Ethylene Glycol → Ethylene glycol dipalmitate

HRID 511052Notes

Reaction equation

HRID 511052 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[C:5]([OH:22])(=O)[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][CH3:20].[C:23]([O-:28])(=O)[C:24]([O-])=O.[Sn+2]>O>[C:23]([O:3][CH2:2][CH2:1][O:4][C:5](=[O:22])[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][CH3:20])(=[O:28])[CH2:24][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH3:5]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 985Palmitic AcidHCID 13149Ethanedioic acid, tin(2+) salt (1:1)

Product 1

HCID 69347Ethylene glycol dipalmitate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

90 g ethylene glycol (Fluka), 571 g palmitic acid (Edenol C16 98-100, Cognis-Oleochemicals) and 0.3 g tin (II) oxalate Goldschmidt) were heated under nitrogen. The esterization reaction starts at approx. 170° C. with the formation of water. After 3 hrs the reaction water is drawn off again by applying a vacuum and the vacuum within 4 hrs reduced to approx. 15 mbar. The final temperature was 230° C. at an acid value <6 the reaction was ended. It was cooled to 90° C. and filtered. Yield 568 g, acid value=3.9, dew point 70.5° C.

Workup

  1. customThe esterization reaction
  2. customwas 230° C. at an acid value <6
  3. filtrationfiltered
  4. customYield 568 g, acid value=3.9, dew point 70.5° C.

Sources & evidence

ORD record
ord-25fbd75cfb81433abbb60ae18673195e
Source dataset
uspto-grants-2015_08
Patent number
US09096738B2

Reaction notes

Loading…