Preparation method and application of camphor manganese porphyrin

A technology of camphor manganese porphyrin and camphorone acid chloride, which is applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, organic chemistry, etc., can solve the problems of low yield and long reaction time, and achieve The effect of high catalytic efficiency

Inactive Publication Date: 2011-10-05
SHAANXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among the above methods, some have long reaction times, low yields, and some catalysts are more expensive.

Method used

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  • Preparation method and application of camphor manganese porphyrin
  • Preparation method and application of camphor manganese porphyrin
  • Preparation method and application of camphor manganese porphyrin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Take preparation 5,10,15,20-tetrakis (4-camphor ketone amido phenyl) manganese porphyrin as example, used raw material and preparation method thereof are as follows:

[0024] 1. Mix 3.6g (20mmol) camphoronic acid with 2.2mL (30mmol) SOCl 2 Mix, stir at room temperature for 2 hours, reflux at 80°C for 1 hour, distill off SOCl 2 , prepared into camphorone acid chloride, the yield was 95%.

[0025] 2. Mix 11.0g (72mmol) of 4-nitrobenzaldehyde and 5mL (72mmol) of pyrrole and react at 150°C for 0.5 hours to prepare 5,10,15,20-tetrakis(4-nitrophenyl)porphyrin, Its yield was 23.4%.

[0026] 3. Add 0.79g (1mmol) 5,10,15,20-tetrakis(4-nitrophenyl)porphyrin and 3.04g (16mmol) stannous chloride to 40mL of 36.5% hydrochloric acid, mix well , reacted at 80° C. for 0.5 hour to prepare 5,10,15,20-tetrakis(4-aminophenyl)porphyrin with a yield of 90%.

[0027] 4. In N 2 Protection, under the condition of -20~-17°C, add 0.63g (1mmol) 5,10,15,20-tetrakis(4-aminophenyl)porphyrin, 1.6g...

Embodiment 2

[0030] Taking the preparation of 2,3,12,13-tetrabromo-5,10,15,20-tetrakis(4-camphoronamidophenyl)manganese porphyrin as an example, the raw materials used and the preparation method thereof are as follows:

[0031] l, 3.6g (20mmol) camphoronic acid and 2.2mL (30mmol) SOCl 2 Mix, stir at room temperature for 2 hours, reflux at 80°C for 1 hour, distill off SOCl 2 , prepared into camphorone acid chloride, the yield was 95%.

[0032] 2. Mix 11.0g (72mmol) of 4-nitrobenzaldehyde and 5mL (72mmol) of pyrrole and react at 150°C for 0.5 hours to prepare 5,10,15,20-tetrakis(4-nitrophenyl)porphyrin, Its yield was 23.4%.

[0033] 3. Add 0.79g (1mmol) 5,10,15,20-tetrakis(4-nitrophenyl)porphyrin and 3.04g (16mmol) stannous chloride to 40mL of 36.5% hydrochloric acid, mix well , reacted at 80° C. for 0.5 hour to prepare 5,10,15,20-tetrakis(2-methyl-4-aminophenyl)porphyrin with a yield of 90%.

[0034] 4. In N 2 Protection, under the condition of -20~-17°C, add 0.63g (1mmol) 5,10,15,20-t...

Embodiment 3

[0038] In step 2 of Example 1, the raw material 4-nitrobenzaldehyde used is replaced by equimolar 3-methoxy-4-nitrobenzaldehyde, and equimolar 3-ethoxy-4-nitrobenzaldehyde can also be used Benzaldehyde or 3-propoxy-4-nitrobenzaldehyde or 3-butoxy-4-nitrobenzaldehyde or 3-methyl-4-nitrobenzaldehyde or 3-ethyl-4-nitro Benzaldehyde or 3-propyl-4-nitrobenzaldehyde or 3-butyl-4-nitrobenzaldehyde are replaced, and other steps of this step are identical with embodiment 1. The other steps are the same as in Example 1, and 5,10,15,20-tetrakis(3-methoxy-4-camphoronamidophenyl)manganese porphyrin or 5,10,15,20-tetrakis(3 -Ethoxy-4-camphoronamidophenyl) manganese porphyrin or 5,10,15,20-tetrakis(3-propoxy-4-camphoronamidophenyl)manganese porphyrin or 5,10 , 15,20-tetrakis(3-butoxy-4-camphoronamidophenyl) manganese porphyrin or 5,10,15,20-tetrakis(3-methyl-4-camphoronamidophenyl) Manganese porphyrin or 5,10,15,20-tetrakis(3-ethyl-4-camphoronamidophenyl)manganese porphyrin or 5,10,15,20-t...

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Abstract

A preparation method of camphor manganese porphyrin comprises the following steps: reducing 5,10,15,20-tetra(4-nitro substituted phenyl) porphyrin to 5,10,15,20-tetra(4-amido substituted phenyl) porphyrin with stannous chloride in a system of concentrated hydrochloric acid; acylating with camphorone acyl chloride to synthesize 5,10,15,20-tetra(4-camphorone amido substituted phenyl) porphyrin; andintroducing manganese metal with an epoxidation catalysis performance into a center of 5,10,15,20-tetra(4-camphorone amido substituted phenyl) porphyrin to coordinate with porphyrin to form manganese(III) porphyrin. Camphor manganese porphyrin prepared in the present invention can be applied to the epoxidation reaction of alpha, beta-unsaturated ketone, and can be used to catalyze the epoxidation of alpha, beta-unsaturated ketone by hydrogen peroxide in an alkaline condition, so alpha, beta-unsaturated ketone can be almost completely converted into epoxidation products of alpha, beta-unsaturated ketone in a short time, and the catalysis efficiency is high.

Description

technical field [0001] The invention belongs to the technical field of synthesis of oxirane rings, and in particular relates to a preparation method of a camphor manganese porphyrin catalyst and its application in catalyzing α, β-unsaturated ketone epoxidation reactions. Background technique [0002] Epoxidation of α, β-unsaturated ketones is an important class of organic intermediate compounds. Due to the introduction of carbonyl groups, its epoxides can be synthesized into a wide variety of structural building blocks through selective ring opening and functional group conversion. Therefore, it has attracted extensive attention of researchers. The epoxidation reaction of alkenes is an electrophilic reaction, but due to the electron deficiency of the α, β-unsaturated ketone double bond, the epoxidation is not easy to occur. At present, more researches are mainly on some basic catalysts, such as: KF / Al 2 o 3 、KOH / Al 2 o 3 , NaOH, KOH, LiOH, Na 2 CO 3 , Hydrotalcite, et...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22B01J31/22C07D301/12C07D303/32
Inventor 徐峰潘宁蒋婷田又平
Owner SHAANXI NORMAL UNIV
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