Research Collection. Synthesis of aromatic aldehydes and the oscillatory behavior of their catalytic autoxidation. Doctoral Thesis.
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1 Research Collection Doctoral Thesis Synthesis of aromatic aldehydes and the oscillatory behavior of their catalytic autoxidation Author(s): Wang, Junkuan Publication Date: 1993 Permanent Link: Rights / License: In Copyright - Non-Commercial Use Permitted This page was generated automatically upon download from the ETH Zurich Research Collection. For more information please consult the Terms of use. ETH Library
2 cj WvS Diss. ETH No , Jrt-, 7. April 19% Synthesis of Aromatic Aldehydes and the Oscillatory Behavior of Their Catalytic Autoxidation A dissertation submitted to the SWISS FEDERAL INSTITUTE OF TECHNOLOGY ZURICH for the degree of Doctor of Technical Sciences presented by JunkuanWang Master of Science, Dalian University oftechnology born May 19,1962 citizen of China accepted on the recommendation of Prof. Dr. P. Rys, referee Prof. Dr. R. Prins, co-referee Zurich, 1993
3 VI Abstract In Part I of this work, the catalytic autoxidation of methyl-substituted aromatic compounds has been investigated to develop a process for the production of the corresponding aromatic aldehydes, particularly for the conversion ofp-cresol to p-hydroxybenzaldehyde. Under conventional autoxidation conditions, p-cresol cannot be oxidized directly because its phenolic hydroxy group exerts a potential inhibiting effect on the reaction involving free radicals. Therefore, p-cresol was acetylated first in acetic anhydride and then the resulting p- acetoxytoluene was autoxidized in the presence of cobaltdl) acetate and manganese(ii) bromide in a mixture of acetic acid and acetic anhydride. Such a process yielded only 20% ofthe aldehyde at a conversion of 50%. The corresponding carboxylic acid was formed as a main product. By the novel process developed in this work, the aldehyde formed during the oxidation was transformed immediately into benzylidene diacetate. This derivative can be readily hydrolyzed under mild conditions to afford the parent aldehyde. The effect of various process parameters such as the temperature and the concentration of the catalyst and of the trifluoroacetic acid on the yield of the benzylidene diacetate was studied with the aid of empirical models. Under optimal conditions p- acetoxybenzylidene diacetate was obtained in - about 70% yield at % substrate conversion. The results presented in this work demonstrate that the selectivity of the Co/Br'-catalyzed autoxidation for the corresponding aldehyde is higher than that of the Co-catalyzed autoxidation, particularly at high conversion. In addition, it has been found that the rate of the autoxidation of the benzaldehydes can be retarded by the competitive autoxidation of the corresponding methylbenzenes. Part II of this work presents a novel halogen-free chemical oscillator based on the catalytic autoxidation of benzaldehyde. This oscillatory system exhibits its periodicity not only in time but also in space: self-generated chemical waves propagating through the motionless reaction mixture have been observed. Furthermore, this oscillatory system reveals a considerable
4 VII kinetic hydrogen/deuterium isotope effect, which is particular fascinating and may provide a valuable tool for mechanistic studies and for testing mechanistic models. In Part III of this work, the oscillatory peroxidase-oxidase reaction has been investigated by using NADH deuterated at the nicotinamide 4-A position. The hydrogen/deuterium isotope effect on the oscillatory behavior has also been observed in this biochemical oscillator. In addition, a sequence of simple and aperiodic (chaotic) peroxidase-oxidase oscillations was found to occur between two stable steady states.
5 100%igem VIII Zusammenfassung In Teil I der vorliegenden Arbeit wurde die katalytische Autoxidation methyl-substituierter aromatischer Verbindungen mit dem Ziel untersucht, ein Verfahren fiir die Herstellung der entsprechenden aromatischen Aldehyde zu entwickeln. Die direkte Oxidation von p-kresol unter gewshnlichen Autoxidations- Bedingungen ist nicht moglich, da die phenolische Hydroxyl-Gruppe einen inhibierenden Einfluss auf diese radikalische Reaktion ausubt. Deshalb wurde p-kresol zuerst in Essigsaureanhydrid acetyliert und das daraus entstandene p-acetoxytoluol in Gegenwart von Kobalt(II)-acetat und Mangan(II)-bromid in einer Mischung aus Essigsfiure und Essigsaureanhydrid autoxidiert. Mit diesem Verfahren erhielt man bei einem Umsatz von 50% nur 20% des Aldehyds. Die entsprechende Karbonsaure wurde als Hauptprodukt gebildet. Im neuen, in dieser Arbeit entwickelten Verfahren, wird der durch die Oxidation entstandene Aldehyd in situ zum Benzyliden-diacetat umgewandelt. Dieses Derivat kann leicht und unter milden Bedingungen zum urspriinglichen Aldehyden hydrolysiert werden. Mit der Hilfe empirischer Modelle wurde der Einfluss verschiedener Parameter (Temperatur, Konzentration des Katalysators, Konzentration der Trifluoressigsaure) auf die Selektivitat des Benzyliden-diacetats untersucht. Unter optimalen Reaktionsbedingungen gelang es, p-acetoxybenzylidendiacetat bei 98 - Umsatz mit 70% Ausbeute herzustellen. Die in dieser Arbeit vorgestellten Resultate zeigen, dass die Selektivitat Kobalt-katalysierter Autoxidationen zugunsten der entsprechenden Aldehyde hflher ist, wenn dem System zusatzlich Bromid zugesetzt wird. Diese Aussage ist speziell bei hohen Umsatzen gultig. Zusatzlich wurde gefunden, dass die Geschwindigkeit der Autoxidation von Benzaldehyden durch die konkurrierende Autoxidation entsprechender Methylbenzole gedrosselt werden kann. In Teil II der vorliegenden Arbeit wird ein neuer, ohne Halogene arbeitender, chemischer Oszillator vorgestellt, welcher auf der katalytischen Autoxidation von Benzaldehyd basiert. Die beobachteten und
6 DC selbstgenerierten chemischen Wellen, welche sich durch die ruhende Reaktionsmischung bewegten, zeigen, dass das untersuchte oszillierende System Periodizitaten sowohl in der Zeit als auch in Raum aufweist. Die untersuchte oszillierende Reaktion weist zudem einen beachtlichen kinetischen Deuterium-Isotopeneffekt auf, welcher ein potentielles Mittel fur weitere mechanistische Studien darstellen konnte. Teil III dieser Arbeit befasste sich mit der oszillierenden Peroxidase- Oxidase-Reaktion. Dazu wurde NADH verwendet, welches in der Nikotinamid-4-A-Stellung deuteriert war. Auch in diesem biochemischen oszillierenden System konnte ein Deuterium-Isotopeneffekt im oszillierenden Verhalten beobachtet werden. Zudem konnte gezeigt werden, dass zwischen zwei stabilen stationaren Zustanden eine Reihe einfacher und aperiodischer (chaotischer) Peroxidase-Oxidase-Oszillationen ablaufen.
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