Synthesis of maleic and fumaric acids from furfural in the presence of betaine hydrochloride and hydrogen peroxide

Araji, Nahla; Madjinza, Désix Diane; Châtel, Grégory; Moores, Audrey; Jérôme, François; Vigier, Karine De Oliveira

doi:10.1039/c6gc02620f

Cited by 81 publications

(69 citation statements)

References 28 publications

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“…Compared with the biphasic Fa–H 2 O 2 −ethy acetate system in Li et al ., a much higher oxidation selectivity to maleic acid was achieved in the ChCl–Fa–SnCl 4 –H 2 O 2 system with no furanone and succinic acid. In addition, 20.8% of maleic acid along with 5.0% of fumaric acid based on the xylose content were observed, which were higher than those in the betaine hydrochloride–H 2 O 2 system …”

Section: Resultsmentioning

confidence: 99%

“…It was reported that γ‐valerolactone–H 2 O and betaine hydrochloride–H 2 O system have been shown to be excellent reaction media to produce furfural from hemicellulose, and they also performed well in oxidation of furfural to maleic acid with yields of about 70% and 60%, respectively. But there were no related results about direct conversion of xylose to maleic acid in γ‐valerolactone–H 2 O system, and only 17% maleic acid was recovered in the betaine hydrochloride–H 2 O system.…”

Section: Introductionmentioning

confidence: 99%

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A sustainable system for maleic acid synthesis from biomass‐derived sugar

Bai

Wang

et al. 2019

J of Chemical Tech & Biotech

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BACKGROUND: The preparation of maleic acid from the oxidation of renewable furfural has attracted significant attention, but research regarding the direct transformation of biomass-derived sugar to maleic acid is rare. The research regarding the direct transformation of xylose to maleic acid would further promote its industrial applications. RESULTS: The direct synthesis of maleic acid from xylose was investigated based on a sustainable system of deep eutectic solvents (DESs). Four DESs were screened to evaluate their abilities for the dehydration of xylose. Hydrogen peroxide (H 2 O 2 )was then loaded to realize the oxidation of furfural without the separation of intermediates. A good maleic acid yield of 20.8%, along with 5.0% of fumaric acid, based on the xylose content were obtained under the initial xylose loading of 50 mM, a tin(IV) chloride (SnCl 4 )-xylose molar ratio of 4:1, in a monophase choline chloride (ChCl)-formic acid (Fa) (molar ratio of 1:6) system at 120 ∘ C for 2 h. Then, 4 mL of H 2 O 2 per mmol furfural was loaded for a further 10 min at 120 ∘ C.CONCLUSION: This ChCl-Fa-SnCl 4 -H 2 O 2 system possesses a higher oxidation selectivity to maleic acid with no furanone and succinic acid. Moreover, it was interesting that ChCl and SnCl 4 could be recovered through natural recrystallization.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A sustainable system for maleic acid synthesis from biomass‐derived sugar

Bai

Wang

et al. 2019

J of Chemical Tech & Biotech

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“…Mostly, H 2 O 2 is used as an oxidizing agent for oxidation reactions such as the Baeyer–Villiger oxidation reaction, alcohol oxidation, phenol hydroxylation, sulfide oxidation, and cyclohexane oxidation . Hydrogen peroxide was recently employed successfully in biomass conversion, such as the production of gluconic acid from glucose, succinic acid from levulinic acid, and oxidation of furfural into maleic acid or fumaric acid . However, it is difficult to control the selectivity of reactions performed with H 2 O 2 , and it quickly decomposed in the presence of base or metal catalysts .…”

Section: Methodsmentioning

confidence: 99%

Hydrogen Peroxide Assisted Selective Oxidation of 5‐Hydroxymethylfurfural in Water under Mild Conditions

et al. 2017

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What was the biggest surprise?It would be the controllable selectivity to 5-formyl-2-furoic acid (FFCA) and2 ,5-furandicarboxylic acid (FDCA). Selectivity to the desired product is alwaysaproblem in the oxidation of 5-hydroxymethylfurfural (HMF), not only because HMF is easily converted to other chemicals, but also because there are several intermediate stages duringt he sequential oxidationp rocess. However,o wing to the different reactionr ates of each intermediate, we found that we are ablet oc ontrol the reaction product to be either FFCA or FDCA by simply adjusting the ratio between HMF and the catalyst.

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“…López-Granados et al has published several papers where using a commercial titanium silicate catalyst (TS-1), reaching a 70% of MAN yield with 5 wt % of the FF conversion in water, 5 wt % of the catalyst (titanium silicate), H 2 O 2 /FF mol ratio of 7.5, 50 • C and 24 h of residence time [74]. Recently, some other authors have also employed H 2 O 2 in the production of MAN [77][78][79]91,92]. However, in spite of the promising catalytic activity that offers the usage of H 2 O 2 , its usage could be restricted due to economic reasons [93].…”

Section: Anhydride Of Acids: Maleic Anhydride (Man)mentioning

confidence: 99%

Value-Added Bio-Chemicals Commodities from Catalytic Conversion of Biomass Derived Furan-Compounds

et al. 2020

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The depletion of fossil resources in the near future and the need to decrease greenhouse gas emissions lead to the investigation of using alternative renewable resources as raw materials. One of the most promising options is the conversion of lignocellulosic biomass (like forestry residues) into bioenergy, biofuels and biochemicals. Among these products, the production of intermediate biochemicals has become an important goal since the petrochemical industry needs to find sustainable alternatives. In this way, the chemical industry competitiveness could be improved as bioproducts have a great potential market. Thus, the main objective of this review is to describe the production processes under study (reaction conditions, type of catalysts, solvents, etc.) of some promising intermediate biochemicals, such as; alcohols (1,2,6-hexanetriol, 1,6-hexanetriol and pentanediols (1,2 and 1,5-pentanediol)), maleic anhydride and 5-alkoxymethylfuran. These compounds can be produced using 5-hydroxymethylfurfural and/or furfural, which they both are considered one of the main biomass derived building blocks.

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Synthesis of maleic and fumaric acids from furfural in the presence of betaine hydrochloride and hydrogen peroxide

Abstract: International audienc

Cited by 81 publications

References 28 publications

A sustainable system for maleic acid synthesis from biomass‐derived sugar

A sustainable system for maleic acid synthesis from biomass‐derived sugar

Hydrogen Peroxide Assisted Selective Oxidation of 5‐Hydroxymethylfurfural in Water under Mild Conditions

Value-Added Bio-Chemicals Commodities from Catalytic Conversion of Biomass Derived Furan-Compounds

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