Industrial Biotransformations

Lipase
Candida antarctica
1) Reaction conditions
[1]: 3.1 M, 800 g · L –1 [256.43 g · mol –1 ]
pH: 7.0
T: 60 °C
medium: 2-propanol
reaction type: carboxylic ester hydrolysis
catalyst: immobilized enzyme
enzyme: triacylglycerol acylhydrolase (triacylglycerol lipase, lipase)
strain: Candida antarctica
CAS (enzyme): [9001–62–1]
2) Remarks
O
OH
14
1 2
3
EC 3.1.1.3
1 = palmitic acid
2 = isopropanol
3 = isopropyl palmitate UNICHEMA Chemie BV
Fig. 3.1.1.3 – 1
+
OH E
● The problem during ester synthesis is the produced water, which leads to equilibrium conditions
meaning forward and backward reaction have the same rates.
● Two possible process layouts are published:
1) The reaction water is removed by azeotropic distillation (alcohol/water) at 0.26 bar. 2-Propanol
is continuously fed to the reactor (58 g · h –1 ) to replace the distilled one. The catalyst
can be easily removed by filtration.
2) Alternatively the reaction water is removed during esterification by pervaporation at only
80 °C. The reaction solution with the lower water level is cooled to 65 °C and passed to the
second reactor unit. After a second pervaporation step the water content is lowered to 0.2
wt.-%.
● The process can be adapted to other alcohols and acids. By the same process isopropyl myristate
is produced from myristic acid (H 3C-(CH 2) 12-COOH).
O
O
14
+ H2O
313