Dec 10, 2016 - Bio-based surfactants via biocatalysis. ⢠Enzymatic approaches by reverse hydrolysis. ⢠Sugar ester synthesis with lipases. 3. Biosurfactants by ...
Assessment of biotechnological processes towards bio-based surfactants 63rd SEPAWA Congress & 12th European Detergents Conference 12.-14.10.2016, Fulda Ulrich Schörken, Stéphan Barbe
12.10.2016 Slide: 1
63rd SEPAWA Congress & 12th European Detergents Conference, Fulda
Ulrich Schörken, Stéphan Barbe
Content 1. Introduction • Structural diversity of fully bio-based surfactants (and emulsifiers) • Chemical production of bio-based surfactants 2. Bio-based surfactants via biocatalysis •
Enzymatic approaches by reverse hydrolysis •
Sugar ester synthesis with lipases
3. Biosurfactants by fermentation •
Microbial lipopeptides
•
Microbial glycolipids •
Production strategies for sophorolipids
4. Conclusions
12.10.2016 Slide: 2
63rd SEPAWA Congress & 12th European Detergents Conference, Fulda
Ulrich Schörken, Stéphan Barbe
1. Introduction Structural diversity of fully bio-based surfactants and emulsifers Lipophilic tails:
fatty acids, fatty alcohols, terpenes
Hydrophilic headgroups: sugars, amino acids, (natural) polyols, organic acids, phosphoric acid, amines … Natural compounds of biological origin: • Phospholipids, saponins, microbial biosurfactants … Synthetic compounds: • Alkyl glycosides / alkyl polyglycosides (APGs) • Sugar esters (e.g. sucrose esters) • Acylated amino acids and acylated peptides • Monoglycerides and polyglycerol esters / polyol esters (e.g. sorbitan esters) • Monoglyceride – organic acid esters (e.g. Citrems, Lactems …) • … 12.10.2016 Slide: 3
63rd SEPAWA Congress & 12th European Detergents Conference, Fulda
Ulrich Schörken, Stéphan Barbe
1. Introduction Structural diversity of fully bio-based surfactants and emulsifers Dilauroyl phosphatidethanolamine: O H3 C
O
O
CH 3 O
O O
P
O
O
H3N
Saponin Sapindoside A (from soapnut): O O
CH 3 CH 3
OH
O H3 C
HO
CH 3 O
H3 C CH 3
OH OH O
OH
O
CH 3
OH
12.10.2016 Slide: 4
63rd SEPAWA Congress & 12th European Detergents Conference, Fulda
Ulrich Schörken, Stéphan Barbe
1. Introduction Structural diversity of fully bio-based surfactants and emulsifers APG: Lauryl diglucoside OH HO
CH3
O
O
O O
HO OH
OH
HO OH
Sugar ester: Dilauroyl sucrose CH3
HO
O
HO O
O HO
O HO
O
O O HO
OH
CH3
12.10.2016 Slide: 5
63rd SEPAWA Congress & 12th European Detergents Conference, Fulda
Ulrich Schörken, Stéphan Barbe
1. Introduction Structural diversity of fully bio-based surfactants and emulsifers Acylamino acid: Lauroyl-N-glutamate O
O
H3 C
O O
N H
O
Acylpeptide: Lauroyl-N-Lys-Ser-Glu H N
H3 C O
OH
O N H
O
H N O
O
O O
NH 3
12.10.2016 Slide: 6
63rd SEPAWA Congress & 12th European Detergents Conference, Fulda
Ulrich Schörken, Stéphan Barbe
1. Introduction Chemical production of bio-based surfactants APG (alkyl polyglycoside) process: •
C1-selective acid catalyzed acetalization of glucose with fatty alcohols
•
Fatty alcohol / APG separation by short path and thin film distillation Vacuum 1
Vacuum 2
FOH
Recycle FOH
M
Dextrose
M
Water
Catalyst Base
Vacuum 3
M
C1-selectivity O
OH + H H2O
O
S elective nucleophilic attack on stabilized carbenium ion
ROH
O 20-50% APG® 80-90% APG® 50-80% FOH 10-20% FOH
APG® melt (
