Ammonium Tungstate as an Effective Catalyst for Selective Oxidation of Alcohols to Aldehydes or Ketones with Hydrogen Peroxide under Water – A Synergy of Graphene Oxide

Huihui Fu; Chuanfeng Hu; Zhida Huang; Jianhao Zhou; Xinhua Peng

doi:10.1055/s-0036-1590949

Synlett, Inhaltsverzeichnis

Synlett 2018; 29(04): 447-451
DOI: 10.1055/s-0036-1590949

letter

Ammonium Tungstate as an Effective Catalyst for Selective Oxidation of Alcohols to Aldehydes or Ketones with Hydrogen Peroxide under Water – A Synergy of Graphene Oxide

Huihui Fu

School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China eMail: xhpeng@mail.njust.edu.cn

,

Chuanfeng Hu

School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China eMail: xhpeng@mail.njust.edu.cn

,

Zhida Huang

School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China eMail: xhpeng@mail.njust.edu.cn

,

Jianhao Zhou

School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China eMail: xhpeng@mail.njust.edu.cn

,

Xinhua Peng*

School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China eMail: xhpeng@mail.njust.edu.cn

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Abstract

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Abstract

Ammonium tungstate was found to be a facile and efficient catalyst for selective oxidation of alcohols to the corresponding carbonyl compounds with hydrogen peroxide as oxidant. Heterogeneous graphene oxide as acid effectively intensified the transformations and resulted in excellent yields. The use of water as solvent rendered the reactions promising both economically and environmentally.

Key words

alcohol oxidation - hydrogen peroxide - ammonium tungstate - graphene oxide - water

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References and Notes

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19 Experimental procedures: GO (0.01 g) was added into water (3 mL) to generate a stable colloidal suspension under mild ultrasonic treatment. Afterwards, the alcohol (2 mmol) and (NH₄)₅H₅[H₂(WO₄)₆] (0.03 mmol, M = 1602) were added. The mixture was stirred for 15 min at room temperature. Subsequently, hydrogen peroxide (30 wt%, 8 mmol) was added dropwise and the mixture was heated to 70 °C until the reaction was complete (monitored by TLC). GO could then be readily separated from the mixtures by centrifugation, and then ethyl acetate was added to the mixture to extract organic constituents. Finally, the organic extracts were concentrated under reduced pressure and purified by column chromatography.Cyclohexanone (Table [2], entry 1): Yield: 0.18 g (93%); colorless liquid. ¹H NMR (500 MHz, CDCl₃): δ = 2.37 (t, J = 6.7 Hz, 4 H), 2.07–1.82 (m, 4 H), 1.82–1.62 (m, 2 H). ¹³C NMR (126 MHz, CDCl₃): δ = 211.98, 41.92, 26.99, 24.94

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