Catalyst studies on the ring opening of tetrahydrofuran–dimethanol to 1,2,6-hexanetriol

Buntara, Teddy; Melián‐Cabrera, Ignacio; Tan, Qiaohua; Fierro, J.L.G.; Neurock, Matthew; Vries, Johannes G. de; Heeres, Hero J.

doi:10.1016/j.cattod.2013.04.012

Cited by 67 publications

(68 citation statements)

References 49 publications

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“…Biomass‐derived furanic compounds have been widely investigated for producing hydrocarbon fuels through ring opening and hydrodeoxygenation. When using THF as solvent for catalytic hydrodeoxygenation, the reaction conditions were tuned to avoid the ring opening of THF . Besides, ether compounds such as THF and dioxane can be oxidized into peroxides in air, which require special attention due to their explosive nature .…”

Section: Processing Challenges For Organic Solventsmentioning

confidence: 99%

“…When using THF as solvent forc atalytic hydrodeoxygenation, the reactionc onditions were tuned to avoid the ring opening of THF. [249] Besides, ether compounds such as THF and dioxane can be oxidized into peroxides in air, which require special attention due to their explosive nature. [250] Similarly,a lcohols olvents can also be dehydrated into olefins at temperatures above 160 8Ci nt he presence of acid catalysts.…”

Section: Stability (Decomposed or Reacted)mentioning

confidence: 99%

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Organic Solvent Effects in Biomass Conversion Reactions

2015

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Transforming lignocellulosic biomass into fuels and chemicals has been intensely studied in recent years. A large amount of work has been dedicated to finding suitable solvent systems, which can improve the transformation of biomass into value‐added chemicals. These efforts have been undertaken based on numerous research results that have shown that organic solvents can improve both conversion and selectivity of biomass to platform molecules. We present an overview of these organic solvent effects, which are harnessed in biomass conversion processes, including conversion of biomass to sugars, conversion of sugars to furanic compounds, and production of lignin monomers. A special emphasis is placed on comparing the solvent effects on conversion and product selectivity in water with those in organic solvents while discussing the origins of the differences that arise. We have categorized results as benefiting from two major types of effects: solvent effects on solubility of biomass components including cellulose and lignin and solvent effects on chemical thermodynamics including those affecting reactants, intermediates, products, and/or catalysts. Finally, the challenges of using organic solvents in industrial processes are discussed from the perspective of solvent cost, solvent stability, and solvent safety. We suggest that a holistic view of solvent effects, the mechanistic elucidation of these effects, and the careful consideration of the challenges associated with solvent use could assist researchers in choosing and designing improved solvent systems for targeted biomass conversion processes.

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Section: Processing Challenges For Organic Solventsmentioning

confidence: 99%

Section: Stability (Decomposed or Reacted)mentioning

confidence: 99%

Organic Solvent Effects in Biomass Conversion Reactions

2015

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“…Supported bimetallic catalysts composed of ar educible noble metal (Pt, Ir,R h, Pd) and an oxophilic metal (such as Re) have been described for the conversion of biomass-derived feedstock, the aqueous-phase reforming of biomass-derived oxygenates, [52,53] secondary CÀOb onds hydrogenolysis in ab road range of polyols including glycerol [54][55][56][57][58] and cyclic ethers, [48,49,56,59,60] andf or amide, [61] acid, [62] and aminoa cid [63] hydrogenation. As described in recent publications, Re promotion may generate ab ifunctionalc atalystt hat possesses both metal and Brønsted acid sites.…”

Section: Tentative Mechanismmentioning

confidence: 99%

Insights into the Oxidation State and Location of Rhenium in Re‐Pd/TiO₂ Catalysts for Aqueous‐Phase Selective Hydrogenation of Succinic Acid to 1,4‐Butanediol as a Function of Palladium and Rhenium Deposition Methods

Tapin

Aouine

et al. 2015

ChemCatChem

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“…[11,16] It was also shown that supportsw ith ah igh IEP (e.g., Al 2 O 3 )f avour hydrogenation of the ring whereas supports exhibiting Brønsted acidity,s uch as SiO 2 ,g enerate polyols and polymers via ring opening. [15,20] Despite theser eports, [11,13,15,16,20] whichs uggestt hat Ni metal and Al 2 O 3 favour the formation of THFDM, the hydrogenation of HMF over Ni on Al 2 O 3 has not been studied in asystematic manner.…”

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confidence: 99%

Catalytic Response and Stability of Nickel/Alumina for the Hydrogenation of 5‐Hydroxymethylfurfural in Water

et al. 2016

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The catalytic response of Ni on Al2O3 obtained from Ni-Al layered double hydroxides was studied for the liquid-phase hydrogenation of hydroxymethyl furfural to tetrahydrofuran-2,5-diyldimethanol (THFDM) in water. The successive calcination and reduction of the precursors caused the removal of interlayer hydroxyl and carbonate groups and the reduction of Ni(2+) to Ni(0). Four reduced mixed oxide catalysts were obtained, consisting of different amount of Ni metal contents (47-68 wt%) on an Al-rich amorphous component. The catalytic activity was linked to Ni content whereas selectivity was mainly affected by reaction temperature. THFDM was formed in a stepwise manner at low temperature (353 K) whereas 3-hydroxymethyl cyclopentanone was generated at higher temperature. Coke formation caused deactivation; however, the catalytic activity can be regenerated using heat treatment. The results establish Ni on Al2O3 as a promising catalyst for the production of THFDM in water.

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Catalyst studies on the ring opening of tetrahydrofuran–dimethanol to 1,2,6-hexanetriol

Cited by 67 publications

References 49 publications

Organic Solvent Effects in Biomass Conversion Reactions

Organic Solvent Effects in Biomass Conversion Reactions

Insights into the Oxidation State and Location of Rhenium in Re‐Pd/TiO₂ Catalysts for Aqueous‐Phase Selective Hydrogenation of Succinic Acid to 1,4‐Butanediol as a Function of Palladium and Rhenium Deposition Methods

Catalytic Response and Stability of Nickel/Alumina for the Hydrogenation of 5‐Hydroxymethylfurfural in Water

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Catalyst studies on the ring opening of tetrahydrofuran–dimethanol to 1,2,6-hexanetriol

Cited by 67 publications

References 49 publications

Organic Solvent Effects in Biomass Conversion Reactions

Organic Solvent Effects in Biomass Conversion Reactions

Insights into the Oxidation State and Location of Rhenium in Re‐Pd/TiO2 Catalysts for Aqueous‐Phase Selective Hydrogenation of Succinic Acid to 1,4‐Butanediol as a Function of Palladium and Rhenium Deposition Methods

Catalytic Response and Stability of Nickel/Alumina for the Hydrogenation of 5‐Hydroxymethylfurfural in Water

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Insights into the Oxidation State and Location of Rhenium in Re‐Pd/TiO₂ Catalysts for Aqueous‐Phase Selective Hydrogenation of Succinic Acid to 1,4‐Butanediol as a Function of Palladium and Rhenium Deposition Methods