Water → Caprolactam n-Hexylamine

HRID 1282900Notes

Reaction equation

HRID 1282900 reaction equation
[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:9]([NH2:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].O>>[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:9]([NH2:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 962WaterHCID 7768CaprolactamHCID 8102Hexylamine

Product 1

HCID 86737235Caprolactam n-Hexylamine

Conditions

Temperature
250 °C

Procedure

A 200-ml. pressure reactor was charged with 50 g. (0.442 mole) of ε-caprolactam (CL), 10 g. (0.099 mole) of n-hexylamine (HA) and 0.2 g. (0.011 mole) of water. The reactor was cooled in a dry ice-acetone bath, evacuatively purged twice with nitrogen, evacuated, and heated at 250°C. for 16 hours with the contents under autogenous pressure. The cooled product was a soft white solid. A 45-g. portion was extracted by centrifugation first with about 900 ml. of 1:1 acetone:water and secondly with acetone. The air-dried residue weighed 25.5 g., and could be readily crushed to a fine powder. Analysis showed 865 equivalents of amino end groups per 106 g., corresponding to a degree of polymerization (DP) of about 9. Differential scanning calorimetry (DSC) showed a major melting endotherm at 196°-198°C.

Workup

  1. additionpressure reactor was charged with 50 g
  2. temperatureThe reactor was cooled in a dry ice-acetone bath
  3. customevacuatively purged twice with nitrogen
  4. customevacuated
  5. extractionportion was extracted by centrifugation first with about 900 ml
  6. custom, and could be readily crushed to a fine powder
  7. custom, corresponding to a degree of polymerization (DP) of about 9
  8. customat 196°-198°C.

Sources & evidence

ORD record
ord-4da8cd3dcd274e2883e23369e90d4537
Source dataset
uspto-grants-1976_08
Patent number
US03972961

Reaction notes

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