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Method for preparing oligofuran dioctyl phthalate ester by directly esterifying and polymerizing

A technology of polyfurandicarboxylate and furandicarboxylate is applied in the fields of high molecular polymer materials and chemical industry, which can solve the problems of rare polymerization technology and products, and achieve the effect of efficient purification

Active Publication Date: 2013-05-22
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, the polymerization technology and products using 2,5-furandicarboxylic acid as a monomer are rare

Method used

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  • Method for preparing oligofuran dioctyl phthalate ester by directly esterifying and polymerizing
  • Method for preparing oligofuran dioctyl phthalate ester by directly esterifying and polymerizing
  • Method for preparing oligofuran dioctyl phthalate ester by directly esterifying and polymerizing

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Example 1: 10 mmol of 2,5-furandicarboxylic acid, 20 mmol of 1,2-ethylene glycol, and 0.1 mmol of PbO were added to a 50 mL round bottom flask. Under the protection of nitrogen, it was heated to 140°C; it was reacted at this temperature for 4h. Then the excess ethylene glycol and other impurities were distilled off under reduced pressure. The temperature was raised to 230°C, the vacuum was adjusted to 5mmHg, and the reaction was continued for 3h. Finally, 2 g of o-xylene was added, and the reaction was continued for 1 h under the above conditions. Cool to room temperature, add 10g of trifluoroacetic acid to dissolve, then drop the trifluoroacetic acid polymer solution into 60ml of methanol for precipitation, centrifuge, decant and remove the supernatant, the obtained polymer polyethylene furandicarboxylate The diester was a milky white solid and was dried under vacuum at 50°C for 12h. Calculated according to the feeding amount of the monomer 2,5-furandicarboxylic aci...

Embodiment 2

[0024] Embodiment 2: 10mmol 2,5-furandicarboxylic acid, 11mmol 1,3-propanediol, 0.03mmol ZnCl 2 Add it into a 50mL round bottom flask, heat to 160°C under nitrogen protection, react for 5h, then distill off excess propylene glycol under reduced pressure, raise the temperature to 210°C, adjust the vacuum to 3mmHg, continue the reaction for 2.5h, and finally add 4g biphenyl, continue to react under the above conditions for 1h. Cool to room temperature, add 5g of trifluoroacetic acid to dissolve, then drop its trifluoroacetic acid solution into 60ml of methanol for precipitation and separation, centrifuge, decant out the supernatant to obtain the polymer polytrimethylene furandicarboxylate as a milky white solid, Dry in vacuum at 50°C for 12h. Calculated according to the feeding amount of monomer 2,5-furandioic acid, the molar yield of the polymer is 96%. NMR spectrogram measurement results and attribution analysis are: 1 H NMR (TFA-d 1 , ppm): 2.05 (s, 2H, -O-CH 2 -CH 2 -)...

Embodiment 3

[0027] Embodiment 3: with 10mmol 2,5-furandicarboxylic acid, 30mmol 1,4-butanediol, 0.08mmolCa(OAc) 2 Added to a 50mL round bottom flask. Heated to 180°C under nitrogen protection and reacted for 6h. Excess butanediol was then distilled off under reduced pressure. The temperature was raised to 200°C, the vacuum degree was adjusted to 4mmHg, and the reaction was continued for 3.5h. Finally, 5 g of chlorobenzene was added, and the reaction was continued for 1 h under the above conditions. Cool to room temperature, add 15g of trifluoroacetic acid to dissolve, then drop its trifluoroacetic acid solution into 60ml of methanol for precipitation, centrifuge, decant out the supernatant to obtain the polymer polybutylene furandicarboxylate as a milky white solid. Dry in vacuum at 50°C for 12h. Calculated according to the feeding amount of monomer 2,5-furandicarboxylic acid, the molar yield of the polymer is 92%. NMR spectrogram measurement results and attribution analysis are: 1 ...

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Abstract

The invention discloses a method for preparing oligofuran dioctyl phthalate ester by directly esterifying and polymerizing. The method is characterized by comprising the following steps of: under the action of a compound catalyst, undergoing esterification and polymerization reactions on 2,5-furan dioctyl phthalate and low-carbon diatomic alcohol serving as raw materials at the temperature of 130-280 DEG C under the pressure of 2-15 mmHg for 1.5-16 hours; removing excessive low-carbon diatomic alcohol and other impurities by using a vacuum distillation or azeotropic distillation method; and purifying a polymer product with a dissolving-precipitating technology to obtain a high-quality oligofuran dioctyl phthalate ester product. The method has the advantages of high product yield, easinessin separating the product and good application prospect.

Description

technical field [0001] The present invention relates to the fields of high molecular polymer materials and chemical engineering, in particular, it relates to the direct esterification and polymerization of 2,5-furandicarboxylic acid and low-carbon diols under the action of catalysis to prepare high-quality polyfurandicarboxylates with high Methods for Molecular Materials. Background technique [0002] The synthesis of plastics, chemical fibers, polyester, etc. occupies a very important position in the synthesis of petrochemicals. The traditional preparation methods of these polymer materials mainly rely on fossil resources such as coal, oil and natural gas. After multi-step conversion, organic polymer material monomers and polymer products are obtained. Fossil resources such as coal, oil and natural gas have limited reserves and are not renewable. In order to achieve sustainable development, it is of great significance to develop and utilize renewable and abundant biomass ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G63/42C08G63/78
Inventor 徐杰马继平高进杜中田王敏张展
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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