Cleavage of diphenylether with boron trifluoride under supercritical conditions

Varga, Tamás; Fazekas, Zsolt; Ikeda, Yasuhisa; Tomiyasu, Hiroshi

doi:10.1016/s0896-8446(02)00024-4

Cited by 6 publications

(9 citation statements)

References 6 publications

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“…Lewis acid catalysts such as FeCl 3 , ZnCl 2 , BF 3 , and AlCl 3 have been used to depolymerize lignin, with the result that low yields of phenols were produced. , This was proposed to be a thermodynamically favorable process, since the performance highly depends on the reaction temperature …”

Section: Acid-catalyzed Depolymerizationmentioning

confidence: 99%

“…132,135 This was proposed to be a thermodynamically favorable process, since the performance highly depends on the reaction temperature. 150 Studies by Ekerdt, 134 Vuori, 151 Thring, 132 and their coworkers have demonstrated that Lewis acids became active for lignin depolymerization when they were converted to their Bronsted acid form. It was also found that the reactivity was not an accurate match for the acidity sequence for the hydrolytic cleavage of C−O linkages in lignin model compounds.…”

Section: Lewis Acidmentioning

confidence: 99%

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Catalytic Transformation of Lignin for the Production of Chemicals and Fuels

et al. 2015

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Section: Acid-catalyzed Depolymerizationmentioning

confidence: 99%

Section: Lewis Acidmentioning

confidence: 99%

Catalytic Transformation of Lignin for the Production of Chemicals and Fuels

et al. 2015

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“…We conclude that phenol is stable under the present reaction conditions, but that some other products (e.g., oligomers) must form from DPE. We note that Varga et al also reported low phenol selectivities in their DPE hydrolysis experiments with stoichiometric amounts of BF 3 .…”

Section: Diphenyl Ether (Dpe) Hydrolysismentioning

confidence: 51%

“…35 Penninger et al 34 carried out reactions in water above 400 °C with NaCl and obtained only 3% conversion. Varga et al 33 hydrolyzed DPE in water at 380 °C using stoichiometric amounts of BF 3 and Ni(BF 4 ) 2 . The highest conversion they reported was 58% after 30 min.…”

Section: Diphenyl Ether (Dpe) Hydrolysismentioning

confidence: 99%

“…Diphenyl ether is the simplest aromatic ether, and it models a single-atom bridge between two aromatic units in lignin. , It is stable in supercritical water even in the presence of different catalysts, ,,− although it can be cleaved by catalytic hydrogenolysis if H 2 and an appropriate metal catalyst are used . Penninger et al carried out reactions in water above 400 °C with NaCl and obtained only 3% conversion.…”

Section: Diphenyl Ether (Dpe) Hydrolysismentioning

confidence: 99%

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Hydrolytic Cleavage of C–O Linkages in Lignin Model Compounds Catalyzed by Water-Tolerant Lewis Acids

Yang

Savage

2014

Ind. Eng. Chem. Res.

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We have explored C–O bond cleavage in different lignin model compounds in high-temperature water using catalytic amounts of water-tolerant Lewis acids. Experiments comparing indium triflate, scandium triflate, ytterbium triflate, and indium chloride indicate that indium triflate is the most active catalyst for this cleavage in guaiacol. Reactions of guaiacol at 225, 250, and 275 °C were consistent with first-order kinetics for guaiacol disappearance. The conversion reached 96% at 275 °C after 2 h using indium triflate. Milder temperatures (175, 200, and 225 °C) were sufficient for selective cleavage of the weaker C–O bond in benzyl phenyl ether. The conversion reached 99% at 225 °C after 3 h using indium triflate. The activation energies for guaiacol and benzyl phenyl ether hydrolysis were found to be 134 ± 5 and 98 ± 5 kJ·mol–1, respectively. As expected, diphenyl ether was more resistant to C–O cleavage, but even its very strong aryl–O–aryl bond can be hydrolyzed to form phenol at 330 °C with indium triflate as the catalyst. These results point to the potential application of water-tolerant Lewis acids as catalysts for lignin depolymerization.

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Investigation of Some Functionalization Reactions of 4‐Benzoyl‐5‐phenyl‐1‐(4‐methoxyphenyl)‐1H‐pyrazole‐3‐carbonyl Chloride and Their Antimicrobial Activity

Korkusuz

Yıldırım

Albayrak

2013

J Chinese Chemical Soc

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The 1H-pyrazole-3-carboxylic acid 1 was converted via reactions of its acid chloride 3 with various asymmetrical disubstituted urea and alcohol derivatives into the corresponding novel 4-benzoyl-N-(N',N'-dialkylcarbamyl)-1-(4-methoxyphenyl)-5-phenyl-1H-pyrazole-3-carboxamide 4a,b and alkyl 4-benzoyl-1-(4-methoxyphenyl)-5-phenyl-1H-pyrazole-3-carboxylate 7a-c, respectively, in good yields (57%-78%). Friedel-Crafts reactions of 3 with aromatic compouns for 15 min.-2 h led to the formation of the 4-3-diaroyl-1-(4-hydroxyphenyl)-5-phenyl-1H-pyrazoles 9a-c, 4-benzoyl-1-(4-methoxyphenyl)-3aroyl-5-phenyl-1H-pyrazoles 10a,b and than from the acylation reactions of 9a-c were obtained the 3,4-diaroyl-1-(4-acyloxyphenyl)-5-phenyl-1H-pyrazoles 13a-d. The structures of all new synthesized compounds were established by NMR experiments such as 1 H, and 13 C, as well as 2D COSY and IR spectroscopic data, and elemental analyses. All the compounds were evaluated for their antimicrobial activities (agar diffusion method) against eight bacteria and two yeasts. JOURNAL OF THE CHINESE CHEMICAL SOCIETYAs shown in Scheme II, 4-benzoyl-5-phenyl-1-(4hydroxyphenyl)-1H-pyrazole-3-carboxylic acid 8 was readily prepared by hydrolyzed of Methyl 4-benzoyl-1-(4-methoxyphenyl)-5-phenyl-1H-pyrazole-3-carboxylate

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Cleavage of diphenylether with boron trifluoride under supercritical conditions

Cited by 6 publications

References 6 publications

Catalytic Transformation of Lignin for the Production of Chemicals and Fuels

Catalytic Transformation of Lignin for the Production of Chemicals and Fuels

Hydrolytic Cleavage of C–O Linkages in Lignin Model Compounds Catalyzed by Water-Tolerant Lewis Acids

Investigation of Some Functionalization Reactions of 4‐Benzoyl‐5‐phenyl‐1‐(4‐methoxyphenyl)‐1H‐pyrazole‐3‐carbonyl Chloride and Their Antimicrobial Activity

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