Hydrochloric Acid → Oleic Acid

HRID 1758219Notes

Reaction equation

HRID 1758219 reaction equation
[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[OH-].[Na+].[BH4-].[Na+].Cl>C(O)C>[C:1]([OH:20])(=[O:19])[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][CH3:18].[C:1]([OH:20])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 445639Oleic AcidHCID 4311764Sodium borohydride

Product 2

HCID 5281Stearic AcidYield 42%HCID 445639Oleic AcidYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under nitrogen, 3.2 ml (10 mmol) oleic acid, 400 mg (10 mmol) sodium hydroxide, 1 g (25 mmol) sodium borohydride and 500 mg (0.9 mmol) cobalt (II) phthalocyanine are agitated in 80 ml ethanol for 93 hours at 20° C. The green reaction mixture is neutralized, cooling with ice, with 5N hydrochloric acid, and the blue precipitate is centrifuged which is washed with ethanol. The centrifugate collected is mixed with 50 ml 5N hydrochloric acid extraction is performed with benzene. The benzene phase is washed with water, dried with sodium sulfate and concentrated. The fractional crystallization of the ethanol residue yields 1.2 g (42%) stearic acid as well as 1.3 g (46%) not-yet-converted oleic acid.

Workup

  1. washis washed with ethanol
  2. customThe centrifugate collected
  3. additionis mixed with 50 ml 5N hydrochloric acid extraction
  4. washThe benzene phase is washed with water
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. customThe fractional crystallization of the ethanol residue

Sources & evidence

ORD record
ord-be9f4f40a6464b378353818d602d0693
Source dataset
uspto-grants-1983_02
Patent number
US04372893

Reaction notes

Loading…