N,N'-(1,5-Naphthalenediyl)bis(ethyl carbamate) → Carbamic acid, ethyl ester

HRID 1065609

Reaction equation

HRID 1065609 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C:7]1[C:16]2[C:11](=[C:12]([NH:17][C:18](OCC)=[O:19])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)=[O:5])[CH3:2]>[Zn].O>[CH:14]1[CH:13]=[C:12]([N:17]=[C:18]=[O:19])[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([N:6]=[C:4]=[O:3])[C:16]=2[CH:15]=1.[NH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 1

HCID 4108140N,N'-(1,5-Naphthalenediyl)bis(ethyl carbamate)

Product 2

HCID 5641Carbamic acid, ethyl esterHCID 185031,5-Naphthalene diisocyanate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Conditions

Temperature
350 °C

Procedure

Via a powder metering device, 25 parts of 1,5-bis(ethoxycarbonylamino)naphthalene were fed at a rate of 450 liters per liter of reaction volume an hour into a tube reactor filled with zinc shavings and heated to 350° C. A pressure of 1 millibar to 3 millibars was maintained in the separating reactor. The escaping decomposition gases were fractionally condensed. In a first water-cooled vessel, 14 parts of 1,5-naphthalene diisocyanate (NDI) were obtained (80.5 theoretical percent relative to feed urethane). The melting point was 129° C. to 132° C.

Workup

  1. temperatureA pressure of 1 millibar to 3 millibars was maintained in the separating reactor
  2. customcondensed

Sources & evidence

ORD record
ord-5dd6e6f5471f42468b6912db14e0f564
Source dataset
uspto-grants-1982_05
Patent number
US04330479

Linked notes

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