Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2008 Hydrogenation catalysts from used nickel metal hydride batteries Mark R.StJ. Foreman, Christian H. Ekberg and Arvid Ödegaard Jensen Supporting material General Linalool and sodium borohydride were supplied by Aldrich. Nickel chloride was supplied by Merek. All other chemicals were supplied by Acros or Fisher. 3,3,5-Trimethylcyclohexanone was prepared by the hydrogenation of an ethanol solution of isophorone using 5% Pd on carbon as the catalyst, after two distillations this compound was used. The octene was formed in situ by the reduction of the octyne. 1H and 13 C-{ 1 H} NMR spectra were obtained using a Varian Unity 500 machine. GCMS results were obtained using helium as the carrier gas, an initial oven temperature of 70 o C, a solvent delay of 2 minutes, a heating rate of 5 o C min -1 , and a Hewlett-Packard G1800A GCD system (Electron impact ionization) which is fitted with a Supelco SP-2330 (15 m) column. Injections of 1 to 2 μl were made with the injection port operating in the splitless mode, and the mass of the analyte was approximately 90 ng. Metal analysis The metal content of aqueous solutions was determined by ICPOES (Inductively Coupled Plasma Optical Emission Spectroscopy) using a Thermo iCAP6500 machine using a pure argon plasma using nitric acid (1M) as the matrix for both samples and standards. Solid compounds were dissolved in nitric acid (1M) to enable their examination by ICPOES. Confirmation of the identities of the organic products. The ethanol solution of the product of linalool hydrogenation was filtered through a 0.45 μm syringe filter before being placed in a round bottomed flask. The majority of the ethanol was then removed using a rotary evaporator before part of the oily residue was dissolved in deuterated chloroform for 1 H and 13 C NMR spectroscopy. The 1 H NMR spectrum concurred with the hypothesis that the product would be 3,7-dimethyl-oct-6-en-3-ol, and the shifts in the 13 C NMR spectrum are a close match to those reported for 3,7-dimethyloct-6-en-3-ol. 1 The ethanol solution of the product of octyne hydrogenation was filtered through a 0.45 μm syringe filter. Part of this solution was placed in a NMR tube, after the addition of deuterated chloroform the mixture was examined by 1 H and 13 C NMR. By 1 H NMR the octene was found to be present as a single isomer rather than as a mixture of the cis and trans forms, while the shifts in the 13 C spectrum a close match to those reported for cis-oct-4-ene. 2 Table 1. 13 C NMR chemical shifts observed for the cis-oct-4-ene formed in the experiment. Identity of a carbon atom Chemical shift (ppm) Alkene 129.51 Allylic 28.98 Methylene 22.58 Methyl 13.41 1 Y. Imada, H. Iida, and T. Naota, J. Am. Chem. Soc., 2005, 127, 14544. 2 R.G.F. Giles, V.R. Lee Son and M.V. Sargent, Aust. J. Chem., 1990, 43, 777.