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Pre-column derivatization reagent and preparation process

A pre-column derivatization and reagent technology, which is applied in the field of synthesis of pre-column derivatization reagents, can solve the problems of long derivatization time, complicated process operation, and poor analysis precision

Active Publication Date: 2012-09-12
HUBEI GRAND LIFE SCI & TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The main methods for early detection of taurine content are: nitrogen determination method, volumetric measurement method, automatic potentiometric titration method, spectrophotometry method, liquid chromatography post-column derivatization method, these methods have poor analytical precision or complicated operation
[0005] In recent years, there is a method for quantitative detection with HPLC after pre-column derivatization, such as the method for measuring taurine content by pre-column derivatization of o-phthalaldehyde (seeing the 10th issue of volume 16 of "Chinese Journal of Health Inspection" in October 2006). The derivatization reagents in the method need to be prepared and used temporarily, the process operation is complicated, and it is not convenient for large-scale promotion and use. There is also a pre-column derivatization method in which 2,4-dinitrofluorobenzene is used as a derivatization reagent. The derivatization time of this method is long and the derivatization intermediate The body is unstable and the detection reproducibility is not good

Method used

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  • Pre-column derivatization reagent and preparation process
  • Pre-column derivatization reagent and preparation process
  • Pre-column derivatization reagent and preparation process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 The preparation of 2-chloro-3,5-dinitrobenzoyl chloride

[0026] Add 24.6 g of 2-chloro-3,5-dinitrobenzoic acid (100 mmol), 150 ml of thionyl chloride (2.0 mol) into a 500 ml single-necked flask, drop in 0.5 ml of DMF, stir magnetically, and heat up to 60-70°C , reacted for 5 to 6 hours, concentrated under reduced pressure to distill out thionyl chloride, and cooled to room temperature to obtain 25.8 g of a light yellow solid, namely 2-chloro-3,5-dinitrobenzoyl chloride, with a yield of 97.4%.

Embodiment 2

[0027] Example 2 The preparation of 2-chloro-3,5-dinitrobenzamide

[0028] Add 25.8 g of 2-chloro-3,5-dinitrobenzoyl chloride to 77.4 ml of acetone, stir to dissolve it, add 1.5 mol / L dilute ammonia water dropwise under stirring in an ice-water bath, and adjust the pH of the system to 6-7. Continue to stir for 1 hour, extract 3 times with 100ml ethyl acetate, wash the combined ester layer twice with saturated sodium bicarbonate solution, wash once with saturated sodium chloride solution, dry the ester layer with anhydrous magnesium sulfate for 2 hours, and concentrate by suction filtration , to obtain a yellow oil, add 100ml of methyl tert-butyl ether and stir, separate out light yellow crystals, filter with suction, dry to obtain 20.5 grams of light yellow crystals which are 2-chloro-3,5-dinitrobenzamide, yield 85.8%, 1H NMR (CDCl3) δ: 9.00 (d, J = 2.64Hz, 1H), 8.54 (d, J = 2.64Hz, 1H), 8.30 (s, 1H), 8.12 (s, 1H).

Embodiment 3

[0029] Example 3 2-chloro-3,5-dinitrobenzamide and 2,4-dinitrofluorobenzene

[0030] A comparative experiment of detecting taurine by pre-column derivatization method

[0031] Steps

[0032] 1. Precisely weigh 5 mg of taurine sample, dissolve it in deionized water, transfer it into a 100ml volumetric flask, shake well, place it in an ultrasonic vibrator for 5-10 minutes, add deionized water to dilute to the mark as the solution to be tested.

[0033] 2.2-Chloro-3,5-dinitrobenzamide derivatization step

[0034] 2.1 Accurately measure 1ml of the solution to be tested, place it in four 10ml measuring bottles A, B, C, and D, add 1ml of 0.5mol / L sodium bicarbonate solution (pH9.0), 1% 2-chloro-3 , 0.5ml of 5-dinitrobenzamide in acetonitrile solution, shake well, and heat in a water bath at 60°C.

[0035] 2.2 Accurate timing of the heating process: A bottle is heated for 15 minutes, B is heated for 30 minutes, C is heated for 45 minutes, and D is heated for 60 minutes.

[0036] ...

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Abstract

The invention relates to a pre-column derivatization reagent for detection on taurine and a preparation process for the same, wherein the derivatization reagent has a chemical name of 2-chlor-3,5-dinitrophenyl formamide, moderate conditions of a reaction with the taurine, a fast speed, and high sensitivity; the problem mainly solved according to the invention is to find a derivatization reagent easy to be subjected to pre-column derivatization with the taurine, high in detection sensitivity, and easy to store; and the 2-chlor-3,5-dinitrophenyl formamide found and prepared according to the invention is stable in property, fast in the speed of reaction with an amino compound, and capable of being widely used as an amino acid compound, especially used as a high-sensitivity liquid chromatography derivatization reagent for detection on taurine.

Description

technical field [0001] The invention relates to a synthesis method and application of a pre-column derivatization reagent, in particular to a synthesis method and application of a taurine pre-column derivatization reagent 2-chloro-3,5-dinitrobenzamide. Background technique [0002] Taurine (molecular formula NH2CH2CH2SO2OH, chemical name 2-aminoethanesulfonic acid) is an amino acid extracted from ox bile for the first time in 1827, so it is also called taurine. The pure product is white to off-white crystalline powder, odorless, slightly sour taste. Soluble in water, slightly soluble in organic solvents such as ethanol, ether or acetone. Taurine is a sulfur-containing non-protein amino acid that exists in a free state in the body and does not participate in the biosynthesis of proteins in the body, but is closely related to the metabolism of cystine and cysteine. The activity of cysteine ​​sulfite carboxylase (CSAD) for the synthesis of taurine in the human body is low, an...

Claims

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Application Information

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IPC IPC(8): C07C233/65C07C231/02G01N30/06
Inventor 朱毅吕菲刘莎熊丹杨尚金潘季红吴丽娟
Owner HUBEI GRAND LIFE SCI & TECH CO LTD
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