Method for producing aliphatic carboxylic acid compound and pyridine compound adduct of aliphatic ketone compound

A technology of aliphatic carboxylic acid and manufacturing method, which is applied in the directions of carboxylate preparation, carboxylate preparation, organic chemistry, etc., can solve problems such as unknown, and achieve the effect of safety and easy manufacture

Pending Publication Date: 2020-04-21
JNC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in Non-Patent Document 1, only the production of aromatic carboxylic acid compounds is studied, and in Non-Patent Document 2, only the production of alicyclic carboxylic acid compounds is studied. Regarding linear or branched aliphatic It is unknown whether the group carboxylic acid compounds can also be produced in the same way
Moreover, so far, there has been no report of the successful production of straight-chain or branched aliphatic carboxylic acid compounds by this method.

Method used

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  • Method for producing aliphatic carboxylic acid compound and pyridine compound adduct of aliphatic ketone compound
  • Method for producing aliphatic carboxylic acid compound and pyridine compound adduct of aliphatic ketone compound
  • Method for producing aliphatic carboxylic acid compound and pyridine compound adduct of aliphatic ketone compound

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Experimental program
Comparison scheme
Effect test

Embodiment

[0164] Hereinafter, although an Example demonstrates this invention, this invention is not limited to these Examples. In addition, in Examples and Reference Examples, gas chromatography (gas chromatography, GC) was measured under the following conditions.

[0165]

[0166] Gas chromatograph: GC-2014 (Manufacturer: Shimadzu Corporation)

[0167] Column: DB-1ms (manufacturer: Agilent Technologies Inc., inner diameter: 0.25mm, film thickness: 0.25μm, length: 60m)

[0168] Carrier gas: helium, column flow rate 2.32mL / min

[0169] Injection conditions: 250°C, split ratio 30

[0170] Column temperature conditions: keep at 50°C for 5 minutes, then raise the temperature to 280°C at 20°C / min

[0171] Detector: Flame ionization detector (FID), 320°C

[0172]

[0173] (first step)

[0174] 11.7 g (0.1 mol) of diacetone alcohol and 30 mL of pyridine were put into a four-necked flask with a capacity of 500 mL, and mixed. 25.4 g (0.1 mol) of iodine was added to the obtained raw ma...

Embodiment 2

[0183] (first step)

[0184] 11.7 g (0.1 mol) of diacetone alcohol and 30 mL of pyridine were put into a four-necked flask with a capacity of 500 mL, and mixed. 25.4 g (0.1 mol) of iodine was added to the obtained raw material mixture, and it stirred for 90 minutes, heating in the water bath set to 60 degreeC, and obtained the reaction liquid. From the reaction liquid, unreacted pyridine was roughly removed by distillation under reduced pressure to obtain a reaction mixture containing a pyridine adduct. The reaction mixture was used in the next step without purification.

[0185] (second step)

[0186] To the reaction mixture containing the pyridine adduct was added an aqueous solution prepared by dissolving 8.4 g (0.2 mol) of sodium hydroxide in 100 mL of water, and stirred while heating in a water bath set at 90° C. for 1 hour to obtain a solution containing Hydrolyzate reaction mixture. The reaction mixture was used in the next step without purification.

[0187] (thir...

Embodiment 3

[0193] (first step)

[0194] 11.6 g (0.1 mol) of diacetone alcohol and 30 mL of pyridine were put into a four-necked flask with a capacity of 500 mL, and mixed. 25.6 g (0.1 mol) of iodine was added to the obtained raw material mixture, and it stirred for 90 minutes, heating in the water bath set to 60 degreeC, and obtained the reaction liquid. From the reaction liquid, unreacted pyridine was roughly removed by distillation under reduced pressure to obtain a reaction mixture containing a pyridine adduct. The reaction mixture was used in the next step without purification.

[0195] (second step)

[0196] To the reaction mixture containing the pyridine adduct was added an aqueous solution prepared by dissolving 10.0 g (0.25 mol) of sodium hydroxide in 100 mL of water, and stirred while heating in a water bath set at 90° C. for 1 hour to obtain a solution containing Hydrolyzate reaction mixture. The reaction mixture was used in the next step without purification.

[0197] (th...

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Abstract

Provided are: a method for producing an aliphatic carboxylic acid compound safely and easily from a starting material that can be obtained or produced industrially without generating a harmful substance such as haloform; and a pyridine compound adduct of an aliphatic ketone compound. The method for producing an aliphatic carboxylic acid compound is a method for producing an aliphatic carboxylic acid compound represented by Formula (I), and comprises: a first step for obtaining a pyridine compound adduct by adding a pyridine compound to an aliphatic ketone compound having an alpha-methyl groupin the presence of an oxidizing agent; and a second step of hydrolyzing the pyridine compound adduct in the presence of a base. In the Formula, R1 represents a substituted or unsubstituted linear alkyl group having 4-8 carbon atoms or a substituted or unsubstituted branched alkyl group having 4-8 carbon atoms; M represents hydrogen, a metal belonging to Group 1 or Group 2 of the periodic table, amethyl group, an ethyl group, an n-propyl group or an isopropyl group.

Description

technical field [0001] The present invention relates to a method for producing an aliphatic carboxylic acid compound and a pyridine compound adduct of an aliphatic ketone compound. Background technique [0002] Aliphatic carboxylic acid compounds have uses in fragrances, cosmetics, food raw materials, pharmaceutical intermediates, polymer raw materials, plasticizers, etc., and are highly demanded in various fields and are widely distributed in the market. [0003] For example, 3-hydroxyisovaleric acid (3-Hydroxy3-MethylButyrate, HMB), one of the aliphatic carboxylic acid compounds, has shown the effect of promoting the synthesis of muscle protein and inhibiting the decomposition of muscle protein. The preparation ingredients such as supplements have attracted attention. [0004] As a method for producing 3-hydroxyisovaleric acid, the following methods are known. [0005] Patent Document 1 describes a method of oxidizing diacetone alcohol using hypochlorite or chlorine as a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/41C07C51/02C07C59/01C07D213/20C07D213/127
CPCC07C51/41C07C51/02C07D213/20C07D213/127C07C59/01
Inventor 仓田大成谢小毛岛田太一
Owner JNC CORP
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