Escolar Documentos
Profissional Documentos
Cultura Documentos
Joseph J. Bozell
Outputs (Conversion)
Inputs (Supply)
Butadiene
Building blocks Polylactic acid
(Separation) Pentanes, pentene
Corn BTX
Switchgrass Succinic acid
Potatoes Phenolics
Sorghum Starch Ethanol
Soybeans Organic acids
Cellulose
Apple pomace Furfural
Jerusalem artichoke Lignin
Polyols
Guayule Other Carbohydrates Resorcinol
Beet molasses Oils Levulinic acid
Sugar cane Levoglucosan
Wood Peracetic acid
Residues Tetrahydrofuran
Anthraquinone
Sorbitol
others
Forest Products Matrix
Wood
processing
Timber products, Wood as wood;
plywood, OSB, etc. relative value low
Conventional
Kraft
Wood for paper
Cellulose
and fuel; relative value
Forest Black liquor
low to mid
(renewable) Alkali
resource extraction
Cellulose Wood for paper, fuel,
Hemicellulose and commodities; relative
Black liquor value low to mid
Emerging
Advanced
fractionation Cellulose
Hemicellulose Wood for chemicals;
Lignin relative value mid
Sugars to high
Extractives
Strategic Goals for the Use of Renewable
Feedstocks and Biorefinery Development
R. Dorsch and R. Miller, World Congress on Industrial Biotechnology and Bioprocessing, April 2004, Orlando, FL
What Product Should We Make?
Woody
biomass
Lignin based aromatic
chemicals
Sugar/cellulose based
chemicals
Biobased
Pulp and paper fuels
products
2005: Nanotechnology for
the Forest Products Industry
What Will The Forest Products Biorefinery Look
Like?
Woody
biomass
Lignin based aromatic
chemicals
Sugar/cellulose based
chemicals
Biobased
Pulp and paper fuels
products
Natural Polymers as Templates
Biomaterials 06/27/4661
Medical diagnostics,
biochips, biosensors
Nanomolar sensitivity for
detection of biotin-
containing species
Cellulose provides a new
set of support properties
Angew. Chem. Int. Ed. 06/45/2883
O O
HO
OH
O O OH OH
HO
OH OH OH
OH
O
Me N Me HO O COOH
HO
Me H HO O O
BrEt3N NEt3Br HO A naturally occurring sophorolipid from
H H 18
HO Candida bombicola
N OH
Me H Langmuir 2004, 20, 7926
Me
Me
COOH
HOOC
OH OH OH OH
OMe
HO OH
NH CH2 NH
COOH Me OH OH 6 OH OH
Carbohydrate and glycal based bolaforms
OAc OAc
O 1) NaN3 O 1) ClC(O)(CH2)nC(O)Cl
AcO NH2
AcO
AcO AcO 2) NaOMe
OAc 2) H2, Pt OAc
Br
OH HO
O O
HO NH HN OH
HO n OH
OH O O HO
OAc RO OR
O O OR RO O
AcO
AcO OR n RO
gl ycals gl ycal base d bo lafo rms bo lafo rm ba sed mono layer m embra nes
predictive models?
org anom etal lic OR structure shape
tra nsfo rmati ons
O
OAc
O OAc
OAc OAc
O O AcO O O
OH O O
OAc
AcO AcO
OH
OH
NaOMe, MeOH O O
O O
OH
HO
Starting glycals
OAc OH
O 1) cat. I2, THF O O
R
ROH
AcO 2) NaOMe HO
OAc
500 nm 500 nm
OH
OH
O O
O O
OH
HO
OH O
O H
N NH2
HO N
HO OH H
O
R
O OH
H R T. Shimizu, Carb. Res. 2000, 326, 56
O O OH
HO R
O H OH O
H R
O H O
OH
O
H O
R R O
R H
O O O H O
R
O H H
HO O O
H H H
H O
O
O O
OH
Glucal; ,-diastereomer
Glucal; ,-diastereomer
Galactal, ,-diastereomer
OH
OH O
O OH
N O
HO N
OH O
HO
OH Masuda, Shimizu, Carb. Res. 2000, 326, 56
OH
Comparative Hydrogen Bonding Networks
OH
OH O
O OH
N O
HO N HO
HO HO OH OH
OH O OH O O
OH
O
O
Disaccharide Bolaform Headgroups
OH OH
O HO OH
lactose O OH
HO OH O
OH
OH
O
maltose HO OH
HO O 1) Ac2O, HBr/HOAc
OH
O OH
HO
OH
OH 2) HBr/HOAc
O HO OH
HO O
cellobiose OH 3) Zn/CuSO4/NaOAc/H2O/HOAc
HO OH O
OH
O HO OH
HO O Koreeda, et al
xylobiose OH
HO OH O
OAc OAc
O AcO
O
AcO OAc O
1) HO(CH2)12OH
OAc OH OH HO OH
lactal, 50% I2, THF O O
O O(CH2)12O O
2) NaOMe, HO OH O OH
OAc O HO
O MeOH OH HO
AcO OAc
AcO O
OAc
O
AcO
maltal, ~50%
Chemical Stabilization and Bioactive Materials
HO OH
HO OH
OH O
HO O O O
OH OH O
HO O O O
O HO OH O HO
O O HO O
O O O O
HO O HO OH O O O
OH O HO OH
OH HO OH
O
microbial cellulose O
cellulose
O functionalization
HO OH
M M
bioactive molecules (M) S S S S S S
cellulose fiber
200m 200m
200m 200m
No bolaform added
AFM Images of Bola/Cellulose Film
4% avicel in DMAc/LiCl 4% avicel in DMAc/LiCl, 5% bola
Alignment of Carbohydrates
H
H O O
O
O O
O O H
H O H O HO
H
O O OH
HO
O HO
O
OH
OH
HO
HO
O
OH O
OH
Hypothetical organization of cellobiose
HO O O
OH H
O H H
O
H O O
O
O
O O H
O
H
H
H O O O
O O
O O H
H O H O
H HO
O O OH
OH HO O OH
HO O HO OH O
O OH HO
HO O O
OH O H
H O H
Maintenance of
O
H
nanostructures H O O O
H
H-bonding network
O O
O O H
H O H O
H HO
O O OH
OH HO O OH
HO O HO OH O
O OH HO
HO O O
OH O H
H O H
H O O O
O
O O O H
H
H
H O O O
O O
O O H
H O H O
H HO
O O OH
OH HO O OH
HO O HO OH O
OH
Additional stabilization
O HO
HO O O
OH O H
H O H
H O O O
alignment of hydrophobic
H
H O O O
O O
O O H
chains? H O H O
H HO
O O OH
OH HO O OH
HO O HO OH O
O OH HO
HO O O
OH O H
H O H
H O O O
O
O O O H
H
Conclusions and Acknowledgements
Funding:
USDA/NRI