Carbon Dioxide → Diglycidyl ether

HRID 1979027Notes

Reaction equation

HRID 1979027 reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].[CH2:5]([CH:7]1[O:9][CH2:8]1)Cl.[OH-].[Na+].C(=O)=[O:13]>O>[CH2:2]([O:13][CH2:5][CH:7]1[O:9][CH2:8]1)[CH:1]1[O:4][CH2:3]1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 3776IsopropanolHCID 7835EpichlorohydrinHCID 14798Sodium Hydroxide2×

Product 1

HCID 16704Diglycidyl ether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent4×

Conditions

Temperature
55 °C

Procedure

A one liter flask was charged with: 75 g (grams) of the flaked reaction product of Example 6; 200 g of isopropyl alcohol; and 52.5 g of water to form a reaction mixture. The reaction mixture was heated to 55° C. After 10 minutes there was add 388.5 g of epichlorohydrin. The reaction mixture was reheated to 55° C. and then 30 g of a 20% solution of sodium hydroxide in water was added while maintaining a temperature of 55° C. The 55° C. temperature was held for another 30 minutes. Then there was added 90 g of 20% solution of sodium hydroxide in water. The reaction mixture was held at 55° C. for another hour, heated to 65° C. and held for 30 minutes and then transferred to a separatory funnel. The upper clear brown organic layer (145.6 g) was stirred with 150 g water and 50 g of dry ice. The aqueous layer was discarded and the organic layer washed a second time and then vacuum distilled to recover excess epichlorohydrin and 105 g of dark resin of the epoxidized product of Example 6. This epoxy resin has a weight per epoxy equivalent of 203.1 and 225.8. This compares with a weight per epoxy equivalent of 210 for EPON 1031. Viscosities and weight per epoxy equivalent (WPE) of the epoxy resin of this Example 8 as well as comparisons with other epoxy resins prepared from polyphenols are shown below in tables wherein this example may be referred to as EX8.

Workup

  1. customwas reheated to 55° C.
  2. temperaturewhile maintaining a temperature of 55° C
  3. waitThe reaction mixture was held at 55° C. for another hour
  4. temperatureheated to 65° C.
  5. waitheld for 30 minutes
  6. customtransferred to a separatory funnel
  7. washthe organic layer washed a second time
  8. distillationvacuum distilled
  9. customto recover excess epichlorohydrin and 105 g of dark resin of the epoxidized product of Example 6
  10. customViscosities and weight per epoxy equivalent (WPE) of the epoxy resin of this Example 8 as well as comparisons with other epoxy resins prepared from polyphenols

Sources & evidence

ORD record
ord-3274919268ef4a57aabaa4a92bcffb45
Source dataset
uspto-grants-2001_05
Patent number
US06239248B1

Reaction notes

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