3-Amino-1-propanol → N-(3-Hydroxypropyl)-2-propenamide

To a 250 mL, four-neck round bottom flask equipped with a mechanical stirrer, a thermometer, a 100 mL dropping fuel, and a nitrogen inlet/outlet, 30.0 g of 1-amino-3-propanol (0.4 mole), and 100 mL of acetonitrile were added. The mixture was cooled below 0° C. with an ice/water bath. To this solution, 18.1 g of freshly distilled acryloyl chloride (0.2 mole) in 50 mL of acetonitrile was added through the dropping funnel. The addition rate was controlled so that the reaction temperature was kept below 0° C. After the addition was finished and the agitation was turned off, the reaction solution separated into two liquid phases. The bottom layer viscous salt solution phase was discarded. 100 mL of deionized water was added to the top layer acetonitrile solution phase. After removing all acetonitrile by vacuum distillation, the aqueous solution was passed through a mixed bed ion-exchange column packed with 20 g of Dowex MR-3C resin. A total of 76 grams of eluate was collected. The final solution has the following properties: HPLC and FT-IR analysis indicates there is no ester formation; HPAA concentration: 7.2% (wt/wt); pH=5.6 at 25° C.; Conductivity=56.6 μS/cm at 25° C.; Viscosity=1.1 cPs at 25° C. The relative low yield of HPAA is due to the fact that HPAA is soluble in the salt phase. HPAA in the salt phase can be recovered by acetone extraction since HPAA is soluble in acetone, and the salt is insoluble.

1. customTo a 250 mL, four-neck round bottom flask equipped with a mechanical stirrer
2. additionwere added
3. temperatureThe mixture was cooled below 0° C. with an ice/water bath
4. customwas kept below 0° C
5. additionAfter the addition
6. customthe reaction solution separated into two liquid phases
7. addition100 mL of deionized water was added to the top layer acetonitrile solution phase
8. customAfter removing all acetonitrile
9. distillationby vacuum distillation
10. customA total of 76 grams of eluate was collected
11. customat 25° C.
12. customat 25° C.
13. customat 25° C
14. customHPAA in the salt phase can be recovered by acetone extraction since HPAA

ORD record

ord-4589845c9bbf401eba16cc74134d6b5a

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06464850B1