Luận án Synthesis of catalysts based on Pt/SBA - 15 modified with Al and/or B and their applicability on n - heptane hydroisomerization, tetralin hydrogenation and paracetamol detection

96.94 °C Peak :377.31 °C Figure: 20/12/2019 Mass (mg): 9.36 Crucible:PT 100 µl Atmosphere:AirExperiment:HienQNU SC2 Procedure: RT ----> 900C (10 C.min-1) (Zone 2)Labsys TG (B) Furnace temperature /°C0 100 200 300 400 500 600 700 TG/% -4 -3 -2 -1 0 1 2 3 4 5 d TG/% /min -1.8 -1.6 -1.4 -1.2 -1.0 -0.8 -0.6 -0.4 -0.2 Mass variation: -1.60 % Mass variation: -2.76 % Peak :83.13 °C Peak :362.47 °C Figure: 20/12/2019 Mass (mg): 14.21 Crucible:PT 100 µl Atmosphere:AirExperiment:HienQNU SC3 Procedure: RT ----> 900C (10 C.min-1) (Zone 2)Labsys TG (C) 82 At the reaction condition, coke formation is due to the adsorption and condensation on acid sites of unsaturated compounds [133]. All TGA curves showed low weight losses. The weight losses at low temperature (< 100 oC) correspond to desorption of physically adsorbed water. The weight losses at higher temperatures are due to combustion of coke forms onto the surface of the used catalysts. The results of coke formation were agreement with the different acidity of catalysts. The catalysts containing boron showed the less content of coke. 3.6. The mesoporous catalysts of Pt loaded on modified SBA-15 material for the paracetamol detection The previous sections showed the efficient catalytic activity of the 0.5% Pt supported on modified SBA-15 material for the hydroisomerization and the hydrogenation. Motivated by these results, the investigated catalysts above were expected to be active catalysts in electrochemical processes. However, the very low peak currents of paracetamol (PA) were observed when the 0.5%Pt/M-SBA-15-GPE (where M=Al and/or B) electrodes were employed. Thus, the Pt-based catalysts with 1% Pt were prepared and applied in the detection of PA. Fig 3.27. Square wave voltammograms of 10-5M PA at the 1%Pt/M-SBA-15-GPE (where M=Al and/or B) electrodes in 0.1M phosphate buffer (pH=7). 83 Peak currents of paracetamol were obtained from square wave voltammograms recorded at the 1%Pt/M-SBA-15-GPE (where M=Al and/or B) electrodes in the presence of 10-5M PA. The results (Fig 3.27) showed the maximum peak current were observed at 1% Pt/Al-SBA-15-GPE electrode. Therefore, this electrode was selected for investigations of electrochemical behavior and analytical characterization. 3.6.1. Characterization of 1%Pt/Al-SBA-15 catalyst Textural characteristics of the 1% Pt/Al-SBA-15 material was determined by XRD patterns, BET results, TEM images and ICP. The low-angle XRD patterns of 1%Pt/Al-SBA-15 catalyst (Fig. 3.28) showed an intense main diffraction peak and two weak peaks, which are associated with (100), (110), (200) planes reflections respectively, indicating their ordered hexagonal mesoporous structure. Fig 3.28. Low angle XRD pattern of 1%Pt/Al-SBA-15 catalyst N2 adsorption–desorption isotherms of Pt/Al-SBA-15 catalyst (Fig. 3.29) showed type IV isotherms with H1 hysteresis loop, which corresponds to mesoporous materials consisting of well-defined cylindrical channels. Physico-chemical parameters of Al-SBA-15 support and Pt/Al-SBA-15 catalyst were presented in Table 3.11. It can be seen from table 3.11 that the BET surface area and pore size distribution decreased after introduction of platinum to the Al-SBA-15 support. This implied that the pore 84 surface was loaded with Pt nanoparticles. Platinum content of 0.89 % was measured by inductively coupled plasma (ICP) method for Pt/Al-SBA-15 catalyst. Fig 3.29. Nitrogen adsorption-desorption isotherms at 77K (A) and pore size distribution (B) applying BJH method in the desorption branch of 1%Pt/Al-SBA-15 catalyst. Table 3.11. Surface area and pore size of Al-SBA-15 support and 1%Pt/Al-SBA-15 catalyst Samples SBET, m2/g Pore size, Å Pt content, % (ICP) Al-SBA-15 736.3 58 --- 1%Pt/Al-SBA-15 522.05 56 0.89 TEM images of Pt/Al-SBA-15 catalyst showed highly ordered hexagonal arrays of the mesopores with uniform pore size (Fig. 3.30). This result is in accordance with low angle XRD pattern and BET result. Small black dots appeared in TEM image with particle size of 2 – 5 nm confirmed platinum particles on the surface of catalyst. (B) (A) 85 Fig 3.30. TEM image of 1% Pt/Al-SBA-15 catalyst. The characterization of the 1% Pt/Al-SBA-15 catalyst determined by XRD, TEM, BET, ICP showed that the hexagonal mesoporous structure of the investigated catalysts was not affected. The introduction of platinum led to the formation of Pt nanoparticles over and inside the mesoporous structure and decreased the surface area. 3.6.2. Electrochemical characterization of 1%Pt/Al-SBA-15-GPE electrode material The electrochemical characterization of 1% Pt/Al-SBA-15-GPE electrode material was studied using cyclic voltammetry. Fig. 3.31 showed the CV curves recorded at the Pt/l-SBA-15-GPE electrode in the absence and in the presence of 7.10-6 M PA. CV curves from Fig 3.31 showed a peaks pair due to the oxidation of PA which are placed at following anodic/cathodic potentials (Epa/Epc): +0.425/+0.312 V for Pt/Al- SBA-15-GPE and +0.5/+0.22 V for GPE, respectively. The similar behavior was recorded in the same potential windows at MCPE-PtMWCNTs–TX100 (i.e.: Epa = 0.362 V and Epc = 0.311 V) [92]. The electrochemical parameters of the investigated electrode material were summarized in Table 3.12. 86 Fig. 3.31. Cyclic voltammograms at Pt/Al-SBA-15-GPE in absence (dot line) and in presence of 7 x 10-5 M of PA (solid line). Inset: CV at unmodified GPE in presence of 7 M of PA. Table 3.12. The electrochemical parameters of the 1%Pt/Al-SBA-15-GPE electrode material. Electrode ΔE, V Eo’, V Ipa/Ipc FWHM, mV GPE +0.28 +0.36 3.55 83 1%Pt/Al-SBA-15-GPE +0.113 +0.369 1.99 107 The diminution of the Ipa/Ipc ratio value at Pt/Al-SBA-15-GPE electrode, suggesting that the presence of Pt nanoparticles of in the sensing matrix (Pt/Al-SBA- 15-GPE) improve the reversibility of the studied electron transfer reaction. The same reason could justify the increase of peak currents of PA at Pt/Al-SBA-15-GPE electrode matrix, comparing with the current recorded at unmodified GPE. The full width at half of the peak maximum height (FWHM) is 107 mV and 83 mV for Pt/Al-SBA-15-GPE modified electrode and GPE unmodified electrode, respectively. These values of FWHM which were different from theoretical FWHM (90.6/n [mV]) have been attributed to electrostatic effects due to the presence of adjacent charged species [137]. 87 Effect of scan rate The influence of the potential scan rate on the voltammograms of PA at 1%Pt/Al-SBA-15-GPE (Fig 3.32) showed a shift towards positive and negative direction of the anodic and cathodic potential peak respectively when the scan rate increased. Fig 3.32. Cyclic voltamogramms of 7 x 10-5 M PA at 1%Pt/Al-SBA-15-GPE recorded at different scan rate. Inset influence of scan rate on anodic peak currents intensities at Pt/Al- SBA-15-GPE () and GPE () electrodes (A). From Table 3.13, the log I - log v dependency for the oxidation/reduction peak has a slope which is close to the theoretical value from the well-known Randles-Ševcik equation (i.e., 0.5). This behaviour indicated a diffusion-controlled redox process of PA occurring to the Pt/Al-SBA-15-GPE modified electrode [95][96]. The obtained results for the electrochemical parameters demonstrated the obvious electrocatalytic properties of Pt/Al-SBA-15-GPE electrode for the PA redox process. The obtained electrochemical activity were improved by Pt NPs free active sites and mesoporous structure of catalyst distributed on the electrode surface and requested for an enhanced electron transfer process. 88 Table 3.13. Slope of log I versus log v dependence. Electrode type Slope of log I - log v dependence anodic R2/n GPE 0.491 ± 0.011 0.9969/14 Pt/Al-SBA-15-GPE 0.418 ± 0.024 0.9823/13 3.6.3. Electrochemical impedance spectroscopy measurements at 1%Pt/Al-SBA-15-GPE electrode The Nyquist plots recorded in a redox probe of 1 mM K3[Fe(CN)]6/K4[Fe(CN)]6 at 1%Pt/Al-SBA-15-GPE and GPE electrodes, respectively, are shown in Fig 3.33. The depressed semicircle observed at Pt/Al-SBA- 15-GPE interface is characteristic to porous materials [138], indicating low interfacial electron transfer resistance and good conductivity. Contrarily, at GCE electrode a remarkable capacitive loop is present. Figure 3.33. Nyquist plots recorded at 1%Pt/Al-SBA-15-GPE modified electrode () and GPE unmodified electrode () (inset) into a solution containing 1 mM K4[Fe(CN)6]/K3[Fe(CN)6] + 0.1 M phosphate buffer (pH 7). 89 Both equivalent electric circuit (Rsol(CPEdl(RctW)) for GPE electrode and Rsol(CPEpore(Rpore(CPEdl(RctW)))) for Pt/Al-SBA-15-GPE modified electrode) were used for fitting the obtained experimental data. The EIS fitting parameters are given in Table 3.14. Table 3.14. EIS fitting parameters for Pt/Al-SBA-15-GPE modified electrodes. EIS parameters GPE Pt/Al-SBA-15-GPE Rsol (Ω cm2) 13.36 ± 1.24 31.24 ±2.77 CPEpore (S s n/cm2) - 142.6 10-5 ± 24.14 n1 - 0.496 Rpore (Ω cm2) - 33.12 ± 6.61 CPEdl(S s n/cm2) 1.127 10-5 ±1.71 70.49 10-3 ±10.98 n2 0.905 1 Rct (Ω) 3917 ± 0.76 273 ± 8 W (S s1/2 / cm2) 337.4 10-5 ± 6.98 529.6 ±10-5 + 34 chi2 0.629 10-3 0.964 10-3 ± values are relative standard errors expressed as %. As expected, at GPE the great Rct value indicates a hindering of the electron transfer process, while a 10 times decrease of the Rct was obtained at Pt/Al-SBA-15- GPE modified electrode pointing out an easy electron transfer occurring at electrode interface. The reason might be due to the presence of Pt nanoparticles and/or of the mesoporous structure of the Pt/Al-SBA-15 material. 3.6.4. Analytical characterization of 1%Pt/Al-SBA-15-GPE electrode material Calibration curve The quantitative analysis of PA was carried out using the Pt/Al-SBA-15-GPE modified electrode by square wave voltammetry (Fig 3.34). The calibration curve shows excellent linearity over a concentration range 10-6 –10-5 M PA. 90 The linear regression equations are: I/A = (-8.36 10-7 ± 2.66 10-7) + (1.68 ± 0.04 ) [PA]/M (R = 0.9968, n = 11 points) and I/A = (2.8 10-9 ± 3.07 10-9) + (29.9 10-3 ± 0.5 10-3) [PA]/M (R = 0.9986, n = 10 points) at Pt/Al-SBA-15-GPE modified electrode and GPE, respectively. Fig 3.34. Square wave voltamogramms for different concentration of PA at Pt/Al-SBA-15- GPE modified graphite paste electrode (A) and calibration curve of Pt/Al-SBA-15-GPE modified graphite paste electrode () and GPE () for PA (B). Compared with the unmodified GPE electrode, the sensitivity of the Pt/Al-SBA- 15-GPE modified electrode was increased approximatively 60 times. This could be due to the presence of Pt nanoparticles and mesoporous structure of Pt/Al-SBA-15 catalyst in the electrode matrix. The estimated detection limit (for a signal-to-noise ratio S/N = 3) were 0.85 M at Pt/Al-SBA-15-GPE modified electrode. The obtained value are lower comparatively with some reported in the literature : 1.1 M at CPE-CNT-poly(3- aminophenol) [101]; 1.39 M at PEDOT/SPE [139]; 6 M at graphene oxide-GCE [140]. (B) (A) 91 3.6.5. Interference study To investigate the interference for the determination of PA, the oxidation peak of 7 M PA was measured in the presence of different concentrations of the most common interference compounds like: 1 mM or 2 mM ascorbic acid (AA) and 3 M or 5 M uric acid (UA). Square wave voltamogramms at the investigated modified electrode were given in Fig 3.36. Fig 3.35. Square wave voltamogramms recorded at 1%Pt/Al-SBA-15-GPE modified electrode in a presence of a mixture of 7 x 10-6 M paracetamol, 9 x 10-3 M ascorbic acid and 10-6 M uric acid. The possible interference for the determination of PA was also studied, under the same experimental conditions. Thus, the oxidation peak of 7 M PA was individually measured in the presence of different concentrations of the most common interferents like: 0.9 mM ascorbic acid and 1 M uric acid. As seen in Fig 3.36, there is almost no influence on the detection of PA, because the peaks corresponding to the interfering compounds appear completely separated from the oxidation peak of PA. UA AA PA 92 3.6.6. Real sample analysis The Pt/Al-SBA-15-GPE modified electrode was used to estimate the PA concentration in different commercial tablets, using the standard addition method, appropriate when samples have complex matrices. Fig 3.36. SWVs (A) and calibration curve (B) for detection of PA from tablets using 1%Pt/Al -SBA-15-GPE modified electrode. (B) (A) 93 Table 3.15. Determination of PA from pharmaceutical tablets using 1%Pt/Al-SBA-15-GPE modified electrode Sample Added, µM Found, µM Recovery, % RSD, % PA (500 mg/tablet) 5 4.95 ± 0.13 99.6 ± 2.61 2.63 SWV measurements were performed under similar experimental conditions as for the electrode calibration against PA. The same analysis was performed using three different Pt/Al-SBA-15-GPE electrodes and the obtained data were used to calculate the average value of the PA concentration for the analyzed samples. The results were found in very good agreement with those obtained by the pharmaceutical tablets producer (Table 3.15). It was found that the recovery of PA was in the range of 96.99 – 102.21 %. The relative standard deviation (RSD) was smaller than 3%. The excellent average recoveries of formulation tablets samples suggest that the Pt nanoparticles present in the electrode matrix (Pt/Al-SBA-15-GPE) is able to be used for PA detection from pharmaceutical tablets. 94 CONCLUSIONS 1. The incorporation of Al and/or B into SBA-15 framework did not affect the structure and morphology of SBA-15 mesoporous material but created acid sites on their surfaces. The further loading of platinum on the modified supports caused a decrease of the surface area, but the ordered hexagonal mesoporous structure of SBA- 15 material remained unchanged. The presence of both Al and B in a ratio of 0.5:0.5 created a highest acidity for Al-B-SBA-15 support and the corresponding catalyst of Pt/Al-B-SBA-15. The acidic properties of modified supports played a crucial role in the catalytic behaviour of the Pt/M-SBA-15 catalysts (where M = Al and/or B). 2. The studies of the hydroisomerization of n-heptane indicated that all of investigated catalysts exhibited the good catalytic activity in the reaction condition of temperature (200-300oC), range of reaction time (24 hours). The best conversion of n- heptane was reached at 39% over the Pt/Al-B-SBA-15 catalyst at 300 oC, 30 at after reaction time of 24 hours. These catalysts showed high selectivity for the isomerization to methylhexanes. Dimethylpentanes was also produced but in a different extent, depending on the acidity of the support. Yield of cracked products and coke formation were smaller than 5 % after the reaction time of 24 hours. 3. At the condition of temperature (180-220 oC), hydrogen pressure (15-25 at), reaction time of 3 hours, the three investigated catalysts were also employed successfully in the hydrogenation of tetralin to cis- and trans-decalin. The maximum tetralin conversion of 31.4 % and the cis/trans-decalin ratio of 2.3 are reached over the Pt/Al-B-SBA-15 catalyst at 200 oC and 20 at. 4. The mesoporous 1%Pt/Al-SBA-15 catalyst was used to prepare the modified electrode material. The electrochemical behavior of PA at 1%Pt/Al-SBA-15-GPE modified electrode was investigated by CV, SWV and EIS. The analytical parameters showed a linearity over concentration range of 10-6 M – 10-5 M PA, sensibility of 1.68 A/M, detection limit of 0.85 µM, no interference. The 95 recovery of PA in real sample was in the range 96.99% - 102.21% corresponding to the relative standard deviation was smaller than 3%. The obtained results showed the electro-catalytic activity of 1%Pt/Al-SBA-15 material and its potential application for PA detection in real samples 96 PUBLICATIONS OF THE DISSERTATION 1. Ngô Thị Thanh Hiền, Trần Văn Lâm, Phạm Trung Kiên, Nguyễn Thị Tâm, Nguyễn Hồng Lê, Trần Thị Thúy Hiền, Nguyễn Thị Hà Hạnh, Nguyễn Anh Vũ, Phạm Thanh Huyền (2017), “Nghiên cứu ảnh hưởng của boron tới đặc trưng xúc tác Pt/B-SBA-15 cho phản ứng hydro hóa tetralin”, Tạp chí dầu khí, số 9, 30-38 2. Ngo Thi Thanh Hien, Le Van Tuyen, Nguyen Van Tuan, Pham Thanh Huyen (2018), “Direct hydrothermal synthesis and post-synthesis grafting of boron onto SBA- 15: influence of synthesis method on the support of Pt containing catalyst for the hydrogenation of tetralin”, Vietnam Journal of Catalysis and Adsorption, 7-issue 3, 52-57. 3. Ngo Thi Thanh Hien, Pham Trung Kien, Nguyen Anh Vu, Pham Thanh Huyen (2019), “Direct synthesis of Al-B-SBA-15 and its application for Pt bifunctional catalyst in the hydrogenation of tetralin”, Catalysis In Industry, Vol 11, No 1, 59-64 (SCI). 4. C. Rizescu, B. Cojocaru, N.T. Thanh Hien, P.T.Huyen, V.I. Parvulescu (2019), “Synergistic B-Al interaction in SBA-15 affording an enhanced activity for the hydro- isomerization of heptane over Pt-B-Al-SBA-15 catalysts”, Microporous and Mesoporous Materials, Vol 281, 142-147 (SCI). 5. Thi Thanh Hien Ngo, I. C. Fort, Thanh Huyen Pham, G. L. Turdean (2020), “Paracetamol detection at a graphite paste modified electrode based on platinum nanoparticles immobilized on Al-SBA-15 composite material”, Studia UBB Chemia, LXV, 1, 27-38 (SCI) 97 REFERENCES [1] D. Zhao, J. Feng, Q. Huo, N. Melosh, G. H. Fredrickson, B. F. Chmelka, G. D. Stuky (1998), “Triblock copolymer syntheses of mesoporous silica with periodic 50 to 300 angstrom pores,” Science, vol. 279, no. 5350, pp. 548–552. [2] J. S. Beck, J. C. Vartuli, W. J. Roth, M. E. Leonowicz, C. T. Kresge, K. D. Schmitt, C. T-W. Chu, D. H. Olson, E. W. Shelppard, S. B. Mocullen, J. B. Higgins, J. L. Schlenker (1992), “A New Family of Mesoporous Molecular Sieves Prepared with Liquid Crystal Templates,” J. Am. Chem. Soc., vol. 114, no. 27, pp. 10834–10843. [3] I. Rustamov, T. Farcas, F. Ahmed, F. Chan, R. LoBrutto, H. M. McNair, Y. V. Kazakevich (2001), “Geometry of chemically modified silica,” J. Chromatogr. A, vol. 913, no. 1–2, pp. 49–63. [4] K. K. Kang and H. K. Rhee (2005), “Synthesis and characterization of novel mesoporous silica with large wormhole-like pores: Use of TBOS as silicon source,” Microporous Mesoporous Mater, vol. 84, no. 1–3, pp. 34–40. [5] G. L. Athens, R. M. Shayib, and B. F. Chmelka (2009), “Functionalization of mesostructured inorganic-organic and porous inorganic materials,” Curr. Opin. Colloid Interface Sci, vol. 14, no. 4, pp. 281–292. [6] A. Walcarius and L. Mercier (2010), “Mesoporous organosilica adsorbents: Nanoengineered materials for removal of organic and inorganic pollutants,” J. Mater. Chem, vol. 20, no. 22, pp. 4478–4511. [7] A.M.Veneziaa; G.Di Carlo; L.F.Liottaa; G.Pantaleoa; M.Kantcheva (2011), “Effect of Ti(IV) loading on CH4 oxidation activity and SO2 tolerance of Pd catalysts supported on silica SBA-15 and HMS,” Appl. Catal. B Environ., vol. 6, no. 3–4, pp. 529–539. [8] G. S. Mishra, K. Machdo, A. Kumar (2014), “Highly selective n-alkanes oxidation to ketones with molecular oxygen catalyzed by SBA-15 supported rhenium catalysts,” J. Ind. Eng. Chem., vol. 20, no. 4, pp. 2228–2235. [9] L. ‐X. Zhang, J. ‐L. Shi, J. Yu, Z. ‐L. Hua, X. ‐G. Zhao, M. ‐L. Ruan (2002), “A 98 New In‐Situ Reduction Route for the Synthesis of Pt Nanoclusters in the Channels of Mesoporous Silica SBA‐15,” Adv. Mater., vol. 14, pp. 1510–1513. [10] X. Wang, K. S. K. Lin, J. C. C. Chan, S. Cheng (2005), “Direct Synthesis and Catalytic Applications of Ordered Large Pore Aminopropyl-Functionalized SBA- 15 Mesoporous Materials,” J. Phys. Chem. B, vol. 109, pp. 1763–1769. [11] C. Haribandhu, D. Subhajit, S. Ashis (2015), “Synthesis and use of SBA-15 adsorbent for dye-loaded wastewater treatment,” J. Environ. Chem. Eng., vol. 3, no. 4, pp. 2866–2874. [12] L. E. Tummino M.L, Testa M.L, Malandrino M, Gamberini R, Prevot A.B, Magnacca G (2019), “Green Waste-Derived Substances Immobilized on SBA-15 Silica: Surface Properties, Adsorbing and Photosensitizing Activities towards Organic and Inorganic Substrates,” Nanomaterials, vol. 9, p. 162. [13] A. Szewczyk, M. Prokopowicz (2018), “Amino-modified mesoporous silica SBA- 15 as bifunctional drug delivery system for cefazolin: Release profile and mineralization potential,” Mater. Lett, vol. 227, pp. 136–140. [14] B. Dragoi, E. Dumitriu, C. Guimon, and A. Auroux (2009), “Microporous and Mesoporous Materials Acidic and adsorptive properties of SBA-15 modified by aluminum incorporation,” Microporous Mesoporous Mater., vol. 121, no. 1–3, pp. 7–17. [15] I. Eswaramoorthi and A. K. Dalai (2006), “Synthesis , characterisation and catalytic performance of boron substituted SBA-15 molecular sieves,” Microporous Mesoporous Mater, vol. 93, pp. 1–11. [16] J. Du, H. Xu, J. Shen, and J. Huang (2005), “Catalytic dehydrogenation and cracking of industrial dipentene over M / SBA-15 ( M = Al , Zn ) catalysts,” Appl. Catal. A, vol. 296, pp. 186–193. [17] R. Van Grieken, J. M. Escola, J. Moreno, and R. Rodríguez (2009), “Direct synthesis of mesoporous M-SBA-15 ( M = Al , Fe , B , Cr ) and application to 1- hexene oligomerization,” Chem. Eng. J., vol. 155, pp. 442–450. [18] L. Chen, M. Zhang, Y. Yue, C. Ye, and F. Deng (2004), “NMR and theoretical 99 studies of boron-modified mordenite,” Microporous Mesoporous Mater, vol. 76, no. 1–3, pp. 151–156. [19] Z. Sba-, K. Szczodrowski, B. Prélot, S. Lantenois, J. Douillard, and J. Zajac (2009), “Microporous and Mesoporous Materials Effect of heteroatom doping on surface acidity and hydrophilicity,” Microporous Mesoporous Mater, vol. 124, no. 1–3, pp. 84–93. [20] V. A. Vallés, B. C. Ledesma, G. A. Pecchi, O. A. Anunziata, and A. R. Beltramone (2017), “Hydrogenation of tetralin in presence of nitrogen using a noble-bimetallic couple over a Ti-modified SBA-15,” Catal. Today, vol. 282, pp. 111–122. [21] H. W. Lee, J-K. Jeon, K-E. Jeong, S. Y. Jeong, J. Han, B. Seo, Y. H. Joo, Y. K. Park (2013), “Effect of Pt particle size on the hydroisomerization of n-dodecane over Pt/Al-SBA-15 catalysts,” J. Nanosci. Nanotechnol, vol. 13, no. 9, pp. 6074– 6078. [22] P. T. Huyen, L. T. H. Nam, T. Q. Vinh, C. Martínez, and V. I. Parvulescu (2018), “ZSM-5 / SBA-15 versus Al-SBA-15 as supports for the hydrocracking / hydroisomerization of alkanes,” Catal. Today, vol. 306, no. January 2017, pp. 121–127. [23] Hoàng Văn Đức, Nguyễn Thị Anh Thư, Đặng Tuyết Phương, Nguyễn Hữu Phú (2010), “Tổng hợp vật liệu mao quản trung bình SBA-15 chứa nhóm thiol (-SH) và hoạt tính hấp phụ ion Pb2+ trong dung dịch nước,” Tạp chí hóa học, vol. 49, no. 3, pp. 347–351. [24] Phan Thanh Son Nam, Nguyen Thi Quynh Ngoc (2012), “Microwave-Assisted Suzuki Reaction Using Palladium Complex Immobilized on Sba-15 As an Efficient,” Vietnam J. Chem., vol. 50, no. October, pp. 601–608. [25] Đinh Quang Khiếu, Lê Thanh Sơn (2008), “Nghiên cứu động học của phản ứng oxi hóa phenol đỏ trên xúc tác Fe-SBA-15,” Tạp chí hóa học, vol. 2, pp. 211– 216. [26] Đặng Tuyết Phương, Hoàng Yến, Đinh Cao Thắng, Bùi Hải Linh, Nguyễn Hữu 100 Phú (2006), “Tổng hợp, đặc trưng vật liệu mao quản nano Al-SBA-15 có tỷ số Si- Al khác nhau,” in Hội nghị khoa học lần thứ 20 - Đại học Bách Khoa Hà Nội, 2006, pp. 34–37. [27] Hoàng Văn Đức, Đặng Tuyết Phương, Nguyễn Hữu Phú (2007), “Nghiên cứu tính chất hóa lý của vật liệu mao quản trung bình Ti-SBA-15 được tổng hợp bằng phương pháp trực tiếp,” Tạp chí hóa học, vol. 45, no. 5, pp. 595–599. [28] Nguyễn Thị Hồng Hoa, Đặng Tuyết Phương, Nguyễn Thị Ngọc Linh (2013) “Tổng hợp vật liệu mao quản trung bình SBA-15 sử dụng làm chất mang cố định enzym DAAO,” Tạp chí Khoa học và Công nghệ, vol. 2, no. 12, pp. 15–19. [29] Tuyet Phuong D., Anh Tuan V., Gia Thanh V., Vinh Thang H., Cao Thang D., Hoang Yen, Kim Hoa T., Kim Lan L., Huu Phu N (2006), “Photocatalytic oxidation of phenylsulfophtalein by hydrogen peroxide over Ti containing SBA- 15 mesoporous materials,” Study Surf. Scien Catal., vol. 165, pp. 663–666. [30] Nguyen Tien Thao, Bui The Thien, Pham Thi Hien, Nguyen Thi Nhu (2016) “Oxidation of styrene with hydrogen peroxide over Cu/SBA-15 catalyst,” Vietnam J. Chem., vol. 54, pp. 133–138. [31] Trần Văn Nhân, Hoàng Hiệp, Hoa Hữu Thu, Lê Thanh Sơn, Khúc Quang Đạt (2008), “Tổng hợp và nghiên cứu xúc tác Cu/SBA-15 trong phản ứng oxi hóa hoàn toàn LPG,” Tạp chí hóa học, vol. 46, no. 4, pp. 411–415. [32] Ngô Thị Thuận, Phạm Xuân Núi (2007), “Xúc tác Pt/WO3-ZrO2 trên vật liệu mao quản trung bình SBA-15 trong phản ứng isome hóa n-heptan,” Tạp chí hóa học, vol. 45, no. 1, pp. 77–82. [33] A. Goguet, S. Shekhtman, F. Cavallaro, C. Hardacre, and F. C. Meunier (2008), “Effect of the carburization of MoO3-based catalysts on the activity for butane hydroisomerization,” Appl. Catal. A Gen, vol. 344, no. 1–2, pp. 30–35. [34] W. Wang, C.-J. Liu, and W. Wu (2019), “ Bifunctional catalysts for the hydroisomerization of n -alkanes: the effects of metal–acid balance and textural structure ,” Catal. Sci. Technol., vol. 9, no. 16, pp. 4162–4187. [35] K. Park and S. Ihm (2000), “Comparison of Pt / zeolite catalysts for n - 101 hexadecane hydroisomerization,” Appl. Catal. A, vol. 203, pp. 201–209. [36] M. Guisnet (2013), “‘ Ideal ’ bifunctional catalysis over Pt-acid zeolites,” Catal. Today, vol. 218–219, pp. 123–134. [37] P. Liu, J. Wang, and R. Wei, X. Ren, X. Zhang (2008), “A Highly Efficient H β Zeolite Supported Pt Catalyst Promoted by Chromium for the Hydroisomerization of n -Heptane A Highly Efficient H b Zeolite Supported Pt Catalyst Promoted by Chromium for the Hydroisomerization of n -Heptane,” Catal Lett, 126, pp 346-352. [38] A. De Lucas, P. Sa, A. Fu, and L. Valverde (2006), “Liquid-Phase Hydroisomerization of n -Octane over Platinum-Containing Zeolite-Based Catalysts with and without Binder,” Ind. Eng. Chem. Res, vol. 45, pp. 8852– 8859. [39] H. Deldari (2005), “Suitable catalysts for hydroisomerization of long-chain normal paraffins,” Appl. Catal. A, vol. 293, pp. 1–10. [40] M. A. Arribas, F. Márquez, and A. Martínez (2000), “Activity, selectivity, and sulfur resistance of Pt/WOx-ZrO2 and Pt/Beta catalysts for the simultaneous hydroisomerization of n-heptane and hydrogenation of benzene,” J. Catal., vol. 190, no. 2, pp. 309–319. [41] P. Munnik, P. E. De Jongh, and K. P. De Jong (2015), “Recent Developments in the Synthesis of Supported Catalysts,” Chem. Rev., vol. 115, no. 14, pp. 6687– 6718. [42] E. Blomsma, J. A. Martens, and P. A. Jacobs (1996), “Mechanisms of heptane isomerization on bifunctional Pd/H-beta zeolites,” J. Catal., vol. 159, no. 2, pp. 323–331. [43] E. Blomsma, J. A. Martens, and P. A. Jacobs (1997), “Isomerization and hydrocracking of heptane over bimetallic bifunctional PtPd/H-beta and PtPd/USY zeolite catalysts,” J. Catal., vol. 165, no. 2, pp. 241–248. [44] O. B. Yang and S. I. Woo (1993), “Characterization and Catalytic Properties of Pt-Ir Small Bimetallic Cluster in NaY,” Stud. Surf. Sci. Catal., vol. 75, no. C, pp. 102 671–680. [45] F. Bauer, K. Ficht, M. Bertmer, W. D. Einicke, T. Kuchling, and R. Gläser (2014), “Hydroisomerization of long-chain paraffins over nano-sized bimetallic Pt-Pd/H-beta catalysts,” Catal. Sci. Technol., vol. 4, no. 11, pp. 4045–4054. [46] I. Eswaramoorthi and N. Lingappan (2003), “Hydroisomerisation of n-hexane over bimetallic bifunctional silicoaluminophosphate based molecular sieves,” Appl. Catal. A Gen., vol. 245, no. 1, pp. 119–135. [47] I. Eswaramoorthi and N. Lingappan (2004), “Ni-Pt loaded silicoaluminophosphate molecular sieves for hydroisomerisation of n-heptane,” J. Mol. Catal. A Chem., vol. 218, no. 2, pp. 229–239. [48] A. G. Bhavani, N. Lingappa, I. Eswaramoorthi (2003), “Activity, Selectivity and Stability of Ni-Pt Loaded Zeolite-β and Mordenite Catalysts for Hydroisomerisation of nHeptane,” Appl. Catal. A Gen., vol. 253, pp. 469–486. [49] A. Corma, A. Martinez, S. Pergher, S. Peratello, C. Perego (1997), “Hydrocracking-hydroisomerization of n-decane on amorphous silica-alumina with uniform pore diameter,” Appl. Catal. A, vol. 152, pp. 107–125. [50] V. Calemma, S. Peratello, C. Perego (2000), “Hydroisomerization and hydrocracking of long chain n-alkanes on Pt/amorphous SiO2-Al2O3 catalyst,” Appl. Catal. A Gen., vol. 190, no. 1–2, pp. 207–218. [51] M. Y. Wen, I. Wender, J. W. Tierney (1990), “Hydroisomerization and Hydrocracking of n-Heptane and n-Hexadecane on Solid Superacids,” Energy and Fuels, vol. 4, no. 4, pp. 372–379. [52] S. Zhang, Y. Zhang, J. W. Tierney, and I. Wender (2000), “Hydroisomerization of normal hexadecane with platinum-promoted tungstate-modified zirconia catalysts,” Appl. Catal. A Gen., vol. 193, no. 1–2, pp. 155–171. [53] M. C. Claude, G. Vanbutsele, J. A. Martens (2001), “Dimethyl branching of long n-alkanes in the range from decane to tetracosane on pt/H-ZSM-22 bifunctional catalyst,” J. Catal., vol. 203, no. 1, pp. 213–231. [54] G. Wang, Q. Liu, W. Su, X. Li, Z. Jiang, X. Fang, C. Han, C. Li (2008), 103 “Hydroisomerization activity and selectivity of n-dodecane over modified Pt/ZSM-22 catalysts,” Appl. Catal. A Gen., vol. 335, no. 1, pp. 20–27. [55] M. Zhang, C. Li, Y. Chen, C. W. Tsang, Q. Zhang, C. Liang (2016), “Hydroisomerization of hexadecane over platinum supported on EU-1/ZSM-48 intergrowth zeolite catalysts,” Catal. Sci. Technol., vol. 6, no. 22, pp. 8016– 8023. [56] C. L. Z Yang, Y Liu, J Zhao, J Gou, K Sun (2017), “Zinc-modified Pt/SAPO-11 for improving the isomerization selectivity to dibranched alkanes,” Chinese J. Catal., vol. 38, pp. 509–517. [57] A. K. Sinha, S. Sivasanker, P. Ratnasamy ((1998), “Hydroisomerization of n- alkanes over Pt-SAPO-11 and Pt-SAPO-31 synthesized from aqueous and nonaqueous media,” Ind. Eng. Chem. Res., vol. 37, no. 6, pp. 2208–2214. [58] M. Y. Kim, K. Lee, M. Choi (2014), “Cooperative effects of secondary mesoporosity and acid site location in Pt/SAPO-11 on n-dodecane hydroisomerization selectivity,” J. Catal., vol. 319, pp. 232–238. [59] R. S. Araújo, D. C. S. Azevedo, E. Rodríguez-Castellón, A. Jiménez-López, C. L. Cavalcante (2008), “Al and Ti-containing mesoporous molecular sieves: Synthesis, characterization and redox activity in the anthracene oxidation,” J. Mol. Catal. A Chem., vol. 281, no. 1–2, pp. 154–163. [60] Y. Zhang, D. Liu, B. Lou, R. Yu, Z. Men, M. Li, Z. Li (2018), “Hydroisomerization of n-decane over micro/mesoporous Pt-containing bifunctional catalysts: Effects of the MCM-41 incorporation with Y zeolite,” Fuel, vol. 226, no. November 2017, pp. 204–212. [61] P. Liu, J. Wang, R. Wei (2008), “A Highly Efficient H b Zeolite Supported Pt Catalyst Promoted by Chromium for the Hydroisomerization of n -Heptane,” Catal. Letters, vol. 126, pp. 346–352. [62] P. Liu, J. Wang, X. Zhang, R. Wei, X. Ren (2009), “Catalytic performances of dealuminated Hβ zeolite supported Pt catalysts doped with Cr in hydroisomerization of n-heptane,” Chem. Eng. J., vol. 148, no. 1, pp. 184–190. 104 [63] V. M. Akhmedov and & S. H. Al‐Khowaiter (2007), “Recent Advances and Future Aspects in the Selective Isomerization of High n‐Alkanes,” Catal. Rev., vol. 49, pp. 33–139. [64] K. C. Mouli, O. Choudhary, K. Soni, A. K. Dalai (2012), “Improvement of cetane number of LGO by ring opening of naphthenes on Pt / Al-SBA-15 catalysts,” Catal. Today, vol. 198, no. 1, pp. 69–76. [65] Z. YuaShiyou Xing, Pengmei Lv, Junying Fu, Jiayan Wang, Pei Fan, Lingmei Yang, Zhenhong Yuann (2017), “Direct synthesis and characterization of pore- broadened Al-SBA-15,” Microporous Mesoporous Mater., vol. 239, pp. 316– 327. [66] Ngô Thị Thuận, Phạm Xuân Núi, Nguyễn Hữu Phú (2005), “Nghiên cứu đặc trưng của xúc tác MoO3/ZrO2-SO4 trong phản ứng isome hóa n-heptan,” in Tuyển tập các công trình hội nghị khoa học và công nghệ hóa hữu cơ toàn quốc lần thứ III, 2005, pp. 514–518. [67] Nguyễn Hữu Trịnh (2007), “Nghiên cứu phản ứng isome hóa n-hexan trên xúc tác Pt/gamma Al2O3,” Tạp chí hóa học, vol. 45, no. 4, pp. 403–406. [68] T. K. T. Dao and C. L. Luu (2015), “n-Hexane hydro-isomerization over promoted Pd/HZSM-5 catalysts,” Adv. Nat. Sci. Nanosci. Nanotechnol., vol. 6, no. 3, pp. 035014–035020. [69] S. C. Korre, M. T. Klein, R. J. Quann (1997), “Hydrocracking of polynuclear aromatic hydrocarbons. Development of rate laws through inhibition studies,” Ind. Eng. Chem. Res., vol. 36, no. 6, pp. 2041–2050. [70] M. F. Williams, B. Fonfé, C. Woltz, A. Jentys, J. A. R. Van Veen, and J. A. Lercher (2007), “Hydrogenation of tetralin on silica – alumina-supported Pt catalysts II . Influence of the support on catalytic activity,” J. Catal., vol. 251, pp. 497–506. [71] K. Sato, Y. Iwata, Y. Miki, H. Shimada (1999), “Hydrocracking of Tetralin over NiW / USY Zeolite Catalysts : For the Improvement of Heavy-Oil Upgrading Catalysts,” J. Catal., vol. 186, pp. 45–56. 105 [72] Z. Cao, X. Xu, Y. Qi, S. Lu, B. Qi (2010), “Petroleum Science and Technology Hydrocracking of Tetralin over Mo – Ni / Usy Dual Functional Catalysts,” Pet. Sci. Technol., no. October 2013, pp. 37–41. [73] S. G. A. Ferraz, F. M. Z. Zotin, L. R. Raddi Araujo, J. L. Zotin (2010), “Applied Catalysis A : General Influence of support acidity of NiMoS catalysts in the activity for hydrogenation and hydrocracking of tetralin,” Applied Catal. A, Gen., vol. 384, no. 1–2, pp. 51–57. [74] M. C. Carrio, B. R. Manzano, F. A. Jalo (2005), “Influence of the metallic precursor in the hydrogenation of tetralin over Pd – Pt supported zirconium doped mesoporous silica,” Green Chem., vol. 7, pp. 793–799. [75] M. A. Arribas and A. Martínez (2002), “The influence of zeolite acidity for the coupled hydrogenation and ring opening of 1-methylnaphthalene on Pt/USY catalysts,” Appl. Catal. A Gen., vol. 230, no. 1–2, pp. 203–217. [76] K. C. Park, D. J. Yim, and S. K. Ihm (2002), “Characteristics of Al-MCM-41 supported Pt catalysts: Effect of Al distribution in Al-MCM-41 on its catalytic activity in naphthalene hydrogenation,” Catal. Today, vol. 74, no. 3–4, pp. 281– 290. [77] S. G. A. Ferraz, B. M. Santos, F. M. Z. Zotin, L. R. R. Araujo, and J. L. Zotin (2015), “Influence of Support Acidity of NiMo Sul fi de Catalysts for Hydrogenation and Hydrocracking of Tetralin and Its Reaction Intermediates,” Ind. Eng. Chem. Res., vol. 54, pp. 2646–2656. [78] J. Lee, Y. Choi, J. Shin, and J. K. Lee (2015), “Selective hydrocracking of tetralin for light aromatic hydrocarbons,” Catal. Today, vol. 265, pp. 1–10. [79] R. C. Santana, P. T. Do, M. Santikunaporn, W. A. Alvarez, J. D. Taylor, E. L. Sughrue, D. E. Resasco (2006),, “Evaluation of different reaction strategies for the improvement of cetane number in diesel fuels,” Fuel, vol. 85, no. 5–6, pp. 643–656. [80] M. Chareonpanich, Z. G. Zhang, and A. Tomita (1996), “Hydrocracking of aromatic hydrocarbons over USY-zeolite,” Energy and Fuels, vol. 10, no. 4, pp. 106 927–931. [81] X. M. Yue, X. Y. Wei, B. Sun, Y. H. Wang, Z. M. Zong, X. Fan, Z. W. Liu (2012)., “A new solid acid for specifically cleaving the C arC alk bond in di(1- naphthyl)methane,” Appl. Catal. A Gen., vol. 425–426, pp. 79–84. [82] H. Matsuhashi, S. Nishiyama, H. Miura, K. Eguchi, K. Hasegawa, Y. Iizuka, A. Igarashi, N. Katada, J. Kobayashi, T. Kubota, T. Mori, K. Nakai, N. Okazaki, M. Sugioka, T. Umeki, Y. Yazawa, D. Lu (2004), “Effect of preparation conditions on platinum metal dispersion and turnover frequency of several reactions over platinum-supported on alumina catalysts,” Appl. Catal. A Gen., vol. 272, no. 1– 2, pp. 329–338. [83] H. Fan, B. Han, T. Jiang, J. Guo, Q. Wang, Y. Cheng, S. Wu (2011), “Hydrocracking of anthracene to ethyl biphenyl promoted by coupling supercritical water and cracking catalysts,” ChemCatChem, vol. 3, no. 9, pp. 1474–1479. [84] H. Fan, Q. Wang, J. Guo, T. Jiang, Z. Zhang, G. Yang, B. Han (2012), “Elimination of the negative effect of nitrogen compounds by CO2-water in the hydrocracking of anthracene,” Green Chem., vol. 14, no. 7, pp. 1854–1858. [85] V. Calemma, R. Giardino, and M. Ferrari (2010), “Upgrading of LCO by partial hydrogenation of aromatics and ring opening of naphthenes over bi-functional catalysts,” Fuel Process. Technol., vol. 91, no. 7, pp. 770–776. [86] R. Galiasso Tailleur and J. R. Nascar (2008), “The effect of aromatics on paraffin mild hydrocracking reactions (WNiPd/CeY-Al2O3),” Fuel Process. Technol., vol. 89, no. 8, pp. 808–818. [87] A. Haas, S. Rabl, M. Ferrari, V. Calemma, and J. Weitkamp (2012), “Ring opening of decalin via hydrogenolysis on Ir/- and Pt/silica catalysts,” Appl. Catal. A Gen., vol. 425–426, pp. 97–109. [88] C. Guan, Z. Wang, S. Yu, A. Guo, and G. Que (2004), “Upgrading petroleum residue by two-stage hydrocracking,” Fuel Process. Technol., vol. 85, no. 2–3, pp. 165–172. 107 [89] P. A. Rautanen, J. R. Aittamaa, and A. O. I. Krause (2001), “Liquid phase hydrogenation of tetralin on Ni/Al2Ỏ3,” Chem. Eng. Sci., vol. 56, pp. 1247–1254. [90] O. A. Verónica A.Valles, Brenda C.Ledesma, Lorena P. Rivoira, Jorgelina Cussa, A. R. Anunziata, and Beltramone (2016), “Experimental design optimization of the tetralin hydrogenation over Ir–Pt-SBA-15,” Catal. Today, vol. 271, pp. 140–148. [91] K. C. Mouli, O. Choudhary, K. Soni, and A. K. Dalai (2012), “Improvement of cetane number of LGO by ring opening of naphthenes on Pt/Al-SBA-15 catalysts,” Catal. Today, vol. 198, no. 1, pp. 69–76. [92] O. J. D. Souza, R. J. Mascarenhas, T. Thomas, B. M. Basaveraja, A. K. Saxena, K. Mukhopadhyay, D. Roy (2015), “Platinum decorated multi-walled carbon nanotubes / Triton X-100 modified carbon paste electrode for the sensitive amperometric determination of Paracetamol,” J. Electroanal. Chem., vol. 739, pp. 49–57. [93] X. Liu, W. Na, H. Liu, and X. Su (2017), “Fluorescence turn-off-on probe based on polypyrrole/graphene quantum composites for selective and sensitive detection of paracetamol and ascorbic acid,” Biosens. Bioelectron., vol. 98, pp. 222–226. [94] M. E. Bosch, A. J. S. Ruiz, and C. B. Ojeda (2006), “Determination of paracetamol : Historical evolution,” Jounal Pharm. Biomed. Anal., vol. 42, pp. 291–321. [95] C. M. A. Brett, A. N. A. Maria, and O. Brett (1994), "Electrochemistry: Principles , Methods , and Applications", Oxford University Press, New York, USA [96] A. J. Bard, L. R. Faulkner, E. Swain, and C. Robey (2001), "Electrochemical methods: Fundamentals and Applications", John Wiley & Son, INC. [97] V. Mirceski, R. Gulaboski, M. Lovric, I. Bogeski, and R. Kappl (2013), “Square-Wave Voltammetry : A Review on the Recent Progress,” vol. 25, pp. 1– 11. 108 [98] E. Bayram and E. Akyilmaz (2016), “Sensors and Actuators B : Chemical Development of a new microbial biosensor based on conductive polymer / multiwalled carbon nanotube and its application to paracetamol determination,” Sensors Actuators B. Chem., vol. 233, pp. 409–418. [99] A. C. . Durst, R. A, Baumner. A.J, Murray. R.W, Buck. R.P (2007), “Chemically modified electrodes: Recommended terminology and definitions (IUPAC Recommendations 1997),” Pure Appl. Chem., vol. 69, no. 6, pp. 1317–1324. [100] K. E. Labuda J., Vanícková M., Bučková M (2000), “Development in Voltammetric Analysis with Chemically Modified Electrodes and Biosensors,” Chem. Pap., vol. 54, pp. 95–103. [101] I. Noviandri and R. Rakhmana (2012), “Carbon Paste Electrode Modified with Carbon Nanotubes and Poly ( 3-Aminophenol ) for Voltammetric Determination of Paracetamol” , Int. J. Electrochem, Sci. vol. 7, pp. 4479–4487. [102] J. Luo, J. Sun, J. Huang, and X. Liu (2016), “Preparation of water-compatible molecular imprinted conductive polyaniline nanoparticles using polymeric micelle as nanoreactor for enhanced paracetamol detection,” Chem. Eng. J., vol. 283, pp. 1118–1126. [103] Y. Teng, L. Fan, Y. Dai, M. Zhong, X. Lu, and X. Kan (2015), “Biosensors and Bioelectronics Electrochemical sensor for paracetamol recognition and detection based on catalytic and imprinted composite film,” Biosens. Bioelectron., vol. 71, pp. 137–142. [104] P. K. Kalambate and A. K. Srivastava (2016), “Sensors and Actuators B : Chemical Simultaneous voltammetric determination of paracetamol , cetirizine and phenylephrine using a multiwalled carbon nanotube-platinum nanoparticles nanocomposite modified carbon paste electrode,” Sensors Actuators B. Chem., vol. 233, pp. 237–248. [105] R. Olivé-monllau, F. X. Mu, and E. Baldrich (2013), “Sensors and Actuators B : Chemical Characterization and optimization of carbon nanotube electrodes produced by magnetic entrapment : Application to paracetamol detection,” 109 Sensors Actuators B vol. 185, pp. 685–693. [106] P. A. Raymundo-pereira, A. M. Campos, C. D. Mendonc, M. L. Calegaro, S. A. S. Machado, and O. N. O. Jr (2017), “Sensors and Actuators B : Chemical Printex 6L Carbon Nanoballs used in Electrochemical Sensors for Simultaneous Detection of Emerging Pollutants Hydroquinone and Paracetamol,” vol. 252, pp. 165–174. [107] A. Kutluay and M. Aslanoglu (2013), “Chemical Modification of electrodes using conductive porous layers to confer selectivity for the voltammetric detection of paracetamol in the presence of ascorbic acid , dopamine and uric acid,” Sensors Actuators B. Chem., vol. 185, pp. 398–404. [108] I. Sadok and K. Tyszczuk-rotko (2016), “Chemical Bismuth particles Nafion covered boron-doped diamond electrode for simultaneous and individual voltammetric assays of paracetamol and caffeine,” Sensors Actuators B , vol. 235, pp. 263–272, 2016. [109] P. K. Kalambate, B. J. Sanghavi, S. P. Karna, and A. K. Srivastava (2015), “Sensors and Actuators B : Chemical Simultaneous voltammetric determination of paracetamol and domperidone based on a graphene / platinum nanoparticles / nafion composite modified glassy carbon electrode,” Sensors Actuators B. Chem., vol. 213, pp. 285–294. [110] X. Kang, J. Wang, H. Wu, J. Liu, I. A. Aksay, and Y. Lin (2010), “A graphene- based electrochemical sensor for sensitive detection of paracetamol,” Talanta, vol. 81, no. 3, pp. 754–759 [111] S. B. Tanuja, B. E. K. Swamy, and K. V. Pai (2017), “Electrochemical determination of paracetamol in presence of folic acid at nevirapine modi fi ed carbon paste electrode : A cyclic voltammetric study,” J. Electroanal. Chem., vol. 798, no. May, pp. 17–23. [112] M. Zidan, T. A. N. W. E. E. Tee, and A. H. Abdullah (2011), “Electrochemical Oxidation of Paracetamol Mediated by MgB 2 Microparticles Modified Glassy Carbon Electrode,” E-Jounal of Chemistry, vol. 8, no. 2, pp. 553–560. 110 [113] N. T. A. Thu, H. Van Duc, N. Hai Phong, N. D. Cuong, N. T. V. Hoan, and D. Quang Khieu (2018), “Electrochemical Determination of Paracetamol Using Fe3O4/Reduced Graphene-Oxide-Based Electrode,” J. Nanomater., vol. 2018, pp. 1–15. [114] F. Chang, G. Wang, Y. Xie, M. Zhang, and J. Zhang (2013), “Synthesis of TiO 2 nanoparticles on mesoporous aluminosilicate Al-SBA-15 in supercritical CO 2 for photocatalytic decolorization of methylene blue,” Ceram. Int., vol. 39, no. 4, pp. 3823–3829. [115] A. Sacara, F. Pitzalis, A. Salis, G. L. Turdean, and L. M. Muresan (2019), “Glassy Carbon Electrodes Modi fi ed with Ordered Mesoporous Silica for the Electrochemical Detection of Cadmium Ions,” ACS Omega, vol. 4, pp. 1410– 1415. [116] N. Lashgari, A. Badiei, and G. M. Ziarani (2017), “A novel functionalized nanoporous SBA-15 as a selective fluorescent sensor for the detection of multianalytes (Fe3+ and Cr2O72-) in water,” J. Phys. Chem. Solids, vol. 103, pp. 238–248. [117] D. Lin, Y. Jiang, Y. Wang, and S. Sun (2008), “Silver Nanoparticles Confined in SBA-15 Mesoporous Silica and the Application as a Sensor for Detecting Hydrogen Peroxide,” J. Nanomater., vol. 2008, 1–10. [118] M. Yadavi, A. Badiei, and G. Mohammadi (2013), “Applied Surface Science A novel Fe 3 + ions chemosensor by covalent coupling fluorene onto the mono , di- and tri-ammonium functionalized nanoporous silica type,” Appl. Surf. Sci., vol. 279, pp. 121–128. [119] S.-G. S. and X.-C. S. Rui-Xiang Wang, Jing-Jing Fan, You-Jun Fan, Jing-Ping Zhong, Li Wang (2014), “Platinum nanoparticles on porphyrin functionalized graphene nanosheets as superior catalyst for methanol electrooxidation,” R. Soc. Chem., vol. 6, no. 24, pp. 14999–15007. [120] Lê Viết Hải, Trần Đại Lâm (chủ biên), Nguyễn Tuấn Dung, Nguyễn Lê Huy (2017), Các phương pháp phân tích hóa lý vật liệu. NXB Khoa học tự nhiên và 111 công nghệ. [121] ThermoScientific (2013), “Introduction to Fourier Transform Infrared Spectroscopy.” Thermo Fisher Scientific. [122] J. Lynch (2003), "Physico-chemical analysis of industrial catalysts". Institut Francai du Pe1trole Publication. [123] W. Yu, Y. Tang, L. Mo, P. Chen, H. Lou, and X. Zheng (2011), “Bifunctional Pd / Al-SBA-15 catalyzed one-step hydrogenation – esteri fi cation of furfural and acetic acid : A model reaction for catalytic upgrading of bio-oil SBA-15,” CATCOM, vol. 13, no. 1, pp. 35–39. [124] D. Zhao, Y. Wan, W. Zhou (2013), "Ordered mesoporous materials", Wiley - VCH Verlag GmbHz & CoKGaA. [125] G. M. Kumaran, S. Garg, K. Soni, M. Kumar, and L. D. Sharma (2007), “Effect of Al-SBA-15 Support on Catalytic Functionalities of Hydrotreating Catalysts . II . Effect of Variation of Molybdenum and Promoter Contents on Catalytic Functionalities,” Industrial & Engineering Chemistry Research, pp. 4747–4754. [126] J. Berlin (2011), “Analysis of Boron with Energy Dispersive X-ray Spectrometry: Advances in light element analysis with SDD technology,” Imaging Microsc., vol. 13, pp. 19–21. [127] G. M. Kumaran, S. Garg, K. Soni, M. Kumar, and J. K. Gupta (2008), “Synthesis and characterization of acidic properties of Al-SBA-15 materials with varying Si / Al ratios,” vol. 114, pp. 103–109, 2008. [128] J. R. Regalbuto, A. Navada, S. Shadid, M. L. Bricker, and Q. Chen (1999), “An Experimental Verification of the Physical Nature of Pt Adsorption onto Alumina,” J. Catal., vol. 348, pp. 335–348. [129] T. Sugii, R. Ohnishi, J. Zhang, A. Miyaji, and Y. Kamiya (2006), “Acidity- attenuated heteropolyacid catalysts : Acidity measurement using benzonitrile- TPD and catalytic performance in the skeletal isomerization of n -heptane,” J. vol. 116, pp. 179–183, 2006. [130] L. Gao, Z. Shi, U. Etim, W. Xing, P. Wu, D. Han, S. Mintova, P. Bai, Z. Yan 112 (2019), “Beta-MCM-41 micro-mesoporous catalysts in the hydroisomerization of n-heptane: Definition of an indexed isomerization factor as a performance descriptor,” Microporous Mesoporous Mater., vol. 277, pp. 17–28. [131] L. Valverde, P. Sa, A. De Lucas, and F. Dorado (2005), “Hydroisomerization of n -octane over platinum catalysts with or without binder,” Applied Catalysis A, vol. 282, pp. 15–24. [132] W. Zhang and P. G. Smirniotis (1999), “Effect of Zeolite Structure and Acidity on the Product Selectivity and Reaction Mechanism for n-Octane Hydroisomerization and Hydrocracking,” Jounal of Catalysis, vol. 416, pp. 400– 416. [133] M. Guisnet and P. Magnoux (2001), “Organic chemistry of coke formation,” Appl. Catal. A Gen., vol. 212, no. 1–2, pp. 83–96. [134] Veronica A. Valles, Brenda C. Ledesma, Lorena P. Rivoira, Jorgelina Cussa, Oscar A. Anunziata, Andrea R. Beltramone (2015), “Experimental design optimization of the tetralin hydrogenation over Ir-Pt-SBA-15; Catalysis Today, vol 271, pp 140-148. [135] D. E. Siriporn Jongpatiwut, Zhongrui Li, G. W. Resasco, Walter E. Alvarez, Ed L. Sughrue, and Dodwell (2004), “Competitive hydrogenation of poly-aromatic hydrocarbons on sulfur-resistant bimetallic Pt-Pd catalysts,” Appl. Catal. A, vol. 262, pp. 241–253. [136] J. Chan and C. Tan (2006), “Hydrogenation of Tetralin over Pt / γ -Al 2 O 3 in Trickle-Bed Reactor in the Presence of Compressed CO2,” Enegy & Fuels, vol. 20, no. 15, pp. 771–777. [137] M. M. Rusu, C. I. Fort, L. C. Cote, A. Vulpoi, M. Todea, G. L. Turdean, V. Danciu, I. C. Popescu, L. Baia (2018), “Insights into the morphological and structural particularities of highly sensitive porous bismuth-carbon nanocomposites based electrochemical sensors,” Sensors Actuators, B Chem., vol. 268, pp. 398–410. [138] F. J. Burpo, E. A. Nagelli, L. A. Morris, and J. P. Mcclure (2017), “Direct 113 solution-based reduction synthesis of Au , Pd , and Pt aerogels,” Jounal Mater. Res., vol. 22, pp. 4153–4165. [139] W. Y. Su and S. H. Cheng (2010), “Electrochemical oxidation and sensitive determination of acetaminophen in pharmaceuticals at poly(3,4-ethylene- dioxythiophene)-modified screen-printed electrodes,” Electroanalysis, vol. 22, no. 6, pp. 707–714. [140] J. Song, J. Yang, J. Zeng, J. Tan, and L. Zhang (2011), “Graphite oxide film- modified electrode as an electrochemical sensor for acetaminophen,” Sensors Actuators, B Chem., vol. 155, no. 1, pp. 220–225. 114 APPENDIX