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Dimethyl oxalate can be converted into ethylene glycol in high yields (94.7%) [10] [11] The methanol formed is recycled in the process of oxidative carbonylation. [12] Other plants with a total annual capacity of more than 1 million tons of ethylene glycol per year are planned. Decarbonylation gives dimethyl carbonate. [13]
Dimethyl carbonate and dimethyl oxalate are produced industrially using carbon monoxide and an oxidant, in effect as a source of CO 2+. [2]+ + + The oxidative carbonylation of methanol is catalyzed by copper(I) salts, which form transient carbonyl complexes.
Oxalate (systematic IUPAC name: ethanedioate) is an anion with the chemical formula C 2 O 2− 4. This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate (Na 2 C 2 O 4), and several esters such as dimethyl oxalate ((CH 3) 2 C 2 O 4). It is a conjugate base of oxalic acid.
In the former route, the additional carbon is supplied by dimethyloxalate, which reacts with the enolate. In other syntheses, pimelic acid is made from cyclohexene-4-carboxylic acid, [5] and a fourth method also exists based on the 1,4 reaction of malonate systems with acrolein. [6] Several patents exist for the production of pimelic acid.
ODAP can be synthesized from L-α,β-diaminopropionic acid and dimethyl oxalate at a pH of 4.5-5. Cupric oxide can be used to temporarily protect the α-NH2 group of the L-α,β-diaminoproprionic acid during the reaction. [2] The pathway for one chemical synthesis of ODAP
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Oxidative carbonylation is a class of reactions that use carbon monoxide in combination with an oxidant to generate esters and carbonate esters.These transformations utilize transition metal complexes as homogeneous catalysts. [1]
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