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chemrox
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cyclohexanone
cyclohexanone is one of those very useful but increasingly hard to obtain chems. Good longstanding relationship with suppliers and faxed memos for
the DEA file required. The only reason I can think of is once it was used to make PCP a psychtomimetic/psychotogenic anasthetic and animal
tranquilizer. Would you give your dog this shit?
So here's a way I think would work. Cyclohexane -> cyclohexene by KMnO4 or K2Cr2O7. Cyclohexene to cyclohexanone by PdCl2/CuCl2 & DMF. Also
formic acid and 30% H2O2. I'm trying to adapt one of these to MW. Maybe a clay substrate?
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evil_lurker
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Sorry don't mean to burst your hypothetical bubble, but I'm pretty damn sure you can order it without much fuss from these guys:
http://store.hvchemical.com/browse.cfm/4,506.htm
Not all chemicals are bad. Without chemicals such as hydrogen and oxygen, for example, there would be no way to make water, a vital ingredient in
beer.
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Antwain
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| Quote: |
Cyclohexane -> cyclohexene by KMnO4 or K2Cr2O7. |
What???
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Maya
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Quote:
Cyclohexane -> cyclohexene by KMnO4 or K2Cr2O7.
What???
Same....... Anyways, cyclohexanone is not hard to get at all
I've ordered liters, it has a huge number of industrial uses.
its also used in PVC pipe cement extensively, so if worse comes to worst, distill from there
\"Prefiero ser yo extranjero en otras patrias, a serlo en la mia\"
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Fleaker
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I think I have some that I can spare you. I know I have a lot of either that or cyclohexanol. I only have a few hundred mL of cyclohexene though so
tough luck there 
What are you planning on doing with it?
Neither flask nor beaker.
"Kid, you don't even know just what you don't know. "
--The Dark Lord Sauron
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evil_lurker
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| Quote: | Originally posted by Fleaker
I think I have some that I can spare you. I know I have a lot of either that or cyclohexanol. I only have a few hundred mL of cyclohexene though so
tough luck there
What are you planning on doing with it? |
He gonna cook some space dope with it, what else?
Not all chemicals are bad. Without chemicals such as hydrogen and oxygen, for example, there would be no way to make water, a vital ingredient in
beer.
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chemrox
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That's funny but untrue "lurker." One time many moons ago I did just that and didn't much care for the results. Earning your name I see. I was
going to make a few things that might react with either the fatty acids or the glycerins in biodiesel to make them absorb in the visible or UV range.
It's a total crap shoot. Make it, check it on the IR and try to react it in oil and then run the oil up on the UV/vis machine. After six months or
so we ought to know if anything is working and what its reacting with and maybe what it is.
I don't think the reaction I suggested would work anyway.. did it again, dammit. I was remebering cyclohexene from the alcohol by way of acid.
Forget the cyclohexene. Just oxidize the alcohol. Is there a way to oxidize the alkane? I think peroxide, peracetic acids and catalysts are
involved.
[Edited on 30-10-2007 by chemrox]
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Sandmeyer
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| Quote: | Originally posted by chemrox
So here's a way I think would work. Cyclohexane -> cyclohexene by KMnO4 or K2Cr2O7. Cyclohexene to cyclohexanone by PdCl2/CuCl2 & DMF. Also
formic acid and 30% H2O2. I'm trying to adapt one of these to MW. Maybe a clay substrate? |
In practice the Wacker process works good only for terminal alkenes (i.e. to obtain methyl ketones).
edit:
How is cyclohexane supposed to give cyclohexene using those oxidants? Did you mean cyclohexanol or what?
There are countless recipes on the net regarding epoxide/pinacol rearrangement method of converting alkenes to ketones. utfg.
must be very boring to make simple aliphatic compounds, buy them if possible.
[Edited on 24-2-2008 by Sandmeyer]
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chemrox
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Yeah- I had mis-remembered and should have looked it up first. "It must be boring.." tell me about it, I'm making propionyl chloride this week as I
just ran out of the supply I made last year. Why? either unavailable or too dear. Me-am has wide application and is another waste of time to make.
The alternative is having too many regulators asking about ones business. Did I mention that having been away from wet chem for decades I need the
practice? I distill hardware solvents to hold costs down and fine tune my ditillation practices at the same time. I'm getting ready to 'graduate'
though and start playing around with catlysts for coupling reactions.
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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grind
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| Quote: | | Originally posted by chemroxIs there a way to oxidize the alkane? |
Very difficult. But you can make this:
C6H12 + SO2Cl2 ---> C6H11Cl + HCl + SO2
Cyclohexylchloride is a good precursor for Cyclohexanol and Cyclohexene.
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Ozone
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I am procrastinating from dissertation writing (dreaded background chapter). Shame, that.
Seems to me that, IIRC, we used alkaline KMnO4 to make adipic acid from cyclohexanone. I can't find my ancient lab manual so:
http://members.aol.com/profchm/chap22-6.html
Anyhow, I don't think cyclohexanone will react in any way with either fatty acids or glycerol (they just use brute force with the GC to get the
quantitation on the fatty acids and HPLC/DRI for the glycerol).
You can get cyclohexanone in small, unsuspicious quantities from HACH as standard material to go with their test kits.
Your chromic acid (Jone's reagent) route should work from cyclohexanol:
http://wwwchem.uwimona.edu.jm:1104/lab_manuals/c10expt21.htm...
Which (cyclohexanol) is also a nice source of cyclohexene via dehydration w/ 85% H3PO4.
http://wwwchem.uwimona.edu.jm:1104/lab_manuals/c10expt8.html
Which, of course, has the snake biting its tail. However, this looks interesting (catalysis):
http://www.wipo.int/pctdb/en/wo.jsp?WO=1997%2F08119&IA=W...
I'd elaborate, but I have to push hard and try to spew another page of scientific diarrhea.
Cheers,
O3
-Anyone who never made a mistake never tried anything new.
--Albert Einstein
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Sandmeyer
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Even a legitimate well equipped lab tries to avoid working with reagents like chromic acid, (IMO kind of a last resort reagent). I don't follow the
logic of going through the trouble of obtaining, working with and disposing stuff such as chromic acid just to prepare something as cheap, non-toxic
and readily available as cyclohexanone.
[Edited on 1-3-2008 by Sandmeyer]
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Jor
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chromic acid should be prety easy to dispose of by simply reducing it with acidified sodium sulphite.
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not_important
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| Quote: | Originally posted by Jor
chromic acid should be prety easy to dispose of by simply reducing it with acidified sodium sulphite. |
But still consuming expensive Cr(VI), which in some locals may even have a surcharge on it because of its toxicity and disposal problems (there are
people who will say "we'll I only have a little bit, I'll just pour it down the drain). And you add the cost of the sulfite on top of that.
I believe that chlorine bleach and Ni(OH)2 or NiCl2, as documented by Sauron and others, will do just fine at oxidising cyclohexanol to cyclohexanone
in 70% yield or so, and much less hassle in the workup as the nickel oxides/whatever can just be filtered out. Just plain old NaCl as a waste
product, bleach is cheap and still readily accessible.
That WIPO patent is basically creating Fenton's reagent on the fly, Fe(II) and H2O2, and assumable optimising the conditions for best yield of
cyclohexanol and cyclohexanone.
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jamit
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I have a chance to obtain about 1 liter of cyclohexanone. What can I used this for? What kind of synthesis? Should I get it? I did a search
...but it's not clear on what it can be used for... Except adipic acid?
[Edited on 21-2-2015 by jamit]
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Magpie
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cyclohexanone > adipic acid > nylon 66
The tricky part is coming up with some adipoyl chloride.
The single most important condition for a successful synthesis is good mixing - Nicodem
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jamit
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Thanks magpie! I'll look into both these products!
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Pickardjr
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I had an order stolen off the truck in route, it just disappeared from tracking. I called the company and they sent a new one, it made it. You can buy
it with no issues.
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Magpie
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Sorry jamit I think I oversimplified here. You are also going to need some hexamethylenediamine.
We made the nylon 66 in an organic lab at college. It's a simple & fun experiment once you have the 2 precursors.
[Edited on 22-2-2015 by Magpie]
The single most important condition for a successful synthesis is good mixing - Nicodem
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plante1999
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He could also make caprolactam and then turn that into nylon.
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turd
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Obligatory: https://www.erowid.org/archive/rhodium/chemistry/pcp/
(A nicely written document even for those not planning any of the included syntheses)
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Magpie
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adipic acid > cyclopentanone
I have done this one.
The single most important condition for a successful synthesis is good mixing - Nicodem
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Chemosynthesis
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Old thread, but to something the OP mentioned, while cyclohexanone was probably most cracked down on due to PCP synthesis, there are other narcotics
which use derivatives in their scaffold, just as with piperidine, which was obviously also scrutinized.
Magpie, presuming you used something on orgsyn?
http://www.orgsyn.org/demo.aspx?prep=CV1P0192
Too bad reducing strong enough agents to use on carboxylic acids aren't commonly OTC. I could potentially see a Dieckmann condensation, reducing the
beta keto acid, aminating to yield 1-aminomethyl-cycloalkanol, and then finally performing a Tiffeneau–Demjanov ring expansion rearrangement to
cyclohexanone as a mechanistically interesting synthesis.
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Magpie
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Here's my post on cyclopentanone. It looks like my attempt wasn't all that successful, but that of garage chemist was.
http://www.sciencemadness.org/talk/viewthread.php?tid=5564#p...
The single most important condition for a successful synthesis is good mixing - Nicodem
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CuReUS
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to what stage do you want to reduce it? if you esterify the COOH and treat that with DIBAL,you could reduce it to the aldehyde.then to get alcohol,you
could treat it with dithionite and to get hydrocarbon,you could do clemmenson.I think DIBAL can be made at home,as isobutanol is available
http://en.wikipedia.org/wiki/Diisobutylaluminium_hydride#Pro...
| Quote: | | I could potentially see a Dieckmann condensation, reducing the beta keto acid, aminating to yield 1-aminomethyl-cycloalkanol, and then finally
performing a Tiffeneau–Demjanov ring expansion rearrangement to cyclohexanone as a mechanistically interesting synthesis. |
I couldn't follow your reaction as you haven't mentioned your starting product,but if you are starting off with an ester of acid lower than adipic
acid,there might be a problem
Quote: Originally posted by Sandmeyer  | | Quote: | Originally posted by chemrox
So here's a way I think would work. Cyclohexane -> cyclohexene by KMnO4 or K2Cr2O7. Cyclohexene to cyclohexanone by PdCl2/CuCl2 & DMF. Also
formic acid and 30% H2O2. I'm trying to adapt one of these to MW. Maybe a clay substrate? |
In practice the Wacker process works good only for terminal alkenes (i.e. to obtain methyl ketones).
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see this
http://www.sciencemadness.org/talk/viewthread.php?tid=10007#...
[Edited on 23-2-2015 by CuReUS]
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