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ERIC Number: EJ1003032
Record Type: Journal
Publication Date: 2012-Nov
Pages: 7
Abstractor: As Provided
Reference Count: 19
ISSN: ISSN-0021-9584
What Is Happening when the Blue Bottle Bleaches: An Investigation of the Methylene Blue-Catalyzed Air Oxidation of Glucose
Anderson, Laurens; Wittkopp, Stacy M.; Painter, Christopher J.; Liegel, Jessica J.; Schreiner, Rodney; Bell, Jerry A.; Shakhashiri, Bassam Z.
Journal of Chemical Education, v89 n11 p1425-1431 Nov 2012
An investigation of the Blue Bottle Experiment, a well-known lecture demonstration reaction involving the dye-catalyzed air oxidation of a reducing sugar in alkaline solution, has delineated the sequence of reactions leading to the bleaching of the dye, the regeneration of color, and so forth. Enolization of the sugar is proposed as a key step in the sequence. The first-order rate constant for this step was found to be approximately 2.3 x 10[superscript -3] min[superscript -1] with respect to total sugar concentration under the conditions used (0.184 M glucose, pH 13.3, 25 degrees C). Measurements with an oxygen-sensing electrode on Blue-Bottle mixtures containing varying quantities of methylene blue indicated that in a usual demonstration the rate of O[subscript 2] consumption is approximately 60% of the enolization rate. Small samples of the organic oxidation product were isolated and found by chromatographic and NMR-spectroscopic examination to consist primarily of the 5-carbon sugar acid arabinonic acid. (Contains 6 figures and 1 scheme.)
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Research
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A