Adipic Acid → Adipic Acid

HRID 381802Notes

Reaction equation

HRID 381802 reaction equation
[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].C1(=O)CCCCC1.C1(O)CCCCC1>C1CCCCC1>[C:6]([OH:8])(=[O:7])[CH2:5][CH2:4][CH3:3].[C:6]([OH:8])(=[O:7])[CH2:5][CH2:4][CH2:3][CH3:2].[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

7

Reactant 3

HCID 196Adipic Acid2×HCID 7966CyclohexanolHCID 7967Cyclohexanone

Product 3

HCID 196Adipic AcidHCID 264Butyric AcidHCID 7991Pentanoic Acid

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

In reaction 19, cyclohexane was oxidized to a 1:7.1:6.0 mixture of adipic acid, cyclohexanone and cyclohexanol after 5 hours (turnovers: 21 (acid), 149 (ketone), 126 (alcohol); ˜6 % total conversion). The crude adipic acid product was collected by filtration after cooling the reaction mixture. Analyses of the isolated adipic acid were performed using elemental analysis, mass spectrometry, infrared spectroscopy, and 1H/13C NMR with comparisons to an authentic adipic acid sample. All analytical results showed that the isolated adipic acid (crude, washed with o-dichlorobenzene, but not recrystallized) was >95 % pure. NMR analysis showed that glutaric acid was also produced (<5 %) along with much lower amounts of shorter chain acids such as formic acid, butyric acid, valeric acid, etc. Only trace amounts of ketone and alcohol (and no adipic acid) were observed when the catalyst is omitted or replaced with 3 equivalents of dpphen alone.

Workup

  1. filtrationThe crude adipic acid product was collected by filtration
  2. temperatureafter cooling the reaction mixture
  3. customAll analytical results
  4. washwashed with o-dichlorobenzene
  5. customnot recrystallized)

Sources & evidence

ORD record
ord-ac5e1625f33f433e88ecedb5fdb86297
Source dataset
uspto-grants-2001_10
Patent number
US06307100B1

Reaction notes

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