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Levoglucosan and levoglucosenone as bio-based platforms for polymer synthesis

POLYMER CHEMISTRY (2023)

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Article Chemistry, Multidisciplinary

Precision native polysaccharides from living polymerization of anhydrosugars

Lianqian Wu et al.

Summary: The composition, sequence, length and type of glycosidic linkage of polysaccharides significantly influence their biological and physical properties. However, the study of the relationship between structure and function in polysaccharides is challenging due to the difficulty in obtaining well-defined polysaccharides in sufficient quantities. In this study, we report a chemical approach to synthesize precision polysaccharides with native glycosidic linkages using living cationic ring-opening polymerization of 1,6-anhydrosugars. Our method allows the synthesis of well-defined polysaccharides with tunable molecular weight, low dispersity and excellent regio- and stereo-selectivity. We also demonstrate the potential utility of these precision polysaccharides as chemically recyclable materials with tailored thermal and mechanical properties.

NATURE CHEMISTRY (2023)

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Article Polymer Science

Biobased Copolymers via Cationic Ring-Opening Copolymerization of Levoglucosan Derivatives and ε-Caprolactone

Mayuri K. Porwal et al.

Summary: Simultaneousring-opening copolymerization is a powerful strategy for highly functionalcopolymer synthesis. This study introduces a scalable synthetic platformto produce unique polysaccharides with different functional groups frombiomass-derived levoglucosan and ε-caprolactone. Biocompatible and recyclablebismuth triflate was identified as the optimal catalyst for the copolymerization.Copolymers from tribenzyl levoglucosan and ε-caprolactone and from tribenzyland triallyl levoglucosan were successfully synthesized.

ACS MACRO LETTERS (2023)

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Review Environmental Sciences

Agro-forestry waste management- A review

Juhi Gupta et al.

Summary: Agroforestry waste not only produces a significant amount of residues and products, but also holds important implications for the economy and environment. Effective management of waste collection, transportation, and recycle or valorization is key to maintaining a circular sustainable bioeconomy, requiring the employment of appropriate pretreatment technologies. Additionally, the introduction of appropriate policies and global initiatives are crucial in addressing the challenges faced by the agroforestry sectors.

CHEMOSPHERE (2022)

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Article Polymer Science

Synthesis and Enzymatic Degradation of Sustainable Levoglucosenone-Derived Copolyesters with Renewable Citronellol Side Chains

Sami Fadlallah et al.

Summary: A renewable five-membered lactone containing citronellol was synthesized and a one-pot two-step pathway was developed to produce a mixture of Lactol-citro molecules. The study found that temperature affects the chemical shifts of the hydroxyls and the 5ML:6ML ratio. Polymers with low glass transition temperatures and cross-linked citronellol chains were successfully prepared.

POLYMERS (2022)

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Review Chemistry, Multidisciplinary

Levoglucosenone: Bio-Based Platform for Drug Discovery

Jason E. Camp et al.

Summary: This review discusses the conversion of levoglucosone (LGO) into biologically active compounds and future research directions related to this platform molecule.

FRONTIERS IN CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Cyrene: A bio-based sustainable solvent for organic synthesis

Dickson Kong et al.

Summary: This review discusses the applications of the green solvent Cyrene in organic synthesis. By replacing traditional solvents, Cyrene has been proven to be a safe and sustainable alternative, showing good performance in various chemical reactions.

SUSTAINABLE CHEMISTRY AND PHARMACY (2022)

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Article Chemistry, Multidisciplinary

Lipase-Catalyzed Synthesis of Biobased Polyesters Containing Levoglucosan Units

Jonathan Bassut et al.

Summary: Levoglucosan (LGA) has gained increasing attention as a pyrolytic sugar with potential applications in various industries. In this study, a series of LGA-containing polymers were synthesized for the first time through a regioselective transesterification reaction, and the effect of LGA content on the properties of the polymers was investigated.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2022)

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Article Chemistry, Multidisciplinary

Sustainable One-Pot Synthesis and Polycondensation of a Levoglucosenone-Derived Cyclic Acetal Diol

Florian Diot-Neant et al.

Summary: The one-pot two-step hydration/reduction reaction of levoglucosenone was improved by using a more sustainable base, K3PO4, instead of Et3N. The resulting sterically hindered diol was then used to prepare bio-based polyesters with high thermal stability and glass transition temperatures. Two different polymerization strategies were implemented and assessed for their environmental impacts.

ACS SUSTAINABLE CHEMISTRY & ENGINEERING (2022)

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Review Chemistry, Multidisciplinary

Cyrene: a bio-based novel and sustainable solvent for organic synthesis

Naya A. Stini et al.

Summary: Cyrene, a biomass-derived solvent, is biodegradable, non-mutagenic and non-toxic. Since 2014, it has been increasingly used as a substitute for toxic organic solvents in various research fields.

GREEN CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Stereoregular functionalized polysaccharides via cationic ring-opening polymerization of biomass-derived levoglucosan

Mayuri K. Porwal et al.

Summary: This study demonstrates the facile synthesis of functional stereoregular polysaccharides with 1,6-alpha linkages from biomass-derived levoglucosan through cationic ring-opening polymerization. Computational studies show that metal triflate catalysts exhibit high coordination efficiency with levoglucosan derivatives and low toxicity compared to previous catalysts. The reported polymers have good thermal stability and a wide glass transition temperature window.

CHEMICAL SCIENCE (2022)

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Article Polymer Science

Green synthesis of 2-deoxy-D-ribonolactone from cellulose-derived levoglucosenone (LGO): A promising monomer for novel bio-based polyesters

F. Diot-Neant et al.

Summary: The study successfully greened up the reaction of levoglucosenone, increasing the yield and reducing the occurrence of side reactions. A new synthesis reaction was carried out based on levoglucosenone, preparing a polymer that shows promise as a potential alternative to petrochemical products.

EUROPEAN POLYMER JOURNAL (2021)

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Article Polymer Science

Ring-Opening Metathesis Polymerization of Unsaturated Carbohydrate Derivatives: Levoglucosenyl Alkyl Ethers

Tapas Debsharma et al.

Summary: Polymerization of biomass-derived levoglucosenyl alkyl ethers using the Grubbs catalyst yields thermoplastic polyacetals with specific thermal properties in various solvents. The initiation step of the polymerization process is slow, with catalyst consumption leading to deactivation of chain ends.

MACROMOLECULES (2021)

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Review Energy & Fuels

Catalytic Strategies for Levoglucosenone Production by Pyrolysis of Cellulose and Lignocellulosic Biomass

Shinji Kudo et al.

Summary: Levoglucosenone (LGO), a biobased compound generated through cellulose pyrolysis, has recently seen large-scale industrial production and expanded applications. Existing production methods can be categorized into three types based on catalytic strategies. Synthesizing previous achievements can inform future research directions for improved production methods.

ENERGY & FUELS (2021)

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Article Polymer Science

Sustainable Hyperbranched Functional Materials via Green Polymerization of Readily Accessible Levoglucosenone-Derived Monomers

Sami Fadlallah et al.

Summary: The homopolymerization of bis(gamma-lactone) 2H-HBO-HBO in basic conditions was reported for the first time, resulting in renewable poly(vinyl-ether lactone) copolymers with a highly hyperbranched structure. Polymerization of (S)-gamma-hydroxymethyl-alpha,beta-butenolide (HBO) was also conducted on a large scale, producing a new hyperbranched polymer. Both types of polymers have potential for industrial-scale production due to their interesting properties and easy preparation.

MACROMOLECULAR RAPID COMMUNICATIONS (2021)

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Article Chemistry, Multidisciplinary

Sustainable Synthesis and Polycondensation of Levoglucosenone-Cyrene-Based Bicyclic Diol Monomer: Access to Renewable Polyesters

Florian Diot-Neant et al.

CHEMSUSCHEM (2020)

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Article Polymer Science

Synthesis of Functionally and Stereochemically Diverse Polymers via Ring-Opening Metathesis Polymerization of Derivatives of the Biomass-Derived Platform Molecule Levoglucosenone Produced at Industrial Scale

Martin G. Banwell et al.

MACROMOLECULES (2020)

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Article Polymer Science

A straightforward access to functionalizable polymers through ring-opening metathesis polymerization of levoglucosenone-derived monomers

Sami Fadlallah et al.

EUROPEAN POLYMER JOURNAL (2020)

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Article Polymer Science

Chemo-enzymatic synthesis of a levoglucosenone-derived bi-functional monomer and its ring-opening metathesis polymerization in the green solvent Cyrene™

Sami Fadlallah et al.

POLYMER CHEMISTRY (2020)

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Review Chemistry, Multidisciplinary

Levoglucosan: a promising platform molecule?

Ivaldo Itabaiana et al.

GREEN CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Ring-Opening Metathesis Polymerization of Biomass-Derived Levoglucosenol

Tapas Debsharma et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Organic

Synthesis and fungicidal activity of methylsulfanylmethyl ether derivatives of levoglucosenone

Bulat T. Sharipov et al.

CHEMISTRY OF HETEROCYCLIC COMPOUNDS (2019)

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Review Chemistry, Applied

3D printing using plant-derived cellulose and its derivatives: A review

Lei Dai et al.

CARBOHYDRATE POLYMERS (2019)

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Article Meteorology & Atmospheric Sciences

Biomass waste utilisation in low-carbon products: harnessing a major potential resource

Nimisha Tripathi et al.

NPJ CLIMATE AND ATMOSPHERIC SCIENCE (2019)

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Review Chemistry, Organic

Levoglucosenone and Its New Applications: Valorization of Cellulose Residues

Maria B. Comba et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Multidisciplinary

Organic solvent- and catalyst-free Baeyer-Villiger oxidation of levoglucosenone and dihydrolevoglucosenone (Cyrene (R)): a sustainable route to (S)-gamma-hydroxymethyl-alpha,beta-butenolide and (S)-gamma-hydroxymethyl-gamma-butyrolactone

Guillaume Bonneau et al.

GREEN CHEMISTRY (2018)

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Article Polymer Science

Thiol-ene polymerisation: A promising technique to obtain novel biomaterials

Thiago O. Machado et al.

EUROPEAN POLYMER JOURNAL (2017)

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Review Chemistry, Multidisciplinary

Conversion of plant biomass to furan derivatives and sustainable access to the new generation of polymers, functional materials and fuels

Victor M. Chernyshev et al.

RUSSIAN CHEMICAL REVIEWS (2017)

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Article Biotechnology & Applied Microbiology

Production of biorenewable styrene: utilization of biomass-derived sugars and insights into toxicity

Jieni Lian et al.

JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY (2016)

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Synthesis of clickable amphiphilic polysaccharides as nanoscopic assemblies

Liye Fu et al.

CHEMICAL COMMUNICATIONS (2014)

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Review Green & Sustainable Science & Technology

A review on pyrolysis of biomass constituents: Mechanisms and composition of the products obtained from the conversion of cellulose, hemicelluloses and lignin

Francois-Xavier Collard et al.

RENEWABLE & SUSTAINABLE ENERGY REVIEWS (2014)

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Levoglucosan formation mechanisms during cellulose pyrolysis

Xiaolei Zhang et al.

JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS (2013)

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Mediating acid-catalyzed conversion of levoglucosan into platform chemicals with various solvents

Xun Hu et al.

GREEN CHEMISTRY (2012)

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JOURNAL OF ANALYTICAL AND APPLIED PYROLYSIS (2009)

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Highly deoxygenated sugars.: Part 3.: New derivatives of levoglucosan by tandem epoxide allyl alcohol rearrangement-cuprate cross-coupling

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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2005)

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