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jhonthebaptist
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cadaverine
I have been trying to log in for a few weeks, it appears I forgotten my password so I made a new account.
I have spent much time devoted to making a famous cyclic secondary amine from various sources. I settled on the decarboxylation of lysine to produce
cadaverine dihydrochloride and
cycilize that by strongly heating with direct flame.
The results were disappointing. From 50 grams lysine about 15-20 ml of cadaverine were produced. (yellow thick oil) I neutralized with dil. hcl to
make the hcl salt and evap. to dryness. Then strongly heated this salt (200 C -- 250 C). Copious white smoke was produced as I thought ammonium
chloride would sublimate. After it cooled down was then Ph adjusted to alkaline with sodium hydroxide in isopropyl alc. (75% alco. 25% water.) The
mixture was then distilled., at the end vacuum was applied. I smelled ammonia so I assumed the reaction must have produced (some) of what I wanted.
After distillation the alcohol amine mixture was again neutralized and evaped to dryness. When the brownish/off white
yellowish salt was reacted with other reagents it failed to work as expected. SO Im gonna put this to bed right now. This method of production for
the sec amine is not practical at all.
[Edited on 28-1-2015 by jhonthebaptist]
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Bert
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Mood: " I think we are all going to die. I think that love is an illusion. We are flawed, my darling".
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What was your old user name?
Rapopart’s Rules for critical commentary:
1. Attempt to re-express your target’s position so clearly, vividly and fairly that your target says: “Thanks, I wish I’d thought of putting it
that way.”
2. List any points of agreement (especially if they are not matters of general or widespread agreement).
3. Mention anything you have learned from your target.
4. Only then are you permitted to say so much as a word of rebuttal or criticism.
Anatol Rapoport was a Russian-born American mathematical psychologist (1911-2007).
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jhonthebaptist
Daddy, can you cut his head off, just for me? Pretty please, daddy... On a nice platter?
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was pickardjr, bert.
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CuReUS
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Quote: Originally posted by jhonthebaptist  |
I have spent much time devoted to making a famous cyclic secondary amine from various sources. I settled on the decarboxylation of lysine to produce
cadaverine dihydrochloride and
cycilize that by strongly heating with direct flame.
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where you trying to make piperdine ? I didn't know piperdine could be made by strongly heating cadavarine ? do you have any literature for the
reaction ?
here is a good video to make cadavarine
https://www.youtube.com/watch?v=V4D5aTNYalQ
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jhonthebaptist
Daddy, can you cut his head off, just for me? Pretty please, daddy... On a nice platter?
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[Edited on 29-1-2015 by jhonthebaptist]
[Edited on 29-1-2015 by jhonthebaptist]
[Edited on 30-1-2015 by jhonthebaptist]
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jhonthebaptist
Daddy, can you cut his head off, just for me? Pretty please, daddy... On a nice platter?
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[Edited on 30-1-2015 by jhonthebaptist]
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Etaoin Shrdlu
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| Quote: Originally posted by jhonthebaptist | | Yes Cureus, I was attempting a piperidine synthesis. I wanted to see who would recognize what I was doing, looks like you are the only one that did.
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Everyone else ignores ambiguously phrased drug-related synthesis questions.
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jhonthebaptist
Daddy, can you cut his head off, just for me? Pretty please, daddy... On a nice platter?
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[Edited on 30-1-2015 by jhonthebaptist]
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smaerd
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So, how awful does cadaverine smell?
Edit - Again considering the thread title was about cadaverine it would be nice to see what your conditions were for the decarboxylation.
[Edited on 30-1-2015 by smaerd]
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jhonthebaptist
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Well after etaioin posted that remark about drug cookery , I dint think anyone wanted to know what my procedure was or conditions of the reactions I
posted. I undertook this project to find out IF it could be done, that is to make piperidine from cadaverine. I have experience with piperidine from
many years and if I really wanted to buy it I could get it by the gallons. So please don't accuse me of illegal activities.
One would need to decarboxylate 5 pounds of lysine to get enough cadaverine to get the reaction to produce any workable amount of piperidine the way
I did it.
I used an old 500 ml boiling flask with a stopper and a bent length of pyrex tubing, it was tilted to the right at about 2-3 o'clock. The tube ran
into a 50 ml flask in ice. The lysine was mixed with sodium bicarbonate and dumped into the flask. The size of the rxn was limited to 10-20 grams of
lysine because any bigger and reactants wouldn't be all used and would waste alot. At first the mixture is white as heat is applied from a bunsen
burner it turns black, then grey, the cadaverine dont smell like dead bodies. It smells like the amine used in epoxy kind like jb weld in a way.
However it has a strong smell that is nasty to be around for some time.
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Etaoin Shrdlu
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| Quote: Originally posted by jhonthebaptist | | Well after etaioin posted that remark about drug cookery , I dint think anyone wanted to know what my procedure was or conditions of the reactions I
posted. |
Noooooooooooo. I didn't mean it that way, okay? Exactly the opposite. Your initial question was phrased to deliberately avoid mentioning the product
by name, and that makes a question look more shady than scientific. If you look around the board you'll find all kinds of drug-related synthesis
threads. They get a better response if you're forthright about what you're working on.
I personally don't care in the slightest whether you or anyone else is cooking drugs.
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Darkstar
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What's with all of these edited-out posts? Looks preeeeeeety suspicious if you ask me.
Just kidding. Seriously, though, even if you were up to no good, no one ever really makes a big deal out of it as long as you at least show
some genuine interest in the actual chemistry involved.
[Edited on 30-1-2015 by Darkstar]
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jhonthebaptist
Daddy, can you cut his head off, just for me? Pretty please, daddy... On a nice platter?
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ok no problem. If thats how it appears than thats an assumption the reader makes, wasn't my intent to look suspicious , or be sub-verse. I see quite a
bit of flaming on this forum, from various posts, some have merit while others have none. I have never come here asking HOW to do anything, or to get
any items. I am interested in actual chemistry and have gone to school for that subject. I may be in the wrong place, for actual science and get the
impression most people are not welcome here.
If I cant be welcomed as a member then I will not stay.
[Edited on 30-1-2015 by jhonthebaptist]
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Zombie
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Dude... I'm an idiot, and they have been very understanding with me. Just sayin'
I'm aware of what piperidine is, and it's use but I took note at the cadaverine. I'd be interested in following this if you stick around.
It's obvious (as you stated) you can't make enough piperidine to make this worth the effort.
They tried to have me "put to sleep" so I came back to return the favor.
Zom.
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jhonthebaptist
Daddy, can you cut his head off, just for me? Pretty please, daddy... On a nice platter?
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Thanks zombie, This has gone as far its gonna go though. I mean I dont intend to even make anymore cadaverine or piperidine from it. There is a video
on youtube of the cadaverine synthesis from lysine. The only thing I did was scale it up and did three separate runs, totaling 50 grams lysine and
about 24-25 grams of sodium bicarb. Use a flask instead of a test tube.
Take note , it makes a mess of the flask. alot of tar and crap Most will come out when cleaned but not all, and the stresses it puts on the glass
makes the flask almost unfit for much else. It is easy, just got to be safe when working with high temps and glass, wear eye protection if you do.
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blogfast25
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In most cases of tar it will dissolve in hot, 20 - 30 w% NaOH with some detergent mixed in. A combination of chemical cleaning with mechanical
abrasion will get rid of the junk. Superficial etching doesn't render glassware unusable either.
[Edited on 31-1-2015 by blogfast25]
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smaerd
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Thanks for the experimental. I've always been interested in decarboxylation reactions of common chemicals. Believe it or not I was considering using a
cadaverine type linkage in a project that's why I asked. Interesting to hear that it doesn't smell as awful as it is often reported to be. I can
actually see a good amount of interesting chemistry coming from this compound in a DIY setting so I'm glad you made this thread all the banter aside.
If I were to recreate it, I'd do the old coffee can disposable destructive distillation rig, as done in benzene from sodium benzoate synthesis.
Honestly I don't think anyone cares what you plan to use the intermediates for. I think it's a little rude to speculate unless well its one of those
ridiculous precursors to an illicit substance. I can comfortably say that I wish I had piperidine around many times, and if someone can't think of a
legitimate reason why that might be they are probably cooks themselves.
I do have a suggestion though. Maybe for your next post to avoid scrutiny, share more of the chemistry/experimental, and less of the things you maybe
aren't so eager to share. Everyone here loves to see an experiment especially one that worked.
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Darkstar
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For the record, I don't honestly believe you're doing anything illegal. And even if you were, who cares? I surely don't. This is a forum about
science, not politics.
Piperidine has plenty of legitimate uses and there's nothing wrong with trying to synthesize it, even if it's just for the hell of it. That's what
amateur chemistry is all about. Which is also why you should have just come out and admitted what you were trying to do in the beginning and moved on.
Between the ambiguous "famous cyclic secondary amine" line and you getting all defensive and deleting your posts, is it really a surprise that someone
thought your thread looked a little shady?
Anyway, I do look forward to reading more about your experiment. 
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jhonthebaptist
Daddy, can you cut his head off, just for me? Pretty please, daddy... On a nice platter?
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I agree and darkstar you are right, Im sorry for the word drama. You put the situation in perfect perspective , it was just for the hell of it. thanks
for the support, I hope to contribute as much as I can.
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CuReUS
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but why did you delete your posts,what did you write in them that was so incriminating ?
also,I cant understand how you would get even a bit of piperidine,pls post the reaction mechanism or the lit-sup.
| Quote: | | Piperidine has plenty of legitimate uses and there's nothing wrong with trying to synthesize it, even if it's just for the hell of it.
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piperidine is in the list 1 of DEA,I think that means its illegal to possess of manufacture without permit
| Quote: | If you look around the board you'll find all kinds of drug-related synthesis threads. They get a better response if you're forthright about what
you're working on.
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that is so nice,so could someone please tell me why safrole is converted to isosafrole
This question has been bothering me for a long time.Is it done to prevent polymerisation due to storage ?
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turd
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| Quote: Originally posted by CuReUS | | piperidine is in the list 1 of DEA,I think that means its illegal to possess of manufacture without permit... |
...in some parts of the world, that are irrelevant to many of us (myself included).
| Quote: | | that is so nice,so could someone please tell me why safrole is converted to isosafrole |
So that oxidation gives you the phenylacetone and not the phenylpropionaldehyde. The smell is also (very) different.
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Zombie
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I have to point out here fellas the a very large percentage of the forum is involved with compositions that are frowned upon.
Perhaps the matter is best suited for the forum management rather than the members.
Besides, who's to say the fella really did any of what he said he did. Could be my grandmother passing time, and stirring up cr@p like always.
Oh... nobody in the thread mentioned Safroil.
Just sayin'
[Edited on 31-1-2015 by Zombie]
They tried to have me "put to sleep" so I came back to return the favor.
Zom.
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blogfast25
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| Quote: Originally posted by Zombie | I have to point out here fellas the a very large percentage of the forum is involved with compositions that are frowned upon.
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A very large percentage?
Frowned upon by whom? The yokels in your local police station in Florida?
What's done here is either legal or it's not. In the former case let them frown themselves into an aneurysm.
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Zombie
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Sometimes sir... I wish. Forgot, we are the home of the worlds smallest police station. Guinness book
[Edited on 31-1-2015 by Zombie]
They tried to have me "put to sleep" so I came back to return the favor.
Zom.
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The Volatile Chemist
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It's the 'energetic Materials' Section which is frowned upon. It's title is soooo funny, as it obfuscates what's actually going on inside  When I first joined SM, I just thought it meant 'dangerous chemicals' 
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