Adiponitrile → Ammonium adipate

HRID 1779879Notes

Reaction equation

HRID 1779879 reaction equation
C(#N)CCCCC#[N:7].C([CH2:11][CH2:12][CH2:13][CH2:14][C:15](N)=[O:16])#[N:10].C(N)(=O)CCCC[C:23]([NH2:25])=[O:24].C(CCCCC([O-])=O)#N.C([O-])(=O)CCCCC(N)=O.[C:47]([O-:56])(=[O:55])[CH2:48][CH2:49][CH2:50][CH2:51][C:52]([O-:54])=[O:53]>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[C:23]([O:24][C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH3:11])#[N:25].[C:47]([O-:56])(=[O:55])[CH2:48][CH2:49][CH2:50][CH2:51][C:52]([O-:54])=[O:53].[NH4+:7].[NH4+:10]

Participants

9

Reactant 6

HCID 8128AdiponitrileHCID 12364HexanediamideHCID 200164Adipate(2-)HCID 117685765-CyanovaleramideHCID 226233665-CyanovalerateHCID 25795652Adipamate

Product 2

HCID 167786Ammonium adipateHCID 22074301Cyanovalerate

Reagents, catalysts & solvents 1

HCID 62657Potassium Phosphate, TribasicSolvent

Procedure

A cellular residue containing 13.1 mg of dry weight of cells was suspended in 2 ml of a 52.3 mM solution of adiponitrile in 50 mM potassium phosphate buffer, pH 7. The reaction was carried out at 25° C., with shaking, and the kinetics were followed by sampling. 5-Cyanovaleramide, adipamide, 5-cyanovalerate, adipamate and adipate were determined on each sample by high performance liquid chromatography (HPLC). The results are collated in FIG. 1, which shows the curves of the yield (on the ordinate) of cyanovalerate (curve a) and ammonium adipate (curve b). The respective rates of formation of cyanovalerate and adipate were greater than 0.45 and equal to 0.15 U/mg of dry weight of cells (1 U is equal to 1 μmol of product formed per minute).

Workup

  1. additionA cellular residue containing 13.1 mg of dry weight of cells
  2. customwas carried out at 25° C.
  3. aliquotby sampling

Sources & evidence

ORD record
ord-79817992101245e986d98521822be195
Source dataset
uspto-grants-1997_05
Patent number
US05629190

Reaction notes

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