Efficient, high-yield conversion of saccharides in a pure or crude form to 5-(chloromethyl)-2-furaldehyde

US9102644B2 · kind B2 · utility

Assignee

• XF Technologies Inc. · US

Inventors

• Peter Mikochik · Groton, US
• Aviad Cahana · Albuquerque, US
• Edward Nikitin · Albuquerque, US
• Jeremy Standiford · Rio Rancho, US
• Kyle Ellis · Albuquerque, US
• Luzheng Zhang · Albuquerque, US
• Timothy George · Albuquerque, US

Key dates

• Filing date: Mar 3, 2014
• Grant date: Aug 11, 2015
• Expiry date: Apr 10, 2034

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D307/50
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention describes methods and apparatuses for the synthesis of 5-(chloromethyl)-2-furaldehyde (CMF) from saccharides in pure or crude form, the method comprising: (a) continuously contacting saccharides in pure or crude form, hydrochloric acid, and an organic solvent, by way of a continuous, biphasic-flow reactor assembly at a temperature from about 60 degrees C. to about 200 degrees C. and pressures from about 1 atmosphere to about 20 atmospheres, such that CMF is produced; (b) separating 5-(chloromethyl)-2-furaldehyde by liquid/liquid and solid/liquid phase separation; (c) producing at least five kilograms per day with at least 50% yield. Embodiments of the present invention can produce CMF in a continuous fashion, with high yield and without degradation of CMF to such side products as 5-(hydroxymethyl)furfural (HMF), 2-(2-hydroxyacetyl)furan (HAF) and levulinic acid (LA).