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1 Methylation of Coal Tar Naphthalene Oil Fractions to Increase Amount of Dimethylnaphthalenes using Au-Beta Zeolite Catalysts Fatih Güleç, Aysun Özen, Ali Karaduman Ankara University, Engineering Faculty, Chemical Engineering,06100, Ankara, TURKIYE 1
2 CONTENTS OF PRESENTATION Aim Introduction of PEN Polyethylene Naphthalate (PEN) Comparison of PEN and PET Production Method of PEN Literature Survey Experimental Studies Preparation of Catalysts Catalytic Reaction Results and Discussions Conclusion 2
3 AIM The aim of the study to increase amount of DMN with using methylation of Coal Tar Naphthalene Oil Frction (CTNOF) over Beta and Au impregnated Beta zeolite catalysts. 3
4 POLYETHYLENE NAPHTHALATE (PEN) PEN is an alternative polymer to the Polyethylene terephthalate (PET) because of its better features such as oligomer extraction, tensile strength, young s modulus, radiation resistance, UV absorbance and glass transition temperature. Because of the difficulties in production of DMN especially 2,6-DMN, PEN cannot be widespread in large industrial applications. One of the most difficulties in production of 2,6-DMN is that high selective catalysts has not been developed yet. Because of this reason, the studies about PEN focus on the synthesis of shape selective catalysts and produce high selective DMN products. Today PEN is just used very narrow area such as flexible printed circuit boards, bottles, solar cells, food-contact applications, etc. 4
5 Comparison PEN & PET Figure Properties of PET and PEN ( 5
6 Naphthalene Source (2-Methyl Naphthalene, Naphthalene or CTNOF) Methylation Alkylation Disproportionation Production of PEN 2,6-Dimethylnaphthalene (2,6-DMN) Oxidation Air 2,6 Naphthalene Dicarboxylic acid (NDA) Esterification CH 3 OH Dimethyl 2,6-Naphthalene Dicarboxylate (NDC) Polymerisation HOCH 2 CH 2 OH Polyethylene Naphthalate (PEN) 6
7 LITERATURE SURVEY Experiment Conditions Experimental Results Reactor Temp ( C) Feed of reactor Catalysts Conversion Distribution of Selectivity of *,* -DMN of Naph. or Amount Type Naph. MN DMN 2,6-2,7-2,3-1,6-1,3-1,8-1,7-2-MN Niftaliyeva et al. (2015) Zhang et. al. (2010) Liang et al. (2010) Fixed Bed Fixed Bed Fixed Bed MN TMB Methanol MN 1,3,5-TMB Methanol MN 1,3,5-TMB Methanol MN 1,2,4-TMB Methanol 1g Y Zeo 67.8 Cu/Y Zeo La/Y Zeo g HZSM HT-HZSM SiO2HZSM g HZSM Pt/ZSM Park et Fixed MN 0.3g HM Bed al.(2005) HM HM550A HM800A Millini et al. (2003) Fixed Bed 350 (40 atm) Naph. 1,2,4-TMB Methanol? MFI EUO MOR MAZ BETA FAU
8 EXPERIMENTAL STUDIES Catalytic Reaction N2 2 ± GC-MS 1. Nitrogen tube; 2. High-pressure liquid pump; 3. Valve; 4. Flowmeter; 5. PID temperature controller; 6. Fixed-bed flow reactor; 7. Condenser; 8. Phase-separator, 9.GC-MS Figure Catalytic Reaction System Table Condition of experiments Weight Hourly Space Velocity (h -1 ) 2 Time on stream (h) () 2-8 Temperature ( C) 400 Reactor Type Fixed Bed Reactor Amount of Catalyst t 1g (2 cm 3 ) Catalysts Type HB5, AuB5, AuB7 CTNOF was supplied from Kardemir Iron Steel Industry Trade & Company Inc. TURKEY. Feed (w:w:w) CTNOF(1) : m-xylene (3) : Methanol (5) 8 9
9 Preparation of Catalysts Calcination Metal (Au) Salt Solution Au(NO 3 ) 2 Au NH 4 Form Support Material (Commercial Beta Zeolite) Proton Form Beta Zeolite Filtration Wet Impregnation Drying H 2 O HB5 Calcination NO 2 25 C Calcination Steps 350 C 3 h 0.5 h 05h C 4 h 750 C 4 h HB5: H form Beta C AuB5: Au (01%, w) doped Beta C AuB7: Au (0.1%, w) doped Beta C AuB7 AuB5 25 C 0.5 h 350 C 3h 0.5 h Figure Catalysts preparation steps 9
10 RESULTS AND DISCUSSIONS Characterization of Catalysts Nitrogen adsorption and desorption isotherms of HB5, AuB5 and AuB7 were measured by using a Quantachrome NOVA 2200 instrument and the results are giving in Figure. (cc/g) Volume ( AuB7 Adsorption Desorption AuB5 Adsorption Desorption HB5 Adsorption Desorption 0,0 0,2 0,4 0,6 0,8 1,0 1,2 P/P 0 Figure Nitrogen sorption isotherms 10
11 Specific surface areas and pore volumes were calculated using BET model and BJH method, respectively. The results are given in Table. Table BET surface area and BJH pore volume Catalysts BET Surface Area (m 2 /g) HB AuB AuB BJH Pore Volume (cc/g) Table EDX results Catalysts Si Al O Au HB AuB AuB The surface morphology of catalysts were imaged by SEM using a ZEISS EVO 40 microscope. The results are given in Figures. Using EDX method, the amount of Au and its dispersion on Beta were also seen. HB5 AuB5 AuB7 Figure SEM results of catalysts 11
12 X-ray diffraction (XRD) patterns of catalysts were recorded using Inel Equinox 1000 with Cu-Kα radiation. The results are given in Figure. HB5 AuB5 AuB7 The peaks at 2θ=7.6, 13.4, 14.4, 21.2 and 22.2 on XRD patterns are associated with Beta structure (Xie et al. 2008) Figure XRD analysis results of catalysts 12
13 The infrared analyses were carried out using a Mattson 1000 FTIR spectrometer. The pellets (0.109 g/cm 2 ) were prepared by pressing the sample powders at 10 kpa, and all samples were scanned 30 times per analysis at 16 cm 11 resolution within the cm 1 infrared region. The results are given in Figure. 3,0 465 cm 1 : bending mode of T-O-T 540 cm 1 : symmetric stretching modes of T-O-T 2,5 805 cm 1 : internal bonds of the tetrahedral SiO4 structural unit 2,0 1100cm 1 : asymmetric stretching of Si-O-Si 3446cm 1 :O-H of Beta zeolite or water absorbents 1,5 1,0 (T is Si or Al) Absorbance 0,5 0,0-0,5-1,0-1,5-2,0-2,5-3,0 AuB7 AuB5 HB5-3,5-4, Wavenumbers (cm-1) Figure FTIR analysis results of catalysts 13
14 Results of Catalytic Studies The feed and products were analysed using a Thermo-Finnegan gas chromatograph (GC) with a mass spectroscopy (MS) and azebron (ZB-1MS) column (60 m x 0.25 mm). An example of gas chromatogram results is given in the figure. RT: ,6-DMN 2,7-DMN 1,3-DMN NL: 3.53E6 Other DMNs TIC MS AUBET550 T400KS2N RT: m-xylene Relative Abundance Relative Ab bundance Time (min) Time (min) Methan nol thalene Napht 2-MN 1-MN Figure Gas chromatogram for methylation of CTNOF over HB5 zeolite and its magnified regions between 18-21, and minutes 14
15 The conversion of Naphthalene and the selectivity of Naphthalene, MN and DMN in product stream were given in figures Con nversion of Naphthale ene HB5 AuB5 AuB7 S N HB5 AuB5 AuB TOS, h Figure Conversion of Naphthalene TOS, h Figure Selectivity of Naphthalene HB5 40 AuB5 AuB7 35 S DMN 10 8 S MN HB5 AuB5 AuB TOS, h Figure Selectivity of DMN TOS, h Figure Selectivity of MN 15
16 The selectivity of β,β-dmns (2,6-DMN, 2,7-DMN and 2,3-DMN) were given in figures DMN 20 HB5 26-DMN AuB5 2,6 DMN 2,7-DMN 2,3-DMN 2,6 DMN 2,7-DMN 2,3-DMN Selectivity 12 8 Selectivity h 4h 8h 0 2h 4h 8h 20 2,6-DMN 2,7-DMN 2,3-DMN 16 AuB7 * S M M * DMN *100 Se electivity h 4h 8h S* indicates selectivity of 2,6-DMN or 2,7- DMN or 2,3-DMN and M* indicates the amount of 2,6-DMN or 2,7-DMN or 2,3-DMN in product stream. M DMN indicates the amount of DMN in product stream. Figure Selectivity of β,β-dmns with TOS on HB5, AuB5, AuB7 16
17 The selectivity of α,β-dmns (1,6-DMN, 1,3-DMN, 1,8-DMN and 1,2-DMN) were given in figures ,6-DMN 1,3-DMN 1,8-DMN 1,2-DMN HB5 30 1,6-DMN 1,3-DMN 1,8-DMN 1,2-DMN AuB5 Selectivity 20 Selectivity h 4h 8h 0 2h 4h 8h ,6-DMN AuB7 * 1,3-DMN * M 1,8-DMN S *100 1,2-DMN M DMN Se electivity h 4h 8h Figure Selectivity of α,β-dmns with TOS on HB5, AuB5, AuB7 S* indicates selectivity of 1,6-DMN,, 1,3-DMN,, 1,8-DMN or 1,2-DMN and M* indicates the amount of 1,6-DMN, 1,3-DMN, 1,8-DMN or 1,2- DMN in product stream. M DMN indicates the amount of DMN in product stream. 17
18 CONCLUSION In this study, to increase amount of DMN, methylation of Coal Tar Naphthalene Oil Fractions (CTNOF) over Beta and Au doped Beta zeolite catalysts was studied. The nitrogen sorption analysis showed that the isotherms of all catalysts are corresponding to type IV which is typical of mesoporous materials according IUPAC classification. The SEM images illustrated that the catalysts showed almost uniform crystals with similar morphology. EDX results showed that the amount of Au was impregnated on Beta and the dispersions of them are quite homogeneous. The XRD patterns of catalysts gave information about that the main structure of Beta weren t changed after doping Au and chancing calcination temperature. FTIR results supported to the XRD and nitrogen sorption results about Structure of Au impregnated Beta and unimpregnated Beta. The conversion of Naphthalene increase with TOS for all catalysts. The highest conversion was seen on HB5 catalysts around 30% (It is 26% for AuB7 and 23% for AuB5). The selectivity of Naphthalene over all catalysts show an upward trend with TOS from 48% to 60%. 18
19 While the highest selectivity of MN was seen nearly 40% over HB5, thehighest selectivity of DMN was calculated around 15% over AuB7. Whereas HB5 is selective for 2,6-DMN, 2,7-DMN and 1,3-DMN, Au doped Beta catalysts selective for 2,3-DMN,, 1,6-DMN 1,8-DMN and 1,2-DMN. AuB7 showed superior selectivity of 2,3-DMN and 1,2-DMN (the highest selectivity of 2,3-DMN and 1,2-DMN are 17%, 35%, respectively). Doping Au on Beta climbed the selectivity of 1,2-DMN and 1,8-DMN. Furthermore, increasing calcination temperature of Au doped Beta much increased the selectivity of 1,8-DMN in short TOS. Experiment Conditions Experimental Results Reactor Temp ( C) Feed of reactor Catalysts Conversion Distribution of Selectivity of *,* -DMN of Naph. or Amount Type Naph. MN DMN 2,6-2,7-2,3-1,6-1,3-1,8-1,2-2-MN Fixed Bed 400 CTNOF m-xylene Methanol 1g HB AuB AuB
20 References Baerlocher, C. H., McCusker, L. B., Olson, D. H Atlas of Zeolite Framework Types. Structure Commission of the International Zeolite Association , Baran, R., Millot, Y., Onfroy, T., Krafft, C.M., Dzwigaj, S Influence of the nitric acid treatment on Al removal, framework composition and acidity of BEA zeolite investigate by XRD, FTIR and NMR. Microporous and Mesoporous Materials, 163, Jin, L., Zhou, X.,Hu, H., Ma, B Synthesis of 2,6-dimethylnaphthanele by methylation of 2-methylnaphthalene on mesoporous ZSM-5 by desilication. Catalysis Communications, 10, Liang, Z., Xinmen, G., Min, L., Xiangsheng, W. and Chunshan, S Methylation of 2-methylnaphthalene with methanol over NH 4 FandPtmodified HZSM-5 Catalysts. Chinese Journal of Chemical Engineering,18(5), Lin, L., Fang, Y. and Hu, H Selective synthesis of 2,6-dimethylnaphthalene by methylation of 2-methylnaphthalene with methanol on Zr/(Al)ZSM- 5. Catalysis Communications, 7, Millini, R., Frigerio, F., Bellussi, G., Pazzuconi, G., Perego, C., Pollesel, P. and Romano, U A priori selection of shape-selective zeolite catalysts for the synthesis of 2,6-dimethylnaphtalane. Journal of Catalysis, 217, Niftaliyeva, A., Güleç, F., Şimşek, E. H., Güllü, M.,& Karaduman, A.(2015). The Methylation Kinetics of 2-Methyl Naphthalene over Cu and La Modified Y Zeolite. Anadolu University Journal of Science And Technology a Applied Sciences and Engineering, 16(2), Park, J.N., Wang, J., Hong, S.I. and Lee, C.M., Effect of Dealumination of Zeolite Catalysts on Methylation of 2-Methylnaphthalene in a Highpressure Fixed-bed Flow Reactor. Applied Catalysis A: General, 292, Pu, S.B. and Inui, T Synthesis of 2,6-methylnaphthalene by methylation of methylnaphthalene on medium and large-pore zeolite catalysts. Applied Catalysis A: General, 146, Song, C., Shen, J., Reddy, K.M., Sun, L., Lillwitz, L Shape-selective Fe-MFI catalyst for synthesis of 2,6-dimethylnaphthalene by methylation with methanol. The 40th Anniversary of International Zeolite Conference Zhang, C., Guo, X., Song, C., Zhao, S., & Wang, X. (2010). Effects of steam and TEOS modification on HZSM-5 zeolite for 2, 6-dimethylnaphthalene synthesis by methylation of 2-methylnaphthalene with methanol. Catalysis Today, 149(1),
21 Xie, B., Song, J., Ren, L., Ji, Y., Li, J., & Xiao, F. S. (2008). Organotemplate-free and fast route for synthesizing beta zeolite. Chemistry of Materials, 20(14),
22 THANK YOU Ankara University Technology Research Group (ATEKLAB) We are thankful appreciate Ankara University Scientific Research Projects We are thankful appreciate Ankara University Scientific Research Projects Department (PN: 15B ) and The Scientific and The Technological Research Council of Turkey (TÜBİTAK, PN:112M297) for the support of this study. 22
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