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Method for preparing aldehyde and ketone through alcohol oxidation

A technology of alcohol oxidation and oxygen, which is applied in the direction of chemical instruments and methods, carbon-based compound preparation, organic compound preparation, etc., can solve problems such as pollution and post-processing troubles, and achieve the effects of environmental friendliness, easy product, and mild reaction conditions

Inactive Publication Date: 2015-02-11
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a new method for preparing aldehydes and ketones by catalyzing oxidative oxidation of alcohols with DDQ to overcome the problems of post-processing troubles and pollution in the above-mentioned oxidation system

Method used

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  • Method for preparing aldehyde and ketone through alcohol oxidation
  • Method for preparing aldehyde and ketone through alcohol oxidation
  • Method for preparing aldehyde and ketone through alcohol oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1. Investigation of reaction conditions

[0019] First, we used cinnamyl alcohol as a model substrate to investigate the reaction conditions, and the product was cinnamaldehyde. 1 HNMR(300MHz, CDCl 3 )δ9.71(d,J=7.8Hz,1H), 7.60-7.52(m,3H), 7.47-7.42(m,3H), 6.75(dd,J=15.9,7.8Hz,1H), 13 C NMR(100.6MHz, CDCl 3 )δ128.2, 128.3, 128.8, 131.0, 133.7, 152.7, 193.6.

[0020] The typical reaction steps are as follows: add 13.4g (0.1mol) cinnamyl alcohol, 2.27g (0.01mol) DDQ, 1.137g ferric phthalocyanine (II), 30mL dioxane into a 100mL stainless steel reactor, seal it, and exchange oxygen 3 Next, the oxygen pressure was 0.1Mpa, and the mixture was stirred at 95°C for 10 hours. The dioxane was removed under reduced pressure, the resulting mixture was dissolved in dichloromethane, washed with water, dried to remove the dichloromethane, and 9.7 g of cinnamaldehyde was obtained by column separation (yield 73%).

[0021] The results are shown in Table 1

[0022] Table 1 Investigation o...

Embodiment 2

[0025] Add 124.2g p-hydroxybenzyl alcohol, 22.7g DDQ, 22.73g ferric phthalocyanine (II), 340mL N,N-dimethylformamide into a 500mL reaction flask, seal it, exchange oxygen 3 times, connect the oxygen balloon (0.1Mpa ), stirring at 100°C for 13h. The N,N-dimethylformamide was removed under reduced pressure, the resulting mixture was dissolved in dichloromethane, washed with water, dried to remove the dichloromethane, and 100 g (yield: 81%) of p-hydroxybenzaldehyde light yellow crystals were obtained by column separation. 1 H NMR(400MHz,DMSO):δ6.93(d, 3 J H,H =8.8Hz,1H),7.76(d, 3 J H,H =8.8Hz,2H),9.78(s,1H),10.58(s,1H); 13 C NMR (100.6 MHz, DMSO) δ 116.0, 128.6, 132.3, 163.5, 191.1.

Embodiment 3

[0026] Example 3, benzyl alcohol oxidation

[0027] Add 10.8g of benzyl alcohol, 3.4g of DDQ, 4.25g of phthalocyanine iron(II), and 50mL of acetonitrile into a 100mL stainless steel reactor, and react at 95°C under 0.3MPa oxygen pressure to cool to room temperature for 16 hours, and slowly release oxygen. The acetonitrile was removed by pressure, the resulting mixture was dissolved in dichloromethane, washed with water, dried to remove the dichloromethane, and 9 g (yield: 84%) of benzaldehyde was obtained by column separation. 1 H NMR(300MHz, CDCl 3 ,): δ7.51(t,J=7.6Hz,2H), 7.61(t,J=7.2Hz,1H), 7.86(d,J=7.6Hz,2H), 9.99(s,1H). 13 C NMR(100.6MHz, CDCl 3 ): δ128.7, 129.4, 134.1, 136.0, 192.0.

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Abstract

The present invention provides a method for preparing aldehyde and ketone through alcohol oxidation. The method comprises: adopting 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a catalyst, adopting iron phthalocyanine (II) as a co-catalyst, adopting oxygen (or air) as an oxidant, and oxidizing an alcohol in an organic solvent to generate aldehyde and ketone. The method has characteristics of mild reaction conditions, simple operation and less pollution, and is a new green environmental protection method for preparing aldehyde and ketone through catalysis oxidation of alcohol.

Description

Technical field [0001] The invention relates to the field of catalytic oxidation, in particular to a method for preparing aldehydes and ketones by catalytic oxidation of alcohols. Background technique [0002] The selective oxidation of alcohols to carbonyl compounds is an important reaction in organic synthesis, and is widely used in laboratories and industrial production, and plays a key role in the fine chemical industry. The oxidation of alcohols to aldehydes and ketones with 2,3-dichloro-5,6-dicyanoquinone (DDQ) is a known method. (See Becker et al., The Journal of Organic Chemistry, Volume 45, pages 1596-1600 (1980)). But because DDQ is more expensive, $526 / mol (see 2009-2010 Aldrich catalog), and because its structure contains two -CN groups, it is easy to hydrolyze and produce certain toxicity. This limits its use. From the perspective of economy and environmental friendliness, people have been looking for a way to recycle DDQ, as shown in formula 1, that is, oxidizing...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/38C07C45/39C07C47/232C07C47/565C07C47/54C07C49/786C07C49/603C07C49/643C07C47/277C07C49/217C07C47/575C07C49/796
CPCC07C45/38C07C45/39C07C2601/16C07C2603/18C07C47/232C07C47/565C07C47/54C07C49/786C07C49/643C07C49/603C07C49/84C07C49/794C07C47/575
Inventor 高爽李军王连月吕迎
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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