Production of tri-methyl benzene derivatives
The present invention relates to the production of tri-functional aromatic molecules from diformylfuran, in particular to the production of tri-methyl benzene derivatives such as for example trimellitic acid or 1,2,4-tri(aminomethyl)benzene from diformylfuran and its derivatives.
1. A process for the preparation of a compound of Formula (I)
wherein
X and Y independently are optionally substituted heteroatoms;
each R 2 independently is H, alkyl, alkenyl or aryl;
R 3 and R 4 independently are H or —CN, provided that at least one of R 3 and R 4 is —CN; the process comprising
a.) dehydration/aromatization of a compound of the Formula (II)
wherein
X and Y independently are optionally substituted heteroatoms;
R is a C 1-4 alkylene group which may optionally be substituted with one or more R 1 ;
R 1 is a linear, branched and/or cyclic, saturated or unsaturated hydrocarbon group which optionally bears one or more functional groups;
R 2 independently is H, alkyl, alkenyl or aryl; and
R 3 and R 4 independently are H or —CN, provided that at least one of R 3 and R 4 is —CN;
to obtain a compound of the Formula (III)
wherein X, Y, R, R 2 , R 3 and R 4 are defined as above;
followed by deprotection of the compound of Formula (III);
or
b.) carrying out the dehydration/aromatization and the deprotection of the compound of Formula (II) in a single step.
2. The process according to claim 1 , wherein X and Y are O or X and Y are S.
3. The process according to claim 1 , wherein R is —CH 2 —CH 2 —, CH 2 —CH 2 CH 2 —, —CH(CH 3 )—CH(CH 3 )— or CH 2 —C(CH 3 ) 2 —CH 2 —.
4. The process according to claim 1 , wherein R 2 is H.
5. The process according to claim 1 , wherein X and Y are O and R is —CH 2 —CH 2 —.