Efficient esterification reaction of palmitic acid catalyzed by WO_3-x/mesoporous silica

References

• Wacławek S, Padil VVT, Černík M. Major advances and challenges in heterogeneous catalysis for environmental applications: a review. Ecol Chem Eng S. 2018;25:9–34.
   Web of Science ®Google Scholar
• Noh HJ, Lee SY, Jang YS. Microbial production of butyl butyrate, a flavor and fragrance compound. Appl Microbiol Biotechnol. 2019;103(5):2079–2086.
   PubMed Web of Science ®Google Scholar
• Cha HJ, Park JB, Park S. Esterification of secondary alcohols and multi-hydroxyl compounds by Candida antarctica lipase B and subtilisin. Biotechnol Bioproc E. 2019;24(1):41–47.
   Web of Science ®Google Scholar
• Mardhiah HH, Ong HC, Masjuki HH, et al. A review on latest developments and future prospects of heterogeneous catalyst in biodiesel production from non-edible oils. Renew Sustain Energy Rev. 2017;67:1225–1236.
   Web of Science ®Google Scholar
• Cordeiro CS, Da Silva FR, Wypych F, Ramos LP. Catalisadores heterogêneos para a produção de monoésteres graxos (biodiesel). Quím Nova. 2011;34(3):477–486.
   Google Scholar
• Mueanmas C, Prasertsit K, Tongurai C. Feasibility study of reactive distillation column for transesterification of palm oils. Int J Chem Eng Appl. 2013;1:77–83.
   Google Scholar
• Mishra VK, Goswami R. A review of production, properties and advantages of biodiesel. Biofuels 2018;9(2):273–289.
   Web of Science ®Google Scholar
• Aransiola EF, Ikhu-Omoregbe DIO, Madzimbamuto TF, et al. A review of current technology for biodiesel production: state of the art. Biomass Bioenergy. 2014;61:276–297.
   Web of Science ®Google Scholar
• Atadashi IM, Aroua MK, Aziz AA. High quality biodiesel and its diesel engine application: a review. Renew Sustain Energy Rev. 2010;14(7):1999–2008.
   Web of Science ®Google Scholar
• Hykkerud A, Marchetti JM. Esterification of oleic acid with ethanol in the presence of Amberlyst 15. Biomass Bioenergy. 2016;95:340–343.
   Web of Science ®Google Scholar
• Baroi C, Mahto S, Niu C, et al. Biofuel production from green seed canola oil using zeolites. Appl Catal A Gen. 2014;469:18–32.
   Web of Science ®Google Scholar
• Rade LL, Lemos COT, Barrozo MAS, Ribas RM, et al. Optimization of continuous esterification of oleic acid with ethanol over niobic acid. Renew Energy. 2018;115:208–216.
   Web of Science ®Google Scholar
• Kaur J, Kaur K, Toor AP. Sulfated iron oxide-catalyzed esterification of acetic acid with n-butanol by reactive distillation. Chem Eng Technol. 2018;41(11):2196–2202.
   Web of Science ®Google Scholar
• Kaur K, Wanchoo RK, Toor AP. Sulfated iron oxide: a proficient catalyst for esterification of butanoic acid with glycerol. Ind Eng Chem Res. 2015;54(13):3285–3292.
   Web of Science ®Google Scholar
• Bala DD, Misra M, Chidambaram D. Solid-acid catalyzed biodiesel production, part I: biodiesel synthesis from low quality feedstock. J Clean Prod. 2017;142:4169–4177.
   Web of Science ®Google Scholar
• Yang XL, Dai WL, Gao R, et al. Characterization and catalytic behavior of highly active tungsten-doped SBA-15 catalyst in the synthesis of glutaraldehyde using an anhydrous approach. J Catal. 2007;249(2):278–288.
   Web of Science ®Google Scholar
• dos Santos VCC, Wilson K, Lee AFF, et al. Physicochemical properties of WOx/ZrO2 catalysts for palmitic acid esterification. Appl Catal B Environ. 2015;162:75–84.
   Web of Science ®Google Scholar
• Nogueira HIS, Cavaleiro AMV, Rocha J, et al. Synthesis and characterization of tungsten trioxide powders prepared from tungstic acids. Mater Res Bull. 2004;39(4-5):683–693.
   Web of Science ®Google Scholar
• Knothe G, Gerpen JV, Krahl J, Editors.The biodiesel handbook. Champaign (IL): AOCS Press; 2005.
   Google Scholar
• Kuti LM, Bhella SS, Thangadura V. Revisiting tungsten trioxide hydrates (TTHs) synthesis – is there anything new? Inorg Chem. 2009;48(14):6804–6811.
   PubMed Web of Science ®Google Scholar
• Zheng H, Ou JZ, Strano MS, et al. Nanostructured tungsten oxide – properties, synthesis, and applications. Adv Funct Mater. 2011;21(12):2175–2196.
   Web of Science ®Google Scholar
• Chemseddine A, Babonneau F, Livage J. Anisotropic WO3·nH2O layers deposited from gels. J Non Cryst Solids. 1987;91(2):271–278.
   Web of Science ®Google Scholar
• Yang J, Li W, Li J, et al. Hydrothermal synthesis and photoelectrochemical properties of vertically aligned tungsten trioxide (hydrate) plate-like arrays fabricated directly on FTO substrates. J Mater Chem. 2012;22(34):17744–17752.
   Web of Science ®Google Scholar
• Sadakane M, Sasaki K, Kunioku H, et al. Preparation of nano-structured crystalline tungsten(VI) oxide and enhanced photocatalytic activity for decomposition of organic compounds under visible light irradiation. Chem Commun. 2008;1:6552–6554.
   Google Scholar
• Dutta R, Singh SK, Mandavgane SA, et al. Polyoxometalate based mesoporous acidic catalyst from biogenic silica for vegetable oil methanolysis: Structure activity relationship study. Appl Catal A Gen. 2017;539:38–47.
   Web of Science ®Google Scholar
• Barton DG, Shtein M, Wilson RD, et al. Structure and electronic properties of solid acids based on tungsten oxide nanostructures. J Phys Chem B. 1999;103(4):630–640.
   Web of Science ®Google Scholar
• Kulal AB, Kasabe MM, Jadhav PV, et al. Hydrophobic WO3/SiO2 catalyst for the nitration of aromatics in liquid phase. Appl Catal A Gen. 2019;574:105–113.
   Web of Science ®Google Scholar
• Chen G, Dong M, Li J, et al. Self-metathesis of 1-butene to propene over SBA-15-supported WO3. Catal Sci Technol. 2016;6(14):5515–5525.
   Web of Science ®Google Scholar
• Triwahyono S, Yamada T, Hattori H. IR study of acid sites on WO3-ZrO2. Appl Catal A Gen. 2003;250(1):75–81.
   Web of Science ®Google Scholar
• Yang XL, Dai WL, Guo C, et al. Synthesis of novel core-shell structured WO3/TiO2spheroids and its application in the catalytic oxidation of cyclopentene to glutaraldehyde by aqueous H2O2. J Catal. 2005;234(2):438–450.
   Web of Science ®Google Scholar
• Chen L, Liu Y, Li Y. Preparation and characterization of ZrO2:Eu3+ phosphors. J Alloys Compd. 2004;381(1-2):266–271.
   Web of Science ®Google Scholar
• Parvulescu V, Anastasescu C, Constantin C, et al. Mono (V, Nb) or bimetallic (V-Ti, Nb-Ti) ions modified MCM-41 catalysts: synthesis, characterization and catalysis in oxidation of hydrocarbons (aromatics and alcohols). Catal Today. 2003;78(1-4):477–485.
   Web of Science ®Google Scholar
• Gotić M, Ivanda M, Popović S, et al. Synthesis of tungsten trioxide hydrates and their structural properties. Mater Sci Eng B Solid State Mater Adv Technol. 2000;77(2):193–201.
   Google Scholar
• Liu J, Wang B, Hartono SB, et al. Magnetic silica spheres with large nanopores for nucleic acid adsorption and cellular uptake. Biomaterials 2012;33(3):970–978.
   PubMed Web of Science ®Google Scholar
• Iannibelo A, Marengo S, Tittarelli P. Spectroscopic study of the structure of chromium(VI), on aluminium oxide. J Chem Soc Faraday Trans 1 Phys Chem Condens Phases. 1984;80:2209–2223.
   Google Scholar
• Fournier M, Louis C, Che M, et al. Polyoxometallates as models for oxide catalysts. Part I. An UV-visible reflectance study of polyoxomolybdates: influence of polyhedra arrangement on the electronic transitions and comparison with supported molybdenum catalysts. J Catal. 1989;119(2):400–414.
   Web of Science ®Google Scholar
• Jiménez-Morales I, Santamaría-González J, Maireles-Torres P, et al. Zirconium doped MCM-41 supported WO3 solid acid catalysts for the esterification of oleic acid with methanol. Appl Catal A Gen. 2010;379(1-2):61–68.
   Web of Science ®Google Scholar
• Liu H, Tao K, Yu H, et al. Effect of pretreatment gases on the performance of WO3/SiO2 catalysts in the metathesis of 1-butene and ethene to propene. Comptes Rendus Chim. 2015;18(6):644–653.
   Web of Science ®Google Scholar
• Gayapan K, Sripinun S, Panpranot J, et al. Effects of calcination and pretreatment temperatures on the catalytic activity and stability of H2-treated WO3/SiO2 catalysts in metathesis of ethylene and 2-butene. RSC Adv. 2018;8(50):28555–28568.
   Web of Science ®Google Scholar
• Wan Isahak WNR, Manal I, Nordin NM, et al. Synthesis and characterization of silicotungstic acid nanoparticles via sol gel technique as a catalyst in esterification reaction. Adv Mater Res. 2011;364:266–271.
   Google Scholar
• Leftheriotis G, Papaefthimiou S, Yianoulis P, et al. Effect of the tungsten oxidation states in the thermal coloration. Thin Solid Films.2001;384(2):298–306.
   Web of Science ®Google Scholar
• Lee JS, Jang IH, Park NG. Effects of oxidation state and crystallinity of tungsten oxide interlayer on photovoltaic property in bulk hetero-junction solar cell. J Phys Chem C. 2012;116(25):13480–13487.
   Web of Science ®Google Scholar
• Moulder JF, Stickle WE, Sobol PE, Editors. et al. Handbook of photoelectron spectroscopy. Waltham (MN): Perkin-Elmer Corporation; 1992.
   Google Scholar
• Sohn JR, Park EH. Characterization of ferric sulfate supported on zirconia and its relationship to acidic properties. J Ind Eng Chem 1998;4:197–204.
   Web of Science ®Google Scholar
• Son MJ, Kim S, Kwon S, et al. Interface electronic structures of organic light-emitting diodes with WO3 interlayer: A study by photoelectron spectroscopy. Org Electron Physics Mater Appl. 2009;10:637–642.
   Google Scholar
• Bussolotti F, Lozzi L, Passacantando M, et al. Surface electronic properties of polycrystalline WO3 thin films: a study by core level and valence band photoemission. Surf Sci. 2003;538(1-2):113–123.
   Web of Science ®Google Scholar
• Cimino R, Giarante A, Horn K, et al. Line broadening in semiconductor core level photoemission induced by barrier height inhomogeneity. Surf Sci. 1995;331–333:534–539.
   Web of Science ®Google Scholar
• Cortés-Jácome MA, Angeles-Chavez C, Bokhimi X, et al. Generation of WO3-ZrO2 catalysts from solid solutions of tungsten in zirconia. J Solid State Chem. 2006;179(8):2663–2673.
   Web of Science ®Google Scholar
• Zhu J, Vasilopoulou M, Davazoglou D, et al. Intrinsic defects and H doping in WO3. Sci Rep. 2007;7:1–9.
   Google Scholar
• Gayapan K, Sripinun S, Panpranot J, et al. Effect of pretreatment atmosphere of WOx/SiO2 catalysts on metathesis of ethylene and 2-butene to propylene. RSC Adv. 2018;8(21):11693–11704.
   Web of Science ®Google Scholar
• Kanan SM, Tripp CP. Synthesis, FTIR studies and sensor properties of WO3 powders. Curr Opin Solid State Mater Sci. 2007;11(1-2):19–27.
   Web of Science ®Google Scholar
• Lu G, Li X, Qu Z, et al. Correlations of WO3 species and structure with the catalytic performance of the selective oxidation of cyclopentene to glutaraldehyde on WO3/TiO2 catalysts. Chem Eng J. 2010;159(1-3):242–246.
   Web of Science ®Google Scholar
• Kanan SM, Lu Z, Cox JK, et al. Identification of surface sites on monoclinic WO3 powders by infrared spectroscopy. Langmuir 2002;18(5):1707–1712.
   Web of Science ®Google Scholar
• Aafaqi R, Mohamed AR, Bhatia S. Kinetics of esterification of palmitic acid with isopropanol using p-toluene sulfonic acid and zinc ethanoate supported over silica gel as catalysts. J Chem Technol Biotechnol. 2004;79(10):1127–1134.
   Web of Science ®Google Scholar
• Westhoff R, Moulijn JA. Reduction and activity of the metathesis catalyst WO3/SiO2. J Catal. 1977;46(3):414–416.
   Web of Science ®Google Scholar
• Choung SJ, Weller SW. Oxygen chemisorption and olefin disproportionation activity of WO3/SiO2. Ind Eng Chem Proc Des Dev. 1983;22(4):662–665.
   Google Scholar
• Scroccaro KI, Tanobe VOA, De Oliveira AA, et al. Impregnação do ácido 12-tungstofosfórico em sílica-parte II: efeito de diferentes solventes na impregnação e atividade catalítica na esterificação metílica de ácido esteárico. Quim Nova 2014;37:232–237.
   Google Scholar
• Aziz MAA, Puad K, Triwahyono S, et al. Transesterification of croton megalocarpus oil to biodiesel over WO3 supported on silica mesoporous-macroparticles catalyst. Chem Eng J. 2017;316:882–892.
   Web of Science ®Google Scholar