Method for manufacturing aromatic nitrile compound

A technology of a nitrile compound and a manufacturing method is applied in the fields of the manufacture of an aromatic carboxylic acid compound, 2-naphthaleneacetic acid, and the manufacture of 2-naphthaleneacetonitrile, which can solve the problems of insufficient yield and the like, and achieve high efficiency.

Pending Publication Date: 2020-12-04
API CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the yields of these methods are not sufficient, and since sulfur is used in the Wilgroth reaction, it is considered that a large amount of sulfur is contained in the produced aromatic carboxylic acid, etc., so further improvement is required as an industrial production method.

Method used

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  • Method for manufacturing aromatic nitrile compound
  • Method for manufacturing aromatic nitrile compound
  • Method for manufacturing aromatic nitrile compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0317] Embodiment 1: the synthesis of carboxylic acid compound

[0318]

[0319] 3.00 g of 2'-naphthylethanone and 0.85 g of sulfur (1.5 mole times relative to 2'-naphthylethanone) were added to the reaction vessel after nitrogen replacement, and 4.61 g of morpholine (1.5 mole times relative to 2'-naphthyrophenone) was further added. 3 mole times of ethyl ketone), after stirring, react at 115° C. to 125° C. for 4 hours (to generate thioamide compound (thioamide compound)).

[0320] After cooling the reaction solution to 70°C to 80°C, add a 20% by weight aqueous solution of sodium hydroxide (a solution obtained by mixing 3.53 g of sodium hydroxide with 14.1 g of water. 5 moles relative to 2'-naphthylethanone twice the sodium hydroxide), react at 90°C to 105°C for 8 hours (hydrolysis). The reaction liquid was cooled to 50° C. to 60° C., 0.15 g of activated carbon (purified egret) was added, stirred, and then filtered. To the obtained filtrate, 35% hydrochloric acid (a solut...

Embodiment 2

[0324] Embodiment 2: the synthesis of carboxylic acid compound

[0325]

[0326] 120.00 g of 2'-naphthylethanone, 28.26 g of sulfur (1.25 mole times relative to 2'-naphthylethanone), p-toluenesulfonic acid monohydrate (p-Toluenesulfonic acid monohydrate) ) 13.41g (0.10 mole times relative to 2'-naphthylethanone) and morpholine 184.26g (3 mole times relative to 2'-naphthylethanone), after stirring, react at 115°C to 125°C for 9 hours (Generation of thioamide compounds).

[0327] After the reaction solution was cooled to 70°C to 80°C, an aqueous sodium hydroxide solution with a concentration of 20% by weight was added (a solution obtained by mixing 141.00 g of sodium hydroxide with 564.01 g of water. 5 moles relative to 2'-naphthylethanone twice the sodium hydroxide), react at 90°C to 105°C for 4 hours (hydrolysis). The reaction solution was cooled to 60°C to 70°C, 120.00 g of water and 240.00 mL of toluene were added, stirred at 65°C to 75°C, and after standing still, the ...

Embodiment 3

[0332] Embodiment 3: the synthesis of carboxylic acid compound

[0333]

[0334] 120.00 g of 2'-naphthylethanone, 120 mL of toluene (1.0 times the volume of 2'-naphthylethanone), and 0.34 g of methanesulfonic acid (1.0 times the volume of 2'-naphthylethanone 0.005 mol times), 184.26 g of morpholine (3 mol times relative to 2'-naphthylethanone) was further added, stirred, and then distilled for 15 hours.

[0335] After concentration, 28.26 g of sulfur (1.25 mole times relative to 2'-naphthylethanone) was added, and the mixture was reacted at 95°C to 105°C for 7 hours (to generate a thioamide compound).

[0336] After the reaction solution was cooled to 70°C to 80°C, an aqueous sodium hydroxide solution with a concentration of 20% by weight was added (a solution obtained by mixing 141.00 g of sodium hydroxide with 564.01 g of water. 5 moles relative to 2'-naphthylethanone twice the sodium hydroxide), react at 90°C to 105°C for 7 hours (hydrolysis). The reaction liquid was c...

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Abstract

The present invention provides a method for manufacturing a high-purity aromatic nitrile compound and aromatic carboxylic acid compound safely, inexpensively, and with high efficiency. A compound (2)is subjected to the Willgerodt reaction in the presence of an additive as needed, and the resultant amide compound (3) is hydrolyzed and then neutralized, and a carboxylic acid compound (4) is obtained. The carboxylic acid compound (4) is reacted with a halogenating agent in an organic solvent in the presence of a catalyst as needed, then reacted with an amidating agent, the resultant amide compound (5) or (6) is reacted with a dehydrating agent, and a nitrile compound (1) is obtained. Alternatively, the carboxylic acid compound (4) is reacted with a halogenating agent and a compound represented by the formula R6SO2R7 in an organic solvent in the presence of a catalyst as needed, and a nitrile compound (1) is obtained. The symbol Np is a naphthyl group which may have a substituent, R5 represents a C1-3 alkylene group, and the other symbols are as described in the specification.

Description

technical field [0001] The present invention relates to a method for producing an aromatic nitrile compound, preferably 2-Naphthylacetonitrile, which is useful as a raw material for synthesis of various pharmaceuticals, agricultural chemicals, and chemical products and as an intermediate for synthesis. [0002] Furthermore, the present invention relates to an aromatic carboxylic acid useful as a raw material for synthesis of the aromatic nitrile compound of the present invention and an intermediate for synthesis, and as a raw material for synthesis of various pharmaceuticals, agricultural chemicals, and chemical products, and an intermediate for synthesis A method for producing a compound, preferably 2-naphthaleneacetic acid (2-Naphthaleneacetic Acid). Background technique [0003] 2-Naphthylacetonitrile is useful as a raw material and an intermediate for synthesis of various pharmaceuticals, agricultural chemicals, and chemicals. In addition, aromatic nitrile compounds hav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/20C07C51/06C07C57/38C07C255/33
CPCC07C57/38C07C51/06C07C253/20C07C255/33C07C231/02C07C51/305C07C51/00C07D295/194C07C233/11C07C57/40C07C2602/10
Inventor 长滨正树大宫秀贵尾门大树谷池裕次
Owner API CO LTD
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