`E.I. du Pont de Nemours & Co. and
`Acher-Daniels-Midland Co. v. Furanix Technologies BV
`IPR2015-01838
`
`
`
`Experimental approach
`
`_ Batch reactions (HTHPQCS).
`
`— Air was used as source of O2
`
`— Source of metals:
`
`-Co: Co(AcO)2-4H2O
`
`-Mn: Mn(AcO)2-4H2O
`
`-Br: NaBr
`
`- Acetic acid was used as solvent.
`
`E)
`
`AVA IN T I [J NI
`
`1'
`
`
`
`Amazon [AB - June — 2009
`
`—Confi0’ent/'a/—
`
`2
`
`
`
`A\/4\§'I'IIJNI Effect of the temperature
`Results:
`
`0
`
`O
`
`0
`
`\
`
`/
`
`Decarboxylation
`
`200-220 °c
`
`0
`
`\
`
`/
`
`on
`
`Ho
`
`O
`
`on
`
`2-Furoic acid
`
`2-Furoic acid will act as end-capper in the polycondensation lowering the
`
`final molecular weight
`
`0
`
`O
`
`O
`
`O
`
`MeO
`
`\
`
`/
`
`+ HOQflW Tb rv\AAr\/vvx./vvx.0
`0Me
`
`\
`
`/ o
`
`\
`
`/
`
`0Me+ H°'m~'WUWW‘~ j’ \
`
`/
`
`0
`
`Amazon MB - June — 2009
`
`—Confident7'a/—
`
`3
`
`
`
`A\/A\§'I'IIJNI
`
`K)
`
`Meo
`
`\
`
`/
`
`oH
`
`HO
`
`\
`
`/
`
`oH _220 cc
`
`Co/Mn/Br
`
`P= 60 bar
`
`Cat Ioading= 0.78 %
`
`Pure FDCA
`
`Mixture FDCAI FDCA1l2Me (45/55)
`
`I FDCA inau (93)
`
`
`
`cu FDCA1l2Me final (ea)
`
`El Mass balance (96)
`
`100
`
`90
`
`80
`
`7o
`
`60
`
`50
`
`40
`
`30
`
`20
`
`I FDCA final (96)
`
`
`
`1“)
`
`90
`
`30
`
`70
`
`60
`
`50
`
`40
`
`30
`
`20
`
`10
`
`O
`
`No Catalyst
`
`1_5_20
`
`No catalyst
`
`1-5-20
`
`cahlsyt composition
`
`catalyst composition
`
`Amazon MB - June — 2009
`
`—Confident7'a/—
`
`4
`
`
`
`Results:
`
`
`
`Stability of products. 160 °C and 60 & 20 b
`
`
`
`A\/AETIIJNI
`
`71 %
`
`29 %
`
`CoIMnIBr
`
`
`AcOH
`
`T=160 °C
`
`Cat Ioading= 0.78 %
`
`Pressure: 20 bar.
`
`Pressure: 60 bar.
`
`Water was added to
`
`these samples
`
`
`
`I FDCA final (%)
`
`I FDCA1/2Me final (%)
`
`I Mass balance (%)
`
`115
`
`110
`
`105
`
`100
`
`95
`
`90
`
`85
`
`80
`
`115
`
`110
`
`Water was added to
`
`these samples
`
`
`
`105
`
`|:I Mass balance (%)
` 100
`
`El FDCA final (%)
`
`I FDCA1/2Me final (%)
`
`
`
`95
`
`90
`
`85
`
`80
`
`None
`
`1-5-5
`
`1-5-20
`
`1—5—5
`
`1-5-20
`
`None
`
`1—5—5
`
`1-5-20
`
`1—5—5
`
`1-5-20
`
`Catalyd composition
`
`Catalyst composition
`
`Note: 2-Furoic acid was not present in any of the samples treated at 160 °C
`
`Amazon MB - June — 2009
`
`—Confident7'a/—
`
`5
`
`
`
`Conclusions
`
`R
`
`AVA § 1' I IJ NI
`
`— The optimum temperature seems to be in the range of 160-180 °C
`
`At higher temperatures (200 and 220 °C) 2-furoic acid appeared.
`
`- The final products are quite instable at high temperatures (200
`
`-220 °C). In the other hand the dicarboxylic compounds seem to
`
`be quite stable at 160 °C
`
`- There were no differences regarding the reaction time and just
`
`after 30 minutes the reaction is finished.
`
`Amazon MB - June — 2009
`
`—Conf/'a’ent7'a/—
`
`6
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