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Perfluorinated alkyl aromatic hydroxylamine compound and preparation method thereof

A kind of technology of perfluoroalkyl aromatic hydroxylamine and compound, applied in the field of new perfluoroalkyl aromatic hydroxylamine compound

Inactive Publication Date: 2014-03-12
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In fluorocarbon phase catalysts, macrocyclic compounds such as metal porphyrins, metal phthalocyanines and Schiff base transition metal complexes are used as model substances in complex activation molecules There have been a lot of reports on the oxidation reaction of oxygen and catalyzed hydrocarbons, but they are either difficult to synthesize, low in yield, easy to dimerize to form complexes and inactivated, or easy to be oxidized and other problems are difficult to solve, and are not easy to obtain practical applications. Therefore, we need to design and synthesize new fluorocarbon phase catalysts

Method used

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  • Perfluorinated alkyl aromatic hydroxylamine compound and preparation method thereof
  • Perfluorinated alkyl aromatic hydroxylamine compound and preparation method thereof
  • Perfluorinated alkyl aromatic hydroxylamine compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Add 5 g of p-iodonitrobenzene and 40 ml of freshly steamed dimethyl sulfoxide into a 100 ml four-neck flask, and dissolve under electromagnetic stirring. Under nitrogen protection, 6.4g of active copper powder and 18.5g of perfluoroiodohexane were added, and stirred at room temperature for 30 minutes after the addition was complete. Then the temperature was slowly raised to 110° C., and the reaction was continued for 5 h. After the reaction was completed, 75ml of ice water was added to cool down the reaction solution, while stirring vigorously, and acidified by adding hydrochloric acid. After filtering, the filter cake was washed with water several times, extracted with ether, and washed with water until neutral. After drying and concentration, 8.0 g of yellow solid product 4-perfluorohexanenitrobenzene was obtained, with a yield of 91.0%. mp 69-70°C; 1 H NMR (CDCl 3 ) δ (ppm): 7.82 (d, J=11.72Hz, 2H), 8.35 (d, J=11.92Hz, 2H). 19 F NMR (CDCl 3 ) δ (ppm): -81.13(t,...

Embodiment 2

[0027] Add 5 g of p-iodonitrobenzene and 40 ml of freshly steamed dimethyl sulfoxide into a 100 ml four-neck flask, and dissolve them completely under electromagnetic stirring. Under nitrogen protection, 6.4g of active copper powder and 6.9g of perfluoroiodobutane were added, and stirred at room temperature for 30 minutes after the addition was complete. Then the temperature was slowly raised to 110° C., and the reaction was continued for 3 h. After the reaction was completed, 75ml of ice water was added to cool down the temperature of the reaction solution while stirring vigorously, and then acidified by adding hydrochloric acid. After filtering, the filter cake was washed with water several times, extracted with ether, and washed with water until neutral. After drying and concentration, 5.8 g of yellow solid product 4-perfluorohexanenitrobenzene was obtained, with a yield of 84.6%. 1 H NMR (CDCl 3 ) δ (ppm): 7.82 (d, J=11.72Hz, 2H), 8.35 (d, J=11.92Hz, 2H). 19 F NMR (CDC...

Embodiment 3

[0030] Add 5 g of p-iodonitrobenzene and 40 ml of freshly steamed dimethyl sulfoxide into a 100 ml four-neck flask, and dissolve them all under electromagnetic stirring. Under nitrogen protection, 6.4g of active copper powder and 10.9g of perfluorooctyl iodide were added, and stirred at room temperature for 30 minutes after the addition was complete. Then the temperature was slowly raised to 110° C., and the reaction was continued for 3 h. After the reaction was completed, 75ml of ice water was added to cool down the temperature of the reaction solution while stirring vigorously, and then acidified by adding hydrochloric acid. After filtering, the filter cake was washed with water several times, extracted with ether, and washed with water until neutral. After drying and concentration, 9.7 g of yellow solid product 4-perfluorooctanenitrobenzene was obtained, with a yield of 89.3%. 1 H NMR (CDCl 3 ) δ (ppm): 7.82 (d, J=11.72Hz, 2H), 8.35 (d, J=11.92Hz, 2H). 19 F NMR (CDCl 3...

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Abstract

The invention relates to a perfluorinated alkyl aromatic hydroxylamine compound and a preparation method thereof, and belongs to the field of chemical synthesis. The perfluorinated alkyl aromatic hydroxylamine compound has a structure formula shown in the specification. The preparation method of the perfluorinated alkyl aromatic hydroxylamine compound comprises the following steps of: synthesizing by coupled reaction and reduction reaction with iodo-4-nitrobenzene and perfluoroalkanes serving as raw materials; and recrystallizing, separating and purifying. The perfluorinated alkyl aromatic hydroxylamine compound is an important intermediate of a hydroxamic acid fluorocarbon phase catalyst containing a perfluoroalkyl group chain. The aromatic hydroxylamine also serves as an important raw material or intermediate in synthesis of pesticide, medicine and chemical products; the synthesis of the perfluorinated alkyl aromatic hydroxylamine compound enables the enriching of the variety of an aromatic hydroxylamine compound.

Description

[0001] technical field [0002] The invention relates to the field of chemical synthesis, in particular to a novel perfluoroalkyl aromatic hydroxylamine compound. technical background: [0003] In recent years, the synthesis and preparation of fluorocarbon phase catalysts have made great progress, mainly because some macrocyclic compounds containing fluorocarbon chains have high activity and high selectivity in activating molecular oxygen and catalyzing the oxidation reaction of hydrocarbons. The advantages of easy separation and recycling. Since the fluorocarbon phase system can completely separate the reagent and catalyst from the product under mild conditions, on the one hand, it will expand the industrial application of liquid phase catalysts or reagents, and on the other hand, it will also promote new and higher selectivity. Design and synthesis of reagents or catalysts. [0004] Among the fluorocarbon phase catalysts, there have been a lot of reports on the activat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C239/10
Inventor 苏莹莹邱滔吕新宇
Owner CHANGZHOU UNIV
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