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methylation of toluene could be confirmed by the change in the xylenes selectivity, i.e., the p-/m-xylene selectivity (a maximum of 24.0% at 673 K) is about 1.4 times as that without methanol (a maximum of 16.7% at 698 K). Moreover, the deoxygenation of xylenols is also another reaction to produce p-/m-xylene. Similarly, the further methylation of xylenes also takes place which can be demonstrated by the increase of polyalkylated benzenes selectivity after adding methanol (i.e., from 2.8% without methanol to 5.3% with methanol at 673 K). The decreased phenol and o-cresol selectivities are observed from 0.1% and 0.9% to 0.0% and 0.4% at 573 K, and from 4.1% and 3.3% to 1.1% and 1.6% at 723 K. There are several reasons for this result: (1) phenol and o-cresol converts into cresols and xylenols via an alkylation reaction, respectively; and (2) phenol and o-cresol undergo HDO in the presence of methanol. A small amount of polyalkylated phenols (1.2% at 723 K) are observed compared with negligible amount in the absence of methanol, which may result from the secondary methylation of xylenols. Above all, the introduction of methanol in the HDO of m-cresol bring several new reactions, including methylation of cresol and toluene, as well as xylenes and other compounds, which obviously improve the selectivity of p-/m-xylene by 44%, possibly through direct methylation of toluene and HDO of xylenols. 2.2.2. Effect of m-Cresol/Methanol Ratio Catalytic hydrodeoxygenation and methylation of m-cresol at different m-cresol/methanol (C/M) ratio were also experimentally studied towards a further understanding of reaction routes (shown in Figure 3). At 698 K, the alkanes selectivity is between 5.6% and 9.6% in the investigated C/M ratio range. With the C/M ratio increasing from 1/1 to 1/8, the benzene and toluene selectivities decrease from 8.3% and 45.1% to 1.5% and 17.8%, while the p-/m-xylene, o-xylene, and polyalkylated benzene selectivities increase from 22.8%, 6.8%, and 4.2% to 33.5%, 10.2%, and 17.3%, which also confirm that the further methylation of benzene, toluene, and xylenes produces toluene, xylenes (p-/m-xylene and o-xylene), and polyalkylated benzenes. Especially, when the C/M ratio is greater than or equal to 1/4, the most abundant compound in the product are xylenes. With an increase of methanol at the C/M ratio of 1/8, the p-/m-xylene selectivity reaches 33.5%, which is as high as 1.5 times of that at the C/M ratio equal to 1/1, and ca. 2.0 times as high as that without methanol. The remarkable improvement in the p-/m-xylene selectivity may be a result of enhanced methylation reaction rate, as well as the other reactions brought by the methanol, such as methanol to aromatics (MTA) process. Of course, an enhanced methylation reaction rate should be taken as one of the most important pathways as discussed below. 210PDF Image | Zeolite Catalysis
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