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Method for synthesizing tributyl 2-acetylcitrate catalyzed by N-methyl-2-pyrrolidone bisulfate ionic liquid

A technology of acetyl tributyl citrate and methyl pyrrolidone is applied in chemical instruments and methods, preparation of organic compounds, organic compounds/hydrides/coordination complex catalysts, etc., and can solve the problem that tributyl citrate cannot be prepared integrally Ester and acetyl tributyl citrate, product stratification is not obvious, easy to produce side reactions and other problems, to achieve the effect of convenient separation, simple reaction and environmental protection, and simplified process flow

Inactive Publication Date: 2014-04-23
ZHEJIANG UNIV OF TECH
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  • Abstract
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Problems solved by technology

[0003] Most of the catalysts used in traditional synthesis methods are concentrated sulfuric acid. This method has disadvantages such as low esterification efficiency, serious equipment corrosion, easy side reactions, large amounts of acidic wastewater, and environmental pollution. focus of research
[0004] CN102659589A discloses a method for catalyzing and synthesizing acetyl tributyl citrate with caprolactam ionic liquid. The method uses caprolactam ionic liquid as a catalyst to catalyze the reaction of acetic anhydride and tributyl citrate to generate acetyl tributyl citrate. However, the method There are shortcomings such as inconspicuous separation of products, inability to prepare tributyl citrate and acetyl tributyl citrate in one piece, and the need for washing. The present invention has obvious advantages in these aspects

Method used

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  • Method for synthesizing tributyl 2-acetylcitrate catalyzed by N-methyl-2-pyrrolidone bisulfate ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Preparation of tributyl citrate (TBC):

[0026] Take 0.1 mol of citric acid and 0.38 mol of n-butanol in a 250ml flask, add 15% (mass ratio) catalyst, and react at 130°C for 2.5 hours. After the reaction is over, observe the product, which is obviously divided into upper and lower layers, and the alcohol and water are distilled out under reduced pressure to prepare for the next step of reaction.

[0027] (2) Preparation of acetyl tributyl citrate (ATBC):

[0028] Add 0.6mol acetic anhydride to the reaction product of the previous step, react at 70°C for 2.5 hours, and cool down. The product is divided into upper and lower layers. Take the upper layer product (the lower layer is the catalyst, which is recycled), and distill off the excess acid and water under reduced pressure. Acetyl tributyl citrate with high purity was obtained, decolorized by activated carbon to obtain the finished product, and the yield was 99.4%. The ester content is ≥99.5% as detected by gas ...

Embodiment 2

[0030] (1) Preparation of tributyl citrate (TBC):

[0031] Take 0.1 mol of citric acid and 0.45 mol of n-butanol in a 250ml flask, add 15% (mass ratio) catalyst, and react at 120°C for 3 hours. After the reaction is over, observe the product, which is obviously divided into upper and lower layers, extract the alcohol and water, and prepare for the next step of reaction.

[0032] (2) Preparation of acetyl tributyl citrate (ATBC):

[0033] Add 0.8mol acetic anhydride to the reaction product of the previous step, react at 70-80°C for 2.5 hours, cool down, take the upper layer product, extract the excess acid and water in it, and obtain acetyl tributyl citrate with high purity, decolorize with activated carbon to obtain the finished product, Yield 99.1%. The ester content is ≥99.5% as detected by gas chromatography.

Embodiment 3

[0035] (1) Preparation of tributyl citrate (TBC):

[0036] Take 0.2mol of citric acid and 0.8mol of n-butanol in a 250ml flask, add 18% (mass ratio) catalyst, and react at 100°C for 2 hours. After the reaction is over, observe the product, which is obviously divided into upper and lower layers, extract the alcohol and water, and prepare for the next step of reaction.

[0037] (2) Preparation of acetyl tributyl citrate (ATBC):

[0038] Add 0.8mol acetic anhydride to the reaction product of the previous step, react at 80°C for 2.5 hours, cool down, take the upper product, extract the excess acid and water in it, and obtain acetyl tributyl citrate with high purity, decolorize with activated carbon to obtain the finished product, the yield 99.2%. The ester content is ≥99.5% as detected by gas chromatography.

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Abstract

The invention discloses a method for synthesizing tributyl 2-acetylcitrate catalyzed by N-methyl-2-pyrrolidone bisulfate ionic liquid, which comprises the following steps: 1) taking citric acid and n-butyl alcohol as raw materials, and N-methyl-2-pyrrolidone bisulfate ionic liquid as a catalyst, fully reacting and naturally layering a reaction mixture, directly performing reduced pressure distillation on the residual n-butyl alcohol and moisture to obtain the crude products; 2) adding acetic anhydride in the crude products obtained in the step 1), fully reacting and performing standing and layering, taking a substance at an upper level and performing reduced pressure distillation to obtain the crude products, and decolouring the crude products by active carbon to obtain the tributyl 2-acetylcitrate. The method has the advantages of high utilization rate of raw materials, high yield and good quality of products, low catalyst cost, mild reaction condition, repeatedly used catalyst, convenient products separation, environmental protection and no pollution.

Description

technical field [0001] The invention relates to a method for catalytically synthesizing acetyl tributyl citrate by using N-methylpyrrolidone bisulfate ionic liquid, and belongs to the field of chemical synthesis and technology. Background technique [0002] Acetyl tributyl citrate is a "green" environmentally friendly plasticizer, which has the advantages of non-toxic, odorless, anti-mildew, and good plasticizing effect. It is widely used in food packaging, medical polyvinyl chloride, and precision instrument packaging. The main plasticizer of ethylene-vinylidene chloride copolymer. [0003] Most of the catalysts used in traditional synthesis methods are concentrated sulfuric acid. This method has disadvantages such as low esterification efficiency, serious equipment corrosion, easy side reactions, large amounts of acidic wastewater, and environmental pollution. to be the focus of research. [0004] CN102659589A discloses a method for catalyzing and synthesizing acetyl tri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/67C07C67/313B01J31/02
CPCC07C67/08C07C69/67C07C69/704
Inventor 郭红云陆晨曦滕茂林丁茂华
Owner ZHEJIANG UNIV OF TECH
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