ChemicalBook CAS DataBase List 1,3-Acetonedicarboxylic acid

1,3-Acetonedicarboxylic acid synthesis

8synthesis methods

Product Name:1,3-Acetonedicarboxylic acid
CAS Number:542-05-2
Molecular formula:C5H6O5
Molecular Weight:146.1

Acetonedicarboxylic acid is produced from citric acid [77-92-9] by many industrial processes that differ only slightly. Citric acid is treated with oleum and reacts to yield acetonedicarboxylic acid via decarbonylation and dehydration.
Other possible production methods include reaction of acetone with carbon dioxide, oxidation of citric acid with chlorosulfuric acid, or reaction of ketene with phosgene.

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Yield:542-05-2 98.2%

Reaction Conditions:

Stage #1: 2-methoxypropane-1,3-dicarboxylic acidwith sodium nitrate;lead(IV) tetraacetate at 36; for 2.5 h;
Stage #2: with zinc(II) oxalate at 36; for 2 h;Temperature;

Steps:

3

A: 3 mol of 2-methoxypropane-1,3-dicarboxylic acid was added to the reaction vessel, and 900 ml of a 22% by mass sodium nitrate solution was added.Raise the solution temperature to 36 ° C, add 8 mol of lead tetraacetate in 4 times in 40 min.Controlling the stirring speed of 170 rpm, and continuing the reaction for 110 min; B: Then add 8 mol of zinc oxalate powder, continue the reaction for 2 h, and lower the temperature to 22 ° C.Adding a mass fraction of 16% potassium chloride solution for 30 min, adding a mass fraction of 47% diphenyl ether solution for 60 min,Recrystallized in a 65% diethylene glycol solution, dehydrated with anhydrous calcium sulfate dehydrating agent,The finished acetone dicarboxylic acid was 430.116 g, and the yield was 98.2%.

References:

CN108238929,2018,A Location in patent:Paragraph 0011; 0014-0017; 0018-0021; 0022-0025

77-92-9 Synthesis