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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

Inactive Publication Date: 2006-11-15
NIPPON SHOKUBAI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition to the serious problem that this preparation method requires multi-stage reaction steps, the serious problem of generating a large amount of by-product salts remains to be solved

Method used

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Examples

Experimental program
Comparison scheme
Effect test

specific example

[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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Abstract

The present invention relates a method for oxidation of an aromatic compound having an alkyl substituent, including reacting the aromatic compound having an alkyl substituent with an oxygen molecule to oxidize the alkyl substituent into an aldehyde group in the presence of a catalyst containing Ag and / or Au, and, if necessary, any one or more kinds of group VIII elements, supported on a carrier. The oxidation method of the present invention allows the production of an aromatic aldehyde compound or an aromatic carboxylic acid ester via this aromatic aldehyde compound in high yield and in high selectivity by the use of a catalyst having moderate oxidizing ability, even when an aromatic compound having an alkyl substituent, which is easily converted into an aromatic carboxylic acid by oxidation, is used as a starting material.

Description

technical field [0001] The present invention relates to a method for oxidizing an alkyl substituent to an aldehyde group using an aromatic compound containing an alkyl substituent and oxygen as raw materials, and also relates to the preparation of an aromatic aldehyde compound and an aromatic carboxylic acid ester using this oxidation method Methods. Background technique [0002] Conventional methods for the preparation of aromatic aldehydes, especially the oxidation of aromatic compounds containing alkyl substituents with oxygen to obtain aromatic aldehydes, are difficult to prepare aromatic aldehydes in high yield and high selectivity. This is probably due to the reason that aldehydes as products can easily undergo continuous oxidation by which they are oxidized to aromatic carboxylic acids. So far, aromatic aldehyde compounds have been produced as by-products in the production of aromatic carboxylic acids, or by other oxidation methods or by other reactions with other st...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/36B01J23/48B01J23/52B01J35/00C07B61/00C07C47/54C07C47/56C07C47/565C07C67/39C07C69/78C07C69/84
CPCB01J23/48B01J23/52B01J35/0013C07C45/36C07C67/39C07C47/565C07C47/54C07C69/78C07C69/84
Inventor 林利生
Owner NIPPON SHOKUBAI CO LTD