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    Biobased Polyurethanes From Microalgae: DR Philip B. Sellars

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    Carlotta C.
    This document summarizes a project that aims to produce biobased polyurethanes from microalgae. A consortium of organizations is optimizing microalgae strains, cultivating the algae, and extracting and processing the algal oil. The algal oil is being used to produce polyols, which are then reacted with isocyanates to synthesize polyurethanes. Initial polyurethane synthesis trials with algal and fish oil-derived polyols produced materials with a range of properties. The project is also pursuing routes to produce biobased diisocyanates from unsaturated fatty acids.

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    Biobased Polyurethanes From Microalgae: DR Philip B. Sellars

    Uploaded by

    Carlotta C.
    96 views30 pages
    This document summarizes a project that aims to produce biobased polyurethanes from microalgae. A consortium of organizations is optimizing microalgae strains, cultivating the algae, and extracting and processing the algal oil. The algal oil is being used to produce polyols, which are then reacted with isocyanates to synthesize polyurethanes. Initial polyurethane synthesis trials with algal and fish oil-derived polyols produced materials with a range of properties. The project is also pursuing routes to produce biobased diisocyanates from unsaturated fatty acids.

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    6.8-Sellars-1.pdf

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    This document summarizes a project that aims to produce biobased polyurethanes from microalgae. A consortium of organizations is optimizing microalgae strains, cultivating the algae, and extracting and processing the algal oil. The algal oil is being used to produce polyols, which are then reacted with isocyanates to synthesize polyurethanes. Initial polyurethane synthesis trials with algal and fish oil-derived polyols produced materials with a range of properties. The project is also pursuing routes to produce biobased diisocyanates from unsaturated fatty acids.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    96 views30 pages

    Biobased Polyurethanes From Microalgae: DR Philip B. Sellars

    Uploaded by

    Carlotta C.
    This document summarizes a project that aims to produce biobased polyurethanes from microalgae. A consortium of organizations is optimizing microalgae strains, cultivating the algae, and extracting and processing the algal oil. The algal oil is being used to produce polyols, which are then reacted with isocyanates to synthesize polyurethanes. Initial polyurethane synthesis trials with algal and fish oil-derived polyols produced materials with a range of properties. The project is also pursuing routes to produce biobased diisocyanates from unsaturated fatty acids.

    Copyright:

    © All Rights Reserved
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    Download as pdf or txt
    of 30

    Biobased polyurethanes from

    microalgae
    Dr Philip B. Sellars
    High value-added chemicals and BIoreSIns
    from alGae biorefineries produced from CO2
    provided by industrial
    emissions
    Project

    3
    Project consortium
    • Microalgae strain optimisation: PHYCOSOURCE, BIO FUEL SYSTEMS
    • Microalgae production and optimisation: BFS, CASPEO
    • Bio-oil fractionation and thermo-chemical processing: BFS, VTT, 3V
    MABO SPA
    • Synthesis and evaluation of diols, diisocyanates, polyurethanes:
    CUSA, AIMPLAS, UNIVERSITY OF WARWICK
    • Amino acid production: GBR.AT
    • Aromatic and heterocycle derivatives processing for surfactants,
    inks and anticorrosive coatings: CRODA, SUNCHEM, BECKERS,
    UNIVERSITY OF BANGOR, AIMPLAS
    • Integrated designs for industrial-scale value chains: PDC

    4
    Algae oil
    • Nannochloropsis gaditana cultivated in vertical bioreactors by Bio
    Fuel Systems (Alicante, Spain)
    • Extraction with ethanol carried out by VTT Technical Research
    Centre (Espoo, Finland)
    • FAME analysis of triglyceride shows major composition is:
    - 22% methyl palmitate
    - 27% methyl palmitoleate
    - 33% methyl eicosapentaenoate

    5
    Algae oil
    • Algae oil from initial extraction is not clean enough for use in
    desired reactions
    • Further extraction with acetone allows removal of some acetone-
    insoluble phospholipids, facilitating aqueous work-up in subsequent
    reactions
    • Dark colour of oil is transferred into reaction products – this is a
    problem for desired end use as an adhesive for food packaging

    6
    Algae oil
    • Attempts at bleaching algae oil with adsorbents – Fuller’s Earth,
    Activated Charcoal – gave poor mass return
    • Algae oil converted to methyl ester

    • Bleaching carried out with sodium hypochlorite, Fuller’s Earth and


    Activated Charcoal to give amber-coloured oil

    7
    Algae oil

    8
    Project overview

    9
    Algae oil polyols
    Fish oil

    Algae oil

    10
    Algae oil polyols
    Fish oil Algae oil

    11
    Algae oil polyols

    12
    Algae oil polyols

    13
    Algae oil polyols

    14
    Algae oil polyols

    15
    Algae oil polyols

    16
    Algae oil polyols

    17
    Algae oil polyols

    18
    Algae oil polyols

    19
    Algae oil polyurethanes
    • Small-scale polyurethane synthesis trial with fish oil and algae oil
    polyols
    • 1:1 mixture of polyol/MDI functional groups based on hydroxyl
    functionality of polyol
    Polyol OHV OH functionality Appearance
    FO epoxide (0.4eq) 62.6 0.44 oily/waxy
    FO epoxide (2eq) 196.9 1.48 viscous & tacky
    FO diethanolamide 220.0 1.57 slightly pliable solid
    FO ethanolamide epoxide 280.5 2.14 solid foam
    AO epoxide (“0.4eq”) 70.1 0.47 oil
    AO epoxide (“2eq”) 173.9 1.27 viscous & tacky
    AO diethanolamide 203.5 1.30 solid
    AO ethanolamide epoxide 247.5 1.81 solid foam
    20
    Algae oil polyurethanes

    21
    Algae oil polyurethanes

    22
    Algae oil polyurethanes
    • Larger-scale polyurethane synthesis carried out with fish oil and
    algae oil diethanolamide and ethanolamide epoxide polyols
    • Polymer samples unsuitable for tensile testing
    – ethanolamide epoxide PUs were difficult to cast (rapid viscosity increase) and
    led to brittle samples
    – diethanolamide PUs were too soft
    • DMTA of diethanolamide PUs was also unsuccessful

    23
    Algae oil polyurethanes
    • Larger-scale polyurethane synthesis carried out with fish oil and
    algae oil diethanolamide and ethanolamide epoxide polyols
    • Polymer samples unsuitable for tensile testing
    – ethanolamide epoxide PUs were difficult to cast (rapid viscosity increase) and
    led to brittle samples
    – diethanolamide PUs were too soft
    • DMTA of diethanolamide PUs was also unsuccessful
    • Samples undergoing lap shear testing to determine adhesive
    properties
    • AO epoxide (“2eq”) polyol in PU formulation testing at CUSA

    24
    Model isocyanate studies

    25
    Existing bio-based diisocyanates

    Hojabri, L.; Kong, X.; Narine, S. S. Biomacromolecules 2009, 10, 884 26


    Model isocyanate studies

    • 1H NMR indicates ~ 80% conversion


    • Less than 20% alkene present – reduction of double bond?
    • Flash column chromatography:
    3.0 g crude material  2.35 g diacid product (78%)
    0.49 g oleic/stearic acid (16%)
    27
    Model isocyanate studies

    28
    Model isocyanate studies
    • Competing dimerisation of thiolactic acid is observed
    • Optimisation of reaction with polyunsaturated fatty acids is ongoing
    • Alternative ene reactions also being tested (e.g. with maleic
    anhydride)

    29
    Acknowledgements

    • Dr Andrew Ross Dr Stuart Coles Dr Andrew Clark

    • Funded by the European Union Seventh Framework Programme


    (FP7/2007-2013) under Grant Agreement No. 613680 (BISIGODOS)

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