Commercial gold(III)complex supported on functionalized carbon materials as catalyst for cyclohexane hydrocarboxylation

Ekaterina Pakrieva, Ana P.C. Ribeiro, Luísa M.D.R.S. Martins, Inês A.S. Matias, Sónia A.C. Carabineiro, Ekaterina Kolobova, Armando J.L. Pombeiro, José L. Figueiredo, Alexey Pestryakov

Результат исследований: Материалы для журналаСтатья

Выдержка

The commercial dichloro(2-pyridinecarboxylato)gold(III)complex (1), anchored on different carbon materials, is reported for the first time as a catalyst in the cyclohexane hydrocarboxylation to cyclohexanecarboxylic acid. The reaction was carried out in the presence of CO and water, peroxodisulfate, at ca. 50 °C, with 1 in solution and anchored on carbon nanotubes, carbon xerogel or activated carbon, with three different surface chemistries: original forms (CNT, CX or AC, respectively), oxidized with HNO3 (-ox)or oxidized with HNO3 and subsequently treated with NaOH (-ox-Na). 1@CNT-ox-Na was the best catalyst, yielding up to 78% of cyclohexanecarboxylic with a selectivity of 99%. Recycling studies showed that the catalyst was stable up to 4 cycles, the first decrease (11%)on the hydrocarboxylation yield being observed on the 5th cycle. No leaching of gold was found into the solution. The hydrocarboxylation of other cycloalkanes (cyclopentane, cycloheptane and cyclooctane)was also tested in the best conditions found for cyclohexane, but the respective carboxylic acids were obtained in considerably lower yields, which can be explained by different stabilities of cycloalkyl radicals.

Язык оригиналаАнглийский
ЖурналCatalysis Today
DOI
СостояниеОпубликовано - 1 янв 2019

Отпечаток

Cyclohexane
Gold
Carbon
Catalysts
Cycloheptanes
Cycloparaffins
Cyclopentanes
Xerogels
Carbon Nanotubes
Carbon Monoxide
Carboxylic Acids
Surface chemistry
Carboxylic acids
Activated carbon
Leaching
Recycling
Carbon nanotubes
Acids
Water

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Цитировать

Commercial gold(III)complex supported on functionalized carbon materials as catalyst for cyclohexane hydrocarboxylation. / Pakrieva, Ekaterina; Ribeiro, Ana P.C.; Martins, Luísa M.D.R.S.; Matias, Inês A.S.; Carabineiro, Sónia A.C.; Kolobova, Ekaterina; Pombeiro, Armando J.L.; Figueiredo, José L.; Pestryakov, Alexey.

В: Catalysis Today, 01.01.2019.

Результат исследований: Материалы для журналаСтатья

Pakrieva, Ekaterina ; Ribeiro, Ana P.C. ; Martins, Luísa M.D.R.S. ; Matias, Inês A.S. ; Carabineiro, Sónia A.C. ; Kolobova, Ekaterina ; Pombeiro, Armando J.L. ; Figueiredo, José L. ; Pestryakov, Alexey. / Commercial gold(III)complex supported on functionalized carbon materials as catalyst for cyclohexane hydrocarboxylation. В: Catalysis Today. 2019.
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abstract = "The commercial dichloro(2-pyridinecarboxylato)gold(III)complex (1), anchored on different carbon materials, is reported for the first time as a catalyst in the cyclohexane hydrocarboxylation to cyclohexanecarboxylic acid. The reaction was carried out in the presence of CO and water, peroxodisulfate, at ca. 50 °C, with 1 in solution and anchored on carbon nanotubes, carbon xerogel or activated carbon, with three different surface chemistries: original forms (CNT, CX or AC, respectively), oxidized with HNO3 (-ox)or oxidized with HNO3 and subsequently treated with NaOH (-ox-Na). 1@CNT-ox-Na was the best catalyst, yielding up to 78{\%} of cyclohexanecarboxylic with a selectivity of 99{\%}. Recycling studies showed that the catalyst was stable up to 4 cycles, the first decrease (11{\%})on the hydrocarboxylation yield being observed on the 5th cycle. No leaching of gold was found into the solution. The hydrocarboxylation of other cycloalkanes (cyclopentane, cycloheptane and cyclooctane)was also tested in the best conditions found for cyclohexane, but the respective carboxylic acids were obtained in considerably lower yields, which can be explained by different stabilities of cycloalkyl radicals.",
keywords = "Carbon materials functionalization, Cyclohexane hydrocarboxylation, Cyclohexanecarboxylic acid, C̶[sbnd]H activation, Dichloro(2-pyridinecarboxylato)gold(III)complex",
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T1 - Commercial gold(III)complex supported on functionalized carbon materials as catalyst for cyclohexane hydrocarboxylation

AU - Pakrieva, Ekaterina

AU - Ribeiro, Ana P.C.

AU - Martins, Luísa M.D.R.S.

AU - Matias, Inês A.S.

AU - Carabineiro, Sónia A.C.

AU - Kolobova, Ekaterina

AU - Pombeiro, Armando J.L.

AU - Figueiredo, José L.

AU - Pestryakov, Alexey

PY - 2019/1/1

Y1 - 2019/1/1

N2 - The commercial dichloro(2-pyridinecarboxylato)gold(III)complex (1), anchored on different carbon materials, is reported for the first time as a catalyst in the cyclohexane hydrocarboxylation to cyclohexanecarboxylic acid. The reaction was carried out in the presence of CO and water, peroxodisulfate, at ca. 50 °C, with 1 in solution and anchored on carbon nanotubes, carbon xerogel or activated carbon, with three different surface chemistries: original forms (CNT, CX or AC, respectively), oxidized with HNO3 (-ox)or oxidized with HNO3 and subsequently treated with NaOH (-ox-Na). 1@CNT-ox-Na was the best catalyst, yielding up to 78% of cyclohexanecarboxylic with a selectivity of 99%. Recycling studies showed that the catalyst was stable up to 4 cycles, the first decrease (11%)on the hydrocarboxylation yield being observed on the 5th cycle. No leaching of gold was found into the solution. The hydrocarboxylation of other cycloalkanes (cyclopentane, cycloheptane and cyclooctane)was also tested in the best conditions found for cyclohexane, but the respective carboxylic acids were obtained in considerably lower yields, which can be explained by different stabilities of cycloalkyl radicals.

AB - The commercial dichloro(2-pyridinecarboxylato)gold(III)complex (1), anchored on different carbon materials, is reported for the first time as a catalyst in the cyclohexane hydrocarboxylation to cyclohexanecarboxylic acid. The reaction was carried out in the presence of CO and water, peroxodisulfate, at ca. 50 °C, with 1 in solution and anchored on carbon nanotubes, carbon xerogel or activated carbon, with three different surface chemistries: original forms (CNT, CX or AC, respectively), oxidized with HNO3 (-ox)or oxidized with HNO3 and subsequently treated with NaOH (-ox-Na). 1@CNT-ox-Na was the best catalyst, yielding up to 78% of cyclohexanecarboxylic with a selectivity of 99%. Recycling studies showed that the catalyst was stable up to 4 cycles, the first decrease (11%)on the hydrocarboxylation yield being observed on the 5th cycle. No leaching of gold was found into the solution. The hydrocarboxylation of other cycloalkanes (cyclopentane, cycloheptane and cyclooctane)was also tested in the best conditions found for cyclohexane, but the respective carboxylic acids were obtained in considerably lower yields, which can be explained by different stabilities of cycloalkyl radicals.

KW - Carbon materials functionalization

KW - Cyclohexane hydrocarboxylation

KW - Cyclohexanecarboxylic acid

KW - C̶[sbnd]H activation

KW - Dichloro(2-pyridinecarboxylato)gold(III)complex

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