wow project review
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WOW Project Review
Weds 21st AprDr Stuart Coles
Chemistry / WMG
2
Introduction• Potential breakdown products
– Commercially available– Synthetic routes
• Model breakdown products– Functionalisation– Polymerisation
• Summary
Synthesis
O
OMe
OH
OH
3
O OH
MeO
OH
OH
1
O
HO
OMe
OH
HO
OMe
OH
O
4
O OH
MeO
OH
CO2H
2
Synthesis
O
OMe
OH
OH
3
O OH
MeO
OH
OH
1
O
HO
OMe
OH
HO
OMe
OH
O
4
O OH
MeO
OH
CO2H
2
Obtained commercially from Apin Chemicals.
Synthesis of 3CO2H
HO
OMe
CO2Me
TBSO
OMe
1. MeOH, H2SO4
2. TBSCl, imid., THF
TBSO
OMe
O
Si
SiClMg, I2,
N-methylpyrrolidinoneO
OMe
OH
OH
3
Synthesis of 4
CO2H
MeO
OH
OH
OMe
CO2H
CHO
MeO
OH
CHO
MeO
OH
OH
OMe
CHO81% 33% (3 steps)
Products from Extractions• Conversion of ‘model feedstocks’ into polymeric materials• Two initial materials were identified
HO
OH
O
O
HO
OH
OMe
Chrysin Vanillyl Alcohol
8
Direct Polymerisation• Vanillyl alcohol reacted with with three different diisocyanates
OCN NCO
OCN NCO
OCNNCO
MDI
TDI
HDI
HO
OH
OMe
Vanillyl Alcohol
Direct Polymerisation• Product looks like this (example shown with TDI) :
• However – poor solubility of product prevents complete characterisation– Standard techniques for characterising polymers include
NMR, GPC & MALDI all require solutions• Elemental analysis shows polymers do not have expected
composition
NH
NH
O
O
O
OMe
O
On
IR
TGA & DSC
0 50 100 150 200 250 300 350 40050
60
70
80
90
100
MDIHDITDI
Temperature / °C
Perc
enta
ge M
ass R
emai
ning
0 50 100 150 200 2500
0.5
1
1.5
2
2.5
Temperature / °C
Valu
e /
mW
TGA traces of polymers
DSC trace of TDI-based polymer
Direct Polymerisation• Current work focusing on making prepolymers to determine
structure
NH
HN
O
O
OOMe
HO
O
OMe
OH
Functionalisation• Chrysin was functionalised with a methacrylate group and
subsequently polymerised.
• Polymer characterised by GPC– Mw = 45,024; Mn = 7,249; PDi = 6.21
HO
OH
O
O
Chrysin
O
OH
O
O
O
14
Summary• Two of four target compounds have been purchased• One target compound has been synthesised• Investigation towards polymers from breakdown products
remains ongoing with a view to publication
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