Light‐Driven Waste‐To‐Value Upcycling: Bio‐Based Polyols and Polyurethanes from the Photo‐Oxygenation of Cardanols

Stuhr, Robin; Bayer, Patrick; Stark, Christian B. W.; Wangelin, Axel Jacobi von

doi:10.1002/cssc.202101175

Cited by 13 publications

(6 citation statements)

References 62 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…3-Ethyl-2-pentene was converted to a mixture of products (entry 6). Although a 2% yield was obtained in the batch system after 10 h, yields of 30.9% (9) and 23.1% (10) were obtained in the continuous-flow system.…”

Section: ■ Results and Discussionmentioning

confidence: 90%

“…Epoxy alcohols are valuable building blocks for organic synthesis. − For instance, their semipinacol rearrangements are useful alternatives to aldol and related reactions for synthesizing β-hydroxycarbonyl compounds. − To date, considerable effort has been directed toward improving the synthetic routes to epoxy alcohols, as exemplified by the eco-friendly method reported by Adam and Nestler. − According to this method, the hydroperoxides, generated via the photooxygenation of alkenes using green, nontoxic, and inexpensive O 2 gas, are converted to epoxy alcohols through secondary epoxidation in the absence of additional oxidants. However, further research on the combination of the first (photooxygenation) and second (epoxidation) steps is required to reduce the reaction time and improve product yields.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Cascade Sequence of Photooxygenation–Epoxidation for the Flow Synthesis of Epoxy Alcohols

Kim,

Son,

Lim

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

A photooxygenation−epoxidation cascade sequence converting alkenes to epoxy alcohols was developed and evaluated in batch and continuous-flow systems. In the batch system, the undesired interactions between the photooxygenation and epoxidation catalysts resulted in suboptimal yields, whereas the fine control of reaction parameters in the flow system allowed the allyl hydroperoxides produced through photooxygenation of alkenes to be rapidly converted to epoxy alcohols in yields of up to 93%. The developed procedure allows one to avoid an important synthetic bottleneck, works well where traditional batch synthesis fails, and can be scaled up to meet the needs of industrial production, thus presenting a valuable addition to the toolbox of practicing organic chemists.

show abstract

Section: ■ Results and Discussionmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Cascade Sequence of Photooxygenation–Epoxidation for the Flow Synthesis of Epoxy Alcohols

Kim,

Son,

Lim

et al. 2024

J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…A future of using edible oils as a major alternative to petrochemical polyol may pose a critical issue of competition with food supplies. It is also possible to use non-edible vegetable oils such as Karanja oil [ 13 ], tung oil [ 17 , 18 ], tall oil [ 19 , 20 , 21 , 22 , 23 ] and cardanol [ 24 , 25 ]. Luo et al reported the feasibility of using crude glycerol in biopolyol synthesis and the production of PUR foams with apparent density of 43 kg/m 3 .…”

Section: Introductionmentioning

confidence: 99%

Open-Cell Spray Polyurethane Foams Based on Biopolyols from Fruit Seed Oils

Kurańska,

Malewska,

Ożóg

et al. 2024

Polymers

View full text Add to dashboard Cite

Natural oils from watermelon, cherry, black currant, grape and pomegranate fruit seeds were applied in the synthesis of biopolyols using the transesterification reaction. In this manuscript, the preparation possibility of open-cell foams from a polyurethane system in which petrochemical polyol was fully replaced with biopolyols is analyzed. Firstly, polyurethane foam systems were developed on a laboratory scale, and they were next tested under industrial conditions. It was shown that the foaming method has a significant impact on the foaming process and the cell structure of obtained foams as well as their thermal insulation properties. Based on the conducted research, it was found that the method of processing the polyurethane system has a significant impact on the properties of open-cell spray foams. Foams produced under industrial conditions have a much higher cell density, which has a positive effect on their selected physical–mechanical properties compared to foams produced on a laboratory scale. The open-cell biofoams obtained using a high-pressure machine had apparent densities 12–17 kg/m3, thermal conductivity coefficients 35–37 mW/m·K, closed-cell contents < 10% and were dimensionally stable at low and high temperatures.

show abstract

“…Based on this system, Li et al 24 added natural thylakoid membranes (TMs) and polyphosphate:AMP phosphotransferase for the simultaneous light-driven regeneration of NADPH and ATP. However, this ivSEB might suffer from substrate inhibition 24 , tedious preparation and instability of TMs, and reduced light penetration efficiency during scale-up 25 . Zhang et al designed a chemical-biological hybrid pathway to produce PHB from carbon dioxide (CO 2 ), in which an ivSEB was used to convert the CO 2 -derived methanol to PHB 26 .…”

Section: Introductionmentioning

confidence: 99%

ATP-free in vitro biotransformation of starch-derived maltodextrin into poly-3-hydroxybutyrate via acetyl-CoA

Wei,

Yang,

et al. 2024

Nat Commun

View full text Add to dashboard Cite

In vitro biotransformation (ivBT) facilitated by in vitro synthetic enzymatic biosystems (ivSEBs) has emerged as a highly promising biosynthetic platform. Several ivSEBs have been constructed to produce poly-3-hydroxybutyrate (PHB) via acetyl-coenzyme A (acetyl-CoA). However, some systems are hindered by their reliance on costly ATP, limiting their practicality. This study presents the design of an ATP-free ivSEB for one-pot PHB biosynthesis via acetyl-CoA utilizing starch-derived maltodextrin as the sole substrate. Stoichiometric analysis indicates this ivSEB can self-maintain NADP+/NADPH balance and achieve a theoretical molar yield of 133.3%. Leveraging simple one-pot reactions, our ivSEBs achieved a near-theoretical molar yield of 125.5%, the highest PHB titer (208.3 mM, approximately 17.9 g/L) and the fastest PHB production rate (9.4 mM/h, approximately 0.8 g/L/h) among all the reported ivSEBs to date, and demonstrated easy scalability. This study unveils the promising potential of ivBT for the industrial-scale production of PHB and other acetyl-CoA-derived chemicals from starch.

show abstract

Light‐Driven Waste‐To‐Value Upcycling: Bio‐Based Polyols and Polyurethanes from the Photo‐Oxygenation of Cardanols

Cited by 13 publications

References 62 publications

Cascade Sequence of Photooxygenation–Epoxidation for the Flow Synthesis of Epoxy Alcohols

Cascade Sequence of Photooxygenation–Epoxidation for the Flow Synthesis of Epoxy Alcohols

Open-Cell Spray Polyurethane Foams Based on Biopolyols from Fruit Seed Oils

ATP-free in vitro biotransformation of starch-derived maltodextrin into poly-3-hydroxybutyrate via acetyl-CoA

Contact Info

Product

Resources

About