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Method for synthesis of acetal/ketal in presence of acidic ionic liquid as catalyst?

An acidic ionic liquid, acetal technology, applied in the formation/introduction of ether group/acetal group/ketal group, chemical instruments and methods, preparation of organic compounds, etc. High requirements, complex preparation process and other problems, to achieve the effect of simple separation of catalyst and product, high yield and simple reaction operation

Active Publication Date: 2013-07-10
临沭县益兴供汽维修服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many reports on new catalysts for acetalization (ketone) reaction at home and abroad, including: molecular sieve [Roelofsen, D.P.; Bekkum, H.V.Synthesis1972, 419]; Zhongtong porous silica material MCM-41 [Iwamoto, M.; Namba, S.J. Am.Chem.Soc.2003,125,13032]; Functional ionic liquids [Li,D.-M.;Shi,F.;Peng,J.-J.;Guo,S.;Deng,Y.-Q.J. Org.Chem.2004,69,3582]; phosphotungstomolybdenum heteropolyacid supported on MCM-48 molecular sieve [Yang Shuijin, Zhu Peng. Journal of University of Science and Technology Beijing, 2008, 30(7): 791-794]; Trifluoromethanesulfonate salt [Nicholas M.Lonard, Matthew C.Oswald.J.Org.Chem.2002,67,5202-5207], tetrahydrocarbyl distannoxane [Lan Zhili, Lu Yan, Li Jing, et al. Journal of Catalysis, 2001 ,22(5):423-426.]; strong acid sulfonic acid resin [Jin Xinlei, Shi Jiehua. Industrial Catalysis, 2012, (8): 65-67]; fluorosulfonic acid resin [Peng Feng, Feng Jingxian. Guangzhou Chemical Industry, 2001,29(2):30-32.] etc., and have all obtained some different results, but the above-mentioned catalysts have their own shortcomings: as some catalysts are not easy to recycle and reuse, expensive, complex preparation process, and reaction equipment requirements High disadvantage

Method used

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  • Method for synthesis of acetal/ketal in presence of acidic ionic liquid as catalyst?
  • Method for synthesis of acetal/ketal in presence of acidic ionic liquid as catalyst?
  • Method for synthesis of acetal/ketal in presence of acidic ionic liquid as catalyst?

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Preparation of 3-(3-sulfonic acid) propylbenzothiazole bisulfate ionic liquid

[0023](1) Add benzothiazole (1.35g, 0.01mol) into a 25ml round-bottomed flask, and slowly add 1,3-propane sultone (1.464g, 0.012mol) dropwise under stirring conditions. After adding the raw materials, It was heated to 90°C for 4 hours to generate a large amount of white solid, which was washed three times with acetone and ether, filtered, and vacuum-dried at 80°C for 12 hours to obtain 2.47 g of white solid with a yield of 96.0%.

[0024] (2) Add 2.47g of the white solid obtained in step (1) into a 25ml round-bottomed flask, slowly add 0.94g (0.0096mol) of concentrated sulfuric acid (98wt%) under stirring in an ice bath, and add 2mL after the addition is complete distilled water at 80°C for 12 hours, the product was decompressed to remove water, washed three times with ethyl acetate, and dried in vacuum at 80°C for 12 hours to obtain 3.08 g of tan solid, namely 3-(3-sulfonic acid)...

Embodiment 2～43-

[0025] Example 2-4 Preparation of 3-(3-sulfonic acid) propylbenzothiazole hydrochloride acidic ionic liquid

[0026] Different acids (shown in Table 1) were used to replace the concentrated sulfuric acid described in Example 1, and other conditions and operations were the same as in Example 1. The test result of embodiment 2~4 is listed in table 1.

[0027] Table 1 3-(3-sulfonic acid) propylbenzothiazole hydrochloride acidic ionic liquid with different anions

[0028]

Embodiment 5

[0029] Example 5: Preparation of immobilized 3-(3-sulfonic acid) propylbenzothiazole bisulfate ionic liquid

[0030] Mix 10mL of tetraethyl orthosilicate and 7mL of absolute ethanol into a 50mL round bottom flask, stir evenly at room temperature, heat to 60°C, add 2.00g of 3-(3-sulfonic acid prepared in Example 1 Acid) Propylbenzothiazole bisulfate ionic liquid ([C 3 SO 3 HBth] HSO 4 ), 2mL of concentrated hydrochloric acid (36%wt%), 5mL of distilled water, stirred for 10min, aged at 60°C for 24h to form a gel, and then vacuum-dried at 100°C for 12h to obtain 5.82g of 3-(3- Sulfonic acid) Propylbenzothiazole bisulfate acidic ionic liquid [(CH 2 ) 3 SO 3 HBth] HSO 4 / silica gel catalyst, the loading of its ionic liquid is 34%.

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Abstract

The present invention discloses a method for synthesis of acetal / ketal in presence of acidic ionic liquid as catalyst, including: taking aldehyde / ketone and alcohol as raw materials and cyclohexane as a dehydrating agent, and performing azeotropic dehydration condensation under the catalytic action of the acidic ionic liquid at 80-120 DEG C. The acetal / ketal is obtained by aftertreatment of the reaction liquid after the reaction is completed. The acidic ionic liquid is a 3-(3-sulfonic acid)propyl benzothiazole salt acidic ionic liquid. The alcohol is C2-C4 organic alcohol. The method for synthesis of acetal / ketal catalyzed by the acidic ionic liquid has the advantages that the reaction operation is simple and convenient; separation of the catalyst from the product is easy; product purity and yield are high; and the catalyst can be reused and the catalytic activity thereof is essentially same. Accordingly, the method has broad application prospects.

Description

(1) Technical field [0001] The invention relates to a method for catalyzing the synthesis of acetal / ketone by an acidic ionic liquid, in particular to a novel immobilized 3-(3-sulfonic acid) propylbenzothiazole hydrochloride acidic ionic liquid, that is, silica gel-immobilized 3- (3-sulfonic acid) propyl benzothiazole hydrochloride acidic ionic liquid is a catalyst that catalyzes the condensation reaction of aldehydes / ketones and alcohols to prepare the corresponding acetals / ketones. (2) Background technology [0002] Acetal (ketone) is a kind of organic compound formed by the condensation of aldehyde (ketone) and alcohol. Compared with aldehyde (ketone), it has relatively stable properties. Many reagents that can react with aldehyde (ketone) such as Grignard reagent, Metal hydrides, etc., do not react with acetals (ketones). It is also stable to alkali, but when warmed in dilute acid, hydrolysis reaction will occur to generate corresponding aldehyde (ketone), which is a co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B41/04C07D317/12C07D317/72C07D317/22C07D317/16C07D317/48C07D409/04C07D319/06C07C41/56C07C43/305
Inventor 施介华姚志伟
Owner 临沭县益兴供汽维修服务有限公司
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