`
`Exhibit 2013
`E.I. du Pont de Nemours & Co. and
`Acher-Daniels-Midland Co. v. Furanix Technologies BV
`IPR2015-01838
`
`
`
`AMF oxidation.
`
`Patent results vs Our results
`
`0
`
`o/
`
`AcO
`
`\/
`
`Co/Mn/Br
`
`
`HO
`
`ACOH. 180 °C
`
`E
`
`.'_\\/AETIIJKI
`
`O
`
`O
`
`O
`
`\
`
`/
`
`OH
`
`Fixed Conditions:
`
`— Pressure: 30 bar.
`
`- Catalyst loading: 3.5, 5.25 mol % (Co+Mn)
`
`— Solvent: Acetic acid.
`
`— Temperature:180 °C
`
`— Reaction time: 120 minutes.
`
`— Br/(Co+Mn): 1.0
`
`— Co/Mn ratio: 1/1
`
`Confidenfial
`
`
`
`2
`
`
`
`AMF oxidation.
`
`Patent results vs Our results
`
`E
`
`x_\\/AETIIJKI
`
`Scatter Plot
`
`-180 ° c. Cat loading: 5.4 mol °/o
`
`-100 ° c. Cat loading: 5.25 mol %
`
`-100 ° c. Cat loading: 3.5 mol °/0
`
`US2009/0156841 A1:
`
`yFDCA= 54 °/o.
`
`sFDCA_(%)
`
`02
`
`0.4
`
`0.6
`
`0.8
`
`1
`
`BrI(Co+Mn)
`
`Confidenfial
`
`
`
`3
`
`
`
`AMF oxidation.
`Patent results vs Our results
`
`§»
`
`.'_\\/AETIIJKI
`
`Conclusions:
`
`FDCA can be formed from AMF at 100 °C.
`
`The results obtained are much lower than those claimed in the patent,
`
`even using 1.5 times more catalyst.
`
`Confidential
`
`
`
`4
`
`4
`
`
`
`DMF and 5—MF oxidation
`
`§)
`
`.'_\\’A§'I'IIJkI
`
`O
`
`\
`
`/
`
`0
`
`°
`com.
` OH
`Ho
`\
`/
`
`ACOH. 180 °C
`
`ff
`
`A”
`
`Fixed Conditions:
`
`— Pressure: 50 bar.
`
`- Catalyst loading: 5.4 mol % (Co+Mn)
`
`- Solvent: Acetic acid.
`
`— Temperature:180 °C
`
`— Reaction time: 120 minutes.
`
`- Co/Mn ratio: 1/1
`
`Variables:
`
`- Br/(Co+Mn): 1.0, 0.7, 0.4 and 0.1
`
`- Substrate: DMF and 5—MF
`
`Confidential
`
`
`
`5
`
`5
`
`
`
`DMF and 5-MF oxidation
`
`1_\\’A§TII.JKI
`
`I 5-MF
`
`I DMF
`
`sFDcA4%)
`
`02
`
`0.4
`
`0.6
`
`0.8
`
`Br/(Co+Mn)
`
`Confidenfial
`
`
`
`6