Abstract
The kinetics of oxidation of allyl alcohol to glycidol in the presence of extruded titanium silicalite was investigated. Based on the experimental data obtained, a kinetic model of the process was developed and the activation energies of the target and side reactions, the rate constants and the adsorption equilibrium were determined. Testing of the process of allyl alcohol epoxidation was carried out and the adequacy of the proposed kinetic model was evaluated at the bench laboratory installation of continuous action.
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Seiwert J, Leibig D, Kemmer-Jonas U, Bauer M, Perevyazko I, Preis J et al (2016) Hyperbranched polyols via copolymerization of 1,2-butylene oxide and glycidol: comparison of batch synthesis and slow monomer addition. Macromolecules 49(1):38–47
Wróblewska A, Fajdek A (2010) Epoxidation of allyl alcohol to glycidol over the microporous TS-1 catalyst. J Hazard Mater 179(1):258–265
Sonnati MO, Amigoni S, Taffin de Givenchy EP, Darmanin T, Choulet O, Guittard F (2013) Glycerol carbonate as a versatile building block for tomorrow: synthesis, reactivity, properties and applications. Green Chem 15(2):283–306
Cucciniello R, Pironti C, Capacchione C, Proto A, Di Serio M (2016) Efficient and selective conversion of glycidol to 1,2-propanediol over Pd/C catalyst. Catal Commun 77:98–102
Rider TH, Hill AJ (1930) Studies of glycidol. I. Preparation from glycerol monochlorohydrin. J Am Chem Soc 52(4):1521–1527
Gómez-Jiménez-Aberasturi O, Ochoa-Gómez JR, Pesquera-Rodríguez A, Ramírez-López C, Alonso-Vicario A, Torrecilla-Soria J (2010) Solvent-free synthesis of glycerol carbonate and glycidol from 3-chloro-1,2-propanediol and potassium (hydrogen) carbonate. J Chem Technol Biotechnol 85(12):1663–1670
Cespi D, Cucciniello R, Ricciardi M, Capacchione C, Vassura I, Passarini F et al (2016) A simplified early stage assessment of process intensification: glycidol as a value-added product from epichlorohydrin industry wastes. Green Chem 18(16):4559–4570
Weissermel K, Arpe H-J (2003) Industrial organic chemistry, 4th edn. Wiley-VCH, Weinheim
Kubo M, Nakazawa Y, Takahashi K (1975) Process for preparing glycidol. US patent 3920708
Fisher WC, Linder SM, Pelley RL, Liao H-P (1978) Glycidol process. US patent US4082777
Gade SM, Munshi MK, Chherawalla BM, Rane VH, Kelkar AA (2012) Synthesis of glycidol from glycerol and dimethyl carbonate using ionic liquid as a catalyst. Catal Commun 27:184–188
Endah YK, Kim MS, Choi J, Jae J, Lee SD, Lee H (2017) Consecutive carbonylation and decarboxylation of glycerol with urea for the synthesis of glycidol via glycerol carbonate. Catal Today 293–294:136–141
Wang L, Zhou Y, Mi Z (2007) Epoxidation of allyl chloride and hydrogen peroxide over titanium silicalite-1 film on SiO2 pellet support. J Chem Technol Biotechnol 82(4):414–420
Harvey L, Kennedy E, Dlugogorski BZ, Stockenhuber M (2015) Influence of impurities on the epoxidation of allyl alcohol to glycidol with hydrogen peroxide over titanium silicate TS-1. Appl Catal A 489:241–246
Přech J (2018) Catalytic performance of advanced titanosilicate selective oxidation catalysts—a review. Catal Rev 60(1):71–131
Cavani F, Teles JH (2009) Sustainability in catalytic oxidation: an alternative approach or a structural evolution? ChemSusChem 2(6):508–534
Cavani F (2010) Catalytic selective oxidation: the forefront in the challenge for a more sustainable chemical industry. Catal Today 157(1):8–15
Perego C, Carati A, Ingallina P, Mantegazza MA, Bellussi G (2001) Production of titanium containing molecular sieves and their application in catalysis. Appl Catal A 221(1):63–72
Hammond C, Padovan D, Tarantino G (2018) Porous metallosilicates for heterogeneous, liquid-phase catalysis: perspectives and pertaining challenges. R Soc Open Sci 5(2):171315
Wróblewska A, Ławro E, Milchert E (2006) Technological parameter optimization for epoxidation of methallyl alcohol by hydrogen peroxide over TS-1 catalyst. Ind Eng Chem Res 45(22):7365–7373
Wróblewska A, Milchert E (2007) Epoxidation of allyl alcohol with hydrogen peroxide over titanium silicalite TS-2 catalyst. J Chem Technol Biotechnol 82(7):681–686
Wróblewska A, Fajdek A, Wajzberg J, Milchert E (2008) Epoxidation of allyl alcohol to glycidol over titanium-silicalite Ti-beta and Ti-MCM-41 catalysts. J Adv Oxid Technol 105:451–468
Wróblewska A, Fajdek A, Wajzberg J, Milchert E (2009) Epoxidation of allyl alcohol over mesoporous Ti-MCM-41 catalyst. J Hazard Mater 170(1):405–410
Taramasso M, Perego G, Notari B (1983) Preparation of porous crystalline synthetic material comprised of silicon and titanium oxides. US patent 4410501
Kraushaar B, Van Hooff JHC (1988) A new method for the preparation of titanium-silicalite (TS-1). Catal Lett 1(4):81–84
Gao H, Suo J, Li S (1995) An easy way to prepare titanium silicalite-1 (TS-1). J Chem Soc Chem Commun 8:835
Serrano DP, Uguina MA, Ovejero G, Van Grieken R, Camacho M (1995) Synthesis of TS-1 by wetness impregnation of amorphous SiO2–TiO2 solids prepared by the sol-gel method. Microporous Mater 4(4):273–282
Uguina MA, Serrano DP, Ovejero G, Van Grieken R, Camacho M (1995) Preparation of TS-1 by wetness impregnation of amorphous SiO2–TiO2 solids: influence of the synthesis variables. Appl Catal A 124(2):391–408
Gontier S, Tuel A (1996) Synthesis of titanium silicalite-1 using amorphous SiO2 as silicon source. Zeolites 16(2):184–195
Gang L, Xinwen G, Xiangsheng W, Qi Z, Xinhe B, Xiuwen H et al (1999) Synthesis of titanium silicalites in different template systems and their catalytic performance. Appl Catal A 185(1):11–18
Kim KY, Ahn WS, Park DW, Oh JH, Lee CM, Tai WP (2004) Microwave synthesis of titanium silicalite-1 using solid phase precursors. Bull Korean Chem Soc 25(5):634–638
Ahn W-S, Lee K-Y (2005) Extensions in the synthesis and catalytic application of titanium silicalite-1. Catal Surv Asia 9(1):51–60
Chen P, Chen X, Tanaka K, Kita H (2007) A novel and less-expensive preparation of titanium silicalite-1 membrane. Chem Lett 36(8):1078–1079
Wróblewska A, Milchert E (2004) Optimization of the reaction parameters of epoxidation of allyl alcohol with hydrogen peroxide on TS-1 catalyst. Chem Pap 58(4):247–255
Clerici MG, Bellussi G, Romano U (1991) Synthesis of propylene oxide from propylene and hydrogen peroxide catalyzed by titanium silicalite. J Catal 129(1):159–167
Danov SM, Sulimov AV, Ovcharov AA, Sulimova AV (2011) Method of producing granular titanium-containing zeolite. RU patent RU2422360
Danov SM, Sulimov AV, Kolesnikov VA, Ovcharov AA (2013) Kinetics of propylene epoxidation with hydrogen peroxide. Kinet Catal 54(2):193–198
van der Pol AJHP, van Hooff JHC (1992) Parameters affecting the synthesis of titanium silicalite 1. Appl Catal A 92(2):93–111
Keshavaraja A, Ramaswamy V, Soni HS, Ramaswamy AV, Ratnasamy P (1995) Synthesis, characterization, and catalytic properties of micro-mesoporous, amorphous titanosilicate catalysts. J Catal 157(2):501–511
Li YG, Lee YM, Porter JF (2002) The synthesis and characterization of titanium silicalite-1. J Mater Sci 37(10):1959–1965
Kafarov VV (1985) Metody kibernetiki v khimii i khimicheskoi tekhnologii (methods of cybernetics in chemistry and chemical engineering). Khimiya, Moscow
Bottino A, Capannelli G, Comite A, Storace S, Di Felice R (2003) Kinetic investigations on the oxidehydrogenation of propane over vanadium supported on γ-Al2O3. Chem Eng J 94(1):11–18
Sridevi U, Bhaskar Rao BK, Pradhan NC (2001) Kinetics of alkylation of benzene with ethanol on AlCl3-impregnated 13X zeolites. Chem Eng J 83(3):185–189
Lebedev NN, Manakov MN, Shvets VF (1984) Teoriya khimicheskikh protsessov osnovnogo organicheskogo i neftekhimicheskogo sinteza (theory of chemical processes in basic organic and petrochemical syntheses). Khimiya, Moscow
Sulimov AV, Danov SM, Ovcharova AV, Flid VR, Bruk LG (2017) A kinetic model for the epoxidation of allyl alcohol with hydrogen peroxide on titanium silicate TS-1. Kinet Catal 58(6):673–678
Luchinskii GP (1971) Khimiya titana (the chemistry of titanium). Khimiya, Moscow
Zhorov YM (1989) Kinetika promyshlennykh organicheskikh reaktsii (kinetics of industrial organic reactions). Khimiya, Moscow
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The work is executed at financial support of the Ministry of Education and Science of the Russian Federation (Agreement No. 14.577.21.0093 for a subvention, a unique identifier of applied research (Project) RFMEFI57714X0093).
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Sulimov, A., Ovcharova, A., Ovcharov, A. et al. Kinetics of Allyl Alcohol Epoxidation with Hydrogen Peroxide Catalyzed by a TS-1/Al2O3. Catal Lett 149, 3076–3086 (2019). https://doi.org/10.1007/s10562-019-02877-6
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DOI: https://doi.org/10.1007/s10562-019-02877-6