Oxygen → Cyclododecanol

HRID 1744429Notes

Reaction equation

HRID 1744429 reaction equation
[CH2:1]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:13]N1[C:18](=O)[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].O=O>O.O.O.O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(O)(=O)C>[C:1]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:15]1([OH:24])[CH2:16][CH2:23][CH2:22][CH2:21][CH2:20][CH2:17][CH2:18][CH2:3][CH2:2][CH2:1][CH2:12]1

Participants

7

Reactant 3

HCID 977OxygenHCID 9268CyclododecaneHCID 10665N-Hydroxyphthalimide

Product 2

HCID 13246CyclododecanoneYield 7.3%HCID 15595CyclododecanolYield 13.1%

Reagents, catalysts & solvents 2

HCID 61372Cobalt(II) acetate tetrahydrateCatalystHCID 176Acetic AcidSolvent

Procedure

In a flask having an internal volume of 100 ml, 8.4 g (50 mmol) of cyclododecane, 4.52 g of acetic acid, 16.3 mg (0.1 mmol) of N-hydroxyphthalimide, 28.9 mg (0.1 mmol) of bis(acetylacetonato)manganese(II) dihydrate, and 2.0 mg (0.01 mmol) of cobalt(II) acetate tetrahydrate were placed, and an oxygen balloon was attached to the reactor. The liquid temperature was raised on an oil bath and was held at 100° C. The reaction was terminated by cooling 6 hours later. A reaction mixture was diluted with 60 g of acetic acid to thereby dissolve all of solid matters. The resulting solution was analyzed to find that a conversion from cyclododecane was 20.6% and a selectivity for dodecanedioic acid was 23.7%. In addition, cyclododecanone (selectivity: 7.3%) and cyclododecanol (selectivity: 13.1%) were by-produced.

Workup

  1. customIn a flask having
  2. temperatureThe liquid temperature was raised on an oil bath
  3. customwas held at 100° C
  4. customThe reaction was terminated
  5. temperatureby cooling 6 hours later
  6. additionA reaction mixture was diluted with 60 g of acetic acid
  7. dissolutionto thereby dissolve all of solid matters

Sources & evidence

ORD record
ord-cb86508fbfa6497bba763938d464c601
Source dataset
uspto-grants-2006_03
Patent number
US07015356B2

Reaction notes

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