Acetalization of carbonyl compounds with pentaerythritol catalyzed by metal(IV) phosphates as solid acid catalysts

Industrial and Engineering Chemistry Research

Volumn 52, Issue 26, 2013, Pages 8969-8977

  Parangi, Tarun F ^a   Wani, Bina N ^b   Chudasama, Uma V ^a  

^a M S UNIVERSITY OF BARODA   (India)

^b BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BRUNAUER-EMMETT-TELLER SURFACE AREAS; CERIUM PHOSPHATE; ENERGY DISPERSIVE X-RAY; INDUCTIVELY COUPLED PLASMA-ATOMIC EMISSION SPECTROMETRY; ORGANIC SOLVENT MEDIA; SOLID ACID CATALYSTS; VARYING PARAMETERS; X-RAY DIFFRACTION STUDIES;

ATOMIC EMISSION SPECTROSCOPY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; INDUCTIVELY COUPLED PLASMA; KETONES; POLYPROPYLENES; SCANNING ELECTRON MICROSCOPY; SOL-GEL PROCESS; SPECTRUM ANALYSIS; TEMPERATURE PROGRAMMED DESORPTION; THERMOANALYSIS; X RAY DIFFRACTION;

CATALYSTS;

EID: 84879863528     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie400686d     Document Type: Article

References (58)

1. Greene, T. W. Protective Groups in Organic Synthesis; Wiley: New York, 1981; p 114.
2. Srivastava, P.; Srivastava, R. A novel method for the protection of amino alcohols and carbonyl compounds over a heterogeneous, reusable catalyst Catal. Commun. 2008, 9, 645-649
3. Patel, S.; Chudasama, U.; Ganeshpure, P. Ketalization of ketones with diols catalyzed by metal (IV) phosphates as solid acid catalysts J. Mol. Catal. A: Chem. 2003, 194, 267-271
4. Chandan, S.; Malik, H. Protection of the carbonyl group as 1,2,4-trioxane and its regeneration under basic conditions Org. Lett. 2005, 7, 5673-5676
5. Wang, P.; Kong, A. G.; Wang, W. J.; Zhu, H. Y.; Shan, Y. K. Facile preparation of ionic liquid functionalized magnetic nano-solid acid catalyst for acetalization reaction Catal. Lett. 2010, 135, 159-164
6. Climent, M. J.; Velty, A.; Corma, A. Design of a solid catalyst for the synthesis of a molecule with blossom orange scent Green Chem. 2002, 4, 565-569
7. nd ed.; VCH: New York, 1990.
8. Clode, D. M. Carbohydrate cyclic acetal formation and migration Chem. Rev. 1979, 79, 491-513
9. Ley, S. V.; Priepke, H.W. M. Eintopfsynthese einer trisaccharideinheit des gemeinen polysaccharid-antigens von Streptococci der Gruppe B unter verwendung cyclohexan-1,2-diacetal(CDA)-geschützter rhamnoside Angew. Chem. 1994, 106, 2412-2414
10. Bruns, K.; Conard, J.; Steigel, A. Stereochemistry of cyclic compounds-I: Synthesis and conhgurational assignment of diawereomeric 2,4-dioxaspir[5.5] undec-8-enes Tetrahedran 1979, 35, 2523-2530
11. Cheung, M. K.; Douglas, N. L.; Hinzen, B.; Ley, S. V.; Pannecoucke, X. One-pot synthesis of tetra- and pentasaccharides from monomeric building blocks using the principles of orthogonality and reactivity tuning Synlett 1997, 3, 257-260
12. Narasaka, K.; Inone, M.; Yamada, T.; Sugiomori, J.; Iwasawa, N. Asymmetric diels-alder reaction by the use of a chiral titanium catalyst with molecular sieves 4A. Remarkable solvent effect on the enantioselectivity Chem. Lett. 1987, 2409-2412
13. Elliot, A. J. 1,3-Dioxalane Polymers in Comprehensive Heterocyclic Polymers1,3-Dioxalane Polymers in Comprehensive Heterocyclic Polymers; Pergamon Press: Oxaford, UK, 1984; p 6.
14. Hille, M.; Wittkus, H.; Scholz, H. J.; Weimlet, F. Use of acetals. U.S. Patent 5,759,963, 1998.
15. Barros, A. O.; Faisca, A. T.; Latcher, E. R.; Nascimento, R. S. V.; Gil, R. A. S. Acetalization of hexanal with 2-ethyl hexanol catalyzed by solid acids J. Braz. Chem. Soc. 2011, 22 (2) 359-363
16. Bornstein, J.; Bedell, S. F.; Drummond, P. E.; Kosoloki, C. F. The synthesis of α-amino- o- tolualdehyde diethylacetal J. Am. Chem. Soc. 1956, 78, 83-86
17. McKinzie, C. A.; Stocker, J. H. Preparation of ketals. A reaction mechanism J. Org. Chem. 1955, 20, 1695-1701
18. 15N]amino-2-deoxy-β- d -glucopyranoside derivatives Carbohydr. Res. 2001, 334, 271-279
19. Kartha, K. P. R. Iodine, a novel catalyst in carbohydrate reactions I. o -Isopropylidination of carbohydrates Tetrahedron Lett. 1986, 27, 3415-3416
20. Winnik, F. M.; Carver, J. P.; Krepinsky, J. J. Syntheses of model oligosaccharides of biological significance. Synthesis of a tetramannoside and of two lyxose-containing Trisaccharides J. Org. Chem. 1982, 47, 2701-2707
21. Cataldo, M.; Neiddu, F.; Gavagnin, R.; Pinna, F.; Strukul, G. Hydroxy complexes of palladium (II) and platinum (II) as catalysts for the acetalization of aldehydes and ketones J. Mol. Catal. A: Chem. 1999, 142, 305-316
22. Neiddu, E.; Cataldo, M.; Pinna, F.; Strukul, G. Acetalization of α,β-unsaturated carbonyl compounds catalyzed by complexes of Pt(II) Tetrahedron Lett. 1999, 40, 6987-6990
23. Thomas, B.; Sreedharan, P.; Sugunan, S. Synthesis of dimethyl acetal of ketones: Design of solid acid catalysts for one-pot acetalization reaction Microporous Mesoporous Mater. 2005, 80, 65-72
24. Patel, S.; Chudasama, U.; Ganeshpure, P. Metal(IV) phosphates as solid acid catalysts for selective cyclodehydration of 1, n -diols Green Chem. 2001, 3, 143-145
25. Lin, C. H.; Lin, S. D.; Yang, Y. H.; Lin, T. P. The synthesis and hydrolysis of dimethyl acetals catalyzed by sulfated metal oxides. An efficient method for protecting carbonyl groups Catal. Lett. 2001, 73 (2-4) 121-125
26. 3+-Mont) as a useful substrate-selective acetalization catalyst J. Org. Chem. 1995, 60, 4039-4043
27. Corma, A.; Climent, M. J.; Garcia, H.; Primo, J. Formation and hydrolysis of acetals catalysed by acid faujasites Appl. Catal., A: Gen. 1990, 59, 333-340
28. Ballini, R.; Bosica, G.; Frullanti, B.; Maggi, R.; Sartori, G.; Schroer, F. 1,3-Dioxolanes from carbonyl compounds over zeolite HSZ-360 as a reusable, heterogeneous catalyst Tetrahedron Lett. 1998, 39, 1615-1618
29. Algarre, F.; Corma, A.; Garcia, H.; Primo, J. Acid zeolites as catalysts in organic reactions. Highly selective condensation of 2-alkylfurans with carbonylic compounds Appl. Catal., A: Gen. 1995, 128, 119-126
30. Iwamoto, M.; Tanaka, Y.; Sawamura, N.; Namba, S. Remarkable effect of pore size on the catalytic activity of mesoporous silica for the acetalization of cyclohexanone with methanol J. Am. Chem. Soc. 2003, 125 (43) 13032-13033
31. Climent, M. J.; Corma, A.; Iborra, S.; Navarro, M. C.; Primo, J. Use of mesoporous MCM-41 aluminosilicates as catalysts in the production of fine chemicals: Preparation of dimethylacetals J. Catal. 1996, 161, 783-789
32. Tanaka, Y.; Sawamura, N.; Iwamoto, M. Highly effective acetalization of aldehydes and ketones with methanol on siliceous mesoporous material Tetrahedron Lett. 1998, 39, 9457-9460
33. 3 as an efficient catalyst for acetalization of carbonyl compounds under heterogeneous or solvent-free conditions J. Braz. Chem. Soc. 2005, 16, 877-880
34. Mayoral, E. P.; Martin-Aranda, R. M.; Lopez-Peinado, A. J.; Ballestreos, P.; Zukla, A.; Cejka, J. Green synthesis of acetals/ketals: Efficient solvent-free process for the carbonyl/hydroxyl group protection catalyzed by SBA-15 materials Top. Catal. 2009, 52, 148-152
35. 3 as a recyclable and selective catalyst for the acetalization of aldehydes and ketones J. Braz. Chem. Soc. 2010, 21, 371-374
36. Kannan, V.; Sreekumar, K.; Gil, A.; Vicente, M. A. Acetalation of pentaerithritol catalyzed by an Al-pillared saponite Catal. Lett. 2011, 141, 1118-1122
37. 2-Cl) in organic synthesis. Efficient preparation of diacetals of 2,2-bis(hydroxymethyl)-1,3-propanediol from different substrates and their transthioacetalization reactions. Efficient regeneration of carbonyl compounds from acetals and acylals Phosphorus, Sulfur Silicon 2002, 177, 2847-2858
38. 40 supported on MCM-41 molecular sieves: An effective catalyst for acetal formation Appl. Catal., A: Gen. 2005, 295, 185-192
39. Patel, P.; Shivanekar, A.; Chudasama, U. Use of zirconium tungstate in acid catalysis: Some esterification reactions Indian J. Chem. 1992, 31A, 803-805
40. Shivanekar, A.; Chudasama, U. Recent Trends in Catalysis; Vishwanathan, B.,; Pillai, C. N., Eds.; Narosa Publishing House: New Delhi, 1990; p 489-497.
41. Parikh, A.; Patel, A.; Chudasama, U. Recent Trends in Catalysis; Murugesan, V.; Arbindoo, B.; Palanichamy, M., Eds.; Narosa Publishing House, New Delhi, 1999; p 421-426.
42. Beena, B.; Chudasama, U. A comparative study of the Brønsted acidity of zirconium phosphate and zirconium phenyl phosphonate Indian J. Chem. Tech. 1995, 2, 339-340
43. Patel, S.; Chudasama, U. Synthesis, characterization and catalytic application of tin phosphate Indian J. Chem. 2002, 41A, 1864-1866
44. Parikh, A.; Chudasama, U. Metal (IV) tungstates as solid acid catalysts for the synthesis of phthalate diester-dioctyl phthalate (DOP) Indian J. Chem. Tech. 2003, 10, 44-47
45. Joshi, R.; Patel, H.; Chudasama, U. Synthesis of monoester and diesters using eco-friendly solid acid catalysts M(IV) Tungstates and phosphates Indian J. Chem. Technol. 2008, 15, 238-243
46. Patel, H.; Joshi, R.; Chudasama, U. Use of zirconium (IV) phosphate as a solid acid catalyst in some esterification reactions Indian J. Chem. 2008, 47A, 348-352
47. Thakkar, R.; Chudasama, U. Synthesis of mono and diesters using eco-friendly solid acid catalyst-zirconium titanium phosphate Green Chem. Lett. Rev. 2009, 2 (2) 61-69
48. Joshi, R.; Chudasama, U. Synthesis of coumarins via the Pechmann condensation using inorganic ion exchangers as solid acid catalysts J. Sci. Ind. Res. 2008, 67, 1092-1097
49. Ghodke, S.; Chudasama, U. Solvent free synthesis of coumarins using environment friendly solid acid catalysts Appl. Catal., A: Gen. 2013, 453, 219-226
50. Patel, P.; Chudasama, U. Thermodynamics and kinetics of ion exchange of a hybrid cation exchanger, zirconium diethylene triamine pentamethylene phosphonate Indian J. Chem., Sect. A 2010, 49, 1318-1324
51. Bhaumik, A.; Inagaki, S. Mesoporous titanium phosphate molecular sieves with ion-exchange capacity J. Am. Chem. Soc. 2001, 123, 691-696
52. Seip, C. T.; Granroth, G. E.; Miesel, M. W.; Talham, D. R. Langmuir-Blodgett films of known layered solids: preparation and structural properties of octadecylphosphonate bilayers with divalent metals and characterization of a magnetic Langmuir-Blodgett film J. Am. Chem. Soc. 1997, 119, 7084-7094
53. Nilchi, A.; Ghanadi, M. M.; Khanchi, A. Characteristics of novel types substituted cerium phosphates J. Radioanal. Nucl. Chem. 2000, 245 (2) 589-594
54. Agirre, I.; García, I.; Requies, J.; Barrio, V. L.; Guemez, M. B.; Cambra, J. F.; Arias, P. L. Glycerol acetals, kinetic study of the reaction between glycerol and formaldehyde Biomass Bioenergy 2011, 35, 3636-3642
55. Agirre, I.; Barrio, V. L.; Güemez, B.; Cambra, J. F.; Arias, P. L. Catalytic reactive distillation process development for 1,1 diethoxy butane production from renewable sources Bioresour. Technol. 2011, 102, 1289-1297
56. Chopade, S. P.; Sharma, M. M. Reaction of ethanol and formaldehyde: Use of versatile cation-exchange resins as catalyst in batch reactors and reactive distillation columns React. Funct. Polym. 1997, 32 (1) 53-65
57. Domalski, E. S. Selected values of heats of combustion and formation of organic compound containing C, H, N, O, P and S J. Phys. Chem. Ref. Data 1972, 1 (2) 221
58. Rui, P. V.; Pereira, C. S. M.; Silva, V. M. T. M.; Loureiro, J. M.; Rodrigues, A. E. Glycerol valorization as biofuel: Thermodynamic and kinetic study of the acetalization of glycerol with acetaldehyde Ind. Eng. Chem. Res. 2013, 52, 1538-1547