Isopropanol → Docosanoic Acid

HRID 1371250Notes

Reaction equation

HRID 1371250 reaction equation
[C:1]([OH:24])(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[CH:25](O)(C)[CH3:26]>>[C:1]([OH:24])(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:1]([OH:24])(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:25][CH3:26].[C:1]([OH:24])(=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 8215Docosanoic Acid

Product 3

HCID 8215Docosanoic AcidHCID 10467Eicosanoic AcidHCID 11197Tetracosanoic Acid

Conditions

Temperature
30 °C

Procedure

Behenic acid manufactured by Henkel Co. (trade name: Edenor C22-85R) in an amount of 100 kg was admixed with 1200 kg of isopropyl alcohol, and dissolved at 50° C. The mixture was filtrated through a 10 μm filter, and cooled to 30° C. to allow recrystallization. Cooling speed for the recrystallization was controlled to be 3° C./hour. The resulting crystal was subjected to centrifugal filtration, and washing was performed with 100 kg of isopropyl alcohol, followed by repeating the aforementioned recrystallization procedure twice additionally. Thereafter, the crystal was dried. Thus resulting crystal was esterified, and subjected to GC-FID analysis to give the results of the content of behenic acid being 96 mol %, lignoceric acid 2 mol % and arachidic acid 2 mol %. In addition, erucic acid was included at 0.001 mol %.

Workup

  1. dissolutiondissolved at 50° C
  2. filtrationThe mixture was filtrated through a 10 μm
  3. filtrationfilter
  4. customrecrystallization
  5. temperatureCooling speed
  6. customfor the recrystallization
  7. filtrationThe resulting crystal was subjected to centrifugal filtration
  8. washwashing
  9. customthe aforementioned recrystallization procedure twice additionally
  10. customThereafter, the crystal was dried
  11. customThus resulting crystal
  12. customto give the

Sources & evidence

ORD record
ord-20ed51f39d5d486786a0506c36e8ee28
Source dataset
uspto-grants-2007_01
Patent number
US07157217B2

Reaction notes

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