Highly efficient and selective transformations of glycerol using reusable heterogeneous catalysts

ACS Sustainable Chemistry and Engineering

Volumn 2, Issue 4, 2014, Pages 574-578

  Mizugaki, Tomoo ^a   Arundhathi, Racha ^a   Mitsudome, Takato ^a   Jitsukawa, Koichiro ^a   Kaneda, Kiyotomi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Acetylglycerols; Copper nanoparticles; Glycerol; Lanthanum exchanged montmorillonite; One pot reaction

Indexed keywords

ACETYLATION; CLAY MINERALS; LANTHANUM; METAL NANOPARTICLES;

ACETYLGLYCEROLS; COPPER NANOPARTICLES; HETEROGENEOUS CATALYST; HIGH ACTIVITY; ONE-POT REACTION; SELECTIVE SYNTHESIS; SELECTIVE TRANSFORMATION;

GLYCEROL;

EID: 84898012585     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc500006b     Document Type: Article

References (62)

1. Meher, L.; Vidyasagar, D.; Naik, S. Technical aspects of biodiesel production by transesterification: A review Renewable Sustainable Energy Rev. 2006, 10, 248-268
2. Dacquin, J.-P.; Lee, A. F.; Wilson, K. Heterogeneous Catalysts for Biodiesel Production. In Thermochemical Conversion of Biomass to Liquid Fuels and Chemicals; Crocker, M., Ed.; Royal Society of Chemistry: Cambridge, 2010; Chapter 16, pp 416-434, DOI: 10.1039/9781849732260-00416.
3. Gonçalves, K. M.; Sutili, F. K.; Júnior, I. I.; Flores, M. C.; Soter de Mariz e Miranda, L.; Leal, I. C. R.; Cordeiro, Y.; Luque, R.; de Souza, R. O. M. A. A comprehensive study on the activity and deactivation of immobilized Lecitase Ultra in esterifications of food waste streams to monoacylglycerols ChemSusChem 2013, 6, 872-879
4. Len, C.; Luque, R. Continuous flow transformations of glycerol to valuable products: An overview Sustainable Chem. Processes 2014, 2, 1 10.1186/2043-7129-2-1
5. Rahmat, N.; Abdullah, A. Z.; Mohamed, A. R. Recent progress on innovative and potential technologies for glycerol transformation into fuel additives: A critical review Renewable Sustainable Energy Rev. 2010, 14, 987-1000
6. Brandner, A.; Lehnert, K.; Bienholz, A.; Lucas, M.; Claus, P. Production of biomass-derived chemicals and energy: chemocatalytic conversions of glycerol Top. Catal. 2009, 52, 278-287
7. Zhou, C.-H. C.; Beltramini, J. N.; Fan, Y.-X.; Lu, G. Q. M. Chemoselective catalytic conversion of glycerol as a biorenewable source to valuable commodity chemicals Chem. Soc. Rev. 2008, 37, 527-549
8. Behr, A.; Eilting, J.; Irawadi, K.; Leschinski, J.; Lindner, F. Improved utilisation of renewable resources: New important derivatives of glycerol Green Chem. 2008, 10, 13-30
9. Huber, G. W.; Corma, A. Synergies between bio- and oil refineries for the production of fuels from biomass Angew. Chem., Int. Ed. 2007, 46, 7184-7201
10. Corma, A.; Iborra, S.; Velty, A. Chemical routes for the transformation of biomass into chemicals Chem. Rev. 2007, 107, 2411-2502
11. Huber, G. W.; Iborra, S.; Corma, A. Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering Chem. Rev. 2006, 106, 4044-4098
12. Ferreira, P.; Fonseca, I.; Ramos, A.; Vital, J.; Castanheiro, J. Esterification of glycerol with acetic acid over dodecamolybdophosphoric acid encaged in USY zeolite Catal. Commun. 2009, 10, 481-484
13. Gonçalves, V. L. C.; Pinto, B. P.; Silva, J. C.; Mota, C. J. A. Acetylation of glycerol catalyzed by different solid acids Catal. Today 2008, 133-135, 673-677
14. Liao, D.; Zhu, Y.; Wang, S.; Li, Y. Producing triacetylglycerol with glycerol by two steps: Esterification and acetylation Fuel Process. Technol. 2009, 90, 988-993
15. Luque, R.; Budarin, V.; Clark, J. H.; Macquarrie, D. J. Glycerol transformations on polysaccharide derived mesoporous materials Appl. Catal., B 2008, 82, 157-162
16. Melero, J. A.; Grieken, R.; Morales, G.; Paniagua, M. Acidic mesoporous silica for the acetylation of glycerol: Synthesis of bioadditives to petrol fuel Energy Fuels 2007, 21, 1782-1791
17. Melero, J. A.; Vicente, G.; Morales, G.; Paniagua, M.; Bustamante, J. Oxygenated compounds derived from glycerol for biodiesel formulation: Influence on EN 14214 quality parameters Fuel 2010, 89, 2011-2018
18. García, E.; Laca, M.; Perez, E.; Garrido, A.; Peinado, J. New class of acetal derived from glycerin as a biodiesel fuel component Energy Fuels 2008, 22, 4274-4280
19. Melero, J. A.; Iglesias, J.; Morales, G. Heterogeneous acid catalysts for biodiesel production: current status and future challenges Green Chem. 2009, 11, 1285-1308
20. Ferreira, P.; Fonseca, I. M.; Ramos, A. M.; Vital, J.; Castanheiro, J. E. Glycerol acetylation over dodecatungstophosphoric acid immobilized into a silica matrix as catalyst Appl. Catal., B 2009, 91, 416-422
21. Ferreira, P.; Fonseca, I. M.; Ramos, A. M.; Vital, J.; Castanheiro, J. E. Acetylation of glycerol over heteropolyacids supported on activated carbon Catal. Commun. 2011, 12, 573-576
22. Liao, X.; Zhu, Y.; Wang, S.-G.; Li, Y. Producing triacetylglycerol with glycerol by two steps: Esterification and acetylation Fuel Process. Technol. 2009, 90, 988-993
23. Smith, P. C.; Ngothai, Y.; Dzuy Nguyen, Q.; O'Neill, B. K. Improving the low-temperature properties of biodiesel: Methods and consequences Renewable Energy 2010, 35, 1145-1151
24. Rezayat, M.; Ghaziaskar, H. S. Continuous synthesis of glycerol acetates in supercritical carbon dioxide using Amberlyst 15 Green Chem. 2009, 11, 710-715
25. D'Alonzo, R. P.; Kozarek, W. J.; Wade, R. L. Glyceride composition of processed fats and oils as determined by glass capillary gas chromatography J. Am. Oil Chem. Soc. 1982, 59, 292-295
26. Haftendorn, R.; Ulbrich-Hofman, R. Synthesis of 2-modified 1,3-diacylglycerols Tetrahedron 1995, 51, 1177-1186
27. Nagata, J.; Saito, M. Effects of simultaneous intakes of indigestible dextrin and diacylglycerol on lipid profiles in rats fed cholesterol diets Nutrition 2006, 22, 395-400
28. Flickinger, B. D.; Matsuo, N. Nutritional characteristics of DAG oil Lipids 2003, 38, 129-132
29. Rosu, R.; Yasui, M.; Iwasaki, Y.; Yamane, T. Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system J. Am. Oil Chem. Soc. 1999, 76, 839-843
30. Berger, M.; Schneider, M. P. Enzymatic esterification of glycerol II. Lipase-catalyzed synthesis of regioisomerically pure 1(3)- rac -monoacylglycerols J. Am. Oil Chem. Soc. 1992, 69, 961-965
31. Watanabe, T.; Shimizu, M.; Sugiura, M.; Sato, M.; Kohori, J.; Yamada, N.; Nakanishi, K. Optimization of reaction conditions for the production of DAG using immobilized 1,3-regiospecific lipase lipozyme RM IM J. Am. Oil Chem. Soc. 2003, 80, 1201-1207
32. Watanabe, T.; Sugiura, M.; Sato, M.; Yamada, N.; Nakanishi, K. Diacylglycerol production in a packed bed bioreactor Process Biochem. 2005, 40, 637-643
33. Kaneda, K. Cation-exchanged montmorillonites as solid acid catalysts for organic synthesis Synlett 2007, 999-1015
34. Kaneda, K.; Motokura, K.; Nakagiri, N.; Mizugaki, T.; Jitsukawa, K. Recyclable indium catalysts for additions of 1,3-dicarbonyl compounds to unactivated alkynes affected by structure and acid strength of solid supports Green Chem. 2008, 10, 1231-1234
35. Motokura, K.; Nakagiri, N.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Nucleophilic substitution reactions of alcohols with use of montmorillonite catalysts as solid Brønsted acids J. Org. Chem. 2007, 72, 6006-6015
36. Kawabata, T.; Kato, M.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Monomeric metal aqua complexes in the interlayer space of montmorillonites as strong Lewis acid catalysts for heterogeneous carbon-carbon bond-forming reactions Chem.-Eur. J. 2005, 11, 288-297
37. Mitsudome, T.; Matsuno, T.; Sueoka, S.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Titanium cation-exchanged montmorillonite as an active heterogeneous catalyst for the Beckmann rearrangement under mild reaction conditions Tetrahedron Lett. 2012, 53, 5211-5214
38. Mitsudome, T.; Matsuno, T.; Sueoka, S.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Direct synthesis of unsymmetrical ethers from alcohols catalyzed by titanium cation-exchanged montmorillonite Green Chem. 2012, 14, 610-613
39. Ebitani, K.; Kawabata, T.; Nagashima, K.; Mizugaki, T.; Kaneda, K. Simple and clean synthesis of 9,9-bis[4-(2-hydroxyethoxy)phenyl]fluorene from the aromatic alkylation of phenoxyethanol with fluoren-9-one catalyzed by titanium cation-exchanged montmorillonite Green Chem. 2000, 2, 157-160
40. Mitsudome, T.; Nose, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Jitsukawa, K.; Kaneda, K. Montmorillonite-entrapped sub-nanoordered Pd clusters as a heterogeneous catalyst for allylic substitution reactions Angew. Chem., Int. Ed. 2007, 46, 3288-3290
41. Mitsudome, T.; Umetani, T.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Highly efficient Wacker oxidation catalyzed by heterogeneous Pd montmorillonite under acid-free conditions Tetrahedron Lett. 2006, 47, 1425-1428
42. 3 Chem. Mater. 2003, 15, 4830-4840
43. Mizugaki, T.; Arundhathi, R.; Mitsudome, T.; Jitsukawa, K.; Kaneda, K. Selective hydrogenolysis of glycerol to 1,2-propanediol using heterogeneous copper nanoparticle catalyst derived from Cu-Al hydrotalcite Chem. Lett. 2013, 42, 729-731
44. Balaraju, M.; Nikhitha, P.; Jagadeeswaraiah, K.; Srilatha, K.; Sai Prasad, P. S.; Lingaiah, N. Acetylation of glycerol to synthesize bioadditives over niobic acid supported tungstophosphoric acid catalysts Fuel Process. Technol. 2010, 91, 249-253
45. Jagadeeswaraiah, K.; Balaraju, M.; Prasad, P. S. S.; Lingaiah, N. Selective esterification of glycerol to bioadditives over heteropoly tungstate supported on Cs-containing zirconia catalysts Appl. Catal., A 2010, 386, 166-170
46. Frusteri, F.; Arena, F.; Bonura, G.; Cannilla, C.; Spadaro, L.; Di Blasi, O. Catalytic etherification of glycerol by tert-butyl alcohol to produce oxygenated additives for diesel fuel Appl. Catal., A 2009, 367, 77-83
47. Reddy, P. S.; Sudarsanam, P.; Raju, G.; Reddy, B. M. Synthesis of bio-additives: Acetylation of glycerol over zirconia-based solid acid catalysts Catal. Commun. 2010, 11, 1224-1228
48. Zhou, L.; Al-Zaini, E.; Adesina, A. A. Catalytic characteristics and parameters optimization of the glycerol acetylation over solid acid catalysts Fuel 2013, 103, 617-625
49. 3+ Acta Chem. Scand. 1961, 15, 1347-1366
50. Yasohara, Y.; Miyamoto, K.; Kizaki, N.; Hasegawa, J.; Ohashi, T. A practical chemoenzymatic synthesis of a key intermediate of antifungal agents Tetrahedron Lett. 2001, 42, 3331-3333
51. Blundell, P.; Ganguly, A.; Girijavallabhan, V. M. Synthesis of novel azole antifungals by a modified Sharpless asymmetric dihydroxylation Synlett 1994, 263-265
52. Chung, S. K.; Lee, K. W.; Kang, H. I.; Yamashita, C.; Kudo, M.; Yoshida, Y. Design and synthesis of potential inhibitors of the ergosterol biosynthesis as antifungal agents Bioorg. Med. Chem. 2008, 8, 2475-2486
53. Lovely, R. G.; Saksena, A. K.; Girijavallabhan, V. M. PPL-catalyzed enzymatic asymmetrization of a 2-substituted prochiral 1,3-diol with remote chiral functionality: improvements toward synthesis of the eutomers of SCH 45012 Tetrahedron Lett. 1994, 35, 6047-6050
54. Mitsudome, T.; Noujima, A.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Efficient aerobic oxidation of alcohols using a hydrotalcite-supported gold nanoparticle catalyst Adv. Synth. Catal. 2009, 351, 1890-1896
55. Mallat, T.; Baiker, A. Oxidation of alcohols with molecular oxygen on platinum metal catalysts in aqueous solutions Catal. Today 1994, 19, 247-284
56. Mori, K.; Hara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Hydroxyapatite-supported palladium nanoclusters: A highly active heterogeneous catalyst for selective oxidation of alcohols by use of molecular oxygen J. Am. Chem. Soc. 2004, 126, 10657-10666
57. Yamaguchi, K.; Mizuno, N. Supported ruthenium catalyst for the heterogeneous oxidation of alcohols with molecular oxygen Angew. Chem., Int. Ed. 2002, 41, 4538-4542
58. Wang, T.; Shou, H.; Kou, Y.; Liu, H. Base-free aqueous-phase oxidation of non-activated alcohols with molecular oxygen on soluble Pt nanoparticles Green Chem. 2009, 11, 562-568
59. 3 catalysts under microwave irradiation Appl. Catal., A 2008, 338, 9-13
60. Serdarevich, B. Glyceride isomerizations in lipid chemistry J. Am. Oil Chem. Soc. 1967, 44, 381-393
61. Mitsudome, T.; Mikami, Y.; Ebata, K.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Copper nanoparticles on hydrotalcite as a heterogeneous catalyst for oxidant-free dehydrogenation of alcohols Chem. Commun. 2008, 39, 4804-4806
62. Kawahara, R.; Fujita, K.; Yamaguchi, R. Cooperative catalysis by iridium complexes with a bipyridonate ligand: versatile dehydrogenative oxidation of alcohols and reversible dehydrogenation-hydrogenation between 2-propanol and acetone Angew. Chem., Int. Ed. 2012, 51, 12790-12794