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Author: Subject: succinic acid from tartaric
menchaca
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succinic acid from tartaric

well... i think i´ll need your help again is there a way to get succinic acid from tartaric?.....else were can i get it?
thanks!!!
K9
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Well if you really want to make it......

"Tartaric acid may be reduced to succinic acid by saturating its concentrated aqueous solution with, hydriodic acid, sealing in a strong glass tube, and heating it for 6 or 8 hours, not to exceed the temperature of 120° C. (248° F.). " and that's from here

[Edited on 4-11-2003 by K9]
I am a fish
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Succinic acid is available from both alternative photographic suppliers and brewing/winemaking suppliers.

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Marvin
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Its a tad expensive anywhere Ive found it sold and reducing both hydroxy groups with hydroiodic acid is rather more OTT than OTC.

It can however be prepaired from malic acid, which is tartaric without one of the OH's. This is much cheeper, and sold in larger quantity. The process, from a rather old book is as follows, neutralise the malic acid with chalk and ferment the calcium malate for 3 days with yeast. Add dilute sulphuric acid to the crude calcium succinate produced, and crystalise the acid from the liquid.

I suspect if this is going to be made to work it needs to be trialed a few times. I'm at the stage of trying to find a cheap a source of malic acid locally.

For those interested, I want to make fulgides.
menchaca
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well i´ve got two new questions(yes again..)first is possible use HCl insyead of HI? the second is: I´ve read that is possible to get it from "fermentation"of ammonium tartrate. Somebody knows what in the hell mean with fermentation? i don´t it´s produced as wine..may be descomposition or so...
menchaca
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oh i forgot i wanted it to prepare succinaldehide.. if somebody knows a rute to prepare it directly from tartaric..well that would a great help
thanks!!
Mumbles
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Fermentation of wine, better yet sugar, is still a decomposition. Sucrose into EtOH, Carbon Dioxide, and Water I believe.

The same thing does not happen with the Calcium Malate. It is basically rearranged and gains an Oxygen. I am assuming this from the molecular structures I found. I don't know if this is a fermentation persay though from what I've learned. I've always thought fermentation was the breaking down of carbohydrates into alcohols. It does produce another Hydroxyl group so it very well could be technically.

I highly doubt that HCl could replace HI in that reaction. I can't really explain why, but I think the reaction is driven by the I- ion. I very well could be wrong. If you decide to go that route, make the HI. It's a fairly closely watched chem from what I understand. It's used in illegal Meth manufacture. Theres a proceedure on Rhodium's site for it. The KI/Phosphoric Acid proceedure seems the least difficult/expensive of them all.
Marvin
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Fermentation is just yeasts method of getting the energy it needs. To do this it makes a bunch of enzymes that do interesting things, break down starches, sugars etc. We can abuse this to produce certain chemicals, ethanol, glycerol, butyric acid, lactic acid, succinic acid and others. Its not good to generalise as to what fermentation is, becuase most of these transformations are done by different enzmes.

Tartaric acid is basically, well, think ethylene glycol with a carboxylic acid group stuck to both sides. Remove one OH group and youve got malic acid, remove both of them and youve got succinic acid. Fermentaion will remove the OH from malic acid, wasnt sure if it would remove it from tartaric acid but the calcium salt method wouldnt of worked becuase its barely soluable. Fermentation of the ammonium salt of tartaric acid may well be the way to go, do you have any more info on this? Where is the idea from?

Heres where things get less hopeful, I wouldnt want to be the one trying to make succinaldehyde from succinic acid. Maybe the usual pyrolysis with a formate salt will work, but it looks worrying.

A note on the hive suggests refluxing pyrrole with hydroxlyamine with KOH.

Tricky. Can you think of a way round your problem that doesnt require succinaldehyde?
menchaca
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i haven´t find more information about ammonium tartrate fermetation, this was just a short mention in an old chemistry book from university´s library . in that one also i found that succinaldehyde was obtained from succinis acid again it was just a short mention i´ll try to take the book an write it here but it won´t be very useful anywere
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HCl won't work. The iodide is oxidised to iodine.
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succinic acid - and more!

I found this in an old reference (Thomas Graham, Elements of Chemistry, Including the Applications of the Sciences in the Arts, 1843 [1]). It sounds like a tedious but accessible way to prepare succinic acid.
 Quote: When stearic acid is heated with an equal volume of nitric acid of density 1.284, an abundant disengagement of deutoxide and peroxide of nitrogen takes place as soon as the mixture boils. If the mixture is then allowed to cool the stearic acid separates apparently unaltered, but really converted entirely into margaric acid, while the nitric acid contains no foreign substances in determinable quantity. By the prolonged action of the boiling acid on margaric acid, the latter is gradually but completely dissolved, and the more readily if the nitric acid be renewed from time to time; the solution then contains suberic acid, succinic acid, and an oily substance soluble in nitric acid (Bromeis). Suberic acid: ... It is prepared by evaporating the solution of stearic or margaric acid in nitric acid to one half and allowing it to rest; the solution in 24 hours becomes a semi-solid mass, which is thrown into a funnel to drain, and washed with cold water. When expressed and crystallized several times it forms pure suberic acid. [...] Succinic acid: This acid has long been derived by the distillation of amber (page 614) and exists according to several observers in the resin of some Coniferae. The mother liquor which remains after the separation of suberic acid in the process described above, contains succinic acid soiled with suberic acid. The solution with the washings of the suberic is evaporated to crystallization, the product dried and treated with ether in the cold, which easily dissolves suberic acid while it leaves the succinic acid behind in great measure. The latter may be purified completely by sublimation.

[1]This book was actually acquired by a curious incident. I bought it from a bookseller I found through Alibris. The book was listed as Fowne's (sp?) manual of chemistry that Marvin mentioned a bit ago. I thought I had the right book when it first arrived, because I started reading the contents before looking at the title page (the cover is illegible). It had a preparation of dimethyl sulfate from methanol and excess H2SO4 (8 to 10 parts of acid to methanol), just like Fownes, and also had the nifty KCN + tartaric acid trick to produce aq. HCN (potassium hydrogen tartrate precipitating). After a week I looked at the title page and realized that it wasn't by Fownes at all! Did mid-19th century chemistry authors frequently crib from each others' works? Of course, I suppose modern chemistry textbooks share a lot of content too.

One thing I find interesting is that the language in this book is considerably further from modern terminology than even Muspratt's great encyclopedia, and his encyclopedia was created less than 20 years later. It was considerably harder to understand for this reason. One thing I find odd/interesting about this and other 19th century books is which empirical formulas they got right and which they got wrong. Why, for example, was water so long represented as HO instead of H<sub>2</sub>O? I bet somebody has already written an excellent review article about this aspect of the history of chemistry, but I have yet to read it

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