Trimethylolpropane → HCID 86735820, compound

HRID 866298Notes

Reaction equation

HRID 866298 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].[CH2:25]([C:27]([CH2:32][OH:33])([CH2:30][OH:31])[CH2:28][CH3:29])[OH:26].[OH-].[Na+]>O>[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][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][CH3:22].[CH2:25]([C:27]([CH2:32][OH:33])([CH2:30][OH:31])[CH2:28][CH3:29])[OH:26]

Participants

5

Reactant 3

HCID 6510TrimethylolpropaneHCID 8215Docosanoic AcidHCID 14798Sodium Hydroxide

Product 1

HCID 86735820HCID 86735820, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
220 °C

Procedure

Into a two liter-flask equipped with a central stirrer, a thermometer and a vertical condenser fitted to a receptacle, were introduced 1440g (4.25 mols) of behenic acid and 219.5g (1.6 mol) of trimethylolpropane. The reaction medium was slowly heated, under nitrogen atmosphere, until the medium was completely melted and 1.4g of sodium hydroxide pastilles, dissolved in a minimum of water, were added. The reaction medium was gradually heated to a temperature which provoked distillation of the water in the medium, without causing distillation of the trimethylolpropane. The medium was then heated to 220° C and this temperature was maintained for about 4 hours until the acid number was about 4. After cooling to 90° C, the medium was decoloured by means of hydrogen peroxide (200 volumes). The temperature was maintained at 90° to 95° C for 30 minutes and the molten material was poured onto a stainless steel plate. After cooling, 1550g of trimethylolpropane tribehenate were obtained.

Workup

  1. customInto a two liter-flask equipped with a central stirrer
  2. customa thermometer and a vertical condenser fitted to a receptacle
  3. temperatureThe reaction medium was slowly heated, under nitrogen atmosphere, until the medium
  4. additionwere added
  5. temperatureThe reaction medium was gradually heated to a temperature which
  6. distillationdistillation of the water in the medium
  7. distillationdistillation of the trimethylolpropane
  8. temperaturethis temperature was maintained for about 4 hours until the acid number
  9. temperatureAfter cooling to 90° C
  10. temperatureThe temperature was maintained at 90° to 95° C for 30 minutes
  11. additionthe molten material was poured onto a stainless steel plate
  12. temperatureAfter cooling

Sources & evidence

ORD record
ord-2b050c7e986f4aad9800e8270a19abed
Source dataset
uspto-grants-1978_07
Patent number
US04098706

Reaction notes

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