[CH2:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]#[C:10][CH2:11][CH3:12].CN1CCOCC1.C([O-])([O-])=O.[Ca+2]>CO.[Pd].[Zn]>[CH2:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH3:12]6212 g (34.8 moles) of dodec-9-yn-1-ol and 316 g of N-methylmorpholine are dissolved in 46 l of methanol in a 100 l glass flask, and 62 g of a catalyst (0.7% Pd and 3.1% of Zn on a CaCO3 carrier) are suspended in the solution. Thereafter, the stirred suspension is flushed with nitrogen, and hydrogenation is carried out at from 0° to 5° C. and under a hydrogen pressure of 0.1 bar above atmospheric pressure until the absorption of hydrogen is complete. The methanol and morpholine are stripped off to give 6,200 g of dodec-9-en-1-ol containing 96.6% of the cis compound and 2.1% of the trans compound.
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