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A SolventA Solvent--Free Free BiocatalyticBiocatalytic Process Process for Cosmetic & Personal Care Ingredientsfor Cosmetic & Personal Care Ingredients
Green Chemistry and Engineering Conference, 23 June 2009Green Chemistry and Engineering Conference, 23 June 2009
Stephanie K. Stephanie K. ClendennenClendennen, Ph.D.& Neil W. Boaz, Ph.D., Ph.D.& Neil W. Boaz, Ph.D.
Eastman Chemical CompanyEastman Chemical Company
Cosmetic ingredients: Esters
Category
ActivesPreservativesSunscreensFilm formers
<1%
Esters are a class of cosmetic and personal care ingredients represented across functional categories.
An example of an active is retinol, a proven “anti-aging” ingredient that can Film formers
ExfoliantsSurfactantsThickenersEmulsifiersEmollientsHumectantsSolvents>10%
proven “anti-aging” ingredient that can irritate skin.
Esterification can stabilize retinol and reduce its irritation potential.
2 Making retinyl esters�
Acid chloride (or anhydride) esterification:
R1 Cl
O
+ R23N R NR2
3
O
+
+ R-OH
Cl-
R1 OR
O
+ R23NH+ Cl-
product
b d t
solvent
Process comparison: Retinyl esters Conventional
Biocatalyticby-product
3Solvent is used in the reaction and for purification.
Process comparison: Retinyl esters Twelve Principles of Green Chemistry were applied to the process.
US Patent allowed4
Idebenone esters
Idebenone is an effective antioxidant and a new anti-aging ingredient. A potential drawback of idebenone is irritation.
Idebenone esters were prepared by enzymatic esterification & tested.
5 In vitro assays predict irritation potential.
A long-chain idebenone ester was compared to idebenone in an in vitro
cytotoxicity assay.
Idebenone ester cytotoxicity
80
100
120 Idebenone Ester
Cell Viability
(% of Control)
The idebenone ester is significantly less cytotoxic than idebenone.
0 200 400 600 800 10000
20
40
60
80
Idebenone
Concentration (µM)
Cell Viability
(% of Control)
Mouse
melanocytes;
MTT assay.
6 The idebenone ester process was optimized.
Process comparison: Idebenone esters
Biocatalytic
Process 1
Biocatalytic
Process 2
Biocatalytic
Process 3
Product quality
Yield 98% 98% 99%
Assay 98.4% 98.3% 98.3%
Residual idebenone 0.2% 0.4% 0.6%Residual idebenone 0.2% 0.4% 0.6%
Residual acid 0.2% 0.3% 0.3%
Reaction Solvent
(Liters /kg product)2.87 0 0
Isolation Solvent
(Liters /kg product)7.47 3.37 0
Total solvent
(Liters/kg product)10.34 3.37 0.00
Ready to practice solvent-free.7
Alcohol Reactant Fatty Acid Reactant
Solvent-free biocatalysis
Reaction product is substantially pure, no further processing is required.
Boaz & Clendennen, Cosmetics & Toiletries Magazine, in press.8
Process benefits & impact
� Solvent-free process: no trace solvent residue, reduces purification cost/energy
� High selectivity: low waste, unique additions
� Modest temperature: low energy consumption, minimize � Modest temperature: low energy consumption, minimize oxidative by-products (& color), sensitive materials OK
� Renewable biocatalyst: immobilized for complete removal
� Flexible: many innovative products can be made, raises possibility of product customization
� Global environmental benefit is limited by volume.
9 “Actives” are low volume ingredients.
� Estimate for “actives” is ~1 kMT
� Regional demand for emollient esters:
Cosmetic esters market
Emollient estersEmollient esters VolumeVolume((kMTkMT))
Revenue Revenue ($M)($M)
� Worldwide market for all C&PC esters to $1.8B by 2010 or ~500 kMT
North America 19 53
Europe 32 120
Total 51 173
Sources: 2008 Global Industry Analysis; SRI Consulting Cosmetic Report 2007
10 Look at emollient esters.
Process comparison: Emollient esters
Conventional
11
Reaction temperature is a differentiator.
Biocatalytic
catalyst(re-used)
by-products
volatiles
steam
reaction
deodorizing
raw materials
catalyst(re-used)
Conventional Biocatalytic
inputs raw materials
reaction
outputs
drying
Process comparison: Emollient esters
liquid
outputs
Adapted from Veit, 2004, Eng. Life Sci. 4: 508-511.
100-150oC
>150oC
<100oCliquid
filter aidsolid
drying
filtration
packaging
bleaching
packaging
Batch Continuous
12
Process benefits & impact
� High selectivity: low waste, unique additions
� Modest temperature: minimize oxidative by-products, odor & color, sensitive materials OK
� Renewable biocatalyst: immobilized for complete removal
� Flexible: many innovative products can be produced, allows product customization
� Global environmental benefit is limited by volume
� Continuous: advantaged over conventional & batch synthesis in water use, capital / smaller footprint, energy use.
13 Energy use was compared.
Estimated energy and greenhouse gas savingsper MT of emollient ester
Units ConventionalProcess
Eastman EnzymaticProcess
Savings
Methodology from Thum & Oxenboll, “Biocatalysis: A sustainable process for production of cosmetic ingredients,” IFSCC Congress 2006, Osaka.
Process
Without heat
integration
With heatintegration
Without heat
integration
With heatintegration
Energy (GJ) 4.50 0.84 0.55 77% 86%
Greenhouse Gas
(kg CO2
equivalents)304 57 38 77% 86%
As a reference point, burning 1 gallon of gasoline releases ~10 kg CO2.
14 How good is that?
Emollient Esters Regional Demand
Cosmetic Esters Global Forecast
2010
10,000
100,000
1,000,000
GH
G S
avin
gs (M
T C
O2 e
quiv
ale
nts
)Estimated greenhouse gas potential savings*
based on product volume
Batch Scale
EastmanContinuous Process
Regional Demand 2007
1
10
100
1,000
1 10 100 1,000 10,000 100,000 1,000,000
GH
G S
avin
gs (M
T C
O2 e
quiv
ale
nts
)
Volume (MT)
*Difference between conventional and enzymatic processes.15
Summary
� Biocatalysis is inherently green.
� Solvent-free is greener.
� Green is good for business.
� A solvent-free biocatalytic process is good for the environment.
� The overall benefit is proportional to product volume.
16
Thank you
and Marcie Natale, Sandra Reid, Jeff Clauson, Jim McCaulley
and Robert Lin, Mark Shelton, Michael Wempe.
17
For more information:
www.eastman.com/GreenProcess
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