Acrylic and Styrenic Monomers from Biomass

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1 Acrylic and Styrenic Monomers from Biomass BPM-060 ACTION BPM Symposium, Wageningen, June 27, 2013 Jérôme Le Nôtre Biobased Commodity Chemicals Group

2 Plastics Biobased Non biodegradable Bioplastics Bio-PE (PP/ PVC), biobased PET, PTT Conventional plastics Nearly all conventional plastics: PE, PP, PS, etc. Biobased Bioplastics PLA, PHA, Starch blends Bioplastics PBAT, PBS, PCL Biobased and Biodegradable Biodegradable Biodegradable Fossil-based Graph: Material coordinate system of bioplastics Prof. Dr. Ing. H.-J. Endres, IƒBB University of Applied Sciences and Arts

3 BPM-060 ACTION subproject Acrylic and Styrenic Monomers from Biomass (ACTION) Aim: To develop scientific and applied knowledge for the generation of efficient synthesis routes to acrylic and styrenic monomers Biobased PS and PMMA Partners: DSM, BASF, Synbra, GreenICT, WUR-FBR, WUR-BCH Intended application area: Packaging materials, foams, adhesives, coatings, optical fibres

4 BPM-060 ACTION subproject Challenges: R - How can we produce styrene and methacrylic acid from biomass? - What are the biobased feedstocks available? - Which biological and chemical steps are needed? - Can they be applied to biobased intermediates? - Is the entire pathway economically viable?

5 Concept Amino Acids R BIOMASS Sugars 2 platform chemicals: Phenylalanine Itaconic acid

6 Amino Acids (Phe) Platform Conversion of Protein Biomass into Styrene and Acrylates: BIOMASS Bio-ethanol DDGS Protein Hydrolysis Separation Deamination (PAL) Amino Acids Deamination (PAL) Cinnamic acid in mixture Purification Cross-metathesis Vinasse, Protamylasse Styrene Acrylic acid

7 Amino Acids (Phe) Platform Bio-chemical platforms: proteins Example: Dried Distillers Grains and Solubles (DDGS) from Bio-ethanol BIOMASS Bio-ethanol Waste Stream: DDGS (35% proteins) ( per ton) Amino Acids Chemicals EU Prognosis 2020: 10% of transportation fuels as bio-fuels 100 mln tonnes of proteins 5 mln tonnes of each AA per annum

8 Amino Acids (Phe) Platform Conversion of Phenylalanine into Styrene and Acrylates: - Phenylalanine to cinnamate esters: - Cinnamate esters to styrene and acrylates:

9 Amino Acids (Phe) Platform Deamination of Phenylalanine: ammonia lyase -NH3 Phenylalanine Cinnamic acid Phenylalanine Ammonia Lyase (PAL): enzyme naturally present in yeasts (Rhodotorula glutinis) (Activity, reaction conditions (ph 8-9, T = o C), inhibition parameters) Study of activity on complex mixtures of amino acids (DDGS hydrolysates)

10 Amino Acids (Phe) Platform Conversion of Phenylalanine into Styrene and Acrylates: Cinnamate esters to styrene and acrylates: Ethenolysis reaction Type of catalysts: - Homogeneous (Ru, Mo, W) - Heterogeneous (Re, Mo)

11 Amino Acids (Phe) Platform Ethenolysis applied to biomass - Fatty esters: Ru Grubbs Ethylene Methyl Oleate Maughon et al., Organometallics 2004, 23, Fumaric acid: 2 ROH Fumaric acid Fumaric acid diester Ethylene 2.5 mol% Ru Grubbs 2 Acrylic acid ester Genomatica Inc., International Patent Application (2009), WO2009/045637A2.

12 Amino Acids (Phe) Platform Ethenolysis applied to biomass (0.05 M, R = H, Et, n-bu) Catalyst screening: Catalyst: Hoveyda-Grubbs 2 nd generation i) J.P.M. Sanders, J. van Haveren, E.L. Scott, D.S. van Es, J. Le Nôtre, J. Spekreijse, Int. Pat. Appl. (2011), WO2011/002284A1. ii) J. Spekreijse, J. Le Nôtre, J. van Haveren, E.L. Scott, J.P.M. Sanders, Green Chem. 2012, 14, 2747.

13 Conversion(%) Amino Acids (Phe) Platform Ethenolysis applied to biomass Cinnamate esters to styrene and acrylates: (0.05 M, R = H, Et, n-bu) Catalyst: M substrate, 5 mol% HG-2 nd, DCM, 40 C, 24 h Cinnamic Acid acid Ethyl Acrylate cinnamate Hoveyda-Grubbs 2 nd generation i) J.P.M. Sanders, J. van Haveren, E.L. Scott, D.S. van Es, J. Le Nôtre, J. Spekreijse, Int. Pat. Appl. (2011), WO2011/002284A1. ii) J. Spekreijse, J. Le Nôtre, J. van Haveren, E.L. Scott, J.P.M. Sanders, Green Chem. 2012, 14, Ethene pressure (bar) Higher ethylene pressure leads to lower conversion

14 Amino Acids (Phe) Platform Ethenolysis applied to biomass R Conversion into products [a] H 31% Et 28% n-bu 39% ( [a] 20-40% of stilbene was formed) Side reaction: styrene self-metathesis ethylene pressure, conversion and selectivity (Mechanisms competition) i) J.P.M. Sanders, J. van Haveren, E.L. Scott, D.S. van Es, J. Le Nôtre, J. Spekreijse, Int. Pat. Appl. (2011), WO2011/002284A1. ii) J. Spekreijse, J. Le Nôtre, J. van Haveren, E.L. Scott, J.P.M. Sanders, Green Chem. 2012, 14, 2747.

15 Amino Acids (Phe) Platform Ethenolysis applied to biomass Influence of ethylene pressure and substrate concentration: Catalyst Ethylene DCM, 40 o C, 24 h Substrate (M) P ethylene (bar) Catalyst (mol%) Conversion* (%) Selectivity** (%) Reaction conditions: Reaction time = 24 h, Catalyst = 5 mol% Hoveyda-Grubbs 2 nd generation. *Conversion measured by 1 H NMR. **Stilbene appears as by-product. i) J.P.M. Sanders, J. van Haveren, E.L. Scott, D.S. van Es, J. Le Nôtre, J. Spekreijse, Int. Pat. Appl. (2011), WO2011/002284A1. ii) J. Spekreijse, J. Le Nôtre, J. van Haveren, E.L. Scott, J.P.M. Sanders, Green Chem. 2012, 14, 2747.

16 Amino Acids (Phe) Platform Ethenolysis applied to biomass Application to other amino acids: Tyrosine, Histidine R = Et, 21% conversion R = Bu, 25% conversion No side-reaction

17 Sugars (Itaconic acid) Platform BIOMASS Sugars Fermentation Esterification Isomerisation Cross-metathesis + Methacrylates Acrylates

18 Sugars (Itaconic acid) Platform Esterification/Isomerisation of itaconic acid:

19 Sugars (Itaconic acid) Platform Ethenolysis of mesaconic and citraconic acid ethyl esters: - Different solvents used - Temperature: o C - Ethylene pressure: 1 35 bar - Reactions performed on citraconate ester, citraconic anhydride, corresponding acids - 9 Ruthenium-based and 1 Molybdenum-based homogeneous catalysts tested.

20 Conclusions Future Plans - Itaconic acid and phenylalanine are potential platform chemicals. - Access to a variety of biobased monomers: methacrylic acid, acrylic acid, styrene. - Phenylalanine can be converted into cinnamic acid using PAL enzyme. - Ethenolysis can be applied to cinnamic acid, a challenging substrate. - Atom-efficient conversion to acrylates and styrene in one step Phe: 15% conversion, 100% selectivity Tyr: 25% conversion, 100% selectivity Apply the phenylalanine deamination reaction to real rest streams Recovery of cinnamic acid from enzymatic broth Improve the ethenolysis step: - conversion, selectivity - heterogeneous catalysts

21 Acknowledgments Biobased Commodity Chemicals Group Prof. Dr. Johan P. M. Sanders (Prof. Dr. Harry Bitter) Dr. Elinor L. Scott Susan Witte Biobased Products Group Dr. Jacco van Haveren Dr. Ir. Carmen Boeriu Ing. Marinella van Leeuwen

22 Questions?

23 Sugars (Itaconic acid) Platform Ethenolysis of test substrates: Good conversion Substrate Reactivity: Low conversion No conversion Low conversion

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