https://doi.org/10.1007/s40090-020-00210-4

Potential bleach activators with improved imide hydrolytic stability

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  • Ziyuan Song1,
  • Xue Chen2,
  • Zhiyu Wang1,
  • Steve King2,
  • Haoyuan Yan3,
  • Kaimin Cai1,
  • Jianjun Cheng*1,
  1. Department of Materials Science and Engineering, University of Illinois At Urbana-Champaign, Urbana, IL, 61801, USA
  2. The Dow Chemical Company, Lake Jackson, TX, 77566, USA
  3. Department of Biochemistry, University of Illinois At Urbana-Champaign, Urbana, IL, 61801, USA

Published in Issue 2023-11-17

How to Cite

Song, Z., Chen, X., Wang, Z., King, S., Yan, H., Cai, K., & Cheng, J. (2023). Potential bleach activators with improved imide hydrolytic stability. International Journal of Industrial Chemistry, 11(3). https://doi.org/https://doi.org/10.1007/s40090-020-00210-4
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Abstract

The commercially available bleach activator, N,N,Nâ²,Nâ²-tetraacetylethylenediamine (TAED), has been widely used in laundry detergents to enable efficient low-temperature bleaching. However, the competitive hydrolysis of TAED limits its use in liquid detergents. Herein we report the synthesis of two TAED derivatives, N,N,Nâ²,Nâ²-tetracetylpropylene-1,2-diamine (TA(Me)ED) and N,N,Nâ²-triacetylpropylene-1,2-diamine (TriA(Me)ED), through the acetylation of propylene-1,2-diamine. The hydrolytic and perhydrolytic activity of the imide molecules were studied by HPLC to elucidate the structureâfunction relationship. Due to the increased steric hindrance imparted by the α-methyl group close to the imide, TA(Me)ED and TriA(Me)ED exhibited higher hydrolytic stability than TAED, with the hydrolytic rate constants (kH) at pH 8.0 decreased by 58% and 84% for TA(Me)ED and TriA(Me)ED, respectively. On the other hand, TA(Me)ED and TriA(Me)ED showed comparable perhydrolytic activity with TAED in the presence of peroxide, enabling similar bleaching effect of a model food dye at room temperature. These results suggest these TAED derivatives may have potential being used as improved bleach activators.

Keywords

  • Bleach activator,
  • Hydrolysis,
  • IMIDES,
  • Perhydrolysis,
  • Steric hindrance
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