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Topic: Lactic acid from Glucose.  (Read 6702 times)

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Offline Alberto_Kravina

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Lactic acid from Glucose.
« on: March 12, 2006, 04:37:24 AM »
Does somebody of you know the exact reaction mechanism of the reaction of a glucose molecule to two lactic acid molecules? C6H12O6 --> 2 C3H6O3
I think that it's a redox-disproportionation (oxidoreduction), since a methyl group is formed, and there are no carbon atoms with the ox-num +3 in the Glucose molecule as well as there aren't any carbon atoms with ox-num. +3 (carboxilic acid) in the Glucose molecule.. :(

Thanks for any advice :)


Offline HP

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Re:Lactic acid from Glucose.
« Reply #1 on: March 12, 2006, 05:47:31 AM »
Glucose is transformed enzymetically to Pyruvic acid(CH3COCOOH) by the biochemical process called "Glycolysis". The formed pyruvic acid(pyruvate) is reduced in muscules by NADH into the enzyme lactatedehydrogenaze to lactic acid:
C3H4O3 + NADH + H+ ? CO2 + C2H5OH + NAD+
Chemically at lab you may obtain pyruvic acid by thermal pyrolysis of tartaric acid and then you may reduce it to lactic acid by using many reducing agents. Its interesting what such could be proposed :)
xpp

Offline AWK

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AWK

Offline HP

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Re:Lactic acid from Glucose.
« Reply #3 on: March 13, 2006, 11:48:46 AM »
Nice ilustration AWK! Thats what i tried shortly to explain ..Also now i see i have made a mistake in the proposed equation as the product of hydrogenation pyruvat should be lactic acid CH3CH(OH)COOH.
I remember i have red from some book that pyruvat could be prepared from acethyl chloride and...i dont remember the other reagent. Do you think it may be formic acid or some of its esters  ???
xpp

Offline AWK

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Re:Lactic acid from Glucose.
« Reply #4 on: March 14, 2006, 04:50:07 AM »
AWK

Offline HP

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Re:Lactic acid from Glucose.
« Reply #5 on: March 14, 2006, 12:10:52 PM »
Cool with KCN  :P and the yeld should be nice too. But do you think there might be some side reactions in alkaline ot acidic hydrolyze step of the formed a-ketonitrile as having mobile H-athoms at CH3 may be some aldol type ???
xpp

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