Ethoxyquin
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| Surname | Ethoxyquin | ||||||||||||||||||
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| Molecular formula | C 14 H 19 NO | ||||||||||||||||||
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| Molar mass | 217.31 g mol −1 | ||||||||||||||||||
| Physical state |
liquid |
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| density |
1.03 g cm −3 (20 ° C) |
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| boiling point |
decomposes above 150 ° C |
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| solubility |
practically insoluble in water (60 mg l −1 at 20 ° C) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | |||||||||||||||||||
Ethoxyquin (EQ) is a chemical compound from the quinoline group that is used as an antioxidant .
history
Ethoxyquin was discovered by Emil Knoevenagel in 1921 and brought to market in 1959 by the then chemical company Monsanto under the brand name Santoquin as an anti- aging agent for rubber. It has also been used to preserve animal feed since the 1960s .
Extraction and presentation
Ethoxyquin is obtained from p -chloronitrobenzene and sodium ethoxide . Their product is hydrogenated to p- phenetidine , which reacts with acetone to form ethoxyquin.
use
Ethoxyquin is an antioxidant, it prevents lipid peroxidation and delays the oxidation of lipophilic vitamins ( carotenes , xanthophylls , vitamin A and vitamin E ).
It is used extensively for the preservation of fish meal (especially feed for fish farms ). Before it was banned as a pesticide, ethoxyquin was also used as a post-harvest treatment to prevent skin tanning of apples.
Fish meal tends to self-ignite during transport. To prevent this, ethoxyquin is added to the fish meal in the country of origin. The International Maritime Organization (IMO) stipulates a content of at least 100 mg / kg during sea transport.
End 2016, the environmental organization published Greenpeace (eg. A study of 54 fish products salmon , trout , sea bream , sea bass ) for the presence of ethoxyquin. Ethoxyquin was detected in all 38 food fish from conventional aquaculture. In 32 samples from conventional farmed fish, the ethoxyquin exposure was over 50 µg / kg (ethoxyquin limit value for meat). The highest measured value of 881 µg / kg was found in a salmon product from Norwegian aquaculture (data in each case the sum of ethoxyquin and the degradation product ethoxyquin dimer). There is no limit value for ethoxyquin in fish in the EU. In 2017, the Geneva Cantonal Laboratory examined 18 samples of farmed salmon from Swiss shops for the consumer program “ A Bon Entendeur ” . In 15 ethoxyquines or their breakdown products were detected. In 2 high concentrations of over 1000 µg / kg were found. Only in one sample was no ethoxyquin detected.
Environmental behavior
The oxidative degradation product ethoxyquin dimer in particular accumulates in fish tissue; An accumulation in human adipose tissue and in breast milk has already been proven.
Admission
Ethoxyquin is approved in Germany as a feed additive (E 324). In organic farms in the EU and Switzerland, however, its use is prohibited.
It has not been approved as a plant protection product in the European Union since 2011 because it was not included in Annex I of Directive 91/414 / EEC. In Switzerland, too, no pesticides containing this active ingredient are permitted.
According to a press release from EFSA on November 18, 2015, no final safety assessment of the substance can take place due to a “general lack of data”. In the summer of 2017, the EU decided to ban the use of ethoxyquines if it cannot prove that the substances are safe for consumers. If the industry fails to provide this evidence, use will be prohibited from 2020. Until then, a replacement should be found that is both effective and safe.
Trade names
Santoquin , Stop-Scald
Web links
- Ethoxyquin: chemistry in edible fish. How banned pesticides end up in aquaculture , Greenpeace, December 2016, PDF file
- Edmund Maser: Expertise for Greenpeace eV on ethoxyquin
- Pesticide ethoxyquin in salmon , SWR market check from April 2, 2019
Individual evidence
- ↑ a b c data sheet Ethoxyquin from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
- ↑ a b c Entry on ethoxyquin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on June 17, 2014.
- ↑ Entry on ethoxyquin in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
- ↑ E. Knoevenagel: On the knowledge of the ketone anile, I .: Representation of aliphatic ketone aniles and alkaline cleavage of ketone anil iodine alkylates . In: Reports of the German Chemical Society (A and B Series) . tape 54 , no. 8 , September 17, 1921, pp. 1722–1730 , doi : 10.1002 / cber.19210540807 ( wiley.com [accessed June 6, 2019]).
- ↑ Janusz Skolimowski, Aleksandra Augustyniak, Alina Błaszczyk: Ethoxyquin: An Antioxidant Used in Animal Feed. 2013, accessed June 5, 2019 .
- ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 586 (English, preview ).
- ↑ Alina Błaszczyk, Aleksandra Augustyniak, Janusz Skolimowski: Ethoxyquin. An Antioxidant Used in Animal Feed . In: International Journal of Food Science . No. 585931 , 2013, p. 12 , doi : 10.1155 / 2013/585931 (English, PDF ).
- ^ Stabilizing Rendered Ingredients, Animal Feed and Pet Food
- ↑ Noble fish or disgust fish? - Salmon in factory farming ( Memento from December 21, 2016 in the Internet Archive ), manuscript for a Frontal21 broadcast from August 5, 2014
- ↑ Fishmeal , entry to CargoHandbook.com
- ↑ Gretel Bescoby (IFFO): Ethoxyquin in fishmeal - does it have a future?
- ↑ Ethoxyquin: Prohibited pesticides in edible fish. Retrieved January 7, 2020 .
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↑ Ethoxyquin: Chemistry in Edible Fish. How banned pesticides end up in aquacultures. , Greenpeace, December 16, 2016.
Overview of laboratory results - ↑ a b c Fish feed with pesticide: Ethoxyquin is still in almost all farmed salmon In: srf.ch, December 19, 2017, accessed on December 19, 2017.
- ↑ Victoria J. Berdikova Bohne, Anne-Katrine Lundebye, Kristin Hamre: Accumulation and depuration of the synthetic antioxidant ethoxyquin in the muscle of Atlantic salmon (Salmo salar L.) . In: Food and Chemical Toxicology . tape 46 , no. 5 , May 2008, pp. 1834 , doi : 10.1016 / j.fct.2008.01.028 (English).
- ^ Ethoxyquin - collaboration with ZDF. In: GALAB. August 24, 2015, accessed June 6, 2019 .
- ↑ bvl.bund.de: Has been taken off the market since DVO (EU) No .: 2017/962. Substances with an antioxidant effect
- ↑ Decision of the Commission of 3 March 2011 on the non-inclusion of ethoxyquin in Annex I of Council Directive 91/414 / EEC and amending Commission Decision 2008/941 / EC
- ^ Directorate-General for Health and Food Safety of the European Commission: Entry on ethoxyquin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 26, 2016.
- ↑ EFSA press release of November 18, 2015: Ethoxyquin: EFSA safety assessment without result