From chewing gum to lignin (and back to chewing gum again)

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June Paul
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1 From chewing gum to lignin (and back to chewing gum again) Gill Stephens Biorenewables and Bioprocessing Group Process and Environmental Research Division Department of Chemical and Environmental Engineering, University of Nottingham, University Park, Nottingham NG7 2RD Tel: +44 (0)

2 Where will we get aromatic chemicals when oil runs out?

3 Where will we get aromatic chemicals when oil runs out? Lignin would be a superb source of aromatic building blocks......except that chemical depolymerisation is unselective and too vigorous

4 Enzymes catalyse controlled depolymerisation of lignin... O 2 Laccase Oxidized mediator Lignin H 2 O Oxidized laccase Mediator Oxidized lignin Remazol Brilliant Blue (RBB) Benzotriazole (BT) Hydroxybenzotriazole (HBT) 2,2 -Azino-bis(3-ethylbenthiazoline- 6-sulfonic acid) (ABTS)

5 .except that mass transfer problems hinder depolymerization 5

6 We have developed an enzymatic process to dissolve discarded chewing gum Compositions and methods for the removal of chewing gum residues from substrates GB ,

7 The process uses laccase to degrade the gum O 2 Laccase Oxidized mediator Gum H 2 O Oxidized laccase Mediator Oxidized gum

8 .but mass transfer problems hinder depolymerization 8

9 The process uses ionic liquids to soften the gum N N O S O - O O Ionic liquids are salts that do not form crystals at room temperature Cl - Na + (unlike NaCl)

10 Laccase is active in ionic liquids Cation Anion V max [%aq] K M [%aq] Phase behaviour [P 8,8,8,14 ] [Br] 121 ± 2 94 ± 33 Biphasic [P 6,6,6,14 ] [SCN] 46 ± ± 11 Biphasic [P 6,6,6,14 ] [N(CN) 2 ] 53 ± 2 62 ± 9 Biphasic [P 6,6,6,14 ] [TFA] 82 ±2 884 ± 7 Single [P 6,6,6,14 ] [C 9 COO] 84 ± 9 93 ± 3 Biphasic [P 6,6,6,14 ] [NTf 2 ] 114 ± 5 76 ± 9 Biphasic [N 1,2,2,2 ] [C 1 SO 4 ] 127 ± ± 9 Single [N 4,4,4,4 ] [AOT] 109 ± ± 3 Biphasic [N 1,1,4,10 ] [NTf 2 ] 69 ± ± 5 Biphasic [N 1,1,2,1CN ] [NTf 2 ] 77 ± ± 6 Biphasic [N 1,2,2,2O2O-quinoline ] [NTf 2 ] 91 ± ± 7 Biphasic [C 3 OCpip] [NTf 2 ] 83 ± 4 76 ± 11 Biphasic [C 2 mim] [C 8 SO 4 ] 26 ± ± 12 Single [C 4 mim] [iso-c 4 SO 4 ] 71 ± ± 12 Single [C 4 mim] [C 2 OC 2 SO 4 ] 86 ± ± 19 Single [C 4 mim] [AOT] 91 ± ± 12 Biphasic [C 4 mim] [PF 6 ] 78 ± ± 4 Biphasic [C 4 eim] [NTf 2 ] 82 ± 1 87 ± 5 Biphasic [C 10 mim] [NTf 2 ] 82 ± ± 12 Biphasic [NC 2 mim] [NTf 2 ] 46 ± ± 9 Biphasic

11 .problem solved BEFORE AFTER 11

12 Ionic liquids can ALSO be designed to dissolve lignin

13 Lignin is the natural substrate for laccase O 2 Laccase Oxidized mediator Lignin H 2 O Oxidized laccase Mediator Oxidized lignin Remazol Brilliant Blue (RBB) Benzotriazole (BT) Hydroxybenzotriazole (HBT) 2,2 -Azino-bis(3-ethylbenthiazoline- 6-sulfonic acid) (ABTS)

14 Objective Can enzymes be used to depolymerise lignin dissolved in ionic liquids?

15 Guess what? IL + water + lignin IL + water + lignin + enzyme

16 But does this make useful chemicals? Product analysis Product analysis Product analysis Product analysis Product analysis

$fraction Ethyl acetate Solid fraction Ethyl acetate 88% 10% 0.$ 5% 1.5% 17 GCMS and LCMS to identify products HPLC for

17 Sample preparation and analysis Enzyme digest H 2 SO 4 Liquid fraction Ethyl acetate Solid fraction Ethyl acetate 88% 10% 0.5% 1.5% 17 GCMS and LCMS to identify products HPLC for quantification GPC and NMR to characterise residual lignin and repolymerised products

18 Major products (softwood) CHO CO OMe OMe Vanillin Vanillic acid

19 Products in ethyl acetate Minor products extract of liquid fraction CHO CO O CO CHO OMe Catechol Guaiacol OMe OMe OMe Isovanillin Isovanillic acid Acetovanillone p-toluic acid 4-Hydroxy benzaldehyde O O MeO OMe Propiophenone Tyrosol Homovanillyl alcohol Phenol 4-Methyl benzaldehyde

20 Future work BENEFITS OF A BBSRC FELLOWSHIP 20

21 Ideas How to make >30,000 chemical products from biomass?

22 New collaborations

23 Industrial sponsors Company X Sponsoring 4 CASE students; PDRA contract Company Y Short contract agreed; in negotiation

24 Which brings us back to chewing gum RENEWABLES AND WASTES Monomers and bulk chemicals

25 Benefits

26 New posts in Industrial Biotechnology Chair Metabolic engineering/synthetic biology Four Lectureships Directed Evolution/metagenomics Bioreaction Engineering Synthetic biology (Biorenewables, bioenergy) Synthetic biology (Microbial pathogenesis)

Properties of Compounds

Chapter 6. Properties of Compounds Comparing properties of elements and compounds Compounds are formed when elements combine together in fixed proportions. The compound formed will often have properties