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CN-122010760-A - Paracetamol disinfection by-product and preparation method and application thereof

CN122010760ACN 122010760 ACN122010760 ACN 122010760ACN-122010760-A

Abstract

The invention discloses a paracetamol disinfection by-product, a preparation method and application thereof, belongs to the technical field of environmental chemistry and organic synthesis, and particularly relates to two paracetamol disinfection by-products, namely a compound P186 and a compound P220. The invention analyzes and identifies the structure and purity of the compound P186 and the compound P220 by simulating the reaction of acetaminophen and sodium hypochlorite during water disinfection, establishing a column chromatography gradient elution system and combining a high performance liquid chromatography-quadrupole-time-of-flight mass spectrometer, a high performance liquid chromatography, a carbon-13 nuclear magnetic resonance, a hydrogen-1 nuclear magnetic resonance and a Fourier transform infrared instrument and other analytical instruments. The method can provide standardized samples and technical support for conversion mechanism, toxicity evaluation and pollution prevention and control of acetaminophen disinfection byproducts in the environment.

Inventors

  • LV JING
  • SUN YUE
  • WANG XINYI
  • XIANG ZHENG
  • LIU BIN

Assignees

  • 辽宁大学

Dates

Publication Date
20260512
Application Date
20260126

Claims (10)

  1. 1. The paracetamol disinfection by-product is characterized by comprising a compound P186 with a structural formula shown as (I) and a compound P220 with a structural formula shown as (II); And 。
  2. 2. The method for preparing a paracetamol disinfection by-product according to claim 1, wherein the method for preparing compound P186 comprises the steps of: (1) The synthesis of the crude extract of the disinfection by-product of acetaminophen comprises the steps of dissolving acetaminophen in purified water, adding sodium hypochlorite solution, stirring and reacting at room temperature for 3 h-4 h, and vacuum drying to obtain a crude product; (2) Dissolving the obtained crude product in methanol, uniformly mixing with silica gel, drying, loading the mixture into a silica gel column, eluting with a solvent with the volume ratio of dichloromethane to methanol=100:1 as an eluent, and collecting all fractions obtained by separation; (3) Fractions were monitored by thin layer chromatography, fractions with the same Rf value were combined, concentrated by rotary evaporation and the solvent was removed to give purified compound P186.
  3. 3. The method for preparing a paracetamol disinfection by-product according to claim 2, wherein the step (3) specifically comprises the steps of using a solvent with a volume ratio of dichloromethane: methanol=15:1 as a developing agent, monitoring each fraction by thin layer chromatography analysis, combining all the fractions with an Rf value of 0.37, removing the solvent after rotary evaporation concentration, and obtaining the purified compound P186.
  4. 4. The method for preparing a paracetamol disinfection by-product according to claim 1, wherein the method for preparing the compound P220 comprises the steps of: (1) The synthesis of coarse acetaminophen disinfection by-product extract includes dissolving acetaminophen in purified water, adding sodium hypochlorite solution, stirring to react at room temperature 3 h-4 h and vacuum drying to obtain coarse acetaminophen product; (2) Dissolving the obtained crude product in methanol, uniformly mixing with silica gel, drying, loading the mixture into a silica gel column, eluting with a solvent with the volume ratio of dichloromethane to methanol=200:1 as an eluent, and collecting each flow obtained by separation; (3) Fractions were monitored by thin layer chromatography, fractions with the same Rf value were combined, concentrated by rotary evaporation and the solvent was removed to give purified compound P220.
  5. 5. The method for preparing a paracetamol disinfection by-product according to claim 4, wherein the step (3) comprises the steps of using a solvent with a volume ratio of dichloromethane: methanol=15:1 as a developing agent, monitoring each fraction by thin layer chromatography analysis, combining all the fractions with an Rf value of 0.44, removing the solvent after rotary evaporation concentration, and obtaining the purified compound P220.
  6. 6. The method for producing a paracetamol disinfection by-product according to any one of claims 2 to 5, wherein in the step (1), the available chlorine content in the sodium hypochlorite solution is not less than 7%.
  7. 7. The method for producing a paracetamol disinfection by-product according to any one of claims 2 to 5, wherein in the step (2), the obtained crude product is dissolved in methanol and uniformly mixed with 100-200 mesh silica gel, and the crude product is silica gel=1 (1-3) in terms of mass ratio.
  8. 8. The method for producing a paracetamol disinfection by-product according to any one of claims 2 to 5, wherein in the step (2), the silica gel column is packed with 200 mesh to 300 mesh silica gel.
  9. 9. Use of the paracetamol disinfection by-product of claim 1 in the assessment of toxicity of paracetamol disinfection by-product in the environment.
  10. 10. Use of the acetaminophen disinfection byproducts of claim 1 to provide standardized samples in pollution control.

Description

Paracetamol disinfection by-product and preparation method and application thereof Technical Field The invention belongs to the technical field of organic synthesis and environmental chemistry, and particularly relates to a compound P186 and a compound P220 of a paracetamol disinfection by-product, and a preparation method and application thereof. Background Acetaminophen is a widely used worldwide non-prescription antipyretic analgesic, often combined with other drugs to form a compound preparation. After the Chinese medicinal composition is taken by a human body, part of acetaminophen original shape and metabolites can enter a municipal sewage system along with excrement, and the acetaminophen can be discharged into a natural water body along with tail water due to the fact that the acetaminophen is difficult to completely remove by a traditional sewage treatment process. In addition, medical wastewater, drug abuse, random discarding of expired drugs, etc. can also lead to their entry into natural water environments. Acetaminophen is a typical trace organic pollutant of current environmental chemistry and ecological risk assessment because of wide use, complex approach to water, environmental durability and frequent detection in various water environments. The chlorination disinfection is a main means for ensuring the safety of drinking water, wherein sodium hypochlorite is used as an inorganic chlorine-containing disinfectant, has stronger oxidability, and is widely used in the disinfection and purification processes of water bodies in water supply systems. However, in the water treatment process, sodium hypochlorite can react with organic matters and other substances in water to generate chlorinated disinfection byproducts, and the chlorinated disinfection byproducts are potentially harmful to human health and environment. The research shows that the nitrogen-containing disinfection byproducts generated by the precursor through chlorination have higher toxic effect, stronger polarity and hydrophilicity than the conventional carbon-containing disinfection byproducts, are easier to migrate with water than the conventional disinfection byproducts, and can be widely used in the drinking water after chlorination. The prior research data shows that the nitrogen-containing disinfection byproducts can improve the level of oxidative stress and have carcinogenicity and mutagenicity. Acetaminophen in water can generate various disinfection byproducts in the water disinfection process. At present, no system reports on acetaminophen disinfection byproducts exist. Disclosure of Invention In order to solve the technical problems, the invention aims to provide a paracetamol disinfection by-product and a synthesis method and application thereof. In order to achieve the aim of the invention, the invention adopts the technical scheme that the paracetamol disinfection byproducts are a compound P186 with a structural formula shown as (I) and a compound P220 with a structural formula shown as (II). And A process for preparing acetaminophen disinfection by-product compound P186 comprising the steps of: (1) The synthesis of coarse acetaminophen disinfection by-product extract includes dissolving acetaminophen (APAP) in purified water, adding sodium hypochlorite solution, stirring to react at room temperature for 3 h-4 h, and vacuum drying to obtain coarse product. (2) Dissolving the obtained crude product in methanol, uniformly mixing with silica gel, drying, loading the mixture into a silica gel column, eluting with a solvent with the volume ratio of dichloromethane to methanol=100:1 as an eluent, and collecting all fractions obtained by separation; (3) Fractions were monitored by thin layer chromatography, fractions with the same Rf value were combined, concentrated by rotary evaporation and the solvent was removed to give purified compound P186. Further, in the step (3), a solvent with a volume ratio of dichloromethane to methanol=15:1 is adopted as a developing agent, all fractions are monitored through thin layer chromatography analysis, all the fractions with Rf value of 0.37 are combined, and the solvent is removed after rotary evaporation concentration, so that the purified compound P186 is obtained. A process for the preparation of acetaminophen disinfection by-product compound P220 comprising the steps of: (1) The synthesis of the crude extract of the disinfection by-product of acetaminophen comprises dissolving acetaminophen in purified water, adding sodium hypochlorite solution, stirring at room temperature for reaction of 3 h-4 h, and vacuum drying to obtain crude product. (2) Dissolving the obtained crude product in methanol, uniformly mixing with silica gel, drying, loading the mixture into a silica gel column, eluting with a solvent with the volume ratio of dichloromethane to methanol=200:1 as an eluent, and collecting fractions obtained by separation. (3) Fractions were monitored by thin layer chromatography,