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Sedit
International Hazard
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I thought about that myself John and all I could come up with is something that exploited the Cl in a way to aid in cracking the chain. Its all in the
mental what if stage at the moment but being a plumber that generates a good deal of PVC, CPVC and ABS waste why not attempt to make use of it. My
goal is Dichloroethane but it appears from the most recently reviewed text that many can be depolyermized to various simple organic acids and such.
This even though its not what I was looking for is great news. Oxalic acid from PVC and Acetic acid from PP are just to name a few.
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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entropy51
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Sedit, you should be able to buy oxalic at the hardware store as "wood bleach" cheaper than you can make it. Considering that you plumbers charge $89
per hour. 
Better to remain silent and appear a fool than to open your mouth and remove all doubt.
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Sedit
International Hazard
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89$ an hour LMAO we got done doing existing jobs along time ago... If you think we only make 89$ an hour your outcha friggin mind  . All new construction baby everything else is a waste of time and people in your way.
Either way yes I have about 500grams of Oxalic acid extracted from Bar cleaner a while back so its of no real concern but its still a great idea to
take a look at the reference section and look at the paper that DJF just provided. Im sure you may find something of use in that mess of simple
organics one can get from simply heating +catalyst of scrap plastics which are every where on to large a scale as it is. Perhaps if us amatures
started recyling we could get a better rep then we have right now.
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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not_important
International Hazard
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PVC, PVA, and similar don't neatly depolymerise, on heating PVC and CPVC mostly give HCl and highly unsaturated tars which break down under further
heating. Heating with metal oxides usually gives the chlorides or oxychlorides of the metals and organic gorp along with some carbon oxides.
As already said polystyrene and the polyacrylic esters do depolymerise well. ABS does give its monomers to some degree and a fair amount of gorp and
char. Wood gives 3 to 5 percent each of acetic and formic acids, depending on the type of wood, and some methanol.
Polyesters such as PET/PETA, and the polyamides such as nylons, undergo alkaline hydrolysis, some nylons hydrolise nicely with strong acids.
Polyurethanes can be hydrolyised as well, but many give a complex mixture of their basic components that isn't terribly useful.
Ethylene glycol may be the easiest OTC route to oxalic acid and 1,2-dichloroethane.
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Sedit
International Hazard
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Bromination to 1,2-dibromoethane from Ethylene Glycol was the plan to begin with but if I could get 1,2-Dichloroethane with ease on the cheep Im all
ears. It don't appear to be the case but I will still keep searching to see what I can dredge up. The last ref was interesting so I kind of want to
see what more is instore for these plastics.
[Edited on 12-9-2009 by Sedit]
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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Nicodem
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I suggest you to focus on bromination of ehtylene glycol with HBr or NaBr/H2SO4.
There is no simple way to 1,2-dichloroethane from vinyl chloride (which is a hazardous gas!) and there is even less chance of a feasible
depolimerization of PVC. Besides, 1,2-dichloroethane is a very common industrial solvent (for some reason they use it instead dichloromethane where
ever possible - maybe it is cheaper on the bulk?). It is a bit less common solvent in the research labs, but still there is no reason why you would
not just order it from a chemical supplier. It is not restricted, it is not suspicious in any way, and it is cheap. However, I would still prefer if
you would go the amateur route and do your own 1,2-dibromoethane from ethylene glycol, and post the experience.
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1281371269
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When distilling out ethanol such that it drips into a beaker, do I risk the majority of it being lost by evaporation? Do I need a closed apparatus, or
will sitting the beaker on some ice suffice?
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12AX7
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Ethanol doesn't evaporate all that fast. As long as it's cold from the condenser, it'll stay in place. Heck, moonshiners often use a bucket for the
reciever.
Tim
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1281371269
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Thanks
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Formula409
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I'm after some properties on the following compound (vapour pressure, boiling point, melting point, density): 3-chlorobut-2-en-1-ol
The only information I can find is "predicted information", obviously not suitable if one is using it for school work: http://www.chemspider.com/Chemical-Structure.9979359.html
Thanks in advance
Formula409.
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497
National Hazard
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Why is it that alkylation of tryptamine via routes like these do not alkylate the indole ring nitrogen?
Also would an methylation like this be able to avoid methylating the indole ring nitrogen?
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ketel-one
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What is indole? Benzene ring fused to pyrrole ring. Pyrrole is aromatic so doesn't get alkylated obviously.
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ammonium isocyanate
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What are you talking about? Firstly, aromatic compounds, including indole, can be alkylated. Secondly, he's asking about the nitrogens on the
compounds being alkylated. The nitrogen on indole has only to N-C bonds and can be alkylated just fine if deprotonated with a strong base.
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ketel-one
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Yes, but look closely at the structure. There's an aromatic pyrrole ring hidden in there.
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ammonium isocyanate
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Yes, indole is aromatic. This is true. And also completely irrelevent to 497's question. As I said, indole can be alkylates, even though it's
aromatic. Including at the N position, because the nitrogen atom has only two N-C bonds for all intents and purposes. Why the special focus on the
aromatic pyrrole ring? The benzene ring is aromatic too.
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ketel-one
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Ammonium, I love you with all my heart. But I am dumbfounded by your responses.
| Quote: | | Why the special focus on the aromatic pyrrole ring? The benzene ring is aromatic too. |
Forget about the benzene, it's not getting alkylated any time soon, nor does it have any reason to.
| Quote: | | As I said, indole can be alkylates, even though it's aromatic. Including at the N position, because the nitrogen atom has only two N-C bonds for all
intents and purposes. |
For all intensive purposes, there's two N-C bonds most of the time. Sometimes there's three. It's called resonance, because as we agree pyrrole rings
are aromatic.
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ammonium isocyanate
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Sorry if I wasn't clear with my response. The reason I threw that comment about the benzene ring in was because it sounded to me as if you were
saying that indole was aromatic solely because of the pyrrole ring. Again, sorry for the misunderstanding.
Yes, I'm aware of the effect of resonance. However, the nitrogen on the pyrrole ring can be alkylated just the same, after all there's a hydrogen on
it that could just as well be an alkyl group. And so in the end, the possibility of 3 N-C bonds in the pyrrole ring is a moot point, as it behaves as
having 2 all the time (unless you want to drag pKa into this).
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ketel-one
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No it's my fault I wasn't completely correct in what I was saying.
I figured it out, it's not that pyrrole resonates all that much, just that the nitrogen bond with hydrogen is a bit "delocalised" making it harder to
alkylate. But I guess it is possible and may be a by-product of whatever 497 was saying.
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bbartlog
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Do solutions of salts that form crystalline hydrates typically form more stable supersaturated solutions (ones that are less likely to spontaneously
crystallize)? E.g CuSO4 (pentahydrate), Na2SO4 (decahydrate), FeCl2 and so on...
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Paddywhacker
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Pine terpenes
alpha pinene reacts with dry HCl by addition and rearrangement, or by free radical ... I don't know ... to give bornyl chloride.
Where I live, New Zealand, the local pine oil is, apparently, mostly beta-pinene. What is the reaction mechanism and what is the equivalent reaction
with beta-pinene?
Thanks.
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JohnWW
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Just as a matter of interest, how would that ratio of B-pinene to A-pinene and other terpenes in New Zealand pine needle oil, which I presume is from
the very common Pinus Radiata, or Monterey Pine, as distinct from other species, compare with that obtained from trees of the same species in
their home areas of Monterey, California, and Isla dos Cedros, México? What variation with climate is observed? What about such trees grown in
plantations in Chile, South Africa, and Australia, where the species has also been introduced for timber?
If you are talking about addition of HCl or other halo-acid across a double bond on an hydrocarbon such as that in A-pinene, the Markownikoff rule
(1869) would usually be observed, i.e. the H attaches to the carbon that has the fewer alkyl substituents, and the halide attaches to the C with the
more alkyl substituents. A mixture of products may occur when both unsaturated C atoms are equally alkyl-substituted.
http://en.wikipedia.org/wiki/File:Beta-pinen.png
http://upload.wikimedia.org/wikipedia/commons/thumb/7/77/Alp...
http://en.wikipedia.org/wiki/File:Alpha-Pinene_Isomers.svg
[Edited on 14-9-09 by JohnWW]
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DJF90
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I ran a xfire search on this when another member asked about alkylation using bornyl bromide I think... Anyways it appeared that both alpha AND beta
pinene give the SAME (major) product with HBr, with relative stereochemistries (is this a word?) dependant upon that of the starting material. At
least if I remember correctly
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Sedit
International Hazard
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1,2-Dibromoethane
1,2-Dibromoethane can be made by the halogenation of Ethylene glycol but I was woundering if there was anything stoping cheep hardware store HCl from
performing a simular operation albeit lower yeilding. Lower yeilds from a monetary perspective would be acceptible seeing as batch size could be
scaled considerably because I only have 56 grams of NaBr left with 15 grams or so going towards another project. I considered using NaCl+H2SO4 but
then got to thinking if it would work in solution as it is.
Anythoughts?
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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ammonium isocyanate
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HCl would probably work if in the presence of AlCl3 as a promoter. I'm not sure if all that water is a problem or not.
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Sedit
International Hazard
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The H2O proved to help a bit when I performed the Ethylbromide synthesis by keeping the HBr in solution. Due to HCls lesser solubility its level of
fuming can be a bit higher but I don't think the H2O should get in the way of the reaction other then slowing it down to a minor extent due to
dilution. AlCl3 seems like a bit much for performing such a synthesis and a simple copper halide catalyst IIRC should work easier then having the need
for AlCl3.
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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