Glycidol → Dodecyl diglyceryl phosphate

HRID 648784Notes

Reaction equation

[CH2:1]1[O:3][CH:2]1[CH2:4][OH:5].P([O-])([O-])(OCCCCCCCCCCCC)=O.[P:23]([O-:44])([O:38][CH2:39][CH:40]([CH2:42][OH:43])[OH:41])([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:24]>>[P:23]([O:44][CH2:1][CH:2]([CH2:4][OH:5])[OH:3])([O:38][CH2:39][CH:40]([CH2:42][OH:43])[OH:41])([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[O:24]

Participants

Reactant 3

HCID 11164Glycidol

HCID 1550836Dodecylphosphate

HCID 20145834Dodecyl glyceryl phosphate

Product 1

HCID 20145828Dodecyl diglyceryl phosphate

Procedure

While keeping the reaction system at 60° C., 150 g of glycidol (oxirane value=683.7) was gradually added, followed by their reaction at 70° C. for 2 hours. The acid value of the reaction system was AV1=4.4, AV2=6.0, revealing that the reaction system contained about 4.5 mole % of unreacted monododecyl phosphate and about 8.1 mole % of the corresponding phosphoric diester, i.e., dodecyl glyceryl phosphate and about 87.4 mole % of the corresponding phosphoric triester, i.e., dodecyl diglyceryl phosphate were formed.

Workup

customat 60° C.
customfollowed by their reaction at 70° C. for 2 hours

Sources & evidence

ORD record: ord-9b27b00f78264b04a6344e032639d4a9
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04736051

Reaction notes

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