Bio-based 1,5-Pentanediol as a Replacement for Petroleum-Derived 1,6-Hexanediol for Polyester Polyols, Coatings, and Adhesives

Zheng, Lei; McClelland, Daniel J.; Rehmann, Kelsi M. S.; Barnett, Kevin J.; Huber, George W.; Klier, John D.

doi:10.1021/acssuschemeng.1c08198

Cited by 21 publications

(12 citation statements)

References 42 publications

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“…Various thermosets using bio-based templates have been synthesized recently, as the interest in using bio-based curable precursors (i.e., via thermal or UV-irradiation initiation) has been rising in recent decades [1][2][3][4]. The main reason several lipids or polyols are used for the production of polymerizable monomers is the applicability of their available naturally formed carbon structures [5][6][7]. The direct synthesis of numerous molecules, which can be obtained from agricultural productions would be complicated and, in most cases, economically unprofitable [5,8].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Bio-Based Thermoset Mixture Composed of Methacrylated Rapeseed Oil and Methacrylated Methyl Lactate: One-Pot Synthesis Using Formed Methacrylic Acid as a Continual Reactant

et al. 2023

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Methacrylated vegetable oils are promising bio-based polymerizable precursors for potential material application in several fields, such as coating technologies or 3D printing. The reactants’ availability for their production is an enormous advantage, but the modified oils also exhibit high apparent viscosity values and poor mechanical properties. This work focuses on a way to produce oil-based polymerizable material precursors in a mixture with a viscosity modifier in a one-batch process. The required methacrylic acid for the modification of epoxidized vegetable oils can be obtained as a secondary product of the methacrylation of methyl lactate forming a polymerizable monomer along with the acid. This reaction results in a yield of over 98% of methacrylic acid. Epoxidized vegetable oil can be added into the same batch using acid for oil modification which results in the one-pot mixture of both methacrylated oil and methyl lactate. The structural verifications of products were provided via FT-IR, 1H NMR, and volumetric methods. This two-step reaction process produces a thermoset mixture with a lower apparent viscosity of 142.6 mPa·s in comparison with methacrylated oil exhibiting a value of 1790.2 mPa·s. Other physical-chemical properties of the resin mixture such as storage modulus (E′ = 1260 MPa), glass transition temperature (Tg = 50.0 °C), or polymerization activation energy (17.3 kJ/mol) are enhanced in comparison with the methacrylated vegetable oil. The synthesized one-pot mixture does not require additional methacrylic acid due to the use of the one formed in the first step of the reaction, while the eventual thermoset mixture exhibits enhanced material properties compared to the methacrylated vegetable oil itself. Precursors synthesized in this work may find their purpose in the field of coating technologies, since these applications require detailed viscosity modifications.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Bio-Based Thermoset Mixture Composed of Methacrylated Rapeseed Oil and Methacrylated Methyl Lactate: One-Pot Synthesis Using Formed Methacrylic Acid as a Continual Reactant

et al. 2023

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“…Biomass-derived 1,5-pentanediol (PDO)-based polymers, including thermoplastics, have drawn increasing attention from both academia and industry to replace petroleum-derived diols. ,− PDO-based aliphatic polyesters have been synthesized using various aliphatic dicarboxylic acids with different chain lengths (carbon number: 4, 5, 6, 7, 9, 10, 12) . The crystallinity and melting point increased with the chain length of the diacid unit.…”

Section: Considerations For Future Biodegradable Plasticsmentioning

confidence: 99%

A Review of Biodegradable Plastics: Chemistry, Applications, Properties, and Future Research Needs

et al. 2023

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Environmental concerns over waste plastics’ effect on the environment are leading to the creation of biodegradable plastics. Biodegradable plastics may serve as a promising approach to manage the issue of environmental accumulation of plastic waste in the ocean and soil. Biodegradable plastics are the type of polymers that can be degraded by microorganisms into small molecules (e.g., H2O, CO2, and CH4). However, there are misconceptions surrounding biodegradable plastics. For example, the term “biodegradable” on product labeling can be misconstrued by the public to imply that the product will degrade under any environmental conditions. Such misleading information leads to consumer encouragement of excessive consumption of certain goods and increased littering of products labeled as “biodegradable”. This review not only provides a comprehensive overview of the state-of-the-art biodegradable plastics but also clarifies the definitions and various terms associated with biodegradable plastics, including oxo-degradable plastics, enzyme-mediated plastics, and biodegradation agents. Analytical techniques and standard test methods to evaluate the biodegradability of polymeric materials in alignment with international standards are summarized. The review summarizes the properties and industrial applications of previously developed biodegradable plastics and then discusses how biomass-derived monomers can create new types of biodegradable polymers by utilizing their unique chemical properties from oxygen-containing functional groups. The terminology and methodologies covered in the paper provide a perspective on directions for the design of new biodegradable polymers that possess not only advanced performance for practical applications but also environmental benefits.

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“…Many approaches have been developed to recycle or upcycle waste plastics into varied products, which include hydrogenolysis ( 37 , 38 ) and catalytic deconstruction (paraffins, olefins, and aromatics) ( 39 – 41 ), dissolution-based approaches (plastic resins with virgin properties) ( 42 ), functionalization (plastics with new properties) ( 43 ), and oxidation (oxygenates) ( 44 , 45 ). Compared with these routes, the key benefits of the approach reported are production of high-value (>$1600 per ton) monoaldehydes, dialdehydes, monoalcohols, and dialcohols ( 46 , 47 ), which can be done by using existing hydroformylation infrastructure.…”

Section: Technoeconomic Modeling and Life Cycle Assessmentmentioning

confidence: 99%

Hydroformylation of pyrolysis oils to aldehydes and alcohols from polyolefin waste

Jiang

et al. 2023

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Waste plastics are an abundant feedstock for the production of renewable chemicals. Pyrolysis of waste plastics produces pyrolysis oils with high concentrations of olefins (>50 weight %). The traditional petrochemical industry uses several energy-intensive steps to produce olefins from fossil feedstocks such as naphtha, natural gas, and crude oil. In this work, we demonstrate that pyrolysis oil can be used to produce aldehydes through hydroformylation, taking advantage of the olefin functionality. These aldehydes can then be reduced to mono- and dialcohols, oxidized to mono- and dicarboxylic acids, or aminated to mono- and diamines by using homogeneous and heterogeneous catalysis. This route produces high-value oxygenated chemicals from low-value postconsumer recycled polyethylene. We project that the chemicals produced by this route could lower greenhouse gas emissions ~60% compared with their production through petroleum feedstocks.

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Bio-based 1,5-Pentanediol as a Replacement for Petroleum-Derived 1,6-Hexanediol for Polyester Polyols, Coatings, and Adhesives

Cited by 21 publications

References 42 publications

Synthesis of Bio-Based Thermoset Mixture Composed of Methacrylated Rapeseed Oil and Methacrylated Methyl Lactate: One-Pot Synthesis Using Formed Methacrylic Acid as a Continual Reactant

Synthesis of Bio-Based Thermoset Mixture Composed of Methacrylated Rapeseed Oil and Methacrylated Methyl Lactate: One-Pot Synthesis Using Formed Methacrylic Acid as a Continual Reactant

A Review of Biodegradable Plastics: Chemistry, Applications, Properties, and Future Research Needs

Hydroformylation of pyrolysis oils to aldehydes and alcohols from polyolefin waste

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