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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2022-11-01
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| author | Mane Samruddhi Akash Bhatkar Marimuthu Prabu Siva Prasad Mekala Pranjal Gogoi Gourab Mohapatra Raja Thirumalaiswamy |
| author_facet | Mane Samruddhi Akash Bhatkar Marimuthu Prabu Siva Prasad Mekala Pranjal Gogoi Gourab Mohapatra Raja Thirumalaiswamy |
| author_sort | Mane Samruddhi |
| collection | DOAJ |
| description | 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-Al<sub>2</sub>O<sub>3</sub> 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. |
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| language | English |
| last_indexed | 2024-03-09T15:54:46Z |
| publishDate | 2022-11-01 |
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| series | Reactions |
| spelling | doaj.art-bb2e1a07704a4b39a57bcd55ff40c0e12023-11-24T17:43:35ZengMDPI AGReactions2624-781X2022-11-013460261410.3390/reactions3040040Selective O-alkylation of Phenol Using Dimethyl EtherMane Samruddhi0Akash Bhatkar1Marimuthu Prabu2Siva Prasad Mekala3Pranjal Gogoi4Gourab Mohapatra5Raja Thirumalaiswamy6Catalysis and Inorganic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, IndiaCatalysis and Inorganic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, IndiaCatalysis and Inorganic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, IndiaCatalysis and Inorganic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, IndiaCatalysis and Inorganic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, IndiaCatalysis and Inorganic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, IndiaCatalysis and Inorganic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, IndiaAnisole 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-Al<sub>2</sub>O<sub>3</sub> 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.https://www.mdpi.com/2624-781X/3/4/40phenolanisoleO-alkylationdimethyl etherheterogeneous catalyst |
| spellingShingle | Mane Samruddhi Akash Bhatkar Marimuthu Prabu Siva Prasad Mekala Pranjal Gogoi Gourab Mohapatra Raja Thirumalaiswamy Selective O-alkylation of Phenol Using Dimethyl Ether Reactions phenol anisole O-alkylation dimethyl ether heterogeneous catalyst |
| title | Selective O-alkylation of Phenol Using Dimethyl Ether |
| title_full | Selective O-alkylation of Phenol Using Dimethyl Ether |
| title_fullStr | Selective O-alkylation of Phenol Using Dimethyl Ether |
| title_full_unstemmed | Selective O-alkylation of Phenol Using Dimethyl Ether |
| title_short | Selective O-alkylation of Phenol Using Dimethyl Ether |
| title_sort | selective o alkylation of phenol using dimethyl ether |
| topic | phenol anisole O-alkylation dimethyl ether heterogeneous catalyst |
| url | https://www.mdpi.com/2624-781X/3/4/40 |
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