Azobisisobutyronitrile → alpha-Chloro-o-xylene

HRID 842330Notes

Reaction equation

HRID 842330 reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.ClCl.[Cl:15][CH2:16][C:17]1[C:18]([CH2:23]Cl)=[CH:19][CH:20]=[CH:21][CH:22]=1>CC1C=CC=CC=1C>[Cl:15][CH2:16][C:17]1[C:18]([CH3:23])=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Conditions

Temperature
90 °C

Procedure

A condenser tube, a stirring blade and a thermometer were set to a 500-mL-volume four-necked flask and in this reaction device, 86.9 g (0.82 mol) of o-xylene and 2.17 g (0.013 mol) of AIBN were placed to prepare a mixed solution. After the reaction device was heated to 90° C., chlorine gas was blown therein at a flow rate of 0.378 mol/hr, and the reaction was carried out for 4 hour with stirring. After completion of the reaction, a part of the reaction mixture was sampled. Then, the components of reaction mixture were analyzed by GC. As a result, the conversion of raw material o-xylene was 99.7%, the yield of α,α′-dichloro-o-xylene was 50.5% (based on o-xylene), and the selectivity of α,α′-dichloro-o-xylene was 50.7%. At this time, α-chloro-o-xylene was obtained in a yield of 30% (based on o-xylene), α,α-dichloro-o-xylene was obtained in a yield of 7%, and α,α,α′-trichloro-o-xylene was obtained in a yield of 9%.

Workup

  1. customto prepare a mixed solution
  2. customAfter completion of the reaction
  3. aliquota part of the reaction mixture was sampled
  4. customThen, the components of reaction mixture

Sources & evidence

ORD record
ord-fd147747aa8e43d0add2d735ddb6acd9
Source dataset
uspto-grants-2002_04
Patent number
US06372921B1

Reaction notes

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