Ethyl levulinate → HCID 59356937, compound

Temperature

150 °C

To a 600-mL Hastelloy® C-276 autoclave reactor (Parr Model 2302 HC) equipped with a gas entrainment turbine impellor and electrical heating mantle was added 150.0 g (1.04 mol) ethyl levulinate, 192.6 g (2.18 mol) N,N-dimethylethylenediamine, and 7.5 g ESCAT® 142 5% Pd/C catalyst. The reactor was purged first with nitrogen and then hydrogen, and then pressurized with 50 psig (0.4 MPa) hydrogen and stirred at 600 rpm while heating the reaction mixture to 150° C. On reaching this reaction temperature, the reactor was further pressurized to 1000 psig (7.0 MPa) with hydrogen and maintained at this pressure by adding additional hydrogen as required for the duration of the reaction. After 6 hours at these conditions, the reactor was cooled and vented, and the liquid reaction mixture was recovered for product isolation. The crude mixture was filtered through a glass frit via aspirator vacuum to remove the catalyst followed by removal of byproduct ethanol and unreacted N,N-dimethylethylenediamine in vacuo. The remaining contents were fractionally distilled with a 20-cm Vigreaux column under high vacuum (˜0.05 mmHg) to give 136.5 g water-white product at 85° C. in 77% isolated yield. Product purity was >99% as determined by GC/MS (HP-6890 equipped with MSD).

1. customThe reactor was purged first with nitrogen
2. temperaturemaintained at this pressure
3. additionby adding additional hydrogen
4. customas required for the duration of the reaction
5. temperaturethe reactor was cooled
6. customthe liquid reaction mixture
7. customwas recovered for product isolation
8. filtrationThe crude mixture was filtered through a glass frit via aspirator vacuum
9. customto remove the catalyst
10. customfollowed by removal of byproduct ethanol and unreacted N,N-dimethylethylenediamine in vacuo
11. distillationThe remaining contents were fractionally distilled with a 20-cm Vigreaux column under high vacuum (˜0.05 mmHg)
12. customto give 136.5 g water-white product at 85° C. in 77%
13. customisolated
14. customyield
15. customProduct purity was >99% as determined by GC/MS (HP-6890 equipped with MSD)

ORD record

ord-e28884bc1c2442d2a17d5f974947fa9a

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08721770B2