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Method for preparing lactones by biomimetic catalytic oxidation of ketone compounds

A technology for the biomimetic catalytic oxidation of ketones and ketones, applied in chemical instruments and methods, chemical/physical processes, physical/chemical process catalysts, etc., can solve the problems of complex catalyst preparation, environmental pollution, etc., and achieve easy separation and no pollution Cost, effectiveness of process cleaning

Inactive Publication Date: 2008-06-25
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although this reaction system has a good catalytic effect, the preparation of the catalyst is relatively complicated, and in the preparation process, nitric acid (Kawabata T, et al.J.Mol.Catal.A2006, 253, 279 ) which is highly corrosive to the equipment is used. -289), there is a problem of polluting the environment

Method used

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  • Method for preparing lactones by biomimetic catalytic oxidation of ketone compounds
  • Method for preparing lactones by biomimetic catalytic oxidation of ketone compounds
  • Method for preparing lactones by biomimetic catalytic oxidation of ketone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Contains 2 x 10 in 5 mL -5 Four-(o-nitrophenyl) manganese porphyrin of mol / L (being R in the general formula (I) 1 = NO 2 , R 2 = H, M 1 =Mn) in the toluene solution, add 0.02mol / L cyclohexanone and 0.05mmol benzaldehyde, feed the oxygen of 0.1MPa, stir reactant 6 hours at 40 ℃, the transformation rate of cyclohexanone is 96%, The yield of cyclocaprolactone was 96%.

[0021]

Embodiment 2

[0023] Contains 2 x 10 in 5 mL -4 The tetra-(ortho-chlorophenyl) iron porphyrin of mol / L (being R in the general formula (I) 1 = Cl, R 2 = H, M 1 =Fe) in the toluene solution, add 0.1mol / L 4-methylcyclohexanone and 0.5mmol benzaldehyde, feed 0.5MPa oxygen, stir the reactant at 60°C for 6 hours, 4-methylcyclohexanone The conversion of ketone was 90%, and the yield of 4-methylcyclocaprolactone was 90%.

[0024]

Embodiment 3

[0026] Contains 2 x 10 in 5 mL -3 The four-(o-methoxyphenyl) cobalt porphyrin of mol / L (being R in the general formula (I) 1 =OCH 3 , R 2 = H, M 1 =Co) in the toluene solution, add 2-methylcyclohexanone and 5mmol benzaldehyde of 0.5mol / L, pass into the oxygen of 0.8MPa, stir reactant 2 hours at 80 ℃, 2-methylcyclohexanone The conversion rate of is 85%, and the yield of 2-methylcyclocaprolactone is 85%.

[0027]

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Abstract

The invention discloses a method for putting the oxydone compounds into the biomimetic catalysis to prepare the lactone. With the ketone compounds as the raw materials, the invention selects the mononuclear metalloporphyrins with structure in the general formulas (I) and (II) or Mu-oxygen-binuclear metalloporphyrins with structure in the general formula (III) as the catalysts; the concentration of the catalysts ranges from 2 multiplied by 10<-5>mol / L to 2 multiplied by 10<-2>mol / L and the concentration of the ketone compounds ranges from 0.02mol / L to 0.8mol / L; with the benzene, the toluene, the xylene, the benzotrifluoride or the cyclohexane as the solvents, the benzaldehyde, isobutyraldehyde or butyraldehyde with a molar ratio to the ketone compounds ranging from 0.5 to 1 to 20 to 1 is added in the mixtures; the oxygen with a pressure ranging from 0.1MPa to 1.6MPa is pumped in the mixtures; the reaction temperature is controlled to a range from 40 DEG C to 150 DEG C and the reaction time is controlled to a range from 1 to 10 hours. The invention has the advantages of gentile reaction conditions, a small dosage of catalysts, good catalytic effects, and high product selectivity, etc.

Description

technical field [0001] The invention relates to a method for preparing a lactone compound, in particular to a method for preparing a lactone by biomimetic catalytic oxidation of ketone compounds with oxygen as an oxidant. Background technique [0002] Lactone is an important intermediate in organic synthesis. In 1899, Baeyer and Villiger first reported the conversion of menthone into corresponding lactone using persulfuric acid as an oxidant. Since then, the Baeyer-Villiger reaction has been widely used in organic synthesis. At present, in the method for preparing lactone by Baeyer-Villiger oxidation reaction, the oxidants used are usually organic peracids such as m-CPBA (m-chloroperbenzoic acid), trifluoroperacetic acid, peroxyacetic acid and the like. The use of these oxidants is not only expensive, but also produces a large amount of harmful substances, causing pollution to the environment. [0003] Therefore, the use of clean and safe oxygen as an oxidizing agent has at...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D315/00C07D309/30C07D313/04C07D493/08B01J23/14B01J23/02
Inventor 纪红兵袁秋兰周贤太
Owner SOUTH CHINA UNIV OF TECH
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