`
`Exhibit 2012
`E.I. du Pont de Nemours & Co. and
`Acher-Daniels-Midland Co. v. Furanix Technologies BV
`IPR2015-01838
`
`
`
`Study of the influence of
`Co/ Mn ratio
`
`o
`
`0
`
`/
`
`R0
`
`\
`
`/
`
`C0/1VIn/Br
`
`
`ACOH, 180 °C
`Air
`
`E
`
`.'_\\/AETIIJKI
`
`O
`
`O
`
`R= H, Me or Et
`
`Fixed Conditions:
`
`- Pressure: 20 bar.
`
`- Catalyst loading: 4 mol % (Co+Mn)
`
`- Solvent: Acetic acid.
`
`— Temperature:180 °C
`
`- Reaction time: 60 minutes.
`
`- Br/(Co+Mn): 0.7.
`
`Variables:
`
`— Co/Mn ratios (1/0; 80/1; 60/1; 40/1; 20/1; 10/1; 4/1;
`
`\
`
`3/2; 2/3; and 1/4).
`
`Confidenfial
`
`2
`
`
`
`Study of the influence of
`Co/ Mn ratio
`
`§)
`
`1_\\/AETIIJKI
`
`sDicarboxy|ics vs Co/Mn ratio
`
`sCarboxy|ic_(%)
`
`0
`
`02
`
`0.4
`
`one
`
`0.8
`
`1
`
`1.2
`
`Co/Mn
`
`Confidenfial
`
`
`
`3
`
`
`
`Study of the influence of
`Co/ Mn ratio
`
`§,
`
`x_\\/AETIIJKI
`
`S
`
`Dicarboxylics vs Mn/Co ratio
`
`80-
`
`70-
`
`60-
`
`50-
`
`40*
`
`sCarboxy|ic_(%)
`
`1)
`
`0.2
`
`0.4
`
`0.6
`
`0.8
`
`1
`
`1.2
`
`1.4
`
`1.6
`
`Mn/Co
`
`Confidenfial
`
`
`
`4
`
`
`
`Study of the influence of
`Co/ Mn ratio
`
`§»
`
`.'_\\/AETIIJKI
`
`Conclusions:
`
`Both Cobalt and Manganese must be present in the
`
`catalytic solution in order
`
`to get a good performance
`
`Confidential
`
`
`
`5
`
`5
`
`
`
`§)
`.'_\\/AETIIJKI
`O
`
`O
`
`\
`
`/
`
`oH
`
`Use of g\MF/HMF as substrate
`0
`/
`
`O
`
`HO
`
`m
`
`\
`
`/
`
`O
`
`Co/Mn/Br
`
`
`0
`O
`/
`kom
`
`Fixed Conditions:
`
`- Pressure: 20 bar.
`
`Acolikl80 OC
`
`- Catalyst loading: 5.4 mol % (Co+Mn)
`
`- Solvent: Acetic acid.
`
`- Temperature:180 °C
`
`- Reaction time: 60 minutes.
`
`- Co/Mn ratio: 1.
`
`- Br/(Co+Mn): 0.7.
`
`
`
`- Br/(Co+Mn): 1.0; 0.7; 0.4 and 0.1
`
`_ substrate: HMF, HMF/AMF(3/2), HMF/AMF (2/3) and AMF
`
`Confidential
`
`
`
`
`
`6
`
`6
`
`
`
`Use of AMF/HMF as substrate
`
`80-
`
`75-
`
`70-
`
`55-
`
`50-
`
`sFDCA_(%)
`
`I
`
`I
`
`§,
`
`.'_\\/AETIIJKI
`
`I HMF
`I HMF/AMF (3/2)
`I HMF/AMF (2/3)
`-AMF
`
`Scatler Plot
`
`I
`
`I
`
`I
`
`I
`
`I
`
`'
`I
`
`I
`
`0.2
`
`0.4
`
`0.6
`
`0.8
`
`Br/(Co+Mn)
`
`Confidenfial
`
`
`
`7