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Dialkyldimethylammonium prolinates

Didecyldimethylammonium L-prolinate and benzalkonium L-prolinate – ionic liquids containing an ammonium cation, giving them biocidal properties and an anion originating from L-proline amino acid. Biocidal activity of these compounds is comparable or greater than commonly used didecyldimethylammonium chloride and benzalkonium chloride. Their biocidal action is most effective against the following microorganisms: Micrococcus luteus, Staphylococcus epidermidis, Staphylococcus aureus, Moraxella catarhalis, Enterococcus faecium, Escherichia coli and two fungi: Candida albicans and Rhodotorula rubra.

Due to the high level of anti-microbial activity, obtained ionic liquids can be used in preparations in small concentration. They are probably low toxic to warm-blooded organisms, although appropriate tests have not been performed.

Dialkyldimethylammonium prolinates belong to the group of cationic surface active compounds. They display also electrostatic properties.

They can be constituents of:

  • biocidal preparations,
  • disinfecting/washing preparations.

They can also serve as catalysts in some types of reactions in asymmetric organic synthesis.


Benzalkonium prolinate


prolinian_benzalkoniowy








n = 9 60 %

n = 11 40 %



Didecyldimethylammonium prolinate


prolinian_didecylodimetyloamoniowy










They are thick, waxy compounds soluble in water, methanol, methylene chloride and acetone.


A brief description of the process

Dialkyldimethylammonium prolinates are obtained in a reaction between benzalkonium (didecyldimethylammonium) chloride and a potassium L-proline salt in aqueous environment at temperature 60 °C. The product is separated by vacuum distilling off water, dissolving in organic solvent, precipitating and filtering off by-product, i.e. potassium chloride and concentrating the ooze. Dialkyldimethylammonium L-prolinates require additional drying at elevated temperature and under reduced pressure.


Advantages of the technology offered

The technology is simple, low-waste and substrates are cheap. The environment of the reaction is water and the by-product is potassium chlorine.

The reaction yield is high.

The technology has been awarded with a silver medal at PALEXPO Exhibition (Geneva, 2010).


Equipment

The apparatus set comprises a glass reactor with bottom draining valve, equipped with a high-speed mechanical stirrer, a thermometer and a dephlegmator (which can be exchanged for a distillation set) and a heating-cooling jacket, allowing to heat up and cool down the contents. Auxiliary equipment comprises:

  • thermostat,
  • membrane vacuum pump,
  • vacuum evaporator (to distillate off water from the post-reaction mixture and for final drying of the product).


Advancement of proceedings

There has been compiled documentation concerning physicochemical properties and analytic methods have been developed. No acute toxicity studies have been performed.


Patents

Pat. PL 214 562 (2012) „New ionic liquids from the ammonium group, a method to obtain them and their application”.


Market competitiveness

New ionic liquids are novel compounds with fungicidal and bactericidal properties. Due to their big efficiency, obtaining the desired effect requires only small concentration of these compounds in preparations.


Type of expected cooperation

Cooperation in compiling registration documentation, deployment and launching production of the preparation.


Information

Anna Wiśniewska, M.Sc., Chem. Eng.

phone: + 48 22 568 21 93