Thionyl Chloride → Laurolactam

Temperature

100 °C

Within a glove box, 0.033 g (0.17 mmol) of cyclododecanone oxime prepared in Reference Example 2 was dissolved in 0.400 g of a 5% by weight thionyl chloride (rearrangement catalyst)/toluene solution (0.020 g (0.17 mmol) as pure thionyl chloride), and the mixture was stirred using a magnetic stirrer at room temperature (25° C.) for 5 min, to conduct the pre-preparation of a rearrangement catalyst. After the pre-preparation, high performance liquid chromatography analysis indicated that cyclododecanone oxime had been consumed. Separately, within a glove box (under nitrogen atmosphere), in a flat-bottom flask equipped with a manifold, 3.285 g (16.64 mmol) of cyclododecanone oxime and 0.023 g (0.17 mmol) of zinc chloride were weighed and then 7.00 g of toluene was added, and the materials were dissolved by heating the mixture to 100° C. in an oil bath. To the zinc-chloride containing solution of cyclododecanone oxime in toluene, the reaction mixture which had been prepared in the pre-preparation using cyclododecanone oxime and thionyl chloride in 1:1 molar ratio was added, which then reacted for 60 min. The reaction solution was clear without turbidity, and gas chromatography analysis indicated that a conversion of cyclododecanone oxime was 100% and a laurolactam yield was 98.8%.

1. customat room temperature
2. custom(25° C.)
3. customfor 5 min
4. customthe pre-preparation of a rearrangement catalyst
5. customAfter the pre-preparation, high performance liquid chromatography analysis
6. customhad been consumed
7. dissolutionthe materials were dissolved
8. addition1 molar ratio was added
9. customwhich then reacted for 60 min

ORD record

ord-00b8032a959e4335b0845a1c12a5a3f9

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530645B2