N-vinyl-2-pyrrolidone → Isooctyl Acrylate N-vinyl-2-pyrrolidone

HRID 2396666Notes

Reaction equation

[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])(=[O:4])[CH:2]=[CH2:3].[CH:14]([N:16]1[CH2:20][CH2:19][CH2:18][C:17]1=[O:21])=[CH2:15].CCCCCCC>C(OCC)(=O)C>[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])(=[O:4])[CH:2]=[CH2:3].[CH:14]([N:16]1[CH2:20][CH2:19][CH2:18][C:17]1=[O:21])=[CH2:15]

Participants

Conditions

Temperature: 55 °C

Procedure

Isooctyl acrylate (54.9 Kg), N-vinyl-2-pyrrolidone (5.4 Kg), and ethyl acetate (93.6 Kg) were charged into a 75 gallon (285 liter) stainless steel reactor. The mixture was deoxygenated and heated to 55° C. After 5 minutes at 55° C., azobisisobutyronitrile (30 g) premixed in ethyl acetate (1 Kg) was charged to the reactor. Additional portions of azobisisobutyronitrile (30 g) premixed with ethyl acetate (1 Kg) were added 4 hours after the start of the reaction and again at 8 hours. The temperature was maintained at 55° C. throughout the reaction. The reaction was continued until complete. An antioxidant (61 g, IRGANOX™ 1010, Ciba-Geigy Corp.) and heptane (66.3 Kg) were added to the reactor and the contents mixed until homogeneous. The final copolymer had a measured inherent viscosity of 1.67 deciliter/g in ethyl acetate.

Workup

customThe mixture was deoxygenated
additionazobisisobutyronitrile (30 g) premixed in ethyl acetate (1 Kg)
additionwas charged to the reactor
additionAdditional portions of azobisisobutyronitrile (30 g) premixed with ethyl acetate (1 Kg)
additionwere added 4 hours
customafter the start of the reaction
waitagain at 8 hours
temperatureThe temperature was maintained at 55° C. throughout the reaction
additionthe contents mixed until homogeneous

Sources & evidence

ORD record: ord-865d5e54f02b4121bf5bc22c4d64359a
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05494680

Reaction notes

Loading…