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Method for performing dehalogenation reduction on multi-halogenated perylene diimide through cobalt catalyzing

A technology of polyhalogenated perylene diimides and substituted perylene diimides, which is applied in the field of cobalt-catalyzed dehalogenation and reduction of polyhalogenated perylene diimides, which can solve the problems of limited natural resources, high prices, and difficult recycling , to achieve the effect of cheap raw materials, easy operation, and efficient dehalogenation reduction

Active Publication Date: 2018-09-07
FUQING BRANCH OF FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this kind of method uses precious metals such as rhodium and palladium. These precious metals have very limited natural resources, are expensive, and difficult to recycle, so this kind of method is gradually abandoned by the industry.

Method used

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  • Method for performing dehalogenation reduction on multi-halogenated perylene diimide through cobalt catalyzing
  • Method for performing dehalogenation reduction on multi-halogenated perylene diimide through cobalt catalyzing
  • Method for performing dehalogenation reduction on multi-halogenated perylene diimide through cobalt catalyzing

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1. Preparation of compound 2a from tetrachloroperylene diimide

[0032] Under nitrogen protection, C was added successively to a 50 mL Schlenk reaction tube. 4 Alkyltetrachloroperylenediimide substrate (1.0mmol), cobalt dibromide (0.2mmol), manganese powder (6.0mmol), sodium formate (10.0mmol), N,N-dimethylacetamide (10.0 mL) and pyridine (10.0 mL), then heated to 100°C and reacted for 8 hours. After the reaction, it was naturally cooled to room temperature. The reaction mixture was slowly poured into 100 mL of saturated aqueous ammonium chloride solution to quench, fully stirred for 30 minutes, then extracted with 100 mL of dichloromethane, and the extraction was repeated three times. After drying over anhydrous sodium sulfate, the dichloromethane solvent was removed under reduced pressure on a rotary evaporator to obtain a concentrated mixture. The product was further purified by silica gel column chromatography, adsorbent: 300-400 mesh silica gel, eluent: ...

Embodiment 2

[0036] Example 2. Preparation of compound 2a from tetrabromoperylene diimide

[0037] The preparation method is basically the same as that of Example 1, except that the corresponding tetrachloroperylene diimide in Example 1 is replaced with the corresponding tetrabromo perylene diimide to obtain 0.457 g of compound 2a as a red solid (yield: 91 g). %).

[0038] Structural confirmation data for this product are shown below:

[0039] Mass spectrum: MS (MALDI-TOF): 502.2 (M + ).

[0040] NMR spectroscopy: 1 H NMR (400MHz, CDCl 3 )δ(ppm): δ=8.67(d,8H),4.17(t,4H),1.57–1.62(m,4H),1.17–1.20(m,4H),0.93(t,6H).

Embodiment 3

[0041] Example 3. Preparation of compound 2b from tetrachloroperylenediimide

[0042] The preparation method is basically the same as in Example 1, and the difference is: the C in Example 1 4 Alkyltetrachloroperylenediimide is replaced by C 6 Alkyl tetrachloroperylene diimide to obtain compound 2b as a red solid 0.508 g (yield: 91%).

[0043] Structural confirmation data for this product are shown below:

[0044] Mass spectrum: MS (MALDI-TOF): 558.3 ​​(M + ).

[0045] NMR spectroscopy: 1 H NMR (400MHz, CDCl 3 )δ(ppm): δ=8.68(d,8H),4.17(t,4H),1.57–1.63(m,4H),1.16–1.25(m,8H),0.91(t,6H).

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Abstract

The invention discloses a method for performing dehalogenation reduction on multi-halogenated perylene diimide through cobalt catalyzing. The method is characterized in that multi-halogenated perylenediimide arene is effectively subjected to dehalogenation reduction by one step in the presence of an organic solvent through an inert atmosphere reactor under a catalyzing system containing dibromo cobalt with a catalyzing quantity, excessive manganese powder and excessive sodium formate. According to the method, the synthesizing route has the advantages of being simple, efficient, low in price of raw materials, low in synthesizing cost, and high in repeatability and can be widely applied to dehalogenation reduction reaction of other halogenated aromatic hydrocarbons.

Description

technical field [0001] The invention relates to a method for dehalogenation and reduction of polyhalogenated perylene diimides catalyzed by cobalt. Background technique [0002] Perylene pigments belong to high-grade organic pigments. Among them, perylene pigments with perylene diimide as the parent structure are an important variety. These pigments have excellent light fastness and heat resistance, and are used in high-grade coatings, such as automobiles. Coatings, metal surface coatings, exterior wall coatings, etc. Halogenated perylene diimide, as an intermediate of perylene pigments, can be converted into perylene diimide derivatives with different substituents, so that the pigments have different color differences and greatly enrich the color of pigments. [0003] However, halogenated perylene diimides are extremely difficult to degrade naturally. Since the 1980s, the environmental hazards of large amounts of halogenated aromatic hydrocarbons have become increasingly ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06
CPCC07D471/06
Inventor 卢修强黄芝华陈国奋王昌伟姚忠亮林渊智
Owner FUQING BRANCH OF FUJIAN NORMAL UNIV