Azelaic Acid: A Bio-Based Building Block for Biodegradable Polymers

Todea, Anamaria; Deganutti, Caterina; Spennato, Mariachiara; Asaro, Fioretta; Zingone, Guglielmo; Milizia, Tiziana; Gardossi, Lucia

doi:10.3390/polym13234091

Cited by 18 publications

(17 citation statements)

References 77 publications

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“…The model reaction selected for the study was the polyesterification of glycerol (1,2,3‐propanetriol, or GLO) and azelaic acid (AZA) in a solvent‐less system yielding the corresponding poly(glycerolazelate), a product of potential relevance for dermatological applications whose market is predicted to reach USD 160 million by 2023 due to its esters and polyesters use in plastics, biodegradable polymers, biolubricants, and materials for electronics [17] …”

Section: Introductionmentioning

confidence: 99%

“…The model reaction selected for the study was the polyesterification of glycerol (1,2,3-propanetriol, or GLO) and azelaic acid (AZA) in a solvent-less system yielding the corresponding poly(glycerolazelate), a product of potential relevance for dermatological applications whose market is predicted to reach USD 160 million by 2023 due to its esters and polyesters use in plastics, biodegradable polymers, biolubricants, and materials for electronics. [17] The pharmacological applications of azelaic acid were studied since 1980's and it has been approved by both FDA (US Food and Drug Administration) and by EMA (European Medicines Agency) for external uses in the treatment of inflammatory acne vulgaris and in the treatment of skin pigmentation and melasma. [18] However, AZA suffers from lowsolubility, high melting point and large dosage requirement, which limit its wide application in cosmetics and pharmaceutical preparations.…”

Section: Introductionmentioning

confidence: 99%

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Rational Guidelines for the Two‐Step Scalability of Enzymatic Polycondensation: Experimental and Computational Optimization of the Enzymatic Synthesis of Poly(glycerolazelate)

et al. 2022

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The lipase‐catalyzed polycondensation of azelaic acid and glycerol is investigated according to a Design‐of‐Experiment approach that helps to elucidate the effect of experimental variables on monomer conversion, Mn and regioselectivity of acylation of glycerol. Chemometric analysis shows that after 24 h the reaction proceeds regardless of the presence of the enzyme. Accordingly, the biocatalyst was removed after a first step of synthesis and the chain elongation continued at 80 °C. That allowed the removal of the biocatalyst and the preservation of its activity: pre‐requites for efficient applicability at industrial scale. The experimental study, combined with docking‐based computational analysis, provides rational guidelines for the optimization of the regioselective acylation of glycerol. The process is scaled up to 73.5 g of monomer. The novelty of the present study is the rigorous control of the reaction conditions and of the integrity of the immobilized biocatalyst, which serve to avoiding any interference of free enzyme or fines released in the reaction mixture. The quantitative analysis of the effect of experimental conditions and the overcoming of some major technical bottlenecks for the scalability of enzymatic polycondensation opens new scenarios for industrial exploitation.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Rational Guidelines for the Two‐Step Scalability of Enzymatic Polycondensation: Experimental and Computational Optimization of the Enzymatic Synthesis of Poly(glycerolazelate)

et al. 2022

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“…Azelaic Acid Azelaic acid or nonanedioic acid is an α, ω-dicarboxylic acid with nine carbons. It has been recently reported as a valuable bio-based monomer for biodegradable polymers; for example, azelaic acid-based polyesters, terpolymer containing azelaic acid, and polyamide containing azelaic acid [172]. An example of an azelaic acid-based polymer is poly(ethylene azelate) which showed to be biodegradable at a comparable rate with poly-ε-caprolactone [173].…”

Section: Adipic Acidmentioning

confidence: 99%

“…An example of an azelaic acid-based polymer is poly(ethylene azelate) which showed to be biodegradable at a comparable rate with poly-ε-caprolactone [173]. The azelaic acid market is predicted to reach 160 million USD by 2023 [172].…”

Section: Adipic Acidmentioning

confidence: 99%

Contribution of Fermentation Technology to Building Blocks for Renewable Plastics

Lomwongsopon

Varrone

2022

Fermentation

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Large-scale worldwide production of plastics requires the use of large quantities of fossil fuels, leading to a negative impact on the environment. If the production of plastic continues to increase at the current rate, the industry will account for one fifth of global oil use by 2050. Bioplastics currently represent less than one percent of total plastic produced, but they are expected to increase in the coming years, due to rising demand. The usage of bioplastics would allow the dependence on fossil fuels to be reduced and could represent an opportunity to add some interesting functionalities to the materials. Moreover, the plastics derived from bio-based resources are more carbon-neutral and their manufacture generates a lower amount of greenhouse gasses. The substitution of conventional plastic with renewable plastic will therefore promote a more sustainable economy, society, and environment. Consequently, more and more studies have been focusing on the production of interesting bio-based building blocks for bioplastics. However, a coherent review of the contribution of fermentation technology to a more sustainable plastic production is yet to be carried out. Here, we present the recent advancement in bioplastic production and describe the possible integration of bio-based monomers as renewable precursors. Representative examples of both published and commercial fermentation processes are discussed.

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“…Biodegradable polymers can be synthesized by various methods like ring opening polymerization (ROP) [ 14 ], chemoenzymatic methods [ 8 ], photo-initiated radical polymerization [ 15 ], enzymatic polymerization [ 16 ], cationic, anionic, enzymatic, coordinative and radical ring opening polymerization [ 17 ]. The definition of biodegradable polymers according to the American Society for Testing and Materials (ASTM) is "they are the polymers that degrade or decompose under chemical, physical and biological interactions with microorganisms from environment, such as bacteria, fungus and algae” [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

A road map on synthetic strategies and applications of biodegradable polymers

et al. 2022

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Biodegradable polymers have emerged as fascinating materials due to their non-toxicity, environmentally benign nature and good mechanical strength. The toxic effects of non-biodegradable plastics paved way for the development of sustainable and biodegradable polymers. The engineering of biodegradable polymers employing various strategies like radical ring opening polymerization, enzymatic ring opening polymerization, anionic ring opening polymerization, photo-initiated radical polymerization, chemoenzymatic method, enzymatic polymerization, ring opening polymerization and coordinative ring opening polymerization have been discussed in this review. The application of biodegradable polymeric nanoparticles in the biomedical field and cosmetic industry is considered to be an emerging field of interest. However, this review mainly highlights the applications of selected biodegradable polymers like polylactic acid, poly( ε -caprolactone), polyethylene glycol, polyhydroxyalkanoates, poly(lactide-co-glycolide) and polytrimethyl carbonate in various fields like agriculture, biomedical, biosensing, food packaging, automobiles, wastewater treatment, textile and hygiene, cosmetics and electronic devices.

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Azelaic Acid: A Bio-Based Building Block for Biodegradable Polymers

Cited by 18 publications

References 77 publications

Rational Guidelines for the Two‐Step Scalability of Enzymatic Polycondensation: Experimental and Computational Optimization of the Enzymatic Synthesis of Poly(glycerolazelate)

Rational Guidelines for the Two‐Step Scalability of Enzymatic Polycondensation: Experimental and Computational Optimization of the Enzymatic Synthesis of Poly(glycerolazelate)

Contribution of Fermentation Technology to Building Blocks for Renewable Plastics

A road map on synthetic strategies and applications of biodegradable polymers

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