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Process of synthesizing 1,4-cyclohexyl dione

A technology of cyclohexanedione and a synthesis method, which is applied in the field of chemical synthesis, can solve problems such as environmental pollution, and achieve the effects of easy availability of raw materials, high product yield and low cost of raw materials

Inactive Publication Date: 2007-08-22
HEBEI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to solve the problem that a large amount of toxic chemical oxidants or organic solvents are used in the existing 1,4-cyclohexanedione production process to easily pollute the environment, and to provide a new environmentally friendly 1,4-cyclohexanedione Method for preparing diketone, simultaneously improving product yield and reducing production cost

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] A. Add 16g NaOH and 60ml water into a 200ml beaker equipped with a stirrer and a thermometer, cool to 50°C under vigorous stirring, and add 12.5g nickel-aluminum alloy (Jinan Xinhaitong Special Alloy Co., Ltd.) to it in small amounts under stirring . Adjust the alloy addition rate to keep the solution temperature at 50±2°C. After the addition, react in a water bath at 50±2° C. for one hour under slow stirring, and then wash with water and alcohol several times to obtain a skeleton nickel catalyst.

[0027] B. Take 56g of hydroquinone and 6g of the skeleton nickel catalyst prepared above, put them into the autoclave together with 250ml of water, then add 1ml of 50% NaOH solution, then fill it with hydrogen pressure of 1.5MPa, and react at 200°C for 3 hours , After the reaction is finished, the skeleton nickel catalyst is first filtered to recover and used mechanically. After the reaction liquid is distilled to remove water, the product 1,4-cyclohexanediol is obtained wi...

Embodiment 2

[0030] A, with embodiment 1

[0031] B. Take 56g of hydroquinone and 6g of the skeleton nickel catalyst prepared above, put them into the autoclave together with 250ml of water, then add 1ml of 50% NaOH solution, then fill it with hydrogen pressure of 1.2MPa, and react at 150°C for 3 hours , After the reaction is finished, the skeleton nickel catalyst is first filtered to be recovered and used mechanically, and the reaction solution is distilled to remove water to obtain the product 1,4-cyclohexanediol with a yield of 90%.

[0032] C1. First add 0.66g of sodium tungstate, 0.25g of oxalic acid and 30ml of hydrogen peroxide into the three-necked bottle, stir for 5 minutes, then add 11.6g of 1,4-cyclohexanediol into the three-necked bottle, and set the temperature to 80°C. After 24 hours of reaction, the product 1,4-cyclohexanedione was obtained by distillation with a yield of 78%.

Embodiment 3

[0034] A, with embodiment 1

[0035] B, get 56g hydroquinone and the 5.8g skeleton nickel catalyst that reclaims after the B step reaction in embodiment 2 and the 0.3g skeleton nickel catalyst newly prepared of A step, add in the autoclave together with 250ml water, add 50% NaOH solution 1ml, then filled with hydrogen pressure 1.8MPa, reacted at 180°C for 5 hours, filtered to remove the skeleton nickel catalyst for recycling after the reaction was completed, and the product 1,4-cyclohexanediol was obtained after the reaction liquid was distilled to remove water , yield 93%.

[0036] C1. First add 0.6g of quaternary ammonium decapolytungstate and 11.6g of 1,4-cyclohexanediol into a 250ml three-necked flask, then slowly add 60ml of hydrogen peroxide dropwise into the reaction flask under ice bath and stirring , reacted for 12 hours under stirring, and distilled to obtain the product 1,4-cyclohexanedione with a yield of 79%.

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Abstract

The present invention relates to environment friendly process of synthesizing 1, 4-cyclohexyl dione. The process includes the following steps: 1. preparing skeleton nickel catalyst; 2. preparing 1, 4-cyclohexyl diol with hydroquinone as material and through catalytic hydrogenation under the action of the skeleton nickel catalyst in a high pressure reactor; and 3. oxidizing with hydrogen peroxide or catalytic dehydrogenation to prepare 1, 4-cyclohexyl dione. The present invention is significant in industrial production of 1, 4-cyclohexyl dione, and has the advantages of easy-to-control mild reaction, low cost, environment friendship, easy-to-prepare catalyst with high stability and reusability, and high product yield.

Description

technical field [0001] The invention relates to an environment-friendly synthesis method of 1,4-cyclohexanedione, which belongs to the technical field of chemical synthesis. Background technique [0002] A method of preparing 1,4-cyclohexanedione with hydroquinone as raw material reported in the literature is that hydroquinone is first catalytically hydrogenated in water or alcohol solution to generate 1,4-cyclohexanediol, the latter In acetone or acetic acid solution, it is oxidized by chromic acid, bromate, hydrogen peroxide, oxygen, etc. to produce 1,4-cyclohexanedione product. For example, RObertJ. proposed to carry out catalytic hydrogenation in alkaline 50% hydroquinone aqueous solution, using skeleton nickel as a catalyst, and after separation of intermediates, in RuCl 3 Under the catalyst, 1,4-cyclohexanedione can be obtained by oxidation with sodium hypochlorite. In addition, patent DE19541262 has reported the method for producing 1,4-cyclohexanedione by one-step ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/403C07C45/39
Inventor 白国义宁慧森张晨芳彭洪伟
Owner HEBEI UNIVERSITY
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