An efficient production of benzene from benzoic acid in subcritical water using a copper(<scp>i</scp>) oxide catalyst

Zheng, Qingxin; Morimoto, Masato; Takanohashi, Toshimasa

doi:10.1039/c4gc01875c

Cited by 12 publications

(6 citation statements)

References 15 publications

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“…The experimental process followed our previous report [27]. The model carboxylic acids used here include six benzene carboxylic acids (o-phthalic acid, isophthalic acid, terephthalic acid, hemimellitic acid, trimellitic acid, and trimesic acid) and three naphthalene carboxylic acids (1-naphthoic acid, 2 naphthoic acid and 2,6-naphthalic acid).…”

Section: Hydrothermal Decarboxylation Of Model Aromatic Carboxylic Acidsmentioning

confidence: 99%

“…As the conversion yield of reaction (I) was 2.4% and 87.4%, without and with a Cu 2 O catalyst, respectively [27], and DY-a was obtained directly using the amount of carbon dioxide, it is easy to calculate CY-II. By following this method and under the assumption that the decarboxylation yields of all the model carboxylic acids are fixed, the exact conversion yields of decarboxylation reactions (II), (III), (IV), (X), (XI), (XII), and (XIII) can be calculated readily.…”

Section: Cy-iimentioning

confidence: 99%

“…The apparatus consisted of a cylinder-shaped autoclave with an internal volume of 50 cm 3 and a rocking electric furnace [27]. The autoclave was equipped with a pressure gauge amplifier and a thermocouple to monitor the inner pressure and temperature, respectively.…”

Section: Apparatusmentioning

confidence: 99%

“…At 250°C and 5 MPa for 14 h, 1-naphthoic acid was converted to naphthalene in 74% yield. Then, in 2015, our group realised the efficient decarboxylation of stable benzoic acid to benzene using a Cu 2 O catalyst and subcritical water at 350°C (Cu 2 O-SbCW system) [27]. The conversion yields reached more than 90% in 90 min with 100% selectivity.…”

Section: Introductionmentioning

confidence: 99%

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A novel process for the production of aromatic hydrocarbons from brown coal in water medium by hydrothermal oxidation and catalytic hydrothermal decarboxylation

Zheng

Morimoto

Takanohashi

2016

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a b s t r a c tWith no use of hydrogen or a hydrogen donor, a novel process is proposed for the production of aromatic hydrocarbons from brown coal in water medium, which consists of hydrothermal oxidation at 240°C and Cu 2 O-catalysed hydrothermal decarboxylation at 350°C. Using this hydrothermal oxidation and catalytic hydrothermal decarboxylation method, aromatic carboxylic acids were formed from brown coal by an oxidation process, and then decarboxylated to the corresponding aromatic hydrocarbons. The validity of the decarboxylation method was examined using several aromatic carboxylic acids as model compounds for the acid products after hydrothermal oxidation of brown coal, including o-phthalic acid, isophthalic acid, terephthalic acid, hemimellitic acid, trimellitic acid, trimesic acid, 1-naphthoic acid, 2-naphthoic acid, and 2,6-naphthalic acid. Use of Cu 2 O catalyst increased the decarboxylation yields of all the aromatic carboxylic acids. Especially for benzene carboxylic acids, all decarboxylation yields were above 90% with 100% selectivity. The Cu 2 O-catalysed hydrothermal method was proven to be effective, not only for the decarboxylation reactions from monocarboxylic acids to hydrocarbons, but also for the decarboxylation reactions from tricarboxylic acids to dicarboxylic acids and from dicarboxylic acids to monocarboxylic acids. In the presence of alkali and oxygen during the oxidation process, various valuable aromatic hydrocarbons and heterocyclic compounds, especially benzene, were obtained from Loy Yang coal using the hydrothermal oxidation and catalytic decarboxylation process. Based on analyses of aromatic carboxylic acids or ions before and after the decarboxylation process, it was found that decarboxylation reactions were the major reactions and the use of Cu 2 O was effective not only for the decarboxylation from monocarboxylic acids but also from polycarboxylic acids to monocarboxylic acids, consistent with the results for the model aromatic carboxylic acids. Additionally, it was found that a Cu 2 O catalyst was also effective for the conversion of 'heavy' compounds in oxidised coal to 'light' compounds.

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Section: Hydrothermal Decarboxylation Of Model Aromatic Carboxylic Acidsmentioning

confidence: 99%

Section: Cy-iimentioning

confidence: 99%

Section: Apparatusmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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A novel process for the production of aromatic hydrocarbons from brown coal in water medium by hydrothermal oxidation and catalytic hydrothermal decarboxylation

Zheng

Morimoto

Takanohashi

2016

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Self Cite

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“…4 On the other hand, the catalytic decarboxylation of benzoic acid as a feasible intermediate can be readily accomplished to produce benzene. 5 However, the active sites that yield benzene are still unclear in this reaction, largely due to their low concentration or weak signals that are easily concealed by prominent bands.…”

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confidence: 99%

Selectivity switching resulting in the formation of benzene by surface carbonates on ceria in catalytic gas-phase oxidation of benzyl alcohol

Dai

Tang

et al. 2016

Chem. Commun.

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The irreversible formation of carbonate deposits on CeO2 leads to complete switching of catalytic selectivity resulting in the formation of benzene in gas-phase oxidation of benzyl alcohol. By integrating experimental spectra and theoretical calculations, we expect that such a shift is derived from further decarbonylation of benzaldehyde via easy trapping of CO fragments by surface carbonate species.

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benzoic acid

Cornils¹

2020

Catalysis From a to Z

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An efficient production of benzene from benzoic acid in subcritical water using a copper(i) oxide catalyst

Abstract: The benzene yield from benzoic acid increased greatly to 90 mol% with 100% selectivity in subcritical water catalyzed by Cu2O.

Cited by 12 publications

References 15 publications

A novel process for the production of aromatic hydrocarbons from brown coal in water medium by hydrothermal oxidation and catalytic hydrothermal decarboxylation

A novel process for the production of aromatic hydrocarbons from brown coal in water medium by hydrothermal oxidation and catalytic hydrothermal decarboxylation

Selectivity switching resulting in the formation of benzene by surface carbonates on ceria in catalytic gas-phase oxidation of benzyl alcohol

benzoic acid

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