Water → 1,7-Dimethylnaphthalene

HRID 1645465Notes

Reaction equation

HRID 1645465 reaction equation
O.[C:2]1([CH3:13])[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH:10]=[CH:11][CH3:12])=[CH:4][CH:3]=1>[Pt].CCCCCCC>[CH3:13][C:2]1[CH:7]=[CH:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:11]([CH3:12])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 540916801-Methyl-4-(pent-3-en-1-yl)benzene

Product 1

HCID 113261,7-Dimethylnaphthalene

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8900HeptaneSolvent

Procedure

Deionized water (500 parts) was added to H mordenite (15 parts) made by Tosoh Corporation, silica (270 parts), and alumina sol (21 parts) containing 70 weight percent alumina as a binder, and the mixture was thoroughly stirred at room temperature. After shaping of the slurry with an extruder, the shaped article was dried at 110° C. and then calcined at 350° C. for 3 hours to prepare a catalyst. After this catalyst was packed into a cylindrical stainless-steel cyclization reactor, 5-(p-tolyl)-2-pentene prepared by the preceding step was fed at a rate of 10 parts/hr while nitrogen was fed at a rate of 250 parts/min to complete a cyclization reaction at a temperature of 170° C. under normal pressure. The molar ratio of the diluent solvent to the raw material was 11. After the cyclization reaction, the reaction solution was fed to a cylindrical stainless-steel dehydrogenation reactor filled with 40 parts of 1%-platinum/activated charcoal catalyst (made by N.E. CHEMCAT). The reaction temperature was 280° C. During the dehydrogenation reaction, n-heptane as the diluent solvent was also fed at a rate of 20 parts/hr. After the reaction, the solution was fed to a glass distillation column under a reduced pressure of 19 kPa to recover n-heptane. The residual reaction solution after the removal of n-heptane was fed to a glass distillation column under a reduced pressure of 13 kPa to separate low-boiling-point components at a rate of 0.05 parts/hr and high-boiling-point components at a rate of 0.3 parts/hr and to isolate 9.4 parts of 1,7-DMN with a purity of 98% from a middle plate of the distillation column.

Workup

  1. additioncontaining 70 weight percent alumina as a binder
  2. customthe shaped article was dried at 110° C.
  3. customto prepare a catalyst
  4. customa cyclization reaction at a temperature of 170° C. under normal pressure
  5. customAfter the cyclization reaction
  6. customwas 280° C
  7. customAfter the reaction
  8. distillationthe solution was fed to a glass distillation column under a reduced pressure of 19 kPa
  9. customto recover n-heptane
  10. customThe residual reaction solution after the removal of n-heptane
  11. distillationwas fed to a glass distillation column under a reduced pressure of 13 kPa
  12. customto separate low-boiling-point components at a rate of 0.05 parts/hr and high-boiling-point components at a rate of 0.3 parts/hr

Sources & evidence

ORD record
ord-1be64e36878e4dbea7d461266ec4d195
Source dataset
uspto-grants-2012_02
Patent number
US08124825B2

Reaction notes

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