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Anionic polycondensation and equilibrium driven monomer formation of cyclic aliphatic carbonates.

ABSTRACT: The current work explores the sodium hydride mediated polycondensation of aliphatic diols with diethyl carbonate to produce both aliphatic polycarbonates and cyclic carbonate monomers. The lengths of the diol dictate the outcome of the reaction; for ethylene glycol and seven other 1,3-diols with a wide array of substitution patterns, the corresponding 5-membered and 6-membered cyclic carbonates were synthesized in excellent yield (70-90%) on a 100 gram scale. Diols with longer alkyl chains, under the same conditions, yielded polycarbonates with an M _w ranging from 5000 to 16 000. In all cases, the macromolecular architecture revealed that the formed polymer consisted purely of carbonate linkages, without decarboxylation as a side reaction. The synthetic design is completely solvent-free without any additional post purification steps and without the necessity of reactive ring-closing reagents. The results presented within provide a green and scalable approach to synthesize both cyclic carbonate monomers and polycarbonates with possible applications within the entire field of polymer technology.

SUBMITTER: Hua G

PROVIDER: S-EPMC9090641 | biostudies-literature | 2018 Nov

REPOSITORIES: biostudies-literature

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Anionic polycondensation and equilibrium driven monomer formation of cyclic aliphatic carbonates.

Hua Geng G Olsén Peter P Franzén Johan J Odelius Karin K

RSC advances 20181120 68

The current work explores the sodium hydride mediated polycondensation of aliphatic diols with diethyl carbonate to produce both aliphatic polycarbonates and cyclic carbonate monomers. The lengths of the diol dictate the outcome of the reaction; for ethylene glycol and seven other 1,3-diols with a wide array of substitution patterns, the corresponding 5-membered and 6-membered cyclic carbonates were synthesized in excellent yield (70-90%) on a 100 gram scale. Diols with longer alkyl chains, unde ...[more]

PMID: 35558332

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Project description:Polyether ketone (PEK) plastics are linear thermoplastic polymers connected by at least one ether bond and at least one ketone bond on the aryl group. The reason for their excellent heat resistance, rigidity, and mechanical strength is that their main molecular chain contains plenty of aromatic rings and polar carbonyl groups, and their molecular chain presents a large rigidity and strong intermolecular force. In addition, the main chain contains a considerable number of ether bonds, resulting in a certain toughness. However, polyether ketone materials have the disadvantage of poor solubility because of their excellent rigidity. To improve the solubility of polyether ketone, the preparation method of a novel nitrogenous heterocyclic polyaromatic ether monomer, 2-(4-chlorophenyl)-2,3-dihydrophthalazine-1,4-dione (CDD), was proposed, and its activity of polymerization was studied. The average molecular weight of the poly(aryl ether ketone) containing a nitrogenous heterocyclic polyaromatic ether group obtained by self-polycondensation of CDD was 4.181 × 103 kg/mol, and the yield was 90.5%. In order to further explore the activity of monomers, novel copolymerized poly(aryl ether ketone) (PBCD) containing a nitrogenous heterocyclic polyaromatic ether structure was prepared by ternary copolymerization with 4,4-difluorobenzophenone (DFBP) and bisphenol fluorene (BHPF) with high activity. The average molecular weight of PBCD was 72.793 × 103 kg/mol, the molecular weight distribution was 2.344, and the yield was 88.1%. Fourier transform infrared spectroscopy (FT-IR) and 1H NMR were used to confirm the structure of the obtained polymer. Through thermogravimetric analysis (TGA), the determined weight loss temperature of 5% under nitrogen was higher than 500 °C, indicating excellent thermal stability. Compared with the solubility of the binary copolymer containing fluorenyl poly(aryl ether ketone) (PBD), the polymer showed reasonable solubility in selective solvents such as chloroform and N,N-dimethylacetamide.

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Anionic polycondensation and equilibrium driven monomer formation of cyclic aliphatic carbonates.

Publications

Anionic polycondensation and equilibrium driven monomer formation of cyclic aliphatic carbonates.

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