Bis(1,5-cyclooctadiene)nickel → Nickel

Under an inert atmosphere such as dry nitrogen or argon, a Ni(COD)2 solution is prepared by dissolving Ni(COD)2 (0.039 g) in toluene (2.79 g). A toluene solution, or other appropriate solvent solution, of the multidentate P-containing ligand or a ligand mixture comprising a multidentate P-containing ligand to be tested (0.230 mL of 0.062 mol total multidentate P-containing ligand/L of toluene) is treated with the Ni(COD)2 solution (0.320 mL) and thoroughly mixed to provide a catalyst solution with a zero-valent nickel/multidentate P-containing ligand molar ratio of about 1/1. A cis-2-pentenenitrile (cis-2PN)/ZnCl2 solution is prepared by dissolving ZnCl2 (0.017 g in 1.02 g cis-2PN). A sample of catalyst solution (0.100 mL) is treated with cis-2PN/ZnCl2 solution (0.025 mL); the resulting mixture has cis-2PN/nickel molar ratio of about 123 and a ZnCl2/nickel molar ratio of about 0.96/1. Over a period of 16 hours, the mixture is heated to about 50° C. and exposed to HCN vapor supplied from a reservoir of uninhibited, liquid HCN at ambient temperature (619 mm Hg or 82.5 kPa vapor pressure at 20° C). The reaction mixture is then cooled to ambient temperature, treated with acetonitrile (0.125 mL), and analyzed by gas chromatography for the amount of ADN, MGN, and 2-ethylsuccinonitrile produced, in order to calculate the percent conversion of 2PN to dinitriles.

1. additionP-containing ligand
2. additionthoroughly mixed

ORD record

ord-b407f420a8014cb7843e200adae55351

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08088943B2