Reduction ofindigo: Kinetics andmechanism

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1 Diss. ETB No Reduction ofindigo: Kinetics andmechanism A dissertation submitted to the Swiss Federal Institute oftechnology (ETH), Zurich for the degree of Doctor oftechnical Seiences presented by Xiunan JIN Master ofengineering, Tianjin Polytechnic University, China born on 19. May 1973 in China accepted on the recommendation of Prof. Dr. P. Rys, examiner Prof. Dr. M. Morbidelli, co-examiner Zurich,2003

2 Abstract This thesis has to be seen within the scope of a larger project which aims at replacing sodium dithionite currently used in the vat dyeing process by novel electrochemical techniques. In view ofthe potential future application ofthese techniques in the textile industry the following features were examined: the reduction of the leuco indigo at the cathode during the direct electrochemical reduction, the kinetics ofthe reaction between indigo and sodium dithionite, the mechanism and the kinetics of the formation of the intermediate indigo radical anion via the comproportionation reaction between indigo and the di-anionic form ofleuco indigo. The attempt to further reduce the di-anionic leuco indigo to indoxyl at the cathode failed, because the reduction potential employed was not sufficient. It was found that the decrease of the concentration of the di-anionic leuco indigo in the later course of the electrochemical reduction process, which as a hypothesis was postulated to be attributed to an over-reduction of the leuco indigo to indoxyl, was actuallycausedby the air oxygenpresent in the nitrogen gas. Both the reduction of indigo by sodium dithionite to di-anionic leuco indigo and the comproportionation reaction of indigo with the di-anionic

3 form ofthe leuco indigo forming the indigo radical anion were assumed to be homogeneous processes. The kinetics of these two reactions were studied, and it was found that their reaction rates both depend on the rate ofthe solution ofthe indigo particles and on the ratio ofthe rate ofthe re-crystallization process to the rate of the product formation. Thus, the effect of organic solvents, such as e.g. ethanol and dimethylsulfoxide on these rates, due to the higher solubility, were clearly demonstrated. The observed influence of such organic solvents and of oxygen on the EPR spectra ofthe indigo radical anion were attributed to solvent-solute or to paramagnetic interactions, respectively.

4 Zusammenfassung Die vorliegende Dissertation muss im Rahmen eines grösseren Forschungsvorhabens gesehen werden, welches darauf ausgerichtet ist, das zur Zeit immer noch vorwiegend in der Küpenfärberei angewandte Reduktionsmittel Natriumdithionit durch neuartige elektrochemische Technologien zu ersetzen. In Hinblick aufeine mögliche zukünftige Anwendung dieser Technologie in der Textilindustrie wurden hier die folgenden Aspekte genauer untersucht: Die Reduktion des Leukoindigos an der Kathode während der direkten elektrochemischen Reduktion; Die Kinetik der Reaktion zwischen Indigo und Natriumdithionit; Der Mechanismus und die Kinetik der Bildung des als Zwischenprodukt auftretenden Indigo-Radikalanions, das aus der Komproportionierungsreaktion zwischen dem Indigo und dem Dianion des Leukoindigos entsteht. Der Versuch, das Dianion des Leukoindigos an der Kathode weiter zum Indoxyl zu reduzieren misslang, weil das dabei angewandte Reduktionspotential nicht genügend gross war. Es wurde gefunden, dass die Abnahme der Konzentration des Dianions des Leukoindigos während dem späteren Verlauf des elektrochemischen Reduktionsprozesses, welche in einer Hypothese auf die Überreduktion des Leukoindigos zum Indoxyl

5 zurückgeführtwurde, in Wirklichkeit durch Spuren von Sauerstoffim Stickstoff-Schutzgas verursacht wurde. Sowohl die Reduktion des Indigos durch Natriumdithionit zum Dianion des Leukoindigos als auch die Komproportionierungsreaktion des Indigos mit dem Dianion des Leukoindigos, wodurch das Indigo-Radikalanion gebildet wird, wurden als homogene Prozesse postuliert. Die Kinetik dieser beiden Reaktionen wurde untersucht. Dabei stellte sich heraus, dass deren Reaktionsgeschwindigkeiten sowohl von der Geschwindigkeit der Auflösung der Indigoteilchen abhängt als auch vom Verhältnis der Geschwindigkeit, in welcher die gelösten Indigoteilchenwieder kristallisieren und der Geschwindigkeit der Produktebildung. So konnte der steigernde Einfluss von organischen Lösungsmitteln, wie z.b. Ethanol und Dimethylsulfoxid, auf diese Geschwindigkeit, zurückzuführen auf die bessere Löslichkeit der Indigoteilchen, klar gezeigt werden. Der beobachtete Einfluss solcher organischer Lösungsmittel sowie von Sauerstoff auf die ESR-Spektren des Indigo-Radikalanions wird auf Lösungsmitteleffekte beziehungsweise auf paramagnetische Wechselwirkungen zurückgeführt.

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