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Chemoenzymatic production of 1,5-dimethyl-2-piperidone |
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| Authors: | F. B. Cooling S. K. Fager R. D. Fallon P. W. Folsom F. G. Gallagher J. E. Gavagan E. C. Hann F. E. Herkes R. L. Phillips A. Sigmund L. W. Wagner W. Wu R. DiCosimo |
| Affiliation: | a Central Research and Development Department, E.I. du Pont de Nemours & Co., Experimental Station, P.O. Box 80328, Wilmington, DE 19880-0328, USA b DuPont Nylon Intermediates and Specialties, E.I. du Pont de Nemours & Co., Experimental Station, P.O. Box 80302, Wilmington, DE 19880-0302, USA |
| Abstract: | A chemoenzymatic process for the preparation of 1,5-dimethyl-2-piperidone (1,5-DMPD) from 2-methylglutaronitrile (MGN) has been demonstrated. MGN was first hydrolyzed to 4-cyanopentanoic acid (4-CPA) ammonium salt using the nitrilase activity of immobilized Acidovorax facilis 72W cells. The hydrolysis reaction produced 4-CPA ammonium salt with greater than 98% regioselectivity at 100% conversion, and at concentrations of 170–210 g 4-CPA/l. Catalyst productivities of at least 1000 g 4-CPA/g dry cell weight (dcw) of immobilized cells were achieved by recycling the immobilized-cell catalyst in consecutive stirred-batch reactions. After recovery of the immobilized cell catalyst for reuse, the 4-CPA ammonium salt in the aqueous product mixture was directly converted to 1,5-DMPD by low-pressure catalytic hydrogenation in the presence of added methylamine. |
| Keywords: | Nitrilase Nitrile hydratase Acidovorax facilis Immobilization 1,5-Dimethyl-2-piperidone |
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