Phenol → 2-Octadecylphenol

HRID 257591

反応式

HRID 257591 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>>[CH2:25]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[OH:7])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8]

参加物

3

反応物 2

HCID 996PhenolHCID 82171-Octadecene

生成物 1

HCID 138479032-Octadecylphenol

反応条件

温度
70 °C

実験手順

This example is directed to the preparation of a typical alkylated phenol component using the process disclosed in U.S. Pat. No. 4,976,882 and alkyl phenol-sulfur condensates produced thereby. Octadecyl phenol was prepared 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 has 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 m 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.

後処理

  1. customby charging into a four-neck, 5-liter round bottom flask
  2. customequipped with a mechanical stirrer
  3. customA reflux condenser, a thermometer, an addition funnel, and a nitrogen inlet tube were attached to the flask
  4. additionwas added dropwise over a period of about one hour
  5. temperatureThe temperature was raised to 90° C
  6. temperaturemaintained at this temperature for four hours
  7. temperatureThe reaction mixture was then cooled to 50° C.
  8. filtrationfiltered
  9. customto remove the catalyst
  10. customThe excess phenol was removed by vacuum distillation
  11. customat 25° C.
  12. customat 40° C.
  13. customabsorption bands at 830 and 750 cm-1 m which

出典と根拠

ORDレコード
ord-b1d85e5906084f80be520a6d05a7c1b2
出典データセット
uspto-grants-1993_11
特許番号
US05262508

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