Reaction Rates for the Partial Dehydration of Glucose to Organic Acids in Solid‐Acid, Molecular‐Sieving Catalyst Powders

Lourvanij, Khavinet; Rorrer, Gregory L.

doi:10.1002/(sici)1097-4660(199705)69:1<35::aid-jctb685>3.3.co;2-0

Cited by 16 publications

(26 citation statements)

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“…The main product was formic acid, which indicates that secondary reactions consumed most of the formed HMF. Although consecutive reactions were observed, the formation of coke on the MCM catalysts was not as significant as on HY‐zeolite and aluminum‐pillared montmorillonite at 150 °C 51…”

Section: Heterogeneously Catalyzed Approachesmentioning

confidence: 93%

“…As for the reactions from pentoses to furfural, various zeolites, such as HY‐zeolite,33, 51, 52 mordenite,32 faujasite,52 and beta zeolite;52 aluminosilicates MCM‐20 and MCM‐41 with zeolitic structures;51 and pillared montmorillonite51, 53 have been evaluated for the production of HMF from hexoses. The Y‐zeolite was not suitable for HMF production since the yield was below 10 % 33.…”

Section: Heterogeneously Catalyzed Approachesmentioning

confidence: 99%

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Biorefining: Heterogeneously Catalyzed Reactions of Carbohydrates for the Production of Furfural and Hydroxymethylfurfural

2011

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Furfurals are important intermediates in the chemical industry. They are typically produced by homogeneous catalysis in aqueous solutions. However, heterogeneously catalyzed processes would be beneficial in view of the principles of green chemistry: the elimination of homogeneous mineral acids makes the reaction mixtures less corrosive, produces less waste, and facilitates easy separation and recovery of the catalyst. Finding an active and stable water-tolerant solid acid catalyst still poses a challenge for the production of furfural (furan-2-carbaldehyde) and 5-(hydroxymethyl)-2-furaldehyde (HMF). Furfural is produced in the dehydration of xylose, and HMF is formed from glucose and fructose in the presence of an acidic catalyst. Bases are not active in dehydration reaction but do catalyze the isomerization of monosaccharides, which is favorable when using glucose as a raw material. In addition to the desired dehydration of monosaccharides, many undesired side reactions take place, reducing the selectivity and deactivating the catalyst. In addition, the catalyst properties play an important role in the selectivity. In this Review, catalytic conversion approaches are summarized, focusing on the heterogeneously catalyzed formation of furfural. The attractiveness of catalytic concepts is evaluated, keeping in mind productivity, sustainability, and environmental footprint.

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Section: Heterogeneously Catalyzed Approachesmentioning

confidence: 93%

Section: Heterogeneously Catalyzed Approachesmentioning

confidence: 99%

Biorefining: Heterogeneously Catalyzed Reactions of Carbohydrates for the Production of Furfural and Hydroxymethylfurfural

2011

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“…Thus, Al‐SBA‐15 catalysts, with Si/Al molar ratios between 10 and 40, were tested in fructose dehydration achieving conversion values of 59‐68%, and HMF selectivities from 59 to 88% respectively, at 165 °C, in a biphasic H 2 O/MIBK (1:5 v/v) system, after 1 h reaction time . Partial dehydration of glucose to levulinic and formic acids using H‐Y zeolite, aluminium‐pillared montmorillonite, MCM‐20 and MCM‐41 was reported by Lourvanij and Rorrer, and yields lower than the theoretical ones were reached at 150°C …”

Section: Introductionmentioning

confidence: 90%

“…Usually, lower reaction temperatures are enough to attain high HMF yields from fructose, whereas higher values are needed starting from glucose. Moreover, in microporous materials, effective diffusivity of glucose can be reduced as observed in Y zeolite by Lourvanij and Rorrer …”

Section: Introductionmentioning

confidence: 99%

The Key Role of Textural Properties of Aluminosilicates in the Acid‐Catalysed Dehydration of Glucose into 5‐Hydroxymethylfurfural

et al. 2017

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Three protonated zeolites (H-ZSM-5, H-Y and H-Beta) were prepared and tested in the catalytic dehydration of glucose into 5-hydroxymethylfurfural (HMF). The catalytic results are compared with those obtained with a mesoporous MCM-41type aluminosilicate, in order to assess the influence of textural and acid properties on the catalytic performance. The dehydration process was carried out in a biphasic water/methylisobutyl ketone (MIBK) system, and the positive effect of NaCl addition (20 wt. %) on both HMF selectivity and yield was observed. Using the H-Beta zeolite in a NaCl aqueous solution/ MIBK, at 195 8C, the best catalytic results were obtained, with a HMF yield of 56%, close to that obtained with 10Al-MCM-41 (63%), after only 30 min of reaction time; whereas HMF yields rose only up to 42% using H-ZSM-5 and H-Y. This fact demonstrates the positive effect of mesoporosity to favour the dehydration of glucose to HMF. The reutilisation of these catalysts was also examined.[a] M.

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“…The importance of reactant dimensions relative to catalyst pore size was highlighted by Lourvanij et al, 8 who used glucose dehydration over Y zeolite. Several secondary reactions were identified, including isomerization of glucose to fructose, partial dehydration of glucose to 5-hydroxymethyl furfural (HMF), rehydration and cleavage of HMF to formic acid and 4-oxopentanoic acid, carbonization to form coke, or oligomerization of HMF.…”

Section: Introductionmentioning

confidence: 99%

Kinetics of Aqueous Phase Dehydration of Xylose into Furfural Catalyzed by ZSM-5 Zeolite

O’Neill

Ahmad

Vanoye

et al. 2009

Ind. Eng. Chem. Res.

170

107

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ZSM-5 zeolite in H + form with an average pore size of 1.2 nm was used for aqueous phase dehydration of xylose to furfural at low temperatures; that is, from 413 to 493 K. The selectivity in furfural increased with the temperature to a value of 473 K. Beyond this temperature, condensation reactions were significant and facilitated by the intrinsic structure of ZSM-5. A reaction mechanism that included isomerization of xylose to lyxose, dehydration of lyxose and xylose to furfural, fragmentation of furfural to organic acids, oligomerization of furfural to bi-and tridimensional furilic species, and complete dehydration of organic acids to carbonaceous deposits was developed, and the associated kinetic parameters were estimated. The rate of furfural production was found to be more sensitive to temperature than the rates of side reactions, with an estimated activation energy of 32.1 kcal/mol. This value correlated well with data in the literature obtained by homogeneous catalytic dehydration.

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Reaction Rates for the Partial Dehydration of Glucose to Organic Acids in Solid‐Acid, Molecular‐Sieving Catalyst Powders

Cited by 16 publications

References 0 publications

Biorefining: Heterogeneously Catalyzed Reactions of Carbohydrates for the Production of Furfural and Hydroxymethylfurfural

Biorefining: Heterogeneously Catalyzed Reactions of Carbohydrates for the Production of Furfural and Hydroxymethylfurfural

The Key Role of Textural Properties of Aluminosilicates in the Acid‐Catalysed Dehydration of Glucose into 5‐Hydroxymethylfurfural

Kinetics of Aqueous Phase Dehydration of Xylose into Furfural Catalyzed by ZSM-5 Zeolite

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