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MagicJigPipe
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1-amino-2-propanol
I know that not to many people have a use for this substance but I do and maybe I can interest a few other people in it's synthesis.
I've been trying to figure out a decent synth for 1-amino-2-propanol (monoisopropanolamine) for months to no avail. At least not one that uses normal
lab conditions and quasi-OTC chems.
So I guess the question I am asking is:
How can I replace a hydrogen on the first carbon (on isopropanol chain) with an amino group using lab conditions and ~OTC chemicals?
And also, I know there are lots of OTC cleaning products that contain this chemical but I can't find any that have a significant amount that can be
isolated without A LOT of work and equipment.
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Maja
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Try to use search button. I promise you will find answers to all your questions.
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MagicJigPipe
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Nothing about 1-amino-2-propanol. There's even nothing about secondary amino alcohols at all. Trust me, I've been looking all over the internet and
reading all kinds of organic chem books and for some reason I can't find ANYTHING on synthesis of 2ndary amino alcohols in a lab setting. Very
frustrating. Guess I will just continue to advance my chemistry knowledge until I can figure it out myself.
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Boomer
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The compound name rang a bell, and yes there is an idea that I postphoned indefinitely due to it being above my skills.
Does it require an Eschweiler-Clarke methylation to 1-dimethylamino-2-propanol, then a chlorination to 1-dimethylamino-2-chloropropane?
Is a nitrile the second main precursor, and a Grignard the crucial step?
In that case, good luck. I hope you are not after the money, though I don't know if there even is a market in yout country.
For me, it's always a "Why does the dog lick ... ? Becaus it can!" sort of thing. All my HE tests were not to open up safes, blackmail the railway, or
kill personal enemies either, but just done to see what is possible.
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Eclectic
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Propylene Oxide and Ammonium Hydroxide
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MagicJigPipe
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You know what eclectic, I thought of that before but immediatley wrote it off because I figured the hydroxyl group would be placed at the end of the
chain. Which, now that I think about it wouldn't be problem but this seems to be my solution. Thank you, Eclectic.
Hmmmmm... Maybe I should go synthesize Methadone and sell it to orphans just so I could say it was Sauron's fault.
HA!! No, I'm not like that.
And Boomer, as far as that stuff goes, you are exactly correct. I agree with you 100 percent. Even though I haven't done anything significant as far
as drugs go in years. I would be the kind of person to synth something just to see if I can. I have created KCN before and I didn't use it to poison
anyone and I haven't used it in a synth yet but I did it and I got great satisfaction from doing it.
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MagicJigPipe
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Damn, I just realized that the oxygen atom on propylene oxide is connected to carbons 1 & 2 on the propane chain. No shit! I can't believe I
missed this before. This is why it can make 1-amino-2-propanol when combined with ammonia in the right proportions.
This forum kicks ass. With the exception of Mr. Moral Moralton here.
[Edited on 20-9-2007 by MagicJigPipe]
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Polverone
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More chemistry, less squabbling, please.
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MagicJigPipe
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Yes, I agree. It seems as though 2-amino-1-propanol will be created as well. Is this correct?
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Eclectic
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Not much. Read the reference I gave you.
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MagicJigPipe
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I stumbled onto this after "UTFSE" and I remembered a question I had but never asked. I think this was my first post!
I know propylene glycol is made by adding water to propylene oxide. Since aqueous ammonia is used in the procedure, wouldn't an appreciable amount of
the diol be created in the process? I wonder what the equilibrium is for the particular reaction. Perhaps an excess of ammonia solution should be
used. Maybe that's what the original paper called for but I can't remember exactly.
"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any
question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and
that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think,
free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
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Nicodem
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Ammonia is several magnitudes more nucleophilic than water.
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MagicJigPipe
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Yes, that's why I figured a slight excess of ammonia should be used. As long as there is ammonia in solution there should be very minimal (if any)
glycol byproduct.
Thanks.
"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any
question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and
that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think,
free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
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Nicodem
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No, using a slight excess of ammonia would yield no 1-amino-2-propanol since this is more nucleophilic than NH3 so it gets alkylated further till
tri-(2-hydroxypropyl)amine. Read the experimental in the paper Eclectic linked a few posts above. They used a 100-fold excess of ammonia to inhibit
overalkylation and they nevertheless got a mixture of mono-, di- and trialkylamines. They separated the 1-amino-2-propanol by distillation. The
reaction of water with propylene glycol in neutral to slightly basic conditions is negligible being too slow due to the very low nucleophilicity of
water. The only noteworthy side reactions are the overalkylations.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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MagicJigPipe
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Okay, I get it now. Thanks again. I completely looked over the fact that NH3 could be substituted more than once. I was just making sure there
wasn't something that the paper might have overlooked as far as byproducts go. I kind of want to actually try the reaction but propylene oxide is
semi-expensive and there's really not too many other uses for it that I can think of. So, I would have an $80 gallon of epoxypropane with not too
many uses... Or I'd have a lot of 1-amino-2-propanol to play around with but... Also, not too much to do with it aside from the "usual" stuff. Is
there anything extremely interesting that this amino alcohol can be used for, that you know of?
I actually typed up a short "paper" on everything I learned on the synthesis of this compound (and similar amino alcohols) but I can't find it to save
my life. Sucks. For some reason I was so fascinated how something could have amine and alcohol properties at the same time... I know that's
simplistic but I didn't know then what I know now...
I also like the fact that (in theory) this is a clean reaction forming only water and isopropanolamine (water from the NH4OH and that was already
there).
Anyway, I'm done rambling. Thanks for making me look dumb 
[Edited on 5-13-2008 by MagicJigPipe]
"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any
question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and
that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think,
free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
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smuv
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This could also be made directly from propylene chlorohydrin which should predominantly be 1-chloropropan-2-ol. Synthesis from the epoxide is
probably what is done industrially...however with a choice between two chemicals of roughly equal toxicity, I'd rather work with the one which is
non-volatile.
[Edited on 13-5-2008 by smuv]
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MagicJigPipe
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1-chloropropan-2-ol is not readily available, if at all.
"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any
question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and
that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think,
free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
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DJF90
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Dehydration of either propan-1-ol or propan-2-ol should yeild prop-1-ene. This could then be reacted with an aqeuous solution of hypochloric acid
(perhaps makeable from calcium hypochlorite? just add maybe sulphuric acid to precipitate out the calcium sulphate?) to yeild the chlorohydrin.
Other alternative that I can think of is using aqueous chlorine (or bromine... might be easier to work with) solution without the presence of light
(To avoid free radical substitution), as chlorine gas disproportionates in water to Cl- and OCl- (IIRC).
[Edited on 13-5-2008 by DJF90]
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S.C. Wack
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Propylene is sold at the neighborhood hardware store (black bottles) here just like propane and MAPP. The oxide has some interesting uses.
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Polverone
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Propylene can be treated in water with hypochlorous acid, organic hypochlorites, or chlorine to produce mixed chlorohydrins. Propylene glycol can be
treated with hydrogen chloride to produce the same, though the literature there is mostly older and more sparse (since industry usually wants
propylene glycol from chlorohydrin and not the other way around). I think the desired chlorohydrin forms more readily, at least when using HCl +
propylene glycol. If you're interested in chlorohydrin preparations suitable for the reagent-constrained amateur, there's some good older literature,
though you'll find more about ethylene than propylene, and will have to deal with inconsistent terminology.
All of this is pretty moot if you were just going to buy propylene oxide, though.
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smuv
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Halohydrins and epoxides have been discussed here.
How were you planning to get the epoxide MJP? I think via the chlorohydrin would be the easiest route for this case. Were you considering peracids?
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Polverone
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I think he was planning on just buying it. It seems to be available from at least some hobbyist suppliers as a fuel additive for go-karts. Routes from
the alkene or glycol are still interesting though, as these are far more available to the public in most places.
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MagicJigPipe
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Honestly, if I end up doing this I'm just going to buy the propylene oxide. It's expensive but I'll get a lot of it (relative to how much I need).
$80 a gallon. It's probably impure but that's not too much of a concern for me. Although, it shouldn't be too "dirty" because it's to be used as a
fuel additive.
I thought about calling around to some of the racetracks around here but apparently it's now banned by the NHRA. I'm almost certain that people won't
have something that they can't use in an official race, but I suppose it's worth a try (I might find some nitromethane while I'm at it and both will
certainly be cheaper).
It would be fun to try and make the epoxide myself. Looking at the industrial processes, though, made me think twice about that.
I like the propylene glycol + HCl method that Polverone mentioned. It seems like the boiling points of the different chlorohydrins (does it matter?)
would make them difficult to seperate, though.
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Propylene is sold at the neighborhood hardware store (black bottles) here just like propane and MAPP. The oxide has some interesting uses.
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Surely, you are not in the US because I would have heard of this. I have looked high and low for a source for alkenes to no avail. Not even
ethylene. I heard that some people in agriculture use it to synthetically ripen fruit but (of course) none of the ignorant yokels in my area had any
idea what ethylene or ethene was. That wasn't a surprise. Even if they had it, would they sell it to me? Who knows...
I suppose one of these days I'll get around to producing alkenes from the corresponding alcohols and sulfuric acid but until then, I'm looking for a
source. (even though my want for alkenes isn't related to this procedure).
"There must be no barriers to freedom of inquiry ... There is no place for dogma in science. The scientist is free, and must be free to ask any
question, to doubt any assertion, to seek for any evidence, to correct any errors. ... We know that the only way to avoid error is to detect it and
that the only way to detect it is to be free to inquire. And we know that as long as men are free to ask what they must, free to say what they think,
free to think what they will, freedom can never be lost, and science can never regress." -J. Robert Oppenheimer
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Polverone
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Have you tried asking at welding/industrial gas suppliers? There are torches designed to run with oxygen/propylene. A cursory web search shows that 2
of the 3 gas suppliers in my area with at least a minimal web presence do carry propylene in cylinders, and I'm in the US.
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smuv
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Well thats interesting; I had no idea it was a fuel additive. Propylene is pretty easy to make from isopropanol, since it is a secondary alcohol it
can be dehydrated under much more mild conditions than ethanol is, additionally it yields virtually no ether.
I want to point out that epoxies are pretty serious carcinogens, many of the common carcinogens are carcinogenic because in vivo our body metabolizes
them into epoxides (ex. benzene and toluene).
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