Sulfuric Acid → Tolyldocosanoic acid
Reaktionsgleichung
[C:1]([OH:24])(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].S(=O)(=O)(O)O.[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:1]([OH:24])=[O:23]Komponenten
4
Versuchsvorschrift
Five-hundred grams molten erucic acid were slowly added to a mixture of 679 gms toluene and 723 gms concentrated sulfuric acid while maintaining the temperature below 10° C. Tolyldocosanoic acid (acid value 123) was obtained in 82% yield. Distilled tolyldocosanoic acid (108 gms), 400 mls acetic acid 9.8 gms Co(OAc)2.4H2O and 1.3 gms ZrO(OAc)2 were then heated at 105° C. and 350 psi O2 for six hours during which time the acid value increased from 127 to 207. The selectivity to the desired carboxyphenyldocosanoic acid was 64.4% at a tolyldocosanoic conversion of 53.7%.