Chemistry Forums for Students > Organic Chemistry Forum
2-nitrobenzoyl chloride
harmonic_op:
--- Quote from: clarkstill on June 04, 2019, 11:48:13 AM ---You can obviously make it from 2-nitrobenzoic acid, but a word of caution: i made about 200 mL of this during my PhD and purified it by vacuum distillation. Once I'd finished, I foolishly let air into the distillation kit before it was fully cooled to room temperature - it exploded pretty violently, but luckily while I (and everyone else) was elsewhere in the lab. The glass thermometer was projected into the ceiling of the fumehood and pretty much turned into sand by the impact.
So, be careful and use appropriate PPE (e.g. blast shield) if you're inclined to make this on a large scale.
--- End quote ---
Thank you for the heads up i didnt knew that it is an unstable product.
clarkstill:
--- Quote from: wildfyr on June 04, 2019, 12:15:10 PM ---What caused the explosion? This compound doesn't seem shock sensitive.
--- End quote ---
Hard to know, all that was left was black char! Like I say, it was the stuff left in the still pot that went up, and only when exposed to air, but that's all I know. It totally caught me by surprise because, like you say, I hadn't expected it to be a major hazard.
clarkstill:
Although looking just now, the EROS entry mentions explosion during distillation.
https://onlinelibrary.wiley.com/doi/abs/10.1002/047084289X.rn030
Just goes to show it’s worth doing your due diligence, especially when scaling up...
wildfyr:
Trace iron or aluminum, presence of HCl from acid chloride forms some Al/FeCl3, makes the ketone via friedel-krafts acylation upon heating, that is the explosive when some moisture hits or it cools and crystallizes?
rolnor:
I think the nitro-group de-activates the ring and inhibits Friedel Craft? Also the carbonyl is de-activating.
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