Calcium Acetate → Acrylamide

HRID 1181166Notes

Reaction equation

HRID 1181166 reaction equation
C([O-])(=[O:3])C.[Ca+2].C([O-])(=[O:8])C.[C:10](#[N:13])[CH:11]=[CH2:12].[C:14](#[N:18])[C:15]([CH3:17])=[CH2:16].[OH:19][CH:20]([CH2:24][CH3:25])[CH2:21][C:22]#[N:23]>O>[C:10]([NH2:13])(=[O:3])[CH:11]=[CH2:12].[C:14]([NH2:18])(=[O:8])[C:15]([CH3:17])=[CH2:16].[OH:19][CH:20]([CH2:24][CH3:25])[CH2:21][C:22]([NH2:23])=[O:3]

Participants

8

Reactant 4

HCID 6116Calcium AcetateHCID 7855AcrylonitrileHCID 31368MethacrylonitrileHCID 98554543-Hydroxypentanenitrile

Product 3

HCID 6579AcrylamideHCID 6595MethacrylamideHCID 149797283-Hydroxypentanamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At the completion of the reaction (100% conversion of nitrile), the product mixture was decanted from the biocatalyst beads, and additional distilled, deionized water, 0.2 mL of 0.20 M calcium acetate buffer (pH 7.0, 2.0 mM final calcium ion concentration in reaction mixture) and 10, 20, 40 or 60 mmol of acrylonitrile, methacrylonitrile, or 3-hydroxy-valeronitrile mixed with the reaction heel (immobilized-cell catalyst and remaining product mixture from the first reaction) at 25° C. or 35° C. At the completion of the second reaction, the product mixture was decanted and a third reaction performed as before. The reaction time, product yield for acrylamide, methacrylamide, or 3-hydroxyvaleramide, and the percent recovered biocatalyst activity for each recycle reaction is listed in Table 11 below.

Workup

  1. customthe product mixture was decanted from the biocatalyst beads, and additional distilled
  2. additionmixed with the reaction heel (immobilized-cell catalyst
  3. customfrom the first reaction) at 25° C.
  4. custom35° C
  5. customAt the completion of the second reaction
  6. customthe product mixture was decanted
  7. customa third reaction

Sources & evidence

ORD record
ord-602acb37ef65485f88b90945e0e6b6ea
Source dataset
uspto-grants-2007_10
Patent number
US07285406B2

Reaction notes

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