Cyclododecanone → Cyclododecanol

HRID 982921Notes

Reaction equation

HRID 982921 reaction equation
[O:1]1[CH:3]2[CH2:4][CH2:5][CH:6]=[CH:7][CH2:8][CH2:9][CH:10]=[CH:11][CH2:12][CH2:13][CH:2]12.[H][H].C1(=O)CCCCCCCCCCC1>>[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

4

Conditions

Temperature
70 °C

Procedure

In an SUS-made autoclave having an inner volume of 100 ml and equipped with a stirrer, 20 g (0.112 mol) of 1,2-epoxy-5,9-cyclododecadiene and 0.08 g of a 5 mass % Pt/C catalyst (50% hydrous product, produced by N.E. Chemcat Corporation; 0.0102 mmol as platinum atom) were added and after pressurizing to 5 MPa with hydrogen at room temperature, heated to a temperature of 70° C. Under the same pressure, the contents were heated with stirring until the hydrogen absorption did not occur. After the completion of reaction, the reaction solution was cooled to room temperature, the catalyst was removed by filtration and the resulting reaction solution was analyzed. The analysis of the reaction solution was performed by gas chromatography. As a result, 1,2-epoxy-5,9-cyclododecadiene was 100% consumed and epoxycyclododecane (hereinafter referred to as “ECD”) was produced in a yield of 99.6 mol %. Also, as by-products, cyclododecanone (hereinafter referred to as “CDON”) was produced in 0.04 mol %, cyclododecanol (hereinafter referred to as “CDOL”) was produced in 0.20 mol % and cyclododecane (hereinafter referred to as “CDAN”) was produced in 0.04 mol %.

Workup

  1. customequipped with a stirrer
  2. temperatureUnder the same pressure, the contents were heated
  3. customAfter the completion of reaction
  4. temperaturethe reaction solution was cooled to room temperature
  5. customthe catalyst was removed by filtration
  6. customthe resulting reaction solution
  7. customconsumed
  8. customwas produced in a yield of 99.6 mol %

Sources & evidence

ORD record
ord-9d7df6f7cf904544ad1ef4272f454f1c
Source dataset
uspto-grants-2005_03
Patent number
US06861563B2

Reaction notes

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