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Alkyl Halides in Acid/Base

Alkyl Halides in Acid/Base

Alkyl Halides in Acid/Base

(OP)
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!

RE: Alkyl Halides in Acid/Base

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.

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