Synthesis of Poly(octylene 2,5-furandicarboxylate)

doi:10.3724/SP.J.1095.2013.20591

Chinese Journal of Applied Chemistry

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Synthesis of Poly(octylene 2,5-furandicarboxylate)

LI Liangui¹, LI Yang¹, YE Chong², ZHANG Qiang², JIANG Min², ZHOU Guangyuan^2,3*

(1.College of Chemistry and Life Sciences,Changchun University of Technology,Changchun 130012,China;
2.Key Laboratory of Polymer Ecomaterials,Changchun Institute of Applied Chemistry,
Chinese Academy of Scineces,Changchun 130022,China；
3.Changzhou Institute of Energy Storage Materital & Devices,Changzhou 213002,China)

Received:2012-12-17 Revised:2013-02-05 Published:2013-06-10 Online:2013-06-10

Abstract

Abstract: Poly(octylene 2,5-furandicarboxylate)(POF) was synthesized via the direct esterification method starting from 2,5-furandicarboxylic acid(FDCA) and 1,8-octylene glycol(1,8-ODO), in which tetrabutyl titanate was chosen as catalyst. Effect of the molar ratio of F-DCA to 1,8-ODO, dosage of tetrabutyl titanate, esterification temperature, polycondensation temperature on the esterification and polycondensation processes were studied in details. The optimized process conditions are:n(FDCA)∶n(1,8-ODO)=1∶1.2, tetrabutyl titanate dosage is 3×10-3 mol/mol FDCA, esterification temperature is 240 ℃, polycondensation temperature is 260 ℃, polycondensation time is 300 min. The relative molecular mass of the condensation product is the highest(ηSP/ρ=2.1 dL/g), and the carboxylic group content is the lowest(5.8 mol/t). Compared with ethylene glycol, using the 1,8-ODO reduced the molar ratio of FDCA to 1,8-ODO, and reduced the consumption of alcohol, meanwhile we got a high molecular mass polymer. The results of gas chromatography mass spectrometry(GC-MS) confirmed the composition of the esterification distillate and polycondensation product extractives. The results were found to be: the main ingredient of esterification distillate is H2O, and the other component is 1,8-ODO; polycondensation product extractives are composed of cyclohexanone (56%), (Z)-3-octene alcohol(18%), 4-methyl-3-amylene-2-ketone(17%), 4-hydro-xy-4-methyl-2-pentan-one(9%).

Key words: Poly(octylene furandicarboxylate), furandicarboxylic acid, direct esterification method, renewable resources, polymerization reaction

CLC Number:

O633.1

LI Liangui1, LI Yang1, YE Chong2, ZHANG Qiang2, JIANG Min2, ZHOU Guangyuan2,3*. Synthesis of Poly(octylene 2,5-furandicarboxylate)[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2013.20591.

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Synthesis of Poly(octylene 2,5-furandicarboxylate)

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