Convenient Large-Scale Synthesis of <scp>d</scp>-Glucaro-1,4:6,3-dilactone

Gehret, Troy C.; Frobese, A. Stephen; Zerbe, James S.; Chenault, H. Keith

doi:10.1021/jo9015985

Cited by 12 publications

(13 citation statements)

References 48 publications

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“…The crosslinkers used (Fig. 1) were commercially available diethyl L ‐tartrate (DET), D ‐Glucaro‐1,4:6,3‐dilactone (GDL),44 and N , N′ ‐bis(methoxycarbonylmethyl)‐ D ‐glucaramide ( 4 ). Compound 4 was synthesized by treating GDL in methanol with two equivalents of methyl glycinate (Fig.…”

Section: Resultsmentioning

confidence: 99%

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Antimicrobial hydrogels formed by crosslinking polyallylamine with aldaric acid derivatives

Andrews

Figuly

Chapman

et al. 2010

J of Applied Polymer Sci

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Aqueous dispersions (0.1 wt %) of hydrogels 1 and 5-formed by crosslinking polyallylamine hydrochloride (MW 60,000) with aldaric acid derivatives, diethyl L-tartrate and N,N 0 -bis(methoxycarbonylmethyl)-D-glucaramide, respectively-exhibited complete (log 5) kill within 4 h of Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Candida albicans suspended in culture medium. This antimicrobial activity was much higher than that of uncrosslinked polyallylamine (1 wt % killed only 75% of E. coli in 24 h). When dispersed at 10 and 100 ppm, hydrogel 5 displayed complete (log 5) kill of E. coli within 30-60 and 15 min, respectively. Hydrogels 1 and 5 were active against S. aureus and Salmonella choleraesuis dried on hard stainless steel surfaces and accelerated the deaths of E. coli, P. aeruginosa, S. aureus, and C. albicans in a model skin cream formulation. A 0.8% aqueous dispersion of hydrogel 5 was also effective as a hand sanitizer, killing 99.7% of Serratia marcescens on human hands within 5 min. Hydrogels 1 and 5 caused no dermal irritation or allergic contact sensitization under the conditions of a human repeat insult patch test.

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Section: Resultsmentioning

confidence: 99%

“…Other chemicals were also used without further purification. D ‐Glucaro‐1,4:6,3‐dilactone (GDL) was synthesized as previously reported 44…”

Section: Methodsmentioning

confidence: 99%

Antimicrobial hydrogels formed by crosslinking polyallylamine with aldaric acid derivatives

Andrews

Figuly

Chapman

et al. 2010

J of Applied Polymer Sci

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“…The water resistance of the panels increased dramatically with increasing amounts of poly(glucaramide) in the panels. 317 Another route of producing hydroxylated PAs is ringopening polyaddition of glucaric acid derived glucarodilactone 318 (Figure 2f) with several alkylenediamines. Hashimoto et al synthesized various hydroxylated PAs through this route even at room temperature and with no catalyst.…”

Section: Glucaric Acid Platform Based Polymersmentioning

confidence: 99%

Lignocellulosic biomass: a sustainable platform for the production of bio-based chemicals and polymers

2015

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The demand for petroleum dependent chemicals and materials has been increasing despite the dwindling of their fossil resources. As the dead-end of petroleum based industry has started to appear, today's modern society has to implement alternative energy and valuable chemical resources immediately. Owing to the importance of lignocellulosic biomass for being the most abundant and bio-renewable biomass on earth, this critical review provides insights into the potential of lignocellulosic biomass as an alternative platform to fossil resources. In this context, over 200 value-added compounds, which can be derived from lignocellulosic biomass by using various treatment methods, are presented with their references. Lignocellulosic biomass based polymers and their commercial importance are also reported mainly in the frame of these compounds. The review article aims to draw the map of lignocellulosic biomass derived chemicals and their synthetic polymers, and to reveal the scope of this map in today's modern chemical and polymer industry.

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“…However, isosorbide contains cyclic ether functionalities, whereas GDL contains cyclic ester groups. While isosorbide is a commercially available monomer with applications including heat-resistant packaging and optical materials, GDL has been underutilized, despite having the potential for mass production and degradation in basic media . Isosorbide and GDL contain hydroxyl groups that can react with 10-undecenoic acid, a castor oil derivative to yield isosorbide undecenoate (IU) and glucarodilactone undecenoate (GDLU; Figure a). − The allyl groups in IU and GDLU can undergo thiol–ene photopolymerization with tetrathiols, such as pentaerythritol tetrakis(3-mercaptopropionate) (PETT), to form IU–PETT and GDLU–PETT thermosets. − …”

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confidence: 99%

Structural Basis for the Different Mechanical Behaviors of Two Chemically Analogous, Carbohydrate-Derived Thermosets

et al. 2021

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Two renewable, structurally analogous monomers, isosorbide undecenoate (IU) and glucarodilactone undecenoate (GDLU) reacted with pentaerythritol tetrakis(3-mercaptopropionate) (PETT) via thiol−ene photopolymerization to form IU− PETT and GDLU−PETT thermosets. Despite their chemical similarity, uniaxial tensile testing showed that GDLU−PETT exhibited a strain-hardening behavior and is significantly tougher than IU−PETT. To understand this observation, in situ tensile testing and wide-angle X-ray scattering experiments (WAXS) were conducted. While the 2D WAXS patterns of IU−PETT displayed an isotropic halo during uniaxial deformation, they exhibited a change from an isotropic halo to a pair of scattering arcs for the GDLU− PETT samples. Density functional theory calculations further revealed that the GDLU alkyl chains are less angled than the IU alkyl chains. Based on these results, we postulate that the GDLU molecules can more easily order and align during uniaxial deformation, hence increasing intermolecular interactions between the GDLU molecules and contributing to the observed strain hardening behavior of their thermosets. This study exemplifies how molecules with subtle differences in their chemical structures can alter the structures and thermophysical properties of the resulting polymers in unpredictable ways.

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Convenient Large-Scale Synthesis of d-Glucaro-1,4:6,3-dilactone

Abstract: Calcium D-glucarate was converted into D-glucaro-1,4:6,3-dilactone on 32-g, 1-kg, and 22-kg scale, using azeotropic distillation with methyl isobutyl ketone to drive the dehydration. The crystalline product was > or = 99.5% pure by GC and NMR, and overall yield was as high as 72%.

Cited by 12 publications

References 48 publications

Antimicrobial hydrogels formed by crosslinking polyallylamine with aldaric acid derivatives

Antimicrobial hydrogels formed by crosslinking polyallylamine with aldaric acid derivatives

Lignocellulosic biomass: a sustainable platform for the production of bio-based chemicals and polymers

Structural Basis for the Different Mechanical Behaviors of Two Chemically Analogous, Carbohydrate-Derived Thermosets

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