Isopropanol → Eicosanoic Acid

HRID 2414700Notes

Reaction equation

HRID 2414700 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][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

4

Reactant 2

HCID 3776IsopropanolHCID 8215Docosanoic Acid

Product 2

HCID 10467Eicosanoic AcidHCID 11197Tetracosanoic Acid

Conditions

Temperature
50 °C

Procedure

In 1200 kg of isopropyl alcohol was dissolved 100 kg of behenic acid (Edenor C22-85R) by heating at 50° C. The solution was filtered through a 10 μm filter and cooled to 30° C. for recrystallization at a cooling rate of 3° C./hr. The crystals thus formed were collected by centrifugal filtration, washed under running isopropyl alcohol, and dried. The resulting crystals were found to have a silver behenate content of 96%, a lignoceric acid content of 2%, and an arachidic acid content of 2% as a result of GC-FID measurement on an esterified sample.

Workup

  1. filtrationThe solution was filtered through a 10 μm
  2. filtrationfilter
  3. temperaturecooled to 30° C. for recrystallization at a cooling rate of 3° C./hr
  4. customThe crystals thus formed
  5. filtrationwere collected by centrifugal filtration
  6. washwashed under running isopropyl alcohol
  7. customdried

Sources & evidence

ORD record
ord-65bf1bafcd7f4b818024395036acb07b
Source dataset
uspto-grants-2004_11
Patent number
US06814506B2

Reaction notes

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