A study on the selective phosphorylation and phosphinylation of hydroxyphenols

Marosi, Gyoergy; Toldy, Andrea; Parlagh, Gyula; Nagy, Z.; Ludányi, Krisztina; Anna, P.; Keglevich, György

doi:10.1002/hc.10006

Cited by 16 publications

(3 citation statements)

References 12 publications

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“…Resorcinol and phloroglucinol were functionalized to form bio-based aromatic phosphorus-containing compounds (Scheme 22(B)). The biophenol has been partially 229 (Scheme 22(C)) and totally 230 (Scheme 22(D)) functionalized by using diethyl chlorophosphate in the presence of triethylamine in polar solvents and under relatively mild conditions.…”

Section: Used Phosphoric Acid and Obtained A Phosphorylated Lignin Withmentioning

confidence: 99%

Phosphorylation of bio-based compounds: the state of the art

et al. 2015

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International audienceOver the last few years, more and more papers have been devoted to phosphorus-containing polymers, mainly due to their fire resistance, excellent chelating and metal-adhesion properties. Nevertheless, sustainability, reduction of environmental impacts and green chemistry are increasingly guiding the development of the next generation of materials. The use of bio-based polymer matrices might allow the reduction of environmental impacts by using renewable carbon and by achieving more easily biodegradable or reusable materials. The aim of this review is to present both fundamental and applied research on the phosphorylation of renewable resources, through reactions on naturally occurring functions, and their use in biobased polymer chemistry and applications. In the first section, different strategies for the introduction of phosphorus-containing functions on organic backbones are described. In the following sections, the main families of chemicals based on renewable resources are covered: namely polysaccharides (cellulose, chitosan, starch, dextran etc.), biophenols (lignins, biobased phenolic compounds, cardanol etc.), triglycerides (oils, glycerol) and hydroxy acid compounds

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Section: Used Phosphoric Acid and Obtained A Phosphorylated Lignin Withmentioning

confidence: 99%

Phosphorylation of bio-based compounds: the state of the art

et al. 2015

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“…Chemical structures of the prepared compounds were determined by 31 P-NMR, 13 C-NMR (IG) and 1 H-NMR spectroscopy in a Bruker Avance 400 MHz spectrometer at room temperature in (CD 3 ) 2 CO solutions. External references were trimethylsilane (TMS) for 1 H-NMR and 13 C-NMR and phosphoric acid (H 3 PO 4 ) for 31 P-NMR.…”

Section: Characterizationsmentioning

confidence: 99%

“…Some studies found in the literature explored this way. Marosi et al [13] carried out the selective phosphorylation and phosphinylation of hydroquinone and phloroglucinol with diethyl chlorophosphate and diphenylphosphonyl chloride by a nucleophile substitution reaction (SN2). Ren et al [14] used the same reaction (SN2) to carry out the dimerization of catechol functionalizing the hydroxyl groups with the phenyl phosphonic dichloride to form a phosphorus-containing aromatic diphenol which is glycidylated to obtain a reactive phosphoruscontaining flame retardant.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of biobased phosphate flame retardants

Ménard¹,

Negrell-Guirao

Ferry

et al. 2014

Pure and Applied Chemistry

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An approach to prepare some biobased flame retardant (FR) compounds is presented. The adopted strategy consists in functionalizing an aromatic biobased phenolic compound, the phloroglucinol, with different phosphate groups in order to promote a charring effect. Different chlorophosphates were grafted onto phloroglucinol hydroxy groups and the functionalization of the hydroxy groups was quantitative. The synthesized biobased FR were incorporated into an epoxy matrix as additive to estimate their flame retardant properties. The influence of different parameters was studied such as the phosphorus content of the thermoset or the nature of the R group of the used phosphate P-O-R. MEB/EDX observations proved the influence of this R group on the compatibility between the FR and the matrix and its importance to obtain homogeneous thermoset. Thermogravimetric analyses of the phosphorus-containing thermosets showed a small decrease in thermal stability accompanied by a char yield almost tripled for a 3 % w P-containing thermoset compared to that of the thermoset without any FR. Pyrolysis combustion flow calorimetry was also used to evaluate the flammability of the modified epoxy thermoset. A significant decrease in peak of heat release rate and total heat released was observed compared to thermoset without FR. These results demonstrate the good flame retardant properties of these biobased phosphates in an epoxy matrix. In addition these results show the potential of the biobased phenolic compounds as raw material for flame retardants syntheses.

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