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Renewable feedstocks Thursday 29th October 2009.

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Presentation on theme: "Renewable feedstocks Thursday 29th October 2009."— Presentation transcript:

1 Renewable feedstocks Thursday 29th October 2009




5 Adapted from Introduction to Chemicals from Biomass, ed. Clark, J.; Deswarte, F. Wiley, 2008

6 Chemicals from Crude oil

7 Oil  Brassica  Artemisia Artemisinin Animal feed Biofuels Food  Wheat (straw) Animal feed Lignocellulose Food

8 Lignin Cellulose Hemi-cellulose Cell membrane Artemisia annua Artemisinin Artemisinin derivatives Flavonoids, Terpenes & other phenolics WaxesSugars


10 Flavones Functionalizing Flavones

11 Monomers for polyester formation

12 Monomers for polyether formation Monomers for methacrylate formation



15 Lignin is a major component of plant cell walls Lignin-degrading microbes Bacterial aromatic degraders

16 Fluorescent Assay for Lignin Degradation Time dependence (0-2 hr) Non-degraders Assay can distinguish degraders from non-degraders: Tim Bugg, Paper Submitted to Molecular Biosystems

17 Large Scale Extraction 1.5 kg (wet) of P.chrysosporium-degraded straw was extracted using 20 L reactor 12 L of water and 8 L of THF used to extract straw THF was used due to combination of interesting peaks from LTQ analysis and mass recovered in previous trials 17 ExtractMass (g)Percentage of total (wet) Percentage of total (dry) Aqueous156.8810.6%38.6% Organic14.50.98%3.57% Dry Straw235.315.9%57.9% Water content-72.7%-

18 HPLC traces with time Degrader Pseudomonas putida Non-degrader Bacillus subtilis shows no change

19 GC-MS data for small scale lignocellulose degradation trials GC-MS total ion chromatogram with EI ionisation for Rhodococcus RHA1 incubated with wheat straw lignocellulose for 7 days at 30 o C. Mass spectrum of peak at RT 7.02 min, assigned to monosilylated derivative of ketone (1), m/z 268 (M- SiMe 3 )+, 253 (M-SiMe 3 - CH 3 )+.

20 Aromatic metabolites identified (so far) CompoundLC-MS Retention time (min) LC-MS m/z GC-MS Retention time (min) GC-MS m/z (silylated) Observed with.. 14.29235 MK + 7.02268 M + 253 -CH 3 P. Putida 6hr, 1d, 3d Rhodococcus RHA1 2hr, 4hr Miscanthus & wheat straw 24.56209 MNa + 225 MK + 7.71243 M + 228 -CH 3 P. Putida (straw) 7d Rhodococcus RHA1 Miscanthus 1d, straw 2d 35.25195 MH + 5.27251 M-CH 3 P. Putida 6hr Rhodococcus RHA1 2hr, 6hr Miscanthus only 45.76251 MK + 6.03341 M- CH 3 P. Putida 6hr Rhodococcus RHA1 4hr, 6hr Miscanthus only 59.09169 MH + Rhodococcus RHA1 6hr Miscanthus only

21 Ferulic acid. 379 papers in 2008-9 on biological activity alone £1 per 1g Anti-oxidant Active breast cancer, liver cancer Active ingredient in anti-ageing creams / plumping creams Carboxy vanillic acid. 0 papers in 2008-9 Potential use as fine chemical building block. Vanillic acid precursor. Diacid for use in polyesters and polyamides

22 Other potential major degradation products- yet to be fully identified from wheat straw Derivative of Gallic acid. Anti-fungal, anti-viral, anti-oxidant. Gallic acid is used in dyes and inks. No current market. Potential in poly-ethers, -ester or -urethanes Vanillic acid precursor? Diacid for use in polyesters and polyamides


24 ’00’ Canola High ErucicHigh Oleic Natural profiles of some rapeseed oils now available

25 Polyurethanes (polymers)

26 Composite type Fibre volume (%) Tensile strength (MPa) Young’s Modulus (GPa) Composite density (Kg/m 3 ) Impact strength (kJ/m 2 ) HEMP/ EUPH21.0522.91 (1.06) 2.31649.5518.81 (2.17) HEMP / RAPE19.9238.84 (2.21) 3.40697.099.25 (1.21) JUTE / EUPH23.7755.52 (2.60) 4.26658.5910.60 (2.27) JUTE / RAPE23.7446.38 (3.37) 3.89704.9313.70 (1.95) Vegetable Oils as Polymer Feedstocks (monomers) Rapeseed oil Euphorbia oilJuteHemp



29 Wax Extraction - Results It would appear that a higher content is made available by degradation, but it is unknown to the origin of the material. Straw TypeProcessingExtracted mass / mg % dry mass extracted UntreatedNone801.84 UntreatedWater240.55 UntreatedChopped1001.77 P. ChrysosporiumNone3107.40 P. ChrysosporiumWater400.96 P. ChrysosporiumChopped2305.35

30 Tungstan mediated fatty acid functionalisation: J. Appl. Poly. Science, In Prep

31 Future work

32 Expand to renewable ’Waste Products’ further down manufacturing line. e.g. food industry, Confectionary Use outputs to make demonstrator pieces for media and industrial dissemination




36 Electrospinning Lignin Filler in biocomposite structures May promote resin / matrix adhesion between for natural fibres Future work Use in electrospun nanofibres Solutions not ideal for electrospinning Potential to be co-spun with other polymers (e.g. PVOH) Degradation products may have beneficial anti-oxidant properties which can be incorporated

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