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Process for synthesizing tetra-substituted amino macrocyclic metal complex

A technology of metal complexes and synthesis methods, applied in the direction of copper organic compounds, zinc organic compounds, iron organic compounds, etc., can solve the problems of complex synthesis routes, harsh reaction conditions, and large solvent consumption, and achieve simple processes and low solvent usage The effect of reducing and reducing pollution

Inactive Publication Date: 2008-06-11
吾国强
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The synthetic route is relatively complicated and consists of four steps, as shown in the figure above
Among them, the reaction of obtaining D by chlorination, the reagents such as phosphorus trichloride, phosphorus pentachloride and thionyl chloride used have great environmental pollution; the reaction of obtaining E by cyclization needs to be carried out in a very dilute solution, and the solvent consumption It is very large, and the reaction yield is only 30%; the reaction to generate F requires the use of n-butyllithium reagent, the reaction conditions are harsh, and the cost is high, making it difficult to realize industrialization

Method used

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  • Process for synthesizing tetra-substituted amino macrocyclic metal complex
  • Process for synthesizing tetra-substituted amino macrocyclic metal complex
  • Process for synthesizing tetra-substituted amino macrocyclic metal complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 40ml of acetone solvent, 6ml of oxalyl chloride and 12ml of triethylamine into a 125ml three-necked flask, and protect it with nitrogen gas. 10 g of glycine starting material was added in batches over two hours and cooled with an ice bath. After reacting for 4h, it was filtered to obtain a solid. Put the solid in ice water, stir for a period of time, filter, dissolve the filter cake in sodium hydroxide solution, remove insoluble matter, add hydrochloric acid and precipitate the product, and finally wash with 3*100ml distilled water to obtain 10.9g of oxalylamino di Acetic acid intermediate product I, yield 80.2%;

[0033] Then, in a 125ml three-necked flask, 10g of oxalylaminodiacetic acid intermediate I was added as a raw material and 35g of bis(trichloromethyl)carbonate, heated, stirred, and refluxed for 3 hours. After the reaction, cool down, add 50ml of toluene, distill in a rotary evaporator, wash with 3*20ml of chloroform, and dry to obtain 10.8g of oxalylam...

Embodiment 2

[0036] According to the same synthesis steps as in Example 1, 40 ml of acetone, 7 ml of malonyl chloride and 12 ml of triethylamine were added to a 125 ml three-necked flask, and nitrogen protection was carried out. 10 g of glycine was added in batches within two hours to obtain 11.9 g of malonylaminodiacetic acid intermediate I, with a yield of 82.1%;

[0037] In a 125ml three-necked flask, 10g of malonylaminodiacetic acid and 33g of bis(trichloromethyl)carbonate were added, and dried to obtain 10.6g of malonylaminodiacetyl chloride intermediate II, with a yield of 90.6%;

[0038] Add 2.5g of malonylaminodiacetyl chloride, 1.7g of copper chloride and 7.5ml of acetone into a 250ml three-necked flask, protect with nitrogen, and cool with an ice bath. Put 1.1g of o-phenylenediamine, 7ml of acetone and 10ml of triethylamine into a constant pressure funnel to finally obtain 2.9g of the resultant product III of the tetraaminomacrocyclic ligand Cu complex, with a yield of 78.4%.

Embodiment 3～7

[0040] According to the same synthetic steps of Example 1, wherein the raw materials, reaction materials and auxiliary materials, the reaction conditions are as listed in the table:

[0041] Example

[0042] 3: raw material (wt)

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Abstract

This invention is about the synthesis of the four-amidol-macrocyclic complex. The original source amino acid reacts with dichloride to produce diamido diacid with the existenc of organic solvent alkali or nitrogen. The diamido diacid could react with chlorizating agent to produce diamido diachlorid. Finally, diamido diachlorid and its derivative react with metallic ion, with he existenc of organic solvent alkali or nitrogen, could produce four-amidol-macrocyclic complex. This invention is advantageous in simplified process, higher selective, production efficiency and easy-industralization.

Description

technical field [0001] The invention relates to the preparation of tetraaminomacrocyclic ligand metal complexes, and in particular provides a synthesis method of tetraaminomacrocyclic ligand metal complexes. Background technique [0002] Tetraaminomacrocyclic ligand metal complexes can be used as oxidation catalysts, which can activate "green" oxidants such as hydrogen peroxide and oxygen in acidic, neutral and alkaline aqueous solutions, and are used in textile bleaching, wood pulp bleaching, printing and dyeing wastewater treatment and Organic synthesis and many other fields. The patent documents of WO98 / 03263, US5298618, US6127536, US6384279 and US5853428 relate to various synthesis methods of tetraamino macrocyclic ligands. Wherein, with the method that US6051704 provides and the compound closest to the present invention: [0003] The synthetic route of 5,6-Benzo-3,8,11,13-tetraoxo-2,2,9,9,12,12-hexmethyl-1,4,7,10-tetraazacyclotridecane is as follows: [0004] [0...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/03C07F15/06C07F1/08C07F3/06C07F15/04C07F11/00C07D257/00
Inventor 吾国强雷宏冯晓亮吕延文
Owner 吾国强