Stearic Acid → Cyclododeca-1,3,5-triene

HRID 1656849Notes

Reaction equation

HRID 1656849 reaction equation
[CH:1]1[CH2:12][CH2:11][CH:10]=[CH:9][CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3][CH:2]=1.C(O)(=O)CCCCCCCCCCCCCCCCC.[OH-].[K+]>O>[CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:1][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 5281Stearic Acid2×HCID 126681,5,9-Cyclododecatriene2×HCID 14797Potassium Hydroxide

Product 1

HCID 53421619Cyclododeca-1,3,5-triene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A 600 mL beaker was charged with 150 g deionized water, 100 g of 91% pure 1,5,9-cyclododecatriene and 5.0 g of stearic acid. The resulting mixture was heated to 75°-80° C. to melt stearic acid and was intensively mixed at this temperature using a high shear Tekmar agitator while adding sufficient 50% aq. KOH to raise the pH to 10.5-11.0. The emulsion was cooled to room temperature and allowed to stand overnight. (Note: density differences between bulk water and emulsified particles caused some separation overnight, but gentle mixing again gave a uniform emulsion). The final emulsion contained 39.2 percent 1,5,9-cyclododecatriene (I) by weight.

Workup

  1. additionA 600 mL beaker was charged with 150 g
  2. temperatureThe resulting mixture was heated to 75°-80° C.
  3. additionwas intensively mixed at this temperature
  4. temperatureto raise the pH to 10.5-11.0
  5. customsome separation overnight
  6. additiongentle mixing again
  7. customgave a uniform emulsion)

Sources & evidence

ORD record
ord-4641f6233658400fa8dd804992806993
Source dataset
uspto-grants-1993_10
Patent number
US05254761

Reaction notes

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