Chn vario macro analyzer

All reagents and solvents were acquired from Sigma-Aldrich (Burlington, MA, USA) or Avantor Performance Materials Poland S.A (Gliwice, Poland). ¹H NMR and ¹³C NMR spectra were recorded on Bruker Avance spectrophotometers (300, 400 or 700 MHz) in DMSO-d6 using TMS as an internal standard. Elemental analyses were performed on a Vario MACRO CHN analyzer (ELEMENTAR Analysensysteme GmbH, Langenselbold, Germany). Melting points were determined on a Mel TEMP 1002D apparatus and are given uncorrected. All reactions were controlled by TLC chromatography.

NMR spectra were recorded on Bruker Avance III/400 or Bruker Avance III/700 (Karlsruhe, Germany) for 1H and 176.1 MHz or 100.6 MHz for 13 C (see Supplementary Materials). Chemical shifts were recorded relative to SiMe₄ (δ0.00) or solvent resonance (CDCl₃ δ7.26, CD3OD δ3.31). Multiplicities were given as: s (singlet); d (doublet); dd (double doublet); ddd (double doublet); t (triplet); dt (double triplet); and m (multiplet). The 77Se NMR spectra were recorded on Bruker Avance III/400 or Bruker Avance III/700 with diphenyl diselenide as an external standard. NMR spectra were carried out using the ACD/NMR Processor Academic Edition. Melting points were measured with a Büchi Tottoli SPM-20 heating unit (Büchi Labortechnik AG, Flawil, Switzerland) and were uncorrected. Elemental analyses were performed on a Vario MACRO CHN analyzer (Elementar Analysensysteme GmbH, Langensenbold, Germany). Optical rotations were measured in 10 mm cells with a polAAr 3000 polarimeter (Optical Activity Limited, Ramsey, United Kingdom). Column chromatography was performed using Merck 40-63D 60 Å silica gel (Merck, Darmstadt, Germany).

The elemental analyses of all streams were characterized by a vario MACRO CHN-analyzer from ‘Elementar Analysensysteme GmbH’. The water content of pyrolysis oil was determined by a gas chromatograph, type Agilent 7890A, with a TCD detector and a HP-INNOWAX column, 30 m×0.53 mm×1 µm. The water content of the oil fraction was determined by Karl-Fischer-titration with a Schott Titro Line KF-Titrator and a Hydranal titration reagent. The boiling range of the oil fractions was determined by a gaschromatograph, type Agilent 7890A, with an FID-detector and the Restek-column MXT-2887, 10 m×0.53 mm×2.65 µm. Density and viscosity were measured with a digital viscometer, SVM 3000, of Anton Paar GmbH. The content of biogenous carbon (¹⁴C) was determined by the external laboratory Beta Analytic Limited, SO/IEC 17025:2005 accredited, in Miami, FL, via acceleration mass spectrometry.