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Process for preparing 3-hydroxyglutarate compound

A technology of hydroxyglutarate and oxoglutarate, which is applied in the field of preparation of ester compounds, can solve the problems of high price, hydrogen cannot be used in production, and increased difficulty

Inactive Publication Date: 2008-03-19
河南豫辰药业股份有限公司
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  • Abstract
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  • Claims
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Problems solved by technology

This method has the serious shortcoming of following aspects: 1, sodium borohydride or lithium aluminum hydride are more expensive; Requirements; 3. The yield is low; 4. The solvent used in the reaction is alcohols such as ethanol and methanol, which increases the difficulty of separating the salt impurities of sodium, aluminum and lithium that are finally generated by the reducing agent; 5. The amount of three wastes is large
Under such a high pressure, there are extremely high requirements on the equipment and the gas source, which is not suitable for fine chemical scale production, because the conventional gas source is only 130atm, so a large amount of hydrogen cannot be used Production, and it is extremely dangerous to discharge so much hydrogen when reloading hydrogen

Method used

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  • Process for preparing 3-hydroxyglutarate compound
  • Process for preparing 3-hydroxyglutarate compound

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preparation example Construction

[0012] The preparation method provided by the invention is carried out in a reactor. Under lower pressure, the reaction pressure is 0.1-3Mpa, especially preferably 0.5-1Mpa.

[0013] The catalyst suitable for this method is highly active nickel or palladium-carbon catalyst, palladium-carbon or high-activity nickel containing 5%-20% of palladium is more effective, preferably high-activity nickel catalysis.

[0014] The ester solvents suitable for this method can be selected from one or more mixed solvents such as esters, saturated hydrocarbons or saturated halogenated hydrocarbons, alcohols, etc., wherein lower esters such as ethyl acetate, methyl acetate, ethyl formate, methyl formate and Lower alcohols such as methanol and ethanol are more effective, and the preferred solvent is lower aliphatic esters, especially ethyl acetate.

[0015] The reaction temperature suitable for this process is 20-120°C, particularly preferably 60-90°C.

[0016] The reaction time suitable for th...

Embodiment 1

[0024] 400kg of ethyl acetate, 150kg of diethyl acetone dicarboxylate and 25kg of highly active nickel treated with sodium hydroxide-ethanol were put into a high-pressure reactor under the protection of nitrogen, and the hydrogen pressure was raised to 0.4Mpa after the nitrogen was replaced by hydrogen. Close the hydrogen gas inlet valve, heat to 50°C under stirring, turn on the hydrogen gas when the pressure drops, turn off the heating, and feed hydrogen gas to the pressure of 0.8Mpa under natural cooling, calculate the amount of hydrogen gas to be fed, and turn on when the temperature naturally rises to 65°C Circulating water cools the reactor so that the temperature is controlled at 65-85°C, and the amount of hydrogen inhaled reaches the calculated amount within about 2-1 hours. The pressure in the constant temperature reactor does not drop any more, and then keeps stirring for 0.5 hours to terminate the reaction. Replace the hydrogen in the kettle with nitrogen, release the...

Embodiment 2

[0026] The above diethyl acetone dicarboxylate was changed to dimethyl acetone dicarboxylate, and the same operation method was adopted, and the result obtained was detected by GC, and dimethyl acetone dicarboxylate was 0.7%, and the weight was 150.8 kg.

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Abstract

The invention discloses a method which utilizes a 3-oxo glutarate ester compound to prepare a 3-hydroxyl glutarate ester compound. Under the conditions of pressure between 0.1 to 3 MPa and temperature between 20 DEG C and 120 DEG C, the 3-oxo glutarate ester compound catalyzed by nickel or palladium catalyzer in ester solvent is heated for half to twenty four hours in a reaction kettle, so that the 3-oxo glutarate ester compound in the class of 3-acetone dicarboxylic acid dimethyl ester (diethyl ester) is hydrogenated and reduced, thus preparing the 3-hydroxyl glutarate ester compound in the class of 3-hydroxyl glutarate dimethyl ester (diethyl ester). The method is carried out under a low perssure, as a result, high pressure is avoided, the requirements on devices is low, and the method can adapt to the fine chemical-scale production. Meanwhile, under the pressure, the use of hydrogen is convenient, safe and economical. The yield rate is high, almost reaching one hundred percent.

Description

technical field [0001] The invention relates to a method for preparing ester compounds, in particular to a method for preparing 3-hydroxyglutarate compounds from 3-oxoglutarate. Background technique [0002] 3-Hydroxyglutarate is a prochiral compound, which can be made into a class of important biologically active chiral compounds by derivatizing its two ester functional groups or carboxyl groups. It is currently used in medicine, pesticides, spices and food additives There are applications in China, especially in blood lipid-lowering drugs. Its structural general formula is as follows: [0003] [0004] Among them, R 1 and R 2 Can be the same or different, both are C 1 -C 5 The straight-chain or branched aliphatic groups or one or both of them are hydrogen atoms. 3-Hydroxyglutarate compounds are generally prepared by reducing 3-oxoglutarate, as shown below: [0005] [0006] where R 1 with R 2 Same as defined above. [0007] One of the conventional methods i...

Claims

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Application Information

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IPC IPC(8): C07C69/675C07C67/31
Inventor 王尚启路明丁红军徐艳红
Owner 河南豫辰药业股份有限公司
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