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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]
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.
The by-products are dimethyl sulfide ((CH 3) 2 S), carbon monoxide (CO), carbon dioxide (CO 2) and—when triethylamine is used as base—triethylammonium chloride (Et 3 NHCl). Of the volatile by-products, dimethyl sulfide has a strong, pervasive odour and carbon monoxide is acutely toxic, so the reaction and the work-up needs to be performed ...
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]
Transition metal oxalate complexes are coordination complexes with oxalate (C 2 O 4 2−) ligands. Some are useful commercially, but the topic has attracted regular scholarly scrutiny. Oxalate (C 2 O 4 2-) is a kind of dicarboxylate ligand. [1] As a small, symmetrical dinegative ion, oxalate commonly forms five-membered MO 2 C 2 chelate rings.
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The reaction is particularly suitable for the synthesis of aldehydes from primary alcohols. Analogously, secondary alcohols can be oxidized to form ketones. Dimethyl sulfoxide/acetic anhydride serves as oxidizing agent. Albright-Goldman-Oxidation (Aldehyd) The reaction does not proceed further to the carboxylic acid.
The Seyferth–Gilbert homologation is a chemical reaction of an aryl ketone 1 (or aldehyde) with dimethyl (diazomethyl)phosphonate 2 and potassium tert-butoxide to give substituted alkynes 3. [1] [2] Dimethyl (diazomethyl)phosphonate 2 is often called the Seyferth–Gilbert reagent. [3] The Seyferth–Gilbert homologation