Towards bio-based plasticizers with reduced toxicity: Synthesis and performance testing of a 3-methylphthalate

Plass, Carmen; Hiessl, Robert; Kleber, Joscha; Grimm, Axel; Langsch, Angelika; Otter, Rainer; Liese, Andreas; Gröger, Harald

doi:10.1016/j.scp.2020.100319

Cited by 6 publications

(11 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This stands in sharp contrast to the dramatic effect, which we could recently show for the formal insertion of a methyl group into DEHP. [19] Furthermore, in case of 1 (and also for the reference compound 3) the bicyclic structure seems to have a beneficial effect on the solution temperature in comparison with the standard plasticizer DEHP.…”

Section: Resultsmentioning

confidence: 98%

“…When realizing these synthetic concepts in our laboratory, the initial Diels-Alder reaction of 2-methylfuran (4) with maleic anhydride ( 5) was carried out analogously to our previous studies and literature under solvent-free conditions. [19,23,24] Without isolating the formed Diels-Alder adduct 6, subsequent hydrogenation at 80 bar of H 2 in the presence of 2 wt% of Pd/C as a catalyst and 2-methylfuran as a solvent (leading to a substrate concentration of 2.5 M) gave anhydride 7 in 52 % yield after recrystallization. This intermediate 7 was then further converted with alcohol 8 to the desired methyl-substituted bicyclic exo-type diester 1, which was obtained after a straightforward work-up (for details, see Supporting Information) in 58 % yield and with a purity of 96 % according to GC analysis (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

“…For comparison, there is a significant increase of the solution temperature by a formal introduction of a methyl group, which we could observe in our previous investigations. [19] The volatility (defined as the relative loss of mass from a specimen over a period) of the new candidates is below the one of DEHA (DOA) but still relatively high when considering the molecular weight. The volatility of the exo-type reference compound 3 with 2.59 % loss of mass at 130 °C for 24 h corresponds to that of Hexamoll DINCH with 2.48 %, which is higher than the volatility value of DINP.…”

Section: Resultsmentioning

confidence: 99%

“…[18] Complementing these efforts, we recently could show the suitability of a 3-methyl-substituted DEHP derivative, which is available from bio-based feedstocks, as a plasticizer. [19] In spite of promising performance properties such as the solution temperature in the PVC test, a drawback of this type of bio-based plasticizer is its too high viscosity.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Structure‐Performance Guided Design of Sustainable Plasticizers from Biorenewable Feedstocks

et al. 2021

Self Cite

View full text Add to dashboard Cite

The search for more sustainable solutions for plastics production, moving away from petrochemical feedstocks as today's major raw material basis, is a research area of increasing interest. This task goes far beyond the issue of designing greener polymers and their related monomers as tailor-made plastics require, besides the polymer itself, further components. These additives also need to be switched from typically fossilbased to bio-renewable raw materials. One of such necessary components for many applications are plasticizers, and a major application of them is related to polyvinyl chloride (PVC) as one of the leading polymers with a wide range of applications. Typically today's plasticizers are based on fossil feedstocks, and some of them such as specific ortho-phthalates as the most important product class of plasticizers are now subject to restrictions and authorization by the EU's REACH legislation due to their toxicological profile. In this contribution, we report the synthesis and technical evaluation of alternative, novel bicyclic plasticizer candidates, which are fully accessible from renewable feedstocks. In detail, these new plasticizer target molecules are based on the use of the furan-derivative 2-methylfuran, maleic anhydride and 2-ethylhexanol as bio-based starting materials. The synthetic concept consists of an initial Diels-Alder reaction with 2-methylfuran and a subsequent hydrogenation and optional esterification step. The applied reactions are wellknown as economic and sustainable technologies. Thus, not only the starting materials (being of bio-based origin) but also the selected reaction technologies for the syntheses of the target molecules are sustainable. Furthermore, a range of performance tests enabled an insight into structure-performance relationships and revealed promising plasticizing properties of this new bio-based plasticizer generation with, e. g., an attractive solution temperature fulfilling the criterium for a "fast fuser" as well as good compatibility with PVC.

show abstract

Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Structure‐Performance Guided Design of Sustainable Plasticizers from Biorenewable Feedstocks

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

“…Additives have historically been largely unregulated [ 74 ], and many are not required to be disclosed or labeled. While certain additives have shown to be biodegradable [ 75 ], many are not, as many products seek to be anti-microbial.…”

Section: Discussionmentioning

confidence: 99%

Microbial Consortia and Mixed Plastic Waste: Pangenomic Analysis Reveals Potential for Degradation of Multiple Plastic Types via Previously Identified PET Degrading Bacteria

Edwards

León-Zayas

Ditter

et al. 2022

IJMS

View full text Add to dashboard Cite

The global utilization of single-use, non-biodegradable plastics, such as bottles made of polyethylene terephthalate (PET), has contributed to catastrophic levels of plastic pollution. Fortunately, microbial communities are adapting to assimilate plastic waste. Previously, our work showed a full consortium of five bacteria capable of synergistically degrading PET. Using omics approaches, we identified the key genes implicated in PET degradation within the consortium’s pangenome and transcriptome. This analysis led to the discovery of a novel PETase, EstB, which has been observed to hydrolyze the oligomer BHET and the polymer PET. Besides the genes implicated in PET degradation, many other biodegradation genes were discovered. Over 200 plastic and plasticizer degradation-related genes were discovered through the Plastic Microbial Biodegradation Database (PMBD). Diverse carbon source utilization was observed by a microbial community-based assay, which, paired with an abundant number of plastic- and plasticizer-degrading enzymes, indicates a promising possibility for mixed plastic degradation. Using RNAseq differential analysis, several genes were predicted to be involved in PET degradation, including aldehyde dehydrogenases and several classes of hydrolases. Active transcription of PET monomer metabolism was also observed, including the generation of polyhydroxyalkanoate (PHA)/polyhydroxybutyrate (PHB) biopolymers. These results present an exciting opportunity for the bio-recycling of mixed plastic waste with upcycling potential.

show abstract

Synthesis and properties of bio‐based environmental plasticizer derived from oleic acid for poly (vinyl chloride)

Huang,

Nan,

et al. 2024

J of Applied Polymer Sci

View full text Add to dashboard Cite

Using the abundant and cost‐effective oleic acid and isosorbide with excellent properties as raw materials, the plasticizers of isosorbide di‐oleate (IDO) and isosorbide di‐epoxidized oleate (IDEO) with good plasticizing effect, low cost and green safety were synthesized by esterification and epoxidation reaction. The molecular structure of the synthesized plasticizers was characterized by FT‐IR and 1H NMR. The PVC shows better flexibility when IDEO or IDO plasticizer is used than commercial DOP. In particular, IDEO‐40 has 34% higher tensile strength and 17% higher elongation at break than DOP‐40. The introduction of epoxy groups on the carbon–carbon double bond of fatty acids meets the high thermal stability of plasticized film. The residual amount of IDEO‐40 is 7.01%, and at a high temperature of 180 °C, it can maintain high heat resistance for more than 220 min and transmittance of over 86%. Moreover, IDEO demonstrates excellent resistance to migration and volatilization. However, PVC films plasticized with IDO display reduced mechanical properties, cold resistance, and resistance to volatilization and migration due to the presence of non‐rotating carbon–carbon double bonds. The results indicate that these bio‐based plasticizers hold promise for practical applications in PVC products, offering improved environmental sustainability and performance characteristics.

show abstract

Towards bio-based plasticizers with reduced toxicity: Synthesis and performance testing of a 3-methylphthalate

Cited by 6 publications

References 22 publications

Structure‐Performance Guided Design of Sustainable Plasticizers from Biorenewable Feedstocks

Structure‐Performance Guided Design of Sustainable Plasticizers from Biorenewable Feedstocks

Microbial Consortia and Mixed Plastic Waste: Pangenomic Analysis Reveals Potential for Degradation of Multiple Plastic Types via Previously Identified PET Degrading Bacteria

Synthesis and properties of bio‐based environmental plasticizer derived from oleic acid for poly (vinyl chloride)

Contact Info

Product

Resources

About