Water → Oleic Acid
Reaction equation
[C:1]([O:20]C)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C(O)(=O)CC.S(=O)(=O)(O)O.O.CC1C(C)=C2C(CC[C@](CCC[C@H](CCC[C@H](CCCC(C)C)C)C)(C)O2)=C(C)C=1O>>[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]Participants
Procedure
Methyl oleate (100 grams, 0.338 moles), propionic acid (250.3 grams, 3.38 moles), concentrated sulfuric acid (12 grams, 0.12 moles), distilled water (100 grams, 5.56 moles), and Covi-Ox T-50 antioxidant (0.087 grams) are charged to a mantle-heated round bottom flask connected to a 30 cm. distillation column fitted with a take-off head. The bottom 8 cm. of the distillation column is packed with approximately 10 grams of XN1010 ion exchange resin (described in Example III) in pellet form. The distillation column is designed to allow vapor flow upward through the resin packing but liquid downflow is returned without passing through the resin packing. The flask is heated to between 105° C. and 110° C. for three hours. Methanol is taken off at the take-off head during reaction. Sample workup and analysis indicates a 99% yield of oleic acid.
Workup
- additionantioxidant (0.087 grams) are charged to a mantle-heated round bottom flask
- distillationdistillation column
- customfitted with a take-off head
- distillationof the distillation column
- distillationThe distillation column
- temperatureThe flask is heated to between 105° C. and 110° C. for three hours
- customduring reaction
Sources & evidence
- ORD record
- ord-5cfe92bdc0404f8c8777da1eae0762c4
- Source dataset
- uspto-grants-1980_01
- Patent number
- US04185027
Reaction notes
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