Catalytic selective etherification of hydroxyl groups in 5-hydroxymethylfurfural over H4SiW12O40/MCM-41 nanospheres for liquid fuel production

Che, Penghua; Lu, Fang; Zhang, Junjie; Huang, Yanqun; Nie, Xin; Gao, Jin; Xu, Jie

doi:10.1016/j.biortech.2012.06.001

Cited by 112 publications

(74 citation statements)

References 15 publications

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“…[27] For this study, we selected unbranched alkyl alcohols (between C 8 and C 18 ) to obtain the corresponding 5-alkoxymethylfurfural derivatives. The reactions were performed at 100 8C by using a molar ratio HMF/alcohol = 1:1, and with an H-Beta zeolite catalyst with a Si/Al ratio of 13.…”

Section: Etherification With Fatty Alcohols With Different Number Of mentioning

confidence: 99%

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Biomass‐Derived Chemicals: Synthesis of Biodegradable Surfactant Ether Molecules from Hydroxymethylfurfural

et al. 2013

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A new class of biodegradable anionic surfactants with structures based on 5-alkoxymethylfuroate was prepared starting from 5-hydroxymethylfurfural (HMF), through a one-pot-two-steps process which involves the selective etherification of HMF with fatty alcohols using heterogeneous solid acid, followed by a highly selective oxidation of the formyl group with a gold catalyst. The etherification step was optimized using aluminosilicates as acid catalysts with different pore topologies (H-Beta, HY, Mordenite, ZSM-5, ITQ-2, and MCM-41), different active sites (Bronsted or Lewis) and different adsorption properties. It was shown that highly hydrophobic defect-free H-Beta zeolites with Si/Al ratios higher than 25 are excellent acid catalysts to perform the selective etherification of HMF with fatty alcohols, avoiding the competitive self-etherification of HMF. Moreover, the 5-alkoxymethylfurfural derivatives obtained can be selectively oxidized to the corresponding furoic salts in excellent yield using Au/CeO2 as catalyst and air as oxidant, at moderated temperatures. Both H-Beta zeolite and Au/CeO2 could be reused several times without loss of activity.

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Section: Etherification With Fatty Alcohols With Different Number Of mentioning

confidence: 99%

“…[18] In all cases, the reactions are performed using an excess of ethanol and temperatures ranging from 70 to 140 8C. In this work, we went one step further and performed a one-pot-two-steps reaction to produce a new type of surfactant.…”

Section: Introductionmentioning

confidence: 99%

Biomass‐Derived Chemicals: Synthesis of Biodegradable Surfactant Ether Molecules from Hydroxymethylfurfural

et al. 2013

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“…Furan derivatives obtained from renewable biomass resources have the potential to serve as substitutes for the petroleum-based building blocks that are currently used in the production of plastics and fine chemicals (N-Leshkov et al 2006). Among them, 5-hydroxymethylfurfural (HMF), an acid-catalyzed dehydration product of hexose, is one of the versatile platform chemicals playing an important role in the synthesis of biofuels and other valuable chemical intermediates such as aromatic hydrocarbons , 2, 5-dimethylfuran (DMF) (Saha et al 2014), and 5-ethoxymethylfurfural (EMF) (Che et al 2012).…”

Section: Introductionmentioning

confidence: 99%

Production of 5-Hydroxymethylfurfural from Fructose Catalyzed by Sulfonated Bamboo-Derived Carbon Prepared by Simultaneous Carbonization and Sulfonation

Shen

Chen

2016

BioResources

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A novel sulfonated bamboo-derived carbon (SBC) was prepared through a one-pot simultaneous carbonization and sulfonation method using ptoluenesulfonic acid as the sulfonating agent. This method was used in place of the two-step method of high temperature carbonization followed by sulfonation, in order to reduce energy consumption and avoid the use of substantial amounts of strong liquid acid. The as-prepared catalyst bearing SO3H, COOH, and phenolic OH groups demonstrated efficient catalytic activity in the dehydration of fructose to 5-hydroxymethylfurfural (HMF), achieving 92.1% HMF yield in a mixture of tetrahydrofuran (THF) and dimethylsulfoxiden (DMSO) (volume ratio of THF/DMSO 3/7). The mixture had a fructose concentration of 0.08 g·mL -1 with a catalyst amount of 10% weight of fructose at 140 °C in 60 min. No distinct activity drop was observed after the initial deactivation during 5 recycling runs, confirming a good stability of the prepared catalyst. Moreover, kinetic data showed that SBC promoted fructose dehydration to HMF may follow pseudo-first order kinetics with the activation energy of 43.6 kJ·mol -1 under investigated conditions. The convenient catalyst preparation method and excellent catalytic performance of the catalyst provide an easy-handling and ecofriendly strategy for crude biomass utilization in catalyst production.

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“…In particular, furans (e.g., 5-hydroxymethylfurfural HMF) are important biomass-derived molecules which can be used as starting materials for the synthesis of a variety of potentially useful compounds [15]. The structural moieties present in HMF, allow synthetic transformations to other target molecules by means of selective reactions such as: oxidation of the formyl group [16][17][18][19][20][21][22][23], reduction of the formyl group and/or the furan ring [24][25], deoxygenation of the hydroxyl groups to 2,5-dimethylfuran [26][27][28][29], etherification and carbonylation [30][31][32][33][34][35], and hydrogenolysis transformations [36][37]. In particular, selective reduction of 5-hydroxymethylfurfural (HMF) provides access to the diol 2,5-bishydroxymethylfuran (BHMF), a valuable building block for the production of polymers and polyurethane foams [18,38,39].…”

Section: Introductionmentioning

confidence: 99%

Oxidant free one-pot transformation of bio-based 2,5-bis-hydroxymethylfuran into α-6-hydroxy-6-methyl-4-enyl-2H-pyran-3-one in water

Gelmini

Albonetti

Cavani

et al. 2016

Applied Catalysis B: Environmental

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Catalytic selective etherification of hydroxyl groups in 5-hydroxymethylfurfural over H4SiW12O40/MCM-41 nanospheres for liquid fuel production

Cited by 112 publications

References 15 publications

Biomass‐Derived Chemicals: Synthesis of Biodegradable Surfactant Ether Molecules from Hydroxymethylfurfural

Biomass‐Derived Chemicals: Synthesis of Biodegradable Surfactant Ether Molecules from Hydroxymethylfurfural

Production of 5-Hydroxymethylfurfural from Fructose Catalyzed by Sulfonated Bamboo-Derived Carbon Prepared by Simultaneous Carbonization and Sulfonation

Oxidant free one-pot transformation of bio-based 2,5-bis-hydroxymethylfuran into α-6-hydroxy-6-methyl-4-enyl-2H-pyran-3-one in water

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