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timsong
(Hive Bee)
12-20-01 23:51
No 249367
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Easy Ethylamine ?
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After dreaming about the possibility of using ethylamine as a more temperature friendly ammonia replacement in a birchy type reaction. I thought I would post a possible otc route for this compound to get some bees buzzing.<br><br>Ethylamine can be obtained by the action of ammonia on an alkyl halide<br><br>C2H5Cl + NH3 > C2H5NH3Cl<br>C2H5NH3Cl + NH3 <> C2H5NH2 + NH4Cl<br><br>This reaction is general but has the disadvantage that higher substitution also occurs, giving also seconadary and tertiary amines.<br>But this is no problem with (X)Ethylamines as they can be easily seperated by distillation<br><br>Boiling Points<br><br>Ethylamine : 16.6c<br>Diethylamine : 56c<br>Triethylamine : 89.5c<br><br>With no reference to a laboratory precedure at hand, I can only assume that the setup would just require a calculated amount of dry ammonia gas to be passed through a cooled amount of ethylchloride, I may assume wrong though, this is where I could do with some other bee's input.<br><br>Is this only a dream ?<br><br>
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goiterjoe<br>
<i>(<span title="The user's title at the time of posting">Hive Addict</span>)</i><br>
<span title="Posting date">12-20-01 23:56</span><br>
<span title="Link to this post by using the markup [249371]">No 249371</span><br>
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<title>Re: Easy Ethylamine ?
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I wonder if refluxing ethyl chloride in ammonium chloride will produce ethylamine and chlorine gas. Supposedly this works when using iodine as the halogen, but I'm not sure about how it works for bromine and chlorine.<br><hr>Sed quis custodiet ipsos custodes?
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bujinkan<br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">12-21-01 00:06</span><br>
<span title="Link to this post by using the markup [249375]">No 249375</span><br>
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<title>Re: Easy Ethylamine ?
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<span title="Jump to this post"><a href="../DUMMY">Post 246545</a> <i>(Rhodium: "Re: diethylamine", Chemicals & Equipment)</i></span> rhodium mentions something like this
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timsong<br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">12-21-01 00:13</span><br>
<span title="Link to this post by using the markup [249377]">No 249377</span><br>
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<b title="The subject of this post">Re: Easy Ethylamine ?</b>
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Umm, Rhodium mentions the procedure with iodine/bromine as the halide. It's what would happen if chlorine was the halide, I'm worried that the reactin may be too vigourous*, but conversion of the chloride to bromide/iodide can't be too much of a headache.<br><br>NaBr + C2H5Cl > NaCl + C2H5Br ??????????<br><br>*Actually, what am I talking about, the chloride may be less reactive than the bromine, looking at other alkyl halide reactions
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<font color="#FF0033">Rhodium</font><br>
<i>(<span title="The user's title at the time of posting">Chief Bee</span>)</i><br>
<span title="Posting date">12-21-01 02:05</span><br>
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<b title="The subject of this post">Re: Easy Ethylamine ?</b>
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You want to use ammonia in an alcohol, not ammonium chloride. This is the very same reaction as the one with bromosafrole -> MDA, just follow those descriptions, and use more ethyl chloride.
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Bwiti<br>
<i>(<span title="The user's title at the time of posting">PVC-Analog Taste-Tester</span>)</i><br>
<span title="Posting date">12-21-01 07:48</span><br>
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<b title="The subject of this post">Re: Easy Ethylamine ?</b>
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If nitroethane's reacted with Al/Hg to produce ethylamine, is there a chance that triethylamine will be created? Btw, ethylamine hydrochloride's a bitch to keep dry.<br><hr> Love my country. Fear my government.
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<font color="#ff0000">Osmium</font><br>
<i>(<span title="The user's title at the time of posting">Stoni's sexual toy</span>)</i><br>
<span title="Posting date">12-21-01 11:22</span><br>
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<b title="The subject of this post">Re: Easy Ethylamine ?</b>
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> If nitroethane's reacted with Al/Hg to produce <br>> ethylamine, is there a chance that triethylamine will be<br>> created?<br><br>No.<br><br>If I hear about bees reducing nitroethane to produce ethylamine I will personally cut their genitals off. I cannot condone such blasphemy. Not in my forum.
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Antoncho<br>
<i>(<span title="The user's title at the time of posting">Official Hive Translator</span>)</i><br>
<span title="Posting date">12-21-01 12:46</span><br>
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<b title="The subject of this post">Re: Easy Ethylamine ?</b>
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<blockquote title="Quoted text"><hr><p>If I hear about bees reducing nitroethane to produce ethylamine I will personally cut their genitals off. I cannot condone such blasphemy. Not in my forum. <p><hr></blockquote><p><br><br>Yes, i agree... But is there another practical way?.. Now that i think of it... <br>Obviously, EtCl and NH3 could work, maybee even aqueous - if you use a very large xcess of NH3 probably not much polyalkylthings will bee formed.<br><br>What do you think? Will not ammonia salts also undergo substitution?<br><br>BTW - i believe, EtBr is much easier to make than EtCl (rxn of EtOH w/HCl goes very slowly - SWIM's done it, it's not practical). The proc is on the Rhodium - just H2SO4, NaBr and the alcohol.<br><br>Since we started talking of this - does anyone know if MeBr can bee made the same way?<br><br>Bwiti - i guess, triethylamine (*HBr) can bee made from 3 eq. EtBr and 1 eq. NH3 - maybee add some base to speed up the rxn, i'm not sure. Os, what is your opinion?<br><br>Goiterjoe - can you please give more details on the rxn you mentioned?<br><br>Antoncho
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timsong<br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">12-21-01 15:46</span><br>
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<b title="The subject of this post">Re: Easy Ethylamine ?</b>
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Looking at these amines and ethylchloride, it seems that none of them really readily react with water (amines will dissolve in it).<br><br>As Rhodium said "use ammonia in an alcohol", this seems the answere, and from what it seems the alcohol would not have to be anhydrous. I'm not saying that the reaction could be done with ammonia vodka (maybe it could ?), as thats just too crude, but say recitified spirit could be used, as the alcohol(h20) is mearly being used as a solvent for the ethyl chloride and the ammonia.<br><br>I know a man who will try this in the new year, probably with Ammonia IPA. I wait to hear his results
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timsong<br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">12-21-01 15:57</span><br>
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<b title="The subject of this post">Re: Easy Ethylamine ?</b>
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Oh sorry, my brains not awake yet.<br><br>If their is too much water in the alcohol it will throw the ethylchloride out of solution.
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<font color="#FF0033">Rhodium</font><br>
<i>(<span title="The user's title at the time of posting">Chief Bee</span>)</i><br>
<span title="Posting date">12-21-01 15:59</span><br>
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<b title="The subject of this post">Re: Easy Ethylamine ?</b>
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Antoncho: Yes, you can make MeBr that way, but it is a gas, and thus difficult to handle.
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goiterjoe<br>
<i>(<span title="The user's title at the time of posting">Hive Addict</span>)</i><br>
<span title="Posting date">12-21-01 17:15</span><br>
<span title="Link to this post by using the markup [249578]">No 249578</span><br>
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<b title="The subject of this post">Re: Easy Ethylamine ?</b>
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the reaction I mentioned came from the merck index. I'm not sure of the specifics of it though. It said ethylamine can be produced by reacting ethyl iodide with ammonium iodide. Sounds simple enough, except that it's a lot easier to get ammonium chloride.<br><br>I thought about doing a ethylamine birch once, but temporarily gave up on the idea due to not having an open space to do it in outside, and ethylamine is very flammable and I didn't want to take the risk of dropping an alkali metal into it if there was any water present. Where I am, it's extremely humid all the time, and this could pose a serious problem.<br><hr>Sed quis custodiet ipsos custodes?
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<font color="#ff0000">Osmium</font><br>
<i>(<span title="The user's title at the time of posting">Stoni's sexual toy</span>)</i><br>
<span title="Posting date">12-21-01 17:47</span><br>
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<b title="The subject of this post">Re: Easy Ethylamine ?</b>
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> It said ethylamine can be produced by reacting ethyl <br>> iodide with ammonium iodide. <br><br>Make that NH3 and ethyl iodide and it will work.<br><br>BUT!<br>You guys better break out the pocket calculator and check prices for iodine compounds. To produce 1mole = 155g Et-I you will need 1mole = 126g iodine or a similar iodide source (generously assuming 100% yields). Those 155g Et-I will convert into 45g EtNH2(again assuming 100% yield).<br><br>Same applies to bromine, which is not as costly as iodine but still not cheap either. The bromine compounds will even be more volatile and a bit less reactive.<br><br>Even if you figure out a way to recycle all the chems this will be a very costly and tedios synth. It might be worth it for EtNH2 as a MDE precursor, but as a Birch reaction solvent??? That will be the most expensive meth you ever produced! And don't forget to add your time into the calculation, even if you assume at's all a hobby and you don't earn much as a janitor anyway.<br>Not everything that is theoretically doable and looks good on paper also makes sense in real life!<br><br>
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goiterjoe<br>
<i>(<span title="The user's title at the time of posting">Hive Addict</span>)</i><br>
<span title="Posting date">12-21-01 19:38</span><br>
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<b title="The subject of this post">Re: Easy Ethylamine ?</b>
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that was the whole point of questioning if the reaction would take place if ethyl chloride was substituted instead.<br><br><br><hr>Sed quis custodiet ipsos custodes?
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Aurelius<br>
<i>(<span title="The user's title at the time of posting">Hive Bee</span>)</i><br>
<span title="Posting date">12-21-01 23:11</span><br>
<span title="Link to this post by using the markup [249629]">No 249629</span><br>
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<b title="The subject of this post">Re: Easy Ethylamine ?</b>
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although ethyl chloride would normally be the alkyl of choice for our purposes (Cl sources are easier than I or Br because of price or availability) aurelius does not think this to be the case here. ethyl chloride evaporates to quickly to be of practical use (without allowing for gas phase reactions)
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