Glycerol → Octadecanoic acid--propane-1,2,3-triol (1/3)

HRID 653999Notes

Reaction equation

HRID 653999 reaction equation
[CH3:1][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][C:18]([OH:20])=[O:19].[CH2:21]([OH:26])[CH:22]([OH:25])[CH2:23][OH:24].[OH:27][CH2:28][CH:29]([CH2:31][OH:32])[OH:30].OP(O)(O)=O>O>[C:18]([OH:20])(=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1].[OH:26][CH2:21][CH:22]([CH2:23][OH:24])[OH:25].[OH:27][CH2:28][CH:29]([CH2:31][OH:32])[OH:30].[OH:26][CH2:21][CH:22]([CH2:23][OH:24])[OH:25]

Participants

5

Reactant 3

HCID 753GlycerolHCID 1004Phosphoric AcidHCID 93066Glyceryl monostearate

Product 1

HCID 53445378Octadecanoic acid--propane-1,2,3-triol (1/3)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
140 °C

Procedure

1461 g of stearine (hydrogenated oleo stearine) and 1100 g of glycerine plus 6 g of Ca(OH)2 were heated under nitrogen blanket to 230°-240° C. and kept at this temperature for 2 hours. Then, to change the alkaline catalyst to the acidic catalyst, for safety reasons the batch was cooled down to 140° C. and 20 g of 25% H3PO4 premixed with 20 g of water was slowly added. Following this the batch was again slowly reheated with maximum vacuum of 26 inches and temperature of 240° C. without stopping the reaction. It was reacted for 8 hours until 220 g of total water was collected. The composition of polyglycerol was:

Workup

  1. additionwas slowly added
  2. customwas again slowly reheated with maximum vacuum of 26 inches and temperature of 240° C.
  3. customthe reaction
  4. customwas collected

Sources & evidence

ORD record
ord-4ec645d31ae84b11ac163857e699ba9c
Source dataset
uspto-grants-1992_07
Patent number
US05130060

Reaction notes

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