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

HRID 654000Notes

Reaction equation

[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].[OH:21][CH2:22][CH:23]([CH2:25][OH:26])[OH:24].[OH:27][CH2:28][CH:29]([CH2:31][OH:32])[OH:30].OP(O)(O)=O>O>[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].[OH:21][CH2:22][CH:23]([CH2:25][OH:26])[OH:24].[OH:27][CH2:28][CH:29]([CH2:31][OH:32])[OH:30].[OH:21][CH2:22][CH:23]([CH2:25][OH:26])[OH:24]

Participants

Conditions

Temperature: 100 °C

Procedure

1790 g of 90% glycerine monostearate premixed with 920 g of glycerine were heated under nitrogen blanket up to 100° C. The catalyst was prepared by dispersing 8 g of Ca(OH)2 (dry) with 52 g of water and then 30 g of 25% H3PO4 premixed with 60 g of water was slowly added into it while stirring for 30 minutes. Such prepared catalyst mixture was added at 100° C. to glycerine monoglyceride. This reaction mixture was then heated up and nitrogen replaced with slow application of vacuum. At 120° C. and vacuum of 20 inches the first water started to come over. In 3 hours time 230° C. was reached at 23 inches of maximum vacuum and 160 g of water was removed. This condition was kept for another 3 hours and 310 g of total water was collected.

Workup

customThe catalyst was prepared
additionwas slowly added into it
temperatureThis reaction mixture was then heated up
customAt 120° C.
customwas removed
waitThis condition was kept for another 3 hours
custom310 g of total water was collected

Sources & evidence

ORD record: ord-f4cb6e5e913548a3a03b3b09976fb0d8
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05130060

Reaction notes

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