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Method of preparing alpha-phenethyl alcohol compounds by catalytic oxidation of side chains of aromatic hydrocarbon by using metalloporphyrin

A technology for the oxidation of aromatic hydrocarbons and metalloporphyrins catalyzed by porphyrin, which is applied in the direction of oxidation reaction preparation, organic compound preparation, chemical instruments and methods, etc., can solve the problems of increased preparation cost, large salty wastewater, and high energy consumption in the reaction process. Achieve the effect of avoiding environmental pollution problems and high energy consumption required for recycling, broad application prospects, and reducing energy consumption

Inactive Publication Date: 2014-04-30
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] (1) The amount of catalyst used is large (above 4000ppm), and a large amount of saline wastewater is produced, causing serious environmental pollution and equipment corrosion;
[0009] (2) The reaction time is too long (more than 12h), the reaction efficiency is low, and the energy consumption of the reaction process is high;
[0010] (3) The reaction must use a solvent and N-hydroxyphthalimide as a free radical initiator, which not only corrodes the equipment, increases the production cost, but also causes serious environmental pollution and high energy consumption

Method used

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  • Method of preparing alpha-phenethyl alcohol compounds by catalytic oxidation of side chains of aromatic hydrocarbon by using metalloporphyrin
  • Method of preparing alpha-phenethyl alcohol compounds by catalytic oxidation of side chains of aromatic hydrocarbon by using metalloporphyrin
  • Method of preparing alpha-phenethyl alcohol compounds by catalytic oxidation of side chains of aromatic hydrocarbon by using metalloporphyrin

Examples

Experimental program
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Effect test

Embodiment 1

[0027] In a 100mL three-necked flask, add 15.4g o-bromoethylbenzene successively, 1.0×10 -3 g tetraphenyl cobalt porphyrin chloride (i.e. R in the general formula (IV) 21 for H, R 22 for H, R 23 for H, M 2 is Co, X is Cl), and 1 atm of oxygen was introduced at a flow rate of 40 mL / min, and the reaction was carried out at 130°C for 12 hours. The reacted mixture was distilled under reduced pressure and recrystallized from ethanol to obtain the filtrate to obtain α-o-bromophenethyl alcohol. After analysis by liquid chromatography, the yield was 8.2%.

Embodiment 2

[0029] In a 100mL three-necked flask, add 15.4g o-bromoethylbenzene successively, 1.0×10 -3 g four-(p-hydroxyphenyl)copper porphyrin (that is, R in the general formula (III) 11 for H, R 12 for H, R 13 for OH, M 1 For Cu), 1atm oxygen was introduced at a flow rate of 40mL / min, and the reaction was carried out at 140°C for 12h. The reacted mixture was distilled under reduced pressure and recrystallized from ethanol to obtain the filtrate to obtain α-o-bromophenethyl alcohol. After analysis by liquid chromatography, the yield was 6.3%.

Embodiment 3

[0031] In a 100mL three-necked flask, add 15.4g o-bromoethylbenzene successively, 1.0×10 -3 g four-(o-methylphenyl) zinc porphyrin (i.e. R in the general formula (III) 11 for CH 3 , R 12 for H, R 13 for H, M 1 Zn), 1atm oxygen was introduced at a flow rate of 40mL / min, and the reaction was carried out at 120°C for 12h. The reacted mixture was distilled under reduced pressure and recrystallized from ethanol to obtain the filtrate to obtain α-o-bromophenethyl alcohol. After analysis by liquid chromatography, the yield was 1.36%.

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Abstract

The invention relates to a method of preparing alpha-phenethyl alcohol compounds by catalytic oxidation of side chains of aromatic hydrocarbon by using metalloporphyrin. According to the method, aromatic hydrocarbon serving as a raw material and oxygen serving as an oxidant react for 1-12 hours at 90-160 DEG C in the presence of 5-60ppm metalloporphyrin serving as a catalyst under the conditions of normal pressure and no solvent to obtain the alpha-phenethyl alcohol compounds. According to the method, the environment-friendly metalloporphyrin compound which is extremely less in dosage as the catalyst, the problems that brine waste is hard to treat and equipment is corroded due to use of an acetate catalyst in a large amount in other methods are solved, the energy consumption in the reaction process is reduced as the reaction time is shortened. In addition, according to the method, no radical initiators or solvents are used, the cost of raw materials in product preparation can be greatly lowered, and the problems that the environment is severely polluted and the energy consumption is high due to solvent recovery and product separation are solved. Therefore, the method has a wide application prospect industrially.

Description

technical field [0001] The invention relates to a preparation method of α-phenylethyl alcohol compounds, in particular to a method for preparing α-phenylethyl alcohol compounds by catalyzing the oxidation of aromatic hydrocarbon side chains by metalloporphyrins. Background technique [0002] α-Phenyl alcohol compounds are important intermediates in organic synthesis, widely used in the synthesis of medicines, spices, coatings, textile industry, photosensitive materials, etc. At present, the preparation methods of α-phenethyl alcohol compounds mainly include the reduction method of acetophenone derivatives and the oxidation method of ethylbenzene derivatives. The one-step preparation method of α-phenylethanol compounds by oxygen oxidation of aromatic side chains has the advantages of easy availability of raw materials, high atom economy, short process, simple operation, and simple separation. Compared with other synthetic methods, it has broader industrial application prospec...

Claims

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Application Information

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IPC IPC(8): C07C33/22C07C33/46C07C29/50C07C43/23C07C41/26
CPCC07C29/50C07C41/26
Inventor 佘远斌王萌王磐
Owner BEIJING UNIV OF TECH
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