Method for preparing dialdehyde substance employing environment-friendly efficient oxidation of annular ortho diol and device required for realizing method

A technology of ortho diol and dialdehyde, which is applied in the field of fine chemical synthesis and green chemical preparation, can solve the problems of low electrolysis efficiency, high energy consumption, and low yield, and achieve simple procedures, low energy consumption, and high yield high effect

Inactive Publication Date: 2015-04-08
BEIJING UNIV OF CHEM TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the cost of traditional oxidants is high, the production process is complicated, the yield is low, and they cannot be reused, such as ozone oxidation, iodobenzene diacetate oxidation, hydrogen peroxide-catalyst system oxidation, sodium periodate-catalyst system oxidation and high Sodium iodate-silica gel oxidation system oxidation method, etc.
However, the ozone corrosive equipment in the ozone oxidation method needs to add other reducing reagents in addition to avoid excessive oxidation to make the aldehyde generate acid, thus increasing the separation difficulty of the product and reducing the product yield; although the iodobenzene diacetate oxidation method produces Higher efficiency and mild conditions, but the oxidant itself is not easy to obtain; in the hydrogen peroxide-catalyst oxidation method, although hydrogen peroxide is a green oxidant, the yield of aldehydes is reduced due to the poor selectivity of hydrogen peroxide
Compared with several other catalytic oxidants, the periodic acid oxidation system has a higher yield of dialdehyde generated by breaking the carbon chain when oxidizing the cyclic ortho-diol, but the price of sodium periodate is also relatively the highest. There is no literature and process research explanation at present. Aldehydes can be produced by recycling periodate oxidation
In addition, it has been reported to use electrochemical methods to directly oxidize cyclic ortho-diols to break and open the ring to prepare dialdehydes, but the reaction selectivity is poor and excessive redox reactions are prone to occur: the content of by-products of acids and alcohols is high And electrolysis efficiency is low, energy consumption is high

Method used

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  • Method for preparing dialdehyde substance employing environment-friendly efficient oxidation of annular ortho diol and device required for realizing method
  • Method for preparing dialdehyde substance employing environment-friendly efficient oxidation of annular ortho diol and device required for realizing method
  • Method for preparing dialdehyde substance employing environment-friendly efficient oxidation of annular ortho diol and device required for realizing method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Such as figure 2 In the shown reaction device, 10 g of 1,2-cyclohexanediol, 20 mL of dichloromethane, and the ground oxidant system (10 g of sodium periodate: 10 g of silicon dioxide = 1:1, wherein the silicon dioxide is 300 mesh ) into the reactor, keep the temperature at 38°C, and stir at 600r / min, so that sodium periodate is highly dispersed in the reaction system, and then reflux dichloromethane for 2h. After the reaction is finished, the solids of the solution and the oxidant-containing system are separated by filtration. After the filtrate was distilled under reduced pressure, it was detected by gas chromatography-mass spectrometer that the purity of adipaldehyde reached 99.8%, the mass of adipaldehyde was 9.82g, and the yield was 99.72%.

[0072] Add 100g of water to dissolve the solids in the oxidant-containing system to obtain a mixture of sodium periodate, sodium iodate and silicon dioxide, filter the water-insoluble silicon dioxide and dry it to enter the n...

Embodiment 2

[0074] Such as figure 2 In the reaction device shown, 10g of 1,2-cyclohexanediol, 30mL of 1,2-dichloroethane, and the oxidant system after grinding (15g of potassium periodate: 30g of silicon dioxide = 1:2, where two Silicon oxide (600 mesh) was added into the reactor, the temperature was kept at 82°C, and stirring was performed at 150 r / min to make potassium periodate highly dispersed in the reaction system, and 1,2-dichloroethane was refluxed for 2 hours. After the reaction is finished, the solids of the solution and the oxidant-containing system are separated by filtration. After the filtrate was distilled under reduced pressure, it was detected by gas chromatography-mass spectrometer that the purity of adipaldehyde reached 99.7%, the mass of adipaldehyde was 14.7g, and the yield was 99.92%.

[0075] Add 100g of aqueous solution to dissolve the solid oxidant to obtain a mixture of potassium periodate, potassium iodate and silicon dioxide, filter the water-insoluble silico...

Embodiment 3

[0077] Add 20g of 1,2-cyclopentanediol, 30mL of ethyl acetate, and the ground oxidant system (sodium periodate 20g, without carrier) into the reactor, keep the temperature at 75°C, and stir at 300r / min to make the sodium periodate Highly dispersed in the reaction system, reflux ethyl acetate reaction for 5h. After the reaction is finished, the solids of the solution and the oxidant-containing system are separated by filtration. After the filtrate was distilled under reduced pressure, it was detected by gas chromatography-mass spectrometer that the glutaraldehyde had a purity of 99.8%, a mass of 19.61 g, and a yield of 99.97%.

[0078] Add 150g of 1M aqueous sodium hydroxide solution to dissolve the solid oxidizing agent to obtain a mixture of sodium periodate and sodium iodate, and enter the next cycle for subsequent use. Pour the aqueous solution containing sodium periodate and sodium iodate into the electrolytic cell. Add 100g / L NaCl and 0.5M HCl solution to the electrolyt...

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Abstract

The invention relates to a method for preparing a dialdehyde compound employing periodate regenerated by an electrochemical method for cyclically and lastingly oxidizing annular ortho diol in a closed system, and relates to electrolytic regeneration and recycling processes of expensive periodate. The method has the advantages that the dialdehyde substance is high in yield, high in purity and high in production efficiency; the periodate and an organic solvent are circulated in the overall flow, so that the production cost is reduced; no pollution is generated; and a reactor and an electrolytic bath are simple in structure, so that a gas is not required, the material consumption is low, and energy consumption is low.

Description

technical field [0001] The invention belongs to the technical field of fine chemical synthesis and green chemical preparation. Specifically, the present invention relates to a method for regenerating periodate by an electrochemical method to continuously oxidize cyclic ortho-diols in a closed system to produce dialdehydes. The method is simple in process, low in cost, high in yield, low in material consumption, low in energy consumption, does not generate industrial three wastes, and can realize the recycling of the oxidizing agent. Background technique [0002] In the prior art, there are methods for preparing dialdehydes by oxidation of cyclic ortho diols using existing oxidizing agents. However, the cost of traditional oxidants is high, the production process is complicated, the yield is low, and they cannot be reused, such as ozone oxidation, iodobenzene diacetate oxidation, hydrogen peroxide-catalyst system oxidation, sodium periodate-catalyst system oxidation and high...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C47/12C07C45/29C01B11/22C25B1/24
CPCC07C45/29C07C45/78C25B1/24C07C47/12
Inventor 万平玉张英伟孔丹丹张新志陈咏梅魏小林唐阳庞伟伟孟晓冬曹晓雅印文雅
Owner BEIJING UNIV OF CHEM TECH
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