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WOW Project Review. Friday 2 nd October 2009 Chemistry. Introduction. Degradation Bacterial degradation of lignin. Assay and bio-prospecting Extractions Improvements and alternative methods Analysis Identification of compounds Materials Uses and potential markets of breakdown products

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wow project review

WOW Project Review

Friday 2nd October 2009

Chemistry

introduction
Introduction
  • Degradation
    • Bacterial degradation of lignin. Assay and bio-prospecting
  • Extractions
    • Improvements and alternative methods
  • Analysis
    • Identification of compounds
  • Materials
    • Uses and potential markets of breakdown products
  • Other
    • Links to electrospinning, biocomposites

2

summary last review
Summary-last review
  • Determine suitable methods for extraction of degrading straw, using both aqueous and organic solvents.
  • Identify (from literature search) and subsequent training / obtaining of suitable equipment for analysis of extracts.
  • Develop characterisation methods for extracts based on literature protocols, in particular, looking at MALDI, GC-MS & LC-MS.
  • Develop synthetic methods for materials from potential / model breakdown products.
  • Use crude breakdown mixture to produce material based on 4.
  • Set up large scale (20 L) reactor
slide5

Lignin is a major component of plant cell walls

peroxidases

laccases

Lignin-degrading

microbes

Bacterial

aromatic

degraders

slide6

Assay can distinguish degraders from non-degraders:

Time dependence (0-2 hr)

Non-degraders

Fluorescent Assay for Lignin Degradation

Paper Submitted to Molecular Biosystems

slide7

Time dependence (0-20 min)

Specificity of bacterial lignin degraders towards

MWL from pine, wheat straw & miscanthus:

Rhodococcus RHA1

not selective

Distinguishes lignin degraders

from non-degraders

Nocardia autotrophica

shows selectivity

for pine lignin

Continuous UV-VIS Assay using Nitrated Lignin

Paper Submitted to Molecular Biosystems

large scale extraction
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
hexane extraction
Hexane Extraction
  • Recent research suggests that hexane can be used to extract triglycerides and fatty acids from straw.1
  • Straw placed in soxhlet and extracted with hexane (200 mL) for 24 h.
  • Fatty acid and triglyceride mixture is collected in the distillation flask away from the straw

1 I. M. G. Lopes, M. G. Bernado-Gil, Eur. J. Lipid. Sci. Technol., 2005, 107, 12-19

hexane extraction results
Hexane Extraction - Results

It would appear that a higher content is made available by degradation, but it is unknown to the origin of the material.

slide13

HPLC traces with time

Non-degrader Bacillus subtilis

shows no change

Degrader Pseudomonas putida

slide14

GC-MS data for small scale lignocellulose degradation trials

GC-MS total ion chromatogram with EI ionisation for Rhodococcus RHA1incubated with wheat straw lignocellulose for 7 days at 30 oC.

Mass spectrum of peak at RT 7.02 min, assigned to monosilylated derivative of ketone (1), m/z 268 (M-SiMe3)+, 253 (M-SiMe3-CH3)+.

analysis
Analysis
  • Extracts have been analysed using LTQ-MS at HRI
    • Separates and detects using UV and MS

15

slide18

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

other potential major degradation products yet to be fully identified from wheat straw
Other potential major degradation products-yet to be fully identified from wheat straw

No current market.

Potential in poly-ethers,

-ester or -urethanes

Vanillic acid precursor?

Diacid for use in polyesters

and polyamides

Derivative of Gallic acid.

Anti-fungal, anti-viral,

anti-oxidant.

Gallic acid is used in dyes

and inks.

hexane extraction potential
Hexane Extraction - Potential
  • Must be carried out before the water extraction
  • Fatty acids have potential applications in:
    • Soaps, personal care, perfumes
    • Polymeric species (e.g. plastics, rubber)
    • Lubricants, cleaners, coatings
    • Fatty acid derivatives (e.g. biofuel)
    • Food and related supplements (e.g. bio oils)
  • Around 7 – 8 % by weight of the dry mass is a significant portion of material

22

products from extractions
Products from Extractions

Vanillin derivative.

Used in fragrances, flavouring.

Annual demand for vanillin = 12,000 tons.

Natural source = 1200 tons, synthesis = 10,800 tons

Beneficial effects in atherosclerosis, osteoporosis, diabetes mellitus and certain cancers.

Use as dietary supplements / plant extracts has been steadily increasing. Anti-oxidants.

Conversion of ‘model feedstocks’ into polyurethane materials

Two initial materials were identified

24

slide25

Chrysin: a naturally occurring flavone

Polyurethanes from Flavone derivatives: J. Appl. Poly. Science, In Prep

alternative uses of lignin
Alternative uses of lignin
  • Filler in biocomposite structures
    • May promote resin / matrix adhesion between for natural fibres
  • 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

28

A (DoE) approach to material properties of electrospun nanofibres.

SR Coles, AJ Clark, K Kirwan et al. J. Appl. Poly. Science, 2009 Accepted

slide29

Future work

  • Biodegradation
  • Isolation and purification of degradation enzymes from bacteria.
  • Analysis
  • Continued identification of novel lignin degradation products.
  • Preparation of LC-MS standards for unambiguous identification.
  • Materials
  • Identification of molecules for further study.
  • Scale up of chosen molecules (synthesis)
  • Identification of potential industrial partners (medical / cosmetic ?).
  • Evaluation of estolides as lubricants (Fuchs).
  • Evaluation as novel fatty amides as additives in paints (Akzo Nobel).
  • Evaluation of vanillin and flavone polymers for anti-oxidant / UV stability.
    • Preparation of materials from gallic acid, ferulic acid derivatives.
    • Other
    • Evaluation of lignin incorporation in electrospun fibres and composites.