Acesulfame

from Wikipedia, the free encyclopedia
Structural formula
Structure of acesulfame-K
General
Surname Acesulfame
other names
  • Acesulfame-K
  • 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide
  • 6-methyl-1,2,3-oxathiazin-4 (3 H ) -one-2,2-dioxide
  • Potassium 6-methyl-2,2-dioxide-1,2,3-oxathiazin-4-olate
  • E  950
Molecular formula C 4 H 4 KNO 4 S.
Brief description

colorless, sweet-tasting solid

External identifiers / databases
CAS number 55589-62-3
EC number 259-715-3
ECHA InfoCard 100.054.269
PubChem 23683747
Wikidata Q132037
properties
Molar mass 201.24 g mol −1
Physical state

firmly

density

1.86 g / cm 3 (20 ° C)

Melting point

> 225 ° C (decomposition)

solubility

good in water (250 g l −1 at 20 ° C)

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Acesulfame-K is a synthetic, heat-resistant sweetener . In 1967, the chemist Karl Clauß accidentally discovered a sweet-tasting compound at Hoechst AG during the synthesis of oxathiazinone dioxides .

As a food additive , it is declared as E 950.

Molecular structure

Acesulfame belongs to the heterocycles because the molecule contains a six-membered ring with three heteroatoms (oxygen, sulfur and nitrogen) ( oxathiazine ring ).

properties

Acesulfame-K is a white solid that dissolves well in cold water and very easily in hot water . Water / ethanol mixtures are also suitable. Storage is unproblematic due to the high chemical stability. The sweetener is the potassium salt of acesulfame, acesulfame potassium or acesulfame-K with a sweetening power that is about 200 times that of sucrose .

Manufacturing

The production takes place in several steps, starting from the sodium salt of 4-chlorophenol :

Acesulfame synthesis.svg

The so-called SO 3 process has established itself as an industrial process compared to earlier variants with fluorosulfonyl isocyanate (FSO 2 NCO) or amidosulfofluoride (H 2 NSO 2 F) .

Industrial synthesis of acesulfame K

A salt of sulfamic acid, preferably a trialkylammonium salt, is reacted with diketene in methylene chloride to form acetoacetamide - N- sulfonate. The dissolved acetoacetamide- N- sulfonate is added to a solution of sulfur trioxide in methylene chloride, cyclization to an SO 3 adduct taking place. The SO 3 adduct is hydrolyzed with water to acesulfame-H, the so-called sweetener acid, and converted to the sweetener acesulfame-K with KOH. Gentle process and isolation conditions as well as the efficient processing of the liquid phases enable good yields (> 80%) and purities of over 99.5%.

Analytics

Acesulfame can be reliably detected in different matrices after adequate sample preparation by coupling chromatographic methods with mass spectrometry , such as B. the HPLC-MS .

use

Because of its heat resistance, acesulfame-K can also be used for cooking and baking. It tastes very similar to natural sugar, but has a slightly bitter taste in higher concentrations.

Acesulfame-K is used, for example, in drinks, usually in combination with other sweeteners such as aspartame . It's also found in toothpastes because it doesn't cause tooth decay .

Acesulfam-K has been approved in Germany since 1990 and is marketed under the brand name Sunett .

The permitted daily dose was from the scientific Committee on Food of the European Commission (Scientific Committee on Food, SCF) mg in adults at 9 per kilogram of body weight set.

Environmental relevance

Acesulfame-K is largely excreted unchanged by the body and is only partially broken down in sewage treatment plants . As a result, the substance reaches rivers and lakes in large quantities, where it can be detected ubiquitously. Concentrations in surface waters reach into the double-digit microgram-per-liter range. In research campaigns with a large number of target substances, acesulfame is often the substance with the highest measured concentrations. Acesulfame has even been detected in drinking water in Germany and some other countries. The Rhine near Basel carries over a whole year ago, more than 42 tons of the sweetener in the North Sea.

Web links

Individual evidence

  1. ↑ Entry on E 950: Acesulfame K in the European database on food additives, accessed on June 27, 2020.
  2. ↑ a b c Entry on acesulfame-K. In: Römpp Online . Georg Thieme Verlag, accessed on February 5, 2014.
  3. ↑ Entry on 6-methyl-1,2,3-oxathiazin-4 (3H) -one-2,2-dioxide in the GESTIS substance database of the IFA , accessed on April 5, 2020 (JavaScript required)
  4. ↑ a b Data sheet Acesulfame K from Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).
  5. ↑ Karl Clauss and Harald Jensen (1973): Oxathiazinondioxide, a new group of sweeteners. In: Angewandte Chemie . Vol. 85, No. 22, pp. 965-973. doi: 10.1002 / anie.19730852202 .
  6. ↑ Waszkiewicz-Robak, B. (Szkola Glowna Gospodarstwa Wiejskiego, Warszawa (Poland). Wydzial Zywienia Czlowieka), Swiderski, F .: Some functional properties of highly intensive sweeteners . In: Przemysl Spozywczy (Poland) . January 1, 2000 ( fao.org [accessed May 9, 2016]).
  7. ↑ Patent US6727359 : Composition comprising 6-methyl-3,4dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide, its salts, preparation thereof and uses therefor. Registered on July 26, 2002 , published on April 27, 2004 , Applicant: BDL, Inventor: Nianshou Tian, ​​Haiming Liu. ‌
  8. ↑ Karl Clauß, Harald Jensen: Oxathiazinondioxide, a new group of sweeteners . In: Angewandte Chemie . tape 85 , no. 22 , 1973, p. 965-973 , doi : 10.1002 / anie.19730852202 .
  9. ↑ Patent DE2453063 : Process for the production of acetoacetamide-n-sulfofluoride. Registered on November 8, 1974 , published on May 13, 1976 , applicant: Hoechst , inventor: Hartmut Pietsch, Karl Clauss, Harald Jensen, Erwin Schmidt. ‌
  10. ↑ Patent EP0218076B1 : Process for the production of the non-toxic salts of 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one-2,2-dioxide. Filed on Aug. 27, 1986 , published on January 3, 1990 , Applicant: Hoechst , inventors Dieter Reusch Ling, Adolf Linkies et al ..
  11. ↑ G. Roscher, H. Litterer et al., European Patent EP 638 076, published September 16, 1998.
  12. ↑ Waldemar Ens, Frank Senner, Benjamin Gygax, Götz Schlotterbeck: Development, validation, and application of a novel LC-MS / MS trace analysis method for the simultaneous quantification of seven iodinated X-ray contrast media and three artificial sweeteners in surface, ground , and drinking water . In: Analytical and Bioanalytical Chemistry . tape 406 , no. 12 , 2014, p. 2789-2798 , doi : 10.1007 / s00216-014-7712-0 , PMID 24590107 .
  13. ↑ Noora Perkola, Pirjo Sainio: Quantification of four artificial sweeteners in Finnish surface waters with isotope-dilution mass spectrometry . In: Environmental Pollution . tape 184 , 2014, p. 391–396 , doi : 10.1016 / j.envpol.2013.09.017 , PMID 24100049 .
  14. ↑ Register unavailable for registration number 1004466 (word mark "Sunett"), German trademark and patent office, as of Feb. 3, 2013.
  15. ^ Federal Institute for Risk Assessment : Evaluation of sweeteners and sugar substitutes. (PDF file) Background information No. 025/2014 of the BfR from July 1, 2014, accessed on November 30, 2015.
  16. ^ A b Sandro Castronovo, Arne Wick, Marco Scheurer, Karsten Nödler, Manoj Schulz, Thomas A. Ternes: Biodegradation of the artificial sweetener acesulfame in biological wastewater treatment and sandfilters. In: Water Research . 2016, doi : 10.1016 / j.watres.2016.11.041 .
  17. ↑ Deutschlandfunk , Forschung Aktuell, broadcast on September 22, 2011 Acesulfam: Unmolested by the toilet, sewer and sewage treatment plant .
  18. ↑ Robert Loos, Raquel Carvalho, Diana C. Antonio, Sara Comero, Giovanni Locoro, Simona Tavazzi, Bruno Paracchini, Michela Ghiani, Teresa Lettieri, Ludek Blaha, Barbora Jarosova, Stefan Voorspoels, Kelly Servaes, Peter Haglund, Jerker Fick, Richard H Lindberg, David Schwesig, Bernd M. Gawlik: "EU-wide monitoring survey on emerging polar organic contaminants in wastewater treatment plant effluents". In: Water Research. 2013. doi: 10.1016 / j.watres.2013.08.024 .
  19. ^ Andreas Fath: Rheines Wasser - 1231 kilometers with the current , Carl Hanser Verlag, Munich 2016, ISBN 978-3-446-44871-1 , pp. 135-142.
  20. ↑ Andri Bryner: Keeping rivers clean is provision for drinking water . In: eawag.ch , September 9, 2014, accessed on March 15, 2020.