Sciencemadness Discussion Board

Handling Benzoyl Chloride?

FireLion3 - 11-8-2015 at 22:13

I was planning to get some of this for a Benzoylation reaction, since the Anhydride seems to be super expensive. I know from experience that Benzyl Chloride is super lachrymatic and unfun to be in the same room as. How does Benzoyl Chloride compare? I have a sneaking suspicion that it could be even worse/more reactive, due to the carbonyl. Though, I also suspect it could be less harsh due to the higher vapor pressure, ie less in the air when handling.

Has anyone worked with this before?

[Edited on 12-8-2015 by FireLion3]

kavu - 12-8-2015 at 02:34

Benzoyl chloride is not nearly as bad a lacrymathor as benzyl chloride. It just has a pungent, peculiar unpleasant smell to it that tends to stick around in your nose. Because of this, I usually do reactions involving benzoyl chloride outdoors.

[Edited on 12-8-2015 by kavu]

Dr.Bob - 12-8-2015 at 05:14

It is not as bad as benzyl, since it hydrolyzes quicker, and is less irritating, but still makes HCl when it contacts water, so it is rough on the eyes and lungs. As you say, the BP is higher, so not as volatile. If you don't have a hood, then outside is best.

FireLion3 - 13-8-2015 at 00:15

That's good. I have a pretty good filter system. My experience with Benzyl Chloride also had it heated in solution that it was made in situ, unintentionally. It was bad. I felt like if i stayed in the room I would die.

You say benzoyl chloride is rough on the eyes and lungs. Is that like, similar to how HCl would be, just sort of unpleasant to be around for prolonged periods? My experience with Benzyl Chloride was basically *exit the area as quickly as possible!!!!*.