Method for oxidizing aromatic compound having alkyl substituent, method for producing aromatic aldehyde compound and method for producing aromatic carboxylic acid ester
A technology of alkyl substituents and aromatic compounds, which is applied in the preparation of organic compounds, preparation of carbon-based compounds, metal/metal oxide/metal hydroxide catalysts, etc., and can solve problems such as large by-product salts
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[0053] Specific examples include: (1) aromatic compounds containing only alkyl substituents, such as toluene, xylene, ethylbenzene, cumene, methylcumene, pseudocumene, and methylnaphthalene; (2) Aromatic compounds whose alkyl substituents also contain hydroxyl groups, such as cresol and methylnaphthol; (3) aromatic compounds that contain oxygen- or nitrogen-containing substituents in addition to alkyl substituents, such as anisole, methyl Theophylline, methylbenzoquinone, methylnaphthol, menaquinone, nitrotoluene, and methylaniline. Among these compounds, (2) aromatic compounds containing a hydroxyl group in addition to an alkyl substituent can provide high yield and high selectivity of the desired product; therefore, they can be preferably used. That is, preferably used are cresols such as o-, m-, and p-cresols; and methylnaphthols such as 2-methyl-1-naphthol, 4-methyl-1-naphthol, 7-methyl -1-naphthol and 1-methyl-2-naphthol. In particular, cresols such as o-, m-, and p-cre...
preparation Embodiment 1
[0081] Au-Pd / Ti / SiO 2 Example of
[0082] First, to 100 g of commercially available silica carrier powder (Fuji Silysia Chemical Ltd.: "CARiACT Q-6"), 200 ml of 2- propanol solution. After proper stirring, the solvent was removed by distillation under heating, so that the titanium compound was impregnated and supported on the silica carrier. Then, the silica support was dried at 110° C. for 10 hours, and calcined in air at 600° C. for 4 hours.
[0083] Then, 500 ml of an aqueous chloroauric acid solution having a concentration of 18 mmol / L was adjusted to pH 10 with a 1N aqueous sodium hydroxide solution while maintaining the temperature at 65°C to 70°C. To this aqueous solution, add 25ml of tetraammine palladium hydroxide [(NH 3 ) 4 Pd(OH) 2 ] (Pd content: 20 g / L; obtained from TOKURIKIHONTEN CO., LTD), into which 20 g of the above-mentioned titanium-containing silica support was put, and the mixture was further stirred for 1 hour while maintaining 65° C. to a temperat...
preparation Embodiment 2
[0085] Au-Pt / Ti / SiO 2 Example of
[0086] By the same operation as described in Catalyst Preparation Example 1, a gold- and palladium-containing catalyst (Au-Pt / Ti / SiO 2 ), the difference is: 36ml of tetraammine platinum hydroxide [(NH 3 ) 4 Pt(OH) 2 ] (Pt content: 10 g / L; obtained from Tanaka Kikinzoku Kogyo Co. Ltd.) was used instead of the 25 ml aqueous solution of tetraamminepalladium hydroxide in Catalyst Preparation Example 1. The amounts of gold and platinum supported on the catalyst by fluorescent X-ray analysis were 8.0% by mass and 1.7% by mass, respectively. In addition, the observation of metal particle size by transmission electron microscope shows that almost all metal species are highly dispersed on the carrier with a particle size not greater than 10nm, and their apparent average particle size is not greater than 10nm.
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