Formaldehyde → Cyclododecene, (E)-

HRID 636894

Reaction equation

HRID 636894 reaction equation
[CH:1]1=[CH:2][CH2:3][CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][CH:9]=[CH:10][CH2:11][CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C=O.C1CCCCCCCCCCC1>C(O)(=O)C>[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 9268CyclododecaneHCID 11776TriphenylphosphineHCID 86756482cis-1,5,9-Cyclododecatriene

Product 1

HCID 15164Cyclododecene, (E)-Yield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
145 °C

Procedure

A 70 ml autoclave equipped with a magnetic stirrer was charged with 40 g of trans-, trans-, cis-1,5,9-cyclododecatriene, 50 mg of RuCl3*H2O, 400 mg of triphenylphosphine, 0.5 g of 37% strength aqueous formaldehyde solution and 100 mg of acetic acid. The reactor was purged with nitrogen and hydrogen and then brought to a hydrogen pressure of 20 bar and heated up with stirring. At 115° C., the reactor pressure decreased noticeably and the internal temperature rose quickly to 140° C. Thereafter the reactor was constantly maintained at 20 bar and 145° C. by means of hydrogen. After about 2.5 hours the reactor was cooled down and decompressed. The effluent was found by GC to contain a yield of 97% of cyclododecene and 1.8% of cyclododecane. The remainder was cyclododecadiene.

Workup

  1. customA 70 ml autoclave equipped with a magnetic stirrer
  2. customThe reactor was purged with nitrogen and hydrogen
  3. temperatureheated up
  4. customAt 115° C.
  5. customrose quickly to 140° C
  6. temperatureAfter about 2.5 hours the reactor was cooled down

Sources & evidence

ORD record
ord-db63a81a123e443cb48b349494f99c26
Source dataset
uspto-grants-2001_02
Patent number
US06194624B1

Linked notes

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