Chiral Amino and Imino-Alcohols Based on (R)-Limonene

Fuscaldo, Rodrigo S.; Boeira, Eduam O.; Stieler, Rafael; Lüdtke, Diogo S.; Gregório, José Ribeiro

doi:10.21577/0103-5053.20190201

Cited by 2 publications

(3 citation statements)

References 28 publications

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“…The obtained values of modulus were slightly lower than those previously reported for a similar ETE formulation using a linear curing agent with two allyl-functionalized tertiary amine groups joined by six methylene units [ 43 ]. This can be attributed to the cycloaliphatic backbone of LCA that may hinder the network reticulation to a certain extent leading to a lower modulus than in the case of the linear curing agent [ 38 ].…”

Section: Resultsmentioning

confidence: 99%

“…For instance, several methods have been used to obtain dihydroxylated and diaminated limonene derivatives [ 34 ], halogenated limonene [ 35 , 36 ] and limonene functionalized with heterocycle moieties [ 37 ]. Fuscalfo et al described the synthesis of hydroxy-aromatic amines derived from limonene [ 38 ]. The epoxidation of limonene and further carbonylation, produced the polymerized carbonate to obtain the completely biobased poly (limonene carbonate) [ 39 ].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of a Curing Agent Derived from Limonene and the Study of Its Performance to Polymerize a Biobased Epoxy Resin Using the Epoxy/Thiol-Ene Photopolymerization Technique

et al. 2022

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This study describes the synthesis of a curing agent derived from limonene as well as its application to prepare biobased thermoset polymers via the epoxy/thiol-ene photopolymerization (ETE) method. A biobased commercial epoxy resin was used to synthesize a crosslinked polymeric matrix of polyether-polythioether type. The preparation of the curing agent required two steps. First, a diamine intermediate was prepared by means of a thiol-ene coupling reaction between limonene and cysteamine hydrochloride. Second, the primary amino groups of the intermediate compound were alkylated using allyl bromide. The obtained ditertiary amine-functionalized limonene compound was purified and characterized by FTIR and NMR spectroscopies along with GC-MS. The curing agent was formulated with a tetrafunctional thiol in stoichiometric ratio, and a photoinitiator at 1 mol % concentration, as the components of a thiol-ene system (TES). Two formulations were prepared in which molar concentrations of 30 and 40 mol % of the TES were added to the epoxy resin. The kinetics of the ETE photopolymerizations were determined by means of Real-Time FTIR spectroscopy, which demonstrated high reactivity by observing photopolymerization rates in the range of 1.50–2.25 s−1 for the epoxy, double bonds and thiol groups. The obtained polymers were analyzed by thermal and thermo-mechanical techniques finding glass transition temperatures (Tg) of 60 °C and 52 °C for the polymers derived from the formulations with 30 mol % and 40 mol % of TES, respectively. Potential applications for these materials can be foreseen in the area of coatings.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of a Curing Agent Derived from Limonene and the Study of Its Performance to Polymerize a Biobased Epoxy Resin Using the Epoxy/Thiol-Ene Photopolymerization Technique

et al. 2022

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“…The epoxides from R-(+)-limonene have even been precursors of several aminoalkylalcohols, where the nature of the substituents located in the amino group change (Figure 7) [34]. The compounds obtained are used as chiral auxiliaries for the addition of diethylzinc to benzaldehyde, yielding an enantiomeric excess between 78% and 85% for (R) -1-phenyl-1-propanol.…”

Section: Analysis and Discussionmentioning

confidence: 99%

R-(+)-limonene diastereoselective epoxidation: A minireview about of the synthesis methods

Rodríguez¹,

Lobo

2022

Cienc. En Desarro.

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R-(+)-limonene epoxidation has been focused from different synthesis methods. Thanks to the optically active epoxides obtained from this reaction are widely employed at industrial level, like: agrochemicals, polymers, cosmetics, pharmaceuticals. A key point found in this topic has been the asymmetric induction to improve the yield to the diastereomers of 1,2-limonene oxide. Many catalysts have been developed for the diastereoselective epoxidation, but some oxidation methodology have not been so useful. The enzymes and the Jacobsen´s catalyst presented the highest selectivity towards the endocyclic epoxides diastereomers, while other catalysts like metals supported on mesoporous materials were directed to one or more oxidation products, reducing their potential industrial scaling. Also, it was evidenced that controlling the reaction parameters it allows the segregation homogeneous catalyst to a phase different from the reaction products, thus increasing its useful reutilization in several reaction cycles. This minireview confronts the different systems used for the diastereoselective epoxidation of R-(+)-limonene. Challenges, issues and trends of said chemical transformation are also discussed.

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Chiral Amino and Imino-Alcohols Based on (R)-Limonene

Cited by 2 publications

References 28 publications

Synthesis of a Curing Agent Derived from Limonene and the Study of Its Performance to Polymerize a Biobased Epoxy Resin Using the Epoxy/Thiol-Ene Photopolymerization Technique

Synthesis of a Curing Agent Derived from Limonene and the Study of Its Performance to Polymerize a Biobased Epoxy Resin Using the Epoxy/Thiol-Ene Photopolymerization Technique

R-(+)-limonene diastereoselective epoxidation: A minireview about of the synthesis methods

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