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trip96
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[*] posted on 23-7-2012 at 20:49
Basic Solvent Choice


Hey guys, let me start by saying I have no experience in chemistry but I have started dabbling as a hobby.

I have a question. I wish to extract Conessine (http://www.worldofchemicals.com/wochem/pub/chemconessine.htm...) from the bark of Funtumia elastica tree.

I know that this compound is an amine and probably would dissolve readily in organic solvents. My question is how do you choose your solvent? I only have access to OTC solvents too.

Any help would be appreciated in answering this basic question.

My first thought is ethanol.
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[*] posted on 24-7-2012 at 02:50
Solvent Choice


Ethanol might work. Remember that "like dissolves like", and given its relatively low hetero-atom/carbon ratio I would shoot for something even less polar. Im not completely sure what all you can get OTC, but acetone or similar would be my personal starting point. It seems like you can get THF/toluene from various glues ect, that might be worth a try as well.
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[*] posted on 24-7-2012 at 05:10


Tough choice of target for a beginner. Check out the isolation procedure (under materials and methods) described here:
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2816488/
Flash chromatography on alumina using hexane and ethyl acetate, twice over (after the primary extraction using methanol/HCl/ammonia/ethyl acetate).
I expect there are just too many similar-yet-slightly-different compounds alongside the conessine for non-chromatographic isolation to be feasible.




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[*] posted on 24-7-2012 at 14:24


Thanks guys! That paper you linked is perfect!

I don't know if I need to isolate the compound or not and I definitely don't have the right equipment for chromatography and no skill for that either; its seems to be an 'art'.

I wonder how potent a solution you could have with say a decent distillation kit. Perhaps boil off a lot of the other substances as connessine has a higher boiling temperature of 450 degrees C.

thanks again for the help so far.
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[*] posted on 25-7-2012 at 02:24


At that temperature you'd expect a fair amount of decomposition. I suspect that is an extrapolated boiling point, derived from a nomograph and distillation at (very) reduced pressure.
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[*] posted on 26-7-2012 at 07:57


O.K. so distillation is off the table.

What about an acid / base extraction? it is an alkaloid. Perhaps in naptha and water? change the alkaloid to its salt and then drain off the water layer and evaporate? That will give me all the alkaloids from the plant material correct? (Then you could do a chromatography to isolate the Conessine).

Also, how do you determine the Ph levels needed so I don't just ruin the alkaloid I am looking for by adding too much acid?

It's really cool that you guys help out with such basic questions on this forum. I browsed other threads and some conversations are crazy complicated. It really is nice to get into organic chemistry with a good group of people to bounce ideas off.
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[*] posted on 26-7-2012 at 14:19


The polycyclic structure (largely aliphatic as well) and lack of significantly electronegative atoms leads me to believe that heptane or a similar hydrocarbon solvent would be a good candidate, followed by acid-base extraction (amines form salts) and then chromatography or further isolation procedures.
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[*] posted on 27-7-2012 at 12:12


When you're choosing a solvent, you have to consider specific solvent-solute interactions. "Like dissolves like" is often correct but is not the entire picture.

There are two tertiary amines in the structure of conessine and both have lone electron pairs hanging off of them. These lone pairs can be protonated under acidic conditions, which would render the molecule more water soluble. HOWEVER, acid-base extraction may not be a good idea: the double bond in the second ring is acid-labile. It would react under strongly acidic conditions to form an addition product.

Chloroform, which is mildly acidic, would be a good solvent. The electron-poor hydrogen would "stick" to the tertiary amines and bring the molecule into solution. Chloroform is also easily evaporated, making purification that much easier.

There is a very detailed thread on the preparation of chloroform from acetone and bleach on these very forums. It is within the reach of the amateur.




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[*] posted on 10-2-2018 at 17:27




Chloroform, which is mildly acidic, would be a good solvent. The electron-poor hydrogen would "stick" to the tertiary amines and bring the molecule into solution. Chloroform is also easily evaporated, making purification that much easier.

There is a very detailed thread on the preparation of chloroform from acetone and bleach on these very forums. It is within the reach of the amateur.[/

I am new here. Hello. I am an amateur chemist and model rocket hobbyist. I don't work, on social security disability and cared for by other family members who can handle dealing with humans, because I have trouble with doing that. All of my chemicals have been collected from "otc" sources that never come in the mail bc I don't have credit card or cards and refuse to ask family to buy things bc I don't like trying to explain what the hypothetical item would be used for to make. I will do my best to make clear what I mean, I have Aspergers, so I apologize for any unclear text. Ask me for clarification where needed. I was educated by the public school system so I really apologize for my ignorance as to proper stoichiometry and proper chemistry with respect to the those of you who I learn much from on here. I have a peace playing with the Legos of the universe (I heard this name for atoms and like it) so my interest in chemistry is my hobby is my life. I have no children and thankfully no spouse. I tried that once and had my heart broken until I reverted back to what I always loved and what always was faithful to me too, that which maybe leads you to read this, unless you are one of the workers on this forum/site in which case computers maybe for you. Ok, sorry for disclaimer and excuses. Just know that I am not dangerous or stupid or disrespectful. Anyways..
There are a few examples of this prep on YouTube. The haloform reaction, creating acetic acid and chloroform from reacting acetone and bleach or even propionic acid and chloroform from MEK and bleach. I'm curious of all the acids that can be made from their respective ketones when utilized in this manner. I was a little successful following some of these videos when I used acetone, which was my first attempt. I was far, far more successful and had a near quantitative yield following a video (I'm very sorry, i don't remember who posted the video that gave me my success, nor do I know exactly how to provide a link to the video. I will do my best to describe the video though). In this video a man is on a screened-in porch with, I think, a swimming pool. He used a bucket with ice, explaining that the ice was needed bc the reaction gets warm, perhaps hot with higher hypochlorite concentrations or larger reactions in general. This ice was the key to my success. I want to say he explained the molar ratio of adding the ketone to hypochlorite bleach, coming up with something like 49cc acetone to one and half gallon bleach, bleach being 6.75 (the standard number, again apologies for if my percentage number wrong. I'm positive it was 6.25 or 6.75). I had run out of acetone but had a can of MEK, thinking I might try to make some of this propionic acid, as it had a use in the reaction to create pyrimethamine, as nurdrage had said. I was interested in attempting this at first, but chose against it due to lack of materials and experience thus far. Propionic acid has many uses in organic chemistry. So here's what I did: I went to rite aid pharmacy and purchased three half gallon bottles of bleach, an oral syringe (10 cc) with volumetric measurements in both metric and imperial (is imperial the right name for the kind America uses?) and a small bottle of 100% acetone nail polish remover (I decided to make chlorbutanol and this requires chloroform and acetone with alkali hydroxide catalyst) spending less than ten dollars total. I filled a gallon ziploc bag with ice cubes three times, went out to garage and put these into a five gallon bucket (each time)along with all of the bleach, 1.5 gallons. Sorry, don't recall metric equivalent to this. I will google...5.67811768 liters. Ok so then I added drop wise, 52ml of methyl ethyl ketone, stirring occasionally. There were many ice cubes, easily more ice than fluid, at first. I had very crude equipment, choosing to use a wooden broomstick as a stirring rod, which, oddly, did not negatively effect my yield. I stirred, slowly, maybe one rpm per second. After about fifteen minutes the reaction began and the solution which was clear-yellow like champagne but with lots of ice cubes became cloudy and much easier to stir as ice cubes melted and became smaller. I continued to stir with the upside down broom for 45 minutes, satisfied that the need for more stirring was not necessary anymore. I went in, got more ice, came back out and added these, stirring a little more. I brought the bucket out of the garage and put on the side of the house, with a lid on top, loosely placed. This was done on a late Spring afternoon in 2017, maybe it was May. I left this bucket for the night. The next morning I went around to the side of the house and was excited to see that I had succeeded. I think that the extra 3 ccs of MEK was good measurement bc my yield was nearly exactly the same number, maybe just less than this. What I like about chloroform is that it is more dense than water and thus sinks in water! This is very convenient bc chcl3 is very volatile, evaporating easily as fast as the original ketone, if not even faster. This is also very convenient if you want to use this for a solvent. Storing is easy even if it gets warm bc you can put it in a water bottle under water so it won't pop the bottle. My next adventure will be to make potassium permanganate. I have the innards of an alkaline d cell battery. I will attempt by using bleach, or maybe kno3. Thank you for your time. Thank you for your wisdom.
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[*] posted on 10-2-2018 at 18:43


Quote: Originally posted by Omniquist  


Chloroform, which is mildly acidic, would be a good solvent. The electron-poor hydrogen would "stick" to the tertiary amines and bring the molecule into solution. Chloroform is also easily evaporated, making purification that much easier.

There is a very detailed thread on the preparation of chloroform from acetone and bleach on these very forums. It is within the reach of the amateur.[/

I am new here. Hello. I am an amateur chemist and model rocket hobbyist. I don't work, on social security disability and cared for by other family members who can handle dealing with humans, because I have trouble with doing that.

All of my chemicals have been collected from "otc" sources that never come in the mail bc I don't have credit card or cards and refuse to ask family to buy things bc I don't like trying to explain what the hypothetical item would be used for to make.

I will do my best to make clear what I mean, I have Aspergers, so I apologize for any unclear text. Ask me for clarification where needed.

I was educated by the public school system, so I really apologize for my ignorance as to proper stoichiometry, and proper chemistry with respect to the those of you who I learn much from on here.

I have a peace playing with the Legos of the universe (I heard this name for atoms and like it), so my interest in chemistry is my hobby is my life.

I have no children and thankfully no spouse. I tried that once and had my heart broken, until I reverted back to what I always loved and what always was faithful to me too.

That which maybe leads you to read this, unless you are one of the workers on this forum/site in which case computers maybe for you. Ok, sorry for disclaimer and excuses.

Just know that I am not dangerous or stupid or disrespectful. Anyways..

There are a few examples of this prep on YouTube. The haloform reaction, creating acetic acid and chloroform from reacting acetone and bleach or even propionic acid and chloroform from MEK and bleach.

I'm curious of all the acids that can be made from their respective ketones when utilized in this manner. I was a little successful following some of these videos when I used acetone, which was my first attempt.

I was far, far more successful and had a near quantitative yield following a video (I'm very sorry, i don't remember who posted the video that gave me my success, nor do I know exactly how to provide a link to the video.

I will do my best to describe the video though). In this video a man is on a screened-in porch with, I think, a swimming pool.

He used a bucket with ice, explaining that the ice was needed bc the reaction gets warm, perhaps hot with higher hypochlorite concentrations, or larger reactions in general.

This ice was the key to my success. I want to say he explained the molar ratio of adding the ketone to hypochlorite bleach, coming up with something like 49cc acetone to one and half gallon bleach, bleach being 6.75 (the standard number, again apologies for if my percentage number wrong.

I'm positive it was 6.25 or 6.75). I had run out of acetone but had a can of MEK, thinking I might try to make some of this propionic acid, as it had a use in the reaction to create pyrimethamine, as nurdrage had said.

I was interested in attempting this at first, but chose against it due to lack of materials and experience thus far. Propionic acid has many uses in organic chemistry. So here's what I did:

I went to rite aid pharmacy and purchased three half gallon bottles of bleach, an oral syringe (10 cc) with volumetric measurements in both metric and imperial (is imperial the right name for the kind America uses?), and a small bottle of 100% acetone nail polish remover.

I decided to make chlorbutanol and this requires chloroform and acetone with alkali hydroxide catalyst, spending less than ten dollars total.

I filled a gallon ziploc bag with ice cubes three times, went out to garage and put these into a five gallon bucket (each time)along with all of the bleach, 1.5 gallons.

Sorry, don't recall metric equivalent to this. I will google...5.67811768 liters. Ok so then I added drop wise, 52ml of methyl ethyl ketone, stirring occasionally.

There were many ice cubes, easily more ice than fluid, at first. I had very crude equipment, choosing to use a wooden broomstick as a stirring rod, which, oddly, did not negatively effect my yield.

I stirred, slowly, maybe one rpm per second. After about fifteen minutes the reaction began and the solution which was clear-yellow like champagne but with lots of ice cubes became cloudy and much easier to stir as ice cubes melted and became smaller.

I continued to stir with the upside down broom for 45 minutes, satisfied that the need for more stirring was not necessary anymore. I went in, got more ice, came back out and added these, stirring a little more.

I brought the bucket out of the garage and put on the side of the house, with a lid on top, loosely placed. This was done on a late Spring afternoon in 2017, maybe it was May.

I left this bucket for the night. The next morning I went around to the side of the house and was excited to see that I had succeeded.

I think that the extra 3 ccs of MEK was good measurement bc my yield was nearly exactly the same number, maybe just less than this. What I like about chloroform is that it is more dense than water and thus sinks in water!

This is very convenient bc chcl3 is very volatile, evaporating easily as fast as the original ketone, if not even faster.

This is also very convenient if you want to use this for a solvent. Storing is easy even if it gets warm bc you can put it in a water bottle under water, so it won't pop the bottle.

My next adventure will be to make potassium permanganate. I have the innards of an alkaline d cell battery. I will attempt by using bleach, or maybe kno3. Thank you for your time. Thank you for your wisdom.


I only tried to make it a little easier to read, I figured a fair few wouldnt try and read a big block.

My english skills are not great, but i do hope splitting it up a little, gets you some answers. Welcome to the forum

Nick
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WangleSpong5000
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[*] posted on 16-2-2018 at 21:35


Quote:
Quote: Originally posted by Omniquist  


Chloroform, which is mildly acidic, would be a good solvent. The electron-poor hydrogen would "stick" to the tertiary amines and bring the molecule into solution. Chloroform is also easily evaporated, making purification that much easier.

There is a very detailed thread on the preparation of chloroform from acetone and bleach on these very forums. It is within the reach of the amateur.[/

I am new here. Hello. I am an amateur chemist and model rocket hobbyist. I don't work, on social security disability and cared for by other family members who can handle dealing with humans, because I have trouble with doing that. All of my chemicals have been collected from "otc" sources that never come in the mail bc I don't have credit card or cards and refuse to ask family to buy things bc I don't like trying to explain what the hypothetical item would be used for to make. I will do my best to make clear what I mean, I have Aspergers, so I apologize for any unclear text. Ask me for clarification where needed. I was educated by the public school system so I really apologize for my ignorance as to proper stoichiometry and proper chemistry with respect to the those of you who I learn much from on here. I have a peace playing with the Legos of the universe (I heard this name for atoms and like it) so my interest in chemistry is my hobby is my life. I have no children and thankfully no spouse. I tried that once and had my heart broken until I reverted back to what I always loved and what always was faithful to me too, that which maybe leads you to read this, unless you are one of the workers on this forum/site in which case computers maybe for you. Ok, sorry for disclaimer and excuses. Just know that I am not dangerous or stupid or disrespectful. Anyways..
There are a few examples of this prep on YouTube. The haloform reaction, creating acetic acid and chloroform from reacting acetone and bleach or even propionic acid and chloroform from MEK and bleach. I'm curious of all the acids that can be made from their respective ketones when utilized in this manner. I was a little successful following some of these videos when I used acetone, which was my first attempt. I was far, far more successful and had a near quantitative yield following a video (I'm very sorry, i don't remember who posted the video that gave me my success, nor do I know exactly how to provide a link to the video. I will do my best to describe the video though). In this video a man is on a screened-in porch with, I think, a swimming pool. He used a bucket with ice, explaining that the ice was needed bc the reaction gets warm, perhaps hot with higher hypochlorite concentrations or larger reactions in general. This ice was the key to my success. I want to say he explained the molar ratio of adding the ketone to hypochlorite bleach, coming up with something like 49cc acetone to one and half gallon bleach, bleach being 6.75 (the standard number, again apologies for if my percentage number wrong. I'm positive it was 6.25 or 6.75). I had run out of acetone but had a can of MEK, thinking I might try to make some of this propionic acid, as it had a use in the reaction to create pyrimethamine, as nurdrage had said. I was interested in attempting this at first, but chose against it due to lack of materials and experience thus far. Propionic acid has many uses in organic chemistry. So here's what I did: I went to rite aid pharmacy and purchased three half gallon bottles of bleach, an oral syringe (10 cc) with volumetric measurements in both metric and imperial (is imperial the right name for the kind America uses?) and a small bottle of 100% acetone nail polish remover (I decided to make chlorbutanol and this requires chloroform and acetone with alkali hydroxide catalyst) spending less than ten dollars total. I filled a gallon ziploc bag with ice cubes three times, went out to garage and put these into a five gallon bucket (each time)along with all of the bleach, 1.5 gallons. Sorry, don't recall metric equivalent to this. I will google...5.67811768 liters. Ok so then I added drop wise, 52ml of methyl ethyl ketone, stirring occasionally. There were many ice cubes, easily more ice than fluid, at first. I had very crude equipment, choosing to use a wooden broomstick as a stirring rod, which, oddly, did not negatively effect my yield. I stirred, slowly, maybe one rpm per second. After about fifteen minutes the reaction began and the solution which was clear-yellow like champagne but with lots of ice cubes became cloudy and much easier to stir as ice cubes melted and became smaller. I continued to stir with the upside down broom for 45 minutes, satisfied that the need for more stirring was not necessary anymore. I went in, got more ice, came back out and added these, stirring a little more. I brought the bucket out of the garage and put on the side of the house, with a lid on top, loosely placed. This was done on a late Spring afternoon in 2017, maybe it was May. I left this bucket for the night. The next morning I went around to the side of the house and was excited to see that I had succeeded. I think that the extra 3 ccs of MEK was good measurement bc my yield was nearly exactly the same number, maybe just less than this. What I like about chloroform is that it is more dense than water and thus sinks in water! This is very convenient bc chcl3 is very volatile, evaporating easily as fast as the original ketone, if not even faster. This is also very convenient if you want to use this for a solvent. Storing is easy even if it gets warm bc you can put it in a water bottle under water so it won't pop the bottle. My next adventure will be to make potassium permanganate. I have the innards of an alkaline d cell battery. I will attempt by using bleach, or maybe kno3. Thank you for your time. Thank you for your wisdom.


Hey man. don't ever apologise for who you are. I've been on disability benefits for 17 years. I don't work either... I haven't because I don't need to and I don't care to. I only ever get jobs when girlfriends make me get them lol at my age girls are obsessed with having kids which I have to pay for of course... that's evolution for you hahah

I have severe OCD so a know what it means to be an autist in this world of Normalo
dullards. Be proud! I'm an autistic superstar and my life rocks. Remember, you're on the spectrum. Your likely smarter than 95%!of the population so don't pay a mind to anyone that ever gives you a hard time for being a mental head as they are stupid and with any luck in the near future they will all be residing in my gulag on the moon hahahaha.

Solvents for extracting alkaloids? I was under the impression that smaller amines such those akin to a phenethlamine (or catecholamine) like structure are best dissolved in solvents such as chloroform, DCM but I think things such as naphtha and ether work quite well also. Now for tyrptamine type substances I always heard that the latter more non polar solvents were preferable, but i have no idea and am a little sketchy as too the finer details of the solubility properties of substances that are fairly similar re dipole moments and solvents that are neither NP or P...

I do realise that chemicals derived from plants vary a lot more than the above but a lot a very similar... hmmm interesting





Hyperbole be thy name
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