Reactivity of levulinic acid during aqueous, acid-catalyzed HMF hydration

Karwa, Shruti; Gajiwala, Varun Mitesh; Heltzel, Jacob; Patil, Sushil K. R.; Lund, C.R.F.

doi:10.1016/j.cattod.2015.06.020

Cited by 26 publications

(18 citation statements)

References 19 publications

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“…Although other researchers had already reported this transformation, this approach seems to be one of the most convenient ones to obtain the product in high yields. Recently, Lund's group has confirmed that this transformation occurs through the formation of 5‐hydroxy‐γ‐valerolactone, the so‐called pseudolevulinic acid, as an intermediate …”

Section: Properties Biological Applications and Preparation Of Angementioning

confidence: 99%

“…Recently,L und's group has confirmed that this transformation occurs through the formation of 5-hydroxy-gvalerolactone,t he so-called pseudolevulinic acid, as an intermediate. [18] In the last few years, however,t he growing applications of levulinica cid have instigated the search for greener approachesn ot only for its production from biomass feedstocks but also fori ts upgrading. [6] In this sense, considerable efforts have been devoted to the developmento fr ecoverable solid acid catalysts for the conversion of LA into a-AL.…”

Section: Preparation Of A-angelica Lactonementioning

confidence: 99%

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Angelica Lactones: From Biomass‐Derived Platform Chemicals to Value‐Added Products

et al. 2017

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The upgrading of biomass‐derived compounds has arisen in recent years as a very promising research field in both academia and industry. In this sense, a lot of new processes and products have been developed, often involving levulinic acid as a starting material or intermediate. In the last few years, though, other scaffolds have been receiving growing attention, especially, angelica lactones. Considering these facts and the emergent applications of said molecules, in this review we will discuss their preparation and applications; the use of these frameworks as starting materials in organic synthesis to produce potential bioactive compounds will be covered, as will their use as a foundation to highly regarded compounds such as liquid alkanes with prospective use as fuels and polymers.

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Section: Properties Biological Applications and Preparation Of Angementioning

confidence: 99%

Section: Preparation Of A-angelica Lactonementioning

confidence: 99%

Angelica Lactones: From Biomass‐Derived Platform Chemicals to Value‐Added Products

et al. 2017

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“…In the presence of acid catalysts, under heating, α-angelica lactone can isomerize, thus forming a mixture containing also β-angelica lactone (3-penten-4-olide) and γ-angelica lactone (4-penten-4-olide). Besides, the angelica lactones can also dimerize giving heavier by-products [70].…”

Section: Homogeneous Mineral Acids and Salts In Watermentioning

confidence: 99%

New Frontiers in the Catalytic Synthesis of Levulinic Acid: From Sugars to Raw and Waste Biomass as Starting Feedstock

et al. 2016

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Levulinic acid (LA) is one of the top bio-based platform molecules that can be converted into many valuable chemicals. It can be produced by acid catalysis from renewable resources, such as sugars, lignocellulosic biomass and waste materials, attractive candidates due to their abundance and environmentally benign nature. The LA transition from niche product to mass-produced chemical, however, requires its production from sustainable biomass feedstocks at low costs, adopting environment-friendly techniques. This review is an up-to-date discussion of the literature on the several catalytic systems that have been developed to produce LA from the different substrates. Special attention has been paid to the recent advancements on starting materials, moving from simple sugars to raw and waste biomasses. This aspect is of paramount importance from a sustainability point of view, transforming wastes needing to be disposed into starting materials for value-added products. This review also discusses the strategies to exploit the solid residues always obtained in the LA production processes, in order to attain a circular economy approach.

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“…However, this ratio could be greater than, equal to or less than 1 : 1 in experiments under different conditions. 35 For instance, Asghari et al found that when catalyzed by hydrochloric acid, FA could decompose faster than LA aer they were generated from HMF rehydration, leading to a much higher yield of LA than that of FA. 36 However, when the organic solvent DMOE was gradually added into the solution until the DMOEwater ratio reached 7 : 1, the yield of LA and FA showed a steep drop while the yield of HMF rose rapidly to 48.27%.…”

Section: Effect Of Solvent Compositionmentioning

confidence: 99%

Influence of a Lewis acid and a Brønsted acid on the conversion of microcrystalline cellulose into 5-hydroxymethylfurfural in a single-phase reaction system of water and 1,2-dimethoxyethane

et al. 2018

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-Hydroxymethylfurfural (HMF) is a typical dehydration product of C6 carbohydrates, and it can be converted into a series of chemicals and liquid fuels. In this study, an advanced low-boiling single-phase reaction system consisting of water and 1,2-dimethoxyethane (DMOE) was proposed for the production of HMF from microcrystalline cellulose (MCC). AlCl 3 and H 3 PO 4 were selected as the Lewis acidic catalyst and Brønsted acidic catalyst, respectively, and the influence of these two catalysts on the conversion behavior of MCC was studied. The results showed that MCC could be selectively converted into HMF or levulinic acid (LA) by altering the solvent composition. As for the composition of the catalyst, high AlCl 3 content favored the generation of HMF, whereas high H 3 PO 4 content could decrease the HMF yield and promote the formation of glucose and fructose. The highest HMF yield of 49.42% was obtained at an AlCl 3 -H 3 PO 4 ratio of 1 : 0.8. GC-MS analysis suggested that much MCC was transformed into furans and cyclopentenones in the presence of AlCl 3 , while anhydrosugars tended to be generated with a high H 3 PO 4 proportion in the catalyst. Besides, FTIR analysis of the insoluble humin formed during MCC conversion indicated that AlCl 3 could also facilitate the depolymerization of MCC.

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Reactivity of levulinic acid during aqueous, acid-catalyzed HMF hydration

Cited by 26 publications

References 19 publications

Angelica Lactones: From Biomass‐Derived Platform Chemicals to Value‐Added Products

Angelica Lactones: From Biomass‐Derived Platform Chemicals to Value‐Added Products

New Frontiers in the Catalytic Synthesis of Levulinic Acid: From Sugars to Raw and Waste Biomass as Starting Feedstock

Influence of a Lewis acid and a Brønsted acid on the conversion of microcrystalline cellulose into 5-hydroxymethylfurfural in a single-phase reaction system of water and 1,2-dimethoxyethane

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