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Stable isotopic labeled 2-isopropylthioxanthone and synthetic method thereof

A technology of isopropylthioxanthone and stable isotopes, applied in the field of stable isotope labeling of 2-isopropylthioxanthone and its synthesis

Active Publication Date: 2015-11-25
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 are few reports on the technical information on stable isotope labeling of 2-isopropylthioxanthone and its synthesis methods at home and abroad

Method used

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  • Stable isotopic labeled 2-isopropylthioxanthone and synthetic method thereof
  • Stable isotopic labeled 2-isopropylthioxanthone and synthetic method thereof
  • Stable isotopic labeled 2-isopropylthioxanthone and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] A. Stable isotope labeled bromobenzene-D 5 Synthesis

[0073] Add N-bromosuccinimide (NBS), anhydrous ferric chloride (its molar ratio is 1:0.1) successively in the flask, with molar ratio NBS: benzene-D 6 = 2:1 add benzene-D 6 , and acetonitrile with a reaction volume of 20%, stirred, heated to 100°C, and reacted for 6h. After the reaction, ether extraction, washing, anhydrous Na 2 SO 4 Drying, rectification under reduced pressure (20KPa, 160°C) to get bromobenzene-D 5 , the yield is 62.6% (by dropping into benzene-D 6 ), the product has a chemical purity of 98.3% through gas phase quantitative detection, and an abundance of 99.6atom%D through GC-MS / MS.

[0074] B. Stable isotope labeled cumene-D 5 Synthesis

[0075] Add metal magnesium to the flask, operate without water and oxygen, N 2 Protected, under stirring, add stable isotope-labeled bromobenzene-D with a syringe 5 , metal magnesium and bromobenzene-D 5 The molar ratio is 1:1, and the reaction volume ...

Embodiment 2

[0080] A. Stable isotope labeled bromobenzene-D5 Synthesis

[0081] Add dibromohydantoin (DBDMH), anhydrous ferric tribromide (its molar ratio is 1:0.1) successively in the flask, with molar ratio NBS: benzene-D 6 = 3:1 add benzene-D 6 , and acetonitrile with a reaction volume of 20%, stirred, heated to 90°C, and reacted for 7h. After the reaction, ether extraction, washing, anhydrous Na 2 SO 4 Drying, rectification under reduced pressure (20KPa, 160°C) to get bromobenzene-D 5 , the yield is 63.9 (in order to drop into benzene-D 6 ), the product has a chemical purity of 97.9% through gas phase quantitative detection, and an abundance of 99.6atom%D through GC-MS / MS.

[0082] B. Stable isotope labeled cumene-D 5 Synthesis

[0083] Add metal magnesium to the flask, operate without water and oxygen, N 2 Protected, under stirring, add stable isotope-labeled bromobenzene-D with a syringe 5 , metal magnesium and bromobenzene-D 5 The molar ratio is 2:1, and the reaction volu...

Embodiment 3

[0088] A. Stable isotope labeled bromobenzene-D 5 Synthesis

[0089] Ammonium tribromide (TBAB) and anhydrous ferric chloride (wherein the molar ratio of ammonium tribromide to anhydrous ferric chloride is 1:0.1) are added successively in the flask, with the molar ratio NBS:benzene-D 6 =4:1 add benzene-D 6 , and acetonitrile with a reaction volume of 20%, stirred, heated to 80° C., and reacted for 8 hours. After the reaction, ether extraction, washing, anhydrous Na 2 SO 4 Drying, rectification under reduced pressure (20KPa, 160°C) to get bromobenzene-D 5 , the yield is 63.4% (in order to drop into benzene-D 6 ), the product has a chemical purity of 98.0% through gas phase quantitative detection, and an abundance of 99.6atom%D through GC-MS / MS.

[0090] B. Stable isotope labeled cumene-D 5 Synthesis

[0091] Add metal magnesium to the flask, operate without water and oxygen, N 2 Protected, under stirring, add stable isotope-labeled bromobenzene-D with a syringe 5 , me...

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Abstract

The invention relates to stable isotopic labeled 2-isopropylthioxanthone and a synthetic method thereof. The stable isotopic labeled 2-isopropylthioxanthone is 2-isopropylthioxanthone labeled by D or 13C. The synthetic method comprises the following steps of using benzene and acetone which are labeled by stable isotopic D or 13C as raw materials; reacting the benzene and the acetone with magnesium to obtain Grignard reagent after benzene bromination; performing reduction and hydroxide radical bromination on the acetone to obtain 2-bromic propane; performing Grignard reaction to obtain isopropyl benzene; reacting the isopropyl benzene with dithio-salicylic acid; and synthesizing to obtain the 2-isopropylthioxanthone labeled by the stable isotopic D or 13C. Compared with the prior art, the stable isotopic labeled 2-isopropylthioxanthone has the advantages that a process route is simple, the 2-isopropylthioxanthone is easy to synthesize, products are easy to separate and purify, the chemical purity of the products is above 99.0%, isotope abundance is above 98.0% atom, requirements of trace detection in the field of food safety can be met fully, and economical efficiency and using value are excellent.

Description

technical field [0001] The invention belongs to the technical field of isotope labeling, and relates to a stable isotope-labeled 2-isopropylthioxanthone and a synthesis method thereof. Background technique [0002] 2-Isopropylthioxanthone (ITX), also known as 2-isopropylthioxanthone, English name 2-Isopropylthioxanthone, molecular weight 254.35g / mol, is light yellow powder or crystal, insoluble in water, slightly soluble in Alcohol, easily soluble in solvents such as benzene, toluene, chloroform and hot acetic acid. As a photoinitiator, ITX has been gradually applied to the surface of food packaging materials. However, recent studies have found that the residual photoinitiator in the ink can penetrate the food packaging material after being heated or illuminated, thereby contaminating the contacted food and causing potential harm to human health. In the Nestle baby milk incident in 2005, due to the detection of photoinitiators 2-isopropylthioxanthone (ITX) and isopropyl p-...

Claims

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Application Information

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IPC IPC(8): C07D335/16
CPCC07B2200/05C07D335/16
Inventor 方超杨维成罗勇杨超李美华盛立彦王浩然孙雯潘洁
Owner SHANGHAI RES INST OF CHEM IND
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