Zeolite catalyzed highly selective synthesis of 2-methoxy-6-acetylnaphthalene by Friedel-Crafts acylation of 2-methoxynaphthalene in acetic acid reaction media

Yamazaki, Toshiaki; Makihara, Makoto; Komura, Kenichi

doi:10.1016/j.molcata.2016.11.012

Cited by 19 publications

(3 citation statements)

References 23 publications

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“…as an acylating agent in acetic acid (AcOH) as a solvent, and this reaction system is to be the highest conversion of 2-MN and the selectivity of 2,6-ACMN comparing with ever reported researches [18]. However the reusability of mordenite catalyst was found to be poor due to leaching of Al or heavy coke formation onto the acid site during the reaction, and it is marked that the reaction smoothly occurred using low acid amount of mordenite zeolite with SiO 2 /Al 2 O 3 = 200 (designated as MOR(200)), whereas usage higher acid amount of mordenite catalyst caused low conversion of 2-MN, offering quite unique specific character of this reaction system.…”

Section: Introductionmentioning

confidence: 69%

A Novel Friedel-Crafts Acylation Reaction of Anisole for Production of 4-Methoxyacetophenone with High Selectivity and Sufficient Reusability of Mordenite Zeolite Catalyst

Makihara¹,

Komura²

2017

GSC

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Zeolite catalyzed Friedel-Crafts reactions were examined using acetic anhydride as an acetylating agent and an acetic acid as a solvent. It revealed that the reaction of anisole smoothly occurred quantitatively for 3 h using mordenite zeolite with SiO 2 /Al 2 O 3 = 200, and with SiO 2 /Al 2 O 3 = 110, the increasing of Brønsted acidity allowed to completely react within 2 h. Furthermore the selectivity of 4-methoxyacetophenone (4-MA) among the isomers was found to be quantitative, no by-products and/or isomers were not detectable. With the excellent recyclability and reusability, the mordenite zeolite exhibited at least 30 times quantitatively both conversion of anisole and selectivity of 4-MA. The mordenite catalysts of fresh and the used after 30 times were characterized. This opportunity obviously indicates the sufficient shape selective catalyst of mordenite zeolite and gives a green synthetic tool for heterogeneous acylation reaction.

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Section: Introductionmentioning

confidence: 69%

A Novel Friedel-Crafts Acylation Reaction of Anisole for Production of 4-Methoxyacetophenone with High Selectivity and Sufficient Reusability of Mordenite Zeolite Catalyst

Makihara¹,

Komura²

2017

GSC

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“…Acetic acid (AcAc)–water mixtures are of major interest in science and engineering, e.g., in chemical engineering, environmental science, and biotechnology. , For instance, AcAc, often mixed with water, is used as a solvent in different reactions (e.g., Friedel–Crafts alkylation), in medicine (visual inspection with acetic acid), cervical cancer screening, and also widely used in the food industry . A common goal in all these applications is to define strategies to rationally choose the optimal mixture composition (the mole fraction of AcAc as well as that of possible additional compounds) for a target application.…”

Section: Introductionmentioning

confidence: 99%

From Local Hydration Motifs in Aqueous Acetic Acid Solutions to Macroscopic Mixing Thermodynamics: A Quantitative Connection from THz-Calorimetry

Bag,

Pezzotti,

Das Mahanta

et al. 2023

J. Phys. Chem. B

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We report the results of THz measurements (30–440 cm–1) of aqueous acetic acid solutions over the full mixing range (X AcAc = 0–1). We recorded spectroscopic observables as a function of the acetic acid concentration in the frequency range of the intermolecular stretch at 150 cm–1 and of the librational modes at 350–440 cm–1. This allowed us to unravel changes in hydrophobic and hydrophilic hydration motifs, respectively. By means of a novel THz-calorimetry approach, we quantitatively correlated these changes in local hydration motifs to excess mixing entropy and enthalpy. We find that ΔH mix is determined by both hydrophobic and hydrophilic solvation contributions. In contrast, ΔS mix is governed by hydrophobic cavity formation. Our results further suggest that acetic acid–water mixtures are systems at the edge of phase separation due to endothermic contributions from both hydrophilic and hydrophobic solvation in a large portion of the miscibility range. Our work establishes a quantitative relationship between the balance of local hydrophobic and hydrophilic solvation motifs and the macroscopic mixing thermodynamic properties.

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“…Conventionally, aromatic ketones were produced by the oxidation of aromatics (attached methylene groups) using KMnO 4 and K 2 Cr 2 O 7 as inorganic oxidizing agents and homogeneous acid catalysts, which is famously known as the Friedel–Crafts acylation process. However, the above method leads to poor selectivity of acetophenone and produces highly toxic and corrosive wastes that need disposal . Therefore, the increasing concern for the green environment has attracted the scientists as well as researchers to consider the eco‐friendly method with eco‐friendly catalyst.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of polymer‐silica hybrid‐supported catalysts for solvent‐free oxidation of ethylbenzene with TBHP

Chaudhary

Sharma

2020

Asia-Pacific J Chem Eng

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Polymer-silica hybrid support was synthesized, and Cu (II), Co (II), Mn (II), and Ni (II) metals were loaded over hybrid support by incipient impregnation method. Oxidation of ethylbenzene was performed for catalytic evaluation of catalysts at different reaction conditions, that is, the mole ratio of ethylbenzene to TBHP and reaction temperature. The main reaction product was acetophenone along with benzaldehyde as the minor product. The highest ethylbenzene conversion (96.5%) was attained at a 1:3 mole ratio of ethylbenzene to TBHP and temperature at 100 C. Activation energy and reusability of the catalysts were also determined, and results showed that they can be easily reused three times without much loss in their structural and catalytic properties.

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Zeolite catalyzed highly selective synthesis of 2-methoxy-6-acetylnaphthalene by Friedel-Crafts acylation of 2-methoxynaphthalene in acetic acid reaction media

Cited by 19 publications

References 23 publications

A Novel Friedel-Crafts Acylation Reaction of Anisole for Production of 4-Methoxyacetophenone with High Selectivity and Sufficient Reusability of Mordenite Zeolite Catalyst

A Novel Friedel-Crafts Acylation Reaction of Anisole for Production of 4-Methoxyacetophenone with High Selectivity and Sufficient Reusability of Mordenite Zeolite Catalyst

From Local Hydration Motifs in Aqueous Acetic Acid Solutions to Macroscopic Mixing Thermodynamics: A Quantitative Connection from THz-Calorimetry

Synthesis of polymer‐silica hybrid‐supported catalysts for solvent‐free oxidation of ethylbenzene with TBHP

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