Efficient catalytic system for the conversion of fructose into 5-ethoxymethylfurfural

Wang, Hongliang; Deng, Tiansheng; Wang, Yingxiong; Qi, Yongqin; Hou, Xun; Zhu, Yulei

doi:10.1016/j.biortech.2013.02.110

Cited by 122 publications

(90 citation statements)

References 27 publications

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“…The effect of DMSO on the reaction was studied, and the results were similar to the ones reported for the production of other 5-HMF derivatives in DMSO (Figure 2) [22]. The addition of DMSO did not necessarily affect the conversion of fructose but instead changed the distribution of the products, leading to the production of 5-HMF.…”

Section: Production Of Hdmf In a Dmso/methanol Biphasic Systemsupporting

confidence: 78%

“…It has been Catalysts 2017, 7, 237 6 of 14 reported that fructose dehydration using DMSO could be promoted at temperatures above 140 • C [23], which also promoted the reactions to form DMMF and MMF. Figure 3 depicts a typical behavior of a consecutive reaction system, showing that the maximum HDMF concentration was reached at 150 • C. Upon further increasing the temperature, both the etherification of the dimethyl acetal of 5-HMF and the formation of humins were facilitated [22].…”

Section: Production Of Hdmf In a Dmso/methanol Biphasic Systemmentioning

confidence: 99%

“…Figure 3 depicts a typical behavior of a consecutive reaction system, showing that the maximum HDMF concentration was reached at 150 °C. Upon further increasing the temperature, both the etherification of the dimethyl acetal of 5-HMF and the formation of humins were facilitated [22].…”

Section: Production Of Hdmf In a Dmso/methanol Biphasic Systemmentioning

confidence: 99%

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Facile, One-Pot, Two-Step, Strategy for the Production of Potential Bio-Diesel Candidates from Fructose

et al. 2017

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Abstract:The production of bio-diesel fuels from carbohydrates is a promising alternative to fossil fuels with regard to the growing severity of the environmental problem and energy crisis. Potential bio-diesel candidates or additives, such as 5-(hydroxymethyl)-2-(dimethoxymethyl) furan (HDMF), 2-(dimethoxymethyl)-5-(methoxymethyl) furan (DMMF), and 5-(methoxymethyl)-2-furaldehyde (MMF) could be produced from the alcoholic solutions of both 5-HMF and fructose in the presence of solid acid catalysts. In the present study, a readily prepared, silica, gel-supported nitric acid (SiO 2 -HNO 3 ) catalyst was found to be exceptionally reactive for the production of HDMF from fructose. A DMSO-methanol biphasic solvent system was developed and HDMF, DMMF, and MMF were observed at 150 • C, with maximum yields of 34%, 34%, and 25%, respectively. Meanwhile, a maximum HDMF yield of 77% was obtained from 5-HMF in methanol. Moreover, a sequential, one-pot, two-step dehydration/acetalization process, involving the dehydration of fructose to 5-HMF in dimethylsulfoxide (DMSO) at 150 • C, and followed by adding a certain amount of methanol to react with the formed 5-HMF to HDMF at 100 • C, was developed to promote the yield of HDMF. The optimum yield of HDMF reached 70% with the complete conversion of fructose. The reaction mechanisms of dehydration and acetalization have been proposed for the conversion of 5-HMF to HDMF. The two-step design allows for facile catalyst recycling while supplying as a promising method for the production of biodiesel from complex carbohydrates.

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Section: Production Of Hdmf In a Dmso/methanol Biphasic Systemsupporting

confidence: 78%

Section: Production Of Hdmf In a Dmso/methanol Biphasic Systemmentioning

confidence: 99%

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Facile, One-Pot, Two-Step, Strategy for the Production of Potential Bio-Diesel Candidates from Fructose

et al. 2017

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“…Due to its ease of separation from reaction mixture and reusability, much effort using heterogeneous catalyst has been taken to achieve the goal. For example, heteropolyacid [7,8] or its supported nanoparticles [9][10][11][12][13], acid-modified silica mesoporous materials [14,15], graphene oxide [16], and magnetic solid acid catalysts [11,17,18] were found to be efficient in the synthesis of EMF from fructose or fructose-based carbohydrates. By contrast, the transformation of glucose to EMF is much difficult owing to the demand of isomerization into fructose firstly, and the above developed catalysts had low reactivity.…”

Section: Introductionmentioning

confidence: 99%

Insights into the Metal Salt Catalyzed 5-Ethoxymethylfurfural Synthesis from Carbohydrates

Gao

Tao

et al. 2017

Catalysts

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Abstract:The use of common metal salts as catalysts for 5-ethoxymethylfurfural (EMF) synthesis from carbohydrate transformation was performed. Initial screening suggested AlCl 3 as an efficient catalyst for EMF synthesis (45.0%) from fructose at 140 • C. Interestingly, CuSO 4 and Fe 2 (SO 4 ) 3 were found to yield comparable EMF at lower temperature of 110 to 120 • C, and high yields of ethyl levulinate (65.4-71.8%) were obtained at 150 • C. However, these sulfate salts were inactive in EMF synthesis from glucose and the major product was ethyl glucoside with around 80% yield, whereas EMF of 15.2% yield could be produced from glucose using CrCl 3 . The conversion of sucrose followed the accumulation of the reaction pathways of fructose and glucose, and a moderate yield of EMF could be achieved.

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“…The use of HPAs for the production of HMF has been previously reported. [17,18,19]. The reaction mechanism proposed to hydrolysis of cellulose using HPAs is the same as using mineral acids, starting with protonation of glycosidic oxygen and cleavage of C1-O linkage.…”

Section: Introdutionmentioning

confidence: 99%

Hydrolysis of cellulose using heteropoly salts derivatives from H3PW12O40 with different redox properties as catalysts

et al. 2017

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Heteropoly salts containing different numbers of vanadium atoms (K 4 [PVW 11 O 40 (HPW), and used as catalysts in hydrolysis of cellulose reactions in order to change the redox properties and verify whether the cluster of catalysts are involved in mechanism reaction. The hydrolysis reactions following a full 23 factorial design with the variables: mass ratio (catalyst/substrate), reaction time and temperature. The variables evaluated were significant at a 90% confidence level including second and third order interactions. According to the conducted experiments, the catalysts were all active in hydrolysis. The best results occurred when HPW was used suggesting that the redox properties did not have much influence in depolymerization of cellulose and the hydrolysis mechanism are assigned to acidic properties of the medium. The main products obtained from the reactions were glucose and HMF, which are products of great interest in the chemical industry.

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Efficient catalytic system for the conversion of fructose into 5-ethoxymethylfurfural

Cited by 122 publications

References 27 publications

Facile, One-Pot, Two-Step, Strategy for the Production of Potential Bio-Diesel Candidates from Fructose

Facile, One-Pot, Two-Step, Strategy for the Production of Potential Bio-Diesel Candidates from Fructose

Insights into the Metal Salt Catalyzed 5-Ethoxymethylfurfural Synthesis from Carbohydrates

Hydrolysis of cellulose using heteropoly salts derivatives from H3PW12O40 with different redox properties as catalysts

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