Methanol → Methyl behenate

HRID 2395919

Reaction equation

HRID 2395919 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]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[CH3:25]O.C[O-].[Na+]>OCC(CO)O>[CH3:25][O:23][C:1](=[O:24])[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]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 5281116Erucic Acid2×HCID 10942334Sodium Methoxide

Product 1

HCID 13584Methyl behenate

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent3×

Procedure

Behenic methyl esters are made from hydrogenated high erucic acid rapeseed oil. About 870 grams of hydrogenated high erucic acid rapeseed oil, about 174 grams of methanol, and about 12.2 grams of sodium methoxide solution (25% in methanol) are added to a spherical 3-liter glass reactor. The reactor has a heating mantle, thermometer, temperature controller, reflux condenser, variable speed agitator, vacuum take-off, and bottom outlet. The mixture is reacted at about 65° C. for approximately 1.5 hours,while refluxing the methanol. The agitation is stopped, and the glycerin isallowed to settle for about 30 minutes. The glycerin settles to the bottom of the reactor, and is removed through the bottom outlet. About 30 additional grams of methanol, and about 5.2 grams of sodium methoxide solution (25% in methanol) are added to the glass reactor, and the mixtureis reacted at about 65° C. for about 30 minutes. The agitation is stopped, the glycerin is settled for about 30 minutes, and removed throughthe bottom outlet. About 100 grams of water are added to the mixture, stirred, allowed to settle, and removed through the bottom outlet. The water-washing procedure is repeated two more times. The reflux condenser is removed, and vacuum is broken, and a fractionation column is added to the reactor. The reactor is heated to about 170°-200° C. under a vacuum of about 0.3-1.0 mm Hg. Approximately 50% of the first material to evaporate from the column is collected and discarded. The next40% (approximately) of the material to evaporate from the column is collected as product. This product is approximately 92% by weight methyl behenate.

Workup

  1. temperaturethermometer, temperature controller, reflux condenser
  2. customThe mixture is reacted at about 65° C. for approximately 1.5 hours
  3. customis removed through the bottom outlet
  4. additionAbout 30 additional grams of methanol, and about 5.2 grams of sodium methoxide solution (25% in methanol) are added to the glass reactor
  5. customthe mixtureis reacted at about 65° C. for about 30 minutes
  6. customremoved throughthe bottom outlet
  7. additionAbout 100 grams of water are added to the mixture
  8. customremoved through the bottom outlet
  9. washThe water-washing procedure
  10. customThe reflux condenser is removed
  11. additiona fractionation column is added to the reactor
  12. temperatureThe reactor is heated to about 170°-200° C. under a vacuum of about 0.3-1.0 mm Hg
  13. customApproximately 50% of the first material to evaporate from the column
  14. customis collected
  15. customThe next40% (approximately) of the material to evaporate from the column
  16. customis collected as product

Sources & evidence

ORD record
ord-745b9934b82e46f481f06537627e54f4
Source dataset
uspto-grants-1996_02
Patent number
US05490995

Linked notes

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