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What's the solubility of fumaric acid in boiling water? Options
 
N6
#1 Posted : 9/14/2012 9:56:59 PM
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So today I did the following experiment:

I brought 200ml of distilled water to boil and kept adding 1.2g of fumaric acid while keeping the water boiling. I managed to add 11g of fumaric acid before it wouldn't dissolve any more.

According to Wikipedia, the solubility of fumaric acid in water is 0.63 per 100ml which means I added 9 times as much (well, actually more because I was slow and some water evaporated in the process). I've actually been looking for information on solubility at different temperatures but haven't found anything.

I use FASW to salt out from d-limonene and what I was thinking was that I could use much less FASW if it was more concentrated and that it would therefore save from the trouble of reducing it. Also, having both FASW and d-limonene hot when salting would eliminate emulsions.

I'll report back when I have the chance to try it myself.

P.S. Thanks for full membership after just one post.
 

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Auxin
#2 Posted : 9/16/2012 2:55:18 AM

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According to the CRC (Ed. 36 (1954-55), my favorite edition):
To 100 ml of water you can dissolve 0.70 g @ 25°C or 9.8 g @ 100°C
To 100 ml of 95% ethanol you can dissolve 5.75 g @ 29.7° or 4.76 g @ 76° (no, I didnt copy those backwards)
To 100 ml of ether you can dissolve 0.72 g @ 25°C

I love those old CRCs because in my newer one, 69th edition (1988-89), all that info was removed to save space.

Eighth edition of the Merck Index ( 1968 ) differs very slightly. It says to 100 grams of water you can dissolve:
0.63 g @ 25°C
1.07 g @ 40°
2.4 g @ 60°
9.8 g @ 100°
In 100 grams 95% ethanol you can dissolve:
5.76 g @ 30°
In 100 grams acetone you can dissolve:
1.72 g @ 30°
And it specifies its almost insoluble in olive oil Laughing
 
N6
#3 Posted : 9/16/2012 1:23:48 PM
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Thanks for the information, it's been added to the wiki. I guess all the info is out there, you just have to know where to look.

That means I can salt all my pulls with double-strength boiling FASW without even heating d-limonene.
 
benzyme
#4 Posted : 9/16/2012 5:15:37 PM

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just curious, why would you not heat the limonene?
it is rather nonpolar, and dmt free base isn't very soluble in it (thus people having to use multiple pulls). heating the solvent helps increase the solubility
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
N6
#5 Posted : 9/16/2012 6:54:03 PM
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I haven't thought of heating it for the pulls. I thought DMT is very soluble in it, certainly more so than in petroleum ether or xylene? (That's just what I've read on the forums.) Anyway, I always use a generous amount otherwise I can't pull a high enough percentage off (in BLAB, when I added 100ml I could pull only 60ml off!).

I don't want the FASW+d-limonene to be too hot because I use an ordinary (not borosicilate) glass jar and shake it to salt out the DMT, and it would break if the temperature was too high. 40°C is safe.
 
benzyme
#6 Posted : 9/16/2012 7:04:20 PM

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N6 wrote:
I thought DMT is very soluble in it, certainly more so than in petroleum ether or xylene?


no.

maybe more soluble than pet. ether, but certainly not xylene. dmt is very soluble in xylene. this is the reason xylene is not effective in freeze precipitation, but naphtha is (I'd assume limonene as well)

and as long as you're not heating up the glass directly on a burner, you probably don't have to worry about breakage. limonene will not degrade glass, just heat up some water in the microwave, and let the container with limonene sit in it for a few minutes.

keep in mind, this is just to help you pull dmt from the basic water. you don't necessarily
need to heat the fumaric acid, it will readily complex with the free base alkaloids in the solvent, forming alkaloid salts.
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
N6
#7 Posted : 9/16/2012 7:40:46 PM
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My idea was as follows: 100ml of 100°C FASW (containing 1.07g of fumaric acid) is added to 400ml of 25°C d-limonene in a glass jar. This brings down the temperature of the FASW and d-limonene to 40°C, which is just high enough for excess fumaric acid not to start crashing out from the water before I even shake the jar but not hot enough for the jar to break when shaking (I've broken one jar before that way - the bottom fell off).

Doubling the amount of fumaric acid in FASW is just a means of salting twice the amount of DMT from d-limonene without using doubling the amount of water.

I never intended to pull from basic solution with hot d-limonene although I see that may be a good idea. And I'm 100% sure you can't freeze precip it. I'm sorry if I was being unclear.
 
benzyme
#8 Posted : 9/16/2012 7:55:18 PM

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calculations are all fun and good, but are moot if the conc. of dmt in solution is unknown.
fumaric acid (being a diprotic acid) has two pKa's. it is very easy to
overestimate yields due to excess salts.
"Nothing is true, everything is permitted." ~ hassan i sabbah
"Experiments are the only means of attaining knowledge at our disposal. The rest is poetry, imagination." -Max Planck
 
 
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