Method for the production of aldehydes and ketones by oxidizing primary and secondary alcohols with alkylphosphonic acid anhydrides

US7262328B1 · kind B1 · utility

Assignee

• Archimica, Inc. · US

Inventors

• Andreas Meudt · Hofheim, DE
• Stefan Scherer · Büttelborn, DE
• Claudius Boehm · Frankfurt, DE

Key dates

• Filing date: Apr 18, 2005
• Grant date: Aug 28, 2007
• Expiry date: Apr 18, 2025

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C269/06
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The invention relates to a method for the production of a.) aldehydes of formula (II): R1—CHO and b.) aldehydes of formula (III): R1—C(O)—R2 by reacting a.) primary alcohols (R1CH2—OH) or b.) secondary alcohols (R1—CH(OH)—R2) with cyclic phosphonic acid anhydrides in the presence of dialkyl-, diaryl- and/or alkyl-aryl sulphonic oxides at a temperature in the region of between −100 to +120° C., whereby R1 and/or R2 represent H, a substituted linear or branched C1-C12-alkyl radical, a substituted C3-C10 cycloalkyl-, alkenyl-, aryl- or heteroaryl radical. A cyclic phosphonic acid anhydride is used, preferably, as a 2,4,6-substituted 1,3,5,2,4,6-trioxatriphosphinane of formula (I), wherein R′ independently represents allyl, aryl or open-chained or branched C1-C12-alkyl-radicals. Optionally, the reaction can be carried out in the presence of a tertiary amine base NR53