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Liquid phase detection method for detecting p-chlorobenzoyl chloride

A technology of p-chlorobenzoyl chloride and a detection method, which is applied in the field of drug analysis, can solve the problems of large detection error, large chromatographic column damage, large detection result error, etc., and achieves high system applicability, good linear relationship, and good accuracy. Effect

Pending Publication Date: 2022-06-07
浙江致新医药科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Acyl chloride compounds are easily hydrolyzed when exposed to water, making conventional liquid phase methods unsuitable for the detection of related substances of p-chlorobenzoyl chloride
In addition, acyl chlorides have strong reactivity and are easy to cause damage to the packing of the gas chromatographic column, and direct gas phase injection will cause great damage to the chromatographic column; meanwhile, alkyl acid chlorides have a large molecular weight and a high boiling point, so they are not suitable for headspace sampling. In addition, the alkyl acid chloride is unstable and easy to be hydrolyzed or esterified, and the detection error by gas chromatography is relatively large
[0005] People such as Chen Fengqin hydrolyze p-chlorobenzoyl chloride into p-chlorobenzoic acid and then use HPLC to measure the isomer impurities in p-chlorobenzoyl chloride, but it will be due to the possible presence of p-chlorobenzoic acid, m-chlorobenzoyl chloride Chlorobenzoic acid and o-chlorobenzoic acid lead to large errors in test results
[0006] People such as Jin Qian detect o-, meta-, and p-chlorobenzoyl chloride isomers by direct sampling method and methyl esterification method, but the gas phase temperature has a great influence on the content of acid chlorides, and acid chlorides can be converted into acid anhydrides at high temperatures. The higher the content of high acid anhydride, the higher the accuracy of product content determination, the higher the requirements for the type of gas chromatography column, and the higher boiling point of p-chlorobenzoic acid and its isomers, this method is only suitable for the detection of p-chlorobenzoyl chloride Isomer impurity, not suitable for detection of related substances
[0007] In addition, through the derivation of p-chlorobenzoyl chloride and ethanol, gas chromatography directly injects samples to detect ethyl ester compounds to detect the isomers of p-chlorobenzoyl chloride, but compared with the methyl esterification method, ethanol derivatization time and derivatization temperature Both require higher requirements and troublesome operation

Method used

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  • Liquid phase detection method for detecting p-chlorobenzoyl chloride
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  • Liquid phase detection method for detecting p-chlorobenzoyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] (1) Experimental materials and instrument conditions

[0045] Instrument: Thermo Fisher Ultimate 3000, chromatographic column: Agilent InfinityLab Poroshell 120PFP 4.6×250mm, 4μm; flow rate: 1.0mL / min; column temperature: 10℃; injection volume: 5μL, detection wavelength: 200nm; mobile phase A: Phosphate buffer (20 mM potassium dihydrogen phosphate aqueous solution, adjusted to pH 2.0 with phosphoric acid, potassium dihydrogen phosphate is AR grade, phosphoric acid is HPLC grade, water is high-purity water): acetonitrile (acetonitrile is HPLC grade) = 75:25 (v / v), mobile phase B: acetonitrile (acetonitrile is HPLC grade), the gradient elution procedure is shown in Table 2.

[0046] Table 2. Gradient elution procedure

[0047] time (min) 0 15 35 60 60.1 70 Mobile phase A (%, v / v) 100 100 80 43 100 100 Mobile phase B (%, v / v) 0 0 20 57 0 0

[0048] (2) Experimental steps (take m-chlorobenzoyl chloride as an example)

[0049] Pr...

Embodiment 2

[0078] Example 2: System suitability test of the detection method of the present invention

[0079] The system suitability is achieved by the system suitability solution and the 6-pair control solution. It is required that the resolution between the chromatographic peaks of p-chlorobenzoyl chloride and m-chlorobenzoyl chloride in the system suitability solution is not less than 1.5, and the number of theoretical plates is equal to the number of pairs. Chlorobenzoyl chloride chromatographic peak count, not less than 5000; the RSD of the chromatographic peak area of ​​p-chlorobenzoyl chloride in 6 needles of the control solution is not greater than 5.0%, and the RSD of the retention time is not greater than 1.0%; 7 pairs of p-chlorobenzene in the control solution The RSD of the chromatographic peak area of ​​formyl chloride is not more than 5.0%, and the RSD of the retention time is not more than 1.0%.

Embodiment 3

[0080] Example 3: Specificity of the detection method of the present invention

[0081] Specificity is achieved by assaying blank solutions, positioning solutions, test solutions, and spiked test solutions. It is required that the blank solution has no interference with the detection of related substances; the peak purity of the chromatographic peaks in the positioning solution is not less than 990; the detection of related substances in the test solution has no interference, the separation degree between the chromatographic peaks is not less than 1.5, and the peaks of the chromatographic peaks are not less than 1.5. The purity is not less than 990; the detection of related substances in the spiked test solution has no interference, the resolution between chromatographic peaks is not less than 1.5, and the peak purity of the chromatographic peaks is not less than 990.

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Abstract

The invention discloses a liquid phase detection method for detecting p-chlorobenzoyl chloride, which achieves the purpose of detecting and controlling isomers by carrying out derivative reaction on an acyl chloride compound and excessive absolute methanol and detecting a generated methyl ester compound, can detect other impurities such as p-chlorobenzoic acid and the like, and has the advantages of simple derivative conditions, simplicity and convenience in operation, high detection efficiency and high detection accuracy. The method disclosed by the invention is efficient, convenient and simple to operate, completely conforms to guidance principles verified by methods in Chinese pharmacopoeia in the aspects of system applicability, specificity, accuracy, precision and durability, and can be used for quality control of p-chlorobenzoyl chloride.

Description

technical field [0001] The invention belongs to the technical field of drug analysis, and in particular relates to a liquid phase detection method for detecting p-chlorobenzoyl chloride. Background technique [0002] p-Chlorobenzoyl chloride is a colorless or slightly yellow liquid, insoluble in water, soluble in alcohol, ether, acetone, and decomposed in water. By the reaction of p-chlorotoluene and chlorine, and then obtained by hydrolysis. Commonly used in the pharmaceutical industry. [0003] There may be isomers in p-chlorotoluene, resulting in the possible existence of corresponding isomers in p-chlorobenzoyl chloride, such as m-chlorobenzoyl chloride and o-chlorobenzoyl chloride, and there may also be corresponding hydrolysis acids, such as p-chlorobenzoic acid, m-chlorobenzoic acid, and o-chlorobenzoic acid. The existence of the above substances affects their quality, so it is necessary to detect and control the above impurities. [0004] Acyl chloride compounds ...

Claims

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Application Information

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IPC IPC(8): G01N30/06G01N30/74
CPCG01N30/06G01N30/74Y02A50/30
Inventor 汪士金孙少发叶飞范康梅王国华
Owner 浙江致新医药科技有限公司
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