Author Topic: Iron and nitromethane  (Read 371 times)

Locked

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Iron and nitromethane
« on: October 02, 2009, 07:28:33 PM »
Elusis' write up of how to pull off an iron nitromethane reduction leaves much to be desired. I dont understand how his amount of HCl in the beginning is supposed to keep this reaction going. Actually, I am not quite sure he had ever actually done it. Why he would want the basic mixture spewing methanamine is beyond me.

I overheard some people talking about possible ways of streamlining this reaction and making it easier. They say Hudlicky knows best, and perhaps a mod of page 213, reduction with iron, Reductions in Organic Chemistry with HCl might be the hot ticket.

Would a dual addition of HCl and nitromethane keep this thing cooking and just slightly acidic, with the three part addition of fresh iron?

Could the nitro and HCl be mixed in the same add funnel?

Oh, and "drop a stirbar in" to iron filings... heh.

lugh

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Re: Iron and nitromethane
« Reply #1 on: October 03, 2009, 03:32:10 AM »
The preferred route was posted by Abacus on the Hive, using al-hg reduction of nitromethane in methanol solvent  8)  Iron was discussed, but certainly not perfected  ::)
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Douchermann

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Re: Iron and nitromethane
« Reply #2 on: October 03, 2009, 06:59:04 AM »
As lugh pointed out, there is always the Al/Hg method.  Much less reagent intensive than Fe/HCl reduction of MeNO2.  Only problem is you need a torque-y overhead stirrer.  Eleusis was obviously not the best chemist, but the theory is all there.  The Fe and stirbar might not cause too many problems.  Magnetic attraction drops significantly when the material is finely divided.  I also don't believe MeNO2 is soluble in HCl.  It's lightly soluble in water, and something dissolved would only make this solubility worse.

Locked

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Re: Iron and nitromethane
« Reply #3 on: October 03, 2009, 07:52:30 AM »
I have a "Hive Arc" but the searching is impossible. Does someone actually have it up and mirrored?

People way smarter than me write fancy books with big words and lame pictures so that we might advance the home production of methanamine. What is the netiquette approved naming here? IUPAC? Old School? Whatever? Wichever should have some common chemwords in the spellchecker.

I can tell you I would rather deal with potentially explosive complexes all day then spend 10 minutes with formaldehyde filling a room, not that I have ever done that, twice.

From my brief experience with iron and nitromethane, I say there are only a few points to push this to number one on the list if you can get/distill nitromethane, and I think that is everyone.

First, starter broth of iron, iron chloride, water and some small amount of HCl, much less than Elusis' starting amount, in a flask setup for reflux with mechanical stirring.

Second, the addition of nitromethane to this mix, along with HCl to keep it slightly acidic, the methylamine a salt and the iron rocking, but in a controlled manner, dripping probably, but possibly dripping the nitro and HCl out of different funnels. Needing 4 or 5 necks or a menorah setup triple with claisens but do-able.

Third, fresh additions of iron.

So, the amount of HCl added with the nitro is mol easy or could be monitored by pH. Can nitromethane hang out in a funnel for a while with conc. HCl without something bad happening? I would err on the side of caution and add it separately unless someone here could show me different.

Sure nitromethane reactions can be vigorous, but that helps push to completion. Elusis "Reflux for 12hrs" or whatever nonsense goes counter to all thought. Looking at other reductions of nitro groups with iron, iron chloride and acid or no, that 12hrs is insane. Looks can be deceiving, but nitromethane reacts volcano style fast if you throw in too much with fine iron powder. Not that I have ever done that stupid move. Or thrown DCM into hot freshly basified stuff. Or thrown away 10,000 mag stirrers with filtered trash on accident then had to dig through hazmat because I wasn't going to have to say I threw another magstirrer away, again. Or superheated a mix then hit warp speed on the mag stirrer.

Right, so nitro groups reduce quickly, at least most of the way, as my reading goes. I bet Hudlickey or OrgSyn could be followed close, with the mods I wrote about.

If I get to it I will post results or proof of my stupidity, whatever.

Anyone with pointers, please speak up. Or if you have that bit of Hive Gold and would like to share the details, I'm sure I'm not the only person who would like to read it. I would also like to read the fabled hive works of vacuum refluxing formaldehyde/ammCl. 90% Rhodium? Says who? In 4 hours? Whatever, if it is happening, my test says it is happening slow. In fairness, I did not have the same amount of pressure.

In case you didn't read this the first time and are as stupid as me, DO NOT POUR NITROMETHANE INTO REFLUXING IRON/IRON CHLORIDE/HYDROCHLORIC ACID! Drip... Slowly... Then judge. Not even a "I'm just going to pour in a little to see if this takes off" because it will. It is really sad watching the way a beautiful Ahlinn fills with stuff. You even have a few seconds to ponder how many CFM your vent fan is, what explosion proof motor means, when your fire extinguisher was last charged and whether ABC covers all of the bad shit nitromethane acid vapor is about to throw at you. It actually turned out to be a non-issue, mostly because my gear is pro, even if I am not always. I live to make different exciting new mistakes!

While I was writing this Douchermann posted and I can tell you from experience that nitro reacts with this mix. Perhaps an alcohol might speed things along and get everyone sexy. It helps me mingle. One thing I was wondering about was whether intermediates in the reduction might be less or more soluble, but I would guess more sol because the c# and polar -OH. But I don't know.

jon

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Re: Iron and nitromethane
« Reply #4 on: October 03, 2009, 08:05:50 AM »
Sure nitromethane reactions can be vigorous, but that helps push to completion. Elusis "Reflux for 12hrs" or whatever nonsense goes counter to all thought. Looking at other reductions of nitro groups with iron, iron chloride and acid or no, that 12hrs is insane. Looks can be deceiving, but nitromethane reacts volcano style fast if you throw in too much with fine iron powder. Not that I have ever done that stupid move. Or thrown DCM into hot freshly basified stuff. Or thrown away 10,000 mag stirrers with filtered trash on accident then had to dig through hazmat because I wasn't going to have to say I threw another magstirrer away, again. Or superheated a mix then hit warp speed on the mag stirrer.


so you notice some of his discrepancies ayyeee???
keep reading you'll see more boneheaeded errors.
but i digress this is'nt that hard to carry out in practice just try it and see well you know obvious precations it's exotherm so keep some ice handy but nothing unstable forms should'nt be a problem.
come to think of it swij has been in the practice of reacting ammonium chloride with formaldehyde it takes 6 hours yeilds are'nt the best and it's a pain to work up.
this seems to offer some advantages but swij just sticks to convention.
man i

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Re: Iron and nitromethane
« Reply #5 on: October 03, 2009, 08:26:30 AM »
I just have trouble thinking of all the mercury involved. And if you are getting mercury salts, how tough is iron III chloride? Or hydrochloric? Sure sourcing the perfect 80mesh might be tough, but pure iron powder isnt. And cleaned up iron filings aren't tough to make. Or if you really want to flex nutz you could do like the big boys and deoxygenate rust, I think.

What does one even do with that mercury mess at the end? What kind of insol salt can even start to make one feel good about it? Some crazy high powered sulfuric acid action? I'm sure there is something people should be doing, but I have yet to read, "Oh, and remember, you really are brainfucking your kids and shrinking your balls by throwing this shit down the drain without first forming an insol or finding a hazmat dump."

Clean, easy and fast. Thats what I want. And less mercury in my tunafish.

And more good rolls! What is all this bzpFAKE barac head stuff? LAME! I swear people don't even know good pills anymore.

Oh, and that workup? The methanamine would already be a salt because of our careful monitoring of the pH. Filter, concentrate not to dryness then drip on NaOH for gas. It might even crystallize out, but there is also the FeCl to deal with.

I have dealt with the formaldehyde/amm cl, and paraform depolymer/amm cl, and form/amm cl under reflux, slow distiling, and vac reflux. They all suck. A lot. Vac reflux to start and keep things under control then ambient reflux and slow distil at reduced pressure the best, but this is really splitting hairs. Para routes probably the worst. In the concentrations we are looking for it is a heat with base to get it all dissolved, then what? Neutralize with HCl to 7.? 7.4? All bad. And the fumes! I can't believe people can buy the stuff at stores.

lugh

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Re: Iron and nitromethane
« Reply #6 on: October 03, 2009, 08:55:56 AM »
Mercury is easily amalgamated by iron so recycling it is very simple  8)
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lugh

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Re: Iron and nitromethane
« Reply #7 on: October 03, 2009, 09:09:56 AM »
This old Hive thread explains how to prevent mercury from escaping one's lab:

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Mercury Recovery/Disposal - the Hive BB
the Hive BB
Chemistry Discourse
Mercury Recovery/Disposal

Author Topic: Mercury Recovery/Disposal
ymir
Member posted 08-03-99 02:54 PM

While alternative procedures should always be explored, the reality is that mercury will always be used by some of the bees. As one of the wisest bees recently stated: "personally i believe one must take responsibility for their own waste products... there are numerous books on the safe disposal of lab waste available thru flu/ald/sig et al ......amazon.com etc.... come to think of it ordering books is a good way to START an account with said multi-national corpos.....get one today and bee eco tomorrow....." Mercury containing solutions are easily demercurized by agitation with a 3/1 mixture of copper, nickel or zinc for about 60 minutes, forming an amalgam. When a sufficient quantity of amalgamated metal is accumulated, the metal is solidified in a plastic container for disposal in a landfill [JKTK JP 03 39427 (1991)]. Scrap metal has been similarly used [Rom. RO 84,123 (1984)]. Alternatively, the mercury can be distilled from the metal, if the proper equipment is available. Some references on mercury distillation are: JP 77 35325; USP's 2217410 & 2317814; BR 87 06355 & 89 02284; Jour. Chem. Ed. 65(3), 262 (1988); Jour. App. Phys. 9, 131-4 (1938).The liquid amalgam from the aluminum can be coalesced [Span. 388, 516 (1973)]. Some other references on recovery of mercury from aqueous solutions are: JP K's 73 36091; 73 46594 & 73 63921; USP's 3039865; 3704875 & 4276147. Seperation of mercury from other metals is covered in BP 814862 & JP K 75 142423. A recovery method involving aluminum ions is to be found in Jour. Env. Qual. 1(2), 192 (1972). A refining process from mixtures with iron is covered in JP 55 308. A good general reference is C S Brooks' "Metal Recovery from Industrial Wastes" (1991).
psychokitty
Member posted 08-03-99 04:25 PM

Convert all mercury metal to mercuric nitrate by addition of concentrated nitric acid.
--PK
rev drone
Member posted 08-05-99 06:08 PM

This is a good start. We really need to consider waste treatment issues more seriously. I'm glad to see this dialogue start, especially with regards to my least favorite metal.
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-the good reverend drone

ymir
Member posted 08-05-99 08:28 PM

Some other references with applicability to this matter are: WO 91 04096, using gold or silver impregnated Zeolite A to remove mercury from a fluid. A recovery process is included. A method for removing and recovering mercury from gases is patented in EP 0 179 040. A discussion about removing mercury from gases is found in AIChE Symp. Ser. 71,(152), 16-7; 22-3 (1975). An old method of manufacturing mercuric chloride was to dissolve mercury in an excess of sulfuric acid in an iron vessel, heat until sulfur dioxide ceases evolution, cool, test for the absence of mercurous salts, mixed with salt and placed in glass flasks. A little manganese dioxide was added to ensure oxidation, then the flasks were buried in a sand bath and heated. When water ceases to be evolved, the open tops were closed with thin glass funnels, the sand raked away from the necks, and the heat increased to sublime the crystalline corrosive
sublimate(mercuric chloride). A thorough discussion of the organic compounds of mercury can be found in Whitmore's "Organic Compounds of Mercury" (1921); Goddard's "A Textbook of Inorganic Chemistry" Vol. XI, Part I (1928); "Beilstein's Handbuch der Organischem Chemie" Vol. XVI, pp. 946-78. A discussion of the solubility of mercury vapor in blood is to be found in JAT 5, 327 (1985); Chelation therapy can remove mercury and other toxic metals from the body. Oral chelation agents are a safe treatment method for persons who are at risk for problems caused by toxic metal accumulation. Some combinations available at health food stores are:
1) Alfalfa, fiber, rutin & selenium
2) Calcium and magnesium chelate with potassium
3) Chromium, garlic, pectin and potassium
4) Coenzyme Q10
5) Copper chelate, iron, sea kelp and zinc chelate
EDTA is used intravenously by doctors. Hair analysis can determine if a toxic amount of mercury is present.

Dreamer Envy
Member posted 08-08-99 12:05 AM

Hazardous waste collection facilities are also available. Many state or local agencies operate these facilities as permanent or seasonal collections. Typically , the service is free. Call your State pollution control agency or the local health department locatted in the government listings in your phone book. They asked that it be double bagged and then placed inside a box, taped shut and labeled.
LaBTop
Member posted 08-10-99 07:11 PM

It took some time, but at last some solid facts for stumbling newbee's. Thanks, Ymir. There was allways a lot of concern, but nobody did something about it. Mother Gea will reward you for this, and her rewards are worth collecting.
LT/
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EMOTIONSwill always beFREE!
natrl1
Junior Member posted 08-20-99 03:11 AM

Nothing makes this researcher happier than to see enviornmental awareness discussed here. This researcher lives in a region much like the good rev. drone. Roughly 70% of all lakes and waterways here are seriously contaminated and the fish are inedible. The source of this contamination was found to be largely the result of household batteries being incinerated by municipal waste diposal authorities. In this researcher's opinion, ALL materials are infinitely recyclable (remember Einstein's law stating that matter cannot be created or destroyed just changed), however, it is not always cost effective. Its only a matter of time before the availability of raw materials for any industry becomes so limited that it dose become cost effective to recycle everything... including toilet paper!
This researcher hopes that senior members of the hive would up this topic from just a thread to an entire forum. It would keep the topic visible for the duration.
It's kinda funny that in all of this researcher's travels, its mostly the so called freaks and druggies that so vocally or actively support and/or participate in efforts to these ends. It'll be a thorn in the powers-that-be side to know that the people most likely to save their grandchildren's world are the very same people that they once shunned because of their so called alternative lifestyles. Yeah yeah this researcher is definetly rambiling, but this researcher gets real emotional about such matters. Uptight people suck and most of them are ignorant and have deeeeeep issues. This researcher feels honored to have stumbled upon this forum and to be annonomously associated with some of the the individuals that reside here whom this researcher belives are the vanguards for a revolution of the mind that is so desprately needed throughout the world.
Hail Eris!?
ymir
Member posted 08-25-99 06:53 PM

As no other bee seems capable of contributing much toward this topic, here's a summary of Munro's thesis "Replacement of Metallic Impurities from Water by Metal Beds" (1975): Since the Sung dynasty in China, metallic ion exchange has been known. "The general replacement reaction between a pollutant M1+(aq) and a solid M2(s), is described by the electrochemical equation: nM1+(aq) + mM2(s) = nM1(s) + mM2(aq). Any metal is capable of reducing the ions of any other metal higher in the electromotive series. Generally, the greater the difference in potential, the higher pollutant removal possible. Zinc apparently removed noble metal pollutants (Hg+2, Cu+2 & Pb+2) in 100% efficiency." Thus, it is possible for an individual to effectively remove all mercury ions from solution using zinc. Whether the individual chooses to solidify it in plastic for safe disposal, or to recover the mercury by distillation for reuse is a matter of personal choice, as would be doing nothing but dumping the valuable mercury down the drain. Better understanding of this topic can be acquired by reading the above cited references.
ymir
Member posted 08-31-99 03:52 PM

A few wise words from the above cited Journal of Environmental Quality article:
"Mercuy in the metallic or ionic form is a poisonous pollutant when added to our sewage systems. Solutions containing mercury salts are frequently used in laboratories and proper disposal of such waste is a problem. We have developed a simple method for removing mercury from waste solutions by a chemical displacement reaction. The metallic mercury is recovered, purified and reused. Waste solutions are poured into a glass container containing several strips of aluminum foil and allowed to stand a minimum of seven to eight hours. Aluminum foil was chosen because of convenience and availability, but other metals such as iron or zinc could be used. A transfer of valence electrons from the aluminum atoms to the mercury ions results in the formation of aluminum ions and the free element mercury. The mercury globules can be recovered, purified, and reused while the remaining solution containing the aluminum ions can be poured down the drain with no bad effect. The ability of metals to form ions in solution depends upon the ease with which metals lose their valence electrons. Metals which are more chemically active (valence electrons possess more energy) lose their valence electrons in solution more readily than metals which are less chemically active (valence electrons have less energy). Since aluminum is more chemically active then mercury, the replacement reaction occurs spontaneousy in solution. Aluminum will replace mercury ions in an acid, neutral or basic solution. In this procedure a dilute hydrochloric acid solution is recommended since elemental mercury is recovered without further manipulation. Nitric acid (dilute or concentrated) and concentrated sulfuric acid will oxidize mercury to form mercuric salts. The mercury can be recovered from the aluminum-mercury alloy formed in basic solutions by treatment with hydrochloric acid. The recovered mercury can be further purified by distillation. Mercury pollution of our environment is a serious problem, but there is a second reason that mercury ions should not go through the waste system. The iron and lead in waste pipes and traps are more chernically active than mercury. A transfer of' valence electrons occurs betweern these metals and the mercury ions, resulting in waste pipe deterioration and release of lead into the waste system."
This procedure should be clear enough to allow all interested bees to stop destroying their plumbing, and recover mercury for reuse or disposal. If disposal is desired, the above mentioned procedure of amalgamation onto zinc, and solidification in plastic is recommended. If reuse is envisioned, a thorough study of mercury distillation techniques is recommended.

FMAN
Member posted 08-31-99 06:22 PM

Man murcery suck tons why even contemplate shit like this............ I good for a little acedemic insight that is all. Put mecury into potatoo cook it wrapped in aluminum foil throw away baked potato, not much better than throwing down the drain? But at least they are supposed to monitior shit like this as the landfill is regulated by the governing authorities lets all take responsiblity for accussing who has instigated this procedure! Ok so pour it straight into the drain and i'll but the can test your shit from the dam manhole outside your building and figure you will get busted....... Kinda like lighting off road flares is good idea?????
ymir
Member posted 09-01-99 08:53 AM

Chemists from the USDA and CSU wrote the article. Since they've probably passed away by now, why would one want to know their names? These amalgamation methods can reduce mercury pollution way below 1% in one pass, so what's wrong with them? With Siegfried about to reveal his methods, the bees need to know how to carry them out safely, if so inclined. As far as the Ritter reduction, iron turnings would be best, as iron isn't very soluble in alkaline aqueous solutions. Obviously, for those interested, filtration would not be the best way to recover the mercury. Instead, the solution should be carefully decanted into another container for another treatment, and an amalgamating metal added, for subsequent distillation if recovery is contemplated, or solidification in plastic is disposal is desired. With a couple of treatments, mercury ion levels can be reduced greatly.
Osmium
Member posted 09-01-99 11:56 AM

Good find, ymir. I always believed that all Hg (but a few ppb) is removed by the Al metal in the Al/Hg amalgamation. Now we know for sure.
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There is absolutely no reason why anyone should be polluting the environment with mercury salts when it's so easily recycled 8)
« Last Edit: October 05, 2009, 12:19:14 AM by Vesp »
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Goldmember

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Re: Iron and nitromethane
« Reply #8 on: October 03, 2009, 11:47:12 AM »
That is a horrid colour Lugh!

The info seems useful,so any chance of a more user friendly colour?


Enkidu

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Re: Iron and nitromethane
« Reply #9 on: October 03, 2009, 01:16:49 PM »
My eyes!

+1

Baba_McKensey

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Re: Iron and nitromethane
« Reply #10 on: October 10, 2009, 09:23:43 PM »
See Chemical Abstracts 11, page 1650 Synthesis of alkylamines
Chemiker Zeitung 40, 810 (1916)


Here's the abstract from Chemical Abstracts:

Synthesis of alkylamines. HUGO KRAUSE Chem. Ztg. 40, 810 (1916). -- EtNO2 and MeNO2, which are readily prepd. by a process recently patented (ref. not given) served as the mother substances for the corresponding alkylamines (RNH2). The latter were formed by reducing RNO2 in HCl with Fe. When 2.13 g. EtNO2 in 8 g. H2O, 7 g. Fe filings and 0.8 g. HCl were heated together at 50-60 degrees for 6 hrs. in a flask from which air was excluded, 0.96 g. EtNH2 (about 75% of the theoretical amt.) was obtained. In a similar expt., in which the reaction mixt. was heated for only 3 hrs., the yield was materially
decreased. In these expts. only 1/36 of the amt. of acid required by the following equation was used: RNO2 + 3Fe + 7HCl = RNH2.HCl + 3FeCl2 + 2H2O. Furthermore, the mixts. became alk. long before the reduction was complete, and Fe(OH)2 was pptd. and rapidly oxidized to Fe(OH)3 by the excess of EtNO2. In another expt., RNO2 which remained unchanged when treated with Fe and H2O alone was reduced when small amts. of RNH2.HCl were added to the mixt. It is evident, therefore, that the above equation does not accurately represent the mechanism of the reduction. Apparently Fe reacts further with the RNH2.HCl formed earlier in the reduction, according to the equations 2RNH2, HCl + Fe = 2RNH2 + FeCl2 + 2H. 2RNH2 + FeCl2 + 2H2O = 2RNH2.HCl + Fe(OH)2, and H and Fe(OH)2 are the active reducing agents. Very nearly quant. yields of MeNH2 and EtNH2 were obtained by using 1.5 mols. of HCl per mol. of RNO2 in the reduction, and heating the reaction mixt. at 70 degrees for about 1 hr.

lugh

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Re: Iron and nitromethane
« Reply #11 on: October 10, 2009, 10:31:27 PM »
The original article:
Chemistry is our Covalent Bond

Locked

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Re: Iron and nitromethane
« Reply #12 on: October 12, 2009, 01:22:50 AM »
I love it.

Those "skilled in the art" are left wondering how these old folks were keeping a lid on these reactions. Heat to 70? Then what? Clean the reaction mix off the ceiling?

I do have a dream of seeing this work as beautifully as theory. 75%, hell, 50% in an hour would make me one happy camper.

So to recap, since my google translate german sucks(alt 1729304-5-53 is an a with 2 dots?) and I am really dense...

45g Nitromethane (1 mol) to 152g of 36%HCl(1.5 mol) gets it done according to these old dudes? In 6 hours, or 1?

Later refs tout the virtues of FeCl and looking at the fast track to Fe(OH)2 it makes sense, sort of.

After watching this monster a few times, one does notice that it does not produce a ton of rust as was originally expected. It does however put and odd goldish chroming on the glassware which HCl cleans off easily. Fe(OH)3?

Are they also saying that methylamine stays nicely in 70 deg C basic mix?

I tried a 3 times addition of iron and acid, along with dripping nitromethane. It was a disaster. After hours of babysitting the monster then leaving it to reflux for 6 or 7 hrs, turned off the heat and it kept humming right along. I was sure it was just consuming the excess iron, so in the ice, filter, acidify and vac down to find... FeCl and no methylamine salt. Hmmm

I have easy access to lots of nitromethane, so I will try the germans special recipe. What was the mod that got it to 1hr, just the acid amount? FeCl has got to speed it up, right?

Put something worth trying and I'll do it and write it up.

In other routes, glycine is looking to be pretty cool. I had another hose leak and had to terminate the experiment early, but will be writing it up here as soon as I take it start to finish.

akcom

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Re: Iron and nitromethane
« Reply #13 on: December 06, 2010, 02:53:49 AM »
For that iron reduction I'd suggest keeping the flask chilled.  High temps are going to lead to complex side products you dont want.  Eleusis also mentioned a tin / hcl reduction which doesn't work.  You get the hydroxylamine.

tin and hydrochloric acid, vanadium sulfate, zinc and sulfuric acid, zinc and hydrochloric acid, zinc and acetic acid, lead and acetic acid, iron and acetic acid, concentrated aqueous sodium hydrosulfite at its boiling point, iron and hydrochloric acid, the Adams catalyst and hydrogen, sodium amalgam, aluminum amalgam, electrolytic reductionn.

Theres more than one way to skin a cat
« Last Edit: December 06, 2010, 03:04:18 AM by akcom »

akcom

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Re: Iron and nitromethane
« Reply #14 on: December 06, 2010, 03:23:29 AM »
Sorry to bring up a dead topic, but this was something I was looking into recently.