Direct use of humic acid mixtures to construct efficient Zr-containing catalysts for Meerwein–Ponndorf–Verley reactions

Sha, Yingying; Xiao, Zhenhuan; Zhou, Huacong; Yang, Keli; Song, Yinmin; Li, Na; He, Rong; Zhi, Keduan; Liu, Quansheng

doi:10.1039/c7gc01925d

Cited by 62 publications

(37 citation statements)

References 60 publications

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“…Nonetheless, the gradual deactivation of the catalyst was observed due to Al species leaching. (Table 3, entry 3) [151]. Furthermore, Li et al synthesized recyclable Hf-phenylphosphonate nanohybrids (PhP-Hf) via the assembly of phenylphosphonate with HfCl 4 .…”

Section: Zr-based and Other Catalystsmentioning

confidence: 99%

Recent Advances in Catalytic Hydrogenation of Furfural

et al. 2019

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Furfural has been considered as one of the most promising platform molecules directly derived from biomass. The hydrogenation of furfural is one of the most versatile reactions to upgrade furanic components to biofuels. For instance, it can lead to plenty of downstream products, such as (tetrahydro)furfuryl alcohol, 2-methyl(tetrahydro)furan, lactones, levulinates, cyclopentanone(l), or diols, etc. The aim of this review is to discuss recent advances in the catalytic hydrogenation of furfural towards (tetrahydro)furfuryl alcohol and 2-methyl(tetrahydro)furan in terms of different non-noble metal and noble metal catalytic systems. Reaction mechanisms that are related to the different catalytic materials and reaction conditions are properly discussed. Selective hydrogenation of furfural could be modified not only by varying the types of catalyst (nature of metal, support, and preparation method) and reaction conditions, but also by altering the reaction regime, namely from batch to continuous flow. In any case, furfural catalytic hydrogenation is an open research line, which represents an attractive option for biomass valorization towards valuable chemicals and fuels.FA is a very important monomer for the synthesis of furan resins, which are widely used in thermoset polymer matrix composites, cements, adhesives, coatings, and casting/foundry resins. This molecule is also used as a non-reactive diluent for epoxy resin, a modifier for phenolic and urea resins, an oil well, and a carbon binder. Furthermore, the salt of FA is used in the synthesis of lysine, vitamin C, lubricants, and plasticizers [22,23]. Moreover, it should be highlighted that FA is also an important intermediate for the production of further hydrogenation products (as shown in Scheme 1), such as 2-methylfuran (MF), a potential alternative fuel with better combustion performance and higher Research Octane Number (RON = 103) than that of gasoline (RON = 96.8) [24]. In other applications, MF is used in perfume intermediates, chloroquine lateral chains in medical intermediates, and as a raw material for the production of chrysanthemate pesticides [25].Moreover, tetrahydrofurfuryl alcohol (THFA) can be used as a green solvent in the pharmaceutical industry and, in addition, it constitutes an outstanding intermediate to produce dihydropyran [26], pyridine [27], tetrahydrofuran, and pentan-1,5-diol [28][29][30]. Particularly, the latest molecule is an important monomer in the plastics industry. Furthermore, 2-methyltetrahydrofuran (MTHF) is quite engaging for its possible applications in organometallic chemistry, as well as in organic reactions that are related to organocatalysis, biotransformations, and biomass processing [31]. Catalysts 2019, 9, 796 3 of 33 Catalysts 2018, 8, x FOR PEER REVIEW 3 of 36 Scheme 1. Illustrative representation of reaction pathways in furfural hydrogenation.Other downstream products of furfural hydrogenation, such as (tetrahydro)furan [32], tetrahydrofurfural [33], lactones [34][35][36][37], levulinates [38,39], cyclopentanone...

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Section: Zr-based and Other Catalystsmentioning

confidence: 99%

Recent Advances in Catalytic Hydrogenation of Furfural

et al. 2019

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“…As shown in N 2 adsorptiondesorption isotherm (Figure 1d), the surface area and pore volume of Zr-IDA were 225 m 2 g À 1 and 0.549 cm 3 g À 1 , respectively. TGA analysis showed that the prepared catalyst had a low weight loss of 3.5 % at 200°C as a result of desorption of water and ethanol previously adsorbed on the catalyst [17] and had good stability at reaction temperatures (below 200°C) (Figure S3 †). About 50 % wt can be retained even at 800°C, manifesting a high zirconium content in Zr-IDA.…”

Section: Resultsmentioning

confidence: 99%

A Zirconium Indazole Carboxylate Coordination Polymer as an Efficient Catalyst for Dehydrogenation‐Cyclization and Oxidative Coupling Reactions

Sang

Tao

et al. 2020

ChemPlusChem

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Rational ligand design is crucial for achieving widespread applications of coordination polymers. The preparation, structural characterisation, and catalytic applications of zirconium (IV) coordination polymer (Zr-IDA), which was derived from 1-(carboxymethyl)-1H-indazole-5-carboxylic acid are reported. The Zr-IDA catalyst contains porous and highly crystalline particles with a quasi-spherical morphology around 100 nm in size, and Zr was coordinated with both O and N as shown by FT-IR and XPS measurements. Importantly, the Zr-IDA catalyst shows great activity, selectivity and stability in the oxidative coupling of benzyl cyanides with tert-butyl hydroperoxide to afford tertbutyl peresters, and the dehydrogenation cyclization of ophenylenediamines with aromatic alcohols to afford 1,2-disubstituted benzimidazole derivatives. Mechanistic investigations were carried out to study these reactions and the developed catalytic system in more detail.[a] Dr.

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“…It is exciting that the Ni–Fe (3/1) LDH catalyst has been proved to have a higher than 90% selectivity of the target products. It can also been seen that that the reaction of aldehydes is easier than that of ketones, because of the steric effect and the electron giving effect of alkyl in ketones…”

Section: Resultsmentioning

confidence: 99%

“…This process employs inexpensive and abundant alcohol to avoid the large number of problems caused by the use of hydrogen. For example, in recent years, the application of Zr‐ and Hf‐based catalysts to CTH reaction has always been the focus, including Li‐Zr‐BEA, Hf‐BEA, PhP‐Hf, Zr‐Has, Zr‐PhyA, ZrPN, and Zr‐FDCA‐T etc., which demonstrated good catalytic performance. In addition, various metal oxides have been discovered to catalyze the reduction of FF by hydrogen transfer, such as MgAlO x , La 2 O 3 , and Al 2 O 3 .…”

Section: Introductionmentioning

confidence: 99%

Catalytic transfer hydrogenation of furfural into furfuryl alcohol over Ni–Fe‐layered double hydroxide catalysts

Wang

et al. 2019

J Chinese Chemical Soc

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Layered double hydroxides (LDHs) and their derivatives have been reported to be widely used as heterogeneous catalysts in various reactions. Herein, Ni‐Fe LDHs with the controlled Ni/Fe molar ratios (2:1, 3:1, 4:1) were synthesized via an easy hydrothermal method, which were used to catalyze the selective reduction of biomass‐derived furfural into furfuryl alcohol using 2‐propanol as a H‐donor under autogenous pressure and characterized using FT‐IR, XRD, TGA, BET, SEM, NH3‐TPD, and CO2‐TPD. It was found that the LDH with a Ni/Fe molar ratio of 3:1 demonstrated the best catalytic activity among the LDHs with different Ni/Fe molar ratios, which showed 97.0% conversion of furfural and 90.2% yield of furfuryl alcohol at 140°C for 5 hr. This was attributable to the synergistic effect of acidic sites and basic sites of the catalyst.

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Direct use of humic acid mixtures to construct efficient Zr-containing catalysts for Meerwein–Ponndorf–Verley reactions

Abstract: Humic acid (HA) mixtures from lignite could be directly used to construct Zr-HAs catalysts for MPV reaction of carboxyl compounds.

Cited by 62 publications

References 60 publications

Recent Advances in Catalytic Hydrogenation of Furfural

Recent Advances in Catalytic Hydrogenation of Furfural

A Zirconium Indazole Carboxylate Coordination Polymer as an Efficient Catalyst for Dehydrogenation‐Cyclization and Oxidative Coupling Reactions

Catalytic transfer hydrogenation of furfural into furfuryl alcohol over Ni–Fe‐layered double hydroxide catalysts

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