Epichlorohydrin → Cyclohexane-1,2-dicarboxylic acid bis(oxiranylmethyl) ester

HRID 1288044Notes

Reaction equation

HRID 1288044 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Cl.[C:6]1(=[O:16])[O:11][C:9](=[O:10])[CH:8]2[CH2:12][CH2:13][CH2:14][CH2:15][CH:7]12.OP([O-])([O-])=O.[K+].[K+].[OH-:24].[Na+]>O>[CH2:1]([O:24][C:9](=[O:10])[CH:8]1[CH2:12][CH2:13][CH2:14][CH2:15][CH:7]1[C:6]([O:11][CH2:1][CH:3]1[O:5][CH2:4]1)=[O:16])[CH:3]1[O:5][CH2:4]1

Participants

6

Reactant 4

HCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 24450Potassium Phosphate, DibasicHCID 85689Hexahydrophthalic anhydride

Product 1

HCID 21660Cyclohexane-1,2-dicarboxylic acid bis(oxiranylmethyl) ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

4163 g of epichlorhydrin, 693 g of hexahydrophthalic acid anhydride and 105 g of distilled water were weighed into a 6-liter four-necked flask, equipped with a reflux condenser, gas inlet pipe and dropping funnel, and heated with stirring to 90°C. A gentle stream of nitrogen was passed over the reaction mixture. After 2.5 hours, 15 g of K2HPO4 (secondary o-potassium phosphate) were added and the mixture was kept for about another 4 hours at 90°C. Thereafter, the product had an acid number of 0. It was cooled to approximately 20°C, followed by the dropwise addition over a period of 1 to 2 hours of 882 g of 45% by weight of NaOH. The sump temperature should not exceed 30°C during the addition. A water jet vacuum was then applied, and water together with excess epichlorhydrin (substantially quantitative) was distilled off. After the sump temperature had reached 90°C and the vacuum settled at approximately 20 mm, the product was taken up with 1000 g of toluene and washed with water until salt-free.

Workup

  1. customequipped with a reflux condenser, gas inlet pipe
  2. temperatureheated
  3. customwas kept for about another 4 hours at 90°C
  4. temperatureIt was cooled to approximately 20°C
  5. additionThe sump temperature should not exceed 30°C during the addition
  6. distillationwater together with excess epichlorhydrin (substantially quantitative) was distilled off
  7. customhad reached 90°C
  8. washwashed with water until salt-free

Sources & evidence

ORD record
ord-6687facd41d747dea80ec275878d8357
Source dataset
uspto-grants-1976_10
Patent number
US03987070

Reaction notes

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