Adipic Acid → Bis(2-hydroxyethyl) adipate

HRID 328312Notes

Reaction equation

HRID 328312 reaction equation
[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[CH2:11]1[O:13][CH2:12]1.[CH2:14]([C:18](C)=[O:19])C(C)C>>[OH:19][CH2:18][CH2:14][O:7][C:6](=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:10][CH2:12][CH2:11][OH:13])=[O:9]

Participants

4

Reactant 3

HCID 196Adipic AcidHCID 6354Ethylene OxideHCID 7909Methyl Isobutyl Ketone

Product 1

HCID 74340Bis(2-hydroxyethyl) adipateYield 60%

Procedure

Adipic acid (36.5g, 0.25 mole) and the catalyst of Example II (0.4g) in methyl isobutyl ketone (250 ml) were heated at 160° C and subsequently ethylene oxide (24.23g, 0.55 mole) was added; the temperature was kept at 160° C. After 60 minutes, the pressure dropped from 103 psi to 57 psi. After solvent evaporation, the crude product (60.4g) was distilled under vacuum; a light yellow material (35.0g) was obtained boiling at 202°-203° C at 1 mm pressure in 60.0% yield, having a refractive index of 1.4619 at 25° C. The infrared spectrum was consistent with that expected for the ester (3450 cm-1 (OH), 2970 cm-1 (CH2), 1730 cm-1 (C=O), and 1180 cm-1 (C-O)). Anal. Calcd. for C10H18O6 : C, 51.28; H, 7.69; O, 41.03, Found: C, 50.80; H, 7.76; Molecular weight by hydroxy number: Theory: 234. Found: 234.

Workup

  1. customwas kept at 160° C
  2. additionthe pressure dropped from 103 psi to 57 psi
  3. customAfter solvent evaporation
  4. distillationthe crude product (60.4g) was distilled under vacuum

Sources & evidence

ORD record
ord-4dc7485a8a8f4cbeb3d598739c20123c
Source dataset
uspto-grants-1977_04
Patent number
US04017429

Reaction notes

Loading…