Aluminum‐based Metal‐Organic Framework as Water‐tolerant Lewis Acid Catalyst for Selective Dihydroxyacetone Isomerization to Lactic Acid

Rahaman, Mohammad Shahinur; Tulaphol, Sarttrawut; Mills, Kyle; Molley, Ashten; Hossain, Md. Anwar; Lalvani, Shashi B.; Maihom, Thana; Crocker, Mark; Sathitsuksanoh, Noppadon

doi:10.1002/cctc.202101756

Cited by 6 publications

(4 citation statements)

References 83 publications

(95 reference statements)

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“…Our findings offer a new understanding of how amino groups increase Lewis acid strength, and the findings could guide the development of reusable selective catalysts for glucose isomerization. Moreover, this new understanding is expected to extend to other Lewis acid‐catalyzed organic reactions, [84] such as Diels‐Alder, [85] Meerwein‐Ponndorf‐Verley, [86–87] oxidation, [62] Friedel‐Crafts, [88–89] hydration, [90] and production of 5‐hydroxymethylfurfural from cellulose [10] …”

Section: Discussionmentioning

confidence: 99%

Aluminum‐Containing Metal‐Organic Frameworks as Selective and Reusable Catalysts for Glucose Isomerization to Fructose

et al. 2022

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Fructose is a versatile precursor for food and chemicals. Currently, catalytic production of fructose is achieved by enzymatic isomerization of glucose from renewable lignocellulose. Although the catalyst, glucose isomerase, is selective, it is not stable. Here, aluminum‐containing metal‐organic frameworks (Al‐MOFs) are shown to be active, selective, stable, and reusable for glucose isomerization in ethanol. Al‐MOFs achieved 64% fructose selectivity with 82% glucose conversion at 120 °C, superior performance compared with most other solid catalysts. The amino groups in Al‐MOFs enhance Lewis acid strength, which is responsible for the high fructose selectivity at high glucose conversion. Moreover, the Al‐MOF catalyst is stable and reusable at least four times without losing either activity or fructose selectivity. These findings illustrate compelling opportunities for Al‐MOFs in fructose production and other organic reactions, such as fructose conversion to 5‐hydroxymethylfurfural and levulinic acid.

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Section: Discussionmentioning

confidence: 99%

Aluminum‐Containing Metal‐Organic Frameworks as Selective and Reusable Catalysts for Glucose Isomerization to Fructose

et al. 2022

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“…Since the conversion of MGO to LA has been known for a long time [ 127 ], the limiting step in this process was the conversion of DHA to MGO, as shown by several studies on the kinetic parameters of this reaction [ 119 , 120 , 121 , 128 ]. This synthesis route is currently a trend of interest for several research teams, as interesting results have been obtained using highly efficient and recyclable Lewis-acid catalysts [ 118 , 119 , 120 , 121 , 128 , 129 , 130 , 131 , 132 , 133 , 134 , 135 ].…”

Section: A Multi-functional Synthesis Tool: Dha’s Broad Range Of Reac...mentioning

confidence: 99%

Dihydroxyacetone: A User Guide for a Challenging Bio-Based Synthon

et al. 2023

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1,3-dihydroxyacetone (DHA) is an underrated bio-based synthon, with a broad range of reactivities. It is produced for the revalorization of glycerol, a major side-product of the growing biodiesel industry. The overwhelming majority of DHA produced worldwide is intended for application as a self-tanning agent in cosmetic formulations. This review provides an overview of the discovery, physical and chemical properties of DHA, and of its industrial production routes from glycerol. Microbial fermentation is the only industrial-scaled route but advances in electrooxidation and aerobic oxidation are also reported. This review focuses on the plurality of reactivities of DHA to help chemists interested in bio-based building blocks see the potential of DHA for this application. The handling of DHA is delicate as it can undergo dimerization as well as isomerization reactions in aqueous solutions at room temperature. DHA can also be involved in further side-reactions, yielding original side-products, as well as compounds of interest. If this peculiar reactivity was harnessed, DHA could help address current sustainability challenges encountered in the synthesis of speciality polymers, ranging from biocompatible polymers to innovative polymers with cutting-edge properties and improved biodegradability.

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“…The technical lignin and lignin hydrogenolysis products were characterized by elemental analysis (CHONS), [95][96][97] Nuclear Magnetic Resonance (NMR), [98][99] and Size Exclusion Chromatography (SEC) [98][99][100] (see Supporting Information for detail).…”

Section: Reaction Product Identification and Quantificationmentioning

confidence: 99%

Catalytic Hydrogenolysis of Lignin into Phenolics by Internal Hydrogen over Ru Catalyst

et al. 2022

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Lignin is a by-product of biorefineries and pulp and paper manufacturers. Lignin is a renewable source of phenolic precursors for fuels and chemicals. Hydrogenolysis of lignin cleaves the abundant β-O-4 bonds and releases phenolics. However, selective hydrogenolysis of lignin's β-O-4 bonds is challenging because it requires high-pressure H 2 . Here we show efficient hydrogenolysis of lignin model compounds and technical lignin by Ru/C catalyst and internal hydrogen. The aliphatic hydroxyl groups (C α À OH) in lignin enabled Ru-catalyzed dehydrogenation of internal hydrogen and the formation of reactive keto intermediate, which facilitated the β-O-4 cleavage into phenolic monomers. Furthermore, solvents that had a high donor number (Lewis basicity) enhanced the yield of phenolic monomers, equal to 27.9 wt.% from technical lignin. These findings offer a novel approach for biorefineries to design lignin isolation processes and/or solvent systems to maximize phenolic monomers and to control product selectivity/stability.

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Aluminum‐based Metal‐Organic Framework as Water‐tolerant Lewis Acid Catalyst for Selective Dihydroxyacetone Isomerization to Lactic Acid

Cited by 6 publications

References 83 publications

Aluminum‐Containing Metal‐Organic Frameworks as Selective and Reusable Catalysts for Glucose Isomerization to Fructose

Aluminum‐Containing Metal‐Organic Frameworks as Selective and Reusable Catalysts for Glucose Isomerization to Fructose

Dihydroxyacetone: A User Guide for a Challenging Bio-Based Synthon

Catalytic Hydrogenolysis of Lignin into Phenolics by Internal Hydrogen over Ru Catalyst

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