Method for preparing epoxy compound by oxidating olefin or cycloolefine through bionic catalysis oxygen

A technology for oxidation of epoxy compounds and oxygen, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc. Low-level problems, to achieve the effect of small corrosion, simple reaction operation, and mild reaction conditions

Inactive Publication Date: 2007-02-21
SOUTH CHINA UNIV OF TECH
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Problems solved by technology

[0003] Chinese patent CN1544404A discloses a method of using a metalloporphyrin compound or a mixture of a metalloporphyrin and a transition metal salt as a catalyst, and using a chemical oxidant or pure oxygen or air as an oxidant to catalyze the oxidation of olefins to prepare enols, enones, and epoxides

Method used

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  • Method for preparing epoxy compound by oxidating olefin or cycloolefine through bionic catalysis oxygen
  • Method for preparing epoxy compound by oxidating olefin or cycloolefine through bionic catalysis oxygen
  • Method for preparing epoxy compound by oxidating olefin or cycloolefine through bionic catalysis oxygen

Examples

Experimental program
Comparison scheme
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Example Embodiment

[0021] Example 1

[0022] In 50mL containing 100ppm tetra-(o-nitrophenyl) manganese porphyrin (i.e. R in general formula (I) 1 =NO 2 , R 2 = H, M 1 = Mn) in the toluene solution, add 20mL cyclohexene and 1.8mL isobutyraldehyde, feed oxygen at a pressure of 1.5MPa, and stir the reactants at 40°C for 5 hours. The cyclohexene conversion rate is 84%. The yield of epoxide was 82%.

Example Embodiment

[0023] Example 2

[0024] In 50mL containing 50ppm tetra-(o-nitrophenyl) manganese porphyrin (i.e. R in general formula (I) 1 =NO 2 , R 2 = H, M 1 =Mn) in the toluene solution, add 20mL cyclohexene and 9.0mL isobutyraldehyde, pass oxygen at a pressure of 2.0MPa, and stir the reactants at 160°C for 8 hours. The cyclohexene conversion rate is 93%. The yield of epoxide was 91%.

Example Embodiment

[0025] Example 3

[0026] In 50mL containing 10ppm tetra-(o-methoxyphenyl) cobalt porphyrin (i.e. R in general formula (I) 1 =OCH 3 , R 2 = H, M 1 =Co) in the toluene solution, add 26mL cyclooctene and 18mL isobutyraldehyde, add oxygen at a pressure of 1.5MPa, and stir the reactants at 80°C for 6 hours. The cyclooctene conversion rate is 92%. The oxide yield was 87%.

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Abstract

This invention relates to a method for preparing epoxide from olefin or cycloolefin by biomimetic catalytic oxygen oxidation. The method uses mononuclear metalloporphyrin or mu-O-binuclear metalloporphyrin as the catalyst, which has similar structure to bioenzyme. The concentration of the catalyst is 0.1-100 ppm. Besides, methane dichloride, benzene, toluene, methanol or ethyl acetate is used as the solvent. And isobutylaldehyde or n-butyraldehyde is also added at a mol ratio of 1 : (0.1-2) to the reactant. The reaction is performed at 40-160 deg.C in 0.1-2.0 MPa oxygen atmosphere for 5-12 h. The method has such advantages as low catalyst amount, low reaction temperature and pressure and easy operation. The catalyst has good catalytic performance on olefin or cycloolefin oxidation to obtain epoxide.

Description

technical field [0001] The invention relates to a method for preparing olefin epoxy compounds, in particular to a method for preparing epoxy compounds by biomimetic catalytic oxygen oxidation of olefin or cycloolefin. Background technique [0002] At present, the epoxidation of olefins, such as the epoxidation of ethylene, can be realized in the next step under gas-phase reaction conditions under the condition of noble metals such as gold or silver as catalysts. This method has certain advantages, but the olefins that can be epoxidized by this method are very limited, and the reaction conditions are very harsh, and the catalyst is expensive. Metalloporphyrin compounds are effective mimics of cytochrome P-450 monooxygenases, which have a good activation ability for oxygen. [0003] Chinese patent CN1544404A discloses a method of using a metalloporphyrin compound or a mixture of a metalloporphyrin and a transition metal salt as a catalyst, and using a chemical oxidant or pure...

Claims

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Application Information

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IPC IPC(8): C07D301/06B01J31/12B01J31/22
Inventor 纪红兵周贤太徐建昌裴丽霞王乐夫
Owner SOUTH CHINA UNIV OF TECH
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