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Author: Subject: methylamine via direct amination of methyl bromide
chemist1243
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methylamine via direct amination of methyl bromide

BTW: im aware of the assosiation of methylamine with some very popular illegal stimulants. im choosing methylamine not because i can make drugs, but because its a very simple amine and finding different ways to make it should in theory not be that hard. in no way am i trying to reinvent the wheel with new methylamine synthesis's, but IMO is ts pretty fun just making chemicals via obscure and unheard of methods.

anyways,
Once upon a time(yesterday), I was really bored.

I decided I was going to try to make methylamine using an improvised method, Here's the scheme:

In an ice bath, methyl bromide would be produced in situ via addition of sulfuric acid to a solution of water, methanol, and NaBr. the mixture is kept below 3 C to prevent methyl bromide from reaching its boiling point and escaping from the reaction mixture.

The resulting NaHSO4 would be filtered off, and the resulting filtrate solution would be gassed with ammonia. The bromine on the methyl bromide would grab a hydrogen from the bromine in the solution, producing a mixture of HBr, trimethylamine, methylamine, and dimethylamine. The ammonia would also convert excess sulfuric acid into ammonium sulfate, and any excess HBr into ammonium bromide.

This would be allowed to stand for a while, and then would be acidified to convert all of the alkyl amines in solution to their HCl salt, and any excess ammonia still in the solution would be turned into ammonium chloride.

I didn't expect high(if any) yields of methylamine at all, and im pretty sure I didn't get any anyways.

The entire procedure i did is stated below:

A solution of 15ml of water, 20g of NaBr, and 7ml of pure MeOH was made. This was placed in an ice bath and cooled to 0 C, after which 15ml of conc sulfuric acid has added dropwise with strong stirring, which took around 1.5 hours. the temp was kept under 5 C the entire time.

After this i filtered off all of the NaHSO4 and started to bubble NH3 gas into the mixture at a rate of around 5 bubbles per second. This continued for 1 hour and 3 minutes, after which the reaction was allowed to sit at room temperature in a stoppered off flask overnight.

When morning came, a 31.45% HCl was added to the mixture, which immediately caused a precipitate to form, and HCl was added further until no more precipitate would fall out of solution. Methylamine HCl is pretty soluble in water, so I assumed that the precipitate was not methylamine HCl. said precipitate was filtered off and collected just incase.

Since methylamine is pretty much insoluble in acetone, i just added acetone to the mixture. A bright white crystalline precipitate immediately formed. Acetone was added further until no more precipitate would fall out of solution. The precipitate was filtered and collected.

What do you personally think is in the two precipitates which were collected? Is it worth trying to try and recrystallize methylamine out of one of the precipitates, if there is any at all?
Im strongly leaning toward the possibility that there is in fact no methylamine in either one of the collected precipitates, but I always like a second opinion.

Also, I hope everyone had a very happy holiday this year.
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You probably made ammonium chloride and ammonium bromide.
NaBr + H2SO4 = HBr + NaHSO4

Then an excess of NH3 followed by HCl will give:

HBr + NH3 = NH4Br
HCl + NH3 = NH4Cl
draculic acid69
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Methyl bromide is a gas so making it condensing it then refluxing with it are going to be difficult.why not use methyl iodide?
chemist1243
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 Quote: Originally posted by draculic acid69 Methyl bromide is a gas so making it condensing it then refluxing with it are going to be difficult.why not use methyl iodide?

well, i figured that if the reaction temperature was kept below that of methyl-bromide, it would thermally incapable of turning into a gas and thus escaping.

i thought of using methyl iodide at first, but decided against it because:

1. someone has done it from that method before.
2. NaBr, MeOH, and H2SO4 can be obtained by the gallon and are cheap as dirt.
3. iodide salts are expensive($12 per oz) 4. waste cleanup wont be too difficult chemist1243 Hazard to Others Posts: 117 Registered: 7-8-2019 Member Is Offline  Quote: Originally posted by madcedar You probably made ammonium chloride and ammonium bromide. NaBr + H2SO4 = HBr + NaHSO4 Then an excess of NH3 followed by HCl will give: HBr + NH3 = NH4Br HCl + NH3 = NH4Cl you're forgetting the MeOH. NaBr + H2SO4 + CH3OH = H2O + NaHSO4 + BrCH3 and then: H2O + NH3 + BrCH3 = NH2CH3 + NH4Br + H2O and then: NH2CH3 + HCl = NH2CH3HCl 1 molar excess NH3 isnt a problem because it will just neutralize excess H2SO4. any remaining NH3 in solution will be further neutralized by the HCl. also when the NH3 is added it will react first with the weak Br/C bond splitting off a HBr molecule, which is gonna make ammonium bromide when NH4OH is made simotaniously via reaction of NH3 with H2O which was created as a by product from the hydroxyl group being kicked of the MeOH and combing with a proton(from the H+ ions caused by creation of HBr), with more NH4OH from addition NH3 being bubbled in at the same time. in the end it wont matter anyways, because all alkaline products will just be made into salts later. i know this is kind of hard to follow but i swear to god all of the molar ratios are correct. as long as enough NH3 is made the reaction (should) go smoothly. excess shouldnt be a problem so long as the solution is properly neutralized in the end. also, as a side note, my yeild from the acetone addition precipitated once dried is around 4ml. i hate to measure solids that way but i don't quite have a scale yet. [Edited on 29-12-2019 by chemist1243] Tellurium Hazard to Self Posts: 72 Registered: 12-7-2017 Location: Group 16, Chalcogen City Member Is Offline Mood: smelly Well as draculic acid stated I would use methyl iodide, as it's way more easier to handle than a neurotoxic, carcinogenic gas. I know, that as you stated iodide is way more expensive than bromide, but you can recycle the iodide quite easily. Anyway this reaction route isn't that promising if you just do it for the MeNH2, because the alkylamines should be even better as a nucleophile than ammonia, so you will only get a very small yield on your methylamine and more secondary, tertiary and maybe even quaternary amines. I would try to react formaldehyde with ammonium chloride to make methylamine, thats a way more promising route. Also you could make your formaldehyde from your methanol, so you would in fact make methylamine from your MeOH anyway. chemist1243 Hazard to Others Posts: 117 Registered: 7-8-2019 Member Is Offline  Quote: Originally posted by Tellurium Well as draculic acid stated I would use methyl iodide, as it's way more easier to handle than a neurotoxic, carcinogenic gas. I know, that as you stated iodide is way more expensive than bromide, but you can recycle the iodide quite easily. Anyway this reaction route isn't that promising if you just do it for the MeNH2, because the alkylamines should be even better as a nucleophile than ammonia, so you will only get a very small yield on your methylamine and more secondary, tertiary and maybe even quaternary amines. I would try to react formaldehyde with ammonium chloride to make methylamine, thats a way more promising route. Also you could make your formaldehyde from your methanol, so you would in fact make methylamine from your MeOH anyway. thanks so much, for this, it clears a bit up. i dont think ill try the MeI method, but ill take a look at formaldehyde/ammonium chloride method. im also gonna take a look at a very obscure method which i found in a copy of this old ass chemistry book. it involves reacting NaOH, acetamide, and calcium hypochlorite bleaching powder to make methylamine in 70% yields. im really skeptical so ill have to do a shit load of mor ereaserch but hopefully it works. chemist1243 Hazard to Others Posts: 117 Registered: 7-8-2019 Member Is Offline  Quote: Originally posted by Tellurium Well as draculic acid stated I would use methyl iodide, as it's way more easier to handle than a neurotoxic, carcinogenic gas. I know, that as you stated iodide is way more expensive than bromide, but you can recycle the iodide quite easily. Anyway this reaction route isn't that promising if you just do it for the MeNH2, because the alkylamines should be even better as a nucleophile than ammonia, so you will only get a very small yield on your methylamine and more secondary, tertiary and maybe even quaternary amines. I would try to react formaldehyde with ammonium chloride to make methylamine, thats a way more promising route. Also you could make your formaldehyde from your methanol, so you would in fact make methylamine from your MeOH anyway. thanks so much, for this, it clears a bit up. i dont think ill try the MeI method, but ill take a look at formaldehyde/ammonium chloride method. im also gonna take a look at a very obscure method which i found in a copy of this old ass chemistry book. it involves reacting NaOH, acetamide, and calcium hypochlorite bleaching powder to make methylamine in 70% yields. im really skeptical so ill have to do a shit load of mor ereaserch but hopefully it works. Tellurium Hazard to Self Posts: 72 Registered: 12-7-2017 Location: Group 16, Chalcogen City Member Is Offline Mood: smelly You're welcome! The reaction with acetamide works, you can also just use sodium hypochlorite bleach for this. The reaction thats happening is called Hofmann rearrangement. It's typicaly done with NaOH and Br2, which forms hypobromite, but you can also use hypochlorite instead without any problems stoichiometric_steve International Hazard Posts: 783 Registered: 14-12-2005 Member Is Offline Mood: satyric  Quote: Originally posted by chemist1243 I didn't expect high(if any) yields of methylamine at all, and im pretty sure I didn't get any anyways. You could have spent your time reading about why this will not work and furthered your general knowledge of chemistry rather than stupidly wasting resources. But looking at your post history, it becomes pretty obvious what your motivations are. Certainly not "learning". chemist1243 Hazard to Others Posts: 117 Registered: 7-8-2019 Member Is Offline Quote: Originally posted by stoichiometric_steve  Quote: Originally posted by chemist1243 I didn't expect high(if any) yields of methylamine at all, and im pretty sure I didn't get any anyways. You could have spent your time reading about why this will not work and furthered your general knowledge of chemistry rather than stupidly wasting resources. But looking at your post history, it becomes pretty obvious what your motivations are. Certainly not "learning". oh yes, what a waste! if only i still had my$5 worth of chemicals that i used!

you have 0 clue what my intentions are. your stigma against certain chemicals and synthesis only furthers the fear and misinformation surrounding ameture chemistry.

can you really blame me for being interested in drug chem? whats not to gaze in awe at, seeing the mental state and thought process of someone change in mere seconds, all due to a few milligrams of a substance?

i am interested in the properties of tryptamines and empathenogenic stimulants as well as their effect on the human brain, and i strictly refuse to change my directive towards anything else.

within the bounds of the law, i will reasearch the world of psycoactive substances to the fullest extent of the matter, and i will never stop so long as i live.

i understand your concern that i may be making and distributing illegal drugs, but i am in fact rather making new drugs and testing them on rats and other neurologically simmilar animals which may be kept in a well fitted enviorment, and legally may be tested on within reasonable and humane limits.

i will eventually go to school to get a degree, perhaps something like a biochemist for pharmicutical companies.

please understand that my intentions are pure, and that i mean no harm to society in anyway.

please also understand that experimenting with new methods of creating old chemicals is fun and interesting for me. methylamine is a very simple amine, and thus finding new ways to make it should be challenging, but not impossible.

please respect mine and others interests. not everything on the surface may be as simple and easy to understand as one may initally think, so if you are so concerned as to what one may need procedure or chemical or peice of knowlage for, consider asking them what they need it for instead of jumping to conclusions.

my post history peiced together leads to some dark conclusions, but as you can see, upon further explanation, things sometimes come to light in a much more positive way,

[Edited on 31-12-2019 by chemist1243]
S.C. Wack
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 Quote: Originally posted by chemist1243 my post history peiced together leads to some dark conclusions

Either you are:

the latest in a long line of accounts that seem to be made by the same bored person for the purpose of getting a REACT TO ME response such as this

going to start a large fire and/or kill someone.

"You're going to be all right, kid...Everything's under control." Yossarian, to Snowden
chemist1243
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Quote: Originally posted by S.C. Wack
 Quote: Originally posted by chemist1243 my post history peiced together leads to some dark conclusions

Either you are:

the latest in a long line of accounts that seem to be made by the same bored person for the purpose of getting a REACT TO ME response such as this

going to start a large fire and/or kill someone.

again, please respects mine and others interests. my lengthy explanation should not be seen as a monument for attempted visual attention or attraction, but rather as a tool to better understand why i like doing why i do.

you need not reject it in such a manner that is obviously meant to belittle or insult its author. i would only ever treat you or others in ways that you would treat me, which i often even stray away from and just try to respect others despite how they present things to me.

[Edited on 3-1-2020 by chemist1243]
chemist1243
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Quote: Originally posted by stoichiometric_steve
 Quote: Originally posted by chemist1243 I didn't expect high(if any) yields of methylamine at all, and im pretty sure I didn't get any anyways.

You could have spent your time reading about why this will not work and furthered your general knowledge of chemistry rather than stupidly wasting resources.

But looking at your post history, it becomes pretty obvious what your motivations are. Certainly not "learning".

i know exactly how the reaction should go out in theory, and ive found a few explanations to support your theory that it wont work. i figured its important to deal with the synthesis problems from all angles and veiw points. should research why this wont work. i think i should at the very least try what you suggested, although you did say it in a rather rude and off putting manner.
maybe its just me though, so ill try my best to take a second look at why this 'wont' work.

here's what i got:

bromine is a pretty good leaving group. the Br should seize its bond with the carbon, taking both electrons with it, making a carbocation and a Br-. the ammonia should then act as the nucleophile, stabilizing the carbocation by using its lone pair to form a bond, giving us CH3NH3 and Br-. the resulting positively charged nitrogen atom will then grab an electron from another ammonia molecule, expelling the Br- in the process, giving us CH3NH2 and a proton. the proton formed will combine with the ammonia, forming NH4+, which reacts with Br- to give NH4Br. all in all, we should get a combination of NH4Br and NH2CH3. classic nucleophilic substitution reaction

the only reasons i see may be the problem are:

1: i need to use a polar-Aprotic solvent to prevent hydrogen bonding with nucleophiles.

2: the physical properties of the reactants make it impossible for any reaction to take place before they escape and/or degrade.

3: the amount of energy output from this reaction is greater than the amount of energy that was initially put into the reaction, which wouldn't be possible, thus it needs more energy.

i don't think number 2 is the reason, as the reaction temp during the bromination of MeOH was lower than that of methyl bromide's boiling point.

Number 1 could be plausible, especially considering how readily ammonia reacts with water. i may have under estimated the side reactions from NH4OH despite simply using more ammonia.

Number 3, i think is the most plausible, as the entire reaction was done outside at 15C, max.

im think it's worthy to have another go at it, even if it means low yield, which i dont really care about because the prospect of making something from basic materials and knowladge is more fun than pumping out gram after gram of methylamine which i wont be able to use up do to lack of legal uses.

im thinking this:

a dilute(yet still molar equivalent) H2SO4 solution is made by adding 15ml of drain cleaner acid to 100ml of acetone in an ice bath. bromide salt is added, temp is kept at appropriate levels, blah blah blah. then 10ml of pure MeOH is brominated.

the resulting non aqueus Methyl bromide solution is cooled in an ice bath. a 1.5 molar excess of anhydrous liquid ammonia is added dropwise with strong stirring, with NBC filter gas mask on in fume hood or somewhere else with good ventilation that is far away from all things dear to me as well as any by standers.

the resulting solution is stirred for an additional 1 hour in a
dry ice/acetone or liquid nitrogen bath, refluxed at 30 C for 1 hour, then refluxed at 40 C for 1 hour, and then finally fractionally distilled to yield 4ml or so(if that) of freebase methylamine.

scale up to get appreicable amounts if you wanna milk it, but personally i think, especially when considering the low yield and liquid ammonia hazards, it really is too much of a hassle.

[Edited on 3-1-2020 by chemist1243]
S.C. Wack
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 Quote: Originally posted by chemist1243 my lengthy explanation should not be seen as a monument for attempted visual attention or attraction, but rather as a tool to better understand why i like doing why i do.

That had nothing to do with it.

 Quote: Originally posted by chemist1243 you need not reject it in such a manner that is obviously meant to belittle or insult its author.

Everything I said is true. Either you are fake as there are a lot of suspiciously similar accounts, or you are a danger to yourself and others. I was quite dangerous myself and maybe my confidence makes me more dangerous now. If you are real you are unaware of how to make bromomethane (note that no one said how to do it right), and the existence of methylsulfuric acid and ammonium methylsulfate.

"You're going to be all right, kid...Everything's under control." Yossarian, to Snowden
chemist1243
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Quote: Originally posted by S.C. Wack
 Quote: Originally posted by chemist1243 my lengthy explanation should not be seen as a monument for attempted visual attention or attraction, but rather as a tool to better understand why i like doing why i do.

That had nothing to do with it.

 Quote: Originally posted by chemist1243 you need not reject it in such a manner that is obviously meant to belittle or insult its author.

Everything I said is true. Either you are fake as there are a lot of suspiciously similar accounts, or you are a danger to yourself and others. I was quite dangerous myself and maybe my confidence makes me more dangerous now. If you are real you are unaware of how to make bromomethane (note that no one said how to do it right), and the existence of methylsulfuric acid and ammonium methylsulfate.

i'm sorry you feel that way.
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It is probably spitting against the wind... but there are some flaws in your procedure.

First, methyl bromide is not soluble in water, at least not in the concentrations you are using and definitely not in a saturated salt solution, that is why I'm pretty sure you already failed at this step. Otherwise you would have seen a second layer. Also this reaction is not very fast and heating is necessary to get it done in considerable time. The carbocation you are talking about is the probalby one of the least energy favorable to form... good luck forming from methanol at under the boiling point of methyl bromide.

After the first step failing, of course nothing could come out anymore but where it would also have gone wrong:

You are slowly increasing the ammonia concentration. That is recipe for triethyl amine... you want to slowly add the methyl bromide, not the other way around.

No, the HCl salts of these amines are not very soluble in acetone. But that is in dry acetone. You are talking about soaking wet acetone here. What you have crashed out was salt, a lot of salts, but not that of an amine besides ammonium.

 Quote: 1: i need to use a polar-Aprotic solvent to prevent hydrogen bonding with nucleophiles.

This doesn't make sense, hydrogen-bonding is the least of your concerns here. Water is fine as a solvent, but yes, it does compete a bit.
 Quote: 2: the physical properties of the reactants make it impossible for any reaction to take place before they escape and/or degrade.

No, you are right, but not because of the reasons you list.
 Quote: 3: the amount of energy output from this reaction is greater than the amount of energy that was initially put into the reaction, which wouldn't be possible, thus it needs more energy.

Good God, where did you pick up this nonsense? Your conclusion is probably OK, but the reasoning behind it doesn't make sense.
chemist1243
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Quote: Originally posted by Tsjerk
It is probably spitting against the wind... but there are some flaws in your procedure.

First, methyl bromide is not soluble in water, at least not in the concentrations you are using and definitely not in a saturated salt solution, that is why I'm pretty sure you already failed at this step. Otherwise you would have seen a second layer. Also this reaction is not very fast and heating is necessary to get it done in considerable time. The carbocation you are talking about is the probalby one of the least energy favorable to form... good luck forming from methanol at under the boiling point of methyl bromide.

After the first step failing, of course nothing could come out anymore but where it would also have gone wrong:

You are slowly increasing the ammonia concentration. That is recipe for triethyl amine... you want to slowly add the methyl bromide, not the other way around.

No, the HCl salts of these amines are not very soluble in acetone. But that is in dry acetone. You are talking about soaking wet acetone here. What you have crashed out was salt, a lot of salts, but not that of an amine besides ammonium.

 Quote: 1: i need to use a polar-Aprotic solvent to prevent hydrogen bonding with nucleophiles.

This doesn't make sense, hydrogen-bonding is the least of your concerns here. Water is fine as a solvent, but yes, it does compete a bit.
 Quote: 2: the physical properties of the reactants make it impossible for any reaction to take place before they escape and/or degrade.

No, you are right, but not because of the reasons you list.
 Quote: 3: the amount of energy output from this reaction is greater than the amount of energy that was initially put into the reaction, which wouldn't be possible, thus it needs more energy.

Good God, where did you pick up this nonsense? Your conclusion is probably OK, but the reasoning behind it doesn't make sense.

Okay. This obviously doesn't work. I'm wrong and I somewhat knew it from the beginning, but none the less my logic is terribly flawed. Would you consider linking me some sources to improve on my understanding of the topics I failed to properly account for?
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You would end up with trimethylamine and possibly some tetramethylammonium bromide.
You need to use another method, the gabriel or delepine.
I suggest sodium diformylamide, I worked with that a few times and it is the best gabriel reagent imaginable, also easy and cheap to make(sodium methoxide and formamide).
Tsjerk
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 Quote: Originally posted by chemist1243 Okay. This obviously doesn't work. I'm wrong and I somewhat knew it from the beginning, but none the less my logic is terribly flawed. Would you consider linking me some sources to improve on my understanding of the topics I failed to properly account for?

Wikipedia is usually a nice start, you can find most solubilities, melting points, boiling points etc.

https://www.prepchem.com/ is a nice second, it doesn't have methyl bromide on it, but you can deduct some basic reaction mechanisms from analogous, like isopropyl bromide and pentane bromide.

Also Wikipedia is nice to look for information about the reaction mechanisms involved. It will tell you there is a range in stability of carbocations and the methyl cation is the least favorable. This doesn't have to be a problem though as methyl bromide boils at a so low boiling point, it is separable from methanol.

Edit: your methyl bromide idea should work, if you do it while collecting the product via distillation. Methyl amine via amination with ammonia... probably less so.

[Edited on 11-1-2020 by Tsjerk]
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The last thing needed here is a recipe for how to use the available chemicals to make "a very toxic fumigant gas with poor olfactory warning properties". The chem set I got as a kid didn't include KCN, can't imagine why.

 Quote: Originally posted by chemist1243 IMO is ts pretty fun just making chemicals via obscure and unheard of methods.

Randomly tossing about chemicals will result in nothing but waste and unforseen problems. Research requires something resembling knowledge. There is a reason why the methods are unheard of.

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I actually kinda wonder if you would get any MeNH3Br crystals/smoke by combining MeBr and NH3 gases. Assuming the crystals don't react with the gas, it's a pretty clever (if low-yielding) way to achieve monomethylation.

[Edited on 04-20-1969 by clearly_not_atara]
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I could imagine someone getting hurt by randomly throwing chemicals together, lets say a metal or a strong base with DCM
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 Quote: Originally posted by clearly_not_atara I actually kinda wonder if you would get any MeNH3Br crystals/smoke by combining MeBr and NH3 gases.

If it was so easy I doubt organic chemistry would be waiting around 150 years for y'all to figger it out. If the combination was so easy wouldn't further combination be just as easy?

There are sure uses for the a bit too conveniently made bromomethane to make meth, such as a less common route to P2P, and methylamine, (without producing other amines); for the low functioning chemist, the actual result may fall in the vicinity of failure, fire, methylated DNA, death, and so on.

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 Quote: If it was so easy I doubt organic chemistry would be waiting around 150 years for y'all to figger it out. If the combination was so easy wouldn't further combination be just as easy?

Oh, I strongly doubt you'd get a useful yield. It's a gas-phase reaction and strongly exothermic if it proceeds. It would not be a practical way of producing methylammonium bromide any more than the NH3+HCl gas reaction is a good way to make ammonium chloride.

The thought was that kinetically the gases react with each other faster than the solid crystals react with the ammonia. Since a proton transfer from methylammonium to ammonia is necessary for double alkylation, this might suppress that pathway.

(Besides, everyone knows that the hexamine method is the real way to make methylamine!)

[Edited on 13-1-2020 by clearly_not_atara]

[Edited on 04-20-1969 by clearly_not_atara]
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