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Method of preparing benzaldehyde from p-methyl cyclohexene formaldehyde

A technology of methylcyclohexene formaldehyde and benzaldehyde, which is applied to the preparation of carbon-based compounds, chemical instruments and methods, and the preparation of organic compounds, and can solve the problems of limiting the application of benzaldehyde and long reaction process

Active Publication Date: 2016-06-08
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reaction process of the process is long, and the product contains chlorides, which limits the application of benzaldehyde in the perfume and pharmaceutical industries.

Method used

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  • Method of preparing benzaldehyde from p-methyl cyclohexene formaldehyde
  • Method of preparing benzaldehyde from p-methyl cyclohexene formaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: catalyst preparation

[0019] Loaded Pd / TiO 2 Catalyst preparation: Weigh 0.8374g of 20% PdCl 2 Aqueous solution, add water to a total mass of 5g, mix well and impregnate 2.0g TiO 2 (P25), after stirring, let stand for 4 hours, bake at 80°C for 1 hour, then dry overnight at 120°C, and finally reduce passivation. Reduction passivation conditions: in a hydrogen atmosphere (flow rate 120ml / min) from room temperature to 300 ° C within one hour, keep it for 1 hour and then cool down to room temperature, O 2 / N 2 Mixed gas (O 2 Volume content 1%) in passivation 4h, namely obtain 5wt%Pd / TiO 2 , to collect the catalyst for later use.

[0020] According to the above method, Pt, Ru, Ir, Rh, Pd, Au catalysts loaded on silica and zirconia were prepared respectively according to the quality of metal precursors required. The precursors of the above metal catalysts are H 2 PtCl 6 、RuCl 3 , H 2 IrCl 6 , RhCl 3 , H 2 PdCl 4 , HAuCl 4 .

[0021] Preparation...

Embodiment 2

[0028] Add 30ml of toluene, 0.124g of p-methylcyclohexene formaldehyde, 0.05g of Pd / TiO to the autoclave 2 (palladium content 1wt%), with O 2 Filled with 1MPaO after 5 times of replacement 2 , the temperature was raised to 120°C, and the reaction was carried out for 7h. After the reaction was completed, the temperature was lowered to room temperature, the reaction mixture was filtered, and the obtained filtrate was sampled and analyzed. The conversion rate and product yield were quantitatively calculated by GC-MS, and the reaction results are listed in Table 1.

Embodiment 3-10

[0030] Other reaction conditions are the same as in Example 2, and the catalysts used are 0.05 g of Pt / TiO with a loading of 1 wt%, respectively. 2 , Ru / TiO 2 , Ir / TiO 2 , Rh / TiO 2 , Au / TiO 2 , Pd / ZrO 2 , Pt / ZrO 2 , Au / ZrO 2 , and the reaction results are listed in Table 1.

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Abstract

The invention relates to a method of preparing benzaldehyde from p-methyl cyclohexene formaldehyde. According to the method, p-methyl cyclohexene formaldehyde carries out dehydro-aromatization and in-situ oxidation reactions in the presence of a supported transition metal catalyst at a temperature less than 200 DEG C in an atmosphere of oxygen gas so as to selectively generate benzaldehyde. The method has the advantages that the procedure is simple, the selectivity of target product is high, the substrate is obtained through one-step reactions between biomass resources namely isoprene and acrylic aldehyde, and a novel method of directly preparing aromatic chemicals from biomass is provided.

Description

technical field [0001] The present invention relates to the method for preparing benzaldehyde by p-methylcyclohexene formaldehyde (also known as: 4-methyl-3-cyclohexene-1-formaldehyde, English name: 4-Methyl-3-cyclohexene-1-carbaldehyde) . Specifically, it is a method in which p-methylcyclohexene formaldehyde undergoes dehydroaromatization and in-situ oxidation at a temperature not higher than 200° C. under the action of a supported transition metal catalyst to selectively generate benzaldehyde. The reaction procedure of the process is simple, the selectivity of the target product is high, and the substrate can be obtained from isoprene and acrolein derived from biomass resources through Diels-Alder reaction, which provides a new method for directly preparing aromatic aldehydes from biomass. Background technique [0002] Benzaldehyde, also known as benzoin aldehyde, is a colorless liquid at room temperature with a special almond smell and is the second largest fragrance in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/54C07C45/00C07C45/67
Inventor 张涛蔡海乐李昌志王爱琴代弢张波
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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