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Application of SO3H- functionalized ionic liquid serving as catalyst to synthesis of 2-acetylthiophene

A SO3H-, 1.SO3H- technology, applied in the direction of organic chemistry, can solve the problems of high catalyst toxicity, large amount of three wastes, high cost, and achieve the effects of easy industrial production, high catalyst activity, and designable structure.

Inactive Publication Date: 2013-03-06
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These traditional methods usually bring many disadvantages, such as high catalyst toxicity, strong corrosiveness, difficult recycling of catalyst, and large amount of three wastes
In order to improve and overcome the above shortcomings, solid acid catalysts SnTf(18)-UVM-7 (Top Catal (2009) 52: 571578), βeta-zeolite HBEA (J.Mol.Catal.A: Chem.305 (2009): 100 103 ), Cs 2.5 h 0.5 PW 12 o 40 (Journal of Chemical Engineering of Universities, 2008, 22 (1): 28-133), loaded phosphotungstic acid and H-ZSM-5 (CN1954913) have been used to catalyze the preparation of 2-acetylthiophene, and have achieved good results. product selectivity and yield, but there are still some problems: the catalyst preparation process is complex and costly, the temperature required for the reaction is high, and many irritating and volatile organic solvents are used in the reaction process, such as acetonitrile. Such solvents have certain toxicity and are harmful to the environment, so they are not suitable for industrial scale production, which limits their availability.
And the research of using this type of ionic liquid to catalyze the preparation of 2-acetylthiophene has not been reported yet.

Method used

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  • Application of SO3H- functionalized ionic liquid serving as catalyst to synthesis of 2-acetylthiophene
  • Application of SO3H- functionalized ionic liquid serving as catalyst to synthesis of 2-acetylthiophene
  • Application of SO3H- functionalized ionic liquid serving as catalyst to synthesis of 2-acetylthiophene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-5

[0023] The ionic liquid [(HSO 3 -p) 2 im)][NTf 2 ] (0.165mmol), thiophene (10.4mmol), acetic anhydride (the amount in Table 1) was added to a 100ml round-bottomed flask equipped with a thermometer and reflux condenser, stirred magnetically, and reacted for 2h under normal pressure at 30℃ , And then stand and cool to room temperature, the reaction solution was distilled under reduced pressure to separate unreacted thiophene and acetic anhydride.

[0024] Table 1. The effect of reactant ratio on the reaction performance of thiophene and acetic anhydride

[0025]

[0026] It can be seen from the data in Table 1, the ionic liquid [(HSO 3 -p) 2 im)][NTf 2 ] Is a catalyst. When the amount of catalyst is only 1.6% (mol%) and the reaction temperature is only 30°C, the yield of 2-acetylthiophene can reach 97%, and the selectivity of 2-acetylthiophene is about 99%. The process does not need to add organic solvents and additives.

Embodiment 6-11

[0028] Add different ionic liquids (0.165mmol) as shown in Table 2, thiophene (10.4mmol), acetic anhydride (10.4mmol) into a 100ml round bottom flask equipped with a thermometer and reflux condenser, magnetically stirred, and at 60℃ The reaction was carried out under normal pressure for 2 hours, and then left to stand and cooled to room temperature. The reaction solution was distilled under reduced pressure to separate unreacted thiophene and acetic anhydride.

[0029] Table 2. Comparison of catalytic performance of different ionic liquids:

[0030] Example

[0031] From the data in Table 2, it can be seen that the anion is NTf 2 - SO 3 H-functionalized ionic liquid ([(HSO 3 -p) 2 im][NTf 2 ] And [(HSO 3 -p)im][NTf 2 ]) As a catalyst, when the amount of catalyst is only 1.6% (mol%), the reaction temperature is only 60°C, and thiophene is reacted with acetic anhydride in equal proportions, the yield of 2-acetylthiophene reaches 92%, and 2-acetylthiophene The selectivity reaches a...

Embodiment 12-16

[0033] Add ionic liquid, thiophene (52.4mmol), acetic anhydride (104.8mmol) into a 100ml round-bottomed flask equipped with a thermometer and reflux condenser, stir magnetically, and react at 60℃ for 2h under normal pressure, then stand still After cooling to room temperature, the reaction solution was distilled under reduced pressure to separate unreacted thiophene and acetic anhydride.

[0034] Table 3. The influence of ionic liquid cation structure on the acylation performance of thiophene and acetic anhydride

[0035] Example

[0036] It can be seen from the data in Table 3 that the anion is NTf 2 - SO 3 H-functionalized ionic liquid is used as a catalyst, when the amount of catalyst is only 1.6% (mol%) and the reaction temperature is only 60℃, the yield and selectivity of 2-acetylthiophene are very different with the change of cation structure. The ionic liquid of alkyl sulfonate imidazole cation can make the yield of 2-acetylthiophene reach 99%, and the selectivity of 2-ac...

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Abstract

The invention belongs to the technical field of fine chemical engineering and relates to application of SO3H- functionalized ionic liquid or a mixture of the SO3H- functionalized ionic liquid and other ionic liquids serving as a catalyst to synthesis of 2-acetylthiophene. The application is characterized by including: in the absence of solvent, by taking a mixture of one or more of sulfonic alkyl imidazole ionic liquid, sulfonic alkyl pyridine ionic liquid, sulfonic alkyl quaternary amine ionic liquid, sulfonic alkyl pyrazole ionic liquid, alkyl imidazole ionic liquid, alkyl pyridine ionic liquid, ethoxyl alkyl imidazole ionic liquid and ethoxyl alkyl pyridine ionic liquid as a reaction medium and the catalyst, stirring acetic anhydride and thiophene for reaction for 10min-120min at the temperature of 25-80 DEG C so that high-selectivity and high-yield 2-acetylthiophene is obtained. The ionic liquid serves as the reaction medium and the catalyst in the process, and the application has the advantages of good solvability, mild reaction condition, low vapor pressure, good structural designability and the like. Besides, the application is low in pollution to the environment and high in ion liquid catalyst activity, and is an efficient and green acetylthiophene synthesis method.

Description

Technical field [0001] The invention belongs to the technical field of fine chemicals, and relates to the preparation of 2-acetylthiophene, in particular to SO 3 The H-functionalized ionic liquid is used as a catalyst, and the non-functionalized ionic liquid is added as an auxiliary agent to synthesize 2-acetylthiophene. Background technique [0002] 2-Acetylthiophene is an important high-value-added organic synthesis intermediate and has a wide range of applications in the fields of medicine and pesticides. For example, preparation of 2-thiophene acetic acid, 2-thiophene acetyl chloride, 2-thiophene carboxylic acid, 2-thiophene carbonyl chloride, 2-thiophene glyoxylic acid and other thiophene derivatives. The preparation of 2-acetylthiophene is usually prepared by reacting thiophene as a starting material with acetic anhydride or acetyl chloride under the catalysis of inorganic liquid acid or mineral acid. These traditional methods usually bring many disadvantages, such as high...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/22
Inventor 杨淼刘秀梅李建新马慧媛颜佩芳王畅
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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