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Preparation method of nipagin ester compound under promotion of sulfonic acidic ionic liquid

A technology of parabens and ionic liquids, which is applied in the preparation of organic compounds, the preparation of carboxylic acid esters, chemical instruments and methods, etc. The effect of mild production and reaction conditions

Inactive Publication Date: 2011-03-02
SHANDONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the current research on esterification in ionic liquids is mostly limited to the esterification of fatty acids, while the application of ionic liquids in the green esterification of aromatic acids is less

Method used

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  • Preparation method of nipagin ester compound under promotion of sulfonic acidic ionic liquid
  • Preparation method of nipagin ester compound under promotion of sulfonic acidic ionic liquid
  • Preparation method of nipagin ester compound under promotion of sulfonic acidic ionic liquid

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preparation example Construction

[0034] The preparation reaction of parabens:

[0035]

[0036] R=CH 3 , C 2 h 5 , n-C 3 h 7 , n-C 4 h 9 , i-C 4 h 9 , n-C 7 h 15 , n-C 12 h25 , n-C 16 h 33 , n-C 18 h 36 , etc.

[0037] Concrete preparation reaction steps are as follows:

[0038] Using sulfonic acid-type ionic liquid as reaction solvent and accelerator, under the condition of microwave radiation, make p-hydroxybenzoic acid and corresponding alcohol undergo esterification reaction at 80-120°C for 0.5-3 hours, then extract, wash and concentrate Obtain paraben product.

[0039] Wherein, the ionic liquids serving as reaction solvent and accelerator are respectively N-(4-sulfonic acid group) butyl imidazolium hydrogen sulfate (IL1), N-(3-sulfonic acid group) propyl imidazole hydrogen sulfate (IL2) , one of N-(4-sulfonic acid) butylimidazole p-toluenesulfonate (IL3) or N-(3-sulfonic acid) propylimidazole p-toluenesulfonate (IL4); p-hydroxybenzoic acid and The molar equivalent ratio of the alcoh...

Embodiment 1

[0042] Add 3.036g (0.022mol) of p-hydroxybenzoic acid and 2mL of ionic liquid N-(4-sulfonic acid) butylimidazolium bisulfate (IL1) into a 25mL round bottom bottle, stir at room temperature for 20 minutes, then add 1.8 mL (0.020 mol) of n-butanol, the microwave radiation power was set to 500w, and the reaction mixture was heated to 100°C for 0.5 hour reaction. Then the reaction system was cooled to room temperature (such as 25° C.), diluted with an appropriate amount of water, and extracted repeatedly with ether (10 mL×4 times) until there was no fluorescent substance. Vigorous stirring is necessary during extraction to ensure that no product remains in the ionic liquid. The ether phases were combined, washed with saturated sodium bicarbonate solution and saturated brine, and the organic phase was separated and dried over anhydrous sodium sulfate. Ethyl ether was removed by rotary evaporation under reduced pressure to obtain white solid n-butylparaben with a melting point of 6...

Embodiment 2

[0044] Add 3.036g (0.022mol) of p-hydroxybenzoic acid and 2mL of ionic liquid N-(4-sulfonic acid) butylimidazolium bisulfate (IL1) into a 25mL round bottom bottle, stir at room temperature for 20 minutes, then add 0.020 mol of isobutanol, the microwave radiation power was set to 600w, and the reaction mixture was heated to 110° C. for 2 hours. Then the reaction system was cooled to room temperature (such as 25° C.), diluted with an appropriate amount of water, and extracted repeatedly with ether (10 mL×4 times) until there was no fluorescent substance. Vigorous stirring is necessary during extraction to ensure that no product remains in the ionic liquid. The ether phases were combined, washed with saturated sodium bicarbonate solution and saturated brine, and the organic phase was separated and dried over anhydrous sodium sulfate. Ether was removed by rotary evaporation under reduced pressure to obtain isobutylparaben as a white solid with a melting point of 73-74°C (literatu...

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Abstract

The invention provides a preparation method of a nipagin ester compound under promotion of sulfonic acidic ionic liquid. The method comprises the following steps: taking the sulfonic acidic ionic liquid as a reaction solvent and a promoter, and carrying out esterification on p-hydroxybenzoic acid and corresponding alcohol at the temperature of 80-120 DEG C for 0.5-3h under a microwave radiation condition to obtain a coarse product of nipagin ester; adding water to the coarse product, and repeatedly extracting the product and impurities such as unreacted raw materials and the like with diethylether until a diethyl ether phase is non-fluorescent; merging the diethyl ether phase, sequentially washing with saturated sodium bicarbonate aqueous solution and saturated salt solution and drying with anhydrous sodium sulfate; removing the solvent through vacuum evaporation to obtain the nipagin ester product; and removing a large quantity of water from an aqueous phase by rotary evaporation, and drying with salicylic acid in vacuum to obtain the recovered ionic liquid which can be recycled. The preparation method has the advantages of mild reaction condition, simple batch feeding and aftertreatment, short reaction time, and high mole yield of the obtained finished product of the nipagin ester which is over 85%, and being capable of avoiding equipment corrosion and pollution caused by using strong acid.

Description

technical field [0001] The invention relates to a synthesis method of aromatic ester compounds promoted by sulfonic acid type ionic liquid, in particular to a preparation method of paraben ester compounds. Background technique [0002] Parabens, or parabens, are safe and effective preservatives commonly used in the world, widely used in food, cosmetics and pharmaceutical industries, and have good antibacterial effects on molds, yeasts and bacteria. Due to the characteristics of low toxicity, non-irritation and wide pH application range, paraben has become one of the important development products in my country to replace food preservatives such as sodium benzoate, and is a preservative and inhibitor with broad development prospects. Bacteria. At present, there are only a small number of manufacturers producing parabens in my country, and most of them use sulfuric acid as a catalyst. This method has disadvantages such as poor catalyst selectivity, many side reactions, serious...

Claims

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Application Information

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IPC IPC(8): C07C69/84C07C67/08B01J31/02
CPCY02P20/54
Inventor 周峰岩
Owner SHANDONG UNIV
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