Water → Trimethylolpropane Dilinoleate

HRID 1979657

Reaction equation

HRID 1979657 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2].[CH3:10][CH2:11]/[CH:12]=[CH:13]/[CH2:14]/[CH:15]=[CH:16]/[CH2:17]/[CH:18]=[CH:19]/[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28].[C:30](=[O:33])([O-])[O-:31].[Na+].[Na+].O>C1C=CC=CC=1>[C:27]([OH:28])(=[O:2])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]/[CH:19]=[CH:18]\[CH2:17]/[CH:16]=[CH:15]\[CH2:14][CH2:13][CH2:12][CH2:11][CH3:10].[C:30]([OH:31])(=[O:33])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]\[CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6510TrimethylolpropaneHCID 10340Sodium CarbonateHCID 5702742Linolenoyl chloride2×

Product 1

HCID 131713956Trimethylolpropane Dilinoleate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
180 fahrenheit

Procedure

308.02 grams (2.30 moles) of trimethylol propane (MW-134 g/mole) were dissolved in benzene and dried by refluxing and draining the azeotrope. The dry solution was added to 3 liters of diglyme dried with sodium ribbon. The solution was warmed with stirring in a 12 liter flask to 180° F. 682 grams (2.30 moles) of linolenoyl chloride (MW-296.45 g) was added dropwise over a period of three hours. The mixture was stirred overnight at 180° F. An additional 682 grams (2.30 moles) of linolenoyl chloride was added over a period of three hours and again heated at 180° F. overnight. After cooling, an excess of sodium carbonate in a water slurry was added to the reaction mixture to remove the hydrogen chloride. The mixture was then filtered. Approximately 250 ml of hexane were added to approximately 500 ml batches of the product, placed in a separatory funnel of appropriate size and washed three times with 200 ml of deionized water to remove any unreacted TMP and acid along with the diglyme and sodium carbonate. The hexane was removed by rotary evaporation, and the product was stored over molecular sieves.

Workup

  1. customdried
  2. temperatureby refluxing
  3. additionThe dry solution was added to 3 liters of diglyme
  4. dry with materialdried with sodium ribbon
  5. temperatureThe solution was warmed
  6. stirringThe mixture was stirred overnight at 180° F
  7. temperatureagain heated at 180° F. overnight
  8. temperatureAfter cooling
  9. customto remove the hydrogen chloride
  10. filtrationThe mixture was then filtered
  11. additionApproximately 250 ml of hexane were added to approximately 500 ml batches of the product
  12. customplaced in a separatory funnel of appropriate size
  13. washwashed three times with 200 ml of deionized water
  14. customto remove any unreacted TMP and acid along with the diglyme and sodium carbonate
  15. customThe hexane was removed by rotary evaporation

Sources & evidence

ORD record
ord-8266ada6f7bc408f984146efc35979fe
Source dataset
uspto-grants-1984_11
Patent number
US04482409

Linked notes

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