Polychlorinated biphenyl (PCBs) homologue semiantigen and preparation method thereof

A polychlorinated biphenyl and monochlorinated biphenyl technology is applied in the field of polychlorinated biphenyl homolog hapten and its preparation, and can solve the problems such as the preparation of polychlorinated biphenyl hapten which has not yet been seen

Inactive Publication Date: 2008-04-09
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there is no domestic prep

Method used

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  • Polychlorinated biphenyl (PCBs) homologue semiantigen and preparation method thereof
  • Polychlorinated biphenyl (PCBs) homologue semiantigen and preparation method thereof
  • Polychlorinated biphenyl (PCBs) homologue semiantigen and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Preparation of 3,4-dichlorobiphenyl:

[0032] (1) In a 100ml beaker, warm 0.05 mol of 1,2-dichloroaniline (8.101g) and 5ml of water until the chloroaniline melts, then add 10ml of concentrated hydrochloric acid, stir vigorously, add 20ml of water, and heat until the mixture is almost completely dissolved. Then 5 ml of water was added and stirred until a homogeneous emulsion suspension was formed, at which point 3,4-dichloroaniline hydrochloride was precipitated as fine crystals. Allow to cool to room temperature, add a few pieces of small ice, cool with an ice-water bath outside, diazotize with 30% sodium nitrite at 4°C, and use pH test paper to control the acidity of the reaction to be 2-3. Endpoints were monitored with starch potassium iodide test paper.

[0033] (2) The solution after diazotization was poured into 60 ml of benzene cooled with ice water in advance, and 5 mol / L KOH solution was added dropwise at 4°C. When alkali is added, a yellow precipitation act...

Embodiment 2

[0037] Application of hapten

[0038] The polychlorinated biphenyl hapten prepared by the invention is mainly used in the immunodetection of polychlorinated biphenyls in the environment. One of its main uses is that it can be used to directly couple with protein macromolecules to prepare immunogens for immunizing animals, and then to prepare corresponding monoclonal or polyclonal antibodies. The following is an example of the use of 3,4-dichlorobiphenyl hapten:

[0039] Weigh 0.4 mmol of the hapten 4-(3,4-dichlorobiphenyl)-4-oxo-butyric acid, put it in a clean and dry small conical flask, and add 400 μL of DMF to dissolve it. 64.8 mg of DCC and 38.8 mg of NHS were weighed and dissolved in 300 μL DMF, and added dropwise to a small conical flask under magnetic stirring, and the reaction was stirred at room temperature for 8 h and overnight at 4 °C. The product after the reaction was placed in a low-temperature high-speed centrifuge at 9000 r / min, and the supernatant was separa...

Embodiment 3

[0041] Preparation of 3,4,4'-trichlorobiphenyl and its hapten

[0042] (1) In a 100ml beaker, warm 0.05 moles of 1,2-dichloroaniline (8.101g) and 10ml of water to melt, then add 15ml of concentrated hydrochloric acid, stir, add 30ml of water, heat and stir until a uniform milky form is formed suspension. Allow to cool to room temperature, add a few pieces of small ice, cool with an ice-water bath outside, diazotize with 25% sodium nitrite at 5°C, and use pH test paper to control the acidity of the reaction to be 2-3. Endpoints were monitored with starch potassium iodide test paper.

[0043] (2) Pour the diazotized solution into 80 ml of chlorobenzene cooled with ice water in advance, and dropwise add a 5 mol / L NaOH solution at 5°C. When alkali is added, a yellow precipitation activated substance is formed, which reacts with chlorobenzene to generate 3,4,4'-trichlorobiphenyl. Reaction to strong alkaline so far. Then, the stirring was continued for 2 hours at room temperatur...

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Abstract

The invention relates to a PCBs homolog hapten and a preparation method thereof. The structural formula of PCBs hapten is right, wherein, R is equal to Cl, R1 is equal to H or Cl, n is equal to 1, 2, 3, R3 is equal to COCH2CH2COOH. The preparation method comprises the steps as follows: firstly, dichloroaniline is dissolved, thick salt is filled in for mixing, and the solution is heavily nitrided through 25 to 33 percent of sodium nitrate after being heated and dissolved through water of 20 to 40ml; secondly, 60 to 80ml of aromatic hydrocarbon solvent is filled in and mixed with the solution under 0 to 5 DEG C, and then thick alkali is dropped in the solution for mixing and reacting for 1 to 3 hours; thirdly, the reaction product is vaporized through vapor or the rude yellowish-brown product is obtained by extracting through non-polar organic solvent, 1 to 3g zinc powder and 1 to 3ml thick hydrochloric acid are filled in with no more gas generating and then mixture is filtered hotly and the crystal is extracted; fourthly, the mol rate of PCBs, succinic anhydride and water free AlCl3 is 1:1 to 2:1 to 3. The water free AlCl3 can be filled in multiple times within 1 to 2 hours under cold water bath. The reaction is stopped after being mixed for 16 to 56 hours in a sealing way. The invention has the advantages of simple step, quick and high yield.

Description

technical field [0001] The invention relates to a polychlorinated biphenyl and its preparation, in particular to a polychlorinated biphenyl (PCBs) homolog hapten and a preparation method thereof. Background technique [0002] Polychlorinated biphenyls (PCBs), as a kind of environmental hormone pollutants that have received extensive attention from environmental workers all over the world, have become a research hotspot in their detection methods. In recent years, the use of enzyme-linked immunosorbent assay to determine PCBs has become an improved research direction for its rapid monitoring methods. In the research articles published by several universities in China, the haptens of PCBs are all donated by foreign research institutions [1, 2]. So far, there is no report on the preparation method of PCB hapten in China. The physical, chemical, biological and toxicological properties of PCBs congeners vary. Therefore, the relevant frontier research requires that the analysis...

Claims

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Application Information

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IPC IPC(8): C07C59/84C07C59/88C07C51/353
Inventor 庄惠生陈寒玉
Owner SHANGHAI JIAO TONG UNIV
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