Selective debenzylation of 1-benzyloxy-4-methoxy benzene over 5-sulfosalicylic acid-functionalized ordered mesoporous silica (SBA-15/SFSA) catalyst
Source abstract
Abstract
5-Sulfosalicylic acid (SFSA) functionalized mesoporous silica nanocomposites (SBA/APTS/SFSA) were synthesized by post grafting technique for selective debenzylation of 1-benzyloxy-4-methoxy benzene. The uniform incorporation of SFSA inside the mesoporous SBA-15 framework was confirmed by standard characterization techniques (PXRD, adsorption studies, FT-IR, etc.). Total surface area, pore size and pore volume of the SBA/APTS/SFSA catalysts decreased with increase in the concentration of SFSA confirming the uniform insertion of SFSA into mesoporous SBA-15 matrix. Catalytic activity studies showed highest conversion and selectivity of the desired product on SBA/APTS/SFSA catalyst compared to homogeneous SFSA and other solid support (Al2O3 and SiO2). All the reaction parameters such as reaction time, reaction temperature and catalyst weight were optimized under environmental friendly conditions. Finally, the possible mechanism of the reaction was explained.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Mesoporous Materials and Catalysis · Zeolite Catalysis and Synthesis · Catalytic Processes in Materials Science
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References (28)
Show source-provided references
1. Baxter BT, Pearce WH, Waltke EA, Littooy FN, Hallett JW Jr, Kent KC, Upchurch GR Jr, Chaikof EL, Mills JL, Fleckten B, Longo GM, Lee JK, Thompson RW (2002) Prolonged administration of doxycycline in patients with small asymptomatic abdominal aortic aneurysms: report of a prospective (phase II) multicenter study. J Vasc Surg 36(1):1–12. https://doi.org/10.1067/mva.2002.12501810.1067/mva.2002.125018 ↗
2. Corma A (1997) From microporous to mesoporous molecular sieve materials and their use in catalysis. Chem Rev 97(6):2373–2420. https://doi.org/10.1021/cr960406n10.1021/cr960406n ↗
3. Crudden C, Sateesh M, Lewis R (2005) Mercaptopropyl-modified mesoporous silica: a remarkable support for the preparation of a reusable, heterogeneous palladium catalyst for coupling reactions. J Am Chem Soc 127(28):10045–10050. https://doi.org/10.1021/ja043095410.1021/ja0430954 ↗
4. Divya S, Amit D, Robin W, Ankita S (2015) Mesoporous silica polymer nanocomposites encapsulated with polyphosphoric acid for the synthesis of β-amino carbonyl compounds under environmental benign conditions. New J Chem 39:263310.1039/C4NJ01748J ↗
5. Feng X, Long J, Qia X (2014) A powerful combination: recent achievements on using TBAI and TBHP as oxidation system. Org Biomol Chem 12:580710.1039/C4OB00276H ↗
6. Hoerauf A, Mand S, Adjei O (2001) Depletion of Wolbachia endobacteria in Onchocerca volvulus by doxycycline and microfilaridermia after ivermectin treatment. Lancet 357(9266):1415–1416. https://doi.org/10.1016/S0140-6736(00)04581-510.1016/S0140-6736(00)04581-5 ↗
7. Imteaz A, Sung HJ (2014) Composites of metal–organic frameworks: preparation and application in adsorption. Mater Today 17:136–14610.1016/j.mattod.2014.03.002 ↗
8. Kamel AM, Brown PR, Munson B (1999) Electrospray ionization mass spectrometry of tetracycline, oxytetracycline, chlorotetracycline, minocycline, and methacycline. Anal Chem 71(5):968–977. https://doi.org/10.1021/ac980711410.1021/ac9807114 ↗
9. Linna Z, Wenjing W, Shanyan Y (2008) Selective debenzylation of aromatic benzyl ethers by silica-supported sodium hydrogen sulfate. Tetrahedron Lett 49:4876–487810.1016/j.tetlet.2008.06.007 ↗
10. Marshall T, Williams K (2000) Total protein determination in urine: elimination of a differential response between the coomassie blue and pyrogallol red protein dye-binding assays. Clin Chem 46(3):392–39810.1093/clinchem/46.3.392 ↗
11. Ono Y (2003) Solid base catalysts for the synthesis of fine chemicals. J Catal 216(1-2):406–415. https://doi.org/10.1016/S0021-9517(02)00120-310.1016/S0021-9517(02)00120-3 ↗
12. Palaniappana S, John A, Amarnath C, Rao V (2004) Mannich-type reaction in solvent free condition using reusable polyaniline catalyst. J Mol Catal 218(1):47–53. https://doi.org/10.1016/j.molcata.2004.04.01010.1016/j.molcata.2004.04.010 ↗
13. Pinnavaia T (1983) Intercalated clays catalysts. Science 220:459510.1126/science.220.4595.365 ↗
14. Ramesh C, Ravindranath N, Das B (2003) Efficient, and selective deprotection of phenolic methoxymethyl ethers using silica-supported sodium hydrogen sulfate as a heterogeneous catalyst. J Org Chem 68(18):7101–7103. https://doi.org/10.1021/jo030088+10.1021/jo030088+ ↗
15. Ravikovitch PI, Neimark AV (2001) Characterization of micro- and mesoporosity in SBA-15 materials from adsorption data by the NLDFT method. J Phys Chem B 105(29):6817–6823. https://doi.org/10.1021/jp010621u10.1021/jp010621u ↗
16. Robin W, Amit D (2016a) Mesoporous silica polymer nanocomposites functionalized with vinyl pyridine and vinyl pyrrolidinone for the adsorption of humic acid. Adv Mater Lett 7:760–76410.5185/amlett.2016.6077 ↗
17. Robin W, Amit D (2016b) Synthesis and characterization of trichloroisocyanouric acid functionalized mesoporous silica nanocomposite (SBA/TCCA) for the acylation of indole. J Chem Sci 128:128510.1007/s12039-016-1131-z ↗
18. Sachdeva D, Wilson G, Srivastava NM, Dubey A (2014) Debenzylation of vanillic acid over sulfosuccinic acid functionalized mesoporous silica nanocomposites. Catal Commun 5:90–9410.1016/j.catcom.2014.03.001 ↗
19. Sajiki H (1995) Selective inhibition of benzyl ether hydrogenolysis with Pd/C due to the presence of ammonia, pyridine or ammonium acetatel. Tetrahedron Lett 36(20):3465–3468. https://doi.org/10.1016/0040-4039(95)00527-J10.1016/0040-4039(95)00527-J ↗
20. Shane D, Lyon MW (2010) Comparison of urine dipstick, sulfosalicylic acid, urine protein-to-creatinine ratio, and species-specific ELISA methods for detection of albumin in urine samples of cats and dogs. J Am Vet Med Assoc 236:874–87910.2460/javma.236.8.874 ↗
21. Shiobara T, Teshima N, Kurihara M (1999) Catalytic flow injection determination of vanadium by oxidation of N-(3-sulfopropyl)-3,3%,5,5%-tetramethylbenzidine using bromated. Talanta 49(5):1083–1089. https://doi.org/10.1016/S0039-9140(99)00020-X10.1016/S0039-9140(99)00020-X ↗
22. Varghese HT, Panicker C, Philip D (2007) IR, Raman and SERS spectra of 5-sulphosalicylic acid dehydrate. J Raman Spectrosc 38(3):309–315. https://doi.org/10.1002/jrs.164410.1002/jrs.1644 ↗
23. Vinu A, Hossain KZ, Ariga K (2005) Recent advances in functionalization of mesoporous silica. J Nanosci Nanotechnol 5(3):347–371. https://doi.org/10.1166/jnn.2005.08910.1166/jnn.2005.089 ↗
24. Wan Y, Zhao D (2007) On the controllable soft-templating approach to mesoporous silicates. Chem Rev 107(7):2821–2860. https://doi.org/10.1021/cr068020s10.1021/cr068020s ↗
25. Wang X, Wu Y, Bao L (2010) Interfacial synthesis of polyaniline nanostructures induced by 5-sulfosalicylic acid. Mater Lett 64(17):1865–1867. https://doi.org/10.1016/j.matlet.2010.06.00610.1016/j.matlet.2010.06.006 ↗
26. Yadav G, George G (2006) Friedel–crafts acylation of anisole with propionic anhydride over mesoporous superacid catalyst UDCaT-5. Microporous Mesoporous Mater 96(1-3):36–43. https://doi.org/10.1016/j.micromeso.2006.05.03110.1016/j.micromeso.2006.05.031 ↗
27. Zhang Z, Wei Z, Wan M (2002) Nanostructures of polyaniline doped with inorganic acids. Macromolecules 35(15):5937–5942. https://doi.org/10.1021/ma020199v10.1021/ma020199v ↗
28. Zhao D, Sun J, Li Q, Stucky GD (2000) Morphological control of highly ordered mesoporous silica SBA-15. Chem Mater 12(2):275–279. https://doi.org/10.1021/cm991136310.1021/cm9911363 ↗