Selective hydrodeoxygenation of lignin-related 4-propylphenol into n-propylbenzene in water by Pt-Re/ZrO2 catalysts

Ohta, Hidetoshi; Feng, Bo; Kobayashi, Hirokazu; Hara, Kenji; Fukuoka, Atsushi

doi:10.1016/j.cattod.2014.01.022

Cited by 69 publications

(46 citation statements)

References 44 publications

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“…Consequently synergistic effects can be observed which lead to improved catalytic activity, selectivity and even stability [98]. In fact, bimetallic catalysts are widely used and have proven records in a number of industrial processes [66,67,99]. However, the feasibility and effectiveness of the bimetallic strategy has not been investigated for lignin hydrogenolysis until recently.…”

Section: Bimetallic Systems In Lignin Hydrogenolysismentioning

confidence: 98%

“…Various strategies including thermal decomposition [11,62], oxidation [63,64], hydrogenolysis [65][66][67], decarboxylation and decarbonylation were employed to convert lignin model compounds or real lignin into aromatics [68], solvents, liquid fuels, bioethanol or other valuable chemicals. Among these methods, hydrogenolysis of C-O linkages in lignin, in which H 2 is used to cleave the C-O bond over a metal catalyst, is regarded as an effective way to transform lignin into depolymerized aromatic platform compounds.…”

Section: Lignin Hydrogenolysis: Overviewmentioning

confidence: 99%

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Novel Catalytic Systems to Convert Chitin and Lignin into Valuable Chemicals

Chen

Yan

2014

Catal Surv Asia

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This review briefs the emerging strategies for the designing of catalysts and catalytic systems to upgrade waste biomass into value-added chemicals, with an emphasis on the efforts and advances in our group. The review covers the valorization of chitin and lignin materials, which are most abundant N-containing and the most abundant aromatic polymers, respectively. In the chitin part, we show case existing examples on chitin monomer and chitin transformation into renewable, N-containing chemicals. Oxidation, hydrolysis, dehydration reactions will be introduced. In lignin part we mainly introduce novel catalyst for lignin hydrogenolysis, in particular Ni based monometallic and bimetallic catalysts. The structure-activity correlations will be discussed in detail. We finally describe some of the undergoing works in the group and highlight a few potential directions worth investigation in the future.

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Section: Bimetallic Systems In Lignin Hydrogenolysismentioning

confidence: 98%

Section: Lignin Hydrogenolysis: Overviewmentioning

confidence: 99%

Novel Catalytic Systems to Convert Chitin and Lignin into Valuable Chemicals

Chen

Yan

2014

Catal Surv Asia

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“…Considering that the bond dissociation energy of C aromatic -OH is 84 kJ/mol higher than that of C aliphatic -OH (Furimsky, 2000), it has been suggested that the formation of aromatics is through the HYD path instead of the DDO path (Ohta et al, 2014). In the presence of acid sites, phenol is first hydrogenated to cyclohexanol, then dehydrated to cyclohexene, and finally dehydrogenated to benzene (Ohta et al, 2014) following the HYD path.…”

Section: Kinetic Fittings and Reaction Network Analysismentioning

confidence: 98%

“…In the presence of acid sites, phenol is first hydrogenated to cyclohexanol, then dehydrated to cyclohexene, and finally dehydrogenated to benzene (Ohta et al, 2014) following the HYD path. In this mechanism, cyclohexene is the key intermediate that determines the final distribution of benzene/cyclohexane.…”

Section: Kinetic Fittings and Reaction Network Analysismentioning

confidence: 99%

“…At 2 MPa and 300 1C, propylbenzene was the major product during hydrodeoxygenation of 4-propylphenol on a Pt-Re/ZrO 2 catalyst. It has been suggested that the major reaction pathway is hydrogenation to 4-propylcyclohexanol first, and then dehydration to 4-propylcyclohexene, followed by dehydrogenation to propylbenzene (Ohta et al, 2014). For p-cresol hydrodeoxygenation on the supported Pd and Pt catalysts at 300 C and 8.3 MPa, toluene was the major product when water was used as solvent, but the major product was methylcyclohexane in a heptane solvent (Wan et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

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Vapor phase hydrodeoxygenation and hydrogenation of m-cresol on silica supported Ni, Pd and Pt catalysts

Chen

Yang

et al. 2015

Chemical Engineering Science

103

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Hydrodeoxygenation of Propylphenols on a Niobia‐Supported Platinum Catalyst: Ortho, Meta, Para Isomerism, Reaction Conditions, and Phase Equilibria

Escobedo

Mäkelä

Neuvonen

et al. 2020

Advanced Sustainable Systems

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managed responsibly. [2,3] Such renewable biofuels are especially promising for sustainable aviation. [4] The biopolymers that constitute lignocellulose can be broken down, among other means, by liquefaction. [5-7] Liquefaction relies on thermochemistry (200-400 °C) and on a liquid solvent, such as a high boiling point hydrocarbon. [6,7] The same solvent can be used in subsequent upgrading steps. The product of liquefaction is biocrude: a complex mixture of phenolics, furanics, cyclic ketones, carboxylic acids, and other compounds. [6] The high concentration of oxygenates renders biocrudes chemically unstable, poor in heating value, corrosive, highly viscous, and prone to form coke. [6,8] Hence, further upgrading is necessary, with a possible upgrading step being hydrodeoxygenation (HDO): a type of hydrotreatment, in which biocrude constituents react with dihydrogen on a heterogeneous catalyst, producing deoxygenated compounds and water. [8] Fittingly, HDO can proceed in the presence of an organic solvent. [7] Liquefaction biocrudes are highly unsaturated (60-65% carbon) and resemble lignin or pyrolysis liquids. [6] They are rich in phenolic compounds, and hence they are a potential source of bio-based aromatic hydrocarbons. Aromatic hydrocarbons are essential to the chemical industry, [9-12] and they are also required in fuels. [4] For example, international standards stipulate that jet fuel should contain 8% to 25% aromatics. [4,13,14] Although the abundant phenolics produced in liquefaction are suitable for conversion to aromatic hydrocarbons via HDO, the challenge, especially with alkylphenols, is that the aryl-hydroxyl bond is among the strongest in lignocellulose. [8] Furthermore, it is necessary to prevent the hydrogenation of the aromatic ring. Thus, in order to overcome these obstacles, it is pertinent to study the HDO of alkylphenols, for which catalyst development is essential. Many factors in the HDO process can influence the performance of a HDO catalyst. Some of these factors are the reaction medium, [15,16] the reaction temperature and pressure with their thermodynamic and kinetic effects, [17] and the ortho, meta, and para isomerism of alkylphenols. [18] Sulfided catalysts are considered conventional in commercial hydrotreatment. [19,20] Unfortunately, the activity of sulfided The alkylphenols found in liquefied lignocellulose could become a source of biobased aromatic hydrocarbons for fuel components. In the hydrodeoxygenation (HDO) of alkylphenols, hydroxyl groups must be removed while avoiding the hydrogenation of the aromatic ring. Here, the HDO of propylphenols is studied using a Pt/Nb 2 O 5 catalyst and n-tetradecane solvent. HDO experiments are performed using different reaction conditions of batch residence time (0-161 min g cat g reactant −1), pressure (20-30 bar H 2), and temperature (300-375 °C). HDO is studied with ortho-, meta-, and para-propylphenol. The influence of vapor-liquid equilibrium and chemical equilibrium are assessed using thermodynamic calculations. Almost full deoxygena...

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Selective hydrodeoxygenation of lignin-related 4-propylphenol into n-propylbenzene in water by Pt-Re/ZrO2 catalysts

Cited by 69 publications

References 44 publications

Novel Catalytic Systems to Convert Chitin and Lignin into Valuable Chemicals

Novel Catalytic Systems to Convert Chitin and Lignin into Valuable Chemicals

Vapor phase hydrodeoxygenation and hydrogenation of m-cresol on silica supported Ni, Pd and Pt catalysts

Hydrodeoxygenation of Propylphenols on a Niobia‐Supported Platinum Catalyst: Ortho, Meta, Para Isomerism, Reaction Conditions, and Phase Equilibria

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