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Method for preparing macrocycloalkanone from epoxide

A technology for epoxide and macrocycloalkanone, applied in the field of chemical synthesis technology, can solve the problems of undisclosed catalyst recovery, high price of lithium bromide, lower production cost, etc., achieves low price, obvious energy consumption advantage, reduced difficulty and operation effect of difficulty

Active Publication Date: 2021-10-01
CHINA TIANCHEN ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The amount of catalyst used in this process is relatively high, which is 5 mol% of the raw material, and the price of lithium bromide, especially lithium iodide, is relatively high, and the patent does not disclose whether the catalyst can be recovered, so it is unfavorable for industrialization to reduce production costs

Method used

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  • Method for preparing macrocycloalkanone from epoxide
  • Method for preparing macrocycloalkanone from epoxide
  • Method for preparing macrocycloalkanone from epoxide

Examples

Experimental program
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Effect test

Embodiment 1

[0052] Isomerization of 1,2-epoxycyclododecane to cyclododecanone in the presence of a catalyst prepared from ligand L1 (2,6-diphenylphenol).

[0053] Add 10.5 mmol of ligand L1 (2,6-diphenylphenol) and 100 mL of anhydrous toluene into a heat-dried reaction flask. At room temperature, 6.6 mmol of trimethylaluminum-toluene solution (0.2 mol / L) was added to the transparent solution. The solution was stirred at 25°C. After a few minutes, a catalyst solution was obtained. The catalyst solution was heated to 40°C, and 120 g (659 mmol) of 1,2-epoxycyclododecane was added within 2 h, and the temperature was maintained to continue stirring for 2 h. After the reaction solution was detected by gas chromatography and quantified by calibration and normalization method, the conversion rate of 1,2-epoxycyclododecane was 100%, and the selectivity of cyclododecanone was 98.3%. After the reaction was completed, the reaction solution was rectified and purified to finally obtain cyclododecano...

Embodiment 2

[0055] Isomerization of 1,2-epoxycyclooctane to cyclooctanone in the presence of a catalyst prepared from ligand L2 (2,6-di-tert-butylphenol).

[0056] Add 20 mmol of ligand L2 (2,6-di-tert-butylphenol) and 100 mL of anhydrous toluene into a heat-dried reaction flask. At 0°C, 6.6 mmol of triethylaluminum-toluene solution (0.2 mol / L) was added to the transparent solution. The solution was stirred at 0 °C. After a few minutes, a catalyst solution was obtained. The catalyst solution was heated to 20° C., and 167 g (1.32 mol) of 1,2-epoxycyclooctane was added within 1 h, and the temperature was maintained to continue stirring for 3 h. After the reaction solution was detected by gas chromatography and quantified by calibration and normalization method, the conversion rate of 1,2-epoxycyclooctane was 99.8%, and the selectivity of cyclooctanone was 99.2%. After the reaction was finished, the reaction liquid was subjected to rectification and purification, and finally the yield of ...

Embodiment 3

[0058] Isomerization of 1,2-epoxycyclodecane to cyclodecanone in the presence of a catalyst prepared from ligand L3 (2,6-diα-naphthylphenol).

[0059] Add 20mmol of ligand L3 (2,6-diα-naphthylphenol) and 100mL of anhydrous toluene into the heat-dried reaction flask. At 50°C, 10 mmol of tripropylaluminum-toluene solution (0.1 mol / L) was added to the transparent solution. The solution was stirred at 50°C. After a few minutes, a catalyst solution was obtained. The catalyst solution and the raw material 1,2-epoxycyclodecane were respectively pumped into a 3-stage series reactor, the jacket of the reactor was circulating water, the temperature inside the kettle was controlled at 60°C, and the reaction pressure was normal pressure. By controlling the flow rate of the pump, the molar ratio of the catalyst to the raw material 1,2-epoxycyclodecane is 0.001:1, and at the same time, the residence time of the reaction solution in each reactor is 15 minutes. The reaction continued to ru...

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Abstract

The invention provides a method for preparing a macrocycloalkanone from an epoxide. The method comprises the following steps of: mixing a ligand L, an aluminum compound and a solvent to obtain a catalyst solution; injecting the catalyst solution and an epoxide into a reactor for reaction to obtain a reaction solution; and separating and purifying the reaction liquid to obtain the required product. Compared with the prior art, the method provided by the invention has the advantages that the reaction conditions are milder, the macrocycloalkanone can be prepared at the temperature of 50-100 DEG C, the problems of side reactions such as oxidation, isomerization and decomposition of raw materials and products and carbon deposition and coking of a catalyst caused by high-temperature reaction at 200 DEG C or above in the prior art are solved, high-selectivity and high-yield continuous preparation of the macrocycloalkanone compound is realized, generation of high-boiling-point byproducts with functional groups and similar carbon atom numbers is avoided, and the product separation difficulty and the operation difficulty are greatly reduced.

Description

technical field [0001] The invention belongs to the field of chemical synthesis technology, in particular to a method for preparing macrocycloalkanones from epoxides. Background technique [0002] Macrocycloalkanones are key intermediates for the preparation of long carbon chain special nylon and macrocyclic muskone. Specific products include dodecanedioic acid, dodecanediamine, nylon 12, nylon 612, nylon 1012, nylon 1212, and nylon 12T , 3-methylcyclopentacene, racemic muskone, cyclopentadecanone, 5-cyclohexadecenone, cyclopentadecanone, 12-methyl-14-carbonylbicyclo[9,3,1 ] Pentadecane etc. [0003] The synthetic technique of macrocycloalkanone comprises following several kinds: [0004] 1. Macrocycloalkane Air Oxidation Process [0005] Preparation of macrocycloalkanone / alcohol mixtures by air oxidation of macrocycloalkanes, separation, dehydrogenation to macrocycloalkanones, this process can be obtained by the known Bashkirow oxidation method (CDAN; Oenbrink, G. and Sc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/58C07C49/413C07C49/385C07C49/433B01J31/22
CPCC07C45/58B01J31/2208C07C2601/20C07C2601/18C07C2602/42B01J2531/31C07C49/413C07C49/385C07C49/433
Inventor 吴昊冯传密史文涛杨光王聪杨克俭刘新伟王元平霍瑜姝
Owner CHINA TIANCHEN ENG
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