Benzyl Chloride- In Review

Guest · Mon Feb 07, 2005 12:02 pm

Benzyl Chloride MSDS
http://physchem.ox.ac.uk/MSDS/BE/benzyl_chloride.html

Loomis patent

beaker · Busy Bee

Swib would like to add that a closed Igloo cooler full of sealed reagent bottles(unopened) of this material couldn't contain the chemical smell. The bottles were originally packed in cellulose filled metal canisters, and should have been kept that way.

The smell is somewhat similar to toluene.

Guest · Sun Feb 13, 2005 10:07 am

Except toluene doesnt make you cry and vomit.

IndoleAmine · Dreamreader Deluxe

Nor does it make you cough and salivate like and old, big asthmatic dog...
(toluene doesn't make you "blush" either Mr. Green

)

Benzyl chloride is NASTY stuff - SWIA too has some reagent grade bottles, all but one unopened, and wishes he'd never bought them.. - was cheap though...

But really: I just wanted to check the bottle label for safety warnings (R/S) and acute toxicity statements - but on my way to the storage room, I decided that it would be better to let them sit UNDISTURBED and give a f*** on the information imprinted on them, rather than to have this nasty stinging odor around for several daze again... Confused

Something for *real* hardcore chemists (not me).

I_A

anime · Tue Apr 19, 2005 11:44 am

http://physchem.ox.ac.uk/MSDS/BE/benzyl_bromide.html

The benzyl bromide seems a little safer (or is there data missing?)

IA you could always just dump that benzyl chloride into a nice NaOH solution, stir and heat. Although that’s easy for me to say since I've never been around it. There are definitely nasty chemicals (like bromine) its always good to keep away (unless of course you enjoy the feeling of the mucus lining of your respiratory system stripped away)

Bluechip · Tue Apr 19, 2005 5:02 pm

THis beats the Loomis patent for all you Benzyl chloride nuts.

PATENT NO.GB134250

4,250. Levinstein, Ltd., Levinstein, H., and Bader, W. July 27, 1918. Chlorhydrocarbons. - Benzyl chloride, benzal chloride, and similar side-chain chlor-substituted aromatic hydrocarbons are prepared by treating toluene or its homologues at a low temperature with aqueous hypochlorous acid (hypochlorite and acid). The process can also be applied to the treatment of the chlor-derivatives of these hvdro- carbons containing one or two chlorine atoms in the nucleus or one chlorine atom in the side chain, e.g. monochlortoluenes, 2 : 4-dichlorto- luene, or benzyl chloride. Examples are given of the preparation of benzyl chloride from toluene and benzal chloride from benzyl chloride; m- xylene gives m-tolyl chloride and m-tolal chloride.

Nasty.

IndoleAmine · Dreamreader Deluxe

Benzyl bromide is even worse, thanks. I have no problems with Br2 though... Laughing

(benzyl chloride is a sensitizer and acts exactly like tear gas, it somewhat feels like huffing toluene flavored with chlorine and drinking a pint of benzyl alcohol at the same time. And then there are the obvious effects: you start to cough, cry and salivate like after being "treated" with pepper spray, while your face gets red, your nose burns and your throat too, and you feel really intoxicated (it is "T+"/very toxic, like acetonitrile, CCl4 and HCN). Got the picture? Laughing

)

I must admit that my experience mostly stems from an accident involving an addition funnel filled with that stuff being shot right up to the ceiling and raining down on me... Shocked

IndoleAmine · Dreamreader Deluxe

Did I mention that BzCl is very corrosive too, and that I still have some signs of minor burns on my right leg from that stuff?

The all-around everytime party favorite! Corrosive, toxic, lacrimator, stinks, is flammable too...

The rxn with NaOH requires benzalchloride, I thought!?

Mr. Green

anime · Sat Apr 23, 2005 1:16 am

hmm sounds delicious....

The only benzyl halide I'm been around was 1,4-dimethoxybenzylbromide and the bis benzyl bromide (1,4-dmb is verry reactive Sad

). But the effects are not as bad, its a solid so it has a very low vapor pressure. It does burn, so handling it with gloves is a must. Smells like a very pungent pepper. I tried hydrolysis on the bis product and it slowly turns to an orange color. Cooling it yields an orange paste. NaOH was used for the hydrolysis. I think base weaker base would do a better job (I believe deprotonation of the alcohol could occur and that could react with benzylbromide yielding an oxydibezene product.)

Later on I found that soda ash is used for the hydrolysis of benzyl chloride to benzyl alcohol.
(http://www.chemicalland21.com/arokorhi/industrialchem/solalc/BENZYL%20ALCOHOL.htm)

Do you know if it would be possible to oxidize it to benzaldehyde directly using the persulfate method? I guess the Sommelet rxn is a possibility. Anyone have any references regarding this?