli 2005 J Organometal Chem 690 4498 4504
76. D Mandelli RA Steffen GB Shul'pin 2006 React Kinet Catal Lett 88 165 174
77. VA dos Santos LS Shul'pina D Veghini D Mandelli GB Shul'pin 2006 React Kinet Catal Lett 88 339 348
78. GV Nizova GB Shul'pin 2007 Tetrahedron 63 7997 8001
79. GB Shul'pin MG Matthes VB Romakh MIF Barbosa JLT Aoyagi D Mandelli 2008 Tetrahedron 64 2143 2152
80. GB Shul'pin YN Kozlov SN Kholuiskaya MI Plieva 2009 J Mol Catal A: Chem 299 77 87
81. JR Lindsay Smith GB Shul'pin 1998 Tetrahedron Lett 39 4909 4912
82. GV Nizova C Bolm S Ceccarelli C Pavan GB Shul'pin 2002 Adv Synth Catal 344 899 905
83. Süss-Fink G, Shul'pin GB, Shul'pina LS (2002) Process for the production of ketones. U.S. Patent 7,015,358, March 21, 2006 (Filed 2002, to Lonza A.-G., Switzerland). Eur Patent EP 1 385812 A0 (Application: WO 02/088063, art. 158 of the EPC)
84. D Mandelli CB Woitiski U Schuchardt GB Shul'pin 2002 Chem Natur Comp 38 243 245
85. YN Kozlov D Mandelli CB Woitiski GB Shul'pin 2004 Russ J Phys Chem 78 370 374
86. VB Romakh B Therrien L Karmazin-Brelot G Labat H Stoeckli-Evans GB Shul'pin G Süss-Fink 2006 Inorg Chim Acta 359 1619 1626
87. VB Romakh B Therrien G Süss-Fink GB Shul'pin 2007 Inorg Chem 46 1315 1331
88. Shilov AE, Shul'pin GB (2000) Activation and catalytic reactions of saturated hydrocarbons in the presence of metal complexes. Dordrecht/Boston/ London, Kluwer Academic Publishers
89. GB Shul'pin 2002 J Mol Catal A: Chem 189 39 66
90. GB Shul'pin 2003 Comptes Rendus, Chimie 6 163 178
91. Shul'pin GB (2004) Oxidations of C-H compounds catalyzed by metal complexes. In: Beller M, Bolm C (eds) Transition metals for organic synthesis, vol 2, Chap 2.2, 2nd edn, Wiley-VCH: Weinheim/New York, pp 215-242
92. S Tanase E Bouwman 2006 Adv Inorg Chem 58 29 75
93. Sibbons KF, Shastri K, Watkinson M (2006) J Chem Soc Dalton Trans, 645-661
94. GB Shul'pin 2009 Mini-Rev Org Chem 6 95 104
95. GB Shul'pin 2001 Petrol Chem 41 405 412
96. YN Kozlov GV Nizova GB Shul'pin 2008 J Phys Org Chem 21 119 126
97. D Mandelli YN Kozlov CC Golfeto GB Shul'pin 2007 Catal Lett 118 22 29
98. D Veghini M Bosch F Fischer C Falco 2008 Catal Commun 10 347 350
99. Dorfman LM, Adams GE (1973) Reactivity of the hydroxyl radical in aqueous solutions, NSRDS-NBS 46, Washington DC
100. Farhataziz, Ross AB (1977) Selected specific rates of reactions of transients from water in aqueous solution. III. Hydroxyl radical and perhydroxyl radical and their radical ions. NSRDS-NBS 59, Washington DC
101. GB Shul'pin GV Nizova YN Kozlov L Gonzalez Cuervo G Süss-Fink 2004 Adv Synth Catal 346 317 332
102. Gómez L, Garcia-Bosch I, Company A, Sala X, Fontrodona X, Ribas X, Costas M (2007) Dalton Trans 5539-5545
103. WJ Song MS Seo SD George T Ohta R Song M-J Kang T Tosha T Kitagawa EI Solomon W Nam 2007 J Am Chem Soc 129 1268 1277
104. R Zhang M Newcomb 2008 Acc Chem Res 41 468 477
105. A Serafimidou A Stamatis M Louloudi 2008 Catal Commun 9 35 39
106. D Balcells C Raynaud RH Crabtree O Eisenstein 2008 Inorg Chem 47 10090 10099
107. E Ember S Rothbart R Puchta R van Eldik 2009 New J Chem 33 34 49
108. ST Castaman S Nakagaki RR Ribeiro KJ Ciuffi SM Drechsel 2009 J Mol Catal A: Chem 300 89 97
109. Bolm C, Meyer N, Raabe G, Weyhermüller T, Bothe E (2000) Chem Commun 2435-2436
110. BC Gilbert JR Lindsay Smith A Mairata i Payeras J Oakes R Pons i Prats 2004 J Mol Catal A: Chem 219 265 272
111. JR Lindsay Smith BC Gilbert A Mairata i Payeras J Murray TR Lowdon J Oakes R Pons i Prats PH Walton 2006 J Mol Catal A: Chem 251 114 122
112. Sameera WMC, McGrady JE (2008) Dalton Trans 6141-6149
113. H Kilic W Adam PL Alsters 2009 J Org Chem 74 1135 1140
114. A Stamatis P Doutsi C Vartzouma KC Christoforidis Y Deligiannakis M Louloudi 2009 J Mol Catal A: Chem 297 44 53
115. JR Lindsay Smith GB Shul'pin 1998 Russ. Chem. Bull. 47 2313 2315
116. MV Kirillova AM Kirillov D Mandelli WA Carvalho AJL Pombeiro GB Shul'pin 2010 J Catal 272 9 17