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A kind of quaternary ammonium salt functionalized porphyrin catalyst and preparation method thereof

A quaternary ammonium salt functional and catalyst technology, applied in chemical instruments and methods, organic chemistry, cobalt organic compounds, etc., can solve the problems of narrow molecular weight distribution of polymers and low molecular weight of copolymers, shorten the induction period and achieve good catalytic effect. , easy-to-type effects

Inactive Publication Date: 2017-05-17
WUHAN UNIV OF TECH
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

Compared with other catalysts, the advantage of porphyrin metal catalysts is that the molecular weight distribution of the polymer is narrow, and it can catalyze low-pressure polymerization. The disadvantage is that the catalyst must introduce cocatalysts, nucleophilic cocatalysts and carbonates initiated by axial ligands when catalyzing polymerization. The chain alternately grows and dissociates on both sides of the porphyrin metal complex, and the nucleophilic cocatalyst stabilizes the metal ions in the porphyrin metal catalyst, so that the polymerization reaction can proceed smoothly under a lower carbon dioxide pressure. , when the porphyrin catalyst system catalyzes polymerization, the polymerization activity needs to be improved, and the molecular weight of the copolymer is not high

Method used

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  • A kind of quaternary ammonium salt functionalized porphyrin catalyst and preparation method thereof
  • A kind of quaternary ammonium salt functionalized porphyrin catalyst and preparation method thereof
  • A kind of quaternary ammonium salt functionalized porphyrin catalyst and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]Catalyst preparation: Take 4.98g (46.9mmol) of benzaldehyde, 3.8g salicylaldehyde (31.3mmol) and 4.2g pyrrole (62.6mmol) (benzaldehyde: salicylaldehyde: pyrrole = 3:2:4, molar ratio) and weigh After measuring, add solvent 150mL propionic acid, reflux reaction at 130-150°C for 4h, concentrate propionic acid to 75mL, add 75mL anhydrous methanol, put in refrigerator at 0°C for 24h, filter, and dry the precipitate in vacuum , after separation by silica gel column chromatography, 5-o-hydroxyphenyl-10,15,20-triphenylporphyrin ((OH)TPPH 2 )), 1.008g (OH)TPPH 2 (1.6mmol), 0.158g 1,2-dichloroethane and excess anhydrous potassium carbonate 1.104g ((OH)TPPH 2 : 1,2-dichloroethane:anhydrous potassium carbonate=1:1:5, molar ratio) was added into 100mL N,N-dimethylformamide (DMF), reacted at room temperature for 48h, removed the solvent, added 100mL Dichloromethane is also filtered, and the filtrate is extracted with water for 3-5 times, the organic liquid is taken, the solvent is r...

Embodiment 2

[0035] Prepare catalyst: reactant p-methoxybenzaldehyde 6.38g (46.9mmol), 3.8g salicylaldehyde (31.3mmol) and 4.2g pyrrole (62.6mmol) (benzaldehyde: salicylaldehyde: pyrrole=3:2: 4, (molar ratio)) After weighing, add solvent 150mL propionic acid, reflux at 130-150°C for 6h to obtain crude product, concentrate propionic acid to 75mL, add 75mL anhydrous methanol, place in refrigerator at 0°C Set aside for 24h, filtered, the precipitate was vacuum-dried, and separated by silica gel column chromatography to obtain 5-o-hydroxyphenyl-10,15,20-tri-p-methoxyphenylporphyrin (CH 3 O) 3 (OH)TPPH 2 , 1.15g (CH 3 O) 3 (OH)TPPH 2 (1.6mmol), 0.203g 1,4-dichlorobutane and excess anhydrous potassium carbonate 1.1g ((CH 3 O) 3 (OH)TPPH 2 : 1,4-dichlorobutane:potassium carbonate=1:1:5, molar ratio) was added into 100mL N,N-dimethylformamide (DMF), reacted at room temperature for 48h, removed the solvent, added 100mL dichloro methane and filtered, the filtrate was extracted with water for...

Embodiment 3

[0040] Catalyst preparation: the same method as in Example 1 was used to prepare 5-o-hydroxyphenyl-10,15,20-phenylporphyrin ((OH)TPPH 2 ), the 1.008g (OH) TPPH 2 (1.6mmol), 0.39g 1,6-dibromohexane and excess anhydrous potassium carbonate 1.1g ((OH)TPPH 2 : 1,6-dibromohexane:potassium carbonate=1:1:5, molar ratio) was added into 100mL N,N-dimethylformamide (DMF), reacted at room temperature for 48h, removed the solvent, added 100mL dichloro methane and filtered, the filtrate was extracted with water for 3-5 times, the organic liquid was taken, the solvent was removed, and the bromoporphyrin (O(CH 2 ) 6 Br)TPPH 2 ; Take 1.141g (O(CH 2 ) 6 Br)TPPH 2 (1.44mmol), 0.342g pyridine are dissolved in the mixed solvent 50mL of chloroform and acetonitrile (the volume ratio of chloroform and acetonitrile is 1:1, (O(CH 2 ) 6 Br)TPPH 2 The mol ratio with pyridine is 1:3), reflux reaction 96h, evaporate to dryness and separate through silica gel column chromatography to obtain pyridi...

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Abstract

The invention relates to a quaternary ammonium salt functionalized porphyrin catalyst and a preparation method thereof. The preparation method comprises the steps of reacting substituent-containing benzaldehyde and salicylaldehyde with pyrrole to prepare phenolic functionalized porphyrin, then undergoing a reaction with dihalogenated alkane to prepare halogenated porphyrin, reacting the prepared halogenated porphyrin with alkaline compounds (triethylamine, tributylamine and pyridine and the like) to prepare quaternary ammonium salt modified porphyrin; performing complexing of the prepared quaternary ammonium salt modified porphyrin and metals, and obtaining a quaternary ammonium salt functionalized porphyrin M (M=Co, Cr and Al) catalyst through oxidation. The obtained catalyst can be used for the copolymerization reaction of carbon dioxide and propylene oxide, aliphatic polycarbonate with a high molecular weight is obtained, the number-average molecular weight of the aliphatic polycarbonate is 15000-40000, the molecular weight distribution is 1.25-1.4, the carbon dioxide fixed rate is 39-43wt%, and the molar content of a carbonic ester chain segment in a polymerization product is 85-99%.

Description

technical field [0001] The invention relates to a quaternary ammonium salt functionalized porphyrin metal catalyst for the copolymerization of carbon dioxide and propylene oxide and a preparation method thereof. Background technique [0002] Due to the burning of fossil fuels in the production process of thermal power generation, steelmaking, oil refining, cement, etc., a large amount of carbon dioxide is emitted, and the resulting greenhouse effect has constituted increasingly serious environmental pollution. Therefore, carbon dioxide is considered an "environmental hazard". gas. But on the other hand, carbon dioxide is a resource that can be used under certain conditions. One of the main directions of using carbon dioxide is to synthesize polymer materials from it. Carbon dioxide copolymers (aliphatic polycarbonates) with highly alternating structures can be synthesized from carbon dioxide and epoxy compounds. Due to the presence of ester bonds in the main chain, the po...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G64/34C07F15/06C07F11/00C07F5/06
Inventor 谢东陈琪柳雷曾诚
Owner WUHAN UNIV OF TECH
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