Rhodamine B

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Structural formula
Rhodamine B.svg
General
Surname Rhodamine B
other names
  • (9- (2-carboxyphenyl) -3,6-bis (diethylamino) xanthylium chloride)
  • CI Basic Violet 10
  • CI 45170
Molecular formula C 28 H 31 ClN 2 O 3
Brief description

Greenish, odorless powder, red to purple when dissolved in water

External identifiers / databases
CAS number 81-88-9
EC number 201-383-9
ECHA InfoCard 100.001.259
PubChem 6694
ChemSpider 6439
Wikidata Q429022
properties
Molar mass 479.02 g mol −1
Physical state

firmly

density

1.31 g cm −3 (20 ° C)

Melting point

199-201 ° C

boiling point

> 245 ° C (decomposition)

solubility
  • slightly soluble in water: 15 g l −1 (20 ° C)
  • soluble in ethanol and benzene
safety instructions
GHS labeling of hazardous substances
05 - Corrosive

danger

H and P phrases H: 318-412
P: 260-273-280-305 + 351 + 338
Toxicological data

887 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Rhodamine B is a xanthene dye from the group of rhodamines .

history

aqueous rhodamine B solution

The class of rhodamines has been known since at least the 19th century. Rhodamine B is said to have been synthesized for the first time in 1905. It is closely related to rhodamine 6G, a laser dye , and rhodamine WT (water-tracer), from which it differs only in one carboxy group .

presentation

Rhodamine B is formed by heating 2 moles of 3-diethylaminophenol with one mole of phthalic anhydride with the addition of sulfuric acid and hydrochloric acid.

Synthesis of Rhodamine B

properties

Luminescence of an aqueous rhodamine B solution

The absorption maximum of rhodamine B is between 542 and 554 nm. The luminescence spectrum of a solution depends on factors such as the solvent, the pH value and, in particular, the temperature. The luminescence of a neutral, aqueous solution has its maximum at around 600 nm.

use

Rhodamine B is used for auramine-rhodamine staining in the laboratory, for staining experiments in nature and as a non-specific fluorescent marker. Rhodamine B solutions are used to demonstrate two-photon photoacoustics .

Rhodamine was and is used in many countries as a food coloring, for cosmetics, as a textile coloring and as a water tracer. This is not done in Europe and the USA, as rhodamine B is classified as potentially carcinogenic , mutagenic and ecotoxic . It is still used as a textile dye and now and then appears as a food dye in sweets or shrimp.

Individual evidence

  1. ↑ a b c data sheet Rhodamine B (PDF) from Carl Roth , accessed on April 19, 2013.
  2. ↑ a b data sheet Rhodamine B from Sigma-Aldrich , accessed on April 19, 2013 ( PDF ).
  3. ↑ a b c d Entry on rhodamine B in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
  4. ^ A b S. D. Gangolli: The Dictionary of Substances and their Effects (DOSE) OS . Royal Society of Chemistry, 1999, ISBN 978-0-85404-833-5 , pp. 688 .
  5. ^ E. Noelting, K. Dziewonski: On the knowledge of the rhodamines . In: Reports of the German Chemical Society . tape 38 , 1905, pp. 3516-3527 , doi : 10.1002 / cber.190503803186 .
  6. ↑ T. Nedelcev, D. Racko, I. Krupa: Preparation and characterization of a new derivative of Rhodamine B with an alkoxysilane moiety . In: Dyes and Pigments . tape 76 , 2008, p. 550-556 , doi : 10.1016 / j.dyepig.2006.11.002 .
  7. ^ A. Willmes: Taschenbuch Chemical Substances , 3rd edition, Verlag Harri Deutsch, 2007, ISBN 978-3-8171-1787-1 , p. 972.
  8. ↑ T. Karstens, K. Kobs: Rhodamine B and Rhodamine 101 as Reference Substances for Fluorescence Quantum Yield Measurements . In: The Journal of Physical Chemistry . Vol. 84, No. 14 , 1980, pp. 1871–1872 , doi : 10.1021 / j100451a030 (English).
  9. ^ Y. Yamaoka, M. Nambu, T. Takamatsu: Fine depth resolution of two-photon absorption-induced photoacoustic microscopy using low-frequency bandpass filtering . In: Optics Express . tape 19 , 2011, p. 13365 , doi : 10.1364 / OE.19.013365 , PMID 21747492 .
  10. ↑ G. Langer, K.-D. Bouchal, H. Grün, P. Burgholzer, T. Berer: Two-photon absorption-induced photoacoustic imaging of Rhodamine B dyed polyethylene spheres using a femtosecond laser . In: Optics Express . tape 21 , 2013, p. 22410 , doi : 10.1364 / OE.21.022410 , PMID 24104130 .
  11. ^ H. Lee, SH Park, YK Park, BH Kim, SJ Kim, SC Jung: Rapid destruction of the rhodamine B using TiO2 photocatalyst in the liquid phase plasma. In: Chemistry Central Journal . Volume 7, number 1, 2013, p. 156, doi: 10.1186 / 1752-153X-7-156 , PMID 24041151 , PMC 3847586 (free full text).
  12. ↑ M. Soylak, YE Unsal, E. Yilmaz, M. Tuzen: Determination of rhodamine B in soft drink, wastewater and lipstick samples after solid phase extraction. In: Food and chemical toxicology: an international journal published for the British Industrial Biological Research Association. Volume 49, number 8, August 2011, pp. 1796–1799, doi: 10.1016 / j.fct.2011.04.030 . PMID 21570440 .
  13. ↑ T. Kaji, T. Kawashima, M. Sakamoto, Y. Kurashige, F. Koizumi: Inhibitory effect of rhodamine B on the proliferation of human lip fibroblasts in culture. In: Toxicology . Volume 68, Number 1, 1991, pp. 11-20, doi: 10.1016 / 0300-483X (91) 90058-9 ; PMID 1871776 .
  14. ^ A. Kranjc (Ed.): Tracer Hydrology 97: Proceedings of the 7th International Symposium on Water Tracing . AA Balkema Publishers, Rotterdam 1997, ISBN 978-90-5410-875-7 , pp. 71–75 ( limited preview in Google Book search).
  15. ↑ P. Brandt: Reports on food safety. Federal Office for Consumer Protection and Food Safety 2005, p. 8.
  16. ^ Q. Wang, J. Li, Y. Bai, X. Lu, Y. Ding, S. Yin, H. Huang, H. Ma, F. Wang, B. Su: Photodegradation of textile dye Rhodamine B over a novel biopolymer-metal complex wool-Pd / CdS photocatalysts under visible light irradiation. In: Journal of Photochemistry and Photobiology . B, Biology. Volume 126, September 2013, pp. 47-54, doi: 10.1016 / j.jphotobiol.2013.07.007 , PMID 23895864 .
  17. ^ The Daily Mail: Illegal and potentially carcinogenic food dyes normally used by the sewage industry discovered in children's sweets , February 17, 2014.
  18. ^ Chemistry World: Toxic industry dyes found in Indian sweets , April 3, 2013.
  19. ↑ Food Safety Net: Coloring in belacan can cause cancer , August 13, 2010.
  20. ↑ ABS-CBN News: Industrial dye found in food in Cebu - FDA , October 22, 2013.

Web links

Commons : Rhodamine B  - Collection of Pictures, Videos and Audio Files