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Ozone fading of natural organic colorants: mechanisms and products of the reaction of ozone with indigos

Grosjean, Daniel and Whltmore, Paul M. and Cass, Glen R. (1988) Ozone fading of natural organic colorants: mechanisms and products of the reaction of ozone with indigos. Environmental Science and Technology, 22 (3). pp. 292-298. ISSN 0013-936X. http://resolver.caltech.edu/CaltechAUTHORS:20140702-092152861

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Abstract

Indigo, dibromoindigo, and colorants containing thioindigo and tetrachlorothioindigo were exposed in the dark to dry, purified air containing ozone (10 ppm) for 4 days, and the exposed samples were analyzed by mass spectrometry. Under the conditions employed, indigo and dibromoindigo were entirely consumed, and the major reaction products were isatin and isatoic anhydride from indigo and bromoisatin and bromoisatoic anhydride from dibromoindigo. Thioindigo and its chloro derivative also reacted with ozone, though at a slower rate; the corresponding substituted isatins and anhydrides were tentatively identified as reaction products. These results can be rationalized in terms of a mechanism involving electrophilic addition of ozone onto the unsaturated carboncarbon bond. This mechanism adequately describes the observed loss of chromophore (fading) for all indigos studied and presumably applies to other indigo compounds as well. The reaction products of indigo, isatin and isatoic anhydride, were not ozone fugitive under our conditions.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/es00168a009 DOIArticle
http://pubs.acs.org/doi/abs/10.1021/es00168a009PublisherArticle
Additional Information:© 1988 by the American Chemical Society. Received for review January 28, 1987. Accepted September 17, 1987. This work was supported by a contract with The Getty Conservation Institute, Marina del Rey, CA.
Group:Environmental Quality Laboratory
Funders:
Funding AgencyGrant Number
Getty Conservation InstituteUNSPECIFIED
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Other Numbering System NameOther Numbering System ID
Environmental Quality LaboratoryA-218
Record Number:CaltechAUTHORS:20140702-092152861
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20140702-092152861
Official Citation:Ozone fading of natural organic colorants: mechanisms and products of the reaction of ozone with indigos Daniel. Grosjean, Paul M. Whitmore, Glen R. Cass, and James R. Druzik Environmental Science & Technology 1988 22 (3), 292-298
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:46621
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:02 Jul 2014 17:07
Last Modified:02 Jul 2014 17:07

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