Synthesis process of 1, 3, 5-triaminobenzene

A technology of triaminobenzene and synthesis process, which is applied in the field of synthesis of 1,3,5-triaminobenzene, can solve the problems of high equipment requirements, dangerous transportation and use, and is not easy to enlarge, and achieves a simple synthesis route and convenient post-processing. , easy to magnify effect

Inactive Publication Date: 2014-12-31
SUZHOU KANGRUN PHARMA
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Problems solved by technology

This method has the following disadvantages: (1) The raw material 1,3,5-trinitrobenzene or 3,5-dinitroaniline, or 2,4,6-trinitrophenol are highly explosive compounds, transportation and Dangerous to use; (2) Reduction needs to be carried out under high temperature and high pressure, which requires high equipment and high risk, and is not suitable for large-scale production
This method has the following problems: (1) The amount of sodium azide used is relatively large, which is both a highly explosive compound and a highly toxic compound; (2) The intermediate 1,3,5 triazidebenzene or 1,3 , 5-Benzoyl azide is easy to explode, making it difficult to operate and difficult to enlarge

Method used

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  • Synthesis process of 1, 3, 5-triaminobenzene

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Embodiment

[0014] The synthesis technique of 1,3,5-triaminobenzene, the steps are as follows:

[0015] Step 1: 1,3,5-Tri-Boc-aminobenzene

[0016] Diphenylphosphoryl azide (210 g, 764 mmol) was added in portions to trimesic acid (50 g, 238 mmol) and triethylamine (77.2 g, 764 mmol) in toluene (250 mL) and tert-butanol (150 mL) In the mixed solution, after the addition, the mixed solution is at 70 o C-90 o C stirred for 3-4 hours, then raised the temperature to 100 o C-120 o C and the reaction solution was stirred for 2 hours. After cooling down to room temperature, saturated sodium bicarbonate solution (400 mL) was added. The organic layer was separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over anhydrous sodium sulfate and pulled dry. Petroleum ether (200 mL) was added to the residue, stirred, and then filtered to obtain 1,3,5-tri-Boc-aminobenzene (89 g, 90%). This solid was directly used in the next step without puri...

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Abstract

The invention relates to a synthesis process of 1, 3, 5-triaminobenzene. The process is characterized by: taking trimesic acid and diphenylphosphoryl azide as reaction raw materials, and adopting toluene and tert-butyl alcohol (in a volume ratio of 5:3) as solvents, letting them react at 70DEG C-90DEG C for 3-4h, then raising the temperature to 100DEG C-120DEG C and leaving them to react for 2h, thus obtaining 1, 3 5-tri-Boc aminobenzene; and placing the 1, 3 5-tri-Boc aminobenzene into a mixed solution of ethanol and concentrated hydrochloric acid (in a volume ratio of 1:1) to be stirred overnight, thus obtaining the 1, 3, 5-triaminobenzene. The process provided in the invention is simple, needs no flammable and explosive reagent, the reaction conditions are mild, and the product yield is high.

Description

technical field [0001] The invention relates to a synthesis method of 1,3,5-triaminobenzene. Background technique [0002] 1,3,5-Triaminobenzene is a relatively important intermediate. Using it as the mother nucleus, a series of important compounds such as urea and amide can be produced after certain chemical reactions. These compounds are good nucleating agents and organic gel factors in the field of polymers ( polymer ,2007,48,1612; Adv. Funct. Mater , 2007, 17, 2349), and also has good electrical conductivity and photoresponse properties ( J. Mater. Chem. 2009,19,4495; Langmuir 2007, 23, 202) has also received extensive attention in the field of new materials. In recent years, some people have studied the use of 1,3,5-triaminobenzene and its derivatives as electrolyte or electrode additives or anion acceptors to improve and enhance various electromagnetic functions, and good progress has been made (WO2007126262 ). [0003] The synthesis of 1,3,5-triaminobenzen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/50C07C209/62
Inventor 郑晓圆徐卫良徐炜政
Owner SUZHOU KANGRUN PHARMA
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