Author Topic: For the vindication of Eleusis - Methylamine  (Read 22539 times)

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Vaaguh

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Re: The flask was then cooled to room ...
« Reply #40 on: May 12, 2004, 01:43:00 PM »

The flask was then cooled to room temperature and the solids were filtered.




Where these solids recrystalized with IPA aswell or discarded ?

Finally after 30 hours of slow distilling the distillate has reached the >60° celcius mark.

Unfortunately it will be a couple more days before the IPA will arive and the extraction can be performed.




Vaaguh

  • Guest
the good ole "parts"
« Reply #41 on: May 12, 2004, 07:20:00 PM »

17 parts of 40% formaldehyde, 7 parts of 96% alcohol and 8 parts of ammoniumchloride




Just for clarification purposes these parts can be converted into molar ammounts right?

(1 mol formaldehyde : to 1,176 mol ammonium chloride)




Organikum

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Parts are always weight.
« Reply #42 on: May 12, 2004, 08:15:00 PM »
Parts are always weight.


Vaaguh

  • Guest
finished
« Reply #43 on: May 15, 2004, 08:33:00 PM »
Alright everybody thanks for all the help the procedure seems to have worked niceley.

In a 500 ml RBF equiped with a reflux condenser containing 50 g (0,36 mol) hexamine and 10 g ammonium chloride there was added 60 g denatured EtOH diluted with 60 g H2O. While the whole was being stirred 142 gram (1,43 mol) 37% HCl was slowly added which caused a little bit of white smoke travel up the condenser, during the initial stirring a little heat was evolved after no more heat evolved the mixture was slowly heated on a water bath to 40 °C causing all the solids to dissolve after 1 hour the temperature was increased to 50 °C, 2 layers where noticed.

After 2 hours the wather bath was switched for an oil bath and the mixture was slowly heated to 75 °C this caused the solution to boil. After 2 hours of refluxing the condenser was switched for a vigreux column and fractions where collected in the range of 40 °C to 55 °C. After 8 hours of distilling the solution stopped boiling and no more distillate came over the bath was heated further to 85°C and fractions between 45 °C and 60 °C started to come over at around 2-3 drops per minute, another 6 hours later the mixture stopped boiling causing no more distillate to come over.

The mixture was heated to make it boil again which was at 100 °C. The distillate came over at a annoying slow pace of around 1 drop per 1-2 minutes and the solution started to turn brown and the only fractions that came over where between 40 °C and 45°C.

Another 12 hours later it was decided that the droplets came over too slow and the vigreux column was switched for a normal still head the now orange reaction mixture was heated to 80°C and altough the reaction mixture did not visually boil there was distillate comming over between 45 °C and 65 °C over. At the around the 4th hour point the distillate reached 65 °C the heat was turned off and the solution was cooled down to 15 °C, the solids where filtered off.

About 30 g of white fluffy powder was collected and the remaining liqour was vacuum distilled to give orange tinted crystals. The slightly wet crystals where extracted and recrystalized with warm IPA to give beautiful almost transparent crystals (which is hopefully methylamine hcl).

The crystals still need to bee dried to calculate the yields.

From now on a vigreux collumn will not be used again.

Probally the best way is to slowly increase the heat of the reaction to 75 °C over a 4 hour span and reflux the solution for another 2-3 hours. From there switching the condenser for a a still head while maintaining the heat at 75 °C or to 85 °C at most even if things stop boiling dont heat things up but allow the distillate between 40 °C and 65 °C to come over. When the distillation is finished between that range reflux the mixture for 2 more hours, cool down, filter, extract and recrystale.

Btw. Seeing how dimethylamine is soluble in chloroform perhaps for making the cleanup more easy would it perhaps be an idea to use the stochiometric ammounts 20 HCOH + 9 NH4Cl + 10 C2H5OH as a ratio or would this mess things up?


armageddon

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explosive by-product?
« Reply #44 on: June 10, 2004, 01:04:00 AM »
Tested, works good!

I'm not sure about the insolubles after reflux: Could it be that soemthing like hexamethylenetriperoxidediamine or HMTD (powerful primary explosive!  :o ) is formed?

I ask because I know that HMTD can be prepared using fuel tabs (AKA hexamine), a strong oxidizer and a weak organic acid in aequous solution, and that it is insoluble in almost everything (not in boiling alcohol, nor in acetone) - which are exactly the properties of this white, hard clumpy substance that was filtered from the rxn mixture....

(NO, the substance is NOT unchanged hexamine - dil HCl does nothing to it, And I KNOW, there are no strong oxidisers present, but it is the only substance i know derived from hexamethylenetriamine - and being that INSOLUBLE..  ;) )

greetz A


Bond_DoubleBond

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not to worry . . .
« Reply #45 on: June 11, 2004, 03:39:00 AM »
...it's probably just wax and other binders from the hex (if you're using fuel tabs).  although swim has run amcl/paraform reactions and gotten small pebbles of insolubles.

also, for anyone having difficulty with this reaction, after the formate is distilled off hold the mix at 85-90c, otherwise the imine reduction does not take place.

swim ran three reactions a couple of days ago at 1/4 vogel scale with paraformaldehyde, amcl, and denatured alcohol.  the first two were stopped after the formate was distilled off, and the third was held at 90c for an hour afterwards.  the first two had an off white hue with _hints_ of yellow and blue.  the third was a pale defined yellow.  the amcl was separated from each.  near all amcl was recovered from the first after separation, distillation, etc., and most from the second upon the first filtration.  52g (92%) methylamine hydrochloride was recovered from the third reaction, none from the first.  the removed amcl was added back to the second, and the mix was heated to 90c and held there for an hour and 53g meam.hcl (94%) was recovered.

good call abolt.

abacus

  • Guest
food for thought
« Reply #46 on: June 11, 2004, 01:03:00 PM »
While we are on the subject of methylamine syths that actually work in practice, I draw astute readers to the following syth that DOES NOT work thereby allowing newcomers to avoid making such errors.

Org you posted the following ref in your post numbered 410425 (how do I get that to link again??).  

I put it to the court that the following words by K.C Nicolaou are bullshit (which is not your fault Org).



K.C. Nicolaou  posted 12-02-1999 12:28 AM
                      ---------------------------------------------------
                      I think that Sumerian was full of shit on that
                      one. He didn't remove his NH4Cl. Excess HCl does
                      not pose a problem for this rxn, although not
                      having enough is a problem. Vacuum has no other
                      effect than to make temp regulation easier, to
                      dispell another myth.
                      However,
                      Maximum theoretical yield from 140g Hex = 270g
                      MeAm HCl
                      Ways to *theoretically* increase the yield of MeAm
                      HCl would be allowing the rxn to run for a longer
                      amount of time, refluxing rather than allowing
                      vapors to escape, having less water present(you
                      need some, just not too much), and addition of
                      excess NH4Cl to your hexamine/HCl rxn.
                      Using the ratio of reactants
                      140g Hex
                      135g NH4Cl
                      110mL 31.45% HCl
                      100ML dH2O
                      and heating at 100C with a reflux condensor for
                      ~24hr gives yields of up to 210g of MeAm HCl(78%)
                      after chloroform wash and 2x recrystalization from
                      dry IPA. At this dilution your condensor can get
                      plugged by solids crystalizing out on the cold
                      surfaces(I don't know if that's from splashing of
                      the sol'n or a sublimation/evaporation type of
                      thing). SWIWIWN (Someone Who I Wish I Was Not) had
                      a rxn do that and then blow ~200g of stinky-ass
                      Methylamine all over the ceiling, breaking a
                      condensor and a thermometer(luckily it was the
                      only non-mercury unit in the room). Watch out.
                      Also, before someone says some stupid shit like
                      "doood, you don't have to add that extra NH4Cl," I
                      know, you don't. But, it increases the yield per
                      amount of hex, suppresses DiMeAm formation, and is
                      all recycled after the alcohol
                      recrystalizations(which you HAVE to do) anyway. So
                      I do it.

As very experienced hand at making methylamine.hcl via hexamine and HCL, SWIM initially noted that you can not replace HCL ions by simply adding NH4CL, as the HCL needs to be added to hexamine in the right molar ratio of 4:1 to get the desired amount of formaldehyde and NH4CL that the reaction requires.  The molar ratios above are clearly wrong.

Even though SWIM was skeptical, experiments using the above ratios were carried out which indeed proved worthless; there was very little resulting formaldehyde in the reaction flask and a huge excess of NH4CL, not to mention the often talked about smell (which incidentally doesn’t occur in a proper hexamine and HCL reaction).   The amount of methylamine.hcl that was finally recovered was insignificant.

The conclusion that SWIM made was, that clearly K.C N was talking bullshit or had made a mistake in the amount of HCL added to the flask. 

One other point, adding 30-35% HCL to hexamine DOES NOT cause the NH4CL to precipitate out.  What happens is it that it dissolves into a clear solution (slightly exothermix), upon heating (without ethanol) the clear solution sometimes becomes cloudy and sometimes it does not.

SWIM is looking forward to experiments with adding ethanol to increase yields if he ever has access to a lab again.

Abacus

abolt

  • Guest
Thought food is yummy
« Reply #47 on: June 12, 2004, 05:40:00 AM »
Abacus, that is slightly misleading.

Whilst I have no comment to make on KCN's explanation of the reaction I think you will find that KCN states further along in that thread that a much greater portion of HCl is required.(A 440 ml amount, if I remember correctly)

Go back and check it out. ;)

BDB, good work.

FWIW, I think that the reaction that Orgy is talking about in this thread is nothing but a fandangled, arse about version of the one listed in Vogels with the exception that Hexamine and HCl are used instead of Formaldehyde and NH4Cl.

The only benefit from the addition of Ethanol, is that it removes any excess Formaldehyde at a lower B.P. as Ethyl Formate, thereby eliminating any chance of the Di or Tri (methylamine ) forming.

The added benefit of the NH4Cl is that by reacting it with excess Formaldehyde, the yield is increased. If formate is distilling over then that means that there is even more Formaldehyde to be taken advantage of.

By adding even more NH4CL(see the thread mentioned by abacus above), could we increase yields of Methylamine even further???????

In discussions with bees I have learned that some have had success with this synthesis using a vigreux column and failures when not using a vigreux column.

The more commonly known literature tells us that Methylamine is formed in best yields at 103 - 104 Celcius internal reaction temperature via the NH4Cl/Formaldehyde route and at 105 -110 internal reaction temperature via the Hexamine/HCl route.

Has it dawned on any of you guys that when you are distilling the formate portion at the top of a vigreux that the internal reaction temperature is what is forming the Methylamine and not the rate of Formate distillation????????????

This could also explain why reactions without a Vigreux have failed, due to the less heat required to force distillation, thereby lowering the internal reaction temperature, disallowing methylamine production to commence.

I have a strong hunch that methylamine can be made in good yields with simple or even (ghetto) equipment.

There is any easy and simple way to find this out.

Could someone please try the following?

* Using the same ratio of reactants as Orgy stipulates at the start of this thread. Set up a standard distillation rig and place a thermometer in the oil bath only and slowly raise the oil bath temperature, and collect any distillate that comes over.

* When the oil bath reaches anywhere between , say, 106 - 109 Celcius, hold the temperature and allow the reaction to stir for 3 - 4 hours.

* Add vacuum and raise temperature to drive of the rest of the aqueous portion.

* extract MeNH3Cl with hot IPA or MEOH and cool down to recrystallise.

If my hunch is correct then we could add increasing portions of NH4CL until no formate is collected. Thereby maximising yields, and putting this baby to rest. :)


abacus

  • Guest
abolt, I'll check
« Reply #48 on: June 12, 2004, 01:04:00 PM »
Abolt, I  must have missed the correction by KCN, sorry about that I thought i had the whole thread and had no knowledge of a correction.

Good methylamine.hcl is not that hard at all, in fact, really simple using hexamine (solid camping fuel tablets)and HCL.  

I also go so far to say from experience that the reaction occurs below 103-104DegC.  The reaction (without ethanol) starts at about 80DegC and further heating in a hot water bath so that the flask temperature hovers around 95-100DegC works like a charm (which is not the method org suggest using ethanol).

Abacus

Organikum

  • Guest
Re: FWIW, I think that the reaction that Orgy...
« Reply #49 on: June 12, 2004, 02:22:00 PM »

FWIW, I think that the reaction that Orgy is talking about in this thread is nothing but a fandangled, arse about version of the one listed in Vogels with the exception that Hexamine and HCl are used instead of Formaldehyde and NH4Cl.



The reaction I talk about here is from a patent and was first proposed by Eleusis. It was new enough that the IG-Farben got this patent granted, so I guess it is not a "fandangled arse about version" but something different. What you think is actually not important, important is that it works fine and produces better yields in much shorter time than the method proposed before (the one outlined in Vogels 3rd). There is no difference if formaldehyde and ammoniumchloride or hexamine and HCl are used. Read the thread and you MIGHT be able to realize this.
I used hexamine because I HAVE it. Thats the only reason and I told it.

abolt, find something better and post it, or fuck the shut up, ok? I have the impression that quite a lot of bees like this "fandangled arse about version" very well and I cant understand what you complain about if not your own incapabilities.

regards  :P
ORG




armageddon

  • Guest
Abolt: firstly the reaction temperature will...
« Reply #50 on: June 12, 2004, 03:25:00 PM »
Abolt:

Firstly the reaction temperature will still hang around 50-60°C, even if no column is used and oil bath temp. is above 100°C - it simply can't get significantly higher as long as there are formic acid esters and alcohol present (with bp's being lower than 100°C), and only if these two are distilled away completely, temp. can rise to more than the bp of the higher boling compound (i.e. ethanol). The only reason why a vigreux could raise the bp of a reaction is its operating pressure (the pressure that builds up inside it), and this is not woth mentioning. Perhaps you have to apply more heat because of energy losses in the column (no isolation?), but this results only in quicker evaporation, NOT in higher bp!!!

And as there is in fact ethylformate formed, the removal of it drives the reaction forward (ever heard of the LeChatelier principle? like A+B<->C+D and if D is contiuously removed, more C is formed as the equation shifts to the right) - using a vigreux just helps separating the fractions and allows for a proper separation as the bp's of ethylformate and ethanol are closer together than 30°C...

Secondly, I wouldn't try extracting methylamine*HCl from ammonium chloride with (hot) methanol - NH4Cl is pretty soluble in it, so separating the two with MeOH is not advised.

Just some of the reasons why the patented procedure posted by Orgy will work, whereas your proposed procedure will probably fail (or produce mainly NH4Cl)...

(I tried it BTW, quick heating/distillation simply results in incomplete reaction - only advised if you need loads of ammonium chloride  :P )

So please don't flame Organikum because you tweaked too much!

Greetz A


Bond_DoubleBond

  • Guest
possible mechanism
« Reply #51 on: June 13, 2004, 03:03:00 AM »
swim firmly believes that the reaction involving ethyl formate is independent of the methylamine creation.

CH2O + C2H5OH -> C2H5OCHO + 2 extra hydrogens.

swims' observations:

1. if the reaction is stopped after all the ethyl formate is collected, nearly all of the ammonium chloride can be recovered. 

2. if the reaction is allowed to proceed at higher temperatures, near qualitative conversion to methylamine is had.

perhaps the imine fomation proceeds just as according to

https://www.thevespiary.org/rhodium/Rhodium/chemistry/methylamine.html

.

NH4Cl + CH2O -> [H2C=NH].HCl + H2O

judging from reports of alcohol-less methylamine synth writeups and from swim's own experience completing this reaction after the formate has been collected, it seems that the imine formation occurs at around 80c.  At this point, half of the formaldehyde has already been consumed into formate, and the other half now to the imine.  and there are the unaccounted for hydrogens to do the reducing somehow. 

swim is still a novice at org chem as far as book-learnin goes, but this mechanism seems to correlate all of swim's observations.

thoughts?

Antoncho

  • Guest
The mechanism
« Reply #52 on: June 13, 2004, 08:58:00 AM »
NH4Cl + 2HCHO __> CH3NH3Cl + HCOOH

Thus formed HCOOH reacts with ethanol:

HCOOH + C2H5OH __> HCOOC2H5 + H2O

forming ethyl formate, which is removed by dictillation.

Thus, it is precisely that Le Chatelier thingy which drives the rxn forward, IMHO.

Bond_DoubleBond

  • Guest
that is certainly not it.
« Reply #53 on: June 14, 2004, 12:03:00 AM »
that is certainly not it.  you can reflux and distill away all the ethyl formate and stop the reaction and you will get nearly all your ammonium chloride back.  however the amcl reacts in this whole process, it doens't do it (at any appreciable rate, at least) until the temperature far surpasses that of the boiling point of the mixture (ethyl formate vapor).

armageddon

  • Guest
Well if the water isn't removed too, there is...
« Reply #54 on: June 14, 2004, 01:15:00 PM »
Well if the water isn't removed, the following equation shifts to the left:

HCOOH + C2H5OH <> HCOOC2H5 + H2O

(ethyl formate is somewhat soluble in hot H2O, dissociating into formic and ethanol, shifting everything to the left - and more formic is available)

..more unreacted formic acid in the reaction inhibits the formation of methylamine (just LeChatelier backwards)..

NH4Cl + 2HCHO <> CH3NH3Cl + HCOOH

(remember that methylamine is ONLY made if the formed formic acid is REMOVED from the reaction, too much water/too little alcohol inhibits this)

That might be the reason why heating to just 80°C (and evaporating first ethylformate, then slowly the ethanol) results only in unreacted ammonium chloride/formaldehyde, whereas driving off the water gives appreciable yields...

Or perhaps you simply distilled away the alcohol too fast, together with the formate?

Greetz A


n00dle

  • Guest
Maybe offtopic but could the top of the reflux
« Reply #55 on: June 14, 2004, 04:31:00 PM »
Maybe offtopic but could the top of the reflux column or end of condensor be put under a small amount of hcl to salt out any dimeam that is causing stinky fish smell?

(One also thinks the slight pressure of the water might raise the bp's for the rxn which might be in our favour?)

Organikum

  • Guest
Thats not off-topic
« Reply #56 on: June 14, 2004, 10:07:00 PM »
but complete bullshit.
Dont post if you dont have ANY clue whats a thread or certain reaction is about.

Regards
ORG


abolt

  • Guest
Well, well, well..............it seems that I...
« Reply #57 on: June 15, 2004, 06:04:00 AM »
Well, well, well..............it seems that I have stirred this thread back into life.

abacus:Abolt, I  must have missed the correction by KCN, sorry about that I thought i had the whole thread and had no knowledge of a correction.

No need for an apology. ;)  Its just that I didn't want other bees to be discouraged by that thread because you left something out.

Good methylamine.hcl is not that hard at all, in fact, really simple using hexamine (solid camping fuel tablets)and HCL.

I am aware of that, Swim has seen MeNH3Cl in good yields by substituting with Hexamine and Hcl and following the Vogel's procedure.

I also go so far to say from experience that the reaction occurs below 103-104DegC.  The reaction (without ethanol) starts at about 80DegC and further heating in a hot water bath so that the flask temperature hovers around 95-100DegC works like a charm (which is not the method org suggest using ethanol).

That may be correct, I only quoted what the most common literature stated.

orgy: What you think is actually not important,

Well it seems to be important enough to get an over the top, egotistical reply from you.

It was new enough that the IG-Farben got this patent granted, so I guess it is not a "fandangled arse about version" but something different.

Then, unless you are saying that BDB and Swim are both liars, how is it different?

BDB and Swim have stated that when All the Formate and Ethanol has been distilled the reaction is incomplete, so aside from removing formaldehyde at a lower reaction temp, what part does it play??????

important is that it works fine and produces better yields in much shorter time than the method proposed before (the one outlined in Vogels 3rd).

...........and where did I say that it didn't????????

There is no difference if formaldehyde and ammoniumchloride or hexamine and HCl are used. Read the thread and you MIGHT be able to realize this.

I have stated the same thing. Read the thread and YOU MIGHT be able to realize this.

abolt, find something better and post it, or fuck the shut up, ok?

GO AND GET YOUR GUTS FUCKED!!!!!!

I have the impression that quite a lot of bees like this "fandangled arse about version" very well and I cant understand what you complain about if not your own incapabilities.

I am not complaining, I am merely trying to give my understanding of the reaction. My opinions are based on the actual research of Swim and another bee.

Orgy, I find it quite hypocritical that you would take an egoistic approach to my statements after all the crap you have stated about moderators having "ego problems".

FWIW, I don't care if I am right or wrong.........for if I am proven correct, then I know something...........and if I am proven incorrect.......then I learn something.

EITHER WAY I WIN!

By not allowing my ego to enter into things I hope to attain wisdom.

I SUGGEST YOU DO THE SAME!!!!!!!!

Armageddon: Secondly, I wouldn't try extracting methylamine*HCl from ammonium chloride with (hot) methanol - NH4Cl is pretty soluble in it, so separating the two with MeOH is not advised.

That's strange, the information I have states that NH4Cl is only slightly soluble in Methanol, and from what I have learned at the Hive, small amounts of NH4Cl are tolerable in aminations due to the selectivity of Methylamine in the reaction.

Just some of the reasons why the patented procedure posted by Orgy will work

.........for the second time, where have I stated that it will not.

whereas your proposed procedure will probably fail (or produce mainly NH4Cl)...

How did you arrive at that conclusion, it is virtually the same procedure?

(I tried it BTW, quick heating/distillation simply results in incomplete reaction - only advised if you need loads of ammonium chloride )

Which further validates the point that Swim and BDB have been making that the reaction is not finished after the distillation of formate/ethanol and that a further higher reaction temperature is required.

So please don't flame Organikum because you tweaked too much!

............for the second time, I did not flame Orgy!!!!!

..........at least up until this post.

(remember that methylamine is ONLY made if the formed formic acid is REMOVED from the reaction, too much water/too little alcohol inhibits this)

......are you saying that the addition of alcohol is essential to the formation of Methylamine via hexamine and HCl??


Otherwise thanks for taking the time to write your explanation as to how the reaction proceeds. :)

BDB & Antocho: Thank you for your contributions. I will study what you have stated closely.


Bond_DoubleBond

  • Guest
meoh -> good separation
« Reply #58 on: June 15, 2004, 12:18:00 PM »
according to chromic's work,

Post 247196 (missing)

(Chromic: "Recrystallizing Methylamine Hydrochloride", Newbee Forum)


a boiling meoh recrystallization will result in a product that is 94% pure.  close enough for swim.

and a big thanks to chromic for that data.  handy info.

abacus

  • Guest
Alcohol is not vital
« Reply #59 on: June 15, 2004, 12:48:00 PM »
Nobody is seriouly saying alcohol is needed for the reaction to occur at all are they???, surely not???, Thats stupid to suggest that.

SWIM's reactions using hexamine and HCL NEVER involved adding alcohol and still ended up with good methylamine.hcl proving to that bee that alcohol was not important or required at all.  Likewise i think abolt has a few posts somewhere that never used alcohol.

I Think the point on the thread was to use it to increase yields.

Maybe a few people should go back and study Rhodiums excellent summary of this reaction on his page, and then use the addition of ethanol in some experiments.

The standard reaction using hex/HCL or formaldehyde/NH4CL itself is not the problem, the problem is the recovery, following Vogels procedure of distilling half the water away, crashing out the NH4CL, distilling again to crystalise the methylamine.HCL is were I believe most bees have trouble.

Heres my 2 cents worth with some details.

After distilling down to half original volume, let cool and filter out the NH4CL.

Setup for redistillation and distil again at atmospheric pressure UNTIL the flask contents temperature is OVER 150DegC, Then pour into a container and cool.  This will cause the whole solution to form a solid.  This seems like a lot of crystallising methylamine.hcl but its not.

When solid, crush up and vacuum filter with a buchner, rinse crystals in cold ethanol once, rinse once in acetone, and dry on newspaper for about 10-20 minutes, then store in a sealable container.  The recovered methylamine.hcl is fine for animations and recystallising is not required NOR is washing with chlorofrom (in fact chloroform washes do nothing from Swims experience and a quick acetone wash just gets rid of the residual ethanol and helps fast drying of the methylamine.hcl, when the reaction is carried out using a hot water bath for good temp control)

Washing with cold ethanol takes some product with it but it also takes most of the impurities leaving very good colourless methylamine.hcl

Then redistill the filtrate once more until liquid temp is 150-160DegC, again cool, let solidify, crush and filter, rinse with small amount cold ethanol, acetone if you want and dry and store.  Throw the filtrate away unless really keen to try to get a third crop (normally wont get any)

The point is, you have to let the mother liquid heat up to over 150DegC if you want a decent amount of it crystalising from the solution.

Yields using hexamine and HCL (without adding alcohol that this thread is dealing with) are usually 400g methylamine.hcl from 600g Hexamine.

Btw, how do I delete my posts on using nitro, this bee with never waste so much time with nitro ever again, when its so much better using methylamine.hcl, hehe

live and learn I suppose
Abacus