Study of the reaction between substituted phenols and formaldehyde

Šebenik, Anton; Lapanje, Savo

doi:10.1002/apmc.1977.050630109

Cited by 13 publications

(1 citation statement)

References 13 publications

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“…There is a large amount of literature on the general reactivity of aromatic compounds, especially correlation of reactivity with Hammett activity coefficients,5 localization energy,6 and frontier molecular orbitals 7. Many experimental kinetic studies have been conducted on the reactivity of phenolic compounds (especially phenol) with formaldehyde,8–20 but few systematic studies have been conducted that compare the reactivity of different phenolic compounds with formaldehyde, especially under the same reaction conditions.…”

Section: Resultsmentioning

confidence: 99%

Predicting the reactivity of phenolic compounds with formaldehyde under basic conditions: Anab initio study

Conner

2000

J. Appl. Polym. Sci.

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A method is needed to predict which compounds, from the many alternative phenolic compounds, might be best for making polymeric phenolic systems. Kinetic data for the reaction of a series of phenolic compounds with formaldehyde using a base catalysis are available in the literature. Semiempirical calculations, using RHF/PM3, and ab initio calculations, using RHF/6‐31G, RHF/6‐31+G, and B3LYP/6‐311+G(2d,p), were performed on the series of phenolic compounds to determine their relative reactivities. Atomic charges were determined for the phenolate anions. For each compound, I summed the absolute value of the calculated, negative charges residing on carbon atoms of the phenolic ring at which the HOMO was located and at which no substituent was present to cause steric interference with the reaction. The sum of the charges for each compound was then regressed against the log of the relative reaction rate for that compound. The sum of charges from PM3‐based calculations gave poor correlation with reactivity. The sums of charges calculated by the CHelpG and Merz–Kollman/Singh methods at the ab initio levels of theory give excellent correlations with reactivity of the phenolics toward formaldehyde. Based on the calculated charges, estimates of the relative reactivity at each of the reactive sites on each of the phenolic compounds were determined. © 2000 John Wiley & Sons, Inc. J Appl Polym Sci 78: 355–363, 2000

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Section: Resultsmentioning

confidence: 99%

Predicting the reactivity of phenolic compounds with formaldehyde under basic conditions: Anab initio study

Conner

2000

J. Appl. Polym. Sci.

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Study of the reaction between dimethyl phenols and formaldehyde in alkaline medium

Šebenik¹,

Lapanje²

1978

Angew. Makromol. Chem.

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The reaction of several dimethyl phenols with formaldehyde in alkaline medium was investigated. The addition products were separated by means of high pressure liquid chromatography and identified using IR and NMR spectroscopy. 2,3dimethyl phenol yields four, 2,4dirnethyl phenol one, 2,s-dimethyl phenol four, 2,6-dimethyl phenol one, 3,4-dimethyl phenol three, and 3,Sdimethyl phenol five addition products. 3.5-dimethyl phenol was the most reactive, 2,6-dimethyl and 2.4-dimethyl phenols the least reactive species. Rate constants for individual reactions were obtained from the dependence of concentrations on the reaction time. ZUSAM MENFASSUNG:Eine Reihe von Reaktionen zwischen den Dimethylphenolen und Formaldehyd im alkalischen Bereich wurden untersucht. Die Additionsprodukte wurden mittels Hochdruckfliissigkeitschromatographie getrennt und mittels IRund NMR-Spektroskopie identifiziert. 2.3-Dimethylphenol gibt vier, 2.4-Dimethylphenol ein, 2,5-Dimethylphenol vier, 2.6-Dimethylphenol ein, 3,CDimethylphenol drei und 3,5-Dimethylphenol fiinf Additionsprodukte. 3,s-Dimethylphenol ist am reaktivsten, 2,4-und 2,6-Dimethylphenol sind am wenigsten reaktiv. Die Geschwindigkeitskonstanten wurden aus der Abhangigkeit der Konzentration der Reaktionsprodukte von der Reaktionszeit ermittelt.

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Untersuchungen zur reaktion von o‐kresol mit formaldehyd unter verwendung tertiärer amine

Roatsch¹,

Reinisch²,

Hinzmann³

et al. 1994

Angew. Makromol. Chem.

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ZUSAMMENFASSUNG:Die Reaktion von o-Kresol mit Formaldehyd wurde unter Verwendung verschiedener tertiarer Amine als Katalysatoren untersucht. Der EinfluB der Reaktionsparameter Basizitat, Temperatur, Reaktionszeit und Formaldehydkonzentration wird diskutiert. Fur die bevorzugte Bildung von 2,4-Bis(hydroxymethyl)-6-methylphenol wurden optimierte Synthesebedingungen erarbeitet. Die Bildung von Zwei-bzw. Mehrkernprodukten konnte nicht ausgeschlossen werden. SUMMARY:The reaction between 0-cresol and formaldehyde was investigated using various tertiary amines as catalysts. The influence of the reaction parameters basicity, temperature, reaction time and concentration of formaldehyde was discussed. To yield preferentially 2,4-bis(hydroxymethyl)-6-methylphenol the conditions of synthesis were optimized. The formation of bi-and polynuclear products cannot be avoided.

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Study of the reaction between substituted phenols and formaldehyde

Cited by 13 publications

References 13 publications

Predicting the reactivity of phenolic compounds with formaldehyde under basic conditions: Anab initio study

Predicting the reactivity of phenolic compounds with formaldehyde under basic conditions: Anab initio study

Study of the reaction between dimethyl phenols and formaldehyde in alkaline medium

Untersuchungen zur reaktion von o‐kresol mit formaldehyd unter verwendung tertiärer amine

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