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Method for preparing aldehyde compounds through olefin two-phase hydroformylation

An aldehyde compound and hydroformyl technology, applied in the field of aldehyde synthesis, can solve the problems of poor catalyst recycling rate, harsh reaction conditions, low selectivity, etc., and achieve the effects of high conversion rate, improved reaction activity and high selectivity

Active Publication Date: 2021-04-20
SICHUAN UNIV +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the above-mentioned deficiencies or defects, the purpose of the present invention is to provide a method for preparing aldehyde compounds by two-phase hydroformylation of olefins, which can effectively solve the problems of harsh reaction conditions and low selectivity in the existing hydroformylation technology. , low conversion rate, poor catalyst recycling rate and unsuitable for hydroformylation of long-chain high-carbon olefins (≥C6)

Method used

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  • Method for preparing aldehyde compounds through olefin two-phase hydroformylation
  • Method for preparing aldehyde compounds through olefin two-phase hydroformylation
  • Method for preparing aldehyde compounds through olefin two-phase hydroformylation

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Embodiment 1

[0026] This embodiment 1 provides a method for preparing aldehydes by two-phase hydroformylation of olefins, the specific process is: 0.03 grams of rhodium catalyst HRh (CO) (TPPTS) 3 , 0.05 g of TPPTS, 6 mL of formamide and 2.5 mL of 1-octene were added to a stainless steel autoclave with a magnetic stirrer and a temperature controller, and then the synthesis gas was introduced into the autoclave to replace the air in the autoclave, and repeated for 3 Once, then fill the synthesis gas with the pressure ratio of hydrogen and carbon monoxide at 1:1 to 1MPa, raise the temperature to 70°C, then react at constant temperature and pressure at a stirring speed of 1000rpm for 2 hours, cool to room temperature, release the pressure, and separate the mixture immediately after taking it out. It consists of upper and lower layers, and the composition of the upper layer is analyzed by gas chromatography. It is calculated that the conversion rate of 1-octene is 97.3%, the selectivity of nona...

Embodiment 2

[0028] This embodiment 2 provides a method for preparing aldehyde compounds by two-phase hydroformylation of olefins, the specific process is: 0.03 gram of rhodium catalyst HRh (CO) (TPPTS) 3 , 0.05 grams of TPPTS, 6 mL of water and 2.5 mL of 1-octene were added to a stainless steel autoclave with a magnetic stirrer and a temperature controller, and then the air in the autoclave was replaced by synthesis gas, repeated 3 times , then filled with synthesis gas with a pressure ratio of hydrogen and carbon monoxide of 1:1 to 1MPa, heated to 70°C, then reacted at a constant temperature and pressure at a stirring speed of 1000rpm for 2 hours, cooled to room temperature, and released the pressure. After the mixture was taken out, it was divided into There are two upper and lower layers, and the composition of the upper layer is analyzed by gas chromatography. After calculation, the conversion rate of 1-octene is 20.4%, the selectivity of nonanal is 50.7%, and the selectivity of linear...

Embodiment 3

[0030] This embodiment 3 provides a method for preparing aldehydes by two-phase hydroformylation of olefins, the specific process is: 0.03 grams of rhodium catalyst RhCl (CO) (TPPTS) 2 , 0.13 g of TPPTS, 12 mL of formamide and 3.6 mL of 1-octene were added to a stainless steel autoclave with a magnetic stirrer and a temperature controller, and then the synthesis gas was introduced into the autoclave to replace the air in the autoclave, and repeated for 3 Once, then fill the synthetic gas with the pressure ratio of hydrogen and carbon monoxide at 1:1 to 2MPa, raise the temperature to 60°C, then react at constant temperature and pressure with a stirring speed of 1000rpm for 2.5 hours, cool to room temperature, release the pressure, and separate the mixture immediately after taking it out. It consists of upper and lower layers, and the composition of the upper layer is analyzed by gas chromatography. It is calculated that the conversion rate of 1-octene is 95.8%, the selectivity o...

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Abstract

The invention discloses a method for preparing an aldehyde compound by olefin two-phase hydroformylation, and belongs to the technical field of aldehyde synthesis. The method comprises the following steps: forming a catalytic system by using a water-soluble phosphine ligand and a rhodium catalyst, and synthesizing the aldehyde compound by using cheap and accessible high-polarity formamide, N-methylformamide, N, N-dimethylformamide and the like as solvents; enabling olefin and H2 / CO synthesis gas to be subjected to hydroformylation reaction to generate aldehyde. Due to the fact that the solubility of olefin in a high-polarity organic solvent is much higher than that of olefin in water, the reaction activity is greatly improved compared with that of water-oil two-phase hydroformylation; after the reaction is finished, the system is subjected to automatic phase splitting, the upper layer is a small-polarity product aldehyde, the lower layer is a large-polarity solvent phase, a water-soluble catalyst is dissolved in the large-polarity solvent phase, and repeated cyclic utilization of the catalyst can be realized through liquid splitting operation; the method has the characteristics of mild reaction conditions, high selectivity and high conversion rate, and the catalyst can be recycled for a long time and has an excellent industrial application prospect.

Description

technical field [0001] The invention relates to the technical field of aldehyde synthesis, in particular to a method for preparing aldehyde compounds by two-phase hydroformylation of olefins. Background technique [0002] Hydroformylation is one of the most widely used homogeneous catalytic reactions in industry. The product aldehyde is an important chemical raw material, its hydrogenation can produce alcohol, alcohol can be further prepared into cosmetics, skin care products, detergents, plasticizers, surfactants, etc., aldehyde can be further converted into carboxylic acid, ester, amine Wait. In addition to long-chain aldehydes, aldehydes produced by the hydroformylation of some special olefins such as styrene are also very important chemical structural units, and are often used as intermediates in the synthesis of fine chemicals and pharmaceuticals. And for cyclic dienes, their reactivity is much lower than that of chain olefins, but the dialdehyde products produced by ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/50C07C47/02
CPCY02P20/584
Inventor 郑学丽陈华易继伟付海燕袁茂林李瑞祥
Owner SICHUAN UNIV
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