Solvent free selective acylation of phenol by HF–modified saponite catalysts

Thampikannu, Raihamol Erattammottil; Jiménez, Alejandro; Rives, V.; Vicente, Miguel Á.; Razak, Bismi; Vellayan, Kannan

doi:10.1016/j.clay.2022.106695

Cited by 3 publications

(1 citation statement)

References 37 publications

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“…3 In general, acylation is achieved by the reaction of alcohols with anhydrides due to the ease of deprotection. 4,5 Several different catalysts developed for the activation of anhydrides include nucleophilic agents such as 4-dimethylaminopyridine (DMAP) 6 and Bu 3 P, 7 and Lewis acids such as CoCl 2 , [7][8][9] as well as diverse triflates Sc(OTf) 2 , 10 Ce(OTf) 2 , 11 Pd(PhCN) 2 (OTf), 12 TMSOTf, 13 In (OTf) 2 , 14 Bi(OTf) 3 , 15,16 Cu(OTf) 2 17,18 and Cu(CH 3 CN) 4 OTf, 19 TaCl 5 , 20 zeolites, 21 clays, 22 Nafion-H, 23 yttria-zirconia, 24 LiClO 4 25 and ion liquids. 26 However, these catalysts suffer from various limitations.…”

Section: Introductionmentioning

confidence: 99%

Novel base‐catalyzed acylation of benzenediols with vinyl acetate: a Hirshfeld surface study

Ali,

Isaev,

Chichigina

et al. 2024

J of Chemical Tech & Biotech

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BACKGROUNDThe present work describes the facile, fast and economic base‐catalyzed acylation of benzenediols with vinyl acetate. The Hirshfeld surface analysis of benzene‐1,4‐diol O,O′‐diacetate is also described. NaOH, KOH and K2CO3 were the bases used for the catalysis of the acylation of benzene‐1,x‐diols (x = 2, 3, 4) with vinyl acetate to obtain the corresponding O,O′‐diacetyl derivatives.RESULTSThe yields were quite good, up to 99% under solvent‐free conditions. This method represents an alternative ‘green’ process for the preparation of O‐acetyl derivatives of hydroxyaryls. The benzene‐1,4‐diol O,O′‐diacetate crystal structure was obtained and described using Hirshfeld surface analysis. A noticeable contribution of the C⋯H contacts is shown (16.7%), despite the insignificant area of the Hirshfeld surface occupied by the carbon atoms (9.4%). By using two‐dimensional fingerprint plots, it was proved that C⋯H contacts were due to the presence of π‐stacking. The O⋯H contacts (41.4%) were the most numerous ones, relating mainly to typical hydrogen bonds (de + di ≈ 2.6 Å). The high saturation of the C⋯H and O⋯H contacts (enrichment ratios (E) = 1.30 and 1.36, respectively), despite their smaller contribution to the overall surface as compared to the H⋯H contacts (E = 0.84), is shown.CONCLUSIONThe novelty of this work is the development of a method based on an inexpensive, safe and easy‐to‐use catalyst (K2CO3). This method is fast with high yields. Besides, it may be used for acylation at an industrial scale. © 2024 Society of Chemical Industry (SCI).

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Section: Introductionmentioning

confidence: 99%

Novel base‐catalyzed acylation of benzenediols with vinyl acetate: a Hirshfeld surface study

Ali,

Isaev,

Chichigina

et al. 2024

J of Chemical Tech & Biotech

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In-depth insights into transformation mechanism of synthetic saponite to amorphous silica under acid attack

Li,

Ramola,

et al. 2024

Applied Clay Science

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Review of the application of infrared spectroscopy in studies of acid-treated clay minerals

Madejová,

Pálková

2024

Clays and clay miner.

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Acid activation of clay minerals is one of the most effective methods for production of materials with increased acidity and porosity. In this review, the benefits of infrared (IR) spectroscopy in studies of acid-treated clay minerals are demonstrated. Protons penetrating into the clay mineral layers evoke structural modifications that can be followed readily by changes in the characteristic absorption bands attributed to the vibrations of the OH and Si–O groups. In the first part of the review the effect of the clay mineral type, composition, layer charge, non-swelling layers, and organo-modification on the dissolution rate is reported. The identification of the acid sites via pyridine adsorption also included. The purpose was to gather the IR results published in previous studies in a single summary paper. In the second part select recent studies reporting the utilization of IR spectroscopy for the characterization of acid-activated clay minerals, mainly applied as catalysts or adsorbents, are discussed. IR spectroscopy as a simple and non-destructive technique deserves attention also today.

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Solvent free selective acylation of phenol by HF–modified saponite catalysts

Cited by 3 publications

References 37 publications

Novel base‐catalyzed acylation of benzenediols with vinyl acetate: a Hirshfeld surface study

Novel base‐catalyzed acylation of benzenediols with vinyl acetate: a Hirshfeld surface study

In-depth insights into transformation mechanism of synthetic saponite to amorphous silica under acid attack

Review of the application of infrared spectroscopy in studies of acid-treated clay minerals

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