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Bisglyoxaline organic phosphine compound and preparation method thereof

A biimidazole and compound technology is applied in the field of biimidazole organic phosphine derivative compounds and their synthesis, and achieves the effects of great significance, avoidance of loss and cost reduction

Inactive Publication Date: 2012-11-21
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are many studies on the reaction carried out in ionic liquids in the literature, but the functionalization of its chemical structure (such as: chirality, polarity, acidity, coordination ability, etc.), especially about the coordination functionalization of biimidazole There are relatively few research reports on ionic liquids

Method used

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  • Bisglyoxaline organic phosphine compound and preparation method thereof
  • Bisglyoxaline organic phosphine compound and preparation method thereof
  • Bisglyoxaline organic phosphine compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Take 0.8g (2.4mmol) of 1,1'-bis(ethyl propionate)-2,2'-biimidazole and dissolve it in 30ml of absolute ethanol. Add 0.9 g (24 mmol) sodium borohydride in batches under stirring; heat to reflux for 3 hours. The solvent was removed by rotary evaporation to obtain a white solid, which was dissolved in 3ml of water to obtain a colorless and transparent solution; the solution was adjusted to pH 8-9 with 1M hydrochloric acid solution, and the white turbidity appeared, and it was filtered to obtain a colorless and transparent solution; the solution was 5ml×3 Extract with dichloromethane, and combine the organic phases. The organic phase was dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and petroleum ether and ethyl acetate were recrystallized to obtain 0.53 g of white solid 1,1'-bis(3-hydroxypropyl)-2,2'-biimidazole, the yield : 89%. Melting point: 105-106°C. IR (KBr, cm -1 ) 3190 (br), 2874, 1466, 1429, 1367, 1273, 1146, 1063, 930,...

Embodiment 2

[0073] Take 1.5g (3.8mmol) of 1,1'-bis(butyl propionate)-2,2'-biimidazole and dissolve it in 60ml of absolute ethanol. Add 1.4 g (38 mmol) sodium borohydride in batches under stirring; heat to reflux for 3 hours. The solvent was removed by rotary evaporation to obtain a white solid, which was dissolved in 3ml of water to obtain a colorless and transparent solution; the solution was adjusted to pH 8-9 with 1M hydrochloric acid solution, and the white turbidity appeared, and it was filtered to obtain a colorless and transparent solution; the solution was 10ml×3 Extract with dichloromethane, and combine the organic phases. The organic phase was dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and petroleum ether and ethyl acetate were recrystallized to obtain 0.8 g of 1,1'-bis(3-hydroxypropyl)-2,2'-biimidazole as a white solid. The yield was : 83%. The spectrogram is the same as example 1.

Embodiment 3

[0075]Under an inert atmosphere, 2 g (6.5 mmol) of 1,1'-bis(methyl propionate)-2,2'-biimidazole was dissolved in 40 ml of anhydrous tetrahydrofuran. Add 1.5 g (39.5 mmol) lithium aluminum hydride in batches under stirring; heat to reflux for 5 hours. The solvent was removed by rotary evaporation, 20ml of water and 20ml of dichloromethane were added, the organic phase was separated after suction filtration, the aqueous solution was extracted with dichloromethane, and the organic phases were combined. The organic phase was dried with anhydrous magnesium sulfate, the solvent was removed by rotary evaporation, and petroleum ether and ethyl acetate were recrystallized to obtain 0.7g of white solid 1,1'-bis(3-hydroxypropyl)-2,2'-biimidazole, the yield : 44%. The spectrogram is the same as example 1.

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Abstract

The invention provides bisglyoxaline organic phosphine compound and preparation method thereof, characterized in that: the bisglyoxaline organic phosphine compound is represented by the following molecule formula, wherein X represents trivalent diphenyl phosphine group; quinquevalent vulcanized diphenyl phosphine group, oxidized diphenyl phosphine group; hydroxyl group; or chlorine group; when X is trivalent diphenyl phosphine group, the product is obtained by reduction reaction, halogenation reaction, necleophilic substitution reaction, when X is quinquevalent diphenyl vulcanized phosphine group or diphenyl oxide phosphine group, the product is obtained bby vulcanization reaction or oxidation reaction of bisglyoxaline trivalent diphenyl phosphine compound; the bisglyoxaline organic phosphine and its derivative react with transition metal and lanthanide series metal to form ligand compound and are applied for application domain such ash organic catalysis, rare earth metal extraction separation and the bisglyoxaline organic phosphine and its derivative are furthermore modified by quaternary ammoniation of the imino nitrongen on imidazole to obtain ion liquid paderial with functionalized ligand and the ligand ion liquid paderial is also applied for the above application fields.

Description

technical field [0001] The invention relates to biimidazole organic phosphine derivative compounds and their synthesis, in particular to the synthesis of biimidazole diphosphine, biimidazole diol and biimidazole dichloride. Background technique [0002] The excellent physical and chemical properties of ionic liquids did not receive enough attention in the early days, and the basic research and applied research were limited, and there were only some scattered and sporadic research in a narrow field. In the 1970s, Osteryoung et al. used N-alkylpyridine chloroaluminate ionic liquids when studying high-efficiency energy storage batteries; in the 1980s, Wilkes et al. found that 1,3-dialkylimidazoles Chloroaluminate has a more negative electrochemical reduction potential. An imidazole-based ionic liquid was synthesized and tried to replace traditional solvents and applied to organic synthesis; since Wilkes synthesized the first one that is stable to both water and air in 1992 Io...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/53C07F9/50
Inventor 梁洪泽张涛项建存汪可陈波王金龙
Owner NINGBO UNIV
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