Naphthalene → 1-(1-Methylethyl)naphthalene

HRID 325521Notes

Reaction equation

HRID 325521 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.[CH2:11]=[CH:12][CH3:13]>P(=O)(O)(O)O>[CH:12]([C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1)([CH3:13])[CH3:11]

Participants

4

Reactant 2

HCID 931Naphthalene3×HCID 8252Propylene2×

Product 1

HCID 225351-(1-Methylethyl)naphthalene

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidCatalyst

Procedure

These and other objects and advantages of the invention by the instant process comprises (1) alkylating naphthalene with propylene in the presence of a phosphoric acid catalyst supported on SiO2, at a temperature of 150°-280° C. and a pressure of 5-30 atm. using a mol ratio of 1/5 to 1/20 mol propylene per 1 mol of starting naphthalene, until in the reaction 45 to 65% of the naphthalene has been isopropylated and then without separating off the unreacted naphthalene, (2) further treating the alkylation mixture by heating it in the presence of a phosphoric acid catalyst supported on SiO2 under an inert gas pressure of 5 to 30 atm. to a temperature of 180° to 280° C. until substantially no more β-isopropylnaphthalene is formed from the α-isopropylnaphthalene. There is thereby obtained an isomeric mixture consisting of 90-95% of the β-isopropylnaphthalene isomer. Pure β-isopropylnaphthalene can be recovered from this isomeric reaction product by distillation and crystallization.

Workup

  1. customsupported on SiO2, at a temperature of 150°-280° C.
  2. customwithout separating off the unreacted naphthalene, (2)
  3. additionfurther treating the alkylation mixture
  4. temperatureby heating it in the presence of a phosphoric acid catalyst
  5. customsupported on SiO2 under an inert gas pressure of 5 to 30 atm. to a temperature of 180° to 280° C.

Sources & evidence

ORD record
ord-3177add7b7ef409285e22e8220f615f3
Source dataset
uspto-grants-1984_04
Patent number
US04440957

Reaction notes

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