Cycloalkane catalytic oxidation method promoted by iron porphyrin

A technology for catalytic oxidation and naphthenic hydrocarbons, applied in chemical instruments and methods, hydrocarbon oxidation to prepare oxygenated compounds, catalytic reactions, etc., can solve the problems of low product selectivity, poor environmental protection, complicated operation, etc. Low dosage and good biocompatibility

Pending Publication Date: 2019-12-13
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to overcome the disadvantages of low product selectivity, complex operation and poor environmental protection in the existing cycloalkane catalytic oxidation method, the present invention provides a cycloalkane promoted by iron porphyrin with high product selectivity, simple operation and environmental protection catalytic oxidation method

Method used

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  • Cycloalkane catalytic oxidation method promoted by iron porphyrin

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] In a 100mL stainless steel autoclave with a tetrafluoroethylene liner, dissolve 1.5mg of 5,10,15,20-tetrakis(p-chlorophenyl)porphyrin cobalt(II) in 50.0g of cyclohexane, and close the autoclave kettle. Stir to raise the temperature to 120°C, pass O 2 to 1.4MPa, at 120°C, 1.4MPa O 2 The reaction was stirred under pressure for 8.0 h, stirred and cooled to room temperature in an ice-water bath. Open the autoclave, filter the obtained reaction mixture, wash the obtained solid with 3 × 5mL cyclohexane, and dry it under vacuum at 60°C, which is adipic acid. The yield of HPLC analysis is 0.32%, and the yield of cyclohexanol is 1.34% by GC analysis of the filtrate. %, cyclohexanone yield 1.43%.

Embodiment 2

[0023] In a 100mL stainless steel autoclave with a tetrafluoroethylene liner, dissolve 1.5mg of 5,10,15,20-tetrakis(p-chlorophenyl)porphyrin iron (II) in 50.0g of cyclohexane, and close the high pressure kettle. Stir to raise the temperature to 120°C, pass O 2 to 1.4MPa, at 120°C, 1.4MPa O 2 The reaction was stirred under pressure for 8.0 h, stirred and cooled to room temperature in an ice-water bath. Open the autoclave, filter the obtained reaction mixture, wash the obtained solid with 3×5mL cyclohexane, and dry it under vacuum at 60°C, which is adipic acid. The yield of HPLC analysis is 0.01%, and the yield of cyclohexanol is 0.22% by GC analysis of the filtrate. %, cyclohexanone yield 0.35%.

Embodiment 3

[0025] In a 100 mL stainless steel autoclave with a tetrafluoroethylene liner, 1.5 mg of 5,10,15,20-tetrakis(p-chlorophenyl)porphyrin cobalt(II) and 1.5 mg of 5,10,15,20- Tetrakis(p-chlorophenyl)porphyrin iron(II) was dissolved in 50.0 g of cyclohexane, and the autoclave was closed. Stir to raise the temperature to 120°C, pass O 2 to 1.4MPa, at 120°C, 1.4MPa O 2 The reaction was stirred under pressure for 8.0 h, stirred and cooled to room temperature in an ice-water bath. Open the autoclave, filter the obtained reaction mixture, wash the obtained solid with 3 × 5mL cyclohexane, and dry it under vacuum at 60°C, which is adipic acid. The yield of HPLC analysis is 0.15%, and the yield of cyclohexanol is 1.41% by GC analysis of the filtrate. %, cyclohexanone yield 1.38%.

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Abstract

The invention relates to a cycloalkane catalytic oxidation method promoted by iron porphyrin. O2 is taken as an oxidant, Co (II) porphyrin and Mn (II) porphyrin are taken as main catalysts, and Fe (II) porphyrin is taken as a cocatalyst to carry out reacting at a temperature of 100-160 DEG C and pressure of 0.8-2.0MPa under a solvent-free condition to realize catalytic oxidation of cycloalkanes. The cycloalkanes mainly comprise cyclopentane, cyclohexane, cycloheptane, cyclooctane and cyclononane, and the corresponding oxidation products mainly comprise cycloalkyl alcohols, cycloalkyl ketones and alkyl diacids. The cycloalkane catalytic oxidation method has the advantages of high selectivity of cyclopentanone, cyclohexanol, cycloheptanone and cyclooctanone, small catalyst consumption and simple operation, and environmental friendliness is achieved by taking clean O2 as the oxidant. The disclosesd cycloalkane catalytic oxidation method promoted by iron porphyrin is a cycloalkane catalytic oxidation method with high product selectivity, simple operation and environmental friendliness.

Description

technical field [0001] The invention belongs to the field of catalytic organic synthesis, and relates to a catalytic oxidation method of cycloalkane promoted by iron porphyrin. Background technique [0002] Catalytic oxidation of naphthenes is an important chemical transformation process. The oxidation products cycloalkyl alcohols and cycloalkyl ketones are not only important chemical intermediates, but also can be further oxidized to prepare alkyl diacids, which are used to prepare various An important precursor of a polymer material. At the same time, the cycloalkane oxidation process can also generate alkyldiacids, which can be directly used in the preparation of various polymer materials. For example, the main products of cyclohexane catalytic oxidation, cyclohexanol and cyclohexanone, can be further oxidized to obtain adipic acid, an important precursor for the production of nylon-66 and nylon-6, and the market demand is very large (Angew.Chem.Int.Edit., 2016 , 55:128...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22C07C27/12C07C29/50C07C45/33C07C51/31C07C55/14C07C49/403C07C35/08
CPCB01J31/183C07C51/313C07C45/33C07C29/50B01J2531/025B01J2531/842B01J2531/845B01J2531/72B01J2231/70C07C2601/14C07C55/14C07C49/403C07C35/08
Inventor 沈海民孙静
Owner ZHEJIANG UNIV OF TECH
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