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Method for preparing acetyl salicylamide

A technology of acetylsalicylic amide and salicylic amide, applied in the field of preparing acetylsalicylic amide, can solve problems such as non-reusable, unpleasant taste, pollute the environment, etc., and achieve the effect of saving production cost

Inactive Publication Date: 2010-08-18
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This process has the disadvantages of long reaction time, nitrobenzene that is volatile, unpleasant, and carcinogenic to human body as a solvent; the catalyst (anhydrous aluminum trichloride) is used in a large amount and cannot be reused; hydrolysis produces a large amount of aluminum-containing acid Wastewater, polluting the environment and many other disadvantages
Therefore, the production cost of the traditional process is high, the benefit space is not large, and its production volume is limited, which cannot meet the market's increasing demand for 5-acetylsalicylamide year by year

Method used

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  • Method for preparing acetyl salicylamide
  • Method for preparing acetyl salicylamide
  • Method for preparing acetyl salicylamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The preparation of ionic liquid (structural formula sees specification attached figure 1 )

[0028] 1-Butyl-3-methylimidazolium chloroaluminate [BMIM]Cl-nAlCl 3 (n=1.5-2.5) Preparation method of ionic liquid: under nitrogen protection, in a 500mL three-necked flask with a reflux condenser, 1.50mol (123g) of 1-methylimidazole, 1.7mol (158g) of The alkane was stirred and warmed up to 80°C, and the reaction was refluxed for 48h. Then cool at 0°C for 12h to crystallize, pour off the remaining unreacted liquid, then add 20mL of ethyl acetate to wash, the crude product is rotary evaporated at 80°C to remove residual ethyl acetate, and then dried in vacuum at 70°C for 24h. The yield of the product [BMIM]Cl is about 90%, and it is stored in a dry and inert atmosphere for future use.

[0029] The glove box was filled with nitrogen, and different amounts of anhydrous AlCl were slowly added in batches to the quantitative above-mentioned intermediate [BMIM]Cl at room temperature...

Embodiment 2

[0039] Same as Example 1 but keep the ionic liquid composition as n=2.0, only change the ionic liquid consumption to be 20mmol, 60mmol, 80mmol respectively, the results are shown in image 3 .

[0040] Such as image 3 Shown, when ionic liquid consumption is 20mmol (being promptly with salicylamide mol ratio 1: 1), due to reason such as stirring difficulty, cause the conversion rate of salicylamide and the yield of acetylsalicylamide to be all low; The increase of ionic liquid consumption, the conversion rate of salicylamide constantly increases, but after surpassing 40mmol, it is not obvious, and because the increase of side reaction, the yield of acetylsalicylamide declines instead, therefore, optimal ionic liquid consumption is 40mmol ( That is, the molar ratio with salicylamide is 2:1).

Embodiment 3

[0042] Same as Example 1 but keep the ionic liquid composition as n=2.0, only change the amount of acetyl chloride to be 20mmol, 60mmol, 80mmol respectively, the results are shown in Figure 4 .

[0043] Such as Figure 4 As shown, when the amount of acetyl chloride was 20mmol (i.e. 1:1 with salicylamide molar ratio), due to volatilization, partial hydrolysis and other reasons, the conversion rate of salicylamide and the yield of acetylsalicylamide were all low; Increase the amount of acetyl chloride to 40mmol (that is, the molar ratio of salicylamide to 2: 1), the conversion rate of salicylamide and the yield of acetyl salicylamide all increase, but not obviously, continue to increase the amount of acetyl chloride, salicylamide On the contrary, the conversion rate and the yield of acetylsalicylamide decrease slightly, therefore, the optimal amount of acetyl chloride is 20-40mmol (that is, the molar ratio to salicylamide is 1:1-2:1).

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Abstract

The invention discloses a method for preparing acetyl salicylamide, which takes 1-butyl-3-methylimidazole aluminum chloride acid (BMIM) Cl-nAlCl3 or N-butyl pyridine aluminum chloride acid (BPy) Cl-nAlCl3 ionic liquid as catalyst and solvent, and prepares the acetyl salicylamide by catalyzing salicylamide and acylation of acetylchloride. The preparation method comprises the reaction conditions asfollows: adding the salicylamide into the ionic liquid with the dosage of 1-4 times according to the molar ratio, and evenly stirring and mixing; adding the acetylchloride with the dosage of 1-4 times according to the molar ratio; and stirring to react for 25-400min at 25-55 DEG C, wherein n is equal to 1.5-2.5. The method for preparing the acetyl salicylamide has the advantages of simple and convenient technique, high conversion rate, good selectivity, high purity, short reaction time, easy control of reaction conditions, resource conservation, low danger and toxicity, little pollution and the like.

Description

technical field [0001] The invention relates to a method for preparing acetylsalicylicamide, in particular using 1-butyl-3-methylimidazolium chloroaluminate [BMIM]Cl-nAlCl 3 (n=1.5-2.5) or N-butylpyridine chloroaluminate [BPy]Cl-nAlCl 3 (n=1.5-2.5) A new method for preparing acetylsalicylamide by catalyzing the acylation of salicylamide with ionic liquid as catalyst and solvent. Background technique [0002] 5-acetylsalicylamide (5-acetylsalicylamide, abbreviated as: 5-ASA, molecular formula C 9 h 9 NO 3 ) is white or beige powder, odorless, tasteless, non-toxic, insoluble in water. 5-Acetylsalicylamide is an important pharmaceutical intermediate, which can be further synthesized into 5-bromoacetylsalicylamide, which is mainly used for the synthesis of the cardiovascular drug Laberol, and can also be used for the synthesis and treatment of other allergic diseases such as asthma, Drugs for allergic rhinitis, tuberculosis, urticaria, eczema, etc. [0003] The traditional...

Claims

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Application Information

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IPC IPC(8): C07C235/84C07C231/12B01J31/02
CPCY02P20/54
Inventor 陈维广殷恒波卢章准张运生
Owner JIANGSU UNIV
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