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Synthesis of citric acid ether ester plasticizer

A citric acid ester and plasticizer technology, which is applied in the field of synthesis and preparation of new green and environmentally friendly citrate plasticizers, can solve the problems of poor durability and reduced compatibility of materials

Inactive Publication Date: 2015-11-25
TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, triethyl citrate (TEC), tributyl citrate (TBC), acetyl tributyl citrate (ATBC), etc. are easier to migrate and precipitate, which eventually leads to poor durability of the material
Improving the molecular weight of the plasticizer is a feasible method to prevent its migration. Although increasing the molecular weight can reduce the tendency of migration, too high a molecular weight will reduce the compatibility and cause phase separation. Therefore, the present invention develops and synthesizes relatively high molecular weight plasticizers. 500~2000g / mol new green citrate plasticizer

Method used

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  • Synthesis of citric acid ether ester plasticizer
  • Synthesis of citric acid ether ester plasticizer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: the synthesis of tri(butylene glycol monobutyl ester) citrate

[0015] ①Add 1mol (88.11g) of butyric acid, 1.2mol (108.14g) of butanediol, 0.94g of p-toluenesulfonic acid, and 25ml. Heat to 120°C and reflux for 4 hours from the first drop of water. During the reaction, the water phase in the lower layer of the water separator is continuously released and collected with a measuring cylinder to measure the water output. After the esterification reaction, distill off excess toluene under reduced pressure, then cool the reaction product below 60°C, transfer it into a separatory funnel and add an appropriate amount of distilled water, shake it fully and let it stand for 30 minutes. The distilled water and the organic phase are separated, and the lower water phase is released , the upper organic phase was poured into a flask and distilled and purified at a temperature of 95° C. and a pressure of 0.01 MPa to obtain butanediol monobutyl ester.

[0016] After the...

Embodiment 2

[0019] Embodiment 2: the synthesis of tri(diethylene glycol unit ethyl ester) citrate

[0020] ①Add 1mol (60.05g) of acetic acid, 1.2mol (127.33g) of diethylene glycol, 0.94g of p-toluenesulfonic acid, and 25ml of toluene into a 500ml four-neck flask equipped with a stirrer, water separator, serpentine condenser and thermometer . Heat to 120°C and reflux for 4 hours from the first drop of water. During the reaction, the water phase in the lower layer of the water separator is continuously released and collected with a measuring cylinder to measure the water output. After the esterification reaction, distill off the excess toluene under reduced pressure, then cool the reaction product to below 60%, then transfer it into a separatory funnel and add appropriate amount of distilled water and NaCl, shake it fully and let it stand in a water bath at 80°C for 30min, then separate the distilled water from the organic phase layer, release the organic phase and pour it into a flask at ...

Embodiment 3

[0024] Embodiment 3: the synthesis of tri(triethylene glycol monobutyl ester) citrate

[0025] ①Add 1mol (88.11g) of butyric acid, 1.2mol (180.20g) of triethylene glycol, 1.34g of p-toluenesulfonic acid, and 35ml. Heat to 120°C and reflux for 4 hours from the first drop of water. During the reaction, the water phase in the lower layer of the water separator is continuously released and collected with a measuring cylinder to measure the water output. After the esterification reaction, distill off excess toluene under reduced pressure, then cool the reaction product below 60°C, then transfer it into a separatory funnel and add appropriate amount of distilled water and NaCl, shake it fully and let it stand in a water bath at 80°C for 30 minutes, then separate the distilled water from the organic phase layer, release the organic phase and pour it into a flask to obtain triethylene glycol monobutyl ester after distillation and purification under reduced pressure at 100°C.

[0026...

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Abstract

The present invention discloses a method for synthesis of a new green environmentally friendly citric acid ether ester plasticizer from citric acid, a monobasic acid, and a dibasic alcohol as main raw materials by two-step esterification reaction, neutralizing, water washing, decolorizing, and vacuum distillation purification, wherein p-toluenesulfonic acid is used as a catalyst, toluene is used as a water-carrying agent, the raw materials are rich in sources, the reaction process is simple, safe and efficient, the relative molecular mass of the new citric acid ether ester is 500-2000g / mol, by increasing of the number of ester groups and the introduction of an ether bond, and the new citric acid ether ester exhibits better performance in anti-migration, cold resistance and flexibility, and can become a green environmentally friendly plasticizer with better performance.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to the synthesis and preparation of a novel green and environment-friendly citrate plasticizer. Background technique [0002] Citrate plasticizer is a safe, non-toxic, green and environmentally friendly plasticizer. It has the advantages of good compatibility with plastics, high growth rate and low volatility. It is widely used in medicine, food packaging, daily chemicals, etc. It is the first choice to replace o-phthalic plasticizers at home and abroad. However, triethyl citrate (TEC), tributyl citrate (TBC), acetyl tributyl citrate (ATBC), etc. are easier to migrate and precipitate, which ultimately leads to poor durability of the material. Improving the molecular weight of the plasticizer is a feasible method to prevent its migration. Although increasing the molecular weight can reduce the tendency of migration, too high a molecular weight will reduce the compatibilit...

Claims

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Application Information

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IPC IPC(8): C08K5/11C07C69/704C07C67/08
Inventor 万同林燕燕
Owner TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY
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