Environmentally conscious use of surfactant TPGS-750-M in water-based synthesis
In recent years, surfactant TPGS-750-M has emerged as a powerful tool for performing organic chemistry in aqueous media [1,2]. E.g., catalytic C-C bond formations such as the Sonogashira reaction can be performed in water under mild conditions [3]. Replacing an organic reaction solvent by water results in strongly reduced CO2 emission from waste incineration and is, therefore, highly desirable. In addition, the possibility to replace teratogenic solvents such as DMF, DMA or NMP by aqueous solutions of TPGS-750-M represents a major step towards safer chemical manufacturing [4].
So far, available TPGS-750-M data were mostly related to the synthetic use and were limited. The presentation will provide insight into biodegradability, hydrolytic stability and other properties of TPGS-750-M and their implications for the assessment of related process waste waters. The current status of reaction work-up options with data on the fate of the surfactant will be presented.
[1] B. H. Lipshutz, S. Ghorai, Aldrichimica Acta, 2008, 41, 59-72.
[2] M. Cortes-Clerget, N. Akporji, J. Zhou, F. Gao, P. Guo, M. Parmentier, F. Gallou, J.-Y. Berthon, B. H. Lipshutz, Nature Comm., 2019,10, 2169.
[3] M. Jakobi, F. Gallou, C. Sparr, M. Parmentier, Helv. Chim. Acta, 2019, e1900024.
[4] N. A. Isley, R. T. H. Linstadt, S. M. Kelley, F. Gallou, B. H. Lipshutz, Org. Lett., 2015, 17, 4734-4737.