Acetonitrile → Caprolactam

HRID 2061896Notes

Reaction equation

HRID 2061896 reaction equation
[H][H].S.[C:4]1(=[O:11])[NH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[C:12](#N)C>C1COCC1>[CH3:12][CH:4]1[CH2:5][CH2:6][CH:7]([CH3:8])[O:11]1.[C:4]1(=[O:11])[NH:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 7768Caprolactam2×HCID 178528035HCID 178528035, compound

Product 2

HCID 7768CaprolactamHCID 138552,5-Dimethyltetrahydrofuran

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Prior to optimization of the initial H2/H2S atmosphere and the mol % catalyst of presulfided Pt (Pt—S/C) employed, a range of solvents is examined (Table 5). No formation of caprolactam is observed using acetonitrile (entry 1, Table 5) as solvent. The highest yield of caprolactam is achieved using THF (entry 2, Table 5). Use of 2,5-dimethyltetrahydrofuran (entry 3, Table 5) results in a tenfold reduction in the yield of caprolactam relative to use of THF as solvent (entry 3 vs. entry 2, Table 5).

Sources & evidence

ORD record
ord-087dcbe524b9493688bef85ca497372e
Source dataset
uspto-grants-2012_10
Patent number
US08283466B2

Reaction notes

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