363. Carbohydrate carbonates. Part II. Their preparation by ester-exchange methods

Hough, L.; Priddle, J.E.; Theobald, R. S.

doi:10.1039/jr9620001934

Cited by 25 publications

(11 citation statements)

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“…An overview on cyclic carbonate and NIPU syntheses including the use of glycerol and saccharide feedstocks was given by Blattmann and Mülhaupt . Sorbitol tricarbonate is known since the 1960s, but it has not yet been exploited as intermediate in NIPU synthesis . Most likely, this is attributed to difficulties encountered in the direct carbonatization of saccharides and its tedious purification .…”

Section: Introductionmentioning

confidence: 99%

“…Most likely, this is attributed to difficulties encountered in the direct carbonatization of saccharides and its tedious purification . Such synthetic problems are also well-known for the esterification of saccharides such as sorbitol, yielding complex reaction mixtures. − Moreover, unlike saccharide–glycidyl ether-based cyclic carbonates, which are viscous liquids and easy to handle in NIPU synthesis, the pure sorbitol tricarbonate is a crystalline solid, melts at high temperature of 230 °C close to its decomposition, has low solubility in nonpolar media, and is highly immiscible with most NIPU components. ,, …”

Section: Introductionmentioning

confidence: 99%

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Isocyanate-Free Route to Poly(carbohydrate–urethane) Thermosets and 100% Bio-Based Coatings Derived from Glycerol Feedstock

et al. 2016

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Glycerol serves as the exclusive bio feedstock for the preparation of high purity sorbitol tricarbonate (STC) as new intermediate for poly(carbohydrate−urethane) thermosets and 100% bio-based non-isocyanate polyhydroxyurethane (NIPU) coatings. In this process, glycerol-based acrolein is dimerized, carbonated, and oxidized, thus producing the highly reactive diepoxy functional ethylene carbonate (DOC), which by facile chemical CO 2 fixation yields high purity STC. Opposite to most state-of-the-art multifunctional five-membered cyclic carbonates and regardless of the feedstock used for its manufacture, STC enables amine curing at ambient temperature even in the absence of catalysts. According to FT-IR and NMR spectroscopic analyses of the amine/carbonate reaction kinetics, the internal cyclic carbonate group is 3 times more reactive with respect to the two terminal carbonate groups. This is attributed to the electronwithdrawing effect of terminal cyclic carbonates. Curing STC with a blend of bio-based flexible and rigid diamines such as dimer fatty acid-based diamine (Priamine 1074) and isophorone diamine affords poly(carbohydrate−urethane) thermosets and NIPU coatings exhibiting substantially improved thermal and mechanical properties.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Isocyanate-Free Route to Poly(carbohydrate–urethane) Thermosets and 100% Bio-Based Coatings Derived from Glycerol Feedstock

et al. 2016

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“…The S'-O-trityl derivative of inosine (I), required for attempted unambiguous synthesis of inosine 2',3'carbonate (III), was prepared by modifications of the published procedure (Bredereck, 1934)1 and was further characterized as its 2',3'-diacetate. With N, vV-dimethylformamide as solvent and sodium bicarbonate as catalyst, as described (Hough et al, 1962), treatment of 5'-O-tritylinosine (I) (Scheme I) with slightly more than 1 molar equiv of diphenyl carbonate at 130°afforded a Little product was obtained following this method; use of higher temperatures and more solvent, however, gave moderate yields of 5'-O-tritylinosine.…”

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confidence: 99%

Nucleotides. V. Purine Ribonucleoside 2',3'-Cyclic Carbonates. Preparation and Use for the Synthesis of 5'-Monosubstituted Nucleosides^*

Hampton¹,

Nichol²

1966

Biochemistry

117

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“…Monomersd isplaying more than two carbonate units that have been employed fort he synthesis of polymers in recent years are displayed in Figure 6. The preparation of sorbitol triscarbonate 6a is known from an early report by Hough et al [174] 6a can be obtained in moderate yields and enantiomerically pure form by as ingle-step reactiono fs orbitol with DPC in DMF at 110 8C. Despite these advances, 6a was not used for the preparationo fP HUs until ar ecent work by Mülhaupt and co-workers.…”

Section: Monomers With Multiple 5cc Moietiesmentioning

confidence: 99%

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

et al. 2019

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Given the large amount of anthropogenic CO2 emissions, it is advantageous to use CO2 as feedstock for the fabrication of everyday products, such as fuels and materials. An attractive way to use CO2 in the synthesis of polymers is by the formation of five‐membered cyclic organic carbonate monomers (5CCs). The sustainability of this synthetic approach is increased by using scaffolds prepared from renewable resources. Indeed, recent years have seen the rise of various types of carbonate syntheses and applications. 5CC monomers are often polymerized with diamines to yield polyhydroxyurethanes (PHU). Foams are developed from this type of polymers; moreover, the additional hydroxyl groups in PHU, absent in classical polyurethanes, lead to coatings with excellent adhesive properties. Furthermore, carbonate groups in polymers offer the possibility of post‐functionalization, such as curing reactions under mild conditions. Finally, the polarity of carbonate groups is remarkably high, so polymers with carbonates side‐chains can be used as polymer electrolytes in batteries or as conductive membranes. The target of this Review is to highlight the multiple opportunities offered by polymers prepared from and/or containing 5CCs. Firstly, the preparation of several classes of 5CCs is discussed with special focus on the sustainability of the synthetic routes. Thereafter, specific classes of polymers are discussed for which the use and/or presence of carbonate moieties is crucial to impart the targeted properties (foams, adhesives, polymers for energy applications, and other functional materials).

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363. Carbohydrate carbonates. Part II. Their preparation by ester-exchange methods

Cited by 25 publications

References 0 publications

Isocyanate-Free Route to Poly(carbohydrate–urethane) Thermosets and 100% Bio-Based Coatings Derived from Glycerol Feedstock

Isocyanate-Free Route to Poly(carbohydrate–urethane) Thermosets and 100% Bio-Based Coatings Derived from Glycerol Feedstock

Nucleotides. V. Purine Ribonucleoside 2',3'-Cyclic Carbonates. Preparation and Use for the Synthesis of 5'-Monosubstituted Nucleosides^*

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization

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363. Carbohydrate carbonates. Part II. Their preparation by ester-exchange methods

Cited by 25 publications

References 0 publications

Isocyanate-Free Route to Poly(carbohydrate–urethane) Thermosets and 100% Bio-Based Coatings Derived from Glycerol Feedstock

Isocyanate-Free Route to Poly(carbohydrate–urethane) Thermosets and 100% Bio-Based Coatings Derived from Glycerol Feedstock

Nucleotides. V. Purine Ribonucleoside 2',3'-Cyclic Carbonates. Preparation and Use for the Synthesis of 5'-Monosubstituted Nucleosides*

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO2 Utilization

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Product

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Nucleotides. V. Purine Ribonucleoside 2',3'-Cyclic Carbonates. Preparation and Use for the Synthesis of 5'-Monosubstituted Nucleosides^*

Polymers Based on Cyclic Carbonates as Trait d'Union Between Polymer Chemistry and Sustainable CO₂ Utilization