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Synthesis method of oxo-isophorone

A technology of oxyisophorone and synthesis method, which is applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve problems such as high cost of reaction process and dangerous operating conditions, and achieve process friendly, The effect of less discharge of three wastes and improvement of the utilization rate of raw material molecules

Active Publication Date: 2019-03-12
SHANGYU NHU BIOCHEM IND +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the method has a high yield, the reaction process cost is high, and the operating conditions are very dangerous

Method used

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  • Synthesis method of oxo-isophorone
  • Synthesis method of oxo-isophorone
  • Synthesis method of oxo-isophorone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] 1) Add industrial product HIP equivalent to 30.0g (0.1945mol) of pure HIP, 60.0g toluene into a four-neck flask, heat up to 80°C under 300rpm stirring condition, blow air through bubbling method, and add 10.8g p-benzoquinone dropwise (0.10mol) + toluene 30.0g mixed solution, after the dropwise addition, keep the temperature at 80±10°C, continue to ventilate the air, react for 2-5 hours, GC detects that the HIP residue < 0.1% stops the reaction;

[0049] 2) Add aqueous sodium thiosulfate solution (100ml, mass concentration 15-20%) to the reaction solution in step 1) and stir for 30min, then add (in two times, 50mL each time) 5% sodium hydroxide solution for washing, after layering , the aqueous phase is an alkali washing solution, and the organic phase is washed with 30ml of water as a reaction solution,

[0050] 3) In a four-neck flask, stir and feed in air at 70-80°C, react for 2-3 hours, add 30g of toluene and stir for 10min, cool down to room temperature, let stand, ...

Embodiment 2

[0053] 1) Add the industrial product HIP (0.2075mol) equivalent to 32.0g of pure HIP, 60.0g toluene, and heat up to 80°C under 300rpm stirring conditions in a four-necked flask, and add trimethylbenzoquinone dropwise with air by bubbling method 15.0g (0.10mol) + toluene 45.0g mixed solution, after the dropwise addition, keep the temperature at 80±10°C, continue to ventilate the air, react for 3-5 hours, GC detects that the HIP residue < 0.1% stops the reaction;

[0054] 2) Add aqueous sodium thiosulfate solution (100ml, mass concentration 15-20%) to the reaction solution in step 1) and stir for 30min, then add (twice, 70ml each) 5% sodium hydroxide solution for washing, after layering , the aqueous phase is an alkali washing solution, and the organic phase is used as a reaction solution after washing with 50ml of water;

[0055] 3) In a four-neck flask, stir and feed in air at 70-80°C, react for 2-3 hours, add 35g of toluene and stir for 10 minutes, cool down to room temperatu...

Embodiment 3

[0058] 1) Add industrial product HIP equivalent to 35.0g (0.2270mol) of pure HIP, 65.0g p-xylene into a four-necked flask, heat up to 100°C under 300rpm stirring condition, air-bubble method, drop trimethyl Benzoquinone 20.0g (0.1333mol) + p-xylene 45.0g mixed solution, after the dropwise addition, keep the temperature at 100±10°C, continue to ventilate the air, react for 3-5 hours, GC detects that the HIP residue < 0.1% stops the reaction,

[0059] 2) Add aqueous sodium thiosulfate solution (100ml, mass concentration 15-20%) to the reaction solution in step 1) and stir for 30min, then add (twice, 70mL each) 5% sodium hydroxide solution for washing, after layering , the aqueous phase is an alkali washing solution, and the organic phase is washed with 50ml of water as a reaction solution,

[0060] 3) In a four-neck flask, stir and feed in air at 70-80°C, react for 2-3 hours, add 35g of p-xylene and stir for 10min, drop to room temperature, let stand, and separate the organic ph...

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Abstract

The invention relates to a synthesis method of oxo-isophorone. The method is characterized in that 3, 5, 5-trimethyl-4-hydroxyl-2-cyclohexene-1-one (HIP) is used as a raw material, p-benzoquinone compounds (II) are used as an oxidizing agent and a catalyst; oxygen or air is introduced, and an oxidation reaction is carried out in an inert solvent, so that the oxo-isophorone (KIP) and hydroquinone compounds (III) are generated.

Description

technical field [0001] The invention relates to the field of fine chemicals, in particular to an oxoisophor with 3,5,5-trimethyl-4-hydroxy-2-cyclohexen-1-one (hereinafter referred to as HIP) as the starting material Synthesis of ketones. Background technique [0002] Oxyisophorone (2,6,6-trimethyl-2-cyclohexene-1,4-dione, 4-Ketoisophorone, referred to as KIP, CAS: 1125-21-9) is a synthetic biotin Key intermediate, its structural formula is as follows: [0003] [0004] The preparation method of oxyisophorone is generally that β-isophorone is used as a raw material, and then oxidized into oxoisophorone. Its existing routine synthetic route is as follows:, [0005] [0006] The above route uses β-isophorone (3,5,5-trimethylcyclohex-3-en-1-one, β-Isophorone, referred to as β-IP, CAS: 78-59-1) as raw material, Obtained by oxidation, in the reaction, oxoisophorone (KIP) as the product and 3,5,5-trimethyl-4-hydroxyl-2-cyclohexen-1-one ( HIP) and 3-formyl-5,5-dimethyl-2-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/37C07C49/603C07C45/78
CPCC07C45/37C07C45/78C07C49/603
Inventor 杭姣夏小忠李伟明刘祥洪曾庆宇毛建拥乔胜超
Owner SHANGYU NHU BIOCHEM IND
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