Selective O-alkylation of Phenol Using Dimethyl Ether

Samruddhi, Mane; Bhatkar, Akash; Prabu, Marimuthu; Mekala, Siva Prasad; Gogoi, Pranjal; Mohapatra, Gourab; Thirumalaiswamy, Raja

doi:10.3390/reactions3040040

Open AccessArticle

Selective O-alkylation of Phenol Using Dimethyl Ether

by

Mane Samruddhi

^1,2,

Akash Bhatkar

^1,2,

Marimuthu Prabu

^1,2,

Siva Prasad Mekala

^1,2,

Pranjal Gogoi

^1,2,

Gourab Mohapatra

^1,2 and

Raja Thirumalaiswamy

^1,2,*

¹

Catalysis and Inorganic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India

²

Academy of Scientific and Innovative Research (AcSIR), CSIR-HRDC Campus, Ghaziabad 201002, India

^*

Author to whom correspondence should be addressed.

Reactions 2022, 3(4), 602-614; https://doi.org/10.3390/reactions3040040

Submission received: 28 September 2022 / Revised: 23 October 2022 / Accepted: 31 October 2022 / Published: 17 November 2022

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Abstract

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.

Keywords: phenol; anisole; O-alkylation; dimethyl ether; heterogeneous catalyst

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MDPI and ACS Style

Samruddhi, M.; Bhatkar, A.; Prabu, M.; Mekala, S.P.; Gogoi, P.; Mohapatra, G.; Thirumalaiswamy, R. Selective O-alkylation of Phenol Using Dimethyl Ether. Reactions 2022, 3, 602-614. https://doi.org/10.3390/reactions3040040

AMA Style

Samruddhi M, Bhatkar A, Prabu M, Mekala SP, Gogoi P, Mohapatra G, Thirumalaiswamy R. Selective O-alkylation of Phenol Using Dimethyl Ether. Reactions. 2022; 3(4):602-614. https://doi.org/10.3390/reactions3040040

Chicago/Turabian Style

Samruddhi, Mane, Akash Bhatkar, Marimuthu Prabu, Siva Prasad Mekala, Pranjal Gogoi, Gourab Mohapatra, and Raja Thirumalaiswamy. 2022. "Selective O-alkylation of Phenol Using Dimethyl Ether" Reactions 3, no. 4: 602-614. https://doi.org/10.3390/reactions3040040

APA Style

Samruddhi, M., Bhatkar, A., Prabu, M., Mekala, S. P., Gogoi, P., Mohapatra, G., & Thirumalaiswamy, R. (2022). Selective O-alkylation of Phenol Using Dimethyl Ether. Reactions, 3(4), 602-614. https://doi.org/10.3390/reactions3040040

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Selective O-alkylation of Phenol Using Dimethyl Ether

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