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Method for catalytic oxidation of cycloalkane by confinement porphyrin Co (II)

A technology for catalytic oxidation and cycloalkane, which is applied in chemical instruments and methods, oxidation reaction preparation, organic compound preparation, etc., to achieve enhanced stability, improved conversion rate, and beneficial separation of products

Pending Publication Date: 2020-04-17
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although metalloporphyrins as catalysts have the advantages of less catalyst consumption, high catalytic efficiency, easy structure adjustment, good biocompatibility, and environmental protection, but in the process of catalytic molecular oxygen oxidation of cycloalkanes to prepare cycloalkanols and cycloalkanones, there is still no Can reduce and avoid the formation of aliphatic diacids

Method used

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  • Method for catalytic oxidation of cycloalkane by confinement porphyrin Co (II)
  • Method for catalytic oxidation of cycloalkane by confinement porphyrin Co (II)
  • Method for catalytic oxidation of cycloalkane by confinement porphyrin Co (II)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] In a 100mL stainless steel autoclave with polytetrafluoroethylene liner, 0.00026g (0.0002mmol) 5,10,15,20-tetraphenyl-2,3,7,8,12,13,17,18 - Octabromoporphyrin cobalt (II) was dispersed in 16.8320 g (200 mmol) of cyclohexane, the reaction vessel was sealed, the temperature was raised to 120° C. with stirring, and oxygen was introduced to 1.0 MPa. At 120°C, 1.0MPa oxygen pressure, 800rpm stirring reaction for 8.0h. After completion of the reaction, cool to room temperature with ice water, add 1.3115g (5.00mmol) triphenylphosphine (PPh 3 ), stirred at room temperature for 30min to reduce the generated peroxide. Using acetone as solvent, the resulting reaction mixture was adjusted to 100 mL. Pipette 10 mL of the resulting solution, and use toluene as an internal standard for gas chromatography analysis; pipette 10 mL of the resulting solution, and use benzoic acid as an internal standard for liquid chromatography analysis. Cyclohexane conversion 5.53%, cyclohexanol selec...

Embodiment 2

[0038] In a 100mL stainless steel autoclave with polytetrafluoroethylene liner, 0.0026g (0.002mmol) 5,10,15,20-tetraphenyl-2,3,7,8,12,13,17,18 - Octabromoporphyrin cobalt (II) was dispersed in 16.8320 g (200 mmol) of cyclohexane, the reaction vessel was sealed, the temperature was raised to 120° C. with stirring, and oxygen was introduced to 1.0 MPa. At 120°C, 1.0MPa oxygen pressure, 800rpm stirring reaction for 8.0h. After completion of the reaction, cool to room temperature with ice water, add 1.3115g (5.00mmol) triphenylphosphine (PPh 3 ), stirred at room temperature for 30min to reduce the generated peroxide. Using acetone as solvent, the resulting reaction mixture was adjusted to 100 mL. Pipette 10 mL of the resulting solution, and use toluene as an internal standard for gas chromatography analysis; pipette 10 mL of the resulting solution, and use benzoic acid as an internal standard for liquid chromatography analysis. Cyclohexane conversion 5.72%, cyclohexanol selecti...

Embodiment 3

[0040] In a 100mL stainless steel autoclave with polytetrafluoroethylene liner, 0.0261g (0.0200mmol) 5,10,15,20-tetraphenyl-2,3,7,8,12,13,17,18 - Octabromoporphyrin cobalt (II) was dispersed in 16.8320 g (200 mmol) of cyclohexane, the reaction vessel was sealed, the temperature was raised to 120° C. with stirring, and oxygen was introduced to 1.0 MPa. At 120°C, 1.0MPa oxygen pressure, 800rpm stirring reaction for 8.0h. After completion of the reaction, cool to room temperature with ice water, add 1.3115g (5.00mmol) triphenylphosphine (PPh 3 ), stirred at room temperature for 30min to reduce the generated peroxide. Using acetone as solvent, the resulting reaction mixture was adjusted to 100 mL. Pipette 10 mL of the resulting solution, and use toluene as an internal standard for gas chromatography analysis; pipette 10 mL of the resulting solution, and use benzoic acid as an internal standard for liquid chromatography analysis. Cyclohexane conversion 5.76%, cyclohexanol select...

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Abstract

The invention relates to a method for catalytic oxidation of cycloalkane by confinement porphyrin Co (II). The method comprises the following steps: dispersing confinement cobalt porphyrin (II) in cycloalkane, sealing the reaction system, heating to 100-130 DEG C while stirring, introducing oxygen to 0.2-3.0 MPa, keeping the set temperature and oxygen pressure, stirring to react for 3.0-24.0 h, and carrying out post-treatment on a reaction solution to obtain products naphthenic alcohol and naphthenic ketone. The method achieves high selectivity of naphthenic alcohol and naphthenic ketone, andeffectively inhibits the generation of aliphatic diacid. The aliphatic diacid is low in selectivity, so that the continuity of the cycloalkane oxidation process and the separation of the products arefacilitated; the method has the potential of solving the problem that naphthenic alcohol and naphthenic ketone are easily and deeply oxidized to generate aliphatic diacid in the industrial cycloalkanecatalytic oxidation process; and the method is a novel efficient and feasible method for selective catalytic oxidation of cycloalkane.

Description

[0001] (1) Technical field [0002] The invention relates to a new method for preparing cycloalkanol and cycloalkanone by catalyzing molecular oxygen selective oxidation of cycloalkane by confined porphyrin Co(II), belonging to the field of organic catalysis and fine organic synthesis. [0003] (2) Background technology [0004] Catalytic oxidation of naphthenes is an important chemical transformation process. The oxidation products cycloalkanol and cycloalkanone are not only important organic solvents, but also important fine chemical intermediates, which are widely used in the production of fine chemical products such as pesticides, medicines, and dyes. 合成(WO 2019046316;WO 2019030294;WO 2019069911;CN 108864082;CN 109180556;Journal of Medicinal Chemistry 2019,62:1837-1858;Russian Journal of GeneralChemistry 2018,88:2646-2652,即世界专利2019046316;世界专利2019030294; World Patent 2019069911; Chinese Patent 108864082; Chinese Patent 109180556; Journal of Medicinal Chemistry 2019, 62: 1837-...

Claims

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Application Information

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IPC IPC(8): C07C29/50C07C35/08C07C35/06C07C35/20C07C35/205C07C45/33C07C49/403C07C49/395C07C49/413
CPCC07C29/50C07C45/33C07C2601/08C07C2601/14C07C2601/18C07C2601/20C07C35/08C07C35/06C07C35/20C07C35/205C07C49/403C07C49/395C07C49/413
Inventor 佘远斌王琴宁磊沈海民
Owner ZHEJIANG UNIV OF TECH
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