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Method for one-pot liquid phase synthesis of quinoline and derivative thereof

A liquid-phase synthesis and derivative technology, applied in the direction of organic chemistry, can solve the problems of difficult catalyst separation and recovery, high reaction temperature, high equipment requirements, etc., to avoid easy oxidation and deterioration and storage, less equipment investment, and reduce production cost effect

Active Publication Date: 2012-06-27
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the disadvantage is that it takes energy to vaporize the reactants, and the raw materials used are still aniline compounds and compounds such as aldehydes, ketones and esters.
Although there are also nitrobenzene and fatty alcohols or aldehydes as raw materials, these synthesis methods usually use inorganic acids or transition metal complexes as catalysts, and the separation and recovery of catalysts are difficult and require high equipment.
The gas-phase synthesis of quinoline mainly uses aromatic amines, aldehydes, ketones, and esters as raw materials, but the gas-phase method has the disadvantages of high reaction temperature and high energy consumption, and does not use nitrobenzene as a raw material, but aniline as a raw material

Method used

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  • Method for one-pot liquid phase synthesis of quinoline and derivative thereof
  • Method for one-pot liquid phase synthesis of quinoline and derivative thereof
  • Method for one-pot liquid phase synthesis of quinoline and derivative thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] (x wt%)Cu-(y wt%)Pd / Al 2 o 3 (x wt% and ywt% are the loadings of Cu and Pd respectively) The preparation process of the catalyst is as follows: use deionized water to make a certain amount of carrier into a slurry at a temperature of 70-90 ° C, and then drop a certain amount of H 2 PdCl 4 (0.05gPd / ml) and Cu(NO 3 ) 2 Aqueous solution, maintain the temperature range and fully stir and impregnate for 5 hours, then use 10% NaOH (mass percentage) aqueous solution to adjust the pH value of the solution to 8.6-10, continue to age for 30 minutes, and then cool to room temperature, filter, and wash the filter cake with deionized water to medium and dried at 110°C for 5 hours in an air atmosphere, then calcined at 260°C for 4 hours in an air atmosphere, and finally raised to 260°C at a rate of 1°C / min in a hydrogen flow of 100mL / min, and reduced at a constant temperature at 260°C 2h, and finally lowered to room temperature in a hydrogen atmosphere to obtain the catalyst.

Embodiment 2 9

[0030] Embodiments two to nine investigated the influence of reaction temperature on the reaction performance of nitrobenzene and ethanol to synthesize 2-methylquinoline. In a 500mL stainless steel autoclave, add 10mL of nitrobenzene, 60mL of absolute ethanol, 20mL of water, and Cu 5%-Pd 5% / Al prepared in Example 1 2 o 3 Catalyst 0.5g, close the reactor, replace the air in the reactor with nitrogen and keep the pressure in the reactor, after warming up to the set reaction temperature, adjust the reaction pressure to be 1.0MPa, start stirring (800r / min), constant temperature After reacting for a certain period of time, the reaction was stopped and cooled to room temperature, the reaction solution was taken out, the catalyst was removed by filtration, and the filtrate was analyzed by gas chromatography. The experimental results are shown in Table 1.

[0031] The experimental result of the influence of table 1 reaction temperature on the synthetic 2-methylquinoline of nitrobenz...

Embodiment 61

[0058] In a 10L stainless steel autoclave, add 825mL of nitrobenzene, 3300mL of absolute ethanol, 1650mL of water and Cu 5%-Pd 5% / Al prepared in Example 1 2 o 3 Catalyst 55g, close the reactor, replace the air in the reactor with nitrogen and maintain the pressure in the reactor, raise the temperature to 180°C, adjust the reaction pressure to 3.5MPa, start stirring (800r / min), keep the constant temperature reaction for 19.5h, stop React and be cooled to room temperature, take out reaction liquid, filter and remove catalyst, filtrate is analyzed by gas chromatography, 2-methylquinoline selectivity 63.5%, the selectivity of N-ethylaniline 0.7%, aniline selectivity 27.1%, other by-products The product is 8.7%, and the conversion rate of nitrobenzene is 100%.

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Abstract

The invention discloses a method for one-pot liquid phase synthesis of quinoline with formula (II) and derivative thereof. The method takes aromatic nitro-compound with formula (I) and fatty alcohol as the materials to react under the action of activator to prepare the quinoline or the derivative thereof, wherein the fatty alcohol is one of the C2-C5 fatty alcohols or the mixture of methanol and one of the C2-C5 fatty alcohols; and the activator is alumina supported palladium-copper solid activator. Through the method, the activator is easy to separate with the product and can be used repeatedly; the activator is easy to prepare and the noble metals are easy to recover, thus reducing the production cost; meanwhile, the product has good quality and high yield.

Description

(1) Technical field [0001] The invention relates to a method for one-pot liquid-phase synthesis of quinoline and its derivatives from nitrobenzene and fatty alcohol. (2) Background technology [0002] Quinoline and its derivatives are important chemical raw materials and are widely used in medicine, dyes, pesticides and chemical auxiliaries. Quinoline and its derivatives can be used to synthesize important dyes such as dye yellow 3, direct yellow 22, solvent yellow 33, quinoline-based cyanine dyes, and aminoquinoline; nicotinic acid obtained by oxidation of quinoline is an important intermediate. There are important applications in medicine and food additives. Quinoline and its derivatives are also important analytical chemical reagents, corrosion inhibitors, solvents and extractants. At present, quinoline and its derivatives are mainly synthesized from coal tar extraction or chemical methods. [0003] The coal tar extraction method not only uses a large amount of inorgan...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/06
Inventor 李小年项益智张军华丰枫汪小华马磊卢春山张群峰许孝良袁俊峰
Owner ZHEJIANG UNIV OF TECH
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