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Stable isotope labeled sudan red I and its synthesis method

A technology of stable isotope and synthesis method, which is applied in the field of stable isotope labeling of Sudan Red I and its synthesis, can solve the problems of high price of deuterated aniline, and it is difficult to meet the requirements of detection reagents, and achieves good economy, use value, and atom utilization. High rate, simple process effect

Inactive Publication Date: 2012-04-25
SHANGHAI RES INST OF CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] There is no literature report on the synthesis of isotope-labeled Sudan Red I in China. Only Antoni De reported the synthesis of Sudan Red I-D from deuterated aniline in 2008. 5 , the deuterated aniline used is expensive, and its synthetic Sudan red I-D 5 The isotope abundance is only 94.5%, which is difficult to meet the requirements of detection reagents

Method used

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  • Stable isotope labeled sudan red I and its synthesis method
  • Stable isotope labeled sudan red I and its synthesis method
  • Stable isotope labeled sudan red I and its synthesis method

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Embodiment 1

[0029] A stable isotope labeled Sudan Red I-D 5 A method for preparing phenyl, the method comprising the following steps:

[0030] 1. Stable isotope labeled nitrobenzene-D 5 preparation of

[0031] In a 100mL three-neck flask, add benzene-D 5 8.4g, add a mixture of 35g concentrated nitric acid and concentrated sulfuric acid dropwise at room temperature, raise the temperature to 40°C after the dropwise addition, react for 2 hours, separate and purify to obtain light yellow nitrobenzene-D 5 10.5g, yield 82.0%, GC detection, purity ≥ 98%; mass spectrometry detection, abundance ≥ 98atom%D.

[0032] 2. Stable isotope labeled aniline-D 5 preparation of

[0033] Add nitrobenzene-D into a 100mL three-necked flask 5 6.4g, add 3ml of concentrated hydrochloric acid, 10ml of water, 13g of iron powder, heat up to 40°C, react for 5 hours, separate and purify to obtain light yellow aniline-D 5 4.5g, yield 91.8%, GC detection, purity ≥ 98%; mass spectrometry detection, abundance ≥ 98at...

Embodiment 2

[0038] A stable isotope labeled Sudan red I- 13 C 6 A method for preparing phenyl, the method comprising the following steps:

[0039] 1. Stable isotope labeled nitrobenzene- 13 C 6 preparation of

[0040] Add benzene- 13 C 6 4.2g, add 30g of concentrated nitric acid and concentrated sulfuric acid mixture dropwise at 40°C, heat up to 60°C after the dropwise addition, react for 1 hour, separate and purify to obtain light yellow nitrobenzene- 13 C 6 5.4g, yield 84.4%, GC detection, purity ≥ 98%; mass spectrometry detection, abundance ≥ 98atom% 13 c.

[0041] 2. Stable isotope labeled benzene- 13 C 6 preparation of

[0042] Add nitrobenzene- 13 C 66.45g, 30ml of tetrahydrofuran, 10g of sodium borohydride was added in batches at 0°C, and after the addition was completed, the temperature was raised to 20°C, and reacted for 5 hours, separated and purified to obtain light yellow aniline- 13 C 6 4.6g, yield 92.9%, GC detection, purity ≥ 98%; mass spectrometry detection,...

Embodiment 3

[0047] A kind of synthetic method of stable isotope label Sudan red I, this method comprises the following steps:

[0048] (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;

[0049] (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;

[0050] (3) Stable isotope-labeled aniline, diazotized under acidic conditions of acetic acid, and then coupled with naphthol to obtain stable isotope-labeled Sudan I; the molar ratio of the stable isotope-labeled aniline to naphthol is 1: 1, The temperature of the coupling reaction is 0°C.

[0051] Stable isotope labeled benzene can be stable isotope 13 C label or stabl...

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Abstract

The invention relates to stable isotope labeled sudan red I and its synthesis method. The invention makes use of an organic synthesis method which comprises: employing stable isotope labeled benzene as a raw material, conducting nitration reaction so as to generate stable isotope labeled nitrobenzene, which then reacts with a reducing agent so as to obtain stable isotope labeled aniline, which is then subjected to diazotization as well as coupling with naphthol, thus obtaining stable isotope labeled sudan red I. Compared with prior art, the stable isotope labeled sudan red I prepared by the invention has chemical purity up to more than 98% and isotopic abundance over 98% after separation and purification, thus fully satisfying the demand for prohibited dye detection in the food safety field.

Description

technical field [0001] The invention relates to a new synthesis method of stable isotope-labeled Sudan I, that is, the stable isotope-labeled Sudan I is synthesized by using stable isotope-labeled benzene as raw material through nitration, reduction, diazotization and coupling. Background technique [0002] Sudan Red I, yellow powder, insoluble in water, slightly soluble in ethanol, soluble in oil, mineral oil, acetone and 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 Sudan Red I in food processing. However, driven by profit, incidents of adding Sudan Red illegally occurred frequently. In order to prevent Sudan Red I from entering the food chain, government surveillance agencies need a fast, accu...

Claims

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Application Information

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IPC IPC(8): C07C245/08C07B59/00
Inventor 徐仲杰卢伟京李美华卢浩李帅刘卫霞潘洁吴开成费荣杰
Owner SHANGHAI RES INST OF CHEM IND
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