Alumina → Cyclododecanol

HRID 1250039Notes

Reaction equation

HRID 1250039 reaction equation
[O:1]1[C:3]2[CH:4]=[CH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:2]1=2.[H][H].[O-2].[O-2].[O-2].[Al+3].[Al+3]>[Pd]>[CH:2]1([OH:1])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 9989226AluminaHCID 54352584MonoepoxycyclododecadieneHCID 178418361HCID 178418361, compound

Product 1

HCID 15595CyclododecanolYield 20%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Also, it is known that epoxidized cycloalkanes and/or epoxidized cycloalkenes can be produced by epoxidizing corresponding cycloalkenes with a high yield. If the epoxidized compounds can be converted to corresponding cycloalkanones and cycloalkanols with a high efficiency, the cycloalkanones and the cycloalkanols can be expected to be obtained at a high yield. However, only a small number of reports can be found on methods of converting an epoxidized cycloalkane and/or an epoxidized cycloalkene to a mixture of cycloalkanone with cycloalkanol. For example, J. Mol. Catal., Vol. 69, pages 69 to 103 (1991) discloses a method of hydrogenating a monoepoxycyclododecadiene with hydrogen in the presence of a catalyst comprising palladium carried on a carrier consisting of γ-alumina, under a hydrogen gas pressure of 1.3 MPa at a temperature of 90° C. In this method, cyclododecanol was produced with a yield of 20% or less and no cyclododecanone was produced. When a catalyst comprising palladium carried on a carrier consisting of titania or silica was used in place of the above-mentioned palladium catalyst carried on γ-alumina, the yield of cyclododecanol was low and unsatisfactory.

Workup

  1. customcan be produced
  2. customto be obtained at a high yield
  3. customat a temperature of 90° C

Sources & evidence

ORD record
ord-8965c465e8af40daa8c2bb28687f2b49
Source dataset
uspto-grants-2002_01
Patent number
US06335472B1

Reaction notes

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