4,8-Cyclododecadien-1-one → Cyclododecanone

HRID 2355806Notes

Reaction equation

HRID 2355806 reaction equation
[C:1]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH:9]=[CH:8][CH2:7][CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.[H][H]>[Pd]>[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

Participants

4

Reactant 2

HCID 6011764,8-Cyclododecadien-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 13246Cyclododecanone

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a reactor battery consisting of a tubular reactor with liquid circuit and a postreactor, cyclododeca-4,8-dien-1-one was hydrogenated continuously (30 bar, temperatures 130°, each reactor in trickle mode, catalyst 0.2% Pd on alumina), which also comprised approx. 0.5% polyunsaturated C12-aldehydes. The entire amount of hydrogen (2.1 molar equivalents based on reactant, i.e. 5 mol % hydrogen excess) was introduced into the main reactor and transferred together with the product stream into the postreactor. Downstream of the postreactor, the residual gas was discharged as offgas. At a total catalyst hourly space velocity of 0.5 kg of dienone/liter of catalyst×h, the conversion was 99.8%, i.e. the reaction effluent still contained 0.2% of unconverted olefin. In a subsequent distillation, it was possible to obtain cyclododecanone in a purity of 99.4%; 0.2% of unsaturated cyclododecanone was undesired secondary constituent.

Workup

  1. customIn a reactor battery consisting of a tubular reactor with liquid circuit
  2. distillationIn a subsequent distillation, it

Sources & evidence

ORD record
ord-b1d439a4a7f94c458e9164f7774b2b82
Source dataset
uspto-grants-2010_07
Patent number
US07754925B2

Reaction notes

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