Production of <i>p</i>-xylene from bio-based 2,5-dimethylfuran over high performance catalyst WO<sub>3</sub>/SBA-15

Feng, Xinqiang; Shen, Chun; Ji, Kaiyue; Yin, Jianjun; Tan, Tianwei

doi:10.1039/c7cy01530e

Cited by 32 publications

(26 citation statements)

References 51 publications

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“…Zeolites and modified zeolites are the most common type of catalysts for this transformation. The mechanism of this process was thoroughly studied both theoretically and experimentally. − Despite harsh reaction conditions, this transformation is a real breakthrough in the field of biomass aromatization since p -xylene is a compound of general importance for the chemical industry. …”

Section: Synthesis Of P-xylene From 25-dimethylfuranmentioning

confidence: 99%

Biobased C₆-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Kucherov

Romashov

Averochkin

et al. 2021

ACS Sustainable Chem. Eng.

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Rapid development in the area of cellulose biomass conversion to furanic platform chemicals has led to expectations of their valuable practical use. Impressive research progress in this direction has resulted in several achievements but at the same time identified a key challengethe necessity to produce aromatic compounds. In this perspective, we analyze the current stage of development of the furanics-tobenzene conversion process (F2B process) in connection with a bioderived route to aromatic compounds. Cycloaddition reactions between bioderived C 6 -furans as diene components and alkene/alkyne units are discussed in detail, followed by considering the subsequent aromatization reaction. Progress in the development of the F2B process and future challenges are outlined in this perspective. The key role of the F2B process in the overall biomass to aromatics transformation is discussed in view of the implementation of carbon neutral sustainable technologies in practice.

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Section: Synthesis Of P-xylene From 25-dimethylfuranmentioning

confidence: 99%

Biobased C₆-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Kucherov

Romashov

Averochkin

et al. 2021

ACS Sustainable Chem. Eng.

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“…[22,34–35] Hence, H‐SAPO‐34 with the small pore size exhibited the low DMF conversion. For another, it was also illustrated that Lewis acid sites showed better performances in inhibiting side reactions than Brønsted acid sites . It can be found in Table that H‐SAPO‐34 had a larger proportion of Lewis acid sites than the other three catalysts.…”

Section: Resultsmentioning

confidence: 86%

“…They showed better catalytic performances than the commercial H‐Beta zeolites, which was attributed to the moderate acidity and appropriate porous structure . On the other hand, some reports claimed that compared with Brønsted acids, Lewis acids are superior in inhibiting some side reactions, such as formation of 2,5‐hexanedione (HDO) from hydrolysis of DMF . For instance, it was reported that Lewis acid zeolite Zr‐BEA with high pX selectivity of 90% and DMF conversion of 99% had longer catalyst life and slower production rate of HDO than Al‐BEA .…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, some reports claimed that compared with Brønsted acids, Lewis acids are superior in inhibiting some side reactions, such as formation of 2,5‐hexanedione (HDO) from hydrolysis of DMF . For instance, it was reported that Lewis acid zeolite Zr‐BEA with high pX selectivity of 90% and DMF conversion of 99% had longer catalyst life and slower production rate of HDO than Al‐BEA . And a selectivity of 88.0% to pX and carbon balance of 90.1% was obtained over the WO3/SBA‐15 catalyst, owing to the low selectivity to hydrolysis and condensation .…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Conversion of Biomass‐Derived 2, 5‐Dimethylfuran into Renewable p‐Xylene over SAPO‐34 Catalyst

et al. 2020

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In this work, ∼75% selectivity to p‐xylene (pX) has been achieved from biomass‐derived 2, 5‐dimethylfuran (DMF) and ethylene over SAPO‐34. The pX selectivity reached a maximum after 12 h and maintained significantly stable when prolonging the reaction time. This might be due to the small Brønsted/Lewis ratio and the hierarchical structures of SAPO‐34. Stability tests suggested that SAPO‐34 may be resistant to deactivation under the optimized reaction conditions. Besides, it was found that SAPO‐11 showed similar catalytic performances to SAPO‐34. In summary, these novel SAPO catalysts might provide an alternative for the selective production of renewable aromatics from biomass‐derived feedstock.

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“…The direct catalytic route to p -xylene via the Diels–Alder cycloaddition of biomass-derived 2,5-dimethylfuran and ethylene over solid acid catalysts has previously been investigated. − Cho et al has reported 97% yield of p -xylene from 2,5-dimethylfuran (DMF) and ethylene at >99% conversion of DMF using phosphoric acid supported on siliceous zeolites including dealuminated zeolite BEA (P-BEA) and self-pillared pentasil (P-SPP). This is a significant improvement over other Brønsted acid catalysts, such as Al-BEA, as well as Lewis acid catalysts, such as Zr-BEA and Sn-BEA. , Unlike other Brønsted acid zeolite catalysts (e.g., Al-BEA) which catalyze the formation of side products, such as the alkylation of aromatic species with ethylene and oligomerization of DMF with aromatics, P-BEA and P-SPP mitigate the formation of these side products .…”

Section: Introductionmentioning

confidence: 99%

Role of Silica Support in Phosphoric Acid Catalyzed Production of p-Xylene from 2,5-Dimethylfuran and Ethylene

Gulbinski

Ren

Vattipalli

et al. 2020

Ind. Eng. Chem. Res.

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p-Xylene is a commodity chemical of industrial importance for terephthalic acid production, for which renewable sourcing from naturally abundant lignocellulosic biomass is highly desired. Previous work demonstrated that phosphoric acid stabilized on siliceous zeolite supports (e.g., P-BEA, P-SPP) exhibits high selectivity toward p-xylene (>97%) from 2,5-dimethylfuran (DMF) and ethylene. However, the effect of the support and the contribution of heterogeneous versus homogeneous phosphoric acid on the observed catalytic behavior in the solvated reaction system have not been addressed. Here, we determine the phosphoric acid catalytic activity for DMF conversion and its selectivity to p-xylene when it is supported on a silica support as well as in the absence of a support. Specifically, phosphoric acid catalysis was studied in three different scenarios: (1) phosphoric acid was added in the liquid reaction mixture in the absence of any solid support, (2) phosphoric acid was added in the liquid reaction mixture along with inert silica support including siliceous zeolite (i.e., allowing for phosphoric acid–support assembly to proceed in the reaction mixture), and (3) phosphoric acid was first impregnated on the siliceous zeolite support and then the preassembled supported phosphoric acid catalyst was added in the liquid reaction mixture. We found that the reaction rate and selectivity to p-xylene are different in the above scenarios reflecting the effect of the solid support on the catalytic performance of phosphoric acid. In scenario 1, a low concentration of phosphoric acid (1.7 mM) in the absence of any solid support exhibited high selectivity to p-xylene (80% selectivity to p-xylene at 60% conversion of DMF), which decreased with increasing acid concentration. The selectivity to p-xylene and activity of phosphoric acid significantly increased by adding a silica support into the reaction system (scenario 2). This improvement was attributed to phosphoric acid partial association with the surface of the silica support under the reaction conditions (in situ catalyst assembly). Phosphoric acid predeposited on siliceous zeolite supports (e.g., P-BEA, P-SPP) synthesized via impregnation prior to the reaction (scenario 3) catalyzed the reaction heterogeneously without noticeable leaching and exhibited the highest activity and selectivity to p-xylene, suggesting an important role of the silica support and the need to ensure that phosphoric acid acts as a heterogeneous catalyst in order to accomplish selective conversion of DMF to p-xylene.

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Production of p-xylene from bio-based 2,5-dimethylfuran over high performance catalyst WO₃/SBA-15

Abstract: Mesoporous solid acid catalyst WO3/SBA-15 possessing mainly Lewis acids exhibits high performance for the production of bio-based PX.

Cited by 32 publications

References 51 publications

Biobased C₆-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Biobased C₆-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Catalytic Conversion of Biomass‐Derived 2, 5‐Dimethylfuran into Renewable p‐Xylene over SAPO‐34 Catalyst

Role of Silica Support in Phosphoric Acid Catalyzed Production of p-Xylene from 2,5-Dimethylfuran and Ethylene

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Production of p-xylene from bio-based 2,5-dimethylfuran over high performance catalyst WO3/SBA-15

Abstract: Mesoporous solid acid catalyst WO3/SBA-15 possessing mainly Lewis acids exhibits high performance for the production of bio-based PX.

Cited by 32 publications

References 51 publications

Biobased C6-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Biobased C6-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Catalytic Conversion of Biomass‐Derived 2, 5‐Dimethylfuran into Renewable p‐Xylene over SAPO‐34 Catalyst

Role of Silica Support in Phosphoric Acid Catalyzed Production of p-Xylene from 2,5-Dimethylfuran and Ethylene

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Production of p-xylene from bio-based 2,5-dimethylfuran over high performance catalyst WO₃/SBA-15

Biobased C₆-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks

Biobased C₆-Furans in Organic Synthesis and Industry: Cycloaddition Chemistry as a Key Approach to Aromatic Building Blocks