Vapour-Phase Selective <i>O</i>-Methylation of Catechol with Methanol over Metal Phosphate Catalysts

Guaiacol (2-methoxyphenol), an important fine chemical intermediate, is conventionally synthesized by liquid-phase processes with expensive, corrosive and toxic methylating agents such as dimethyl sulphate and dimethyl iodide. Recently, vapour-phase alkylation of catechol (1, 2-dihydroxybenzene) wit...

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Main Authors: Haifang Mao, Xiaolei Li, Fen Xu, Zuobing Xiao, Wenxiang Zhang, Tao Meng
Format: Article
Language:English
Published: MDPI AG 2021-04-01
Series:Catalysts
Subjects:
Online Access:https://www.mdpi.com/2073-4344/11/5/531
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spelling doaj-c05060c30db64620bd444902bdd7f1522021-04-21T23:03:56ZengMDPI AGCatalysts2073-43442021-04-011153153110.3390/catal11050531Vapour-Phase Selective <i>O</i>-Methylation of Catechol with Methanol over Metal Phosphate CatalystsHaifang Mao0Xiaolei Li1Fen Xu2Zuobing Xiao3Wenxiang Zhang4Tao Meng5School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, ChinaSchool of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, ChinaSchool of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, ChinaSchool of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 201418, ChinaCollege of Chemistry, Jilin University, Changchun 130023, ChinaSchool of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418, ChinaGuaiacol (2-methoxyphenol), an important fine chemical intermediate, is conventionally synthesized by liquid-phase processes with expensive, corrosive and toxic methylating agents such as dimethyl sulphate and dimethyl iodide. Recently, vapour-phase alkylation of catechol (1, 2-dihydroxybenzene) with methanol for the synthesis of guaiacol in the presence of heterogeneous catalysts has received more attention, as the route is economical and environmentally friendly. However, most of the investigated catalysts exhibited unsatisfactory catalytic performance for industrial applications. In this study, five metal phosphates M-P-O (M = La, Ce, Mg, Al, Zn) catalysts were synthesized and tested in the selective <i>O</i>-methylation of catechol with methanol. Among these catalysts, cerium phosphate (CP) showed the highest catalytic activity and guaiacol yield. Lanthanum phosphate (LP) was the second most active, which was still obviously better than magnesium phosphate (MP) and aluminium phosphate (ALP). Zinc phosphate (ZP) was not active in the reaction. Relevant samples were characterized by X-ray diffraction (XRD), Fourier transform infrared (FT-IR), scanning electron microscopy (SEM), N<sub>2</sub> adsorption-desorption, temperature programmed desorption of NH<sub>3</sub> or CO<sub>2</sub> (NH<sub>3</sub>-TPD, CO<sub>2</sub>-TPD). The suitable acid-base properties contribute to the superior catalytic performance of CP. Long-term stability and regeneration tests were also studied.https://www.mdpi.com/2073-4344/11/5/531metal phosphatescatecholmethanol<i>O</i>-methylationguaiacol
collection DOAJ
language English
format Article
sources DOAJ
author Haifang Mao
Xiaolei Li
Fen Xu
Zuobing Xiao
Wenxiang Zhang
Tao Meng
spellingShingle Haifang Mao
Xiaolei Li
Fen Xu
Zuobing Xiao
Wenxiang Zhang
Tao Meng
Vapour-Phase Selective <i>O</i>-Methylation of Catechol with Methanol over Metal Phosphate Catalysts
Catalysts
metal phosphates
catechol
methanol
<i>O</i>-methylation
guaiacol
author_facet Haifang Mao
Xiaolei Li
Fen Xu
Zuobing Xiao
Wenxiang Zhang
Tao Meng
author_sort Haifang Mao
title Vapour-Phase Selective <i>O</i>-Methylation of Catechol with Methanol over Metal Phosphate Catalysts
title_short Vapour-Phase Selective <i>O</i>-Methylation of Catechol with Methanol over Metal Phosphate Catalysts
title_full Vapour-Phase Selective <i>O</i>-Methylation of Catechol with Methanol over Metal Phosphate Catalysts
title_fullStr Vapour-Phase Selective <i>O</i>-Methylation of Catechol with Methanol over Metal Phosphate Catalysts
title_full_unstemmed Vapour-Phase Selective <i>O</i>-Methylation of Catechol with Methanol over Metal Phosphate Catalysts
title_sort vapour-phase selective <i>o</i>-methylation of catechol with methanol over metal phosphate catalysts
publisher MDPI AG
series Catalysts
issn 2073-4344
publishDate 2021-04-01
description Guaiacol (2-methoxyphenol), an important fine chemical intermediate, is conventionally synthesized by liquid-phase processes with expensive, corrosive and toxic methylating agents such as dimethyl sulphate and dimethyl iodide. Recently, vapour-phase alkylation of catechol (1, 2-dihydroxybenzene) with methanol for the synthesis of guaiacol in the presence of heterogeneous catalysts has received more attention, as the route is economical and environmentally friendly. However, most of the investigated catalysts exhibited unsatisfactory catalytic performance for industrial applications. In this study, five metal phosphates M-P-O (M = La, Ce, Mg, Al, Zn) catalysts were synthesized and tested in the selective <i>O</i>-methylation of catechol with methanol. Among these catalysts, cerium phosphate (CP) showed the highest catalytic activity and guaiacol yield. Lanthanum phosphate (LP) was the second most active, which was still obviously better than magnesium phosphate (MP) and aluminium phosphate (ALP). Zinc phosphate (ZP) was not active in the reaction. Relevant samples were characterized by X-ray diffraction (XRD), Fourier transform infrared (FT-IR), scanning electron microscopy (SEM), N<sub>2</sub> adsorption-desorption, temperature programmed desorption of NH<sub>3</sub> or CO<sub>2</sub> (NH<sub>3</sub>-TPD, CO<sub>2</sub>-TPD). The suitable acid-base properties contribute to the superior catalytic performance of CP. Long-term stability and regeneration tests were also studied.
topic metal phosphates
catechol
methanol
<i>O</i>-methylation
guaiacol
url https://www.mdpi.com/2073-4344/11/5/531
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AT xiaoleili vapourphaseselectiveioimethylationofcatecholwithmethanolovermetalphosphatecatalysts
AT fenxu vapourphaseselectiveioimethylationofcatecholwithmethanolovermetalphosphatecatalysts
AT zuobingxiao vapourphaseselectiveioimethylationofcatecholwithmethanolovermetalphosphatecatalysts
AT wenxiangzhang vapourphaseselectiveioimethylationofcatecholwithmethanolovermetalphosphatecatalysts
AT taomeng vapourphaseselectiveioimethylationofcatecholwithmethanolovermetalphosphatecatalysts
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