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Issue 63, 2014
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The efficient hydroxyalkylation of phenol with formaldehyde to bisphenol F over a thermoregulated phase-separable reaction system containing a water-soluble Brønsted acidic ionic liquid

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Abstract

The efficient hydroxyalkylation of phenol with formaldehyde to bisphenol F over a thermoregulated phase-separable reaction system containing a water-soluble Brønsted acidic ionic liquid was studied. The reaction system containing the water-soluble IL showed thermoregulated biphasic behavior with change of the alkyl chain length of IL, temperature and water amount. Four types of imidazolium-, ammonium-, phosphonium- and pyridinium-based water-soluble ionic liquids with different anions of dihydrogen phosphate [H2PO4], acetate [CH3COO] and hydrogen sulfate [HSO4] were used as both Brønsted acidic catalysts and thermoregulated solvents. Among them, [C6MIM][HSO4] gave a high yield of 80.5% and a selectivity of 96.9% for bisphenol F, and the optimal reaction conditions were stirring speed 450 rpm, phenol–formaldehyde ratio 6 : 1, IL catalyst molar concentration 12.5%, reaction temperature 90 °C and reaction time 1 h. [C6MIM][HSO4] could be recovered by simple decantation and could retain its original activity even after six recycling-uses [CnMIM][HSO4] with the alkyl chain length n = 6 found to be the most suitable for the synthesis of bisphenol F because of both the formation of a thermoregulated monophasic reaction system at 90 °C to enhance the reaction efficiency and as a thermoregulated phase-transition solvent to facilitate its recovery from the reaction system.

Graphical abstract: The efficient hydroxyalkylation of phenol with formaldehyde to bisphenol F over a thermoregulated phase-separable reaction system containing a water-soluble Brønsted acidic ionic liquid

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Publication details

The article was received on 31 Mar 2014, accepted on 07 Jul 2014 and first published on 07 Jul 2014


Article type: Paper
DOI: 10.1039/C4RA02827A
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RSC Adv., 2014,4, 33466-33473

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    The efficient hydroxyalkylation of phenol with formaldehyde to bisphenol F over a thermoregulated phase-separable reaction system containing a water-soluble Brønsted acidic ionic liquid

    Q. Wang, Z. M. Wu, Y. Li, Y. Tan, N. Liu and Y. Liu, RSC Adv., 2014, 4, 33466
    DOI: 10.1039/C4RA02827A

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