Ethylene Glycol → Dioctanoyl ethylene glycol

HRID 1770327Notes

Reaction equation

HRID 1770327 reaction equation
[C:1]([O:8][CH2:9][CH2:10][O:11][C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:19](Cl)(=O)[CH2:20]CCCCCC.[CH2:29](O)[CH2:30]O.N1C=CN=C1>>[C:1]([O:8][CH2:9][CH2:10][O:11][C:12](=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:29][CH3:30])(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:19][CH3:20]

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 795ImidazoleHCID 8124Octanoyl chlorideHCID 2275452-Hexanoyloxyethyl hexanoate

Product 1

HCID 3093Dioctanoyl ethylene glycol

Procedure

Ethylene glycol di-n-octanoate was prepared as described for ethylene glycol di-n-hexanoate (except that heating was conducted at 140°- 150° C.) from octanoyl chloride (483 ml, 2.83 mol), anhydrous ethylene glycol (78 ml, 1.40 mol) and imidazole (193 g, 2.84 mol). Obtained 381.3 g (86.7% purified yield) of clear, colorless, mobile oil (bp 145°°148° C./<1 mm Hg).

Workup

  1. customObtained
  2. custom381.3 g (86.7% purified yield) of clear, colorless, mobile oil (bp 145°°148° C./<1 mm Hg)

Sources & evidence

ORD record
ord-ce804b7228984de7b7ca8579e0c0194d
Source dataset
uspto-grants-1995_01
Patent number
US05386045

Reaction notes

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