Naphthalene → 1-Nitronaphthalene

HRID 2413054Notes

Reaction equation

HRID 2413054 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[N+:11]([O-])([OH:13])=[O:12]>O>[N+:11]([C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 931Naphthalene2×HCID 944Nitric Acid2×

Product 1

HCID 68491-Nitronaphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 2-liter resin flask equipped with a stirrer, thermometer, a dropping funnel, a N2 sparge tube and a condenser vented to a caustic scrubber was added 1025 g (8.0 moles) naphthalene. The reactor contents were heated until the naphthalene became molten, at which time agitation was started, and the heating was stopped. 680 ml nitric acid (72.5% concentration, 10.0 moles) was introduced over a period of 3 hours. During the first 40 minutes of addition time the temperature was gradually reduced to about 62° C. and for the remaining addition period the reaction temperature was maintained between 50° and 60° C. By using reduced pressure (ca. 25 mm Hg) water and excess nitric acid were distilled off at 60°-75° C. for about 1.25 hours, and residual water and HNO3 was driven off by sparging the molten reaction product with nitrogen gas while maintaining reduced pressure. During the 30 minutes sparging period the temperature was kept at 75°-80° C. The molten product (1408.5 g, 100% of theory) was removed from the reactor.

Workup

  1. customTo a 2-liter resin flask equipped with a stirrer
  2. customthermometer, a dropping funnel, a N2 sparge tube and a condenser
  3. additionDuring the first 40 minutes of addition time the temperature
  4. additionwas gradually reduced to about 62° C. and for the remaining addition period the reaction temperature
  5. temperaturewas maintained between 50° and 60° C
  6. distillationwere distilled off at 60°-75° C. for about 1.25 hours
  7. customby sparging the molten reaction product with nitrogen gas
  8. temperaturewhile maintaining reduced pressure
  9. customDuring the 30 minutes sparging period the temperature
  10. customwas kept at 75°-80° C
  11. customThe molten product (1408.5 g, 100% of theory) was removed from the reactor

Sources & evidence

ORD record
ord-1441c379cc4146f2ae4140d2a749cce5
Source dataset
uspto-grants-1985_01
Patent number
US04495372

Reaction notes

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