Biodegradable products by lipase biocatalysis.
The interest in the applications of biocatalysis in organic syntheses has rapidly increased. In this context, lipases have recently become one of the most studied groups of enzymes. We have demonstrated that lipases can be used as biocatalyst in the production of useful biodegradable compounds. A number of examples are given. 1-Butyl oleate was produced by direct esterification of butanol and oleic acid to decrease the viscosity of biodiesel in winter use. Enzymic alcoholysis of vegetable oils without additional organic solvent has been little investigated. We have shown that a mixture of 2-ethyl-1-hexyl esters can be obtained in a good yield by enzymic transesterification from rapeseed oil fatty acids for use as a solvent. Trimethylolpropane esters were also similarly synthesized as lubricants. Finally, the discovery that lipases can also catalyze ester syntheses and transesterification reactions in organic solvent systems has opened up the possibility of enzyme catalyzed production of biodegradable polyesters. In direct polyesterification of 1,4-butanediol and sebacic acid, polyesters with a mass average molar mass of the order of 56,000 g mol-1 or higher, and a maximum molar mass of about 130,000 g mol-1 were also obtained by using lipase as biocatalyst. Finally, we have demonstrated that also aromatic polyesters can be synthesized by lipase biocatalysis, a higher than 50,000 g mol-1 mass average molar mass of poly(1,6-hexanediyl isophthalate) as an example.
Linko
Y Y
YY
Department of Chemical Technology, Helsinki University of Technology, Finland. yu-yen.linko@hut.fi
Lämsä
M
M
Wu
X
X
Uosukainen
E
E
Seppälä
J
J
Linko
P
P
D001673:Biodegradation, Environmental; D001709:Biotechnology / Q000379:methods*; D005227:Fatty Acids / Q000737:chemistry* / Q000378:metabolism; D005229:Fatty Acids, Monounsaturated; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D009829:Oleic Acids / Q000138:chemical synthesis* / Q000378:metabolism; D010938:Plant Oils / Q000737:chemistry; D011091:Polyesters / Q000138:chemical synthesis* / Q000378:metabolism; D011409:Propylene Glycols / Q000138:chemical synthesis* / Q000378:metabolism; D000074262:Rapeseed Oil
D005227:Fatty Acids; D005229:Fatty Acids, Monounsaturated; D009829:Oleic Acids; D010938:Plant Oils; D011091:Polyesters; D011409:Propylene Glycols; D000074262:Rapeseed Oil; C018163:trimethylolpropane; C116457:1-butyl oleate; D008049:Lipase