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Author Topic: Re; Hydroxylamine  (Read 757 times)

lugh

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Re: Re; Hydroxylamine
« Reply #40 on: October 03, 2011, 12:08:06 AM »
Quote
I put in a request for the article I believe to be the one a guy named Preibisch published in the late 1800's detailing his findings that a primary nitroparaffin heated with a mineral acid will give the corresponding acid salt of hydroxylamine and some other stuff. If I can get this paper or any paper that details the procedure Alice did, maybe I could replicate the results, but I don't have enough right now to do it.

The page containing Preibisch's article is attached, and the article by Lippincott et all which was already uploaded in:

http://127.0.0.1/talk/index.php/topic,2594.msg26278.html#msg26278

and

http://127.0.0.1/talk/index.php/topic,2556.msg26265.html#msg26265

is included so hopefully the third time that the article is uploaded to this web site doesn't escape anyone's attention ever again   ::)  You need to vent the carbon dioxide outside like Alice did   :-X  The patent he used as his guide is attached as well  8)

« Last Edit: October 03, 2011, 12:51:17 AM by lugh »
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reDEEMed

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Re: Re; Hydroxylamine
« Reply #41 on: October 03, 2011, 02:50:51 AM »
Damn, thanks a lot lugh! I actually did search for them here, I just didn't have any luck. I was betting on atleast one of the refs to have the name Preibisch in it somewhere, now I see none do. I have found so many in the last couple days, some really really good ones, just not that particular paper I requested.

Attached is one that I considered to be one of the best because it's old like the Preibisch paper and the writing style was just easier for me to follow. He talks about every detail of this work including, in detail, how things were tested for etc. Very nice read.

Contribution To The Study Of Hydroxylamine And It's Salts - W. H Ross Dalhousie University Halifax N. S.
Can't find a copy pasta summary. Another guy on a quest to make every conceivable acid salt outta this shit. What makes this paper better is how the author explains in detail how to test for the desired compounds at the end of each example as well as outlining a procedure they used to calculate yield without actually having to recover, purify and weigh the product from each reaction.

Not really sure of anybody else's interest level, but I have a lot of good refs on this subject. I'll straight up dump if I get the feeling somebody wants them.

Edit: Thanks to you too, RoidRage. When do you plan on giving it a try? Whenever you do I hope you post about it!
« Last Edit: October 03, 2011, 03:46:24 AM by reDEEMed »
"Ego is a structure that is erected by a neurotic individual who is a member of a neurotic culture against the facts of the matter. And culture, which we put on like an overcoat, is the collectivized consensus about what sort of neurotic behaviors are acceptable."
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lugh

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Re: Re; Hydroxylamine
« Reply #42 on: October 03, 2011, 08:47:54 AM »
Quote
Damn, thanks a lot lugh! I actually did search for them here, I just didn't have any luck. I was betting on atleast one of the refs to have the name Preibisch in it somewhere, now I see none do. I have found so many in the last couple days, some really really good ones, just not that particular paper I requested.

The patent was mentioned in:

http://127.0.0.1/talk/index.php/topic,2594.msg26275.html#msg26275

which is the other thread you started on the same subject  ::)  You'd bee much better off if you read more and posted less  ;)  A lot of bandwidth is being wasted over this simple molecule  :P   The end results from the effort applied  8)
Chemistry is our Covalent Bond

RoidRage

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Re: Re; Hydroxylamine
« Reply #43 on: October 03, 2011, 11:37:53 AM »
Quote from: reDEEMed on October 03, 2011, 02:50:51 AM
Thanks to you too, RoidRage. When do you plan on giving it a try? Whenever you do I hope you post about it!

Soon enough, hopefully. I have many projects on my mind (and hands :D ) right now. I'll be sure to report back here once I'll give it a try!

reDEEMed

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Re: Re; Hydroxylamine
« Reply #44 on: October 03, 2011, 12:06:40 PM »
lugh, this simple molecule is actually fully of surprises. It's anything but simple. I didn't start this thread, this is hypnos' thread. I forgot about the other thread, to be honest. My brain is at full capacity right now. I'm surprised I havent pulled a muscle in my brain yet. You'll have to forgive me if I don't make perfect use of the bandwidth here, I got a lot going on.

I'm still translating the Preibisch paper. Not sure how long that will take, but I'll work on it till it's done and share with whoever wants it. It's not so much translating the words as it is figuring out wtf the author means. I'm a bit rusty on my 19th century German. I got the first few sentences done. 10 minutes to translate the words into english, 45 minutes to rearrange those words into a coherent sentence.
"Ego is a structure that is erected by a neurotic individual who is a member of a neurotic culture against the facts of the matter. And culture, which we put on like an overcoat, is the collectivized consensus about what sort of neurotic behaviors are acceptable."
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reDEEMed

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Re: Re; Hydroxylamine
« Reply #45 on: October 06, 2011, 10:11:20 PM »
Incase anybody is interested, I had someone help me with translating the documents posted. Here is a partial, rough translation, thanks RoidRage and lugh.

Quote
Mr. Victor Meyer recently reported in the Berlin Chemical Society (Volume 15, page 1169) on the behavior of /reaction of nitroathans in sulfuric acid. This leads me to report my findings, which I will publish shortly in this journal, from last summer (made in) the laboratory of Professor Kolbe with the homologous (no idea) Nitrocarbol. In the articles I discuss a remarkable observation about the Verendung(?) who _____ the Nitrocarbol by sulfuric acid.

This process proceeds very smoothly by using the following equation.
"Ego is a structure that is erected by a neurotic individual who is a member of a neurotic culture against the facts of the matter. And culture, which we put on like an overcoat, is the collectivized consensus about what sort of neurotic behaviors are acceptable."
— Terence McKenna

RoidRage

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Re: Re; Hydroxylamine
« Reply #46 on: October 06, 2011, 10:24:36 PM »
It's more than readable. Post the rest once you're done translating it if you can :). By the way, did you try forming an oxime with the crystals you recovered when you ran the reaction?

reDEEMed

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Re: Re; Hydroxylamine
« Reply #47 on: October 06, 2011, 10:47:07 PM »
Not yet. I still have a crop of the sulfate crystals to remove from the jar. Maybe after that I'll have enough to feel worthwhile to experiment. As often happens with me, I get side tracked and busy with another project. Right now I'm building a set of totes with molded foam for all of my glass. I'll make a thread when I'm done. I'll be back on some oximations in the next couple days. Plus I'm a bit sick since my morphine ran out. I don't get another refill till tuesday. So, till tuesday I'll be taking lots of shits and generally feeling rough. The downside of opiates is the physical dependance. They let me live a normal life with all the hardware in my back, but when I dont have them, yuk.
"Ego is a structure that is erected by a neurotic individual who is a member of a neurotic culture against the facts of the matter. And culture, which we put on like an overcoat, is the collectivized consensus about what sort of neurotic behaviors are acceptable."
— Terence McKenna

Tsathoggua

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Re: Re; Hydroxylamine
« Reply #48 on: October 07, 2011, 04:10:32 AM »
I can sympathise with that, redeemed. I'm in the same boat as a chronic pain patient. Just been speaking to my doctor today about that actually, hopefully coming off dihydrocodeine and transferring to bupe. Not to taper off, but for its long duration of action, as DHC leaves me waking up in WD at night/early in the morning.

Taken to shooting methoxetamine instead of my DHC actually though, which is MUCH better, at least, for me, as a painkiller (regular opioids are not very good for neuropathic pain, and after a botched surgery on my knee I have to deal with that also, in addition to the tendonitis and joint pain), actually, I've found that MXE will in and of itself maintain me as far as its opioid effects go. And of course, shooting the stuff means it acts in just about the time it takes to do a slow IV push from a 2ml rig, rather than waiting about a half hour before I can bugger off back to bed (I do not DO mornings)

Its the devil's bargain, opioids are. On one hand, stuck without them, on the other, I'm chained to having to have a supply around, having been on the DHC for a good few years. Can't wait until my 3g of methoxetamine turns up tomorrow though. I know what I will be doing as soon as the mail man drops that package off, Oh boy, the IV kit is going to get broken out and a rig filled quicker than you could say 'eyeballs vibrating' :D

Hopefully my tolerance to the dissociative effects will have gone down, thanks to starting pramiracetam recently. Nothing like 'racetams to quickly re-regulate one's NMDA receptors after a period of extensive antagonist use.
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dingbow

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Re: Re; Hydroxylamine
« Reply #49 on: December 11, 2011, 03:46:42 AM »
Alright so heres my experience with the sulfate variety, based on the text "Action of Mineral Acids on Primary Nitroparaffins":

First run 20ml nitromethane was brought to reflux and an equimolar amount of sulfuric acid (92%) was dripped in fairly slowly. Reflux was continued until I decided to scale it up (probably not the best idea at this stage) with the addition of 30ml more nitromethane being added at once, then an equimolar amount of sulfuric acid was dripped in once more. This was refluxed for 8hrs, at the end of which I could clearly see 2 layers, the top layer I assume was unreacted nitro. Regardless I decided to pour the reaction into twice its volume EtOH to precipate the sulfate. Unlike the hydrochloride variety this started occuring immediately with large crystals growing in the beaker fairly rapidly. It was left in the freezer overnight and was filtered the next day to give 34g of sulfate (44% molar yield if im not mistaken).

Second run 50ml nitromethane was charged into an RB with an equimolar amount of sulfuric acid. Stirring was commenced, but unlike the text this did not cause any noticable exothermic reaction (nitromethane less reactive then nitroethane?). This mixture was brought to reflux and held there for 8hrs. At the end of this, the mixture was homogeneous. Again it was poured into EtOH which caused such a rapid precipation of the sulfate that it did not form large crystals, but tiny needles that look very similiar to a certain amide. The sulfate from this reaction weighed in at 74g but was fairly damp. It was then recrystalised from a H2O/EtOH mixture, filtered and dried to yield ~50g of an off white sulfate (65% molar).

A few things I want to note:
-I personally prefer this to the hydrochloride methods as far as yield, time and ease is concerned.
-CO generation is very real and MUST be vented outside, I experienced mild CO poisoning in the second run. This was a real wake up call. the last thing you want is to have this run overnight and for you not to wake from your sleep.
-the sulfate does not seem to be hygroscopic like the hydrochloride.
« Last Edit: December 11, 2011, 03:48:47 AM by dingbow »
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