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Catalytic synthesis of phenylhydroxylamine compound

A compound, the technology of phenylglycerin, which is applied in the field of synthesizing phenylglycerin compounds under the catalysis of selenium, can solve the problems of not being used for the preparation of phenylglycerin compounds, corrosive and large chlorine-containing by-products, easy to pollute the environment, etc., and achieve easy clean production , less investment in equipment and mild reaction conditions

Inactive Publication Date: 2006-05-17
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Application Information

AI Technical Summary

Problems solved by technology

A large amount of corrosive chlorine-containing by-products are produced during the reaction process, which not only severely corrodes equipment but also easily pollutes the environment
Literature [Liu Xiaozhi, Peng Aidong, Lu Shiwei. Chinese Patent Application No. 02143126.4; Liu Xiaozhi, Lu Shiwei. Chinese Patent Application No. 02147591.1; Liu Xiaozhi, Lu Shiwei. Chinese Patent Application No. 02147590.3; Liu Xiaozhi, Lu Shiwei. Chinese Patent Application No. 03160125.1] reported selenium-catalyzed synthesis of aniline method of derivatives, but not for the preparation of phenylene compounds

Method used

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  • Catalytic synthesis of phenylhydroxylamine compound
  • Catalytic synthesis of phenylhydroxylamine compound
  • Catalytic synthesis of phenylhydroxylamine compound

Examples

Experimental program
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Effect test

Embodiment 1

[0014] Embodiment 1, the synthesis of phenylene (N-hydroxyaniline) under selenium catalysis

[0015] Add nitrobenzene (10mmol), selenium (0.5mmol), sodium borohydride (25mmol), and absolute ethanol 40mL to a 100mL round-bottomed flask under nitrogen protection, and stir the reaction at room temperature (12°C) for 3 hours. After the product is filtered, the filtrate is concentrated and purified by recrystallization from petroleum ether (60-90° C.) to obtain benzene, m.p. 81° C. (decomposition), and the yield is 77%.

Embodiment 2

[0016] Embodiment 2, the synthesis of phenylene (N-hydroxyaniline) compounds under selenium catalysis

[0017] Replacing nitrobenzene with substituted nitrobenzene according to the method of Example 1. The results are summarized in table 1 in tabular form:

[0018]

[0019] Table 1: Synthesis of phenylene (N-hydroxyaniline) compounds under selenium catalysis

[0020]

Embodiment 3

[0021] Embodiment 3, taking the synthesis of phenylhydrazine (N-hydroxyaniline) as an example, the synthesis of phenylhydrazine (N-hydroxyaniline) under different reaction conditions such as reducing agent, temperature, solvent, and reaction time. The results are summarized in Table 2 in tabular form.

[0022] serial number

[0023] Reaction conditions: nitrobenzene 10mmol; sodium borohydride (potassium borohydride) 25mmol; selenium 0.5mmol; absolute ethanol 40mL; temperature 12-78°C; reaction time 0.25-3.0 hours; 2 O / THF is V H2O :V THF =0.5:40mL.

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Abstract

During the catalytic synthesis of phenylhydroxylamine compound, substituted nitrobenzene derivative as main material is reacted inside water or organic in the presence of reductant and selenium as catalyst. The substituting radical R in nitrobenzene derivative may be one or several kinds one electron donoring and / or electron accepting substituting radicals or hydrogen atom. The reductaant may be proton donoring reductant, and the catalyst has molar consumption in 0.1-20 % of substrate. The reacting substrate has molar ratio to the solvent of 1 to 1-100, and the solvent is one or several kinds polar or nonpolar solvent. The reaction time is 0.25-20 hr and the reaction temperature is 10-100 deg.c. The present invention has simple operation, easy-to-obtain material, less reaction steps and high yield.

Description

technical field [0001] The invention relates to a method for catalyzing and synthesizing phenylene compounds, in particular to a method for synthesizing benzene compounds under selenium catalysis. technical background [0002] Heterocyclic compounds containing -N-OH groups or aromatic compounds containing such groups as substituents can act as electron transfer carriers to promote polyphenol oxidase-laccase oxidation of non-phenolic lignin-type compounds or release of paper pulp Residual lignin in [Literature: Bourbonnais R, Paice MG, Freiermuth B.Appl.Environ.Microbil.1996, 63(12): 4627; Call H P.1994, WO94129510; Lai Z Y, Xu H, Wen X H. The 7 th international conference of biotechnology in pulp and paper industry. Vol.A. Proceeding Canada, 1998, A117; Amann M.9th International Symposium on Wood and Paper Chemistry, The Lignozym Process coming Closer to the Mill, 1997: F 4-1 -F 4-4 】. Therefore, the synthesis of such compounds is extremely valuable. Phenylbenzene is a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C239/08
Inventor 陈金铸陆世维
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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