Phenol → Phenol

HRID 1701663Notes

Reaction equation

HRID 1701663 reaction equation
[C:1](Cl)(=[O:3])[NH2:2].[C:5]1([OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>ClC1C=CC=CC=1>[CH3:5][N:2]=[C:1]=[O:3].[C:5]1([OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:5]1([O:11][C:1](=[O:3])[NH2:2])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 996Phenol2×HCID 68048Carbamic chloride

Product 3

HCID 996PhenolHCID 12228Methyl IsocyanateHCID 69322Phenyl carbamate

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Example 2 is modified to the effect that the N-methyl-carbamic acid chloride solution described in Example 2 as solution 302 is freed by distillation from free methylisocyanate 411 prior to the reaction with phenol, so that 523 g per hour of a 50% by weight solution of carbamic acid chloride in chlorobenzene, corresponding to 2.8 mol of carbamic acid chloride, are produced in the side stream 404 and 1495 g per hour of pure chlorobenzene are produced in the sump 403. The concentrated carbamic acid chloride solution 404 was mixed with 400 g of a circulated 80% by weight solution 405 of phenol in chlorobenzene, corresponding to 3.4 mol of phenol, and was converted into the carbamic acid aryl ester solution 406 or 106 to be split up with separation of hydrogen chloride 412. 172 g of a 90% by weight chlorobenzolic methyl isocyanate solution 108 or 408 and 664 g of a 50% by weight chlorobenzolic phenol solution 107 or 407 containing a further 1.9% by weight of unmodified carbamic acid phenyl ester are obtained per hour during the decomposition of this solution 106 or 406. The methyl-isocyanate solution 108 or 408 is introduced into the upper section of the distillation column D and there separated into pure product 411 and solvent in 404 and 403 respectively. A total of 222 g per hour, corresponding to a 97% yield of methyl-isocyanate, are obtained. The phenol solution 107 or 407 is concentrated in a separate distillation column by distilling off pure chlorobenzene 409 to an 80% by weight phenol content and fed back again into the phenol cycle 405. The chlorobenzene 409 produced in the process is fed back to the beginning of the process.

Workup

  1. customare produced in the sump 403
  2. customto be split up with separation of hydrogen chloride 412

Sources & evidence

ORD record
ord-c16664ba5c8f4e14be43a56bb70c88ef
Source dataset
uspto-grants-1980_03
Patent number
US04195031

Reaction notes

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