The Critical Role of Water in the Ring Opening of Furfural Alcohol to 1,2-Pentanediol

Ma, Rongfang; Wu, Xin‐Ping; Tong, Tao; Shao, Zheng; Wang, Yanqin; Liu, Xiaohui; Xia, Qineng; Gong, Xue‐Qing

doi:10.1021/acscatal.6b02845

Cited by 95 publications

(66 citation statements)

References 26 publications

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“…This shows that indirect hydrogenolysis pathway (i. e., dehydration‐hydrogenation) is contributing in the ring‐opening THFA in the absence of water. Besides, only a small amount of 15PDO is obtained in the hydrogenolysis reaction in 1,4‐dioxane, suggesting the crucial role of water in the formation of 15PDO from THFA ,. DRIFTS measurements also prove the transformation of Lewis acid sites into Brønsted acid sites in the presence of water, as shown in Figure S3.…”

Section: Resultsmentioning

confidence: 73%

C−O Hydrogenolysis of Tetrahydrofurfuryl Alcohol to 1,5‐Pentanediol Over Bi‐functional Nickel‐Tungsten Catalysts

Soghrati

Poh

et al. 2018

ChemCatChem

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In this study, we report a series of bimetallic Ni−WOx catalyst for the ring‐opening of THFA into 15PDO. The structure‐performance relationship of the catalysts was discussed based on extensive characterization using techniques such as BET, H2‐TPR, NH3‐TPD, Pyr‐IR, IPA‐TPD‐MS, XRD, XPS and EXAFS/XANES. The acidity measurements show that higher W density leads to the higher amount of acid density, which could be assigned to the creation of Lewis acid sites mainly on the surface of the calcined catalysts. H2‐TPR profiles of Ni−WOx catalysts show that there is a strong interaction between Ni and W species, enhancing the reducibility of WOx. XRD measurements of calcined Ni−WOx catalysts reveal that the dispersion of Ni particles is enhanced after addition of WOx species. After reduction, different peaks corresponding to metallic Ni and WO3−x are identified for 10Ni−WOx catalysts, as well as new peak assigned to Ni−W intermetallic phase on 10Ni−30WOx catalyst. The formation of Ni−W intermetallic phase was further proved using XPS and EXAFS studies. THFA hydrogenolysis was also conducted under aqueous‐phase conditions over Ni−WOx catalysts, yielding up to 47 % selectivity to 15PDO, along with a highest combined C5 polyols (i. e., 15PDO and 125PTO) selectivity of approximately 64 %. However, the Ni−WOx catalytic system suffers from deactivation process due to the hydrothermal dissolution of the active phase. Further investigation reveals the better stability of metallic tungsten and Ni−W intermetallic phase (Ni4W) against leaching since their corresponding peaks in the XRD patterns of spent catalysts remains nearly unchanged. Finally, 1,4‐dioxane as an organic solvent was employed in THFA hydrogenolysis reaction, resulting in different product distribution, with a THP yield of around 54 %. The catalyst crystalline structure is preserved because of very low Ni and W leaching when 1,4‐dioxane is used as solvent.

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Section: Resultsmentioning

confidence: 73%

C−O Hydrogenolysis of Tetrahydrofurfuryl Alcohol to 1,5‐Pentanediol Over Bi‐functional Nickel‐Tungsten Catalysts

Soghrati

Poh

et al. 2018

ChemCatChem

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“…The conversion of furfural to valuable chemicals was attracting more attention as the consuming in fossil resources [2][3][4][5][6][7]. The main products from furfural were cyclopentanone [8][9][10][11][12], furfuryl alcohol (FA) [13][14][15][16], tetrahydrofurfuryl alcohol (THFA) [17][18][19][20][21][22][23][24][25][26][27][28][29][30], 1,2-pentanediol [31][32][33][34][35], furan [36,37], and methyl furan [38]. The THFA was a typical product from furfural through the hydrogenation of C=C and C=O in furfural.…”

Section: Introductionmentioning

confidence: 99%

Facile Preparation of Pd/UiO-66-v for the Conversion of Furfuryl Alcohol to Tetrahydrofurfuryl Alcohol under Mild Conditions in Water

et al. 2019

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The hydrogenation of furan ring in the biomass-derived furans is of great importance for the conversion of biomass to valuable chemicals. Fabrication of high activity and selectivity catalyst for this hydrogenation under mild conditions was one of the focuses of this research. In this manuscript, UiO-66-v, in which vinyl bonded to the benzene ring, was first prepared. Then, the uniformly distributed vinyl was used as the reductant for the preparation of Pd/UiO-66-v. The catalyst was characterized by X-ray diffraction, thermogravimetric, N2 physical adsorption/desorption, X-ray photoelectron spectroscopy, scanning electron microscope, transmission electron microscopy, energy dispersive spectrometer elemental mappings, and inductively coupled plasma atomic emission spectroscopy to find the Pd/UiO-66-v had a narrow palladium nanoparticles size of 3–5 nm and maintained the structure and thermal stability of UiO-66-v. The Pd/UiO-66-v was used for the hydrogenation of furfuryl alcohol to tetrahydrofurfuryl alcohol in water. 99% conversion of furfuryl alcohol was obtained with 90% selectivity to tetrahydrofurfuryl alcohol after reacted at 0.5 MPa H2, 303 K for 12 h. The Pd/UiO-66-v was proved to be effective for the hydrogenation of furan ring in furans and could be used for at least five times.

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“…Based on the experimental and theoretical studies on furan, some researchers have carried out further research on furan compounds. Ma et al 16 studied the process of furfuryl alcohol ring-opening and conversion to 1,2-pentanediol via platinum catalysis and veried the calculated results of the density functional theory by the isotopic tracer method. The results show that water molecules can obviously promote the ring opening of furfuryl alcohol.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic investigation of CO generation by pyrolysis of furan and its main derivatives

et al. 2019

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The Critical Role of Water in the Ring Opening of Furfural Alcohol to 1,2-Pentanediol

Cited by 95 publications

References 26 publications

C−O Hydrogenolysis of Tetrahydrofurfuryl Alcohol to 1,5‐Pentanediol Over Bi‐functional Nickel‐Tungsten Catalysts

C−O Hydrogenolysis of Tetrahydrofurfuryl Alcohol to 1,5‐Pentanediol Over Bi‐functional Nickel‐Tungsten Catalysts

Facile Preparation of Pd/UiO-66-v for the Conversion of Furfuryl Alcohol to Tetrahydrofurfuryl Alcohol under Mild Conditions in Water

Mechanistic investigation of CO generation by pyrolysis of furan and its main derivatives

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