`
`Exhibit 2016
`E.I. du Pont de Nemours & Co. and
`Acher-Daniels-Midland Co. v. Furanix Technologies BV
`IPR2015-01838
`
`
`
`Block 1
`Eental REMARK:
`: IZMAYO9
`Date weighing, dissolving and adding Cat and substrate
`: l21\‘IAY09
`Date starting reaction of experiment
`Date weighing, dissolving and adding Saecharine stock solution : IZMAYO9
`Date of analyzing with the HPLC
`: l31\‘IAY09 by Paul
`HPLC—anal_vzing according HPLC—6 logboek
`'
`
`Block 2 and 3
`ISJUN09
`l5JUN09
`ISJUN09
`l5JUN09
`
`Experimental
`Done by ABE:
`Load blocks according table] till 16. Weighing tolerance‘
`Add stirring magnet.
`Close with teflon/rubber cap.
`Bringunderpressurewith lI:ill60BaratRT
`Placed in preheated HTHP QCS of 180 °C according settings in table 2, during 1 hours.
`Placed immediately after the reaction time in an ice bath during 35 minutes.
`Open and thereby decompress reactors.
`Add 1.0 ml ofD1\ISO. Stirring for 20 minutes
`Add 5.0 ml of Saccharine stock solution, table 5.
`These dilutions where stirred for 10 minutes.
`These dilutions to 7 times were transferred to 8 ml vials. Stirring during a whole night
`Done by CMD:
`
`Dilutionsto700timesweremadeby l0plofdfl1rfions8finies+990plofWateFmHPLCviak_
`
`Table 5: Saccharine stock solution 11.04 -
`
`-
`
`'ml
`
`2.2080
`
`200.0
`11.04
`l5ma 0'
`090512—OxE—073—V0l till
`V09
`
`1.1043+0.2206
`
`l00+20
`
`l5jun09
`090615-0xE-073-V09 an
`we +
`B1—FDCA—l0 and —5mg
`
`
`Bl-FDCAhal£Et-10 and —5mv
`mcAs
`
`Table 6: Blancs solutions
`
`B'==-ks
`FDCA1/2Me 10 mm
`mom/2Mes
`memo m
`
`Table 10: List of catal
`
`ts.
`
`flfl 0-<°~»4H2°
`
`Mn<°Ar>~H=° J
`
`2
`
`
`
`1
`
`‘ul:
`
`EL:
`
`.'
`
`.
`
`'‘‘«l:. 11:
`
`‘
`
`I‘
`
`.
`
`"
`
`‘T
`
`3
`
`
`
`HPLC
`name
`
`OxE073-V1
`OxE073-V2
`---
`OxE073-V4
`OxE073-V5
`OxE073-V6
`OxE073-V7
`OxE073-V8
`
`
`
`
`
`HPLC
`name
`
`
`OxE073-V9
`
`OxE073-V10
`OxE073-V11
`OxE073-V12
`OxE073-V13
`OxE073-V14
`OxE073-V15
`OxE073-V16
`OxE073-V17
`OxE073-V18
`
`
`
`
`
`HPLC
`name
`
`
`OxE073-V19
`
`OxE073-V20
`OxE073-V21
`OxE073-V22
`OxE073-V23
`OxE073-V24
`OxE073-V25
`OxE073-V26
`OxE073-V27
`OxE073-V28
`
`
`
`Table 11: Block 1 /Temp = 220 C / P= 60 bar (Air) / T0=14.27
`
`R
`Nr.
`
`1
`2
`3
`4
`5
`6
`7
`8
`
`
`
`
`
`Substrate
`
`Cat Code
`
`V AcOH
`
`
`49.9
`49.9
`---
`49.8
`50.7
`50.7
`46.9
`50.3
`
`
`
`
`
`
`---
`---
`---
`---
`Co/Mn/Br-15
`Co/Mn/Br-15
`Co/Mn/Br-15
`Co/Mn/Br-15
`
`
`
`
`
`
`
`
`
`[ml]
`1.0
`1.0
`---
`1.0
`---
`---
`---
`---
`
`
`
`
`
`Substrate
`name
`
`FDCA
`FDCA
`FDCA1/2Me
`FDCA1/2Me
`FDCA
`FDCA
`FDCA1/2Me
`FDCA1/2Me
`
`
`
`
`
`Time 1 hours
`
`Cat
`concentration
`[mol %]
`---
`---
`---
`---
`
`
`
`
`
`
`
`
`
`VCat
`
`[ml]
`---
`---
`---
`---
`1.0
`1.0
`1.0
`1.0
`
`
`
`
`
`Substrate
`
`Cat Code
`
`V AcOH
`
`VCat
`
`Water added
`
`
`Table 11: Block 2 /Temp = 180 C / P= 60 bar (Air) / T0=12.0 Time 1 hours
`R
`Substrate
`Nr.
`name
`
`
`
`
`
`1
`
`2
`3
`4
`5
`6
`7
`8
`9
`10
`
`
`
`
`
`FDCA1/2Me
`
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`
`
`
`
`
`64.7
`64.5
`64.8
`64.6
`64.5
`65.9
`64.3
`64.5
`63.6
`64.1
`
`
`
`
`None
`None
`Co/Mn/Br 01
`Co/Mn/Br 01
`Co/Mn/Br 09
`Co/Mn/Br 09
`Co/Mn/Br 01
`Co/Mn/Br 01
`Co/Mn/Br 09
`Co/Mn/Br 09
`
`
`
`
`
`[ml]
`
`[ml]
`
`1.5
`1.5
`0.5
`0.5
`0.5
`0.5
`0.5
`0.5
`0.5
`0.5
`
`
`
`0
`
`0
`1.0
`1.0
`1.0
`1.0
`1.0
`1.0
`1.0
`1.0
`
`
`
`
`
`[µL]
`
`---
`
`---
`---
`---
`---
`---
`20
`20
`20
`20
`
`
`
`Solvent
`
`
`AcOH
`AcOH
`---
`AcOH
`AcOH
`AcOH
`AcOH
`AcOH
`
`
`
`
`
`Solvent
`
`
`
`AcOH
`
`AcOH
`AcOH
`AcOH
`AcOH
`AcOH
`AcOH
`AcOH
`AcOH
`AcOH
`
`
`
`
`
`
`Table 11: Block 2 /Temp = 180 C / P= 20 bar (Air) / T0=12.00 Time 1 hours
`
`
`Substrate
`
`Cat Code
`
`V AcOH
`
`VCat
`
`Water added
`
`Solvent
`
`
`
`64.8
`63.9
`64.2
`63.9
`64.1
`64.0
`64.4
`63.8
`65.0
`64.1
`
`
`
`
`None
`None
`Co/Mn/Br 01
`Co/Mn/Br 01
`Co/Mn/Br 09
`Co/Mn/Br 09
`Co/Mn/Br 01
`Co/Mn/Br 01
`Co/Mn/Br 09
`Co/Mn/Br 09
`
`
`
`
`[ml]
`
`[ml]
`
`[µL]
`
`0.5
`0.5
`0.5
`0.5
`0.5
`0.5
`0.5
`0.5
`0.5
`0.5
`
`
`
`1.0
`
`1.0
`1.0
`1.0
`1.0
`1.0
`1.0
`1.0
`1.0
`1.0
`
`
`
`---
`
`---
`---
`---
`---
`---
`20
`20
`20
`20
`
`
`
`
`
`AcOH
`
`AcOH
`AcOH
`AcOH
`AcOH
`AcOH
`AcOH
`AcOH
`AcOH
`AcOH
`
`
`
`R
`Nr.
`
`
`Substrate
`name
`
`
`FDCA1/2Me
`
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`FDCA1/2Me
`
`
`
`1
`
`2
`3
`4
`5
`6
`7
`8
`
`
`
`
`
`
`
`4