Kinetic Modeling of the Synthesis Path for the Production of a Sustainable Epoxy Resin Based on Allyl Sorbate

Feigel, Matthias; Breitsameter, Jonas M.; Lechner, Korbinian; Rieger, Bernhard; Hinrichsen, Olaf

doi:10.1021/acs.iecr.3c01317

Cited by 4 publications

(11 citation statements)

References 34 publications

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“…Therefore, the reaction rate can be written as r = k normalD normalA c AS c normalM normalA with the reaction rate constant being k DA and the molar concentration c i of component i . The pre-exponential factor and activation energy are k 0,DA = 8.075 × 10 4 L/(mol s) and E A,DA = 60.32 kJ/mol, respectively …”

Section: Methodsmentioning

confidence: 99%

“…All reactions are of second order and acid-catalyzed with k i = k i * · c H 2 SO 4 using 0.5 vol % sulfuric acid. In our previous study, it was shown that the reversible reactions toward TACHC exhibit equal reactivity and thus can be treated with the same kinetic constants …”

Section: Methodsmentioning

confidence: 99%

“…Figure ) are a [4 + 2]-cycloaddition 1 , an esterification 2 , and an epoxidation reaction 3 . In our previous study, reaction models were established for each reaction and regressed with data acquired in laboratory measurements . The following sections briefly depict the reaction models with their particular kinetic parameters.…”

Section: Methodsmentioning

confidence: 99%

“…The following sections briefly depict the reaction models with their particular kinetic parameters. For further details, refer to our previous work …”

Section: Methodsmentioning

confidence: 99%

“…The synthesis and process modeling of the production of allyl sorbate are not within the scope of this study since the compound is already commercially available due to its application as a food flavoring agent. − Hence, the focus is on the process simulation of reactions 1 – 3 . Additionally, in our earlier work, the reaction progress thereof was measured to facilitate kinetic modeling of the particular reactions . The derived kinetic data are used to build the process model illustrated in the present study.…”

Section: Introductionmentioning

confidence: 99%

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Bridging the Gap from Laboratory to Production: Kinetic Modeling-Guided Process Development for a Novel Epoxy Resin

Feigel,

Breitsameter,

Rieger

et al. 2024

Ind. Eng. Chem. Res.

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The development of a production process of the sustainable epoxy resin 1,2-epoxy-6-methyl-triglycidyl-3,4,5-cyclohexanetricarboxylate (EGCHC) is presented. The three main sections of the suggested process flowsheet follow the reaction steps beginning with allyl sorbate and maleic anhydride. The Diels−Alder, allylation, and epoxidation reactions are simulated in Aspen Plus V12 and connected to form a single process train. To size and establish key process parameters, simulations supported by kinetic data for each reaction are performed. The [4 + 2]cycloaddition and epoxidation are implemented in multitubular plug flow reactors with downstream crystallizers for product purification. The allylation reaction is carried out in a reactive distillation column to separate the heavy boiling product from the condensate/allyl alcohol mixture, which is further processed to regain allyl alcohol. To decrease the intake of raw materials, recycle streams are added to each sections. EGCHC is achieved with a purity of 95%, which can be employed with standard curing agents to form dense cross-links due to an average number of epoxy groups >3.96 in the product stream. Furthermore, a techno-economic analysis is performed, showcasing a competitive market price for EGCHC with the given process design in the segment of biobased epoxy resins. This study demonstrates a comprehensive strategy that allows for rapid implementation of a novel synthesis process based on preliminary laboratory measurements and rating thereof.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…The following sections briefly depict the reaction models with their particular kinetic parameters. For further details, refer to our previous work …”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Bridging the Gap from Laboratory to Production: Kinetic Modeling-Guided Process Development for a Novel Epoxy Resin

Feigel,

Breitsameter,

Rieger

et al. 2024

Ind. Eng. Chem. Res.

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Superior glycidol-free chain extenders for post-consumer PET bottles and PET thermoform blends

Mestry,

Abdelwahab,

Elkholy

et al. 2024

Resources, Conservation and Recycling

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Recycling of Epoxy Resins with Degradable Structures or Dynamic Cross-Linking Networks: A Review

Li,

Wu,

et al. 2024

Ind. Eng. Chem. Res.

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Traditional epoxy resins (EPR), represented by bisphenol A type, have high chemical bond energy, low polarity, and stable chemical properties. The topological structure after curing makes EPR impossible for convenient recycling through heating or dissolution like thermoplastics. This results in traditional EPR having no advantage of efficient recycling, both in molecular structure and the combination morphology of polymer chains. However, introducing degradable or dynamically cross-linked structures into epoxy resins to modify their molecular structures will bring good special responsiveness, with the expectation to achieve efficient recycling while maintaining their original performance. This paper reviews the research progress of EPR with degradable or dynamically cross-linkable structures such as ester, acetal, and similar structures, Schiff bases, disulfide bonds, and Diels–Alder addition structures. This highlights the impact of these structures themselves on EPR recycling. We discussed the potential of these structures’ research findings in small-molecule organic chemistry for EPR recycling.

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Kinetic Modeling of the Synthesis Path for the Production of a Sustainable Epoxy Resin Based on Allyl Sorbate

Cited by 4 publications

References 34 publications

Bridging the Gap from Laboratory to Production: Kinetic Modeling-Guided Process Development for a Novel Epoxy Resin

Bridging the Gap from Laboratory to Production: Kinetic Modeling-Guided Process Development for a Novel Epoxy Resin

Superior glycidol-free chain extenders for post-consumer PET bottles and PET thermoform blends

Recycling of Epoxy Resins with Degradable Structures or Dynamic Cross-Linking Networks: A Review

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