Selective O-alkylation of Phenol Using Dimethyl Ether

• 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
• ISSN: 2624-781X; 2624-781X
• DOI: 10.3390/reactions3040040

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.