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Method for realizing one-step synthesis of carvone through catalytic oxidation

A technology for catalytic oxidation and carvone, which is applied in the oxidation preparation of carbonyl compounds, organic chemistry, etc., can solve the problems of low conversion rate, environmental pollution, low selectivity, etc., and achieves high conversion rate, abundant resources and good selectivity. Effect

Inactive Publication Date: 2015-03-25
NANJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Although the process has high yield and low cost, a large amount of a-terpin oil and hydroxycarvone will be generated in the process, and the industrial wastewater contains carcinogenic acetone oxime and a large amount of sulfate effluent. serious pollution
Chinese patent CN1092402A discloses an improved method of this process, which improves the yield, makes the solvent easy to recover, and is more conducive to the use in industrial production, but it cannot completely solve the problem of serious environmental pollution
However, these methods all have problems such as low conversion rate, low selectivity, and serious pollution.

Method used

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  • Method for realizing one-step synthesis of carvone through catalytic oxidation
  • Method for realizing one-step synthesis of carvone through catalytic oxidation
  • Method for realizing one-step synthesis of carvone through catalytic oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Weigh 2.5 g V 2 o 5 , add the calculated amount of metal component precursor AgNO according to n (Ag) / n (V) =0.1 3 , placed in 40 mL of isobutanol, refluxed at 120°C for 12 h, then added H 3 PO 4 , continued to reflux at 110°C for 6 h, the obtained precipitate was filtered and washed with deionized water until neutral, dried in air at 110°C for 12 h, and then calcined in air at 400°C for 4 h to obtain dark green Ag- VPO catalyst.

[0026] Add 0.02 g of the above catalyst, 5 mL of acetonitrile, 0.5 mL of limonene and 2 mL of tert-butyl hydroperoxide into a 100 mL round bottom flask, heat in a constant temperature oil bath at 82 °C, magnetically stir at 650 r / min, and reflux for 10 h under condensation. Sampling after the reaction, analyzed by gas chromatography, showed that the conversion rate of limonene was 84.3%, the selectivity of carvone was 25.2%, and the selectivity of carveol / epoxidized limonene was 30%.

Embodiment 2

[0028] Catalyst preparation, the synthesis method of carvone, the amount of feed, and the reaction conditions are basically the same as in Example 1, except that the amount of limonene added is 0.75 mL. At this time, the conversion rate of limonene is 68.3%. Carvone The selectivity is 22.8%.

Embodiment 3

[0030] Weigh 2.5g V 2 o 5 , add the calculated amount of metal component precursor ZrOCl according to n (Zr) / n (V) =0.1 2 ·8H 2 O, placed in 40 mL of isobutanol, refluxed at 120°C for 12 h, then added H 3 PO 4 , continue to reflux at 110°C for 6 h, filter and wash the obtained precipitate with deionized water until neutral, and dry in air at 110°C for 12 h; then roast at 400°C in air for 4 h to obtain dark green Zr- VPO catalyst.

[0031] Using the prepared Zr-VPO as a catalyst, catalytic oxidation is used to synthesize carvone. The reaction conditions are the same as in Example 1. After the reaction, samples are taken, and analyzed by gas chromatography. The conversion rate of limonene is 88.9%, and the selectivity of carvone is 30.0%. , the selectivity of carveol / epoxidized limonene was 31.5%.

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Abstract

The invention discloses a one-step synthesis method of carvone through catalytic oxidation, belonging to the field of catalytic oxidation and organic synthesis. According to the method, limonene serving as a raw material is oxidized by tert-butyl hydroperoxide in the presence of a metal modified vanadium phosphorus oxide catalyst, thus obtaining the carvone product in one step. Under the optimized reaction condition, the limonene conversion rate is higher than 80 percent, the yield of carvone is 30 percent, the total effective yield of carvone / carveol / epoxidated limonene can be 60 percent, and the results are superior to reported values. According to the carvone preparation method disclosed by the invention, the problems such as low conversion rate, low selectivity and severe pollution existing in the conventional methods are solved.

Description

technical field [0001] The invention relates to a method for preparing carvone, in particular to a method for preparing carvone by catalyzing the oxidation of limonene, which belongs to the technical field of organic synthesis. Background technique [0002] Carvone is also called spearmint oil and 1-carvone, and its system name is 2,3-dimethyl-5-isopropenyl-cyclohexanone, and its English name is Carvone. Carvone is the main component of spearmint oil, and its content is about 50%~60%. It has a strong, fresh, penetrating, and hearty spearmint aroma, and is widely used in toothpaste, candy, beverages, soaps and other industries. Naturally extracted carvone has low yield, high cost, complicated process, and is also affected by many factors such as climate and geography. With the development of the carvone application industry, the natural extraction of carvone is far from meeting the needs of the market, so the artificial synthesis of carvone has been developed rapidly. [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/647C07C45/28
CPCC07C45/28C07C2601/16C07C49/647
Inventor 刘俊华张谨
Owner NANJING NORMAL UNIVERSITY
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