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Preparation method of 1,2-cyclohexanedione

A technology of cyclohexanedione and cyclohexanone, which is applied in the field of preparation of 1,2-cyclohexanedione, can solve problems such as complex operation steps and unsuitability for large-scale production

Pending Publication Date: 2022-01-11
八叶草健康产业研究院厦门有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this method, the intermediate cyclic ketoxime is filtered from the nitrosation reaction system and then hydrolyzed, the operation steps are complicated, and it is not suitable for large-scale production

Method used

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  • Preparation method of 1,2-cyclohexanedione
  • Preparation method of 1,2-cyclohexanedione
  • Preparation method of 1,2-cyclohexanedione

Examples

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preparation example Construction

[0021] The invention provides a kind of preparation method of 1,2-cyclohexanedione, comprising the following steps:

[0022] Mix cyclohexanone, hydrochloric acid and isoamyl nitrite for an oxime-forming reaction to obtain an oxime-forming reaction liquid, adjust the pH value of the oxime-forming reaction liquid ≥ 7, and prepare the oxime-forming reaction liquid with a pH value ≥ 7, water-soluble Nitrite and sulfuric acid are mixed to carry out oxidative hydrolysis reaction to obtain the 1,2-cyclohexanedione, the mass percentage of the hydrochloric acid is ≥35%, and the mass percentage of the sulfuric acid is ≤30%.

[0023] In the present invention, unless otherwise specified, the raw materials used are commercially available products well known to those skilled in the art.

[0024] In the invention, cyclohexanone, hydrochloric acid and isoamyl nitrite are mixed for an oxime forming reaction to obtain an oxime forming reaction liquid.

[0025] In the present invention, the mas...

Embodiment 1

[0054] React according to the equation shown in formula II:

[0055]

[0056] Add 10g of cyclohexanone to the reaction bottle, add 0.5g of 37% concentrated hydrochloric acid dropwise under ice bath conditions, then add 12g of isoamyl nitrite dropwise, carry out oxime formation reaction at 0°C under ice water bath conditions for 4h, and form oxime After the reaction, the pH of the oxime reaction solution was adjusted to 7.4. Then add 100mL of ice water and 10g of sodium nitrite to the reaction flask, and add 15g of 30% dilute H 2 SO 4 Solution, heated to 40°C for oxidative hydrolysis reaction. After the oxidative hydrolysis reaction is finished, the oxidative hydrolysis reaction solution and saturated sodium carbonate solution are mixed and washed (volume ratio is 1:1), after washing, the hydrolysis reaction solution is extracted 3 times with ethyl acetate (volume ratio is 1:1), and the combined After extracting the organic phase, dry it with anhydrous sodium sulfate (the...

Embodiment 2

[0060] React according to the equation shown in formula II:

[0061]

[0062] Add 15g of cyclohexanone to the reaction flask, add 0.36g of 37% concentrated hydrochloric acid dropwise under ice bath conditions, then add 18g of isoamyl nitrite dropwise, carry out oxime formation reaction at 0°C under ice water bath conditions for 4h, and form oxime After the reaction, the pH of the oxime reaction solution was adjusted to be 7. Then add 100mL of ice water and 15g of sodium nitrite to the reaction flask, and add 20g of 30% dilute H 2 SO 4 Solution, heated to 40°C for oxidative hydrolysis reaction. After the oxidative hydrolysis reaction is finished, the oxidative hydrolysis reaction solution and saturated sodium carbonate solution are mixed and washed (volume ratio is 1:1), after washing, the hydrolysis reaction solution is extracted 3 times with ethyl acetate (volume ratio is 1:1), and the combined After extracting the organic phase, dry it with anhydrous sodium sulfate (th...

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Abstract

The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of 1,2-cyclohexanedione. The preparation method provided by the invention comprises the following steps: mixing cyclohexanone, hydrochloric acid and isoamyl nitrite, and carrying out oxime forming reaction to obtain oxime forming reaction liquid; regulating the pH value of the oxime forming reaction liquid to be larger than or equal to 7, blending the oxime forming reaction liquid with the pH value larger than or equal to 7, water-soluble nitrite and sulfuric acid for an oxidation hydrolysis reaction so as to obtain the 1,2-cyclohexanedione, wherein the mass percent of the hydrochloric acid is greater than or equal to 35%, and the mass percent of the sulfuric acid is less than or equal to 30%. The preparation method provided by the invention does not need alcohol removal and filtration to obtain an intermediate. The pH value of the oxime reaction liquid is directly adjusted to be larger than or equal to 7, and the oxime reaction liquid is mixed with water-soluble nitrite and sulfuric acid to be subjected to oxidative hydrolysis reaction to obtain the target product 1,2-cyclohexanedione. The 1,2-cyclohexanedione is successfully prepared by adopting a one-pot method, and the steps are simple; besides, the yield of the 1,2-cyclohexanedione is high, and the process is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a preparation method of 1,2-cyclohexanedione. Background technique [0002] 1,2-Cyclohexanedione is a chemical raw material with burnt-sweet aroma. It can not only be used in the synthesis of perfumes, but also be used as an intermediate in the synthesis of some heterocyclic compounds. [0003] Cyclohexanone oxidation is a classic method for preparing 1,2-cyclohexanedione, and it is also the only method that can be used in industrial production. The method uses selenium dioxide at an equivalent level as an oxidant, and the yield is usually between 30% and 50%. Due to the high price of selenium dioxide, the cost of 1,2-cyclohexanedione produced by this method is expensive, exceeding 2,000 yuan / kg; moreover, selenium dioxide has a toxicity equivalent to that of arsenic, and the selenium residue produced after the reaction is difficult to handle , will cause serious env...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/42C07C49/403
CPCC07C45/42C07C249/10C07C2601/14C07C251/44C07C49/403
Inventor 汤须崇赵应伟谢清萍曹丽平
Owner 八叶草健康产业研究院厦门有限公司
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