Simultaneous Catalytic Conversion of C6 and C5 Sugars to Methyl Lactate in Near-critical Methanol with Metal Chlorides

Lu, Xiangnan; Fu, Jie; Langrish, T.A.G.; Lu, Xiuyang

doi:10.15376/biores.13.2.3627-3641

Cited by 10 publications

(34 citation statements)

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“…We also observed an MLA yield of 3.8% during the conversion of GADMA, which is unanticipated. As reported in previous studies, MLA was generally produced from the C3 intermediate products derived from the retro-aldol reaction of sugars. ,, We demonstrated that besides the C3 intermediate products the C2 side products were also capable of producing MLA. With water, GADMA could undergo a hydrolysis reaction to form GA .…”

Section: Resultssupporting

confidence: 79%

“…As shown in Figure b, different from the trend in the product yield of MLA, the GADMA and MAD yields decreased steadily with the increase of water content, which suggested easier hydrolysis of GADMA and MAD. GADMA originated from the C2 product via the retro-aldol reaction of sugars, and MAD was produced by the etherification of GADMA with methanol. , They are the two major side products from the conversion of sugars to MLA. When the water content was 0%, the GADMA and MAD yields were 10.4 and 21.1% for the conversion of glucose and xylose, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…Cellulose and hemicellulose make up 2 / 3 of lignocellulose . Cellulose and hemicellulose mainly consist of C5 and C6 sugars, which can be simultaneously converted to methyl lactate (MLA) resulting in high lignocellulose utilization rates . MLA can be used as a green solvent since it is biodegradable and possesses a high boiling point .…”

Section: Introductionmentioning

confidence: 99%

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Beneficial Effect of Water on the Catalytic Conversion of Sugars to Methyl Lactate in Near-Critical Methanol Solutions

Lyu

Chen

et al. 2019

Ind. Eng. Chem. Res.

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Biomass comprises a certain amount of water, which affects the reactions in organic solutions. Generally, water facilitates the hydrolysis of methyl lactate resulting in a decrease of the yield. However, we observed that a certain water content is beneficial for the production of methyl lactate on the conversion of sugars with NiO as a catalyst in near-critical methanol solutions. With water, glycolaldehyde dimethyl acetal, the main side product, was hydrolyzed to glycolaldehye. Glycolaldehye could be transformed to sugars via the aldol condensation at relative higher temperatures, and the sugars were subsequently converted to methyl lactate. NiO could be regenerated by calcination, and water showed almost no adverse effect on the activity of NiO catalyst. The beneficial effect of a certain water content showed a great potential for the direct production of methyl lactate from raw biomass materials without drying.

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Section: Resultssupporting

confidence: 79%

Section: Resultsmentioning

confidence: 99%

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Beneficial Effect of Water on the Catalytic Conversion of Sugars to Methyl Lactate in Near-Critical Methanol Solutions

Lyu

Chen

et al. 2019

Ind. Eng. Chem. Res.

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“…This approach can be successfully extended to cellulose (73% C yield). Further proof of this strategy is encountered in the work by Li et al, which focused on the conversion of hexoses (from cellulose) and pentoses (from hemicellulose) to methyl lactate (MeLac) in near-supercritical methanol and in the presence of several metal chloride catalysts [86]. In the case of glucose, the best yield to MLA (47%) is obtained with LaCl 3 , a catalyst that also renders good MLA yields from fructose (64%) and xylose (33%).…”

Section: Direct Reactions Of Xylose To Alcohols Acids and Polymersmentioning

confidence: 99%

Catalytic Processes from Biomass-Derived Hexoses and Pentoses: A Recent Literature Overview

2018

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Biomass is a plentiful renewable source of energy, food, feed and chemicals. It fixes about 1–2% of the solar energy received by the Earth through photosynthesis in both terrestrial and aquatic plants like macro- and microalgae. As fossil resources deplete, biomass appears a good complement and eventually a good substitute feedstock, but still needs the development of relatively new catalytic processes. For this purpose, catalytic transformations, whether alone or combined with thermal ones and separation operations, have been under study in recent years. Catalytic biorefineries are based on dehydration-hydrations, hydrogenations, oxidations, epimerizations, isomerizations, aldol condensations and other reactions to obtain a plethora of chemicals, including alcohols, ketones, furans and acids, as well as materials such as polycarbonates. Nevertheless, there is still a need for higher selectivity, stability, and regenerability of catalysts and of process intensification by a wise combination of operations, either in-series or combined (one-pot), to reach economic feasibility. Here we present a literature survey of the latest developments for obtaining value-added products using hexoses and pentoses derived from lignocellulosic material, as well as algae as a source of carbohydrates for subsequent transformations.

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“…The generation of as malla mount of MLE (4.9 %y ield) could be ascribed to the weak transfer hydrogenation activity of FALi nm ethanol over Hb.T he major intermediates were FALa nd b-methoxy-2-furanethanol (MFE). [4] In the absence of any catalyst, methyl b-d-xylopyranoside( MDX, Scheme 2) was the major product, which indicates that hydrolysis of xylose and MDX does not proceed easily withoutt he acid catalysts. [6a] The total carbonb alance was quite low,w hich could be attributed to the formation of humins from the polymerization of FALa nd xylose.…”

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Simultaneous Conversion of C₅ and C₆ Sugars into Methyl Levulinate with the Addition of 1,3,5‐Trioxane

et al. 2019

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The simultaneous conversion of C 5 andC 6 mixed sugarsi nto methyl levulinate (MLE) has emerged as av ersatile strategy to eliminate costly separation steps. However,t he traditional upgradingo fC 5 sugars into MLE is very complex as it requires both acid-catalyzed and hydrogenation processes. This study concerns the development of ao ne-pot,h ydrogenation-free conversion of C 5 sugarsi nto MLE over different acid catalysts at near-critical methanolconditions with the help of 1,3,5-trioxane. For the conversion of C 5 sugars over zeolites without the addition of 1,3,5-trioxane, the MLE yield is quite low,o wing to low hydrogenation activity.T he addition of 1,3,5-trioxanes ignificantly boosts the MLE yield by providing an alternative conversion pathway that does not include the hydrogenation step. Ad irectc omparison of the catalytic performance of five differentz eolitesr eveals that Hb zeolite,w hichh as high densities of both Lewis and Brønsted acid sites, affords the highest MLE yield. With the addition of 1,3,5-trioxane, the hydroxymethylation of furfural derivativea nd formaldehyde is ak ey step. Notably,t he simultaneous conversion of C 5 and C 6 sugars catalyzed by Hb zeolite can attain an MLE yield as high as 50.4 %w hen the reaction conditions are fully optimized. Moreover,t he Hb zeolite catalystc an be reused at least five times withoutsignificant change in performance.Lignocellulosic biomass,a st he mosta bundant carbon-containing organic resource, can be depolymerized and hydrolyzed into C 5 and C 6 sugars. [1] These mixed sugars are difficult to separate, owing to their many similarities and lack of fixed boiling points. [2] An efficient approach is to convert them into volatile chemicals, such as C 5 -derived furfural (FAL) and C 6 -derived 5-(hydroxymethyl)furfural (HMF). [3] However,t he resultant prod-ucts of these conversion processes are usually different, leading to the occurrenceo fs ome costly separation processes. [1a] To avoid this situation, the simultaneous conversion of C 5 and C 6 sugars into the same platform chemical by furtherc onverting FALa nd HMFr epresents ap romising solution. [3e, 4] Brønsted acid (B acid) sites have been identified as the main active site for the production of FALa nd HMF from the hydrolysis of sugars;H MF can be easily converted into methyll evulinate (MLE). [5] The traditional upgrading of hemicellulose-derived C 5 sugars to MLE is very complex. [3e] This multistep conversion includes the hydrogenation of FALinto furfuryl alcohol (FOL) in addition to acid-catalyzed alcoholysis (Scheme 1, blue arrows). [6] The hydrogenation process, in particular,r equires high-pressure H 2 , hydrogenation-active sites, and other harsh reaction conditions that hinder the effectiveness of the conversion. [7] Established one-pot productions trategiesf or the conversion of C 5 sugars into MLE have shown only limited success. Hu et al.,f or example, reported ao ne-pot synthesis of MLE from xylose at 7MPa H 2 pressure over Amberlyst 70 (acid) and Pd/Al 2 O 3 (hydrogenat...

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Simultaneous Catalytic Conversion of C6 and C5 Sugars to Methyl Lactate in Near-critical Methanol with Metal Chlorides

Cited by 10 publications

References 0 publications

Beneficial Effect of Water on the Catalytic Conversion of Sugars to Methyl Lactate in Near-Critical Methanol Solutions

Beneficial Effect of Water on the Catalytic Conversion of Sugars to Methyl Lactate in Near-Critical Methanol Solutions

Catalytic Processes from Biomass-Derived Hexoses and Pentoses: A Recent Literature Overview

Simultaneous Conversion of C₅ and C₆ Sugars into Methyl Levulinate with the Addition of 1,3,5‐Trioxane

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Simultaneous Catalytic Conversion of C6 and C5 Sugars to Methyl Lactate in Near-critical Methanol with Metal Chlorides

Cited by 10 publications

References 0 publications

Beneficial Effect of Water on the Catalytic Conversion of Sugars to Methyl Lactate in Near-Critical Methanol Solutions

Beneficial Effect of Water on the Catalytic Conversion of Sugars to Methyl Lactate in Near-Critical Methanol Solutions

Catalytic Processes from Biomass-Derived Hexoses and Pentoses: A Recent Literature Overview

Simultaneous Conversion of C5 and C6 Sugars into Methyl Levulinate with the Addition of 1,3,5‐Trioxane

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Simultaneous Conversion of C₅ and C₆ Sugars into Methyl Levulinate with the Addition of 1,3,5‐Trioxane