CN-121974770-A - Synthesis method of para-aminophenol derivative

Abstract

The invention discloses a method for synthesizing para-aminophenol derivatives, which comprises the steps of dissolving a compound A in a mixed solvent of acetonitrile and water, cooling to 0-5 ℃, then adding an organic and inorganic acid catalyst for reacting at room temperature, distilling to remove the solvent, and then adding citric acid for continuing to react to obtain a compound B. The invention has the advantages of simple and easily obtained initial raw materials, easy large-scale purchase and storage, high purity of the synthesized p-aminophenol compound, capability of meeting the requirement of most industrial applications on the purity of the product, 。

Inventors

• FAN YILUN
• SHANG TIANQI
• LI BO
• Yu Jingshun
• JIANG JINGHAO
• GAO YUYANG
• DONG SHIHAO
• YANG MU
• LIU WANQI
• DONG HAIPENG
• YANG YI

Assignees

• 西安衡力设备工程有限公司

Dates

Publication Date

20260505

Application Date

20251231

Claims (5)

1. 1. The synthesis method of the para-aminophenol derivative is characterized by comprising the following steps of: ; R 1 is selected from C1-C10 alkyl, C1-C10 alkoxy, nitro, trifluoromethyl, hydroxy, halogen and C2-C10 ester, R 2 is selected from hydrogen, C1-C10 alkyl, C1-C10 alkoxy, nitro, trifluoromethyl, hydroxy and C2-C10 ester; (1) Dissolving the compound A in a mixed solvent of acetonitrile and water, and cooling to 0-5 ℃; (2) Then adding an organic and inorganic acid catalyst for room temperature reaction; (3) Distilling to remove the solvent, and then adding citric acid to continue the reaction to obtain the compound B.
2. 2. The method for synthesizing an aminophenol derivative according to claim 1, wherein R 1 is selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, nitro, trifluoromethyl, hydroxy, halogen, and C2-C6 ester.
3. 3. The method for synthesizing an aminophenol derivative according to claim 1, wherein R 2 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, nitro, trifluoromethyl, hydroxy, and C2-C6 ester.
4. 4. The method for synthesizing aminophenol derivatives according to claim 1, wherein the catalyst is selected from acetic acid, trifluoroacetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid, concentrated hydrochloric acid, concentrated sulfuric acid.
5. 5. The method for synthesizing aminophenol derivatives according to claim 1, wherein the volume ratio of acetonitrile to water in the mixed solvent of acetonitrile and water is 1 (0.5-2).

Description

Synthesis method of para-aminophenol derivative Technical Field The invention relates to a method for synthesizing a p-aminophenol compound, belonging to the technical field of chemical synthesis. Background P-aminophenol (p-Aminophenol, PAP) and its derivatives are important organic intermediates and are widely used in the fields of medicine, dyes, rubber, photographic chemicals, functional materials, etc. Among them, PAP is a key raw material for synthesizing paracetamol (acetaminophen), which is a widely used antipyretic analgesic agent worldwide. In addition, the compounds can be used for preparing antioxidants, liquid crystal materials and special high polymer materials. PAP has amino and hydroxyl, unique structure and high reactivity, and can participate in various reactions to construct complex molecules. The compound has good stability, is convenient to store and transport, has good solubility in water and various organic solvents, and is suitable for industrial scale application. PAP is an important precursor for synthesizing paracetamol, antomine and other medicines in the field of medicines, and is used for producing various colorants in the dye industry and serving the industries of textile, leather and the like. Therefore, the efficient production of PAP has important significance for meeting the requirements of multiple industries, promoting economic development and guaranteeing social life. Traditionally, PAP is produced primarily by scrap iron reduction, i.e., the reduction of p-nitrophenol with scrap iron under acidic conditions. However, the method can produce a large amount of iron-containing sludge, has serious environmental pollution, and has the problems of low yield, high production cost and the like. The p-nitrophenol catalytic hydrogenation reduction method has high selectivity and good environmental protection (the byproduct is mainly water), is an ideal way for replacing the traditional process, but is limited by high catalyst cost, strict requirement on raw material purity and larger equipment investment. The current mainstream method in industry is a nitrobenzene catalytic hydrogenation method, namely nitrobenzene is hydrogenated to generate phenyl hydroxylamine under low pressure under the action of Pt/C catalyst, and then converted into p-aminophenol through sulfuric acid rearrangement. The process has the advantages of low raw material cost, short flow, little pollution and the like, but has higher requirements on the aspects of catalyst activity, recovery efficiency, equipment investment and the like. Disclosure of Invention The invention provides a method for synthesizing p-aminophenol compounds efficiently, green and economically. The implementation process of the invention is as follows: a synthetic method of p-aminophenol derivatives comprises the following steps: R 1 is selected from C1-C10 alkyl, C1-C10 alkoxy, nitro, trifluoromethyl, hydroxy, halogen and C2-C10 ester, R 2 is selected from hydrogen, C1-C10 alkyl, C1-C10 alkoxy, nitro, trifluoromethyl, hydroxy and C2-C10 ester; (1) Dissolving the compound A in a mixed solvent of acetonitrile and water, and cooling to 0-5 ℃; (2) Then adding an organic and inorganic acid catalyst for room temperature reaction; (3) Distilling to remove the solvent, and then adding citric acid to continue the reaction to obtain the compound B. R 1 is preferably selected from C1-C6 alkyl, C1-C6 alkoxy, nitro, trifluoromethyl, hydroxy, halogen, C2-C6 ester, and R 2 is preferably selected from hydrogen, C1-C6 alkyl, C1-C6 alkoxy, nitro, trifluoromethyl, hydroxy, C2-C6 ester. The catalyst is selected from acetic acid, trifluoroacetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoromethanesulfonic acid, concentrated hydrochloric acid and concentrated sulfuric acid. In the mixed solvent of acetonitrile and water, the volume ratio of acetonitrile to water is 1 (0.5-2). The invention has the following advantages and positive effects. (1) The initial raw materials are simple and easy to obtain, aromatic hydrocarbon and phenol are common organic chemical raw materials, and the raw materials are wide in source, relatively low in price and easy to purchase and store on a large scale. (2) The product purity is high, and the p-aminophenol compound synthesized by the method has high purity by precisely controlling the reaction conditions, so that the requirement of most industrial applications on the product purity can be met. Detailed Description In order to better illustrate embodiments of the present invention, a further description will be provided below in connection with specific examples. It should be understood that these examples are only for illustrating the present invention and are not intended to limit the scope of the present invention. The experimental procedure, in which the specific conditions are not specified in the examples, is generally carried out according to the usual operating conditions or with reference to the recom