2bfrank, a relation, has asked me to share his latest endevours. HIS WORDS< NOT MINE>

Ive been giving this lots of thought, had it down on paper, the mechanism (see attached). Its a common mechanism for numerous reactions, but applying it to an anhydride formation, one is left with water acting as a potential nucleophile, and thus regenerating the starting reagent - the alkanoic, but if the water is forming an azetrope with toluene, and being much denser, then it will sink in a DS trap, and not bother the formed addition product. That was my thinking, and Ive put it to the test, and last count, 3 hours into the reaction, Ive got 5.5 ml of H2O at the bottom of the DS trap. The reagents i used were of course a legal alkanoic acid - 100ml, definitely not ACETIC  along with 20 ml of dry toluene, and initially, I added to the pot at one time, all reagents, which included 1 ml of 33% HCl. The DS trap filled quickly(water wise) and I later added another ml of acid, and in future I will wait for the reaction to reach a steady state then add the acid catalyst. Initially I had it on flat out reflux, and flat out stirring. An hour ago, 3 hours into the reaction, the stir bar got jammed, and I had to slowly start it up, and decided to watch the effect of just a mild stir, but still refluxing away strongly, and I could literally see water hitting the top of the DS trap, and sinking to the bottom, so mild stirring has been maintained, and Im going to check her now. The amount now is 6.2 ml of water, This is not alot, but its over 4 ml, and personally, for such a handy reagent, I dont mind baby sitting, for a day, Just keeping the water cool for the condenser, and if the DS gets totally full of water, ending things, or changing things in order to continue. The expected amount can easily be worked out (half the molar amount of alkanoic used), so anyway, to me having water other than from the 2ml of catalyst, is success, and the reaction itself could be improved, Perhaps more toluene could be advantageous.  This is somewhat new for me, working on a mechanism and adapting it to something that I hadn't seen before, and its this sort of chem that I really enjoy. Anyway, I hope to GOD this isn't a common method, and Im the dumbass reinventing the wheel, but hey, if thats the case, the intention was to share something that i feel has merit, and is worthy of more experimentation,  - peace out. Last check, the pot is now a mild beige color, and water is 7.2 ml.  .  Ill keep on till I get the expected, and then check, but this is looking indeed promising. PEACE OUT.

I just checked, its up to 9 ml, my expected amount for 100ml of alkanoic, is 15.72grams, and being water, then its mls. Im blown away by this.

So far, and Im doing small scale, Ive gotten 5 ml - which is a small amount to test bp ect. ITs over 120 C, I know that, but Ill scale up, when and if I think this is a potential. So.not as promising as I thought it might be. Ive thought some more, as the night I rattled this out, I was having a late long night - one could say, well, the chloride could behave as a nucleophile, which is something I tend to also experiment with, but looking at changing over to another H30 source and we shall see. Ill shut up about this, until ive got results, either way. Peace out.

I need constant temp control. Water bath might do it, and use stirring to explore that effect on its own. Its protonation first, which makes the nucleophilic attack attractive to remove the charged carbonyl, So its all in the flask. Slowly nutting this out. Id be so stoked to work this one, as it would apply to any single carboxylic acid. Hope its cool me writing this out here. I dont give a fuck, no ones responding. Just got the rambles. and if its good, then its here. If its not, Ill delete. 2b

Thanks for saying that dreamOn, The water wasn't generating enough heat, so I switched to an oil bath, and on a low setting, with very slow stirring, the water was seen to consistently sink in the trap. When I collect the expected 34 ml, I might even reflux with a good drying salt for 30 minutes, just to be absolutely sure that its dry of water, which is the enemy in this situation. I'll fractionally distill the product with a short column, as the bp of 118 and 138, is close. I may in fact have to add some toluene to form an acetrope with any remaining acetic acid and tolune. bp. is 105, which is a bigger gap from the anhydride. Fun and games.