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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 842330Generated: October 31, 2026

Azobisisobutyronitrile → alpha-Chloro-o-xylene

https://huagongshe.com/reaction/842330

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAzobisisobutyronitrileHCID 6547—
Reactant1,2-Bis(chloromethyl)benzeneHCID 11919—
ReactantChlorineHCID 24526—
SolventO-XyleneHCID 7237—
Productalpha-Chloro-o-xyleneHCID 1109330%

Reaction Conditions

Temperature90 °C

Reaction Steps

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%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06372921B1
Source datasetuspto-grants-2002_04
ORD IDord-fd147747aa8e43d0add2d735ddb6acd9
Source noteuspto-grants-2002_04