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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 and R DiCosimo |
| Institution: | 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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