Author Topic: Benzyl Chloride  (Read 595 times)

Vesp

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Re: Benzyl Chloride
« Reply #20 on: June 29, 2009, 04:44:04 AM »
What is Old Spice? The cologne?
Do you know the other chemicals in it as well?
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Sedit

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Re: Benzyl Chloride
« Reply #21 on: June 29, 2009, 04:53:38 AM »
Yeh the cologne.

Ethanol/SD Alcohol 40
Benzyl alcohol
Water
Fragrance(s)/perfume(s)


OTC Benzyl alcohol.
http://whatsinproducts.com/search_ingredients_result.php?chemicalId=142&PHPSESSID=5259

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You pissed off the wasp now enough is enough!!!

2bfrank

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Re: Benzyl Chloride
« Reply #22 on: July 02, 2009, 05:12:12 AM »
Yeah TCCA is a very common chlorine source for pools.

Bubbling chlorine gas in at a slow rate is also supposed to work IIRC.

Pool shops also can have oxone, potassium peroxymonosulfate, which was very much a surprise. It is a non-chlorine oxidiser with lots of uses.

2bfrank

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Re: Benzyl Chloride
« Reply #23 on: August 15, 2009, 02:49:22 AM »
Electrochemical chlorination of toluene in two phase electrolysis.

Been meaning to include what looks like a pretty user friendly prep of 2 phase oxidation of toluene to Benzyl chloride and the additional generation of  minute amount of chlorotoluenes and overall looks might good.  Obviously, well at least with respect to one other paper, that confirms the potential for 2 phase electrochemical, this set up could indeed be used for other type reactions that go through a typical free radical chain reaction pathway. This procedure is very applicable to the formation of Chloroform, and appears to have some good overall scope. I will dig up that 2 phase chloroform prep, as it is of interest and may be handy for a member here
One potential issue, is this paper using chloroform as the solvent that the toluene is added for the hydrocarbon phase and uses aquarius sodium chloride the other phase . I see that their would be no issue of using a cell with just toluene, for the hydrocarbon phase of this said reaction and separation obtained by the b.p differences, of toluene and benzyl chloride

2b
« Last Edit: August 15, 2009, 02:58:08 AM by 2bfrank »

Sedit

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Re: Benzyl Chloride
« Reply #24 on: August 15, 2009, 03:00:46 AM »
I have not read the paper yet(Recently anyhow) but there could be a problem when using neat toluene because the solvent may be in place to prevent formation of benzal chlorides or possibly aid the mediation in the formation of benzyl chloride instead of the ring substitued product.

Chloroform is no real problem for the home chemist to synthesis other then the large bulk of the reaction. See the chloroform theed in other
chemistry.

[edit]

After a quick review what does every one think about Pb electrodes as instead of Pd electrodes? Other then them I would be all set to perform this quick experiment after a little cleaning and polarizing my cell.
« Last Edit: August 15, 2009, 03:07:14 AM by Sedit »
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2bfrank

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Re: Benzyl Chloride
« Reply #25 on: August 15, 2009, 03:05:57 AM »
yeah, didn't consider that, but chloroform aint such a hurdle, and can easily be obtained by for starters a 2 phase electro prep, and the known ones all over the place.   THis paper albeit that one issue, looks pretty good, and it was sort of obvious, and on the cards but a paper is handy, etc...

Vesp

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Re: Benzyl Chloride
« Reply #26 on: August 15, 2009, 03:45:32 AM »
Very interesting! I bet graphite electrodes would work with out much of a problem, I don't know about lead. Just something that doesn't react with the chlorine being formed, so essentially whatever works in a chlorate/hypochlorite cell.

It seems the function of the chloroform is to simply sink the toluene. That means that other solvents that will not interfere could be used. Possibly tetrachloroethylene, which is more OTC then chloroform, could be used as well if it didn't react.





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Sedit

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Re: Benzyl Chloride
« Reply #27 on: August 15, 2009, 03:51:45 AM »
No need for anything fancy as DCM is always there as a nice little backup. That will be my first choice here and it shares many properties with Chloroform as well. Temperature controle will be a bitch and I may just have to cut down to a really long cell run and cut the ampers down to something like 500ma without strong external cooling.
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You pissed off the wasp now enough is enough!!!

Vesp

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Re: Benzyl Chloride
« Reply #28 on: August 15, 2009, 04:01:38 AM »
Well, then it will float. I think this could cause problems - such as the Cl2 floating up and dissolving into the organic layer..but perhaps that won't matter. It just seems weird that they would go through the effort to keep it on the bottom using chloroform if it doesn't have some other use.
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Sedit

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Re: Benzyl Chloride
« Reply #29 on: August 15, 2009, 04:03:21 AM »
????HUH????

DCM is a bottom puller Vesp. Not much different the Chloroform at all.

[edit]
hey cool look if you put 4? marks in a row it creates that lil confused face.
There once were some bees and you took all there stuff!
You pissed off the wasp now enough is enough!!!

Vesp

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Re: Benzyl Chloride
« Reply #30 on: August 15, 2009, 04:06:51 AM »
Oh shit you are right. WTF am I thinking.
Ha, I dunno I must have been thinking of ethyl acetate or some other solvent. It has been a while since I've messed with it, as if that isn't obvious.
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2bfrank

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Re: Benzyl Chloride
« Reply #31 on: August 17, 2009, 09:34:04 AM »
I rechon DCM would be fine, but could possibly compete, as the very same sort of conditions use DCM to produce CHCl3... if memory serves me correct... I think Ill try both and see what occurs... and the graphite as youve suggested should be okay. I am not that up with electostuff, but kind of like it..and think I have read, or heard that carbon can sort of replace the electrode in the paper... similiar over potential or something.
tomorrow is the day for this for me..Ill try and find that DCM>CHCl3 2 phase prep.. I am going to have to sort my files, and perhaps take the offer to put them up to share...

2b

lugh

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Re: Benzyl Chloride
« Reply #32 on: August 17, 2009, 12:12:19 PM »
Toluene and benzyl chloride form an azeotrope, which can be separated using azeotropic distillation by adding isopropanol to form the lower boiling point azeotrope with toluene  ;) The toluene-isopropanol can be separated by adding water, the isopropanol-water mixture can be separated using sodium chloride  ;D
Chemistry is our Covalent Bond

2bfrank

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Re: Benzyl Chloride
« Reply #33 on: August 18, 2009, 12:42:59 AM »
Thats good to hear about. I have avoided this, and lack experience, but if adding a determined amount of isopropanol to the mix, and this holding the toluene, and can be simply distilled of, well its good news indeed.
Less work perhaps, all the better, ill check out these b.p's of these azeotropes, Thanks lugh indeed.. ;)

ps.. Benzyl acetate prep, electro.. Didn't know where to post it.. Similiar to Mn3+ > the honey. Apologies if already posted.
« Last Edit: August 18, 2009, 12:50:32 AM by 2bfrank »

POSEIDON

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Re: Benzyl Chloride
« Reply #34 on: September 06, 2009, 07:21:33 PM »
hey swip found this in orgsyn check out
The chemists are a strange class of mortals, impelled by an almost insane impulse to seek their pleasures amid smoke and vapour, soot and flame, poisons and poverty; yet among all these evils I seem to live so sweetly that may I die if I were to change places with the Persian king.
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lugh

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Re: Benzyl Chloride
« Reply #35 on: September 27, 2009, 05:32:55 PM »
The isopropanol-toluene azeotrope boils at around 80 degrees Centrigrade at STP, and contains at least 50% isopropanol unless one lowers the pressure down to aboout 20 mm Hg ;) One can use methanol in the same manner, but since the methanol-toluene azeotrope contains less toluene than the isopropanol-toluene azeotrope it's best to use isopropanol  ;D
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no1uno

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Re: Benzyl Chloride
« Reply #36 on: September 28, 2009, 11:26:49 AM »
No need for mouthwash if you want OTC BnOH look at Old Spice. It is something along the lines of 30-40% BnOH. I found this out after dumping 3 bottles of it down the drain because my daughter took a bath in it.

The big bottle I have here is 125ml so at 30% your looking at 37.5 ml of BnOH or 39.15 grams of Benzylalcohol. If your hard up I guess you could do it. Sure beats 1% mouthwash

Or even better (probably also cheaper) Benzyl Benzoate is in most (if not all) chemists/pharmacies for Scabies/Head lice treatment (avg seems to be around 25% emulsion - in about 200mL packs [approx $9-10], so what, 50g of the ester/pack [1 mol of the ester = 212.2g = 0.236 mol/pack], hydrolysis of which would give 0.24mol of both Benzyl alcohol [25.5g]and benzoic acid [28.8g - yeah I know, it don't add up, think about the extra OH before you post;)])...

It is also available for Horses, so vet supply shops should stock it in far larger qty's for a cheaper price / L.
« Last Edit: September 28, 2009, 11:31:55 AM by no1uno »
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