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Synthetic method for stable isotope labeling basic orange II

A stable isotope and synthesis method technology, applied in the field of stable isotope-labeled basic orange II synthesis, to achieve the effects of simple process, reduced production cost, good economy and use value

Active Publication Date: 2013-08-21
SHANGHAI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no literature report on the synthesis of isotope-labeled Basic Orange II at home and abroad

Method used

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  • Synthetic method for stable isotope labeling basic orange II
  • Synthetic method for stable isotope labeling basic orange II
  • Synthetic method for stable isotope labeling basic orange II

Examples

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Embodiment 1

[0036] A Stable Isotope Labeled Basic Orange II-D 5 A method for preparing phenyl, the method comprising the following steps;

[0037] 1. Stable isotope labeled nitrobenzene-D 5 preparation of

[0038] Add 8.4g of benzene-D to a 100mL three-necked flask 5 , add dropwise 35g of concentrated nitric acid and concentrated sulfuric acid mixture at room temperature, after the dropwise addition, raise the temperature to 40°C, react for 2 hours, separate and purify to obtain light yellow 10.5g nitrobenzene-D 5 , yield 82.0%, GC detection, purity 98.8%; mass spectrometry detection, abundance 98.7atom%D.

[0039] 2. Stable isotope labeled aniline-D 5 preparation of

[0040] Add 6.4g of nitrobenzene-D5 into a 100mL three-necked flask, add 3mL of concentrated hydrochloric acid, 10mL of water, 13g of iron powder, raise the temperature to 40°C, react for 5 hours, separate and purify to obtain 4.5g of light yellow aniline-D 5 , yield 91.8%, GC detection, purity 99.2%; mass spectrometry...

Embodiment 2

[0045] A stable isotope labeled basic orange II- 13 C 6 A method for preparing phenyl, the method comprising the following steps:

[0046] 1. Stable isotope labeled nitrobenzene- 13 C 6 preparation of

[0047] Add benzene- 13 C 6 4.2g, add 30g of concentrated nitric acid and concentrated sulfuric acid mixture dropwise at 40°C. After the dropwise addition, raise the temperature to 60°C, react for 1 hour, separate and purify to obtain light yellow nitrobenzene- 13 C 6 5.4g, yield 84.4%, GC detection, purity 99.0%; mass spectrometry detection, abundance 99.2atom% 13 c.

[0048] 2. Stable isotope labeled aniline- 13 C 6 preparation of

[0049] Add 6.45g nitrobenzene- 13 C 6, 30mL of tetrahydrofuran, 10g of sodium borohydride was added in batches at 0°C, after the addition was completed, the temperature was raised to 20°C, and the reaction was carried out for 5 hours, separated and purified to obtain 4.6g of light yellow aniline- 13 C 6 , yield 92.9%, GC detection, p...

Embodiment 3

[0055] A kind of synthetic method of stable isotope labeled Basic Orange II, the method comprises the following steps:

[0056] (1) The stable isotope labeled benzene and nitric acid with a molar ratio of 1:1 are reacted under the action of catalyst sulfuric acid to prepare stable isotope labeled nitrobenzene, and the reaction temperature is 0°C;

[0057] (2) Stable isotope labeled nitrobenzene in solvent water and reducing agent H 2 The reaction generates stable isotope-labeled aniline, the molar ratio of the stable isotope-labeled nitrobenzene to the reducing agent is 1:1, and the reaction temperature is 0°C;

[0058] (3) Stable isotope-labeled aniline, diazotization under the acidic conditions of acetic acid, then coupled with m-phenylenediamine, and then acidic transposition reaction to obtain stable isotope-labeled Basic Orange II; described stable isotope-labeled aniline and m-phenylene The molar ratio of diamine is 1:1, and the temperature of the coupling reaction is 0...

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Abstract

The invention relates to a synthetic method for a stable isotope labeling basic orange II. The synthetic method comprises the steps of: carrying out nitration reaction by taking stable isotope labeling benzene as a raw material to generate stable isotope labeling nitrobenzene; then, subjecting the stable isotope labeling nitrobenzene and a reducing agent to reaction to obtain stable isotope labeling phenylamine; and finally, carrying out diazotization and m-phenylenediamine coupling transposition to obtain the stable isotope labeling basic orange II. After being separated and purified, the stable isotope labeling basic orange II prepared by the invention has the chemical purity of over 98% and the isotope abundance of over 98% and can sufficiently meet the requirement for detecting prohibited dyes in the field of food safety.

Description

technical field [0001] The invention relates to a stable isotope labeling method, in particular to a stable isotope-labeled basic orange II synthesis method. Background technique [0002] Basic Orange II, flashing brown-red crystal or powder, soluble in water to become yellowish orange, soluble in ethanol and ethylene glycol ether, slightly soluble in acetone, insoluble in benzene. It is a chemical dye, not a food additive. The substance has an azo structure, and the nature of this chemical structure determines that it is carcinogenic and has obvious toxic effects on the liver and kidney organs of the human body. At present, both developed countries in Europe and my country prohibit the use of Basic Orange II in food processing. However, driven by profit, incidents of illegally adding alkaline orange frequently occur. To prevent Alkaline Orange II from entering the food chain, government surveillance agencies need a fast, accurate and sensitive technology to detect it. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/22
Inventor 徐仲杰卢伟京卢浩李美华颜章伟江浙
Owner SHANGHAI RES INST OF CHEM IND
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