Dehydration Polycondensation of Dicarboxylic Acids and Diols Using Sublimating Strong Brønsted Acids
Abstract
We investigated catalytic activities of strong brønsted acids for dehydration polycondensations of dicarboxylic acids and diols, which were carried out at low temperature (<100 °C) under reduced pressure (0.3-3 mmHg). Strong Brønsted acids, bis(perfluoroalkanesulfonyl)imide and perfluoroalkanesulfonic acid, showed higher activity than p-toluenesulfonic acid or rare-earth catalysts at 60 °C. In particular, bis(nonafluorobutanesulfonyl)imide (Nf(2)NH) showed the highest activity to synthesize not only aliphatic polyester (M(n) > 19000) but also aromatic polyester (M(n) > 7000). The used Nf(2)NH was sublimated from the reaction flask during polycondensation, and the sublimate, Nf(2)NH, was extra pure so that we can reuse the catalyst without loss of the activity in the dehydration polycondensations.
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Several classes of organocatalysts have been used to catalyze the step-growth polymerization of diols with diacids or carbonates, including strong Brønsted acids and organic bases.
“Several classes of organocatalysts have been used to catalyze the SGP of diols with diacids or carbonates, including strong Brønsted acids such as H2SO4, triflic acid, p-toluenesulfonic acid (PTSA), bis(trifluoromethanesulfonyl)-imide (Tf2NH), 243,244 and organic bases such as TBD, 221,245-247 MTBD, 248 1-n-butyl-3-methylimidazol-2-carboxylate.249”
From Catalysis as an Enabling Science for Sustainable Polymers (2018) · cites this paper as [244]
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Catalysis as an Enabling Science for Sustainable Polymers
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- Authors
- Moyori, T., Tang, T., & Takasu, A.
- Affiliations
- Nagoya Institute of Technology (JP)
- Corresponding author
- Takasu, Akinori
- Venue
- Biomacromolecules
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-04-30
- Volume
- 13
- Issue
- 5
- Pages
- 1240-1243
- ISSN
- 1525-7797 (ISSN-L)
- 1526-4602
- OpenAlex
- W2313236563
- Cited by
- 23
- References
- 31
- Citations by year
- 2023: 1 · 2022: 2 · 2021: 2 · 2020: 1 · 2019: 1 · 2018: 3 · 2017: 4 · 2015: 3 · 2014: 3 · 2013: 3
- FWCI
- 1.17
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Biomacromolecules (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Materials Science › Biomaterials › biodegradable polymer synthesis and properties
- Physical Sciences › Materials Science › Polymers and Plastics › Synthesis and properties of polymers
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Keywords
- dicarboxylic acids, diols, catalyst recycling, aliphatic polyesters, aromatic polyesters, low-temperature polymerization
- MeSH terms
- Acids, Alcohols, Dehydration, Dicarboxylic Acids, Polyesters, Molecular Structure
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