Synthesis method of paraben compounds marked by stable isotope 13C or D

A p-hydroxybenzoic acid and stable isotope technology, applied in the field of stable isotope labeling compounds, can solve the problems of large corrosion equipment and waste liquid pollution, large amount of sulfuric acid catalyst, and reduced isotope abundance, etc., to achieve low corrosion and waste liquid pollution, Good economy and practical application value, the effect of reducing product cost

Inactive Publication Date: 2017-02-01
SHANGHAI RES INST OF CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The synthetic method of natural abundance p-hydroxybenzoic acid ester is mainly acid method synthesis, in existing synthetic technology, the catalyst used has sulfuric acid, vitriol salt, heteropolyacid salt, solid acid catalyst, gallium sulfate, high tin chloride and sulfonic acid catalysts, and in this reaction system, sulfate, heteropoly acid salt, gallium sulfate and high tin chloride all contain crystal water, and the hydrogen atoms in it replace the deuterium atoms on the product, resulting in a decrease in isotopic abundance
The traditional sulfuric acid catalyst consumes a large amount, the product separation is complicated, and the corrosion equipment and waste liquid pollution are large. The process of making it into a solid acid catalyst is not only complicated, but also increases the product cost. As a type of organic strong acid, sulfonic acid is in line with green chemical production. requirements, and has good catalytic performance, but there is no report on its use in the synthesis of high-abundance p-hydroxybenzoic acid esters

Method used

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  • Synthesis method of paraben compounds marked by stable isotope 13C or D
  • Synthesis method of paraben compounds marked by stable isotope 13C or D
  • Synthesis method of paraben compounds marked by stable isotope 13C or D

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Stable isotope labelled methyl parahydroxybenzoate- 13 C 6 The synthesis method of the method, the specific synthesis process of the method includes the following steps:

[0029] In a three-necked flask equipped with magnetic stirring, thermometer and reflux condenser, add 7.2g of p-hydroxybenzoic acid- 13 C 6 (0.05mol), 8.1mL methanol, 4.13g p-toluenesulfonic acid, heated to 60°C, kept the reaction for 9 hours under stirring; after the reaction, cooled to room temperature, filtered with suction, and adjusted the filtrate to pH=7~8, suction filtration, vacuum drying oven at 50℃ to constant weight, to obtain 5.17g white powder, with p-hydroxybenzoic acid- 13 C 6 The calculated yield is 65.4%, and methyl p-hydroxybenzoate- 13 C 6 The chemical purity is 99.11%, and the isotopic abundance is 99.21atom% 13 C.

Embodiment 2

[0031] Stable isotope labeled ethyl p-hydroxybenzoate- 13 C 6 The synthesis method of the method, the specific synthesis process of the method includes the following steps:

[0032] In a three-necked flask equipped with magnetic stirring, thermometer and reflux condenser, add 7.2g of p-hydroxybenzoic acid- 13 C 6 (0.05mol), 17.5mL of ethanol, 4.13g of p-toluenesulfonic acid, heated to 90°C, kept the reaction for 8 hours under stirring; after the reaction, cooled to room temperature, filtered with suction, and adjusted the filtrate to pH=7~8, suction filtration, vacuum drying oven at 50℃ to constant weight, obtain 5.79g white powder, and p-hydroxybenzoic acid- 13 C 6 The calculated yield is 67.3%, ethyl p-hydroxybenzoate- 13 C 6 The chemical purity is 99.05%, and the isotopic abundance is 99.13atom% 13 C.

Embodiment 3

[0034] Stable Isotope Labeled Propylparaben- 13 C 6 The synthesis method of the method, the specific synthesis process of the method includes the following steps:

[0035] In a three-necked flask equipped with magnetic stirring, thermometer and reflux condenser, add 7.2g of p-hydroxybenzoic acid- 13 C 6 (0.05mol), 23.4mL n-propanol, 4.13g p-toluenesulfonic acid, warm up to 65°C, keep the reaction for 12 hours while stirring; after the reaction is over, cool to room temperature, filter with suction, and use 10% NaOH solution to filter the filtrate Adjust to pH=7-8, filter by suction, and dry to constant weight at 50°C in a vacuum drying oven to obtain 6.53g of white powder with p-hydroxybenzoic acid- 13 C 6 The calculated yield is 70.2%, propyl p-hydroxybenzoate- 13 C 6 The chemical purity is 99.13%, and the isotopic abundance is 99.15atom% 13 C.

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Abstract

The invention relates to a synthesis method of paraben compounds marked by a stable isotope 13C or D. In the method, p-hydroxybenzoic acid, which is marked by the stable isotope 13C or D, and an alcohol compound are employed as raw materials for preparing the paraben compounds under the effect of an acidic catalyst p-toluenesulfonic acid. Compared with a synthesis process of the paraben compounds in natural abundance, the method is free of isotope dilution during the reaction process, has mild reaction conditions and high utilization rate on the isotopes. The paraben compounds marked by the stable isotope 13C or D, after separation and purification, are more than 99% in chemical purity and are more than 99 atom% in isotope abundance.

Description

Technical field [0001] The invention belongs to the field of stable isotope labeled compounds, and in particular relates to a stable isotope 13 C or D-labeled paraben compound synthesis method. Background technique [0002] Stable isotopes and their labeled compounds, as a unique emerging material, have the advantages of stable properties, simple operation, and no need for special protection compared with radioactive isotopes. As a class of high-tech and high-value-added commodities, Since the 1970s, it has been widely used in agriculture, food safety, life sciences, environment, clinical medicine, pharmacy and other fields. [0003] Parabens are a kind of important preservatives, commonly known as parabens, which have the characteristics of poor volatility, strong bactericidal ability and high stability. Because of their low toxicity and high efficiency, they are widely used in various fields such as medicine, food, cosmetics, pesticides, etc. They can be used directly, or as fun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/84C07B59/00G01N27/62
CPCC07C67/08C07B59/001C07B2200/05G01N27/62C07C69/84
Inventor 王雪婷王伟杜晓宁徐建飞宋明鸣侯捷雷雯岳韩笑
Owner SHANGHAI RES INST OF CHEM IND
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