Preparation method of 1,3-cyclohexanedione

A technology of cyclohexanedione and resorcinol, which is applied in the field of recovery of high-purity 1,3-cyclohexanedione preparation, can solve problems such as unsolved problems, low product yield, and 1,3-cyclohexanedione efficiency. and low recovery rate, to achieve the effect of easy operation and low organic matter content

Pending Publication Date: 2020-06-19
NUTRICHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patents such as CN2005100489576.X, CN201110419160.6, JP0413644, JP20013421632001 etc. report that the choice of catalyst has a great influence on product selectivity and yield; low rate
But above-mentioned method all does not solve the problem that the efficiency and recovery rate of 1,3-cyclohexanedione are lower in the acidification mother liquor

Method used

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  • Preparation method of 1,3-cyclohexanedione
  • Preparation method of 1,3-cyclohexanedione
  • Preparation method of 1,3-cyclohexanedione

Examples

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preparation example Construction

[0036] The preparation method that the present invention provides 1,3-cyclohexanedione comprises the steps:

[0037] (1) In the presence of water, resorcinol is hydrogenated to obtain a reaction solution containing a compound represented by the following formula (1), and the reaction solution is acidified to obtain 1,3-cyclohexanedione acidified solution, Then crystallize the 1,3-cyclohexanedione acidified solution to obtain 1,3-cyclohexanedione product and acidified mother liquor containing 1,3-cyclohexanedione,

[0038]

[0039] (2) In the presence of an organic solvent, the acidified mother liquor containing 1,3-cyclohexanedione is contacted with a complexing agent, so that 1,3-cyclohexanedione is complexed with the complexing agent, and Obtain the organic phase;

[0040] (3) contacting the organic phase obtained in step (2) with the reaction solution, and adjusting the pH to 7-14, so that 1,3-cyclohexanedione and the complexing agent are dissociated, and an aqueous pha...

Embodiment 1

[0069] (1) hydrogenation, acidification and crystallization

[0070] Resorcinol (99%, 0.535mol) is neutralized with aqueous sodium hydroxide solution (15%, 0.589mol), and then hydrogenated at 5MPa and 120°C to obtain the formula The reaction solution of the compound shown (30%, 0.535mol), and the reaction solution was acidified with hydrochloric acid (30%, 0.562mol) at 15-20°C to obtain 1,3-cyclohexanedione acidified solution , and then cool down the 1,3-cyclohexanedione acidification solution to crystallize at 5°C and filter and dry to obtain 1,3-cyclohexanedione product (99%, 0.426mol) and 1,3-cyclohexanedione acidified mother liquor.

[0071] (2) Extraction of 1,3-cyclohexanedione

[0072] The first extraction: at room temperature, add 75g of trioctylamine (i.e. tri-n-octylamine) and 125g of kerosene to a 1L reaction bottle to obtain a mixed solution of complexing agent, and add the 1 obtained in step (1) under stirring. The acidified mother liquor of 3-cyclohexanedione...

Embodiment 2

[0080] Prepare 1,3-cyclohexanedione according to the method of Example 1, the difference is that in step (2), the first extraction uses the upper trioctylamine kerosene phase extracted for the second time in Example 1, and the second extraction The upper trioctylamine kerosene phase extracted for the third time in Example 1 was used for extraction.

[0081] The 1,3-cyclohexanedione product (99.4%, 0.519 mol) was finally obtained with a yield of 96.43%.

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Abstract

The invention relates to the field of organic synthesis, and discloses a preparation method of 1,3-cyclohexanedione. The method comprises the following steps: 1, in the presence of water, hydrogenating resorcinol to obtain a reaction solution containing a compound represented by the following formula (1), acidifying the reaction solution to obtain an acidified solution, and crystallizing the acidified solution to obtain a 1,3-cyclohexanedione product and an acidified mother liquor; 2, in the presence of an organic solvent, enabling the acidified mother liquor to be in contact with a complexingagent to complex 1,3-cyclohexanedione with the complexing agent, and obtaining an organic phase; 3, making the organic phase obtained in the step 2 contact the reaction solution, adjusting the pH value to 7-14 so as to make the 1,3-cyclohexanedione be dissociated from the complexing agent, and obtaining a water phase; and 4, adjusting the pH value of the water phase obtained in the step 3 to 1.0-2.5, and carrying out solid-liquid separation to obtain the 1,3-cyclohexanedione product. The preparation method disclosed by the invention has the advantages of high purity and high yield of the prepared 1,3-cyclohexanedione.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method for recovering high-purity 1,3-cyclohexanedione from acidified mother liquor of 1,3-cyclohexanedione. Background technique [0002] 1,3-cyclohexanedione is used as an intermediate for organic synthesis, and can be used for the synthesis of various organic compounds such as material monomers, curing agents, solvents, etc. It is an intermediate for herbicides sulcotrione and mesotrione. [0003] In the existing 1,3-cyclohexanedione preparation method, resorcinol is usually used as a starting material, hydrogenation reduction, acidification, recrystallization to obtain 1,3-cyclohexanedione product, and its preparation route as follows. [0004] [0005] At present, there is no report at home and abroad to recover high-purity 1,3-cyclohexanedione product from acidified mother liquor water. Patents such as CN2005100489576.X, CN201110419160.6, JP0413644, JP200...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/00C07C45/81C07C49/403
CPCC07C45/00C07C45/81C07C45/006C07C2601/14C07C2601/16C07C49/403C07C49/713
Inventor 倪肖元王磊吴坤李辛夷
Owner NUTRICHEM LAB CO LTD
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