Ethylene Glycol → Epichlorohydrin

HRID 863616Notes

Reaction equation

HRID 863616 reaction equation
C(O)CO.[CH2:5]([CH:7]1[O:9][CH2:8]1)[Cl:6].B(F)(F)F.C(O)CO>O>[CH2:5]([CH:7]1[O:9][CH2:8]1)[Cl:6].[CH2:5]([Cl:6])/[CH:7]=[CH:8]\[OH:9]

Participants

6

Reactant 3

HCID 174Ethylene Glycol2×HCID 7835Epichlorohydrin2×HCID 88614575BF3 ethylene glycol

Product 2

HCID 7835EpichlorohydrinHCID 15676292(Z)-3-chloroprop-1-en-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

Epichlorohydrin (ECH) was polymerized in bulk in the presence of ethylene glycol as an initiator and a BF3 /ethylene glycol complex as a catalyst. The reaction was conducted in a 2-liter, three-necked flask fitted with a mechanical stirrer, funnel, condenser and thermometer. The reaction was conducted while maintaining the flask in a water bath at 20° C. Epichlorohydrin was slowly added to ethylene glycol containing a complex of BF3 /ethylene glycol at rate of 15 to 40 grams per hour. Following the addition of epichlorohydrin, the reaction mass was held in the water bath at 20° C. for an additional 4 hours. At the end of the reaction period, 300 mL of dionized water was added into the reaction mixture with stirring to inactivate the catalyst. The organic phase in the flask was then separated from the aqueous phase and the organic phase was dried at 40° C. under vacuum for one day. The polymerization temperature was controlled by adding the epichlorohydrin to the bulk ethylene glycol containing the catalyst over a period of time in order to obtain a linear polyepichlorohydrin (PECH) diol having a relatively narrow molecular weight distribution with a polydispersity below about 1.5. The molecular weight of the PECH diol was determined by gel permeation chromatography (GPC). The weight ratios of ECH to glycol, the rate of ECH addition and the temperature of the reaction were varied to demonstrate the effect of these variables on the molecular weight of the resulting PECH. The results are listed in Table 1 below.

Workup

  1. customfitted with a mechanical stirrer, funnel, condenser
  2. additionwas added into the reaction mixture
  3. customThe organic phase in the flask was then separated from the aqueous phase
  4. customthe organic phase was dried at 40° C. under vacuum for one day
  5. additionby adding the epichlorohydrin to the bulk ethylene glycol containing the catalyst over a period of time in order

Sources & evidence

ORD record
ord-095d2681ef474a8ea6d9d06f048fd231
Source dataset
uspto-grants-1998_02
Patent number
US05721322

Reaction notes

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