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A kind of preparation method of ethoxyquinoline

A technology of ethoxyquinoline and ethoxyquinoline, which is applied in the field of preparation of ethoxyquinoline, can solve the problems of being unable to supply the high-end feed market, low production efficiency, and low product content, so as to achieve good industrial prospects and control costs , the effect of high purity

Active Publication Date: 2019-07-02
宜兴市天石饲料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction kettle is used in the preparation of this method. Although the final cyclization rate reaches more than 90%, the reaction temperature in the existing preparation method is as high as 120°C, and the reaction time is more than 20 hours.
In summary, this method has long reaction time, low conversion rate, and requires far more than theoretical amounts of acetone and toluene as reaction raw materials and solvents. The production efficiency is low, and the obtained product content is not high, which cannot be supplied to the high-end feed market.

Method used

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  • A kind of preparation method of ethoxyquinoline
  • A kind of preparation method of ethoxyquinoline
  • A kind of preparation method of ethoxyquinoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 4-ethoxy-N-(propane-2-enyl)aniline (177g, 1.0mol) and toluene (880g) into the reactor, after stirring evenly, add the newly prepared ((2- Methyl-1,3-dioxolan-2-yl)methyl)magnesium chloride in THF, where ((2-methyl-1,3-dioxolan-2-yl)methyl)magnesium chloride is Compound (II) (176.5g, 1.1mol) and tetrahydrofuran (880g) were kept at 55-60°C for 12 hours after the dropwise addition, and the reaction was completed.

[0029] Then most of the tetrahydrofuran was removed by distillation under normal pressure, then dilute hydrochloric acid (885g) with a concentration of 5% was added, and stirring at room temperature was continued for 5 hours. Aqueous sodium oxide solution was used to adjust the pH to 10, and toluene (1770g) was added to the neutralized mixture, separated after extraction, and the organic phase was loaded into a new reactor, then p-toluenesulfonic acid (8.85g) was added, and the temperature was raised to Stir and divide water under reflux for 6 hours, then d...

Embodiment 2

[0032] Add 4-ethoxy-N-(propane-2-enyl)aniline (II) (177g, 1.0mol) and toluene (550g) into the reactor, after stirring evenly, add the newly prepared ( (2-Methyl-1,3-dioxolan-2-yl)methyl)magnesium chloride in tetrahydrofuran, where ((2-methyl-1,3-dioxolan-2-yl)methyl ) Magnesium chloride is compound (II) (160.5g, 1.0mol), tetrahydrofuran is (550g), after the dropwise addition is completed, keep warm at 55-60°C and continue to react for 4 hours, and the reaction ends.

[0033] Then most of the tetrahydrofuran was removed by distillation under normal pressure, then dilute hydrochloric acid (885g) with a concentration of 5% was added, and stirring at room temperature was continued for 5 hours. Aqueous sodium oxide solution was used to adjust the pH to 10, and toluene (1770g) was added to the neutralized mixture, separated after extraction, and the organic phase was loaded into a new reactor, then p-toluenesulfonic acid (8.85g) was added, and the temperature was raised to Stir and...

Embodiment 3

[0036] Add 4-ethoxy-N-(propane-2-enyl)aniline (II) (177g, 1.0mol) and toluene (720g) into the reactor, after stirring evenly, add the newly prepared ( (2-Methyl-1,3-dioxolan-2-yl)methyl)magnesium chloride in tetrahydrofuran, where ((2-methyl-1,3-dioxolan-2-yl)methyl ) Magnesium chloride is (168.5g, 1.05mol) of compound (II), tetrahydrofuran is (720g), the temperature of the mixture is kept below 60°C during the dropwise addition, and the reaction is continued at 55-60°C for 8 hours after the dropwise addition, and the reaction ends.

[0037] Then most of the tetrahydrofuran was removed by distillation under normal pressure, then dilute hydrochloric acid (885g) with a concentration of 5% was added, and stirring at room temperature was continued for 5 hours. Aqueous sodium oxide solution was used to adjust the pH to 10, and toluene (1770g) was added to the neutralized mixture, separated after extraction, and the organic phase was loaded into a new reactor, then p-toluenesulfonic...

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Abstract

The invention discloses a preparation method of ethoxyquin. The method comprises the following concrete steps: 1, enabling 4-ethoxy-N-(propane-2-alkenyl)aniline, which is taken as a raw material, to react with ((2-methyl-1,3-dioxolane-2-yl)methyl)magnesium chloride to obtain an intermediate product; 2, hydrolyzing the obtained intermediate product for deprotection; 3, enabling the hydrolyzed product to make a cyclization reaction under an acidic condition to prepare the ethoxyquin. The ethoxyquin is prepared by a one-step method, the intermediate produced in the preparation process does not need to be separated, and a great deal of acetone and methylbenzene are not needed by the reaction, so that the conversion rate of the raw material is better improved, a reaction solvent is saved, and the pressure of environmental protection is reduced; the preparation method has the advantages of mild reaction conditions, simple technology, convenient operation and environment friendliness; furthermore, the obtained product is also higher in purity and can meet the demands of feed markets at all levels, thus having better industrial prospect.

Description

technical field [0001] The invention belongs to the field of preparation methods of chemical raw materials and pharmaceutical intermediates, and specifically relates to a preparation method of ethoxyquinoline. Background technique [0002] Ethoxyquinoline, as the most economical antioxidant, is widely used in the feed additive industry. Because it can prevent aliphatic vitamins such as vitamins A, D, E and fat oxygen from deteriorating, and prevent natural pigments in product ingredients from oxidizing and discoloring, it is especially suitable for premixes, fish meal and products with added fat. It can be used for anti-mildew, freshness preservation and anti-aging applications. In addition, in terms of the application field of feed, the comprehensive price and the achieved antioxidant effect, the use of ethoxyquinoline as an antioxidant in feed has always been the first choice, and ethoxyquinoline is the most effective for the protection of vitamins. good. According to r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/20
CPCC07D215/20
Inventor 邹益东邹苏燕朱建泉邹三元马连姣
Owner 宜兴市天石饲料有限公司
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