Industrial Biotransformations

Nitrilase
Acidovorax facilis
Fig. 3.5.5.1 – 2
3) Flow scheme
Not published.
4) Process parameters
conversion: 100 %
yield: 98.7 %
selectivity: 98 %
reactor type: consecutive stirred-batch
reactor volume: 500 L
space-time-yield: 1896 g · L –1
enzyme activity:
company:
3500 g product ·g –1
biocatalyst
Du Pont de Nemours and Co., USA
5) Product application
● Intermediate in the chemoenzymatic process for production of 1,5-dimethyl-2-piperidone (Xolvone),
which is a precision cleaning solvent.
● Xolvone is used in a variety of industrial applications, including electronics cleaning, photoresist
stripping, industrial degreasing, metal cleaning and resin cleanup; it can also be used in
the formulation of inks and industrial adhesives and as a reaction solvent for the production of
polymers and chemicals.
● Xolvone is not flammable, is completely miscible with water, has a good toxicological profile
and is readily biodegradable.
6) Literature
CN
2 = 4-cyanopentanonic acid ammonium salt
3 = 1,5-dimethyl-2-piperidone (Xolvone)
2
CO 2 - NH4 +
EC 3.5.5.1
● Hann, E.C., Sigmund, A.E., Hennessey, S.M., Gavagan, J.E., Short, D.R., Bassat, A.B., Chauhan,
S., Fallon, R.D., Payne, M.S., DiCosimo, R. (2002) Optimization of an immobilized-cell
biocatalyst for production of 4-cyanopentanoic acid, Org. Proc. Res. Dev. 6, 492–496
● Cooling, F.B., Fager, S.K., Fallon, R.D., Folson, P.W., Gallagher, F.G., Gavagan, J.E., Hann,
E.C., Herkes, F.E., Philips, R.J., Sigmund, A., Wagner, L.W., Wu, W., DiCosimo, R. (2001) Chemoenzymatic
production of 1,5-dimethyl-2-piperidone, J. Mol. Catal. B : Enzymatic 11,
295–306
428
CH 3NH 2
Pd/C
H 2
3
N
O