Reaktion #413632

Reaktionsgleichung

phenol

1-octadecene

→

octadecyl phenol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeby charging into a four-neck, 5-liter round-bottom flask
2. 2
   Sonstigeequipped with a mechanical stirrer
3. 3
   SonstigeA reflux condenser, a thermometer, an addition funnel, and a nitrogen inlet tube were attached to the flask
4. 4
   workup.ADDITIONwas added dropwise over a period of about one hour
5. 5
   TemperaturThe temperature was raised to 90° C.
6. 6
   Temperaturmaintained at this temperature for four hours
7. 7
   TemperaturThe reaction mixture was then cooled to 50° C.
8. 8
   Filtrationfiltered
9. 9
   Sonstigeto remove the catalyst
10. 10
    SonstigeThe excess phenol was removed by vacuum distillation
11. 11
    Sonstigeat 25° C.
12. 12
    Sonstigeat 40° C.
13. 13
    Sonstigeabsorption bands at 830 and 750 cm-1, which

Vorschrift

As an example of the preparation of a typical alkyl phenol component used to produce alkyl phenolformaldehyde condensates, as disclosed in Ser. No. 107,457, filed Oct. 8, 1987, octadecyl phenol was prepared without the cosolvent of the instant invention by charging into a four-neck, 5-liter round-bottom flask equipped with a mechanical stirrer, 933 grams of phenol (9.93 moles) and 286 grams of Amberlyst 15 catalyst. A reflux condenser, a thermometer, an addition funnel, and a nitrogen inlet tube were attached to the flask and the mixture was heated to 70° C. With stirring under a blanket of nitrogen, 834 grams (3.31 moles) of 1-octadecene was added dropwise over a period of about one hour. The temperature was raised to 90° C. and maintained at this temperature for four hours. The reaction mixture was then cooled to 50° C. and filtered to remove the catalyst. The excess phenol was removed by vacuum distillation. The yield was 1,008 grams, or 88%. The product had a refractive index of 1.4859 at 25° C., a viscosity of 38.0 cP at 40° C., and a hydroxyl number of 144 mg KOH/g. The infrared spectrum of the product showed absorption bands at 830 and 750 cm-1, which are characteristic of alkyl phenols. The aromatic substitution pattern was determined by 13C-NMR spectroscopy and showed that the ortho to para ratio was 2.0:1.0. The alkyl substitution pattern was determined by 1H-NMR spectroscopy and showed that the product consisted of 50 mole % 2-substituted alkylate and 50 mole %≥3-substituted alkylate.

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