Phenol → 4-Hydroxybenzyl cyanide

HRID 2166940Notes

Reaction equation

HRID 2166940 reaction equation
[N:1]#[C:2]Cl.[CH:4]1[C:9]([OH:10])=[CH:8][CH:7]=[C:6]([CH3:11])[CH:5]=1.C1(O)C=CC=CC=1>>[OH:10][C:9]1[CH:4]=[CH:5][C:6]([CH2:11][C:2]#[N:1])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 2879P-CresolHCID 10477Cyanogen Chloride

Product 1

HCID 265484-Hydroxybenzyl cyanideYield 55%

Procedure

There were fed into the 1 meter heated reactor having a diameter of 55 mm and an average temperature of 720° C. via line 1 per hour 46.1 grams (0.75 mole) of gaseous cyanogen chloride and via line 2 313.6 grams (2.9 moles) of gaseous p-cresol as well as 1-2 liters of gaseous nitrogen. From the reactor 3 the nitrile containing gas entered into column 5 via the cooled line 4. The column 5 consisted of a "Sambay-Evaporator" having an inner surface area of 0.1 m and an erect packed column 20 cm long. At the foot of the column there were fed in per hour 2-3 liters of gaseous nitrogen, the temperature of the oil in the double jacket of the column is so regulated that the crude product condensing in the column and having a temperature of about 180° C. can be withdrawn via line 8, while at the head of the column 5 the waste gas having a temperature of about 160° C. is led via line 7 into the fractionating column 8. The column 8 has a length of 50 cm, a diameter of 2 cm and is filled with Raschig rings. At the foot of column 8 per hour there were led in about 2-3 liters of gaseous nitrogen. The cooling over the double jacket is so regulated that at the foot of the column there prevails a sump temperature of up to 120° C. and at the column head a temperature of 20°-40° C. The p-cresol condensing in the column 8 contains 5-6% phenol. Only after distillation separation of the phenol can be recovered p-cresol mixed with fresh p-cresol for replacement of material consumed be returned into the reactor 3. The residual gas leaving the column 8 is led via line 10 into the separator 11 at -30° C., as well as to the activated carbon filter (not shown) and thereupon led into the washing column 14 in which there takes place the washing of the residual gas with water. There are obtained in the column 5 per hour 91.6 grams of crude product from which there is obtained by distillation in the column 18 at 160° C./l Torr 54.9 grams of p-hydroxyphenylacetonitrile. This corresponds to a yield of 55% based on the cyanogen chloride employed.

Workup

  1. temperatureheated reactor
  2. customThe column 5 consisted of a "Sambay-Evaporator"
  3. customthe temperature of the oil in the double jacket of the column is so regulated that the crude product condensing in the column
  4. customa temperature of about 180° C.
  5. customcan be withdrawn via line 8, while at the head of the column 5 the waste gas
  6. customa temperature of about 160° C.
  7. additiona diameter of 2 cm and is filled with Raschig rings
  8. waitAt the foot of column 8 per hour there were led in about 2-3 liters of gaseous nitrogen
  9. customup to 120° C.
  10. customa temperature of 20°-40° C
  11. customThe p-cresol condensing in the column 8
  12. distillationOnly after distillation separation of the phenol
  13. customcan be recovered p-cresol
  14. additionmixed with fresh p-cresol for replacement of material
  15. customconsumed
  16. customThe residual gas leaving the column 8
  17. customis led via line 10 into the separator 11 at -30° C.
  18. filtrationas well as to the activated carbon filter (not
  19. washwashing of the residual gas with water
  20. customThere are obtained in the column 5 per hour 91.6 grams of crude product from which there

Sources & evidence

ORD record
ord-94412e9d5241452b9954ef4e72a45e2b
Source dataset
uspto-grants-1983_06
Patent number
US04390706

Reaction notes

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