Selective O-alkylation of Phenol Using Dimethyl Ether

Anisole is a straw-colored aromatic compound mainly used in making solvents, flavoring agents, perfumes, fuel additives, and in the synthesis industries. Anisole, also known as methoxybenzene, is synthesized from sodium phenoxide or phenol using various methylating agents. The use of dimethyl ether...

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Bibliographic Details
Published in:Reactions (Basel, Switzerland) Switzerland), 2022-12, Vol.3 (4), p.602-614
Main Authors: Samruddhi, Mane, Bhatkar, Akash, Prabu, Marimuthu, Mekala, Siva Prasad, Gogoi, Pranjal, Mohapatra, Gourab, Thirumalaiswamy, Raja
Format: Article
Language:English
Subjects:
Acids
Alkylation
Aluminum oxide
Anisole
Aromatic compounds
Chemicals
Continuously stirred tank reactors
Conversion
Dimethyl ether
Fuel additives
heterogeneous catalyst
Hydrocarbons
Metal oxides
O-alkylation
Perfumes
phenol
Phenols
Reagents
Recyclability
Selectivity
Sodium
Synthesis
Thermodynamic equilibrium
Transitional aluminas
X ray photoelectron spectroscopy
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Summary:Anisole is a straw-colored aromatic compound mainly used in making solvents, flavoring agents, perfumes, fuel additives, and in the synthesis industries. Anisole, also known as methoxybenzene, is synthesized from sodium phenoxide or phenol using various methylating agents. The use of dimethyl ether (DME) as an alkylating agent is seldom reported in the literature. Herein, we have synthesized anisole through the O-alkylation process of phenol and DME to obtain zero discharge from this process. The thermodynamic equilibrium for the reaction of phenol and DME is simulated by using Aspen HYSYS (Hyprotech and Systems). The O-alkylation of phenol has been investigated using phosphotungstic acid (PTA) over γ-Al2O3 with appropriate acidity. Active metal loadings of various percentages were studied and the conversion was optimized at 46.57% with a selectivity of 88.22% at a temperature of 280 °C. The liquid products from the continuously stirred reactor were analyzed with liquid G.C. and the conversion and selectivity were calculated. A comparison of the O-alkylation and C-alkylation of phenol at different temperatures, reactant ratios, residence times, and recyclability was explored, as well as the impact of these factors on the yield of the desired anisole. The catalyst was characterized by XRD, BET, HR-TEM, FE-SEM, elemental mapping, XPS, and DRIFT studies.
ISSN:2624-781X
2624-781X
DOI:10.3390/reactions3040040