Low-temperature oxidation of guaiacol to maleic acid over TS-1 catalyst in alkaline aqueous H2O2 solutions

Su, Junfeng; Yang, Lisha; Liu, Reed Nicholas; Lin, Hongfei

doi:10.1016/s1872-2067(14)60039-5

Cited by 17 publications

(10 citation statements)

References 119 publications

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“…Also, the high nucleophilic capacity of H 2 O 2 at alkaline pH causes the hydroxylation of double bonds, in both maleic and fumaric acids, leading to the formation of malic and tartaric acids, but avoiding the production of succinic acid at higher yields. In this work, succinic acid was identified (up to 5.6 mol%), while Su et al (2014) that reported guaiacol alkaline peroxide oxidation with TS-1 at 80 • C shown no production of succinic acid, but higher maleic acid yield (up to 27.7 mol%). Looking to achieve high yields for succinic acid, as according to step c) in Fig.…”

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

confidence: 56%

“…The product selectivity depends on the oxidising agent, catalyst type, process conditions and reactor type (Kang et al, 2013;Ma et al, 2015). In the context of DCA from lignin, several studies have been carried out using wet peroxide oxidation, with and without catalyst (Cronin et al, 2017;Hasegawa et al, 2011;Kang et al, 2019;Ma et al, 2015;Su et al, 2014;Yin et al, 2015;Zeng et al, 2015). However, many of the lignin oxidation processes, including the catalysed ones, are not selective enough to favour the production of a specific DCA, generating a mixture of DCA, introducing the need of additional steps of separation and purification.…”

Section: Introductionmentioning

confidence: 99%

“…The increased H 2 O 2 reactivity is related to several TS-1 characteristics, including microporosity, hydrophobic nature, and the presence of titanium atoms, which reduces the electron density of the O-O bonds, making the oxidant more susceptible to nucleophilic attack (Clerici, 2015;Přech, 2018). TS-1 catalyst has been already tested in guaiacol peroxide oxidation under mild alkaline conditions, producing different DCA, mainly maleic, malic and oxalic acids (Su et al, 2014). These results pointed out the interest to proceed with the testing of TS-1 with other lignin model compounds, namely with the ones with higher complexity.…”

Section: Introductionmentioning

confidence: 99%

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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: 56%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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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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“…Currently, it is used for cyclohexanone ammoximation to caprolactam and the production of propylene oxide [ 95 , 96 , 97 ]. Guaiacol peroxide oxidation using TS-1 in mild alkaline conditions achieved high percentages of MA and oxalic acid, with small percentages of FA and MAL [ 98 ]. Other works oxidizing furfural reported good yields on MA [ 99 , 100 ].…”

Section: Oxidative Depolymerization Of Ligninmentioning

confidence: 99%

Added-Value Chemicals from Lignin Oxidation

2021

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Lignin is the second most abundant component, next to cellulose, in lignocellulosic biomass. Large amounts of this polymer are produced annually in the pulp and paper industries as a coproduct from the cooking process—most of it burned as fuel for energy. Strategies regarding lignin valorization have attracted significant attention over the recent decades due to lignin’s aromatic structure. Oxidative depolymerization allows converting lignin into added-value compounds, as phenolic monomers and/or dicarboxylic acids, which could be an excellent alternative to aromatic petrochemicals. However, the major challenge is to enhance the reactivity and selectivity of the lignin structure towards depolymerization and prevent condensation reactions. This review includes a comprehensive overview of the main contributions of lignin valorization through oxidative depolymerization to produce added-value compounds (vanillin and syringaldehyde) that have been developed over the recent decades in the LSRE group. An evaluation of the valuable products obtained from oxidation in an alkaline medium with oxygen of lignins and liquors from different sources and delignification processes is also provided. A review of C4 dicarboxylic acids obtained from lignin oxidation is also included, emphasizing catalytic conversion by O2 or H2O2 oxidation.

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“…The oxidative cracking includes the cleavage of aryl ether bonds, C − C bonds, aromatic rings, or other linkages of lignin polymer. Nitrobenzene (Sun, Lawther, & Banks, 1995), metal oxides (Voitl, & Von Rohr, 2008), molecular oxygen (Aarabi, Mizani, & Honarvar, 2017;Voitl, Nagel, & Von Rohr, 2010), and hydrogen peroxide (Su, Yang, Liu, & Lin, 2014) are the most regular oxidants.…”

mentioning

confidence: 99%

Oxidative conversion of lignin isolated from wheat straw into aromatic compound catalyzed by NaOH/NaAlO₂

Ke-hui

Zhao

Fan

et al. 2020

Food Science & Nutrition

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Lignin was isolated from wheat straw via organosolv process and further transferred to monophenolic compounds via oxidative conversion. Wheat straw lignin (WSL) with purity at 91.4 wt% was acquired in the presence of heterogeneous and recyclable catalyst of Amberlyst‐45. WSL was characterized by infrared spectrometer (IR), nuclear magnetic resonance spectroscopy (NMR) including 1 H NMR and 13 C NMR spectra. The results showed that WSL possesses typical syringyl (S), guaiacyl (G), and p ‐hydroxyphenyl (H) units, and it is mainly composed of S and G units. The product distribution was dependent on the composition of WSL. Derivatives from S and G units were found to be the main products. The oxidative conversion of WSL was performed by varying oxidant and catalyst. Both the formation of monophenolic compounds and aromatic aldehydes were enhanced by combining oxidants and catalysts. The composite catalyst composed of NaOH/NaAlO 2 was effective for the oxidation of WSL in the presence of nitrobenzene and atmospheric pressure air. The total yield of monophenolic compounds reached up 18.1%, and yields at 6.3 and 5.7% for syringaldehyde and vanillin were achieved, respectively.

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Low-temperature oxidation of guaiacol to maleic acid over TS-1 catalyst in alkaline aqueous H2O2 solutions

Cited by 17 publications

References 119 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

Added-Value Chemicals from Lignin Oxidation

Oxidative conversion of lignin isolated from wheat straw into aromatic compound catalyzed by NaOH/NaAlO₂

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Low-temperature oxidation of guaiacol to maleic acid over TS-1 catalyst in alkaline aqueous H2O2 solutions

Cited by 17 publications

References 119 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

Added-Value Chemicals from Lignin Oxidation

Oxidative conversion of lignin isolated from wheat straw into aromatic compound catalyzed by NaOH/NaAlO2

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Oxidative conversion of lignin isolated from wheat straw into aromatic compound catalyzed by NaOH/NaAlO₂