Production of bis(?-ethoxy)terephthalate from terephthalic acid and ethylene oxide

Samsonova, T. I.; Mikhailov, G. D.; Malykh, V. A.; Chegolya, A. S.

doi:10.1007/bf00551183

Cited by 4 publications

(1 citation statement)

References 2 publications

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“…For this purpose, we made three suppositions based on the previous literature review [19]. First, epoxycarboxylic acid can react in the absence of a catalyst [20] (denoted by R i ); second, the reaction pathway proceeds via epoxy-amine zwitterion (denoted by Z i ), as proposed by Mares et al [21]; and third, the acid-amine complex transforms the epoxy into the final product [22] (denoted by R aa ). These pathways are illustrated in Schemes 4-6.…”

Section: Resultsmentioning

confidence: 99%

Theoretical and Experimental Insights of Benzimidazole Catalyzed by the Epoxy–Acrylic Acid Reaction

et al. 2022

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This study focuses on the experimental and molecular-level investigation of epoxy acrylate formation. Epoxy acrylate vinyl ester resin was prepared by a reaction of diglycidyl ether of bisphenol-A-based epoxy resin and acrylic acid, using benzimidazole as a catalyst. It was confirmed that benzimidazole can effectively catalyze this reaction. FTIR analysis of the product revealed a simple addition esterification reaction between the epoxide group and carboxylic group of acrylic acid excluding the side reactions (e.g., etherification). DFT computational studies were performed to theoretically explore the insights of reaction mechanisms. The calculations revealed that the benzimidazole-catalyzed reaction dominates the uncatalyzed reaction. A comparison of calculated activation energies showed that concerted mechanisms are less significant in such reactions owing to their high activation barriers.

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Section: Resultsmentioning

confidence: 99%

Theoretical and Experimental Insights of Benzimidazole Catalyzed by the Epoxy–Acrylic Acid Reaction

et al. 2022

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Model reactions of pyridinecarboxylic acids with glycidyl phenyl ether

Hsu¹,

Chen²

1990

Makromol. Chem.

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The reactions of 3-pyridinecarboxylic acid (nicotinic acid, NA) and Cpyridinecarboxylic acid (isonicotinic acid, ISNA) with 2,3-epoxypropyl phenyl ether (glycidyl phenyl ether, GPE) were studied by means of high performance liquid chromatography (HPLC). It is found that both reactions involve two-step mechanisms and have induction periods. 'Wo products, pyridinium salt and ester, are obtained in each study. The formation of pyridinium salt is the cause of the occurrence of the induction period. After the induction period, the kinetics of the reaction is second order. Pyridinium ions do not form complexes with carboxylate ions of pyridinecarboxylates but form activated complexes with the hydrogen-bonded complexes of pyridinecarboxylic acids and GPE to activate the esterification reactions. The mechanisms of the reactions are discussed in detail.there is no data in the literature on the reaction between N-containing model acids (e. g. PCA) and epoxide. The kinetics and mechanisms of the reaction between PCA and epoxide are quite different from those of the carboxyl-epoxide reaction which had been discussed previously lo-12, 15-22). Experimental partMaterials: GPE was dried over calcium hydride and distilled at reduced pressure. Anisole and 1-butanol were distilled and stored over molecular sieves. NA and ISNA were purified by recrystallization from a mixture of ethanol and diethyl ether. Instruments:Bruker AM-300WB FT-NMR or JEOL 100 MHz FT-NMR, JASCO FT/IR-3 and JEOL JMS-300 GC/MS were used to obtain NMR, IR and mass spectra.Kinetic euperiments: These were carried out under nitrogen in a thermostatted flask fitted with a constant speed stirrer, an inert gas inlet, a sampling device, a thermometer and a condenser. The reaction flask containing PCA (NA or ISNA) and solvent was heated to a desired temperature (100 0 1990, Htithig & Wepf Verlag, Basel CCC 0025-1 16X/90/$03.00

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Organic–inorganic hybrid materials based on the incorporation of nanoparticles of polysilicic acid (nPSA) with organic polymers

Hsu

Chang

Wang

2004

Materials Science and Engineering: A

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Production of bis(?-ethoxy)terephthalate from terephthalic acid and ethylene oxide

Cited by 4 publications

References 2 publications

Theoretical and Experimental Insights of Benzimidazole Catalyzed by the Epoxy–Acrylic Acid Reaction

Theoretical and Experimental Insights of Benzimidazole Catalyzed by the Epoxy–Acrylic Acid Reaction

Model reactions of pyridinecarboxylic acids with glycidyl phenyl ether

Organic–inorganic hybrid materials based on the incorporation of nanoparticles of polysilicic acid (nPSA) with organic polymers

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