Author Topic: propionic anhydride  (Read 1361 times)

hypnos

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propionic anhydride
« on: September 09, 2009, 04:59:23 AM »



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http://en.wikipedia.org/wiki/Propionic_anhydride

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ps.when making the propionic anhydride-two things

>approx how long do you have to heat the sodium hydrogen sulphate-

>why a charcoal fire? is another heat source ok or is something special bout this?

>could you explain this process a little more specifically (and if i'm successful you've got an online mate for life!!!)
« Last Edit: October 01, 2012, 04:20:31 AM by java »
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jon

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Re: propionic anhydride
« Reply #1 on: September 09, 2009, 05:30:18 AM »
okay just heat it until it's no longer molten you need temps like 300C if you got a heating mantle that goes that high hey mo power to ya.

just grind it fine then mix it with any propionate salt in a grinder. the propionate ion should be in 2-1 stochiometry to the pyrosulfate.
so calcium propionate use one to one stochiometry.
swij heats his shit in a grolsh bottle on a water bath at 100 C it can be between 100-140 C for one hour.
then if one is lazy like myself he can just use high temp tubing and duct tape  lead it into another bottle and heat it on the oil bath to distill it.
the oil has to be around 190C
it comes over at a crawl.
halfway through grind up the contents and redistill.
happy nodding!!!

Douchermann

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Re: propionic anhydride
« Reply #2 on: September 09, 2009, 05:47:35 AM »
Hypnos, please either post a method for producing propionic anhydride, or request me to move your question (and jon's followup post) into the short questions thread.  This is in an attempt to reduce the clutter of low information threads or terminal threads.  Thank you much!

Vesp

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Re: propionic anhydride
« Reply #3 on: September 10, 2009, 12:01:16 AM »
This method of producing acyl anhydrides sounds very interesting - at least what I can gather from it one reacts a carboxylate with Na2S2O7.

Please give up more information on it.
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jon

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Re: propionic anhydride
« Reply #4 on: September 11, 2009, 05:27:48 AM »
okay see if jon can find the patent.
shit he can't but in the patent the only thing they do differently  is to use the corresponiding carboxylic acid as a wetting agent.
this would probably save the work of grinding the contents of the distilling flask but imposes the added work of fractioning the acid from the anhydride.
 the patent says pretty much any salt can be used and other self explanatory stuff like it should be free of water well duh?
essentially
na2s2o7 + 2 na(oac) = ch3co2cch3 + 2 na2so4
 just do as described it works out just fine, it keeps swij nodding real hard!
« Last Edit: September 11, 2009, 05:36:02 AM by jon »

Vesp

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Re: propionic anhydride
« Reply #5 on: October 03, 2009, 12:34:14 AM »
How would someone know when all of the NaHSO4 turned into Na2S2O7 after heating?
I've done this before in a metal can and it turned green, and ate away at the metal.  I plan on using a porcelain evaporating dish this time so hopefully that will work out better.

Would you recommend ball milling the two compounds together, or use something like a blender? Do you think yield would be significantly better if it were ball milled?
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bluecurry

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Re: propionic anhydride
« Reply #6 on: October 03, 2009, 01:08:36 AM »
couldn't you mix the two chemicals together in an aqueous solution, then evaporate it to ensure proper mixture?

I would imagine this reaction would be a great thing to do in a high temp. heating mantle and quartz fused 3 neck RBF. definitely worth it considering the numerous applications of propionic anhydride.

2bfrank

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Re: propionic anhydride
« Reply #7 on: October 03, 2009, 01:16:03 AM »
This has been done, and you know when it is finished due to the rock hard salt that if formed..It looses the water, starts to firm up, and then later, it gets like a rock, and that is when hot, and not just when cold...mixing the two salts and heating, one would loose the the acetic aspect of that salt, Id imagine..

Vesp

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Re: propionic anhydride
« Reply #8 on: October 03, 2009, 01:19:36 AM »
Oh so I should expect to see it solidify after heating a while? Thanks for that information! I would have expected it to stay molten - if you have ever done this, any suggestion on how long it takes and what your heat supply was?

You obviously couldn't mix it with water - the Na2S2O7 would react with the water forming NaHSO4 again, and then AcOH would form from that if the acetate were present, or it would form the anhydride which would then react with the water to again form the AcOH and Na2SO4.

Water is the enemy for this type of thing.
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2bfrank

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Re: propionic anhydride
« Reply #9 on: October 03, 2009, 02:26:57 AM »
It took HOURS< over 6 I think it was, and I used, and never will again, a heating mantle that can generate high heat,, but wont do that again, as I dont like the idea of haveing something that hot, and for so long..I think Ill try gas flame, next time,, not a bunsen burner, but one with a good sixe element, or just build myself a fire,,

and yes, it goes solid, and that is the marker for the end of reaction,, solid as in REALLY soled, and no more vapor

Vesp

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Re: propionic anhydride
« Reply #10 on: October 05, 2009, 12:17:05 AM »
Recently I put a bit of NaHSO4 in a porcelain evaporating dish and heated it with a propane torch. It began to melt, and release water. After heating it for less then 10 minutes it stopped releasing the clear steam and a white smoke was then being let off.

I don't think it could have been SO3, I used 93% pool grade NaHSO4. What do you think this white gas is?

I stopped heating it as it was producing way to much of this white gas for where I was doing it.

Did yours let off any white gas? I suppose ammonium bisulfate could be an impurity and it could have been sublimating or perhaps this could have been SO3? I don't know. Using a propane torch, I didn't expect it could go solid as Na2S2O7's melting point is only 400*C  and if the NaHSO4 melts easily with a melting point of 315*C I doubt 400*C would be hard to reach.

I read the decomposition point of Na2S2O7 is only 460*C? If so is it very significant at this point? I guess I was making SO3.

I'll try to regulate the temperature a bit better next time, and work on reacting it with sodium acetate later.


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Douchermann

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Re: propionic anhydride
« Reply #11 on: October 05, 2009, 05:12:44 AM »
attempt to capture the vapors next time.  If it blows up on contact with water, you know what it is hahaha

Vesp

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Re: propionic anhydride
« Reply #12 on: October 06, 2009, 04:28:22 AM »
At or near the boiling point of wax (~400*C) do you think the sodium pyrosulfate or the acetic anhydride formed would react?

If not, this would help prevent any cracking of precious glassware, and increase the ability to magnetically stir and mix the powders/solids if they don't clump together into large rocks.

Wax contracts as it cools, and I think this would prevent any problems happening from melted salts -- if you even melt the salts?
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jon

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Re: propionic anhydride
« Reply #13 on: October 06, 2009, 07:12:40 AM »
well the patent uses the corresponding acid as a wetting agent if that's what your'e asking about one could do this too.

couldn't you mix the two chemicals together in an aqueous solution, then evaporate it to ensure proper mixture?

i would'nt do this for one simple reason --s2o7 is pyrosulfate and could concievably react with water.

*I read the decomposition point of Na2S2O7 is only 460*C? If so is it very significant at this point? I guess I was making SO3.

I'll try to regulate the temperature a bit better next time, and work on reacting it with sodium acetate later.*
it really does'nt matter you get some so3 kicked off but it's not significant if one is concerned he could add slight excess of nas2o7 to compensate this is crude guerilla heroin chemistry

simply mix them in blender or coffe grinder can't get easier than this swij and swi2bfrank stay nodding from dipropanoyl morphine and for like days on end it lasts an awlfully long time.
definitely worth trying although it's very easy to overdo it and find oneself smaking into things and passing out while ambulatory.
« Last Edit: October 06, 2009, 07:30:48 AM by jon »

Vesp

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Re: propionic anhydride
« Reply #14 on: October 07, 2009, 12:47:59 AM »
Well, my interests are purely for the production of acid anhydrides.

Benzoic anhydride could likely be made this way as well.
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jon

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Re: propionic anhydride
« Reply #15 on: October 31, 2009, 05:35:36 AM »
just about any anhydride can be made this way handily i might add a real breakthrough for the home chemist.

Wizard X

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Re: propionic anhydride
« Reply #16 on: October 31, 2009, 11:55:13 PM »
n-CAPROIC ANHYDRIDE http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0164

n-Caproic anhydride has been prepared by heating caproic acid with acetic anhydride,[3] by heating sodium caproate and acetic anhydride in a sealed tube,[4] by the action of phosphorus oxychloride on barium caproate,[5] by the action of acetyl chloride on caproic acid,[6] and by treating a mixture of sodium caproate and sulfur with chlorine.[7] The method used in the present synthesis was first described by Hurd and Dull.[8]

Propionic anhydride, can be prepared via the same methods stated above with propionic acid.
Albert Einstein - "Great ideas often receive violent opposition from mediocre minds."

jon

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Re: propionic anhydride
« Reply #17 on: November 02, 2009, 11:00:03 PM »
is that wizard x of old from the hive?

Wizard X

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Re: propionic anhydride
« Reply #18 on: November 03, 2009, 02:56:38 AM »
is that wizard x of old from the hive?

YES!
Albert Einstein - "Great ideas often receive violent opposition from mediocre minds."

jon

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Re: propionic anhydride
« Reply #19 on: November 04, 2009, 09:49:23 AM »
what's up man old handle there was spisshak.
odd nickname ayye?