Lipase (Novozyme 435) catalyzed chemoselective one pot synthesis of surfactants

POLY 113

Tom Farrell1, Rahul Tyagi, Rahul_Tyagi@uml.edu2, Mukesh K. Pandey, mukesh_pandey@uml.edu2, Virinder S. Parmar3, and Arthur C. Watterson, Arthur_Watterson@uml.edu2. (1) Chemistry, Institute of Nano-Science and Engineering Technology, University of Massachusetts, Lowell, MA, USA, 26, lowell, MA 01854, (2) Institute for Nanoscience and Engineering Technology and Center for Advanced Materials, University of Massachusetts-Lowell, Lowell, MA 01854, (3) Bioorganic Laboratory, Department of Chemistry, University of Delhi, India, Delhi, Delhi 110007, India
Abstract: Chemoselectivity with the lipase Novozyme 435 in terms of selecting the amino group for over hydroxyl goups using an acylation reaction. There are many examples where such chemoselectivity is useful for synthetic transformations; our first example of the chemoselectivity was carried out with the serinol molecule. We have for sometime been interested in the synthesis of amphiphilic polymers and investigating their surfactant properties. Serinol is a useful compound in making surfactants due to its high polarization having three functional groups including two hydroxyls and one amino group. The chemo selective amidation of serinol with a long chain ester hydrocarbon using lipase (Novozyme 435) resulted in a free diol hydrophilic head with a long hydrophobic tail. Recent exploration with above enzyme has provided us a method to make such surfactants in a simple one pot experiment condition making them perfect substitutions for the more traditional methods of synthesis.

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General Papers: Functional Materials
6:00 PM-8:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Polymer Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007