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Molybdenum/Tungsten-Carbide and Nickel- Phosphide As Emerging Catalysts for Deoxygenation Reactions

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Molybdenum/Tungsten-Carbide and Nickel- Phosphide As Emerging Catalysts for Deoxygenation Reactions Molybdenum/tungsten-carbide and nickel- phosphide as emerging catalysts for deoxygenation reactions Luana Souza Macedo Thesis committee Promotors Prof. Dr J.H. Bitter Professor of Biobased Chemistry and Technology Wageningen University & Research Prof. Dr V. Teixeira da Silva (in memoriam) Associate professor, Chemical Engineering Program, Alberto Luiz Coimbra Institute of Engineering Pos-graduation and Research (COPPE) Federal University of Rio de Janeiro, Brazil Other members Prof. Dr J. van der Gucht, Wageningen University & Research Prof. Dr K. Seshan, University of Twente, Enschede Prof. Dr P.C.A. Bruijnincx, Utrecht University Dr R. Gosselink, BASF, Utrecht This research was conducted under the auspices of the Graduate School VLAG (Advanced studies in Food Technology, Agrobiotechnology, Nutrition and Health Sciences). Molybdenum/tungsten-carbide and nickel- phosphide as emerging catalysts for deoxygenation reactions Luana Souza Macedo Thesis submitted in fulfilment of the requirements for the degree of doctor at Wageningen University by the authority of the Rector Magnificus, Prof. Dr A.P.J. Mol, in the presence of the Thesis Committee appointed by the Academic Board to be defended in public on Tuesday 29 January 2019 at 1.30 p.m. in the Aula. Luana Souza Macedo Molybdenum/tungsten-carbide and nickel-phosphide as emerging catalysts for deoxygenation reactions, 195 pages. PhD thesis, Wageningen University, Wageningen, the Netherlands (2019) With references, with summary in English ISBN 978-94-6343-547-5 DOI http://doi.org/10.18174/464686 Table of contents Chapter 1 Introduction .................................................................................................7 Chapter 2 Stability of transition metal carbides in liquid phase reactions relevant for biomass-based conversion ����������������������������������������������������������������������27 Chapter 3 Activated carbon, carbon nanofibers and carbon-covered alumina as support for W2C in stearic acid hydrodeoxygenation ����������������������������������������47 Chapter 4 On the pathways of hydrodeoxygenation over supported Mo-carbide and Ni-phosphide .......................................................................................71 Chapter 5 Influence of synthesis method on molybdenum carbide crystal structure and catalytic performance in stearic acid hydrodeoxygenation ��������������������������89 Chapter 6 Particle size effects in nickel phosphide supported on activated carbon as catalyst for stearic acid deoxygenation �������������������������������������������������������� 111 Chapter 7 On the role of different noble metals in the synthesis of nickel phosphides and their use in thiophene hydrodesulfurization �������������������������������������������� 131 Chapter 8 General discussion ������������������������������������������������������������������������������������ 153 Appendices Supplementary information ........................................................................ 171 Summary ............................................................................................... 187 Acknowledgments ................................................................................. 189 About the author ����������������������������������������������������������������������������������� 191 Chapter 1 Introduction 8 1. General aspects of catalysts Catalysts are at the heart of industrial chemical transformations and approximately 90% of all chemical industry products require a catalytic step [1]. In 2014, the global demand of catalysts was about US$ 33.5 billion and a steady increase in this demand is expected in the next years [2]. To meet this growing market demand, both governments and catalyst producers are investing in research and development of new catalysts, products, processes and technologies [2]. Catalyst technologies can be grouped into three main areas of relevant economical interest: petroleum refining to fuels or to chemicals and environmental catalysis [3]. Petroleum refining includes several processes, such as catalytic reforming, fluid catalytic cracking, hydrocracking and hydrotreating. Chemicals manufacturing is commonly defined according to reaction type, for example hydrogenation, polymerization and oxidation. Finally, environmental catalysis is often related to cleaning off gases or to the conversion of bio-based sources into marketable products. To advance the catalysis field it is essential to understand the relationship between catalyst properties and performance [4]. For example, it has been shown that catalyst properties like particle size, acidity and support can significantly influence catalyst performance [5 – 7]. Hence, the steering of such properties is essential to improve the performance of catalysts making their use attainable in the industry. For instance, an interesting new group of catalysts that would be benefited by this understanding of catalyst properties–performance relationship is the transition metal carbides and phosphides, which are the catalysts under study in this thesis. These catalysts are potential substitutes of the limited available noble metals. For several reactions, it has been shown that carbide and phosphide based catalysts can display similar or even better catalytic performance than noble metal catalysts [8 – 13]. Since the seminal work of Levy and Boudart [14] on water formation from H2 and O2 at room temperature over W-carbide, it became clear that transition metal carbides are efficient catalysts for reactions that involve hydrogen activation, such as ammonia synthesis and decomposition, hydrogenation, hydrogenolysis, hydro-isomerization, methanation and hydroprocessing [4]. Metal phosphides are also active catalysts in hydrotreatment reactions (Li et al. [15]), thus transition metal carbides and phosphides hold great potential as they are more available and can be at least equally active as compared to noble metals. In this thesis this group of non-noble metal catalysts – the transition metal carbides and phosphides – will be investigated and we will focus on the study of catalyst properties-performance relations and the influence of synthesis conditions 9 on the catalyst properties. For that, we apply transition metal carbides and phosphides for the deoxygenation of vegetable oil. The deoxygenation of vegetable oils can yield different products such as aldehydes, alcohols, olefins and paraffins, which are relevant for industry as chemical building blocks or as fuels [16]. The use of biobased renewable feedstock in the production of chemical building blocks and fuels is essential to ensure a more sustainable future. 2. Some challenges for the biobased economy A biobased economy can be defined as an economy where renewable biomass (organic matter) instead of fossil resources (i.e. gas, oil and coal) is at the base of the production chain [17]. The interest in the use of biomass as feedstock increased significantly in the past few years to compensate the expected decrease in easily accessible oil availability and the need to decrease greenhouse gas emissions [18]. 2.1 Crude oil for fuel and chemicals production Currently the worlds’ demand for crude oil is about 90 million barrels per day [19]. Figure 1 displays an overview of the oil demand per sector. The transportation sector is responsible for 57% of the total oil demand, divided in road transportation (44%), aviation (6%), marine bunkers (5%) and rail and domestic waterways (2%). The non-transportation sectors, ‘other industry’, which primarily comprises iron, steel, glass and cement production, construction and mining, accounts for 15% of total oil demand, followed by petrochemicals (11% of total demand), residential/ commercial/agriculture (10% of total demand) and electricity generation (7% of total demand) [19]. Currently crude oil is the dominant energy carrier (Figure 2). From a total of 1.3x104 million tonnes oil equivalent in 2015, the consumption of primary energy worldwide was more than 85% fossil fuel (oil, coal and natural gas), followed by 7% hydropower, 4% nuclear energy and 3% renewables [20]. 10 Figure 1. Global oil demand per sector in 2014 [19]. Figure 2. Regional consumption of energy carriers in 2015 [20]. In addition, crude oil is also a feedstock to produce diverse chemicals. According to the review by Eneh [21], the production of chemicals from petroleum has increased since World War II and Table 1 displays examples of the petrochemicals and their products. Table 1. Petrochemicals and their products [21 – 24]. Petrochemical Products Carbon black, ethyne, synthesis gas, Methane halogenmethanes, hydrogen cyanide Ethyne Chloroethene compounds, ethanol 11 Chloroethene compounds Polymers, e.g. poly(chloroethane) Synthesis gas Methanol, ammonia Methanol Methanal Poly(ethene), ethylbenzene, epoxyethane, Ethene ethanol, 1,2-dichloroethane Ethylbenzene Phenylethene Epoxyethane Ethane-1,2-diol Ethanol Ethanal 1,2-dichloroethane Chloroethene Phenylethene Poly(phenylethane) Chloroethene Poly(chloroethene) Polypropene, propenontrile, propan-2-ol, Propene 1-(methylethyl)benzene, propane-1,2,3-triol, methylbuta-1,3-diene Propenontrile Acrylnitrile-based polymers Propan-2-ol Propanone Propanone Perspex 1-(methylethyl)benzene Phenol Phenol Bakelite-type resins Propane-1,2,3-triol Alkyd resins Methylbuta-1,3-diene Artificial rubbers But-1-ene, But-2-ene Buta-1,3-diene, poly(butene) 2-Methylpropene 2-methylpropan-2-ol Buta-1,3-diene Butadiene-based polymers Phenylethene, cyclobenzene, phenol, Benzene phenylamine Methylbenzene
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