Method for determining content of bis-(N-bis(dimethylamino)methylene)-iminium chloride catalyst

A technology of imide chloride salt and dimethylamine group, applied in the field of analytical chemistry, can solve the problems of not finding a method for catalyst quality control, unable to accurately grasp the real amount of catalyst, expensive catalyst and other problems, achieving fast determination and easy operation. , the effect of small sample size

Pending Publication Date: 2021-03-26
JIANGSU FLAG CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] In patents CN103553974A and CN1718572A, the synthesis and preparation process of N-alkyl conjugated ionic quaternary ammonium salt catalyst and the good effect of applying it in the Halex reaction were studied, but no method for quality control of the catalyst reported in the literature was found
The research and development personnel of our laboratory found in practical applications that N-alkyl conjugated ionic quaternary ammonium salts are very easy to absorb moisture, and even a small amount of moisture absorption and pollution in the sample during storage will seriously affect its true content and cannot be accurate. Grasp the real amount of catalyst used in the Halex reaction, and then affect the reaction yield
Combined with the characteristics that the catalyst itself is expensive, difficult to obtain, and needs to be used accurately in the reaction, it is necessary to develop a content determination method that avoids the use of N-alkyl conjugated ionic quaternary ammonium salt standards

Method used

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  • Method for determining content of bis-(N-bis(dimethylamino)methylene)-iminium chloride catalyst
  • Method for determining content of bis-(N-bis(dimethylamino)methylene)-iminium chloride catalyst
  • Method for determining content of bis-(N-bis(dimethylamino)methylene)-iminium chloride catalyst

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Experimental program
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Effect test

Embodiment 1

[0038] 1. There is a batch of self-synthesized bis-(N-bis(dimethylamino)methylene)-imide chloride salt catalyst samples. After standing for a period of time, the appearance of the sample absorbs moisture. Synthesizers need to know before using the catalyst The exact content is analyzed by proton nuclear magnetic spectroscopy, and the specific steps include:

[0039] (1) Accurately weigh 29.22 mg of internal standard hydroquinone and 27.54 mg of bis-(N-bis(dimethylamino)methylene)-imide chloride salt into the sample bottle, add 0.6 mL of deuterated methanol After dissolving, transfer to NMR tube for H NMR test. The resonant frequency of the nuclear magnetic resonance spectrometer is 400MHZ, the pulse dump angle is 30 degrees, the test temperature is 30°C, the spectrum width is 10ppm, and the delay time is 15s.

[0040] (2) if figure 1 As shown, the methyl resonance peak at the chemical shift of δ=2.91ppm was selected as the quantitative peak of the catalyst sample. The catal...

Embodiment 2

[0042] 1. There is a batch of self-synthesized bis-(N-bis(dimethylamino)methylene)-imide chloride salt catalyst samples. After standing for a period of time, the appearance of the sample absorbs moisture. Synthesizers need to know before using the catalyst The exact content is analyzed by proton nuclear magnetic spectroscopy, and the specific steps include:

[0043] (1) Accurately weigh 41.50 mg of internal standard maleic acid and 17.63 mg of bis-(N-bis(dimethylamino)methylene)-imide chloride salt into a sample bottle, add 0.6 mL of deuterated acetonitrile to dissolve Afterwards, it was transferred to an NMR tube for the H NMR spectrum test. The resonant frequency of the nuclear magnetic resonance spectrometer is 400MHZ, the pulse dump angle is 30 degrees, the test temperature is 25°C, the spectrum width is 10ppm, and the delay time is 20s.

[0044] (2) if figure 2 As shown, the methyl resonance peak at the chemical shift of δ=3.11ppm was selected as the quantitative peak of...

Embodiment 3

[0046] 1. There is a batch of self-synthesized bis-(N-bis(dimethylamino)methylene)-imide chloride salt catalyst samples. After standing for a period of time, the appearance of the sample absorbs moisture. Synthesizers need to know before using the catalyst The exact content is analyzed by proton nuclear magnetic spectroscopy, and the specific steps include:

[0047] (1) Accurately weigh 6.87 mg of internal standard 1,4-dioxane and 13.25 mg of bis-(N-bis(dimethylamino)methylene)-imide chloride salt into the sample bottle, add 0.6 mL of deuterium water was dissolved and transferred to an NMR tube for proton NMR testing. The resonant frequency of the nuclear magnetic resonance spectrometer is 400MHZ, the pulse dump angle is 30 degrees, the test temperature is 23°C, the spectrum width is 10ppm, and the delay time is 25s.

[0048] (2) if image 3 As shown, the methyl resonance peak at the chemical shift of δ=2.86ppm was selected as the quantitative peak of the catalyst sample. T...

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Abstract

The invention discloses a method for determining the content of a bis-(N, N-bis(dimethylamino)methylene)-iminium chloride catalyst by a nuclear magnetic resonance hydrogen spectrum. The method comprises the following specific steps: preparing an internal standard sample solution and detecting the nuclear magnetic resonance hydrogen spectrum; adding a bis-(N, N-bis(dimethylamino)methylene)-iminiumchloride sample to be detected, and carrying out nuclear magnetic resonance hydrogen spectrum detection; and affiliating each characteristic peak in the nuclear magnetic resonance hydrogen spectrum, determining the characteristic peak of the compound to be detected and the characteristic peak of the internal standard substance, respectively integrating, and substituting the obtained data into a related formula to calculate the content. The method has the advantages of simplicity and convenience in operation, small sampling amount, good reproducibility, high accuracy and the like, and can be used for quickly and accurately quantifying the content of the catalyst required by the synthesis reaction.

Description

technical field [0001] The invention relates to the technical field of analytical chemistry, in particular to a method for measuring the content of bis-(N-bis(dimethylamino)methylene)-iminium chloride salt catalyst by using hydrogen nuclear magnetic resonance spectrum. Background technique [0002] Fluorine-containing aromatic compounds are important intermediates of fine chemicals such as medicines, pesticides, and dyes. These compounds are used to synthesize herbicides, fungicides, antineoplastic drugs, antipsychotics, anti-senile dementia drugs, and functional dyes. effect. The synthesis and application of aromatic fluorides have become the research focus of research institutions and enterprises in various countries. When preparing fluorinated aromatics, because arenes and metal fluorides are immiscible, it is often necessary to use a phase transfer catalyst, which can effectively promote the fluorination reaction, make the reaction milder and faster, and obtain higher s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N24/08
CPCG01N24/08
Inventor 李萍张璞赵渭段亚玲
Owner JIANGSU FLAG CHEM IND
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