Über Decarboxylierung und Dissoziation heterocyclischer Dicarbonsäuren

Hopff, H.; Krieger, A.

doi:10.1002/hlca.19610440425

Cited by 25 publications

(24 citation statements)

References 3 publications

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“…All these attractive features have definitely motivated some studies about furanic polyamides through the years (see e.g. references 51,52,54,[148][149][150][151][152][153][154][155][156][157][158], including those dedicated to furanic -aliphatic and furanic -aromatic polyamides. Despite the enormous potential of this family of polymers, which are real biobased alternatives to existing petrochemical polyamides, recent literature dealing with FDCA is scarce, 51,52,54 with most published studies dating back from decades ago.…”

Section: Other Renewable Furanic Polycondensatesmentioning

confidence: 99%

“…Despite the enormous potential of this family of polymers, which are real biobased alternatives to existing petrochemical polyamides, recent literature dealing with FDCA is scarce, 51,52,54 with most published studies dating back from decades ago. [148][149][150]152,153,[155][156][157][158][159][160] There are, however, noticeable recent achievements envisaging a fruitful future 161 which will be the focus of the present section. The most obvious furan based monomers that have been described for the preparation of polyamides are FDCA and the corresponding dimethyl ester and acid dichloride derivatives; although 2,5bis(aminomethyl)furan (BAMF), and hydroxymethyl-2furancarboxamide (HMFA) were additionally used for this purpose (however, out of scope of this review).…”

Section: Other Renewable Furanic Polycondensatesmentioning

confidence: 99%

“…148,149 These authors reported the syntheses of linear polyamides from 21 heterocyclic dicarboxylic acids, including FDCA. 148 However, they found that heating the hexamethylene diammonium FDCA salt gave rise to strong decarboxylation.…”

Section: Furanic -Linear Aliphatic Polyamidesmentioning

confidence: 99%

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Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency

et al. 2015

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Motivated by a general concern on sustainability and environmental issues, a sparkling search for renewable-based polymers has grown exponentially in recent years. This search definitely spotlighted polyesters derived from 2,5-furandicarboxylic acid, among other polymers, as some of the most promising, especially due to the resemblance of this renewable monomer to the well-known petroleum-based terephthalic acid, as well as for the possibility of preparing innovative materials. The huge number of recent papers and patents about this family of polymers explore aspects such diverse as synthesis with other renewable-based monomers, leading to the preparation of materials with enhanced thermo-mechanical, biodegradability and liquid crystalline properties, among other features. Additional aspects pursued in such studies are innovation in the synthetic approaches or its optimisation; and also the development of applications for everyday-life objects like for example packaging materials, especially bottles, textiles, coating, toners, among many other uses. Despite this intense activity little has been reviewed recently about this unique family of polyesters, or derived polymers, as the only reviews on the subject date-back from the last century. In this perspective, the present appraisal aims at contributing to fulfil this literature gap, covering recent aspects related with challenges of developing polyesters, polyamides, or other polymers from 2,5-furandicarboxylic acid and their precursors. Emphasis is placed on monomer synthesis, polymerisation reactions, catalysts and applications.A tribute to 2,5-furandicarboxylic acid excellency and the myriad of novel polyesters, but also polyamides, among other polycondensates, is comprehensively done.

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Section: Other Renewable Furanic Polycondensatesmentioning

confidence: 99%

Section: Other Renewable Furanic Polycondensatesmentioning

confidence: 99%

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Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency

et al. 2015

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“…It was noted that the melting point, glass transition temperature, inherent viscosities, and molar masses vary considerably from one study to another. Moreover, previous studies pointed out the low thermal stability of FDCA, as well as several problems in terms of reactivity, thermal stability, and molar mass when trying to synthetize FDCA‐based polyamides. All these facts motivated us to study and extensively characterize a series of copolyphthalamides based on FDCA…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of polyamides from 2,5‐furandicarboxylic acid

Cousin

Galy

Rousseau

et al. 2017

J of Applied Polymer Sci

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The aim of this study is to investigate the synthesis of 2,5‐furandicarboxylic acid (FDCA)‐based copolyamides. Indeed, FDCA monomer may be a potential bio‐based alternative to phthalic acids. A series of polyamides and copolyamides, PA 6‐I(x)/6‐F(y), are synthesized in a pilot scale reactor by melt polycondensation of salts based on FDCA, isophthalic acid (IPA), and 1,6‐hexamethylenediamine. The chemical structure and composition of the resulting copolymers are extensively characterized by NMR (1H, 13C, and 2D), MALDI‐TOF as well as size exclusion chromatography and solution viscosimetry. Their thermal properties are studied by differential scanning calorimetry and TGA and also by a molecular modeling technique. It is pointed out that, during the synthesis, FDCA‐rich polymers overcome a massive decarboxylation of FDCA, preventing the production of high molar mass polymers. It is also found that all polymers are amorphous and that the glass transition temperatures decrease as the amount of FDCA in the polymer increases. This is confirmed by the results from molecular dynamics. In addition, it is observed that the copolymers become more hygroscopic when the amount of FDCA in the copolyamides increases. However, the water uptake of PA 6‐I(x)/6‐F(y) with 90 > x > 50 is lower than those of PA6 and PA 66 polyamides. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 45901.

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“…It was also found that decarboxylation of FDCA took place at around 195 °C and extensive N-methylation of (poly)amides occurred at elevated temperatures. [18][19][20]22 Recently…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Polymerization of Furan-2,5-Dicarboxylic Acid-Based Furanic-Aliphatic Polyamides as Sustainable Alternatives to Polyphthalamides

Jiao¹,

Maniar²,

Woortman³

et al. 2015

Biomacromolecules

117

124

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Furan-2,5-dicarboxylic acid (FDCA)-based furanic-aliphatic polyamides can be used as promising sustainable alternatives to polyphthalamides (semiaromatic polyamides) and be applied as high performance materials with great commercial interest. In this study, poly(octamethylene furanamide) (PA8F), an analog to poly(octamethylene terephthalamide) (PA8T), is successfully produced via Novozym 435 (N435)-catalyzed polymerization, using a one-stage method in toluene and a temperature-varied two-stage method in diphenyl ether, respectively. The enzymatic polymerization results in PA8F with high weight-average molecular weight (M̅(w)) up to 54000 g/mol. Studies on the one-stage enzymatic polymerization in toluene indicate that the molecular weights of PA8F increase significantly with the concentration of N435; with an optimal reaction temperature of 90 °C. The temperature-varied, two-stage enzymatic polymerization in diphenyl ether yields PA8F with higher molecular weights, as compared to the one-stage procedure, at higher reaction temperatures. MALDI-ToF MS analysis suggests that eight end groups are present in the obtained PA8F: ester/amine, ester/ester, amine/amine, acid/amine, ester/acid, acid/acid, ester/amide, and no end groups (cyclic). Compared to PA8T, the obtained PA8F possesses a similar Tg and similar crystal structures, a comparable Td, but a lower Tm.

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Über Decarboxylierung und Dissoziation heterocyclischer Dicarbonsäuren

Cited by 25 publications

References 3 publications

Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency

Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency

Synthesis and properties of polyamides from 2,5‐furandicarboxylic acid

Enzymatic Polymerization of Furan-2,5-Dicarboxylic Acid-Based Furanic-Aliphatic Polyamides as Sustainable Alternatives to Polyphthalamides

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