Ethylene Glycol → Polyethylene glycol monocaprylate

HRID 1709719Notes

Reaction equation

HRID 1709719 reaction equation
[C:1](Cl)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:11]([OH:14])[CH2:12][OH:13].N1C=CC=CC=1>>[C:1]([O:13][CH2:12][CH2:11][OH:14])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 1049PyridineHCID 8124Octanoyl chloride

Product 1

HCID 170609Polyethylene glycol monocaprylateYield 79.5%

Procedure

Capryloyl chloride (0.602 mol; 98 g) was dropwise added during 1.5 hour into a mixture of ethylene glycol (3 mol; 186 g) and pyridine (0.6 mol; 47.4 g). The mixture was further stirred for 2 hours at laboratory temperature, allowed to stand overnight, and threetimes extracted with benzene (100+50+25 ml). The benzene extract was shaken with a 10% aqueous solution of NaHCO3 (2×30 ml) and water and benzene was evaporated in a rotation evaporator. Distillation of the residue gave 4 raw fractions with purity 79.9 to 97.9% at the overall yield of 2-hydroxyethyl caprylate 79.5%. Further procedure was carried out according to example 1.

Workup

  1. waitto stand overnight
  2. extractionthreetimes extracted with benzene (100+50+25 ml)
  3. extractionThe benzene extract
  4. stirringwas shaken with a 10% aqueous solution of NaHCO3 (2×30 ml) and water and benzene
  5. customwas evaporated in a rotation evaporator
  6. distillationDistillation of the residue

Sources & evidence

ORD record
ord-698a17e1e02449d6a64851869f8dec74
Source dataset
uspto-grants-1990_08
Patent number
US04950733

Reaction notes

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