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A kind of method for preparing γ-ketene from α,γ-unsaturated dienone

A technology of unsaturated and dienone, which is applied in the field of preparation of γ-enone, can solve the problems of high selectivity and yield of the target product, large amount of catalyst used, complicated operation, etc., and achieve high selectivity and yield, and catalyst use The effect of small amount and simple operation

Active Publication Date: 2022-08-05
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It solves the shortcomings of large amount of catalyst used, high cost, and complicated operation in the prior art, and can realize the silicon hydrogen reduction of α, γ-unsaturated dienone to obtain γ-enone and the reaction operation with a catalyst with low cost and small amount Simple, target product selectivity and high yield

Method used

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  • A kind of method for preparing γ-ketene from α,γ-unsaturated dienone
  • A kind of method for preparing γ-ketene from α,γ-unsaturated dienone
  • A kind of method for preparing γ-ketene from α,γ-unsaturated dienone

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Experimental program
Comparison scheme
Effect test

Embodiment 1-18

[0039]Selective hydrogenation of β-ionone to synthesize dihydroβ-ionone:

[0040] A 500 mL autoclave was charged with tetrakis(triphenylphosphine) palladium (176.87 mg, 0.15 mmol), triethoxysilane (55.32 g, 0.33 mol), and lanthanum trifluoromethanesulfonate (358.84 mg, 0.6 mmol) and tetrahydrofuran (176.60 g), the reaction kettle was sealed and replaced three times with nitrogen, and the nitrogen pressure in the reaction kettle was 0 MPa (gauge pressure). Under nitrogen protection, β-ionone (58.87g, 0.3mol) was pumped into the autoclave with an advection pump, and the stirring device and heating device of the autoclave were turned on. When the temperature in the autoclave reached 40°C, the timing was started. , the reaction was incubated for 3 hours, the samples were taken for analysis, and the conversion rate of β-ionone and the selectivity of dihydroβ-ionone were detected by GC.

[0041] When carrying out Example 2-6, the monohydrosilane was triethoxysilane, the solvent was...

Embodiment 19

[0048] Selective hydrogenation of β-ionone to synthesize dihydroβ-ionone:

[0049] A 1000 mL autoclave was charged with tetrakis(triphenylphosphine)palladium (35.37 mg, 0.03 mmol), triethoxysilane (150.8 g, 0.9 mol), and lanthanum trifluoromethanesulfonate (897.11 mg, 1.5 mmol) and tetrahydrofuran (176.60 g), the reaction kettle was sealed and replaced three times with nitrogen, and the nitrogen pressure in the reaction kettle was 0 MPa (gauge pressure). Under nitrogen protection, β-ionone (58.87g, 0.3mol) was pumped into the autoclave with an advection pump, and the stirring device and the heating device of the autoclave were turned on. The reaction was incubated for 6 hours, the samples were taken for analysis, and the conversion rate of β-ionone was 98.92%, and the selectivity of dihydroβ-rowanone was 98.19% by GC detection.

Embodiment 20

[0051] Selective hydrogenation of β-ionone to synthesize dihydroβ-ionone:

[0052] A 1000 mL autoclave was charged with tetrakis(triphenylphosphine)palladium (353.75 mg, 0.3 mmol), triethoxysilane (50.29 g, 0.3 mol), and lanthanum trifluoromethanesulfonate (179.42 mg, 0.3 mmol) and tetrahydrofuran (294.34g), the reaction kettle was sealed and replaced with nitrogen three times, and the nitrogen pressure in the reaction kettle was 0MPa (gauge pressure). Under nitrogen protection, β-ionone (58.87g, 0.3mol) was pumped into the autoclave with an advection pump, and the stirring device of the autoclave was turned on. By GC detection, the conversion rate of β-ionone was 99.92%, and the selectivity of dihydroβ-ionone was 97.26%.

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Abstract

The present invention provides a method for preparing γ‑ hydrogen hydrogen hydrogen to be used as a catalyst, and Louisic acid as the auxiliary method of the method of preparing γ‑ hydrogen hydrogen hydrogen hydrogen hydrogen hydrogen hydrogen.The one -step method enables α, γ unsaturated dieyl, to reduce silicon hydrogen, to obtain γ‑ hydride.The reaction conditions of the present invention are mild, the operation is simple, and the target product is selective and the income is high; the silicon hydrogen is cheap and easy to obtain, the catalyst activity is high, the amount is small, the cost is low, and the potential for industrialization amplification.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing γ-ketene from α,γ-unsaturated dienone. Background technique [0002] The selective reduction of α,β-carbon-carbon double bonds of conjugated α,γ-dienones is an important class of reactions that can yield a series of high value-added fine chemical products, such as selective reduction of 6-methyl-3 , α, β-carbon-carbon double bond of 5-heptadien-2-one, 6-methyl-5-hepten-2-one can be obtained, which is linalool, citral, citronellal, It is an important synthetic intermediate for spices such as ionone; and β-ionone selectively reduces α, β-carbon-carbon double bonds to obtain dihydroβ-ionone, which is the key intermediate for the synthesis of ambergris. Since α,γ-dienone contains three unsaturated double bonds, there are theoretically many different hydrogenation products, and it is extremely challenging to control the selectivity of this type of r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/21C07C45/62
CPCC07C45/62C07C49/21
Inventor 沈稳黄文学于斌成谢硕张永振黎源
Owner WANHUA CHEM GRP CO LTD