Study on the Isomerization of Maleic Acid to Fumaric Acid without Catalyst

Gao, Zhuo; Chen, Wangmi; Rothenberg, Marc E.; Wang, Dali; Shou-zhi, YI

doi:10.1002/bkcs.11499

Cited by 21 publications

(18 citation statements)

References 27 publications

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“…3, vanillic acid is firstly oxidised to oand p-quinones, which react with free radicals to produce ring-opening reactions, obtaining maleic acid. Maleic acid is isomerised to fumaric acid if heated at 120 • C in aqueous solution (Whelan, 1994), producing malic acid at higher temperatures (Gao et al, 2018). This observation indicates that during the transition of maleic to fumaric acid, the double bond is more labile to be hydroxylated, explaining why at higher temperatures malic and tartaric acids were present at higher amounts, especially after several minutes of reaction.…”

Section: Effect Of Reaction Time In C 4 -Dca Production Under Alkalinmentioning

confidence: 99%

Catalytic wet peroxide oxidation of vanillic acid as a lignin model compound towards the renewable production of dicarboxylic acids

Vega-Aguilar

Barreiro

Rodrigues

2020

Chemical Engineering Research and Design

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Lignin can be depolymerised and used as a feedstock to obtain renewable raw-materials, providing a green alternative to fossil counterparts. Among others, C 4 dicarboxylic acids (DCA), like succinic, malic, maleic and fumaric acids, which can find applications in pharmaceuticals, food industry, and act as solvents, can be obtained from lignin oxidation. To investigate their formation, the oxidation of vanillic acid (VA), a lignin model compound, was studied under catalytic wet peroxide oxidation (CWPO) conditions, using titanium silicalite-1 (TS-1) as the catalyst. The effect of temperature, pH, and reaction time were studied. In a second phase, catalyst modification with transition metal oxides (Fe, Co, Cu) was tested. Results showed that oxidation under pH = 10.5 gives rise to complete VA conversion with hydroxylated DCA, namely malic (15 mol%) and tartaric (5 mol%) acids, as the main products. At pH = 4.0, the production of succinic acid was improved (7.4 mol%), with VA conversion achieving 78% after 2.0 h of reaction. At alkaline pH, H 2 O 2 reactivity is higher, leading to C 4-DCA degradation to low-molecular weight compounds. Catalyst desilication was observed, pointed out for the convenience of using neutral and acidic pH. In acidic pH, Fe and Cu catalysts enhanced VA conversion, and Fe catalyst was more selective towards succinic acid production.

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Section: Effect Of Reaction Time In C 4 -Dca Production Under Alkalinmentioning

confidence: 99%

Catalytic wet peroxide oxidation of vanillic acid as a lignin model compound towards the renewable production of dicarboxylic acids

Vega-Aguilar

Barreiro

Rodrigues

2020

Chemical Engineering Research and Design

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“…However, the catalysts exhibited significantly different MA conversion and SA selectivity owing to the difference in the properties of the Al 2 O 3 support. It has been reported that the isomerization of MA to FA can occur without a catalyst and is strongly affected by the concentration of maleic acid, the reaction temperature, and the pH of the solution [15]. Al 2 O 3 in the Pd/Al 2 O 3 (900)_pH11.5 catalyst was in the γ phase, which has a large specific surface area and strong acid sites, whereas in the Pd/Al 2 O 3 (1100)_pH7.5 catalyst, it was in the θ + α phase, which has a small specific surface area and weak acid sites.…”

Section: Effect Of Al 2 O 3 Support Properties and Pd Dispersionmentioning

confidence: 99%

Liquid-Phase Hydrogenation of Maleic Acid over Pd/Al2O3 Catalysts Prepared via Deposition–Precipitation Method

et al. 2019

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Succinic acid (SA) is a valuable raw material obtained by hydrogenation of maleic acid (MA). The product selectivity of this reaction is highly dependent on the reaction conditions. This study therefore investigated the effect of the reaction temperature, hydrogen pressure, and reaction time on the liquid-phase hydrogenation of MA by a Pd/Al2O3 catalyst. Complete conversion of MA and 100% selectivity for SA were achieved at a temperature of 90 °C, H2 pressure of 5 bar, and reaction time of 90 min. Fumaric acid (FA) was formed as an intermediate material by hydrogenation of MA under nonoptimal conditions. The impact of the percentage of Pd dispersion and phase of the Al2O3 support (γ, θ + α, and α) was also examined. The Pd/Al2O3 catalyst with 29.8% dispersion of Pd and γ phase of Al2O3 exhibited the best catalytic performance. Thus, catalytic activity depends not only on the amount of Pd dispersion but also on the physicochemical properties of Al2O3.

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“…Organic acids are produced industrially by either fermentation or chemical synthesis (Pinazo et al 2015). The main advantage of synthesis is that the resulting product is usually of high purity and concentrated (Ai and Ohdan 1997;Gao et al 2018). But the high energy demand and the use of expensive catalysts (Sang et al 2019), in some cases toxic, environmentally hazardous reagents (Prikaznov et al 2011;Solmi et al 2019), represent great shortcomings of synthetic methods.…”

Section: Introductionmentioning

confidence: 99%

Low-waste fermentation-derived organic acid production by bipolar membrane electrodialysis—an overview

2021

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Organic acids, e.g, citric acid, fumaric acid, lactic acid, malic acid, pyruvic acid and succinic acid, have important role in the food industry and are potential raw materials for the sustainable chemical industry. Their fermentative production based on renewable raw materials requires innovatively designed downstream processing to maintain low environmental impact and resource efficiency throughout the production process. The application of bipolar membranes offers clean and effective way to generate hydrogen ions required for free acid production from its salt. The water dissociation reaction inside the bipolar membrane triggered by electric field plays key role in providing hydrogen ion for the replacement of the cations in organic acid salts. Combined with monopolar ion-exchange membranes in a bipolar membrane electrodialysis process, material flow can be separated beside the product stream into additional reusable streams, thus minimizing the waste generation. This paper focuses on bipolar membrane electrodialysis applied for organic acid recovery from fermentation broth.

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Study on the Isomerization of Maleic Acid to Fumaric Acid without Catalyst

Cited by 21 publications

References 27 publications

Catalytic wet peroxide oxidation of vanillic acid as a lignin model compound towards the renewable production of dicarboxylic acids

Catalytic wet peroxide oxidation of vanillic acid as a lignin model compound towards the renewable production of dicarboxylic acids

Liquid-Phase Hydrogenation of Maleic Acid over Pd/Al2O3 Catalysts Prepared via Deposition–Precipitation Method

Low-waste fermentation-derived organic acid production by bipolar membrane electrodialysis—an overview

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