Abstract
X-ray amorphous titanium phosphate (TiP) prepared via precipitation from titanylsulfate showed low catalytic performances in the process of aldol condensation of acetic acid with formaldehyde for production of acrylic acid (AA). As-precipitated TiP was modified in the form of wet gel and dried xerogel using hydrothermal (HTT), microwave (MWT) and mechanochemical (MChT) treatments. The physical–chemical characteristics of initial and modified TiP were studied using XRD, FTIR, adsorption–desorption of nitrogen, ammonia thermo-programmed desorption. All types of treatment lead to significant but irregular changes in crystal and porous structure as well as surface acidity of TiP catalysts. The crystalline titanium hydro- and pyrophosphates are formed under hydrothermal conditions (HTT and MWT). These phases exhibit increased activity and selectivity with respect to acrylic acid. The formation of meso-macroporous structure also contributes to this. The most efficient catalyst contains crystalline titanium hydro- and pyrophosphates and has high total acidity with maximum content of strong acid sites, multimodal meso-macroporous structure and the highest share of macropores: AA yield on this catalyst is 61% at 80% acrylic acid selectivity. It can be prepared via HTT of xerogel at 300 °C.
Similar content being viewed by others
References
Method for production of acrolein and acrylic acid from propylene: patent 6545178 US//Michio Tanimoto, Daisuke Nakamura, Tatsuya Kawajiri; assignee: Nippon Shokubai Co., Ltd. (Osaka, JP). No 314719/09 filing date: 18.05.1999; publication date: 08.04.2003
Elliott DC (2003) Encyclopedia of energy. Chemicals from biomass. Battelle Pacific Northwest Division. http://www.pnl.gov/biobased/docs/encyclopedia.pdf
Yang D, Sararuk C, Suzuki K, Li Z, Li C (2016) Effect of calcination temperature on the catalytic activity of VPO for aldol condensation of acetic acid and formalin. Chem Eng J 300:160–168
Guo X, Yang D, Zuo C, Peng Z, Li C, Zhang S (2017) Catalysts, process optimization, and kinetics for the production of methyl acrylate over vanadium phosphorus oxide catalysts. Ind Eng Chem Res 56:5860–5871
Yang D, Li D, Yao H, Zhang G, Jiao T, Li Z, Li C, Zhang S (2015) Reaction of formalin with acetic acid over vanadium-phosphorus oxide bifunctional catalyst. Ind Eng Chem Res 54:6865–6873
Zhao H, Zuo C, Yang D, Li C, Zhang S (2016) Effects of support for vanadium phosphorus oxide catalysts on vapor-phase aldol condensation of methyl acetate with formaldehyde. Ind Eng Chem Res 55:12693–12702
Molino A, Chianese S, Musmarra D (2016) Biomass gasification technology: the state of the art overview. J Energy Chem 25:10–25
Arteaga-Pérez LE, Gómez-Cápiro O, Karelovic A, Jiménez R (2016) A modelling approach to the techno-economics of Biomass-to-SNG/Methanol systems: standalone vs integrated topologies. Chem Eng J 286:663–678
Nebesnyi R (2015) Complex oxide catalysts of acrylic acid obtaining by aldol condensation method. East Eur J Enterp Technol 6:13–16
Dmytruk Yu, Ivasiv V, Nebesnyi R, Maykova S (2015) Optimum conditions determination of methyl methacrylate obtaining over tungsten-containing catalyst. East Eur J Enterp Technol 6:4–7
Nebesna Yu, Ivasiv V, Nebesnyi R (2015) The study of technological and kinetic regularities of simultaneous methacrylates obtaining over zirconium-containing catalysts. East Eur J Enterp Technol 6:49–52
Lapychak N, Ivasiv V, Nebesnyi R, Pikh ZG, Shpyrka II (2016) Synthesis of acrylates from methylpropionate, propionic acid and formaldehyde in the gas phase on solid catalysts. East Eur J Enterp Technol 5(6):44–48
Nebesnyi R, Ivasiv V, Pikh Z, Zhyznevskyi V, Dmytruk Yu (2014) The kinetic of the gas phase aldol condensation reaction of propionic acid with formaldehyde on B2O3–P2O5–WO3/SiO2 catalyst. Chem Chem Technol 8:29–34
Yoo JS (1993) Silica supported metal-doped cesium ion catalyst for methacrylic acid synthesis via condensation of propionic acid with formaldehyde. Appl Catal A 102:215–232
Ludmány A, Kurek SS, Stokłosa A, Wilczynski G, Wójtowicz A, Zaj J (2004) Amorphous titanium hydrogen phosphate—an inorganic sorbent and a catalyst. Appl Catal A 267:149–156
Lin R, Ding Yu (2013) Review on the synthesis and applications of mesostructured transition metal phosphates. Materials 6:217–243
Ai M (1989) Effect of the composition of vanadium-titanium binary phosphate on catalytic performance in vapor-phase aldol condensation. Appl Catal 54:29–36
Ai M, Fujihashi H, Hosoi S, Yoshida A (2003) Production of methacrylic acid by vapor-phase aldol condensation of propionic acid with formaldehyde over silica-supported metal phosphate catalysts. Appl Catal A 252:185–191
Skubiszewska-Zięba J, Khalameida S, Sydorchuk V (2016) Comparison of surface properties of silica xero- and hydrogels hydrothermally modified using mechanochemical, microwave and classical methods. Colloids Surf A 504:139–153
Khalameida S, Sydorchuk V, Skubiszewska-Zięba J, Charmas B, Skwarek E, Janusz W (2017) Hydrothermal, microwave and mechanochemical modification of amorphous zirconium phosphate structure. J Therm Anal Calorim 128:795–806
Przepiera A, Przepiera K, Plaska J (2008) Preparation of titanium (IV) phosphates. Pol J Appl Chem LII 1–2:91–100
Byrappa K, Adschiri T (2007) Hydrothermal technology for nanotechnology. Progr Cryst Growth Charact Mater 53:117–166
Leofanti G, Padovan M, Tozzola G, Venturelli B (1998) Surface area and pore texture of catalysts. Catal Today 41:207–219
Turco M, Ciambelli P, Bagnasco G, Ginestra A, Galli P, Ferragina C (1989) TPD study of NH3 adsorbed by different phases of zirconium phosphate. J Catal 117:355–361
Niwa M, Katada N (2013) New method for the temperature programmed desorption (TPD) of ammonia experiment for characterization of zeolite acidity: a review. Chem Rec 13:432–455
Patrono P, La Ginestra A, Ferragina C, Massucci MA, Frezza A, Vecchio S (1992) Hydrothermal treatment of Zr, Ti, Sn and Ge hydrogen phosphates: characterization of the derived compounds by thermal methods. J Therm Anal Calorim 38:2603–2612
Xi M, Wu L, Li J, Li X (2015) Hierarchical flower-like titanium phosphate derived from H-titanate nanotubes for photocatalysis. J Mater Sci 50:7293–7302
Soria J, Iglesias JE, Sanz J (1993) Effect of calcination on titanium phosphate produced by H3PO4 treatment of anatase. J Chem Soc Faraday Trans 89:2515–2518
Marcu I-C, Sandulescu I, Millet J-MM (2003) Effects of the method of preparing titanium pyrophosphate catalyst on the structure and catalytic activity in oxidative dehydrogenation of n-butane. J Mol Catal A 203:241–250
Leboda R, Charmas B, Sidorchuk VV (1997) Physicochemical and technological aspects of the hydrothermal modification of complex sorbents and catalysts. Part I. Modification of porous and crystalline structures. Adsorpt Sci Technol 15:189–204
Jones JD, Aptel G, Brandhorst M, Jacquin M, Jiménez-Jiménez J, Jiménez-López A, Maireles-Torres P, Piwonski I, Rodríguez-Castellón E, Zajac J, Rozière J (2000) High surface area mesoporous titanium phosphate: synthesis and surface acidity determination. Mater Chem 10:1957–1963
Alam Md, De S, Singh B, Saha B, Abu-Omar M (2014) Titanium hydrogenphosphate: an efficient dual acidic catalyst for 5-hydroxymethylfurfural (HMF) production. Appl Catal A 486:42–48
Nikitina M, Ivanova I (2016) Conversion of 2,3-butanediol over phosphate catalysts. ChemCatChem 8:1346–1353
Paul M, Pal N, Rana BS, Sinha AK, Bhaumik A (2009) New mesoporous titanium–phosphorus mixed oxides having bifunctional catalytic activity. Catal Commun 10:2041–2045
Li CL, Novaro O, Bokhimi X, Munoz E, Boldu JL, Wang JA, Lopez T, Gomez R, Batina N (2000) Coke formation on an industrial reforming Pt–Sn/γ-Al2O3 catalyst. Catal Lett 65:209–216
Wolf EE, Alfani F (1982) Catalysts deactivation by coking. Catal Rev Sci Eng 24:329–371
Leboda R, Charmas B, Sidorchuk VV (1997) Physicochemical and technological aspects of hydrothermal modification of complex sorbents and catalysts. II. Modification of phase composition and mechanical properties. Adsorpt Sci Technol 15:205–214
Hansen TW, Delariva AT, Challa SR, Datye AK (2013) Sintering of catalytic nanoparticles: particle migration or ostwald ripening? Acc Chem Res 46:1720–1730
Argyle MD, Bartholomew CH (2015) Heterogeneous catalyst deactivation and regeneration: a review. Catalysts 5:145–269
Ahmed R, Sinnathambiand CM, Subbarao D (2011) Kinetics of de-coking of spent reforming catalyst. J Appl Sci 11:1225–1230
Li GJ, Zhang XH, Kawi S (1999) Relationships between sensitivity, catalytic activity, and surface areas of SnO2 gas sensors. Sens Actuator B 60:64–70
Hagen J (2015) Industrial catalysis. A practical approach, vol 3rd. Wiley, Weinheim
Vantomme A, Leonard A, Yuan ZY, Su BL (2007) Self-formation of hierarchical micro-meso-macroporous structures: generation of the new concept “Hierarchical Catalysis”. Coll Surf A 300:70–78
Yang XY, Chen LH, Li Y, Rooke JC, Sanchez C, Su BL (2017) Hierarchically porous materials: synthesis strategies and structure design. Chem Soc Rev 46:481–559
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Khalameida, S., Nebesnyi, R., Pikh, Z. et al. Catalytic aldol condensation of formaldehyde with acetic acid on titanium phosphates modified by different techniques. Reac Kinet Mech Cat 125, 807–825 (2018). https://doi.org/10.1007/s11144-018-1443-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11144-018-1443-8