Hydrochloric Acid → Mandelic Acid
Reaction equation
[OH-].[Na+].[C:3]([O-:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[Na+].C([O-])(=O)C.[Na+].Cl>>[C:3]([OH:13])(=[O:12])[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5]Participants
Procedure
To the filtrate remaining after process A above was added 201 grams of 50% sodium hydroxide solution, for a pH of 12.9. The basic solution was extracted 3 times with toluene, for a total toluene addition of 325 grams. The toluene and (-)PEA were distilled off under vacuum, resulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams. The sodium mandelate/sodium acetate phase was neutralized with 305.4 grams HCl, giving a pH of about 0.8. This was extracted 4 times with MIBK, in a fashion similar to that above, for a total addition of 295.3 grams MIBK. 185 grams H2O was added to the MIBK, and the MIBK was distilled off with azeotropic distillation, returning 274.4 grams or 92.9% MIBK recovery. The mandelic acid recovered from this process, together with that recovered above, gave a total recovery of 299.44 grams mandelic acid, or an 89.5% return.
Workup
- extractionThe basic solution was extracted 3 times with toluene
- additionfor a total toluene addition of 325 grams
- distillationThe toluene and (-)PEA were distilled off under vacuum
- customresulting in a recovery of 303.6 grams (93.4%) of toluene, and L(-)PEA in about 260.2 grams
- customgiving a pH of about 0.8
- extractionThis was extracted 4 times with MIBK
- additionin a fashion similar to that above, for a total addition of 295.3 grams MIBK
- addition185 grams H2O was added to the MIBK
- distillationthe MIBK was distilled off with azeotropic distillation
- customThe mandelic acid recovered from this process
- customtogether with that recovered above,
Sources & evidence
- ORD record
- ord-c4eb471a971e4b0ca5c87640603a8feb
- Source dataset
- uspto-grants-1991_01
- Patent number
- US04983771
Reaction notes
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