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Author: Subject: Ethylamine Synthesis
Waffles SS
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Ethylamine Synthesis

 Quote: Ethylamine is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It is miscible with virtually all solvents and is considered to be a weak base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis. Ethylamine is produced on a large scale by two processes. Most commonly ethanol and ammonia are combined in the presence of an oxide catalyst: CH3CH2OH + NH3 → CH3CH2NH2 + H2O In this reaction, ethylamine is coproduced together with diethylamine and triethylamine. In aggregate, approximately 80M kilograms/year of these three amines are produced industrially. It is also produced by reductive amination of acetaldehyde. CH3CHO + NH3 + H2 → CH3CH2NH2 + H2O Ethylamine can be prepared by several other routes, but these are not economical. Ethylene and ammonia combine to give ethylamine in the presence of an sodium amide or related basic catalysts. H2C=CH2 + NH3 → CH3CH2NH2 Hydrogenation of acetonitrile, acetamide, and nitroethane affords ethylamine. These reactions can be effected stoichiometrically using lithium aluminium hydride. In another route, ethylamine can be synthesized via nucleophilic substitution of a haloethane (such as chloroethane or bromoethane) with ammonia, utilizing a strong base such as potassium hydroxide. This method affords significant amounts of byproducts, including diethylamine and triethylamine. CH3CH2Cl + NH3 + KOH → CH3CH2NH2 + KCl + H2O http://en.wikipedia.org/wiki/Ethylamine

I am looking for easier method but It seems making Ethylamine is more difficult than making Methylamine.Anyone know easier method?

Solubility of ethylamine and its chloride salt in acetone ,Ethanol(and in what solvent is insoluble)?

[Edited on 20-1-2012 by Waffles SS]
Organikum
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The internet has all the physical properties of ethylamine, you know?

Making the acetamide looks not very demanding to me.

Reducing it, ok all are calling for LiAH but thats spoilsport, with LiAH everybody can.

So we know that HI rips virtually all Oxygen out of a molecule (and takes Nitrogen next if conditions are harsh enough). And we have an "O" to much here.

Suggestion: NaI + NaH2PO2 + conc. HCl + H3PO4, heat until something starts to happen in the flask, add amide and reflux for some hours.
Does ethylamine form such a nice azeotrope with ethanol as methylamine does with methanol? Anyways, basify and distill the amine, it is not a gas like meam at RT so thats a cake.
Waffles SS
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Thanks, but i searched it in google and found nothing about solubility of it chloride salt in acetone and alcohol also nothing about decompose temp
Does amalgam method is effective in hydrogenation step?(instead of LiAH)

[Edited on 20-1-2012 by Waffles SS]
Organikum
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 Quote: Originally posted by Waffles SS Thanks, but i searched it in google and found nothing about solubility of it chloride salt in acetone and alcohol also nothing about decompose temp Does amalgam method is effective in hydrogenation step?(instead of LiAH) [Edited on 20-1-2012 by Waffles SS]

In a pipe bomb with serious heat and pressure who knows? But not just so AFAIK. The HI is the only way I know which doesn´t require hydrides, silanes or alltogether. And it is usually high-yielding too, but I know, HI reactions are so yesterday, Unobtainiumhydride thats hip!
entropy51
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Posted somewhere on the forum is an old paper that says heating ethyl iodide, ethanol and ammonia in a sealed tube gives ethylamine with less than 10% of higher substitution products. I can't immediately find the post, but it's here somewhere.

It does require heating in a sealed tube however.

Organikum
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tube

There is always a price to pay....

A tube made from soft steel, welded shut and on one end a sufficient threaded bore for a nice fat screw, maybe a safety bow, done. A thermocouple to show the temp. from some distance and a big old iron bucket over all as the only danger is fluids spraying around if it breaks open. Soft steel will not defragment, in the worst case there might be a leak. Wrap the threads of the screw with teflon tape, you might to want to open it oneday

For large scale one of these ball-like propanetanks - 2 or 3l. Don´t know if you have them, here they are cheap, rated to 10atm and come with a minimum of 10-fold safety marge (kind a law).

Isn´t there some damned catalyst for this amination? I remember something like triethylamine together with something else to catalyse this reaction in a way that for iodine roomtemperature almost suffices.
Just cannot remember ..
entropy51
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 Quote: Originally posted by Organikum There is always a price to pay.... A tube made from soft steel, welded shut and on one end a sufficient threaded bore for a nice fat screw, maybe a safety bow, done. A thermocouple to show the temp. from some distance and a big old iron bucket over all as the only danger is fluids spraying around if it breaks open. Soft steel will not defragment, in the worst case there might be a leak. Wrap the threads of the screw with teflon tape, you might to want to open it oneday For large scale one of these ball-like propanetanks - 2 or 3l. Don´t know if you have them, here they are cheap, rated to 10atm and come with a minimum of 10-fold safety marge (kind a law). Isn´t there some damned catalyst for this amination? I remember something like triethylamine together with something else to catalyse this reaction in a way that for iodine roomtemperature almost suffices. Just cannot remember ..
I used thick Pyrex combustion tubing sealed in the Oxy-propane blast lamp. The sealed tube was enclosed in a pipe bomb much as you describe. It only has to be heated in a boiling water bath for ethylamine.

I've never had one of these thick Pyrex tubes explode, but they scare my shirtless. The best catalyst in my opinion is several hits of Courvoisier to give the chemist sufficient nerve to start heating the sucker.

Several of the old chemistry lab manuals in the forum library have detailed instructions for heating in sealed tubes and I recommend that anyone contemplating an attempt at this method read ALL of them and follow the directions carefully.

I can't recall the details of the catalyst, but I think you are correct. Adding NH4NO3 increases the proportion of primary amine formed, but slows down the reaction and is not necessary for ethylamine.
Ephoton
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calcium propionate can be brought as a bread preservative E282.

ammonium propionate made form this can be rearranged thermally to propionamide very easily.

hoffman of propionamide gives ethylamine.

easy

you should be able to produce a few kilo's in a day this way
and the price per kilo would be around $20 too$50 (probably

no dangerous reductions or flamable solvents needed

just calcium propionate, aqua ammonia, aqua HCl, Bleach and caustic.

Ethyl amine could then be solvent extracted or boiled out of
hoffman turned to Hydrochloride with HCl and then freebased with
caustic to be distilled pure.

of course an excess of caustic when freebasing would be a good idea as it would hold onto most of the water created from the basing of a hydrochloride with caustic.

on second thoughts sulfate would probably be less hygroscopic
and would let you boil the water off it easier than the hydrochloride.

[Edited on 21-1-2012 by Ephoton]

bash-2.05#

Waffles SS
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@Ephoton,Yes Hofmann Rearrangement is really interesting

I think we can customize below route for Ethylamine .
This method for making ethylamine is easier than methylamine because ethylamine boil at ~16c( I have access to calcium propionate )
But i think ammonium propionate can easily be made from ammonium sulfate and calcium propionate.but i dont know what temp needed for making ammonium propionamide from ammonium propionate.

Do you know decompose temp of chloride salt of Ethylamine ?and solubility in acetone and EtOH?

[Edited on 21-1-2012 by Waffles SS]
mario840
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Hahahahaha i knew it, on this forum are only google-amateur-chemists, to my thread no one can answer because they know nothing more than goole , in this thread as always some useless method and theorizing bla bla bla bla , ethylamine is produced in good yields by reduction of nitroethane in many methods for example : zinc/ammonium formate, Al/Hg etc. , reduction of nitrile gives a amine with one carbon more so reduction acetonitrile gives ethylamine , acetonitrile is common solvent, cheap, and easy to buy, reduction cheapest al/hg. Cya

D. Gowda, B. Mahesh, & G. Shankare, Ind. J. Chem. Sect. B, 40, 75-77 (2001)
Syn Comm, Vol 33, No 2, pp 281-289 (2003)
AndersHoveland
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There is not really any easy way for the hobbyist to make ethylamine. The most feasible route would probably be partial oxidation of ethanol to acetaldehyde, then distillation with NH4Cl (or possibly (NH4)2SO4 fertilizer). The procedure would be similar to that used for making methylamine:

 Quote: Methylamine Hydrochloride from Ammonium Chloride and Formaldehyde In a 5 liter round-bottomed flask, fitted with a stopper holding a condenser set for downward distillation and a thermomether which will extend well into the liquid, are placed 4 kg (3711 ml, 47-53 moles) of technical formaldehyde (35-40 percent; d 1.078 at 20°C) and 2 kg (37 moles) of technical ammonium chloride. The mixture is heated on the steam bath until no more distillate comes over and then over a flame until the temperature of the solution reaches 104°C. The temperature is held at this point until no more distillate comes over (four to six hours). The distillate, which consists of methylal (bp 42-43°C), methylformate and water may be treated with NaOH solution to recover methylal and sodium formate. The contents of the reaction flask are cooled too room temp and the ammonium chloride which separates is filtered off. The mother liquor is concentrated on the steam bath under reduced pressure to 2500 ml, and again cooled to room temp, whereupon a second crop of ammonium chloride separates. The total recovery of ammonium chloride up to this point amounts to 780-815 grams. The mother liquor is again concentrated under reduced pressure until crystals begin to form on the surface of the solution (1400-1500 ml). It is then cooled to room temperature, and a first crop of methylamine hydrochloride, containing some ammonium chloride is obtained by filtering the cold solution. At this point 625-660 grams of crude product is obtained. The mother liquor is now concentrated under reduced pressure to about 1000 ml, and cooled, and a second crop of methylamine hydrochloride (170-190 grams) is then filtered off. This crop of crystals is washed with 250 cc of cold chloroform, and filtered to remove most of the dimethylamine hydrochloride which is present. After the washing, the product weighs 140-150 grams. The original mother liquor is then evaporated under reduced pressure, as far as possible, by heating on a steam bath, and the thick syrupy solution (about 350 ml) which remains is poured into a beaker and allowed to cool, with occasional stirring, in order to prevent the formation of a solid cake, and the crystals obtained are washed with 250 ml of cold chloroform, the solution is filtered yielding 55-65 grams of product. There is no advantage in further concentrating the mother liquor, which contains mostly tetramethylmethylenediamine hydrochloride, but no trimethylamine hydrochloride. The total yield of methylamine hydrochloride is 830-850 grams. The product contains water, ammonium chloride and some dimethylamine hydrochloride. In order to obtain a pure product, the impure methylamine hydrochloride is recrystallized from absolute ethanol (solubility 0.6g/100ml at 15°C), or preferably butyl alcohol (even less soluble). The recovery of ammonium chloride amounts to 100-150 grams, making the total recovery 850-950 grams. The yield of recrystallized methylamine hydrochloride is 600-750 grams (45-51 percent of theory, based on the used up ammonium chloride). A standard run, from 250 grams ammonium chloride and 500g 37% formaldehyde (containing 15% methanol), gives 100-134 grams methylamine hydrochloride, 27 grams dimethylamine hydrochloride and 81 grams of recovered ammonium chloride. The distillate contains methylal (formaldehyde dimethyl acetal) and methyl formate, which after treatment with NaOH can yield 25g of sodium formate and 30 grams of methylal, as the compound cannot be separated by fractional distillation, neutralization is the way to go. Ammonium chloride is very sparingly soluble in a concentrated solution of methylammonium chloride, making the separation of the compounds pretty sharp. Similarly, Hexamine and HCl may be used as the reactants instead, illustrating that the order of reaction of CH2O, NH3, and acid does not matter.

Both these procedures were archived from "The Hive".
Waffles SS
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 Quote: Originally posted by AndersHoveland There is not really any easy way for the hobbyist to make ethylamine. The most feasible route would probably be partial oxidation of ethanol to acetaldehyde, then distillation with NH4Cl (or possibly (NH4)2SO4 fertilizer).

Thanks,
I think Hofmann Rearrangement is cheaper and easier method also there is better ways for producing Acetaldehyde
I tried vinyl acetate + aceic acid +catalyst(H2SO4) and got lot of pure acetaldehyde
smaerd
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I was at one point really interested in preparing my own triethylamine seeing as how all tertiary amine proton scavengers are really expensive and darn near unobtainable.

What about the gassing dry ammonia into 90% ethanol solution then adding EtBr?(see attached articles)

I posted before asking for advice on gassing ammonia into ethanol solution and no one cared to lend any tips iirc... My best advice should you try this route is do not use a glass pipet, and find some sort of gas dispersion tube. Not sure how well the inverted funnel trick would work. Unless of course you have at your disposal a dewar style condenser and dry-ice/acetone. Unfortunately I do not.

Attachment: A MODIFIED METHOD FOR THE PREPARATION OF TRIETHYLAMINE.pdf (263kB)

Attachment: The Preparation of Ethylamine and Diethylamine.pdf (253kB)

[Edited on 21-1-2012 by smaerd]

Ephoton
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 Quote: Originally posted by mario840 Hahahahaha i knew it, on this forum are only google-amateur-chemists, to my thread no one can answer because they know nothing more than goole , in this thread as always some useless method and theorizing bla bla bla bla , ethylamine is produced in good yields by reduction of nitroethane in many methods for example : zinc/ammonium formate, Al/Hg etc. , reduction of nitrile gives a amine with one carbon more so reduction acetonitrile gives ethylamine , acetonitrile is common solvent, cheap, and easy to buy, reduction cheapest al/hg. Cya D. Gowda, B. Mahesh, & G. Shankare, Ind. J. Chem. Sect. B, 40, 75-77 (2001) Syn Comm, Vol 33, No 2, pp 281-289 (2003)

Are you alright in the head or what ?

Hope you know your posting missinformation when you say that
you can reduce a nitrile with Al/Hg amalgums.

Anyway google doesnt work with tar button so I think you will find
a lot of us dont even use google anymore.

If we could reduce nitriles with amalgums PEA's would be a different kettle of fish.

bash-2.05#

Waffles SS
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 Quote: Alcoholysis of sulfamic acid produces ammonium akyl sulfates. On page 629 of the attached article it discusses an example where methanol refluxed with sulfamic acid for several hours yields ammonium methyl sulfate. Ammonium methyl sulfate rearranges at high temperature to methylamine sulfate. See ammonium.methyl.sulfate.pdf here http://psychedelichosting.info/Ionium/Rhodium/pdf or http://80.244.243.200/archive/rhodium/pdf/index.html http://www.sciencemadness.org/talk/viewthread.php?tid=1261&a...

What about ammonium ethyl sulfate?it should produce ethyl amine sulfate. isnt it?
Sedit
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No it undergoes an elimination reaction releasing Ethane with no formation of Ethylamine. Since its an Ethylating reagent I am curious weather it can be used to Ethylate an amine so that Ethylamine can be produced but under normal conditions such as that which create methylamine it will not work.

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Could you make Ethyl Bromide and bubble Ammonia gas through that to create a mixture of Ethylamine, Diethylamine, and Triethylamine.

Separate the 3

Ethylamine: BP 16.6 C Miscible in water
Diethylamine: BP 55-56 C Miscible in water
Triethylamine: BP 89-90 C Solubility in water 5.5% at 20°C (So not much)

Could you Distill off the Ethylamine and use the differences in solubility between Diethylamine and Triethylamine to separate the two.
You could probably distill the Di and Tri as they are greater than 25C BP difference.

Am I wrong?

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 Quote: Originally posted by Arsole Could you make Ethyl Bromide and bubble Ammonia gas through that to create a mixture of Ethylamine, Diethylamine, and Triethylamine. Separate the 3 Ethylamine: BP 16.6 C Miscible in water Diethylamine: BP 55-56 C Miscible in water Triethylamine: BP 89-90 C Solubility in water 5.5% at 20°C (So not much) Could you Distill off the Ethylamine and use the differences in solubility between Diethylamine and Triethylamine to separate the two. You could probably distill the Di and Tri as they are greater than 25C BP difference. Am I wrong?

In principal you are right but the reaction would probably require sodium amide in liquid ammonia to proceed at a decent rate. Separating the product would be hard as well.
OK if you have an industrial plant with 50m fractionating towers but tough in a lab.
Ethylamine is a bit of a bugger to handle when pure as it boils below average room temperature in most labs.
For a lot of purposes an aqueous solution is adequate and a lot cheaper.
If I had to make it I would go for the Gabriel synthesis.
http://en.wikipedia.org/wiki/Gabriel_synthesis
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 Quote: Originally posted by Arsole Could you Distill off the Ethylamine and use the differences in solubility between Diethylamine and Triethylamine to separate the two.

I don't think you could use water solubility to separate them, as once you add diethylamine to water, you create a new mixture, which would readily dissolve triethylamine. Remember solubilities are determined with single, pure compounds, and most impure chemicals are much more soluble, as well as the effect of adding a new chemical to the solvent changes its solvent properties, and almost always makes a better solvent. For example, many paint strippers are a mix of non-polar and polar solvents, as that will dissolve much faster and much more stuff than any one solvent would do. So purification of mixtures of liquids by solubility generally does not work well.

However, A decent still with even a moderate distillation column can separate liquids of different BPs quite well, if the distillation is done slowly and carefully controlled. I have distilled Freon isomers from each other which only had a 1-3 C difference in BP, using a 3' fractionating column, but for over 10C, it is not hard to distill compounds apart to a reasonable purity. Plus, if you want diethylamine, having a trace of triethylamine would generally not hurt, is it is mostly non-reactive. Same way, you could remove traces of DEA from TEA by reacting the DEA with a chemical that would form a new compound and then distill off the TEA. It would be a pain, but I have done such things before in a pinch.
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 Quote: Originally posted by ScienceSquirrel In principal you are right but the reaction would probably require sodium amide in liquid ammonia to proceed at a decent rate. Separating the product would be hard as well. OK if you have an industrial plant with 50m fractionating towers but tough in a lab. Ethylamine is a bit of a bugger to handle when pure as it boils below average room temperature in most labs. For a lot of purposes an aqueous solution is adequate and a lot cheaper. If I had to make it I would go for the Gabriel synthesis. http://en.wikipedia.org/wiki/Gabriel_synthesis

Thanks ScienceSquirrel ,
This is really interesting method
Also In the final step we can use basic solution instead of hydrazine(due to Toxicity of hydrazine)
Ethyl chloride easily can be made by ethanol and hydrochloric acid.
Do you know ratio or Instructions (example) for this method?
I think this method is easier than Hofmann Rearrangement method.I want to test this method

[Edited on 9-2-2012 by Waffles SS]
Nicodem
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 Quote: Originally posted by Waffles SS Ethyl chloride easily can be made by ethanol and hydrochloric acid.

Easily? Please post the reference or the experimental data so we can judge by our selves.
entropy51
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 Quote: Originally posted by Waffles SS Thanks ScienceSquirrel , This is really interesting method Also In the final step we can use basic solution instead of hydrazine(due to Toxicity of hydrazine) Ethyl chloride easily can be made by ethanol and hydrochloric acid. Do you know ratio or Instructions (example) for this method? I think this method is easier than Hofmann Rearrangement method.I want to test this method
Ethyl bromide is more easily made than ethyl chloride. Different members have reported preps for EtBr on the forum. Basically it just requires the distillation of a mixture of ethanol, NaBr and H2SO4 with very cold water in the condenser.

I believe the protocol for the Gabriel synthesis of primary amines is in Vogel's textbook of practical organic chemistry in the forum library. It is not a trivial exercise, but is not too difficult, especially if you can get phthalimide.

There are several threads pertaining to the preparation of ethyl chloride. Here is one of them: https://www.sciencemadness.org/whisper/viewthread.php?tid=13...

[Edited on 10-2-2012 by entropy51]
Waffles SS
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Quote: Originally posted by Nicodem
 Quote: Originally posted by Waffles SS Ethyl chloride easily can be made by ethanol and hydrochloric acid.

Easily? Please post the reference or the experimental data so we can judge by our selves.

In below topic you can find it:
Ethanol + hydrochloric acid + ZnCl2(catalyst)
Yield is low but this is possible.
I think this method is cheaper , easier and safer than EthylBromide route and it doesnt need special equipment
this mean for me Easily

 Quote: The successful conversion of methyl and ethyl iodides into the N-alkylphthalimides by reaction with potassium phthalimide at 150°C was reported by Craebe and Pictet in 1884. It was already known that N-alkylphthalimides could be hydrolyzed to phthalic acid and the primary amine, but it was Gabriel who appreciated the significance of these reactions and formulated the Synthesis which bears his name. The Gabriel Synthesis of Primary Amines Prof. M. S. Gibson1, Dr. R. W. Bradshaw2,* Article first published online: 17 DEC 2003 DOI: 10.1002/anie.196809191

The biggest problem is boiling point of ethyl halide(<100c)
This reaction happen near 150c and ethyl chloride or ethyl bromide boil below 100c.
I think i should gases ethyl halide into warm(150C) potassium phthalimide

[Edited on 10-2-2012 by Waffles SS]
Waffles SS
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What about reduction of Nitroethane by(Sn/HCl)?

 Quote: 2 CH3NO2 + 6 Sn + 12H+ 2 CH3NH2 + 3 Sn(IV) + 4 H2O Cognate procedure: Setup a flask with reflux condenser in which .25 mol of nitromethane, .38 mol of granulated tin metal and a stirrer magnet have been added. Carefully pour 115mL of 31.45% hydrochloric acid (muriatic acid) down the reflux condenser in 10-15mL increments, waiting for the reaction to settle down before pouring the next aliquot. If the reaction seems to get out of hand (excessive frothing, vapor escaping the reflux condenser, etc...) then quickly slide an ice bath in place until it slackens back down. Once all the HCl has been added, heat the mixture to reflux with an electric mantle for 1hr. At the end of this time, allow to cool, preferably in an ice bath, then add, carefully, a chilled solution of 75g sodium hydroxide in 125mL of water. If the flask contents start to bubble violently you will watch your yield go out the window, so add slowly! Since methylamine readily dissolves in water, you will need to distill the reaction contents carefully to first liberate the 40% constant boiling solution (bp: 53°C) and then the gas itself. The product is best captured by bubbling the distillation vapor into a beaker of hydrochloric acid (use a slight molar excess of HCl to insure no loss). Proceed as above by evaporating the bubbler solution to yield the crystals (take care when evaporating HCl solutions, as the excess acid will vaporize into the air, corroding ovens, lungs, etc...). [Vogel's, pg 892]

We can use Nitroethane instead of nitrimethane in above procedure

Nitro ethane can be prepared by below method:

Nitroethane from ethylsulfate, Desseigne variation.
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Yep, nitroethane is the simplest of materials to access Ain't no issues with the synthesis of that shit...

If monoethylamine, without di- and tri-ethylamine, is the target might I suggest the Hoffman is probably the best option for the amateur chemist. Fucking around with phthaloyl groups for a low value intermediate would appear to be overkill.

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