Hydrochloric Acid → Ethyl 4-chlorobutyrate

Temperature

100 °C

51.7 kg (0.6 kmol) of gamma-butyrolactone (100 percent) was placed in an enamel pressure agitator. The closed system was heated to 100° C. with good agitation, and starting from 60° C. a total of about 26.5 kg (0.72 kmol) of HCl was pressed on. The temperature and pressure quickly rose, caused by the exothermia. The addition of HCl and heat output were regulated so that the reaction could be performed isothermally at 100° C. and isobarically at 11 bars of pressure. Addition was continued until no more HCl was absorbed (about 5 to 6 hours). Then it was cooled to 20° C. and the residual HCl was discharged. Then 62.3 kg (1.35 kmol) of ethanol was added to the reaction solution. Then 2 kg (0.055 kmol) of HCl was again pressed on. It was heated to 100° C. and kept at this temperature for 2 hours (pressure was 6 bars) and then cooled to 20 ° C. The solution was then mixed with 92 kg of toluene and made basic with 23 kg of aqueous NaOH (30 percent) (pH 8 to 8.5). The phases were separated and the organic phase was washed with 26 kg of water. The combined water phases were again extracted with 46 kg of toluene. The organic phase was distilled. Thus, toluene, ethanol and water were separated. 87 kg of crude gamma-chlorobutyric acid ethyl ester (content 88 percent) remained as still residue, which could be used directly in the following step. The yield was 85 percent, relative to the gamma-butyrolactone.

1. customstarting from 60° C.
2. temperatureheat output
3. customwere regulated so that the reaction
4. customcould be performed isothermally at 100° C. and isobarically at 11 bars of pressure
5. additionAddition
6. customwas absorbed (about 5 to 6 hours)
7. temperatureThen it was cooled to 20° C.
8. temperatureIt was heated to 100° C.
9. temperature(pressure was 6 bars) and then cooled to 20 ° C
10. customThe phases were separated
11. washthe organic phase was washed with 26 kg of water
12. extractionThe combined water phases were again extracted with 46 kg of toluene
13. distillationThe organic phase was distilled
14. customThus, toluene, ethanol and water were separated

ORD record

ord-f9a8918e796344f5b9a35c4e8696ca9f

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05087745