Oxidation of 5-(hydroxymethyl) furfural to 2,5 diformylfuran and subsequent decarbonylation to unsubstituted furan
AssigneeE. I. Du Pont de Nemours and Company
InventorsVladimir Grushin, WALTER PARTENHEIMER, LEO E. MANZER
Life of this patent
Estimating the term…
Abstract
Alcohols are catalytically oxidized to aldehydes, in particular to benzaldehyde and diformylfuran, which are useful as intermediates for a multiplicity of purposes. The invention also relates to the polymerization of the dialdehyde and to the decarbonylation of the dialdehyde to furan.
Claims28
A process for the preparation of a diacid of the formula HOOC—R′—COOH from an alcohol/aldehyde of the formula HOH2C—R′—(C═O)H, wherein R′ is an optionally substituted furan ring, comprising the steps:
- (a) contacting the alcohol/aldehyde with an oxidant in the presence of a metal bromide catalyst forming an alcohol/acid having the formula HOH2C—R′—COOH, and optionally isolating the alcohol/acid;
- (b) contacting the alcohol/acid with an oxidant in the presence of a metal bromide catalyst forming an acid/aldehyde having the formula HOOC—R′—(C═O)H, and optionally isolating the acid/aldehyde;
- (c) contacting the acid/aldehyde with an oxidant in the presence of a metal bromide catalyst forming the diacid, optionally isolating the diacid.
A process for the preparation of a diacid of the formula HOOC—R′—COOH from an alcohol/aldehyde of the formula HOH2C—R′—(C═O)H, wherein R″ is an optionally substituted furan ring, comprising the steps:
- (a) contacting the alcohol/aldehyde with an oxidant in the presence of a metal bromide catalyst forming a dialdehyde having the formula H(C═O)—R′—(C═O)H, and optionally isolating the dialdehyde;
- (b) contacting the dialdehyde with an oxidant in the presence of a metal bromide catalyst forming an acid/aldehyde having the formula HOOC—R′—(C═O)H, and optionally isolating the acid/aldehyde;
- and
- (c) contacting the acid/dialdehyde with an oxidant in the presence of a metal bromide catalyst forming the diacid, and optionally isolating the diacid.
A process for the preparation of an aldehyde comprising:
- contacting a compound of the formula AR—CH2—OH wherein AR is an optionally substituted aryl with an oxidant in the presence of a metal bromide catalyst.
A process to form a polyester polymer comprising the repeat units A, B and C
- wherein said process comprises polymerization of diformylfuran.
A polyester polymer comprising repeating units A and B and C.
A process for the preparation of furan comprising converting 2,5-diformylfuran into a furan and furfural product mix via decarbonylation in the presence of a catalytic amount of a compound consisting essentially of a optionally supported metal selected from Periodic Group VIII.
Dependencies are inferred from the claim text.