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Method for synthesizing valeraldehyde

A technology of valeraldehyde and mixed gas, applied in chemical instruments and methods, preparation of organic compounds, preparation of carbon-based compounds, etc., can solve the problems of limited industrial application process, harsh reaction conditions, high price, etc., and achieve high industrial application prospects , The synthesis process is simple and the conditions are mild

Active Publication Date: 2021-03-09
上海簇睿低碳能源技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] As a noble metal, rhodium is expensive, which leads to an increase in the cost of NHC-Rh catalysts, which limits its further industrial application process. Compared with rhodium, cobalt is cheaper, and the complex formed after coordinating with carbene can be used as hydrogen Catalysts in formylation reactions
[0013] The hydroformylation of butene based on phosphine ligands has achieved very good results, but the synthesis of efficient phosphine ligands usually requires harsh reaction conditions and highly toxic reagents, which has led to a change in the cost of the synthesis process of phosphine ligands. High, but there are also challenges in security

Method used

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  • Method for synthesizing valeraldehyde
  • Method for synthesizing valeraldehyde
  • Method for synthesizing valeraldehyde

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] Add 0.04mmol of cobalt complex (19.4mg) catalyst 1 into a 100mL reactor, add 40mL of toluene solvent and use CO / H 2 Mixed gas (molar ratio 1:1) was used to replace the reactor. After three replacements, 20 mmol (1.72 g) of n-butene was added. After adding n-butene, CO / H with a molar ratio of 1:1 was charged. 2 Mix gas to 2MPa, and react at 110°C. After 24 hours, the reaction was completed, the reaction kettle was cooled, and the residual gas was released carefully under ventilated conditions. An internal standard was added to the solution after the reaction, and gas chromatography analysis was carried out. The yield of n-valeraldehyde obtained was 21%, and n-butene The conversion rate was 28%, and the positive-to-differential ratio was 3:1.

Embodiment 2

[0036]

[0037] Add 0.025mmol of cobalt complex (16.98mg) catalyst 2 into a 100mL reactor, add 40mL of toluene solvent and use CO / H 2 Mixed gas (molar ratio 1:1) was used to replace the reactor. After three replacements, 20mmol (1.72g) of n-butene was added. After adding n-butene, CO / H with a molar ratio of 1:1 was charged. 2Mix gas to 3MPa, and react at 120°C. After 24 hours, the reaction was completed, the reaction kettle was cooled, and the residual gas was released carefully under ventilated conditions. An internal standard was added to the solution after the reaction, and gas chromatography analysis was carried out. The yield of n-valeraldehyde obtained was 36%, and n-butene The conversion rate was 45%, and the positive-to-isotropic ratio was 3.8:1.

Embodiment 3

[0039]

[0040] Add 0.02mmol of cobalt complex (15.92mg) catalyst 3 into a 100mL reaction kettle, add 40mL of toluene solvent and use CO / H 2 Mixed gas (molar ratio 1:1) was used to replace the reactor. After three replacements, 20 mmol (1.72 g) of n-butene was added. After adding n-butene, CO / H with a molar ratio of 1:1 was charged. 2 Mixed gas to 3MPa, react at 140°C. After 36 hours, the reaction was finished, and the reaction kettle was cooled, and the remaining gas was released carefully under ventilated conditions. An internal standard was added to the solution after the reaction, and gas chromatography analysis was carried out. The yield of n-valeraldehyde obtained was 61%, and n-butene The conversion rate is 70%, and the positive-to-isotropic ratio is 6:1.

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Abstract

The invention discloses a method for synthesizing valeraldehyde, which is characterized by comprising the following steps: adding a catalyst and an organic solvent into a reaction kettle, adding n-butene in a closed state, and introducing a mixed gas of CO and H2; heating the reaction kettle for reaction; wherein the catalyst is an N-heterocyclic carbene cobalt complex. Compared with the prior art, the N-heterocyclic carbene cobalt complex can be prepared by using a direct and rapid method, meanwhile, reagents with strong toxicity are not used, and the conditions are mild, so that the N-heterocyclic carbene cobalt complex is a good alternative reaction system of a phosphine ligand catalytic system; the method is simple in synthesis process and low in cost, and has a relatively high industrial application prospect.

Description

technical field [0001] The present invention relates to a preparation method of an azacyclic carbene cobalt complex catalyst, more specifically, applying azacyclic carbene cobalt metal complexes of different substituents or structural types in the hydroformylation reaction of butene, The invention belongs to the technical field of metal organic and homogeneous catalysis. Background technique [0002] In the hydroformylation reaction process, the choice of catalyst system is very important. Since Otto Roelen discovered the hydroformylation reaction of olefins in 1938, the hydroformylation catalytic system has experienced a high-pressure cobalt carbonyl catalytic system, triphenylphosphine Modified rhodium carbonyl low-pressure catalytic system, water-soluble rhodium-phosphine complex catalytic system, and the current rhodium bisphosphine ligand catalytic system. The introduction of the phosphine ligand greatly enhances the effect of the hydroformylation reaction. Therefore, ...

Claims

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Application Information

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IPC IPC(8): C07C47/02C07C45/50
CPCC07C45/505C07C47/02Y02P20/584
Inventor 孙予罕王慧宋文越马春辉杜洋王栋梁袁湘琦
Owner 上海簇睿低碳能源技术有限公司
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