Hydrochloric Acid → Diglycidyl ether

HRID 1649461Notes

Reaction equation

HRID 1649461 reaction equation
[C:1]1([CH2:9][OH:10])([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:11]([CH:13]1[O:15][CH2:14]1)Cl.[OH-].[Na+].Cl>C1(C)C=CC=CC=1>[CH2:11]([O:10][CH2:9][CH:1]1[O:8][CH2:7]1)[CH:13]1[O:15][CH2:14]1.[C:1]1([CH2:9][OH:10])([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7835EpichlorohydrinHCID 14798Sodium HydroxideHCID 250594Cyclohexanedimethanol

Product 2

HCID 16704Diglycidyl etherHCID 250594Cyclohexanedimethanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a three-liter three-neck glass reaction flask, equipped with a thermometer, stirrer, condenser and dropping funnel were placed cyclohexane dimethanol, toluene and the catalyst. Epichlorohydrin was then added gradually through the dropping funnel to the mixture at such a rate that the temperature varied from 70° to 90° C., with external cooling being applied to the flask. Sodium hydroxide was then added which dehydrohalogenated the chlorohydrin intermediate and neutralized the formed hydrochloric acid. After removal of salt, the mixture was dried and filtered to yield pure diglycidyl ether of cyclohexane dimethanol. The weight per epoxide of the reaction product was 158 to 168, with a viscosity of 60 to 70 centipoise.

Workup

  1. customIn a three-liter three-neck glass reaction flask
  2. customequipped with a thermometer, stirrer, condenser
  3. customvaried from 70° to 90° C.
  4. temperaturewith external cooling
  5. customAfter removal of salt
  6. customthe mixture was dried
  7. filtrationfiltered

Sources & evidence

ORD record
ord-c385dcdd77d345d18cc9b10467f328cb
Source dataset
uspto-grants-1983_11
Patent number
US04417033

Reaction notes

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