Green and Sustainable Tandem Catalytic Approach for Fine-Chemicals Synthesis Using Octahedral MnO2 Molecular Sieve: Catalytic Activity versus Method of Catalyst Synthesis

ACS Sustainable Chemistry and Engineering

Volumn 3, Issue 11, 2015, Pages 2933-2943

  Sarmah, Bhaskar ^a   Srivastava, Rajendra ^a   Manjunathan, Pandian ^b   Shanbhag, Ganapati V ^b  

^a INDIAN INSTITUTE OF TECHNOLOGY ROPAR   (India)

^b POORNAPRAJNA INSTITUTE OF SCIENTIFIC RESEARCH   (India)

Author keywords

Condensation; Hydration; MnO2; Multifunctional catalyst; OMS; Oxidation; Tandem reaction

Indexed keywords

CARBON DIOXIDE; CATALYSIS; CATALYSTS; CONDENSATION; CONDENSATION REACTIONS; HYDRATION; HYDROTHERMAL SYNTHESIS; KETONES; MANGANESE OXIDE; MOLECULAR SIEVES; OXIDATION; SCANNING ELECTRON MICROSCOPY; SIEVES; SYNTHESIS (CHEMICAL); TEMPERATURE PROGRAMMED DESORPTION; THERMOGRAVIMETRIC ANALYSIS; ULTRAVIOLET VISIBLE SPECTROSCOPY; UREA; X RAY DIFFRACTION;

CATALYST SYNTHESIS; MNO2; MULTIFUNCTIONAL CATALYSTS; OMS; SOLVENT-FREE METHOD; SYNTHESIS METHOD; TANDEM REACTION; UV VISIBLE SPECTROSCOPY;

CATALYST ACTIVITY;

EID: 84946225659     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.5b00896     Document Type: Article

References (48)

1. Cundy, C. S.; Cox, P. A. The hydrothermal synthesis of zeolites: History and development from the earliest days to the present time Chem. Rev. 2003, 103, 663-702 10.1021/cr020060i
2. Corma, A. From microporous to mesoporous molecular sieve materials and their use in catalysis Chem. Rev. 1997, 97, 2373-2420 10.1021/cr960406n
3. Gawande, M. B.; Pandey, R. K.; Jayaram, R. V. Role of mixed metal oxides in catalysis science-versatile applications in organic synthesis Catal. Sci. Technol. 2012, 2, 1113-1125 10.1039/c2cy00490a
4. He, S.; An, Z.; Wei, M.; Evans, D. G.; Duan, X. Layered double hydroxide-based catalysts: Nanostructure design and catalytic performance Chem. Commun. 2013, 49, 5912-5920 10.1039/c3cc42137f
5. Varma, R. S. Green and sustainable chemistry Appl. Sci. 2014, 4, 493-497 10.3390/app4040493
6. Brock, S. L.; Duan, N.; Tian, Z. R.; Giraldo, O.; Zhou, H.; Suib, S. L. A review of porous manganese oxide materials Chem. Mater. 1998, 10, 2619-2628 10.1021/cm980227h
7. Chen, Z.; Jiao, Z.; Pan, D.; Li, Z.; Wu, M.; Shek, C.-H.; Wu, C. M. L.; Lai, J. K. L. Recent advances in manganese oxide nanocrystals: Fabrication, characterization, and microstructure Chem. Rev. 2012, 112, 3833-3855 10.1021/cr2004508
8. Zhang, K.; Han, X.; Hu, Z.; Zhang, X.; Tao, Z.; Chen, J. Nanostructured Mn-based oxides for electrochemical energy storage and conversion Chem. Soc. Rev. 2015, 44, 699-728 10.1039/C4CS00218K
9. 2 nanostructures for electrochemical supercapacitors Cryst. Growth Des. 2009, 9, 528-533 10.1021/cg800834g
10. 2 on its electrochemical capacitance properties J. Phys. Chem. C 2008, 112, 4406-4417 10.1021/jp7108785
11. 2 nanotubes J. Phys. Chem. C 2008, 112, 12594-12598 10.1021/jp8052967
12. 2 nanotubes J. Phys. Chem. B 2005, 109, 16439-16443 10.1021/jp052370l
13. 2 with bipyramid prism morphology CrystEngComm 2013, 15, 6682-6689 10.1039/c3ce40608c
14. Fekete, M.; Hocking, R. K.; Chang, S. L.Y.; Italiano, C.; Patti, A. F.; Arena, F.; Spiccia, L. Highly active screen-printed electrocatalysts for water oxidation based on β-manganese oxide Energy Environ. Sci. 2013, 6, 2222-2232 10.1039/c3ee40429c
15. 2 structures and their application in rechargeable Li-ion batteries Cryst. Growth Des. 2008, 8, 2799-2805 10.1021/cg701044b
16. 2 with large surface area J. Mater. Sci. 2012, 47, 999-1003 10.1007/s10853-011-5879-8
17. 2 nanofibers and its electrochemical application in the simultaneous determination of catechol, hydroquinone, and resorcinol Sens. Actuators, B 2013, 186, 67-77 10.1016/j.snb.2013.05.076
18. 2 modified electrode Electrochim. Acta 2013, 114, 285-295 10.1016/j.electacta.2013.10.064
19. Shen, Y. F.; Zerger, R. P.; DeGuzman, R. N.; Suib, S. L.; McCurdy, L.; Potter, D. I.; O'Young, C. L. Manganese oxide octahedral molecular sieves: Preparation, characterization, and applications Science 1993, 260, 511-515 10.1126/science.260.5107.511
20. De Guzman, R. N.; Shen, Y.-F.; Suib, S. L.; Shaw, B. R.; O'Young, C.-L. Role of cyclic voltammetry in characterizing solids: Natural and synthetic manganese oxide octahedral molecular sieves Chem. Mater. 1993, 5, 1395-1400 10.1021/cm00034a006
21. De Guzman, R. N.; Shen, Y.-F.; Neth, E. J.; Suib, S. L.; O'Young, C.-L.; Levine, S.; Newsam, J. M. Synthesis and characterization of octahedral molecular sieves (OMS-2) having the hollandite structure Chem. Mater. 1994, 6, 815-821 10.1021/cm00042a019
22. Xia, G.-G.; Tong, W.; Tolentino, E. N.; Duan, N.-G.; Brock, S. L.; Wang, J.-Y.; Suib, S. L.; Ressler, T. Synthesis and characterization of nanofibrous sodium manganese oxide with a 2 × 4 tunnel structure Chem. Mater. 2001, 13, 1585-1592 10.1021/cm000777r
23. Golden, D. C.; Chen, C. C.; Dixon, J. B. Synthesis of Todorokite Science 1986, 231, 717-719 10.1126/science.231.4739.717
24. Shen, X.-F.; Ding, Y.-S.; Liu, J.; Cai, J.; Laubernds, K.; Zerger, R. P.; Vasiliev, A.; Aindow, M.; Suib, S. L. Control of nanometer-scale tunnel sizes of porous manganese oxide octahedral molecular sieve nanomaterials Adv. Mater. 2005, 17, 805-809 10.1002/adma.200401225
25. Feng, Q.; Kanoh, H.; Miyai, Y.; Ooi, K. Alkali metal ions insertion/extraction reactions with hollandite-type manganese oxide in the aqueous phase Chem. Mater. 1995, 7, 148-153 10.1021/cm00049a023
26. Santos, V. P.; Soares, O. S. G. P.; Bakker, J. J. W.; Pereira, M. F. R.; Orfão, J. J. M.; Gascon, J.; Kapteijn, F.; Figueiredo, J. L. Structural and chemical disorder of cryptomelane promoted by alkali doping: Influence on catalytic properties J. Catal. 2012, 293, 165-174 10.1016/j.jcat.2012.06.020
27. Chen, X.; Shen, Y.-F.; Suib, S. L.; O'Young, C. L. Catalytic decomposition of 2-propanol over different metal-cation-doped OMS-2 materials J. Catal. 2001, 197, 292-302 10.1006/jcat.2000.3063
28. King'ondu, C. K.; Opembe, N.; Chen, C.; Ngala, K.; Huang, H.; Iyer, A.; Garcés, H. F.; Suib, S. L. Manganese oxide octahedral molecular sieves (OMS-2) multiple framework substitutions: A new route to OMS-2 particle size and morphology control Adv. Funct. Mater. 2011, 21, 312-323 10.1002/adfm.201001020
29. Hernández, W. Y.; Centeno, M. A.; Ivanova, S.; Eloy, P.; Gaigneaux, E. M.; Odriozola, J. A. Cu-modified cryptomelane oxide as active catalyst for CO oxidation reactions Appl. Catal., B 2012, 123-124, 27-35 10.1016/j.apcatb.2012.04.024
30. Varma, R. S.; Saini, R. K.; Dahiya, R. Active manganese dioxide on silica: oxidation of alcohols under solvent-free conditions using microwaves Tetrahedron Lett. 1997, 38, 7823-7824 10.1016/S0040-4039(97)10093-4
31. 2 catalyzed solvent free synthesis of xanthene laser dyes J. Mol. Catal. A: Chem. 2014, 392, 31-38 10.1016/j.molcata.2014.04.035
32. 2-MWCNT nanocomposites as efficient catalyst in the synthesis of Biginelli-type compounds under microwave radiation J. Mol. Catal. A: Chem. 2013, 373, 72-77 10.1016/j.molcata.2013.02.021
33. Kumar, R.; Sithambaram, S.; Suib, S. L. Cyclohexane oxidation catalyzed by manganese oxide octahedral molecular sieves-effect of acidity of the catalyst J. Catal. 2009, 262, 304-313 10.1016/j.jcat.2009.01.007
34. Ding, Y.-S.; Shen, X.-F.; Sithambaram, S.; Gomez, S.; Kumar, R.; Crisostomo, V. M. B.; Suib, S. L.; Aindow, M. Synthesis and catalytic activity of cryptomelane-type manganese dioxide nanomaterials produced by a novel solvent-free method Chem. Mater. 2005, 17, 5382-5389 10.1021/cm051294w
35. Wang, Y.; Kobayashi, H.; Yamaguchi, K.; Mizuno, N. Manganese oxide-catalyzed transformation of primary amines to primary amides through the sequence of oxidative dehydrogenation and successive hydration Chem. Commun. 2012, 48, 2642-2644 10.1039/c2cc17499e
36. Yamaguchi, K.; Kobayashi, H.; Oishi, T.; Mizuno, N. Heterogeneously catalyzed synthesis of primary amides directly from primary alcohols and aqueous ammonia Angew. Chem., Int. Ed. 2012, 51, 544-547 10.1002/anie.201107110
37. Yamaguchi, K.; Kobayashi, H.; Wang, Y.; Oishi, T.; Ogasawara, Y.; Mizuno, N. Green oxidative synthesis of primary amides from primary alcohols or aldehydes catalyzed by a cryptomelane-type manganese oxide-based octahedral molecular sieve, OMS-2 Catal. Sci. Technol. 2013, 3, 318-327 10.1039/C2CY20178J
38. Kim, J. W.; Yamaguchi, K.; Mizuno, N. Heterogeneously catalyzed efficient oxygenation of primary amines to amides by a supported ruthenium hydroxide catalyst Angew. Chem., Int. Ed. 2008, 47, 9249-9251 10.1002/anie.200802464
39. Baig, R. B. N.; Nadagouda, M. N.; Varma, R. S. Ruthenium on chitosan: a recyclable heterogeneous catalyst for aqueous hydration of nitriles to amides Green Chem. 2014, 16, 2122-2127 10.1039/c3gc42004c
40. Baig, R. B. N.; Varma, R. S. A facile one-pot synthesis of ruthenium hydroxide nanoparticles on magnetic silica: aqueous hydration of nitriles to amides Chem. Commun. 2012, 48, 6220-6222 10.1039/c2cc32566g
41. Xu, L.; Li, C.-G.; Zhang, K.; Wu, P. Bifunctional tandem catalysis on multilamellar organic-inorganic hybrid zeolites ACS Catal. 2014, 4, 2959-2968 10.1021/cs500653p
42. 2-MIL-101(Al) Chem. Commun. 2012, 48, 11650-11652 10.1039/c2cc36678a
43. Tran, U. P. N.; Le, K. K. A.; Phan, N. T. S. Expanding applications of metal-organic frameworks: Zeolite imidazolate framework ZIF-8 as an efficient heterogeneous catalyst for the knoevenagel reaction ACS Catal. 2011, 1, 120-127 10.1021/cs1000625
44. Li, P.; Cao, C.-Y.; Chen, Z.; Liu, H.; Yu, Y.; Song, W.-G. Core-shell structured mesoporous silica as acid-base bi-functional catalyst with designated diffusion path for cascade reaction sequences Chem. Commun. 2012, 48, 10541-10543 10.1039/c2cc35718f
45. Shiju, N. R.; Alberts, A. H.; Khalid, S.; Brown, D. R.; Rothenberg, G. Mesoporous silica with site-isolated amine and phosphotungstic acid groups: A solid catalyst with tunable antagonistic functions for one-pot tandem reactions Angew. Chem., Int. Ed. 2011, 50, 9615-9619 10.1002/anie.201101449
46. Srivastava, R.; Iwasa, N.; Fujita, S.-I.; Arai, M. Synthesis of nanocrystalline MFI-zeolites with intracrystal mesopores and their application in fine chemical synthesis involving large molecules Chem.-Eur. J. 2008, 14, 9507-9511 10.1002/chem.200801113
47. Srivastava, R.; Sarmah, B.; Satpati, B. Nanocrystalline ZSM-5 based bi-functional catalyst for two step and three step tandem reactions RSC Adv. 2015, 5, 25998-26006 10.1039/C4RA16697C
48. Climent, M. J.; Corma, A.; Iborra, S.; Martí, L. Solid catalysts for multistep reactions: one-pot synthesis of 2,3-dihydro-1,5-benzothiazepines with solid acid and base catalysts ChemSusChem 2014, 7, 1177-1185 10.1002/cssc.201301064