Alternative solvents: from a compliance-driven activity to a trigger for innovation
During our evaluation of the potential of surfactant technology in collaboration with Professors Lipshutz and Handa,(1,2, 3) we have identified a variety of straightforward and highly advantageous transformationsand applied them successfully on-scale on various chemo and biocatalytic transformations.(4) Implementation of the technology typically results into significant benefits across our entire portfolio, not just from an environmental standpoint but also from an economic and productivity perspective. To name a few: reduction of organic solvent consumption, water use and cycle time, milder reaction conditions, improved yields and selectivities, which all contribute to improved process performance and lower manufacturing costs.(5)
These surfactant mediated reactions can be up-scaled in the already existing multi-purpose facilities of pharmaceutical or chemical organizations, using a catalytic amount of a combination of a non-ionic designer surfactant (e.g. TPGS-750-M, FI-750-M) in water, and a well-chosen organic co-solvent instead of traditional and undesirable organic solvents.(6) We now start gaining insight onto the physical phenomena involved and the role of the various components of the system and utilize this know-how to design even better catalytic systems.(7)
[1] See for example: Science2015, 349, 1087; Ang. Chem. Int. Ed. 2016, 55, 8979; Ang. Chem. Int. Ed. 2016, 55, 4914.
[2] J. Am. Chem. Soc. 2013, 135, 17707; Org. Lett. 2015, 17, 4734; Org. Lett. 2015, 17, 3968;Org. Proc. Res. Dev. 2016,20, 1104.
[3] Chem. Sci.2017, 8, 6354; ACS Catal. 2018, 7, 10, 7245; J. Org. Chem.2018, doi: 10.1021/acs.joc.7b03143.
[4] Green Chem. 2016, 18, 14. Nat. Rev. Chem.2018, 2, 306.Nature Comm. 2019, accepted, doi.org/10.1038/s41467-019-09751-4.
[5] ACS Sustain Chem. Eng. 2016, 4, 5838.
[6] Org. Proc. Res. Dev. 2016, 20, 1388.
[7] Org. Lett. 2017, 19, 194; Eur. J. Org. Chem.2018, 24, 6778.