Oxygen → 2-Chlorobenzoic Acid

Temperature

155 °C

Into the column described in Example 1 were charged 453 grams (3.58 moles) of o-chlorotoluene, 2.25 grams of cobalt octoate (6% Co), and 2.25 grams of epichlorohydrin. The reaction mixture was heated to 155° C. and maintained at that temperature while oxygen that had been sparged through epichlorohydrin was bubbled through it at the rate of 200 ml./min. Throughout the reaction period, the gases leaving the reactor remained non-acidic. At the end of 23 hours, the reaction mixture was removed from the column, cooled to 75° C., and extracted with 600 grams of 10 percent aqueous sodium hydroxide solution. The layers that formed were separated. The aqueous layer was diluted with water to a volume of 1500 ml. and then acidified with hydrochloric acid. The o-chlorobenzoic acid that precipitated was collected, washed with water, and dried. There was obtained 180 grams (1.155 moles) of o-chlorobenzoic acid. The conversion of o-chlorotoluene to o-chlorobenzoic acid was 14 percent. The yield of o-chlorobenzoic acid, based on o-chlorotoluene reacted, was 78.6 percent.

1. customhad been sparged through epichlorohydrin
2. customwas bubbled through it at the rate of 200 ml
3. customThroughout the reaction period
4. customthe gases leaving the reactor
5. customAt the end of 23 hours, the reaction mixture was removed from the column
6. temperaturecooled to 75° C.
7. extractionextracted with 600 grams of 10 percent aqueous sodium hydroxide solution
8. customThe layers that formed
9. customwere separated
10. additionThe aqueous layer was diluted with water to a volume of 1500 ml
11. customThe o-chlorobenzoic acid that precipitated
12. customwas collected
13. washwashed with water
14. customdried

ORD record

ord-ac39148028b44a73bcdd872445048803

Source dataset

uspto-grants-1977_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04034007