Method for the synthesis of glutaric acid from alpha-ketoglutaric acid

A technology of ketoglutaric acid and glutaric acid, which is applied in the field of preparation of glutaric acid, can solve the problems of not conforming to the concept of sustainable development of green chemistry, expensive raw material sources, difficult to synthesize and use in large quantities, etc., and achieve low production cost, high reaction The effect of safe conditions and mild reaction conditions

Active Publication Date: 2019-11-22
TIANJIN UNIV OF SCI & TECH
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Problems solved by technology

The synthesis methods include microwave-promoted cyclopentene oxidation to glutaric acid method, cyclopentene selective synthesis of glutaric acid method, etc., all of which are obtained by oxidation of cyclopentene. The source of product raw materials is expensive and it is not easy to synthesize and use in large quantities, and it does not conform to green Chemical Sustainable Development Concept

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  • Method for the synthesis of glutaric acid from alpha-ketoglutaric acid
  • Method for the synthesis of glutaric acid from alpha-ketoglutaric acid
  • Method for the synthesis of glutaric acid from alpha-ketoglutaric acid

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[0032] specific implementation

[0033] In order to understand the present invention, the present invention will be further described below in conjunction with embodiment: following embodiment is illustrative, not limiting, can not limit protection scope of the present invention with following embodiment.

[0034] A method for the synthesis of glutaric acid from alpha-ketoglutaric acid, the steps are as follows:

[0035] 1. Compound 1 (N 1 ,N 1 ,N 5 ,N 5 -tetraethyl-2-oxopentanediamide) synthesis.

[0036]

[0037] Add α-ketoglutaric acid (10.00g, 68.45mmol) and thionyl chloride (15.00ml, 205.34mmol) to a round bottom flask, and place the reaction mixture under reflux for one hour at 80°C. Pressure distilled to dark brown viscous oily liquid. After dissolving in tetrahydrofuran (20.00 ml), diethylamine was slowly added dropwise to the above mixture at a temperature of -10°C, and the reaction was continued overnight at room temperature with stirring. After the reactio...

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Abstract

The invention relates to a method for synthesizing glutaric acid from alpha-ketoglutaric acid. Specifically, under the mild condition, protected ketone thioacetal is subjected to catalytic hydrogenation reduction with raney nickel, recycling and reusing of reactants, solvent and a catalyst are achieved in a carbonyl reduction part in the most critical step, and the method for preparing the largely-demanded glutaric acid with the simple four-step method is developed. According to the method, the glutaric acid with the high yield is synthesized with the method for the first time, the yields of all steps are 92%, 78.6%, 90% and 85% in sequence, and the total yield is 55.32%; the method has broad prospects in synthetic application of compound library establishment.

Description

technical field [0001] The invention relates to the field of organic synthesis and the field of drug application, in particular to the Raney nickel-catalyzed hydrogenolysis thioketal reaction, which is a preparation method for glutaric acid with a large demand. [0002] technical background [0003] Glutaric acid is an important chemical raw material and intermediate, widely used in chemistry, construction, medicine, agriculture, plastic industry, etc., and is an important intermediate of many drugs and material structures. Therefore, the development of a new and improved preparation process for glutaric acid has attracted much attention. [0004] There are many methods for the preparation of glutaric acid, the more common two are recovery method and synthesis method. The recovery method includes glutaric acid by-products recovered during the preparation of adipic acid, glutaric acid by-products recovered during the preparation of succinic acid, separation and purification o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C55/12C07C51/06C07C51/60C07C59/347C07D339/06C07C231/02C07C235/74C07C231/12C07C233/05
CPCC07C51/06C07C51/60C07C231/02C07C231/12C07D339/06C07C59/347C07C235/74C07C233/05C07C55/12
Inventor 芦逵李超杰赵连波王栋郁彭
Owner TIANJIN UNIV OF SCI & TECH
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