joejoe
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C7H7CI
I want to make C7H7Cl buy heating toluene and bleaching powder. the imformation that i have found is very limited and was if anyone knew where to find
a detailed description of the experiment.
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Sauron
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Organic Syntheses website
The forum library
UTFSE
There are threads on making benzyl chloride
Nasty stuff. Protect yourself. Goggles, respirator, gloves, work outside if you have no fume hood (sounds like you don't.)
See Sartori's THE WAR GASES in forum library for why.
Are you sure you want benzyl chloride?
Sic gorgeamus a los subjectatus nunc.
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Sedit
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| Quote: | Originally posted by joejoe
I want to make C7H7Cl buy heating toluene and bleaching powder. the imformation that i have found is very limited and was if anyone knew where to find
a detailed description of the experiment. |
There are a few very compleat threeds here at SM, use the search function at the top left corner for Benzylchloride.
Knowledge is useless to useless people...
"I see a lot of patterns in our behavior as a nation that parallel a lot of other historical processes. The fall of Rome, the fall of Germany — the
fall of the ruling country, the people who think they can do whatever they want without anybody else's consent. I've seen this story
before."~Maynard James Keenan
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Sauron
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Benzylchloride is a forum member.
Benzyl chloride is a compound.
Do not omit the space when you search.
Sic gorgeamus a los subjectatus nunc.
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Sauron
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Chloromethylation of benzene with formaldehyde and HCl is a particularly good method.
I started a thread on that last year.
http://www.sciencemadness.org/talk/viewthread.php?tid=11065&...
len1 likes radical chlorination of toluene elementally with UV photolysis. He did a thread on that.
There is also radical chlorination of toluene with SO2Cl2 and benzoyl peroxide
Benzyl alcohol is easily chlorinated with a variety of reagents such as TCT, TCT/DMF, hydrochloric acid, anhydrous HCl, TCCA, NCS, etc.
Benzyl alcohol can also be reated with Ph3P in CCl4 to give benzyl chloride and Ph3P=O and chloroform.
I also know how lachrymatory benzyl chloride is and suspect the thread author has little or more likely no protective gear so I have a lot of safety
advise for him.
[Edited on 4-3-2009 by Sauron]
Edit by Nicodem: All posts by Sauron and Sedit containing personal attacks have been removed! I advise you two take it over the U2U messaging
system as nobody is interested in your intimate discussions. You two crossed the tolerable decency limit. Grow up already!
[Edited on 4/3/2009 by Nicodem]
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Ebao-lu
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Is it sossible to radically chlorinate toluene by CCl4? CCl4 is generally prohibited, but not everywhere..
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Sauron
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No. The CCl4 reaction with triphenylphosphine to chlorinate benzyl alcohol not toluene is closest thing to that.
SbCl5 will probably chlorinate toluene either stoichiometrically according to
PhMe + SbCl5 -> PhCH2Cl + SbCl3 + HCl
or catalytically
PhMe + Cl2 -> PhCH2Cl + HCl
in presence of SbCl5 or SbCl3 for that matter
FeCl3 anhydr may work as well but antimony is much more active.
Cf chlorination of CS2 to CCl4.
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JohnWW
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| Quote: | | Originally posted by Sauron(cut)There are threads on making benzyl chloride. Nasty stuff. Protect yourself. Goggles, respirator, gloves, work
outside if you have no fume hood (sounds like you don't.). See Sartori's THE WAR GASES in forum library for why.(cut) |
Are alpha-phenyl alkyl chlorides that dangerous (more so than CCl4 or CH2Cl2), other than to insects (to which many chlorocarbons are lethal, like
DDT)? There is the possibility of hydrolysis to benzyl alcohol and HCl on exposure to alkalis, but that seems to be all.
BTW Be careful what you ask for; - C7H7Cl has several structural isomers, including the ring-chlorinated toluenes; and also tropylium chloride, which
is an ionic chloride with a 7-membered aromatic ring.
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unionised
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Can I just flag up the fact that the reaction of HCl and HCHO can give rise to bis chloromethyl ether- one of the more potent carcinogens?
Relatively speaking, the desired product is a walk in the park
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PHILOU Zrealone
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| Quote: | Originally posted by JohnWW
| Quote: | | Originally posted by Sauron(cut)There are threads on making benzyl chloride. Nasty stuff. Protect yourself. Goggles, respirator, gloves, work
outside if you have no fume hood (sounds like you don't.). See Sartori's THE WAR GASES in forum library for why.(cut) |
Are alpha-phenyl alkyl chlorides that dangerous (more so than CCl4 or CH2Cl2), other than to insects (to which many chlorocarbons are lethal, like
DDT)? There is the possibility of hydrolysis to benzyl alcohol and HCl on exposure to alkalis, but that seems to be all |
-Halides in alfa of an electron withdrawing group are much more reactive than other organic halides...
In that family you find lacrymators, vesicants and wargasses...
-Benzyl chloride (Ar-CH2Cl)
-Allyl chloride (CH2=CH-CH2Cl)
-Chloroaceton (CH3-CO-CH2Cl)
-Chloropicrin (O2N-CCl2-Cl)
-....
They often readily exchange their halide to fix to an amine moeity from eye, lung, skin, nose membranes...
PH Z (PHILOU Zrealone)
"Physic is all what never works; Chemistry is all what stinks and explodes!"-"Life that deadly disease, sexually transmitted."(W.Allen)
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Sauron
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unionized, I suggested you have a look at Merck Index monograophs on chloromethyl methyl ether, and on bis(chloromethyl)ether.
Back when they were newly created Nanny State organs, EPA and OSHA classified the former as a carcinogen ONLY because of contamination of the
commercial product by the latter. In short they threw the baby out with the bathwater.
Pure chloromethyl methyl ether, uncontaminated by the symmetrical dichloro ether, is not a carcinogen, in reality, despite what these agencies say.
It is perfectly possible to prepare such pure chloromethyl methyl ether by the unambiguous method I have previously referenced. This is the reaction
of formaldehyde dimethyl acetal (dimethoxymethane) with hexanoyl chloride. Both the acetal and the acyl chloride are readily available commercially
and readily preparable.
The only carcinogen in the prep of benzyl chloride by chloromethylation of benzene as long as the preparation is done by the method I described.
I do not see unionized waxing nannyish over the threads on this foprum pertaining to the preparation of benzene from benzoic acid, or other threads in
which benzene is used.
I posted a number of other methods for making benzyl chloride which employ neither benzene nor chloromethylation. Anyone uncomfortable with those
reagents ior procedures. please avail yourselves of the alternatives.
BUT DO SO IN AN INFORMED INTELLIGENT WAY MAKING YOUR OWN DECISIONS AND NOT REACTING TO THE KNEE JERK HYSTERIA BEING PROMULGATED BY THE BUREAUCRATS.
The target compound is benzyl chloride and the preparation, ANY preparation and handling of benzyl chloride needs to be done only in a HOOD and with
the use of proper protective clothing and equipment.
Procedures that have been recommended involving the use of UV to catalyze chlorination of toluene are hazardous to the eyes, requiring containment of
the US lamps so that NO UV light, even reflected, escapes the containment. Your hobby is not worth losing your sight.
UV is also a skin cancer hazard. Ever see anyone dying of malignant melanoma? Not a pretty sight.
Safety first last and always but use your brains and READ, don't be sheeple.
Sic gorgeamus a los subjectatus nunc.
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benzylchloride1
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I have prepared Benzyl chloride several times by chlorinating toluene at its boiling point. A 1 mole synthesis takes about 5 to 6 hours for the
chlorination using a 60 Watt incandescent light bulb as the UV light source. Not much UV light, but it gets the job done. Check Len1's article on
benzal chloride and benzaldehyde, a procedure can be adapted from this. Be sure to read the warnings as benzyl chloride is one of the most unpleasant
organic chemicals that I have ever worked with. It gives a very strange chemical taste on inhaling a very small quantity when you clean the glassware.
The chlonation is easy if you use Len's method of generating chlorine from TCCA. Do not do this without a hood! I have made a small amount of benzyl
chloride by heating toluene with TCCA at its boiling point under the influence of UV light. It works, but you will need a fritted funnel to filter off
the precipitated cyanuric acid. This procedure is not very safe due to the possibilty of run away reactions and the prospect of filtering benzyl
chloride, Yuck! Benzyl chloride is a useful reagent, but do use it to make derivatives of phenethylamines, as this ruins our cause as madscientists.
What is the best method of cleaning glassware contaminated with benzyl chloride?
[Edited on 18-3-2009 by benzylchloride1]
Amateur NMR spectroscopist
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JohnWW
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Benzyl chloride? That could be hydrolyzed in a strong aqueous alkali to produce benzyl alcohol, and this then subjected to mild oxidation to get
benzaldehyde, which is an important starting material for syntheses (as well as usable as artificial bitter almond essence in making cakes).
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benzylchloride1
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Benzyl chloride is almost impossible to hydrolyze in a basic solution. Len tried to hydrolyze this compound with sodium hydroxide and was only able to
isolate the initial starting material, benzyl chloride. I attempted to synthesize benzyl acetate by refluxing benzyl chloride, acetic acid and a large
excess of anhydrous sodium acetate for 4 hours. The mixture still had the awful smell of benzyl chloride, not attempt was made at distilling the
product. Benzyl chloride can form some interesting organotin compounds that decompose to benzaldehyde and another organotin compound. Di and
tri-benzyl tin chlorides can be synthesized by refluxing benzyl chloride with tin powder in water for the tribenzyl compound or toluene for the
dibenzyl compound.
Amateur NMR spectroscopist
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