A kind of method of olefin hydroformylation reaction in ionic liquid solvent

An ionic liquid solvent and ionic liquid technology, applied in carbon monoxide reaction preparation, chemical instruments and methods, organic chemistry, etc., to achieve high yield, low dosage and high conversion rate

Active Publication Date: 2011-11-30
INST OF PROCESS ENG CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This reaction system is mainly used in reactions where the reaction substrate is...

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  • A kind of method of olefin hydroformylation reaction in ionic liquid solvent
  • A kind of method of olefin hydroformylation reaction in ionic liquid solvent
  • A kind of method of olefin hydroformylation reaction in ionic liquid solvent

Examples

Experimental program
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Effect test

Embodiment 1

[0026] 0.0078g (about 0.03mmol) Rh(CO) 2 acac catalyst, 0.0786g (about 0.3mmol) triphenylphosphine, 10mL of degassed toluene, added to a self-made 200mL stainless steel reactor with a polytetrafluoroethylene liner, nitrogen replacement 3 times at room temperature, filled with mole than C 2 h 4 :CO:H 2 1:1:1 to 2.0MPa. React at 100°C for 2 hours, cool to room temperature and release unreacted gas, the prepared propionaldehyde and other by-products are analyzed by gas chromatography, the experimental results are shown in Table 1.

Embodiment 2

[0036] HRh(CO)(PPh 3 ) 3 Catalyst preparation

[0037] Place 0.527g (2mmol) of triphenylphosphine in a 50ml three-necked flask equipped with a condenser, vacuumize and fill with nitrogen three times to make it an inert and oxygen-free environment. Use a pipette needle to add 20ml of absolute ethanol to it, stir and heat to reflux (70°C), add a solution of 0.0527g (0.2mmol) RhCl 3 · 3H2O in 4ml ethanol solution, stirred rapidly for 15 seconds, turned into (deep red solution). Add 2ml of 40% formaldehyde solution, the dark red solution becomes lighter. Then heat 4ml of absolute ethanol dissolved with 0.16g KOH until it is about to boil, then use a pipette needle to add to the reaction solution, within 3 minutes the deep red solution gradually turns yellow, reflux for 10 minutes, cool to room temperature, and yellow precipitates powdery solid. Use a pipette needle to remove the liquid-phase solvent, wash the solid product with 10ml of absolute ethanol and 10ml of distilled w...

Embodiment 3

[0046] Catalyst, raw material, ionic liquid and reaction condition identical with comparative example 6, just use ionic liquid [Bmim] [BF 4 ] replaced with [Bmmim][BF 4 ] to prepare propionaldehyde, the experimental results are shown in Table 1.

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Abstract

The invention discloses a method for generating corresponding arabino compounds through hydroformylation of light olefin compounds, carbon monoxide and hydrogen under proper temperature and pressure conditions by taking imidazole, bis-imidazole, quaternary phosphonium, quaternary amine or guanidine ionic liquid as a solvent in the presence of a noble metal complex catalyst and a phosphine ligand system. The ionic liquid solvent is interacted with an Rh catalyst in reaction or forms a novel complex, the formation of a low-activity Rh cluster compound is inhibited, the structure of the Rh catalyst is stabilized, and the activity and stability of the catalyst are improved. After the hydroformylation is finished, most products are separated through simple flashing; and the flashed ionic liquid and homogeneous complex catalyst can be circularly used for the hydroformylation. The method has the advantages of environmental friendliness, simple process and the like.

Description

technical field [0001] The invention relates to a noble metal complex catalyst and a phosphine ligand system, using imidazoles, bisimidazoles, quaternary phosphoniums, quaternary ammoniums or guanidine ionic liquids as solvents, in the presence of a certain amount of corresponding product aldehydes and Under certain temperature and pressure conditions, low-carbon olefin compounds, carbon monoxide and hydrogen undergo hydroformylation reactions to generate corresponding aldehyde compounds. The invention belongs to the field of organic compound preparation methods. Background technique [0002] The use of olefinic compounds, carbon monoxide and hydrogen in the presence of a catalyst system comprising a Group 8, 9 or 10 metal such as Rh and a phosphine ligand such as an alkylphosphine, cycloalkylphosphine, arylphosphine, pyridylphosphine or bidentate phosphine The hydroformylation reaction has been described in many patents and documents, such as US2003092935A1; US2004110960A1...

Claims

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Application Information

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IPC IPC(8): C07C47/02C07C45/50B01J31/24C07F15/00
CPCY02P20/54Y02P20/584
Inventor 张锁江刁琰琰李靖闫瑞一杨普王玲王蕾
Owner INST OF PROCESS ENG CHINESE ACAD OF SCI
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