Synteza, właściwości i zastosowanie 3-podstawionych pochodnych pentano-2,4-dionu
Loading...
Date
2011-04-13T10:53:30Z
Authors
Advisor
Editor
Journal Title
Journal ISSN
Volume Title
Publisher
Title alternative
Synthesis, properties and applications of 3-substituted derivatives of pentane-2,4-dione
Abstract
W niniejszej pracy doktorskiej przedstawiono metodę syntezy 3-podstawionych pochodnych pentano-2,4-dionu w mieszaninie rozpuszczalników organicznych, a także w środowisku wodnym. Zoptymalizowana metoda została następnie wykorzystana do syntezy szeregu pochodnych β-diketonów z różnymi podstawnikami w grupie metylenowej. Opracowana została też metoda izolacji i oczyszczania otrzymywanych produktów przy pomocy kompleksów z miedzią(II). Pozwoliło to na ich uzyskiwanie z bardzo wysoką czystością. Otrzymane produkty zostały zidentyfikowane oraz scharakteryzowane za pomocą metod spektroskopowych, co pozwoliło na określenie takich właściwości jak tautomeria keto-enolowa, czy stałe kompleksowania. W kolejnym etapie pracy otrzymane pochodne z podstawnikami nienasyconymi zostały wykorzystane w procesach polimeryzacji (kopolimeryzacja ze styrenem). Uzyskane polimery zostały przebadane pod kątem ich właściwości kompleksujących. W dalszej części przeprowadzono również eksperymenty dotyczące metatezy wybranych pochodnych pentano-2,4-dionu. Wykazano, że związki te mogą brać udział zarówno w homometatezie, jak i metatezie z innymi nienasyconymi związkami. Otrzymane pochodne znalazły również zastosowanie m.in. w analityce chemicznej do modyfikacji powierzchni krzemionki stosowanej w SPE oraz jako fazy stacjonarne w chromatografii gazowej.
In the submitted doctoral thesis a method for synthesis of pentane-2,4-dione 3-substituted derivatives is shown. The reactions were performed in a mixture of organic solvents as well as in aqueous environment. The optimized procedure was used for synthesis of several derivatives of β-diketones with various substituents in methylene group. Furthermore, a method for isolation and purification of obtained compounds as copper(II) complexes was proposed. It allowed for obtaining products of the reaction with high purity, Obtained products of the reaction were identified and characterized by means of spectroscopic methods. The properties of the examined compounds such as keto-enol tautomerism and complex stability constants were determined. In the next stage derivatives of pentane-2,4-dione with unsaturated substituents were used in polymerization (copolymerization with styrene). Complexing properties of the obtained polymers were examined. Several derivatives were also used in experiments involving metathesis. It has been shown that unstaurated derivatives of β-diketones can take part in homometathesis aand metathesis with other unsaturated compounds. Obtained derivatives were also used in chemical analysis -for modification of silica gel used in solid phase extraction and as stationary phases in gas chromatography.
In the submitted doctoral thesis a method for synthesis of pentane-2,4-dione 3-substituted derivatives is shown. The reactions were performed in a mixture of organic solvents as well as in aqueous environment. The optimized procedure was used for synthesis of several derivatives of β-diketones with various substituents in methylene group. Furthermore, a method for isolation and purification of obtained compounds as copper(II) complexes was proposed. It allowed for obtaining products of the reaction with high purity, Obtained products of the reaction were identified and characterized by means of spectroscopic methods. The properties of the examined compounds such as keto-enol tautomerism and complex stability constants were determined. In the next stage derivatives of pentane-2,4-dione with unsaturated substituents were used in polymerization (copolymerization with styrene). Complexing properties of the obtained polymers were examined. Several derivatives were also used in experiments involving metathesis. It has been shown that unstaurated derivatives of β-diketones can take part in homometathesis aand metathesis with other unsaturated compounds. Obtained derivatives were also used in chemical analysis -for modification of silica gel used in solid phase extraction and as stationary phases in gas chromatography.
Description
Wydział Chemii: Zakład Chemii Analitycznej
Sponsor
Keywords
β-diketony, β-diketones, Pentano-2, Pentane-2, 4-dion, 4-dione, Tautomeria, Tautomerism, Nienasycone podstawniki, Unsaturated substituents