Phenol → Diphenyl carbonate

HRID 2225920Notes

Reaction equation

HRID 2225920 reaction equation
[C:1](=[O:11])([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[O:2][CH3:3].[C:12]1(O)[CH:17]=[CH:16]C=[CH:14][CH:13]=1>>[C:1](=[O:11])([O:2][C:3]1[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=1)[O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 996PhenolHCID 139482Carbonic acid, methyl phenyl ester

Product 1

HCID 7597Diphenyl carbonate

Procedure

A mixture of 75 g/h of methyl phenyl carbonate, 175 g/h of phenol and 3 g/h of octylstannonic acid was continuously fed into this reactor at the feeding point above the sieve-point column. At the same time, a gentle nitrogen stream of 2 [1.h-1 ] from the spiral tube evaporator was passed in the opposite direction to this starting material stream. After establishment of constant conditions, at the head of the apparatus, 195 g/h of a mixture of 2.2% by weight of methanol, 13.7% by weight of dimethyl carbonate and 84.1% by weight of phenol were continuously withdrawn, and at the foot of the column, 61 g/h of a mixture of 1.5% by weight of phenol, 0.9% by weight of methyl phenyl carbonate and 97.6% by weight of diphenyl carbonate were continuously withdrawn. This represented a space-time yield for the formation of diphenyl carbonate of 0.06 g/mlh, based on the reactor volume. 18.6% of the methyl phenyl carbonate used reacted with phenol, transesterifying to form diphenyl carbonate. The selectivity of the formation of diphenyl carbonate was >99.9%, that is no by-products could be detected.

Workup

  1. customwas continuously fed into this reactor at the feeding point above the sieve-point column
  2. customAt the same time, a gentle nitrogen stream of 2 [1.h-1 ] from the spiral tube evaporator
  3. additionAfter establishment of constant conditions, at the head of the apparatus, 195 g/h of a mixture of 2.2% by weight of methanol, 13.7% by weight of dimethyl carbonate and 84.1% by weight of phenol
  4. customwere continuously withdrawn
  5. additionat the foot of the column, 61 g/h of a mixture of 1.5% by weight of phenol, 0.9% by weight of methyl phenyl carbonate and 97.6% by weight of diphenyl carbonate
  6. customwere continuously withdrawn

Sources & evidence

ORD record
ord-d403d49b6939409ba49f0bd3ef8f9959
Source dataset
uspto-grants-1994_09
Patent number
US05344954

Reaction notes

Loading…