BENZYL CHLORIDE

HOTPLATE · Sun Aug 14, 2005 7:36 am

Has anyone seen or done the benzyl chloride synth by adding the hypochlorite directly
to the toluene.does it work and how dangerous is it.The patent is by Chauncey c loomis october 1917.I have seen plenty of synthesis by piping in chlorine but none by direct addition of hypo any help appreciated.Also what is the easiest acetaldehyde synth.

secret_squirrel · Sun Aug 14, 2005 11:49 am

There's a really good thread on sciencemadness.org on preparation of acetaldehyde. The easiest method? Who knows. It probably depends on how much you want, how much you want to spend on reactants, equipment, etc.

hAzzBEEn · Mon Aug 15, 2005 11:02 pm

Link to the acetaldehyde thread?

MiNdBaBY · Tue Aug 16, 2005 4:44 am

Haz, try TFSE Smile

As for your original question on BzCl thru hypoCl reflux, the most MiNd has obtained is 25% yield and cleanup is a pain in the ass of the boiling flask (MiNd did so in one gallon qty's). It is notable, that MiNd had utilized various OTC preparations of hypo ranging from a 40-60% hypo content and that the impurities/contaminants of the OTC preparations (utilized in the pool/spa industry) did not inhibit the rxn.

This method is easy, but yields are HORRIBLY low and she eats up your tolly. MiNd would suggest a NaCl downs cell utilizing $4-$8/40lb bags of NaCl for Cl gas productions and recovery and storage of the Na.

MiNdBaBY · Tue Aug 16, 2005 4:55 am

Oh missed a few points..

It is very easy, and very low on the danger scale IMHO.
MiNd highly suggests ya try it just for the sake of having done such.

You also need to do this rxn in LRG qty in order to recover anything worthwhile, i.e. one gallon or larger! Reflux w/condensor attached in an oil bath, monitor bath temp (MiNd never exceeded 107C in his rxns). Upon refluxing for 1-2 hrs, MiNd would insert a Claisen and reattach the condeser for distillation and distill off the tolly & BzCl, it is to be noted that the tolly will leech out the BzCl and seperation afterwards is accomplished with a sep funnel, then redistillation with fractionization.

It's alot of work for so little yield. Trust me!
Downs cell production of Cl though not simplistic with regard to equipment setup is most feasible from OTC perspective and inexpensive expense!

But MiNd DID say that straight OTC hypo can be used. MiNd had wondered greatly about such besides experiement which various cleaning procedures (beware, attempted cleanings get fucking HOT & exothermic) before finally making a run with straight OTC and having such work, as well MiNd tried multiple variations of hypo OTC products, the most concentrated being a 63% and the least being a 43 or 47%.

As for cleaning out the boiling flask after rxn, MiNd found Sodium Hypo (common OTC bleach) helped considerably in loosening up the Ca and gunk.

MiNdBaBY · Tue Aug 16, 2005 4:56 am

Easiest Ethanal synth is from the OH in a MAA Electrolysis cell in an cooling bath.

hAzzBEEn · Tue Aug 16, 2005 7:41 pm

SWIh prefers to reference the same document as the author of the post. SWIh thinks for good discussion, all material should be provided. Ya know, keep everyone on the same page from the start?

Here is the Acetaldehyde link:

Sceincemadness.org: Acetaldehyde Synthesis

Good thread.

Bushroot · Fri Aug 19, 2005 2:11 am

at least hypochlorite is much safer and much easier to handle than the chlorine gas!

I work in pesticide synth lab, the last week we were making 2,6 dichloro-3-hydroxy-pyridine (it's N-oxide later). Chlorinating it with chlorine from gas baloon yielded a full flask of resinous crap, while chlorinating it with hypochlorite (prepared from saturating NaOH solution with Cl2) gave a good yield of quite pure brown crystals...
Sorry I can't say about toluene but hypochlorite is convinient in many cases..

MiNdBaBY · Sat Aug 20, 2005 11:54 am

Bush, your prepared hypo is a lil different from the OTC Ca hypo available, common, and likely to be used (at least in the U.S.) which is based on Ca.

I'm kinda going off on assumptions and my opinion when I say this, but your prepared hypo from gas which you don't directly state, but Cl2, my point being I assume and am confident you DID work with Chlorine gas at some stage, i.e. the preparation of a hypo compound

But my point I was after making is a 'hunch', and that is that your Na (sodium) based hypo would have far better yields and results compared to the Ca (calcium) based hypo so commonly available OTC in many countries. Regarding elemental's, Ca is at the bottom of the muther fuggin list.. lol Smile

Dunno if such has been done but a Li hypo would really be interesting to play with, and on this topic a K (potassium) based hypo would be far better than the otc Ca, while Na is pretty much at the top of the list aside from Li..

The Ca based hypo MiNd used in his experiments with such synth route, is probably a MAJOR factor player in the horrifficly low yields..

But bush, thanks for the tid bit and suggestion, with regards to preparing a Na based chlorite via Cl2, but in all honestly since you're still working with the gas, one would save themselves the trouble and labor by just Chlorinating they're primary precursor (such as Toluene).. Just MyHumbleOpinion.

MiNdBaBY · Sat Aug 20, 2005 4:19 pm