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Method for preparing butyraldehyde through propylene hydroformylation

A technology for propylene hydroformylation and butyraldehyde is applied in the field of propylene hydroformylation to prepare butyraldehyde, and can solve the problems of complex preparation process, high price, and few applications of BISBI.

Inactive Publication Date: 2016-11-09
成都欣华源科技有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the complex preparation process and high price of BISBI, it is rarely used

Method used

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  • Method for preparing butyraldehyde through propylene hydroformylation
  • Method for preparing butyraldehyde through propylene hydroformylation
  • Method for preparing butyraldehyde through propylene hydroformylation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] 100g of toluene, the molar concentration is 1.5×10 -3 Mole / L rhodium catalyst HRh(CO)(TPP) 3 , 6×10 -2 Mol / L bisphosphine ligand BISBI, 3×10 -3 Mole / L of TPP, put it into a 250 ml autoclave with a stirrer, use H in the autoclave 2 : Replace the syngas with CO=1:1 (molar ratio) for 3 to 5 times, then add 27 grams of propylene, and then add syngas to the total pressure in the kettle to 1.6MPa, and react for 1 hour at a reaction temperature of 85°C and a stirring speed of 200rpm After cooling to room temperature and releasing unreacted gas, the reaction solution was analyzed by gas chromatography, and the conversion rate of propylene was 85%, and the selectivity of butyraldehyde produced was 98%, among which n-butyraldehyde and isobutyraldehyde The molar ratio is 25:1.

Embodiment 2

[0047] 125 grams of anisole, the molar concentration is 2×10 -3 Mole / L rhodium catalyst RhCl(CO)(TPP) 2 , 4×10 -2 Mol / l BISBI, 6×10 -3 Mole / L of TPP was added to a 250 ml autoclave with a stirrer, and H was used in the autoclave 2 : CO=1:1 (molar ratio) syngas replacement 3 to 5 times, then add 30 grams of propylene, then add syngas to the total pressure in the kettle to 1.8MPa, react at a reaction temperature of 90°C and a stirring speed of 200rpm for 1 hour, After the reaction liquid in the autoclave was cooled to room temperature, unreacted gas was released. The reaction liquid was taken out and analyzed by gas chromatography. The conversion rate of propylene was determined to be 94%, and the selectivity to butyraldehyde was 97%. The molar ratio with isobutyraldehyde is 21:1.

Embodiment 3

[0049] Put 100 grams of n-butyraldehyde with a molar concentration of 2.5×10 -3 Mol / L rhodium catalyst Rh(CO) 2 (acac), 8×10 -3 Mole / L BISBI, 5×10 -2 Mole / L of TPP was added to a 250 ml autoclave with a stirrer, and H was used in the autoclave 2 : CO=1:1 (molar ratio) syngas replacement 3 to 5 times, then add 40 grams of propylene, then add syngas to the total pressure in the kettle to 2.0MPa, react at a reaction temperature of 100°C and a stirring speed of 200rpm for 1 hour, After the reaction liquid in the autoclave was cooled to room temperature, unreacted gas was released. The reaction liquid was taken out and analyzed by gas chromatography. The conversion rate of propylene was calculated to be 96%, and the selectivity to butyraldehyde was 97%. The ratio of butyraldehyde is 15:1.

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Abstract

The invention relates to a method for preparing butyraldehyde through propylene hydroformylation. The method is characterized in that a rhodium-phosphine complex, a composite catalyst system composed of bidentate phosphine 2,2'-bi(diphenylphosphinomethyl)-1,1'-biphenyl (BISBI) and triphenylphosphine (TPP) and a compound of methylbenzene or n-butyraldehyde or anisole are used as solvents, the solvents are added into a high-pressure reaction kettle, replacement is conducted 3-5 times with synthesis gas, then propylene and the synthesis gas (the molar ratio of H2 to CO is 1:1) are subjected to hydroformylation for preparing butyraldehyde under the stirring conditions that the total pressure ranges from 1 MPa to 3 MPa and the temperature ranges from 80 DEG C to 130 DEG C, the selectivity of generated butyraldehyde reaches 97% or above, the ratio of generated n-butyraldehyde to isobutyraldehyde can be regulated within the range of 9:1 to 30:1 by regulating the molar ratio of BISBI to TPP, the rhodium catalyst and the reaction product are subjected to reduced pressure distillation under the protection of the synthesis gas, and the rhodium catalyst is recovered and returned to the reaction kettle for recycling.

Description

technical field [0001] The invention relates to the technical field of preparation of petrochemical products, in particular to a method for preparing butyraldehyde by hydroformylation of propylene. Background technique [0002] The hydroformylation of olefins to aldehydes is one of the most important reactions in the production of petrochemical products. Butyraldehyde is produced by hydroformylation of propylene, butanol is produced by hydrogenation of butyraldehyde, and iso-octanol is produced by condensation and hydrogenation of butyraldehyde, which is the main way for industrial production of butanol and octanol. Ten million tons. The earliest use of propylene hydroformylation to produce butyraldehyde is cobalt carbonyl catalyst, and the reaction should be carried out under high temperature and high pressure. Aldehyde selectivity is only 80%, butanol selectivity is 10%. HCo(CO) modified with tertiary phosphine 3 (PR 3 ) cobalt catalyst, although the total pressure dr...

Claims

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Application Information

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IPC IPC(8): C07C47/02C07C45/50B01J31/24
CPCC07C45/505B01J31/2409B01J2231/40B01J2531/0213B01J2531/822
Inventor 陈华李贤均黎耀忠袁茂林王勇兰小航
Owner 成都欣华源科技有限责任公司
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