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RUG01-002366982 2017 0001 AC.Pdf Pyrolysis of Cyclic Compounds: a Combined Kinetic Modeling and Experimental Study Sander D'hondt Supervisor: Prof. dr. ir. Kevin Van Geem Counsellor: Florence Vermeire Master's dissertation submitted in order to obtain the academic degree of Master of Science in Chemical Engineering Department Of Materials, Textiles And Chemical Engineering Chair: Prof. dr. Paul Kiekens Faculty of Engineering and Architecture Academic year 2016-2017 The only time success comes before work is in the dictionary. ~ Harvey Specter Acknowledgements On the very outset of this master thesis, I would like to extent my sincerest appreciation and gratitude towards all the people who stood by my side during the past year. Without their active guidance, help, cooperation and encouragement, this work would not be what it is now. First of all, I want to thank my promotor, prof. dr. ir. Kevin Van Geem, and prof. dr. ir. Guy Marin for giving me the chance to work on this very interesting and challenging subject, and for all the fascinating classes we could attend over the past years. I am also very grateful to my counsellor, ir. Florence Vermeire, without whom I never could have brought this thesis to a successful end. Thank you for all your help with the simulations, all the feedback on the poster, presentations and writings, and for learning me to have lots of patience with Genesys. A lot of gratitude goes to my office buddies, Victor and Cato, for all the laughs we had, all the misery we shared and all the Word conundrums we solved as a united front. I can of course also not forget our part-time office guests, Gio and Jeffrey, who made the late evenings that much more fun. Special thanks to the ladies of the ‘party cube’, Julie, Blerta and Annelies, for all the coffee, 10 ‘o clock, lunch, 4 ‘o clock, dinner and late night breaks! These made me forget the long hours in the last few weeks. I am of course also extremely grateful to my awesome MaChT board. I have enjoyed every activity, every meeting, every discussion, every laugh, and I hope you guys did as well! I think we achieved a lot of great things this year and can proudly look back; I know I will! Last but not least, I want to thank my parents and sister for all the support they gave me during all my years at university, and for always being there. Sander D’hondt June 2nd 2017 FACULTY OF ENGINEERING AND ARCHITECTURE Laboratory for Chemical Technology Director: Prof. Dr. Ir. Guy B. Marin Laboratory for Chemical Technology Declaration concerning the accessibility of the master thesis Undersigned, Sander D’hondt Graduated from Ghent University, academic year 2016-2017 and is author of the master thesis with title: Pyrolysis of Cyclic Compounds: a Combined Kinetic Modeling and Experimental Study The author(s) gives (give) permission to make this master dissertation available for consultation and to copy parts of this master dissertation for personal use. In the case of any other use, the copyright terms have to be respected, in particular with regard to the obligation to state expressly the source when quoting results from this master dissertation. June 2nd 2017 Sander D’hondt Laboratory for Chemical Technology • Technologiepark 914, B-9052 Gent • www.lct.ugent.be Secretariat : T +32 (0)9 33 11 756 • F +32 (0)9 33 11 759 • [email protected] Pyrolysis of Cyclic Compounds: a Combined Kinetic Modeling and Experimental Study Sander D’hondt Master's dissertation submitted in order to obtain the academic degree of Master of Science in Chemical Engineering Academic year 2016-2017 Promotor: Prof. dr. ir. Kevin M. Van Geem Counsellor: ir. Florence Vermeire GHENT UNIVERSITY Faculty of Engineering and Architecture Department Of Materials, Textiles And Chemical Engineering Chairman: Prof. dr. Paul Kiekens Abstract The thermal decomposition of mono- and polycyclic species is studied in this work by the automatic generation of a kinetic model with Genesys and validation based on experimental literature data. The chosen reference compounds are cyclohexane, methyl cyclohexane and decalin to represent the monocyclic, substituted monocyclic and polycyclic alkanes respectively. Ab initio rate coefficients for the initial decomposition reactions of methyl cyclohexane are taken from literature while the majority of the other reactions are based on rate rules. Reactions in the decalin pyrolysis mechanism are referred to similar reactions from methyl cyclohexane. The model simulated mole fractions for all compounds agree well with the experimental mole fractions for most product species, including aromatics. Reaction path analyses have been performed to get a better insight in the decomposition chemistry. Large differences exist between these components with respect to the initial decomposition pathways and formation of aromatics. Keywords: Pyrolysis, cyclohexane, methyl cyclohexane, decalin, automatic kinetic model generation, rate of production analysis. Pyrolysis of Cyclic Compounds: a Combined Kinetic Modeling and Experimental Study Sander D’hondt Promotor: prof. dr. ir. K. M. Van Geem Counselor: ir. Florence Vermeire Abstract: The thermal decomposition of mono- and polycyclic constructed manually. These reactions include ring-opening species is studied in this work by the automatic generation of a isomerizations and hydrogen abstractions, followed by C-C β- kinetic model with Genesys and validation based on experimental scissions that open the ring. Rate coefficients for these literature data. The chosen reference compounds are methyl reactions are taken from ab initio calculations on the CBS-QB3 cyclohexane and decalin to represent substituted cyclohexanes level of theory performed by Wang et al.2 The ring-opening and polycyclic species respectively. The model simulated mole isomerization reactions were computed by Zhang et al.3 with fractions for both compounds agree well with the experimental mole fractions for most product species, including aromatics. high-level quantum chemical calculations and RRKM master Reaction path analyses have been performed to get a better insight equation simulations. Next, the generation of a pyrolysis in the decomposition chemistry. Large differences exist between mechanism for the resulting C7 products is done with the use these two components with respect to the initial decomposition of Genesys. The reaction families included in Genesys are (i) pathways and formation of aromatics. intra- and intermolecular hydrogen abstraction reactions (ii) β- Keywords: Pyrolysis, cyclohexane, methyl cyclohexane, decalin, scissions and the reverse intra- and intermolecular addition automatic kinetic model generation, rate of production analysis. reactions (iii) bond scissions and the reverse recombination reactions (iv) Diels-Alder cyclization. Rate coefficients for the I. INTRODUCTION majority of the reactions have been calculated by the group 4,5 At present, polyethylene based plastics are used in additive framework developed by Sabbe et al. Rate rules used for intramolecular hydrogen abstraction and addition reactions packaging, construction, transportation and much more. Not 6 7 only the numerous applications and advantages compared to are taken from Van de Vijver et al. and Wang et al. respectively. AramcoMech2.08 is used as a base mechanism alternatives like glass, but also the world’s rising prosperity, 9 spur the demand for plastics and other chemicals. Moreover, and the model of Sharma et al. is used for pathways towards with government policies and incentives promoting the use of aromatic species. non-fossil bases resources, the need for alternatives arises. The decalin kinetic model is fully constructed with Genesys, One alternative can be found in the use of cellulose, present using the same reaction families, extended with ring-opening in lignocellulosic biomass. Through catalytic hydro- isomerizations, and the same rate rules as in the mechanism for deoxygenation (HDO) cellulose is converted into a bio-oil methyl cyclohexane. Arrhenius parameters for the ring-opening containing straight-chain alkanes (mainly n-hexane). The so- isomerization and for initial hydrogen abstraction reactions produced light naphtha fraction is an ideal green feedstock for from decalin are based on similarities with methyl cyclohexane existing processes like steam cracking, but contains higher pyrolysis reactions. Due to the high complexity and the high amounts of oxygenates and cyclic components (cyclohexane, number of carbon atoms, the size of the automatic generated cyclopentane) than similar, fossil-derived feedstocks. To date, network increases fast. For this reason, severe constraints are these cyclic compounds, and in particular polycyclic and used in the generation of the decalin model and stereochemistry substituted monocyclic alkanes, have been disregarded to a is not considered. The final kinetic models for the pyrolysis of large extent for kinetic studies compared to paraffinic species. methyl cyclohexane an decalin contain 4,113 species and 8,333 In this study, the automatic kinetic model generation tool reactions and 3,370 species and 19,493 reactions respectively. Genesys is used to construct pyrolysis mechanisms for decalin and methyl cyclohexane, as respective reference components III. METHYL CYCLOHEXANE: RESULTS AND DISCUSSION for the polycyclic and substituted monocyclic alkanes. A. Literature reported experimental data Validation of these mechanisms is done with literature reported experimental data. The developed kinetic model for methyl cyclohexane pyrolysis is validated against
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