Naphthalene → 1,2-Didecylnaphthalene

HRID 440184Notes

Reaction equation

HRID 440184 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][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CCCCCCC>[CH2:11]([C:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[CH:6]=[CH:7][CH:8]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[CH2:11]([C:7]1[CH:8]=[CH:9][C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[C:6]=1[CH2:9][CH2:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 931NaphthaleneHCID 133811-Decene

Product 2

HCID 45267421-DecylnaphthaleneYield 40%HCID 224108311,2-DidecylnaphthaleneYield 57.3%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of naphthalene (16.3 g, 0.127 mole) in 25 ml of heptane was heated to 80° C. in the presence of 3 g of the catalyst. 1-decene, 14.9 g (0.106 mole), was added quickly. The reaction was stirred at 80° C. for 8 hours. The catalyst was removed by filtration and the excess naphthalene removed by rotary evaporation. The product was fractionated to give 11.5 g (40% yield) of decylnaphthalene, and 12.4 g (57.3% yield) of didecylnaphthalene. The didecylnaphthalene has KV: 9.9 cS@100° C.; 97 cS@40° C.; VI 87.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe excess naphthalene removed by rotary evaporation

Sources & evidence

ORD record
ord-17a4eaf52a1e4ad486584959ec15e61c
Source dataset
uspto-grants-1996_05
Patent number
US05516954

Reaction notes

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