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Method used for preparation of cyclized myrac aldehyde through catalytic selective cyclization of myrac aldehyde with supported molybdenum carbide

A molybdenum carbide and supported technology is applied in the field of preparing citrus aldehydes through the selective cyclization of citrus aldehydes catalyzed by supported molybdenum carbides. Low cost, high activity and selectivity effect

Active Publication Date: 2019-06-07
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • 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, relatively harsh reaction conditions, the product Disadvantages such as not easy to separate, serious environmental pollution and non-reusable

Method used

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  • Method used for preparation of cyclized myrac aldehyde through catalytic selective cyclization of myrac aldehyde with supported molybdenum carbide
  • Method used for preparation of cyclized myrac aldehyde through catalytic selective cyclization of myrac aldehyde with supported molybdenum carbide
  • Method used for preparation of cyclized myrac aldehyde through catalytic selective cyclization of myrac aldehyde with supported molybdenum carbide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Mo 2 C / AC(Mo 2 C is molybdenum carbide, and AC is activated carbon) The specific preparation method is as follows:

[0017] Ammonium molybdate was dissolved in water so that the mass concentration of ammonium molybdate was 13.3mg / ml. Then, the solution was impregnated with activated carbon support (AC) by the method of equal volume impregnation. After oven drying at 120 °C for 12 h, the catalyst precursor was placed in H 2 The temperature-programmed carbothermal reaction was carried out in the atmosphere. The specific reaction process was as follows: 1.0g precursor was heated from room temperature to 400°C in a quartz reaction tube for 1h, then raised to 700°C at 1°C / min and kept for 1h for carbonization. The hydrogen flow rate was 60ml / min. A molybdenum carbide loading of 1 wt% Mo 2 C / AC catalyst.

[0018] Other conditions remain the same, only change the concentration of ammonium molybdate in the impregnating solution to obtain catalysts with different loadings ...

Embodiment 2

[0020] Molybdenum carbide was supported on alumina, silica, titania, zirconia, titania, silica-alumina molecular sieve, and phosphorus-aluminum molecular sieve to prepare supported molybdenum carbide catalyst Mo 2 C / B (B is a porous carrier, which is activated carbon, alumina, silica, zirconia, titania, silicon-aluminum molecular sieve, phosphorus-aluminum molecular sieve). The catalyst preparation process is similar to that of Example 1, except that the carriers are alumina, silica, zirconia, titania, silica-alumina molecular sieves, and phosphorus-aluminum molecular sieves. At the same time, the carbonization gas is changed from hydrogen to CH 4 / H 2 (Volume ratio 1:4), molybdenum carbide loading in the catalyst is 2wt%, thus obtaining six catalysts in which molybdenum carbide is loaded on alumina, silica, zirconia, titania, silica-alumina molecular sieve, and phosphorus-aluminum molecular sieve .

Embodiment 3-18

[0022] Mo 2 C / AC catalyzes the selective cyclization of para-citrus aldehyde to prepare cyclic citrus aldehyde: 5g para-citrus aldehyde, 50ml water, and Mo of a certain quality (see Table 1) 2 C / AC catalysts were added to the reactor respectively, replaced with nitrogen five times, the initial pressure of nitrogen was 0.1MPa, the temperature was controlled at 25°C, and the stirring reaction was carried out at a speed of 1000 rpm for 0.5-24h. Stand still for 10 minutes after the completion of the reaction, filter the supernatant and take a sample 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 Mo under different conditions 2 C / AC Catalyzed 4-(4-Methyl-3-pentenyl)-3-Cyclohexenal (P-Citral)

[0024] The results of the cyclization reaction to form 1,2,3,4,5,6,7,8-oct...

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Abstract

The invention relates to molybdenum carbide catalyzed myrac aldehyde cyclisation reaction, and more specifically relates to a method used for preparation of cyclized myrac aldehydes (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) through catalytic selective cyclization of myrac aldehydes (4-(4-methyl-3-pentenyl)-3-cyclohexene aldehyde (p-myrac aldehyde) and 3-(4-methyl-3-pentenyl)-3-cyclohexene aldehyde (m-myrac aldehyde)) with a supported molybdenum carbide catalyst under relatively mild conditions. According to the method, p-myrac aldehyde is taken as a raw material, in an organic solvent, at room temperature, production of 1, 2, 3, 4, 5, 6, 7, 8-octahydro-, 8, 8-dimethyl-2-naphthaldehyde through highselective cyclization reaction is realized; the highest substrate conversion rate is 100%, and the highest target product yield is 99%. Compared with conventional catalytic route, supported non-precious metal molybdenum carbide is taken as a catalyst, water is taken as reaction solvent, using of inorganic acid or base is not needed, and generation of a large amount of acid solution in conventional catalytic method is avoided; reaction conditions are mild, the catalyst is cheap, is high in activity and selectivity, and can be recycled, and the reaction process is friendly to the environment.

Description

technical field [0001] The invention relates to the preparation of citrus green aldehyde spices from the highly efficient catalytic reaction of citrus green aldehydes, specifically a method utilizing loaded non-precious metal molybdenum carbide (Mo 2 C) A method of replacing traditional liquid acid catalysts to catalyze the efficient conversion of citrus aldehydes to prepare ring citrus aldehydes. Background technique [0002] Citrus green aldehyde, also known as Merlot, includes two isomers ( figure 1 ), the full names are 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. These two isomers have a pleasant woody fragrance and a complex herbal fragrance respectively. They are necessary intermediates for the synthesis of various valuable spices and are widely used in fields such as perfumes and cosmetics (see literature: a) Ohloff, G. Riechstoffe Aromen 1957, 38-40. b) Ohloff, G. DE 1057108, 1957, Dragoco ...

Claims

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Application Information

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IPC IPC(8): C07C45/67C07C47/445B01J27/22B01J29/85B01J29/076
Inventor 李昌志李新新王爱琴张涛
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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