Reaction of limonene dioxide with ethanol

Mukhamedova, L. A.; Kudryavtseva, M. I.; Мартынов, А. А.

doi:10.1007/bf00924690

Cited by 4 publications

(3 citation statements)

References 1 publication

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“…In case of LDO an endothermic signal was observed with T max at 187°C (T onset = 142.3°C; ΔH N = 50.5 kJ•mol -1 ) indicating the boiling point (Figure 2). In a second step, the polymerization behavior of the monomers was studied with DSC in presence of boron trifluoride ethylamine complex as a Lewis acid catalyst which is known to activate the catalytic ringopening polymerization of epoxide monomers, as well as the addition of nucleophiles as ethanol to LDO [15][16][17]. DSC thermograms of the three monomers BADGE, ECC and LDO in presence of 10 mol% of BF 3 •NH 2 Et are depicted in Figure 3 and summarized in Table 1.…”

Section: Catalyzed Ring-opening Polymerizationmentioning

confidence: 99%

Diastereoisomeric diversity dictates reactivity of epoxy groups in limonene dioxide polymerization

Soto¹,

Koschek²

2018

Express Polym. Lett.

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Limonene dioxide (LDO) has the potential to find a wide application as a bio-based epoxy resin. Its polymerizations by catalyzed ring-opening, and by polyaddition with diamines were compared with the polymerizations of the commercial epoxy resins bisphenol-A diglycidyl ether (BADGE), and 3,4-epoxycyclohexylmethyl-3′,4′-epoxycyclohexane carboxylate (ECC). Differential scanning calorimetry (DSC) studies showed that LDO polymerizations suffer in all cases studied from incomplete conversions. Nuclear magnetic resonance (NMR) studies revealed that in cis-isomers of LDO the internal epoxide rings were not reacting. The low reactivity of this epoxide group was explained by mechanistic considerations making use of the Fürst-Plattner rule, or trans-diaxial effect. Due to diastereomeric diversity approximately one-fourth of epoxide groups present in LDO could not react. Therefore, a diastereoselective epoxidation of limonene could provide a fully reactive bio-based epoxy resin.

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Section: Catalyzed Ring-opening Polymerizationmentioning

confidence: 99%

Diastereoisomeric diversity dictates reactivity of epoxy groups in limonene dioxide polymerization

Soto¹,

Koschek²

2018

Express Polym. Lett.

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“…It has also been recently employed in the synthesis of cyclic limonene dicarbonate, a monomer for the production of linear and cross‐linked poly(hydroxy urethane)s. The reaction of this dicyclic carbonate with polyamines results in thermoset, non‐isocyanate oligo and polyurethanes (NIPUs) that exhibit promising properties . The cycloaliphatic oxirane (1,2‐epoxide) and 1,1‐disubstituted oxirane (8,9‐epoxide) moieties in LDO show a significant difference in their respective reactivity . Utilizing this disparity, we report in this work the chemoselective alternating copolymerization of LDO with CO 2 , yielding aliphatic polycarbonates with a high number of pendant epoxide groups, namely, poly(limonene‐8,9‐oxide carbonate) (PLOC).…”

Section: Figurementioning

confidence: 99%

Chemoselective Alternating Copolymerization of Limonene Dioxide and Carbon Dioxide: A New Highly Functional Aliphatic Epoxy Polycarbonate

Sablong

Koning

2016

Angew Chem Int Ed

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The alternating copolymerization of biorenewable limonene dioxide with carbon dioxide (CO2 ) catalyzed by a zinc β-diiminate complex is reported. The chemoselective reaction results in linear amorphous polycarbonates that carry pendent methyloxiranes and exhibit glass transition temperatures (Tg ) up to 135 °C. These polycarbonates can be efficiently modified by thiols or carboxylic acids in combination with lithium hydroxide or tetrabutylphosphonium bromide as catalysts, respectively, without destruction of the main chain. Moreover, polycarbonates bearing pendent cyclic carbonates can be quantitatively prepared by CO2 insertion catalyzed by lithium bromide.

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“…[9] The cycloaliphatic oxirane (1,2-epoxide) and 1,1-disubstituted oxirane (8,9-epoxide) moieties in LDO show a significant difference in their respective reactivity. [10] Utilizing this disparity, we report in this work the chemoselective alternating copolymerization of LDO with CO 2 , yielding aliphatic polycarbonates with a high number of pendant epoxide groups, namely, poly(limonene-8,9-oxide carbonate) (PLOC). To our best knowledge, this is the first report on the synthesis of such linear, non-gelling epoxide-functionalized PCs, at high monomer conversion using a diepoxide and CO 2 .…”

mentioning

confidence: 99%

Chemoselective Alternating Copolymerization of Limonene Dioxide and Carbon Dioxide: A New Highly Functional Aliphatic Epoxy Polycarbonate

Sablong

Koning

2016

Angewandte Chemie

View full text Add to dashboard Cite

The alternating copolymerization of biorenewable limonene dioxide with carbon dioxide (CO2) catalyzed by a zinc β‐diiminate complex is reported. The chemoselective reaction results in linear amorphous polycarbonates that carry pendent methyloxiranes and exhibit glass transition temperatures (Tg) up to 135 °C. These polycarbonates can be efficiently modified by thiols or carboxylic acids in combination with lithium hydroxide or tetrabutylphosphonium bromide as catalysts, respectively, without destruction of the main chain. Moreover, polycarbonates bearing pendent cyclic carbonates can be quantitatively prepared by CO2 insertion catalyzed by lithium bromide.

show abstract

Reaction of limonene dioxide with ethanol

Cited by 4 publications

References 1 publication

Diastereoisomeric diversity dictates reactivity of epoxy groups in limonene dioxide polymerization

Diastereoisomeric diversity dictates reactivity of epoxy groups in limonene dioxide polymerization

Chemoselective Alternating Copolymerization of Limonene Dioxide and Carbon Dioxide: A New Highly Functional Aliphatic Epoxy Polycarbonate

Chemoselective Alternating Copolymerization of Limonene Dioxide and Carbon Dioxide: A New Highly Functional Aliphatic Epoxy Polycarbonate

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