Trifluoroacetic acid → HCID 131717649, compound

To 22.8 g (0.2 mole) of trifluoroacetic acid stirred in an ice-cooled flask was added 102 grams (1.1 moles) of epichlorohydrin at such a rate as to maintain the reaction temperature at 60°-70° C. Excess epichlorohydrin was removed under reduced pressure (35 torr) to yield the initiator CF3CO2CH2CH(CH2Cl)OH product which contained some isomeric CF3CO2CH(CH2Cl)CH2OH. SnCl4 catalyst (3.1 g) was added. The temperature was held at 70°-75° C. while an additional 275 g epichlorohydrin was added over a 90-minute period. The reaction mixture was stirred an additional 16 hours at 70° C., stripped at 70° C. and 5 torr for two hours. The stripped, blocked polyepichlorohydrin intermediate was unblocked by reacting it with a mixture of 180 g methanol, 20 g water, and 20 g concentrated ammonium hydroxide, first at a temperature of 30° C. for 30 minutes and then at 65° C. for 90 minutes. The pH of the aqueous phase was neutral (about 7). The organic phase was washed twice with a solution of 180 g of methanol and 20 g of water, then stripped at 60° C. at 5 torr to yield the desired primary hydroxyl-terminated polyepichlorohydrin polyol, having a structure like that of formula III, supra, Scheme III, where R3 is --CH(CH2Cl)--. Proton nmr analysis at 100 MHz showed the presence of 19% primary and 81% secondary hydroxyl groups.

1. temperaturecooled flask
2. temperatureto maintain the reaction temperature at 60°-70° C
3. customExcess epichlorohydrin was removed under reduced pressure (35 torr)

ORD record

ord-10389e6b16724a4a9af978d8fb6935f7

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05164521