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Exploratory catalyst screening studies on the liquefaction of model humins from C6 sugars

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Supporting information for:

Exploratory catalyst screening studies on the liquefaction of model

humins from C6 sugars.

Y. Wang, S. Agarwal, Z. Tang, H. J. Heeres*

Chemical Engineering Department, ENTEG, University of Groningen, Nijenborg 4, 9747 AG Groningen, The Netherlands

* Corresponding author: h.j.heeres@rug.nl Electronic Supplementary Material (ESI) for RSC Advances. This journal is © The Royal Society of Chemistry 2016

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3 8 12 16 20 24 28 32 36 40 44 48 52 6400 6600 6800 7000 7200 7400 A b u n d an ce Time (min) 1, DBE (IS) 2, BHT (in solvent)

Figure S2. GC-MS/FID spectrum of a liquid product from an experiment with Pd/C (400 °C, 3 h). 8 12 16 20 24 28 32 36 40 44 48 52 6600 6900 7200 7500 7800 A b u n d an ce Time (min) 1 2, DBE (IS) 3, BHT (in solvent) 1

Figure S3. GC-MS/FID spectrum of a liquid product from an experiment with Rh/C (400 °C, 3 h).

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Figure S4. GC×GC-FID chromatogram for product oil from an experiment with Ru/C (400 °C, 3 h). The large peak in the naphtalenes area is BHT, the antioxidant in THF. DBE is the internal standard.

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Figure S5. GCxGC chromatrograms for the blank (top) and regular reaction (bottom) with Pt/C. The larger peak in the naphthalene area is BHT, the stabiliser in THF (400°C, 3 h).

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Pt/ZrO2 Pt/TiO2

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8 12 16 20 24 28 32 36 40 44 48 52 7000 8000 9000 10000 11000 12000 A b u n d an ce Time (min) O 1 1 2 OH 2 3 3 4 4O O 5 5 6 OH 6 O 7 7 O 8 8 9, IS 10 10 O 11 11 O 12 12 13 13 14 14 OH 15 15 OH 16 16 OH 17 17 18, BHT

Figure S8. GC-MS/FID spectrum of a liquid product from an experiment with Pt/CeO2

(400 °C, 3 h). The exact position of substituents on the aromatic ring for 13, 14, 15, 16. 17, could not be established unequivocally by the GC-MS database

8 12 16 20 24 28 32 36 40 44 48 52 7000 7100 7200 7300 7400 7500 7600 7700 A b u n d an ce Time (min) O 1 1 OH 2 2 3 O 3 4, IS 5, BHT

Figure S9. GC-MS/FID spectrum of a liquid product from an experiment with Pt/ ZrO2

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Figure S10. GCxGC chromatogram for a liquid product from an experiment with Pt/TiO2

(400°C, 3 h).

Figure S11. GCxGC chromatogram for a liquid product from an experiment with Pt/ZrO2

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