Sciencemadness Discussion Board - n-Butylamine as catalyst / Newbie question

n-Butylamine as catalyst / Newbie question

hamsert - 17-8-2011 at 17:00

Hi all, i'm new to this forum, i know only a bit about chemistry but got very interested about organic chemistry.

I'll be honest, i like some drugs and it makes me very curious how they work, and i was reading a lot about they job in the human body. I've got to a point after studying how they work to find out how they are prepared. I know very well you forumers have a buttload of topics of first-time-chemists asking how to do this and that, i've read a lot of these topics here, but i'm not asking for how to make these things, i've found a lot synthesis theories and started to understand them step by step. I'm such a person who wants to know as much as possible about how stuff work, like chemical reactions this time. I was reading wikipedia for days and nights and other science articles, but i just can't figure out some things.

The first and widely used method that i found is a simple reaction between benzaldehyde and nitroethane producing phenyl-2-nitropropene in presence of catalyst n-butylamine. I'm sorry if i'm talking ignorantly about these things but i don't know all of the terms used in chemistry. So i noticed benzaldehyde is releasing its oxigene atom from its lonely carbon atom (maybe phenyl group?) and i guess the nitroethane is releasing two hydrogene from the middle [the carbon atom between the nitrogene and other carbon] (methyl group?) and they make a double bond between the two carbon atoms, so one free oxygene and two free hydrogene creates one water molecule as a byproduct. But what the n-butylamine does as a catalyst? Does it decompose by the warming and that is helping the molecules releasing they atoms? This is the thing that i just can't understand at all and i don't find any explanation and would be very thankful if someone could explain me what is happening. And please correct me if i'm wrong or talking dumb stuff!

Sorry if anything that i said was inapropriate, and sorry for my english.

Bot0nist - 17-8-2011 at 17:18

Hello hamsert, welcome to SM.

A couple things to get you started on the right track.

Even though what your asking is organic chemistry related, questions that have no sources, are 'remedial', or are broad in scope are best received in the beginnings section. Also questions that seem to pertain to CNS active compounds are generally not well received here and end in detritus. It is NOT against forum policy to discuss such things if it is done in a scientific manner and is not geared toward profit or worded in a 'cook' fashion. You seem to be genuinely interested in the chemical aspect of drugs so you may do fine here, however, tread carefully.

I assume your goal is phenylacetone. You will find a wealth of information on the reaction you are likely seeking on the net. Wiki is a good starting place, but that's it. Try and find some occurrences of its use in reputable chemistry that is not related to amphetamine production. You may find that cook manuals are not very informative or trust worthy.

Also UTFSE right here. This has been discussed with varying degrees of success on this very site.

Try and first learn some basic chemistry that does not deal with fringe topics.

Good luck and try not to get locked up.

hamsert - 17-8-2011 at 18:28

Thank you for the answer.

No, my goal is not to produce anything, i'm just curious in the scientific way. I could've asked anything else, but this arouses my mind the most.

I know what a catalyst is (at least i hope so), that is something that speeds up a reaction. Like when i was making printed circuit boards i did it in Fe3Cl to remove the Cu layer from the board, and i used a bit of Al for catalyst. I think the catalyzation was because the solvent heated up because of the exotherm reaction, and not because of the Al, and the heat was the catalyst. But this case i don't know what the n-butylamine does.

I was reading a lot of topics here about this reaction but i didn't find any information about i don't understand this time. I know i should start with basic things, but i'm not that kind of guy. I have a very logical thinking, i know a lot about electronic, mechanic, programming, i always start with something hard to understand, of course meanwhile i learn the basic stuff time by time, and when i understand the hard part i'm happy i get it. 5 weeks before i didn't know what are single, double, triple bonds, what are methyl, ethyl, propyl, butyl, or alkenes or amines, but while i was searching over the internet i learned them. I always search first, read first and just than ask questions. Now i'm at that point when i've read a lot of stuff and still don't get it (and a bit confused too). If i search i always find such cook-books you are talking about, but they just don't tell me any useful information except what kind of materials have been reacted. Thats why i'm asking this question.

Bot0nist - 17-8-2011 at 18:49

I admit I am not well versed in this particular subject, but I did some digging for you.

<a href="http://pubs.acs.org/doi/abs/10.1021/ja01577a030">This paper </a>may be of value to you.

Also, a more in depth explanation of a <a href="http://en.wikipedia.org/wiki/Catalyst">catalyst</a> .

Maybe the fact that it neutralizes acids in exothermic reactions to form salts plus water, and that it is soluble in all organic solvents.

[Edited on 18-8-2011 by Bot0nist]

DJF90 - 18-8-2011 at 03:39

Look for Henry reaction (and perhaps E1cb mechanism) and preferably Knoevanegel condensation

hamsert - 18-8-2011 at 04:51

Bot0nist: Thank you for the wiki link, i did a mistake, i've read this article in my language on wikipedia and that didn't explain catalysis very well, english article is way more detailful. This things tells me much more than the all article in my language:

Quote:

Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process regenerating the catalyst. The following is a typical reaction scheme, where C represents the catalyst, X and Y are reactants, and Z is the product of the reaction of X and Y:
X + C → XC (1)
Y + XC → XYC (2)
XYC → CZ (3)
CZ → C + Z (4)

So if i get it right the butylamine reacts first with the benzaldehyde or nitroethane, creates a new molecule that can react with the other starting material, they form the product material that has a kind of bond with the butylamine that at the end it "falls off" from the product and the all circle starts again. This sounds cool

I know i should be a well-educated chemist to find out how the XC, the XYC and the CZ look like, but can anyone draw me their structure? I know this is an annoying favour i'm asking for but i guess i never will find out by my own. But when i see the starting materials and the products i can sit over it and find out what happened, and actually that is what i want to do.

DJF90: Thanks for the post i'm checking out now.

hamsert - 18-8-2011 at 14:42

Ok i checked the henry reaction and i think i reacognized something.

I attached the image of my hypothetical theory, please tell me if i get it right or i totally f*cked up the all thing

Edit: Ok i think i already have found a mistake, the H on the phenyl group stays there, so the picture is wrong. Then i don't get it

[Edited on 19-8-2011 by hamsert]

[Edited on 19-8-2011 by hamsert]