Grosjean, Daniel and Salmon, Lynn G. and Cass, Glen R. (1992) Fading of Organic Artists' Colorants by Atmospheric Nitric Acid: Reaction Products and Mechanisms. Environmental Science and Technology, 26 (5). pp. 952-959. ISSN 0013-936X. doi:10.1021/es00029a013. https://resolver.caltech.edu/CaltechAUTHORS:20160629-110947535
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Abstract
The reaction products formed upon exposure of selected artists' colorants to gas-phase nitric acid have been identified using chemical ionization mass spectrometry. The two organic colorants that were most nitric acid-fugitive were triphenylmethane derivatives: the chloride cationic dye basic fuchsin yielded the corresponding nitrate salt, and the carbinol pararosaniline yielded the corresponding organic nitrate ester. Both also yielded small amounts of benzophenones. Other colorants studied yielded only small amounts of oxidation (but not nitration) products, i.e., phenols and/or ring-opening products: benzoic acid and hydroxyquinacridone from acridones, isatin and isatoic anhydride from indigo, trihydroxyanthraquinone from alizarin, and phthalic acid from Alizarin Crimson. The corresponding reaction mechanisms are outlined. The results are discussed in terms of possible damage to colorants in museum collections resulting from exposure to atmospheric nitric acid.
| Item Type: | Article | |||||||||
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| Additional Information: | © 1992 American Chemical Society. Received for review September 19, 1991. Revised manuscript received January 27, 1992. Accepted January 28, 1992. This work has been supported by a contract from The Getty Conservation Institute, Marina del Rey, CA. We thank Dr. Paul M. Whitmore for carrying out the high-concentration screening tests, and Dr. Dilip K. Sensharma for mass spectrometry analyses carried out at the Department of Chemistry, University of California, Los Angeles. At DGA, Mr. Eric Grosjean and Mr. Edwin L. Williams, II, carried out the liquid-phase tests with triphenylmethane colorants and Ms. Denise Yanez prepared the draft and final versions of the manuscript. | |||||||||
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| Issue or Number: | 5 | |||||||||
| DOI: | 10.1021/es00029a013 | |||||||||
| Record Number: | CaltechAUTHORS:20160629-110947535 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20160629-110947535 | |||||||||
| Official Citation: | Fading of organic artists' colorants by atmospheric nitric acid: reaction products and mechanisms Daniel Grosjean, Lynn G. Salmon, and Glen R. Cass Environmental Science & Technology 1992 26 (5), 952-959 DOI: 10.1021/es00029a013 | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 68742 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 29 Jun 2016 20:08 | |||||||||
| Last Modified: | 11 Nov 2021 04:04 |
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