Alkyl Halides in Acid/Base

[macdonda]

Hi, I have an interesting problem... we contact a stream of low MW liquid hydrocarbons with 50% sulfuric acid. Two inpurities are methyl bromide and methyl chloride... the mass balance shows these molecules remain in the hydrocarbon phase... is that expected? Also, we pass the hydrocarbon through a scrubber that's on pH control... if I raise the conc of NaOH significantly, would I expect to see methanol and sodium halide salts? Any thoughts will be appreciated... thanks!

 

[Chance17]

Yes -you would begin to caustic crack the chlorinated hydrocarbons.
Years ago when I was in manufacturing, the same chemistry was observed in vinyl choride plant operatins.
At ph=9.0 there was very little cracking.
At pH=10 and above (especially 12.0) cracking was significant.