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Method for preparation of cyclic myrac aldehydes by supported ruthenium oxide catalysis of myrac aldehyde

A rhenium oxide catalyzed and supported technology, which is applied to the preparation of carbon-based compounds, chemical instruments and methods, metal/metal oxide/metal hydroxide catalysts, etc., can solve the problem that the catalyst cannot be reused, the product is not easy to separate, and the catalyst Achieving high atom economy, high selectivity, and fast reaction speed

Active Publication Date: 2019-04-19
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

The traditional production process of citrus cyanal uses protonic acids such as sulfuric acid, phosphoric acid, p-toluenesulfonic acid, Amberlite H + etc. are catalysts (Bull.Chem.Soc.Chim.Fr.1959,601-606; EP 0743297, priority 16.5.1995to Givaudan[Chem.Abstr.126,103856h]), there is a large amount of catalyst, easy to produce waste acid, The reaction conditions are relatively harsh, the product is not easy to separate, the environmental pollution is serious, and the catalyst cannot be reused.

Method used

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  • Method for preparation of cyclic myrac aldehydes by supported ruthenium oxide catalysis of myrac aldehyde
  • Method for preparation of cyclic myrac aldehydes by supported ruthenium oxide catalysis of myrac aldehyde
  • Method for preparation of cyclic myrac aldehydes by supported ruthenium oxide catalysis of myrac aldehyde

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Re 2 o 7 The specific preparation method of / AC is as follows:

[0019] 76 mg of ammonium perrhenate was dissolved in 1.7 g of water, and then the solution was impregnated into 1 g of activated carbon support (AC) by equal volume impregnation. After oven drying at 120 °C for 12 h, the catalyst precursor was placed in N 2 The temperature-programmed reaction was carried out in the atmosphere, and the specific reaction process was as follows: 1.0 g of the dried precursor was heated from room temperature to 400 ° C in a quartz reaction tube for 1 h, and then the temperature was raised to 500 ° C at 1 ° C / min and kept for 3 h, N 2 The flow rate is 60ml / min. get Re 2 o 7 The loading amount is 5wt% Re 2 o 7 / AC Catalyst.

[0020] Other conditions remain the same, only changing the concentration of ammonium perrhenate in the impregnation solution to obtain Re 2 o 7 The loading amounts were 0.1wt%, 0.5wt%, 1wt%, 2wt%, 5wt%, 8wt%, 10wt%, 20wt% Re 2 o 7 / AC Catalyst. ...

Embodiment 2-17

[0022] Re 2 o 7 / AC catalyzed the selective cyclization of p-citrus aldehyde to prepare citrus aldehyde: 0.5g of citrus aldehyde was mixed with a certain quality of Re in the reaction kettle 2 o 7 / AC catalysts were dissolved in 50ml of toluene, replaced with nitrogen five times to make the initial pressure of nitrogen 0.1MPa, the temperature was raised to 50-200°C, and the stirring reaction was carried out at a speed of 1000 rpm for 0.5-24h. After the reaction was completed, the temperature was lowered to room temperature, and the supernatant was filtered and then sampled for analysis. Qualitative analysis of the product was carried out by GC-MS technology and standard sample control, and quantitative analysis was realized by gas chromatography internal standard method. The reaction results are shown in Table 1.

[0023] Table 1 Re under different conditions 2 o 7 / AC catalyzed the cyclization reaction of 4-(4-methyl-3-pentenyl)-3-cyclohexenal (p-citral) to produce cycl...

Embodiment 23-29

[0027] Re 2 o 7 / AC catalyzed meta-citrus aldehyde selective cyclization to prepare cyclic citrus aldehyde: 0.5g meta-citrus aldehyde and 100mg Re 2 o 7 / AC catalysts were respectively dissolved in 50ml of toluene, replaced with nitrogen five times to make the initial pressure of nitrogen 0.1MPa, the temperature was raised to 120°C, and the stirring reaction was carried out at a speed of 1000 rpm for 10h. After the reaction was completed, the temperature was lowered to room temperature, and the supernatant was filtered and then sampled for analysis. Qualitative analysis of the product was carried out by GC-MS technology and standard sample control, and quantitative analysis was realized by gas chromatography internal standard method. The reaction results are shown in Table 2.

[0028] Table 2Re 2 o 7 / AC catalyzed the cyclization reaction of 3-(4-methyl-3-pentenyl)-3-cyclohexenal (meta-citral) to produce cyclocitral 1,2,3,4,5,6 , 7,8-octahydro-,5,5-dimethyl-2-naphthalde...

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Abstract

The invention provides a new method for catalyzing cyclization reaction of myrac aldehyde for conversion to cyclic myrac aldehydes by using Re2O7 / AC as a catalyst. According to the method, by using anorganic small molecular reagent as a reaction solvent and Re2O7 / AC as a catalyst and under a mild condition, 4-(4-methyl-3-pentenyl)-3-cyclohexenal(p-myrac aldehyde) and 3-(4-methyl-3-pentenyl)-3-cyclohexenal (m-myrac aldehyde) undergo selective cyclization to prepare cyclic myrac aldehydes (1,2,3,4,5,6,7,8-octahydro-5,5-dimethyl-2-naphthaldehyde and 1,2,3,4,5,6,7,8-octahydro-5,5-dimethyl-2-naphthaldehyde). In comparison with a traditional cyclic myrac aldehydes production method, the invention has the following distinctive characteristics: the reaction condition is mild; the target product has high selectivity and the reaction is rapid; the catalyst is activated carbon-supported cerium oxide and can be recycled so as to avoid generation of a waste acid solution by traditional catalysis;and the method is environmentally friendly.

Description

technical field [0001] The present invention provides a Re 2 o 7 / AC is a catalyst, and the supported rhenium oxide catalyzes the method for preparing cyclic citrus aldehyde from citrus aldehyde. Specifically, with Re2O7 / AC as a catalyst, 4-(4-methyl-3-pentenyl)-3-cyclohexenal (para-citrus aldehyde) and 3 -(4-Methyl-3-pentenyl)-3-cyclohexenal (meta-citral) selective cyclization to prepare cyclocitral (1,2,3,4,5,6,7, 8-Octahydro-,8,8-dimethyl-2-naphthaldehyde and 1,2,3,4,5,6,7,8-octahydro-5,5-dimethyl-2-naphthaldehyde ). Background technique [0002] The aroma of food and cosmetics is the feeling caused by the particles of volatile substances suspended in the air, stimulating the olfactory nerve through the nostrils, and then transmitted to the brain. With the development of the flavor and fragrance industry, the demand for synthetic fragrances is increasing. Among many synthetic fragrances, the two isomers of citrus aldehyde are 1,2,3,4,5,6,7,8-octahydro-,8,8-dimethyl-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/61C07C47/445B01J23/10
CPCB01J23/10C07C45/61C07C47/445Y02P20/584
Inventor 李昌志祁早娟张波王爱琴张涛
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI