UNITED STATES PATENT AND TRADEMARK OFFICE
`_________________________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`_________________________
`
`E. I. DU PONT DE NEMOURS AND COMPANY and
`ARCHER-DANIELS-MIDLAND COMPANY,
`Petitioners,
`
`v.
`
`FURANIX TECHNOLOGIES B.V.,
`Patent Owner
`_________________________
`
`Case IPR2015-01838
`Patent 8,865,921
`_________________________
`
`RESPONSE OF PATENT OWNER FURANIX TECHNOLOGIES B.V.
`
`

`
`TABLE OF CONTENTS
`
`Page
`
`I. TECHNICAL BACKGROUND AND SUMMARY OF ARGUMENT ......... .. 1
`
`II. The ‘921 Patent, Prosecution History and Claims Construction ...................... .. 9
`
`A. The ‘921 Patent’s Specification and Claims .................................................. .. 9
`
`B. Prosecution History of the ‘921 Patent ........................................................ .. 11
`
`C.
`
`“Construction” of the Claims in the ‘921 Patent ......................................... .. 12
`
`III. ARGUMENT — PATENTABILITY SHOULD BE AFFIRMED ............... .. 14
`
`A. A Person of Ordinary Skill in the Art .......................................................... .. 15
`
`B. The Asserted Prior Art and Its Differences from the Claims at Issue ......... .. 16
`
`1. WO 01/72732 (“the ’732 Publication, Ex. 1002) ...................................... .. 16
`
`2. RU 448177 (“RU ’l77,” EX. 1007) ............................................................. .. 22
`3. US 2008/0103318 (“the ’3l8 Publication,” Ex. 1008) .................................. 23
`
`4. Lewkowski (Ex. 1005) ............................................................................... .f.. 25
`
`5. Oae (EX. 1006) ........................................................................................... .. 26_5_
`
`6. Admitted Prior Art ..................................................................................... .. 27g
`
`7. Parenheimer (Ex. 1003) .............................................................................. ..27
`
`8. The '84l Publication ............................................................ ..29
`
`C. Objective Indicia of Non-Obviousness ........................................ ..3l
`
`D. The Patentability of Claims 1-5 Should be Affirmed ..................... .51
`
`E. The Patentability of Claims 7-9 Should be Affirmed ..................... ..59
`
`

`
`TABLE OF AUTHORITIES
`
`Page(s)
`
`Cases
`
`Alza Corp. v. Mylan Labs, Inc.,
`464 F.3d 1286 (Fed. Cir. 2006) ......................................................................... .. 51
`
`Amgen, Inc. v. Hoflman-LaRoclze Ltd.,
`580 F.3d 1340 (Fed. Cir. 2009). ........................................................................ .. 52
`
`Asblana’ Oil, Inc. 12. Delta Resins & Refractories, Inc,
`776 F.2d 281 (Fed. Cir. 1985), cert. denied, 475 U.S. 1017 (1986). ................ .. 48
`
`Crocs, Inc. v. International Trade Com ’n,
`598 F.3d 1294 (Fed. Cir. 2010) ......................................................................... .. 31
`
`Demaco Corp. v. F. Von Langsa’or;j"Lz'censz'ng Ltd.,
`851 F.2d 1387 (Fed. Cir), cert. denied, 488 U.S. 956 (1988) .......................... .. 48
`
`Eisai Co. v. Dr. Rea'a’y’s Labs, Lt'a'.,
`533 F.3d 1353 (Fed. Cir. 2008 .......................................................................... .. 52
`
`Ferring B. V v. Watson Labs, Inc.,
`764 F.3d 1401 (Fed. Cir. 2014) ......................................................................... .. 32
`
`Graham v. John Deere Co.,
`383 U.S. 1 (1966) .............................................................................................. .. 14
`
`Heiclelberger Druckmaschinen AG 12. Hantscho Commercial Prods. , Inc.
`21 F.3d 1068 (Fed. Cir. 1994) ........................................................................... .. 32
`
`In re Aller,
`220 F.2d 454 (C.C.P.A. 1955) ........................................................................... .. 51
`
`In re Clemens,
`622 F.2d 1029; 206 USPQ 289 (CCPA 1980) .................................................. .. 50
`
`In re Corkill,
`711 F.2d 1496, 226 USPQ 1005 (Fed. Cir. 1985) ............................................. ..36
`
`iii
`
`

`
`In re Cyclobenzaprine Hydrochloride Extended~Release Capsule Patent Litig.,
`676 F.3d 1063 (Fed. Cir. 2012) ......................................................................... .. 15
`
`In re Grasselli,
`
`713 F.2d 731 (Fed. Cir. 1983) ........................................................................... .. 50
`
`In re Translogic Tech., Inc.,
`504 F.3d 1249 (Fed. Cir. 2007). ........................................................................ .. 13
`
`KSR Int ’l Co. V. Teleflex Inc.,
`550 U.S. 398 (2007) .......................................................................................... .. 51
`
`Leo Pharmaceutical Products, Ltd. v. Rea,
`726 F.3d 1346 (Fed. Cir. 2013) ......................................................................... .. 31
`
`McG'inley v. Franklin Sports, Inc.
`262 F.3d 1339 (Fed. Cir. 2001) ......................................................................... ..32
`
`Medichem, S.A. v. Rolabo, S.L.,
`
`437 F.3d 1157 (Fed. Cir. 2006) ................................................................... .. 51, 52
`
`Ortho—McNeil Pharmaceutical Inc. v. Mylan Labs,
`520 F.3d 1358 (Fed. Cir. 2008) ....................................................... ..31, 32, 47, 52
`
`Par Pharmaceutical, Inc. v. TWI Pharmaceuticals, Inc.,
`773 F.3d 1186 (Fed. Cir. 2014) ......................................................................... .. 52
`
`Proctor & Gamble Co. v. Teva Pharms. USA, Inc,
`566 F.3d 989 (Fed. Cir. 2009) ..................................................................... .. 51, 52
`
`1
`Titanium Metals Corp, v. Banner,
`778 F.2d 775 (Fed Cir. 1985) ............................................................................ .. 51
`
`Transocean 0fi’shore Deepwater Drilling, Inc. v. Maersk Drilling USA, Inc.,
`699 F.3d 1340 (Fed. Cir. 2012) ......................................................................... ..32
`
`Statutes
`
`35 U.S.C. § 103(a) ................................................................................................... ..1
`
`Other Authorities
`
`M.P.E.P. § 716.04 .................................................................................................. ..32
`
`iv
`
`

`
`M.P.E.P. 716.01(b) ......................................................................................... ., ..... ..48
`
`M.P.E.P. 716.02(d) ......................................
`
`.......
`
`......
`
`....................................... .. 50
`
`Rules
`
`37 C.F.R. § 42.100(b) ............................................................................................ .. 12
`
`

`
`The patent at issue here is U.S. Patent No. 8,865,921 (“the ‘921 patent”),
`
`which is assigned to Patent Owner Furanix Technologies B.V. (“Furanix”).
`
`Petitioners, E.I. du Pont de Nemours and Company (“DuPont”) and Archer-
`
`Daniels-Midland Company (“ADM”), filed a Petition on August 28, 2015 (“the
`
`Petition”) requesting inter partes review (“IPR”) of claims 1-10 of the ‘921 patent.
`
`Paper 1 at 4-5. The PTO Board issued an Institution Decision (“the Decision”)
`
`ordering the institution of the present IPR.
`
`I.
`
`TECHNICAL BACKGROUND AND SUMMARY OF ARGUMENT
`
`The ‘921 patent is directed to exciting new processes for making 2,5-
`
`furandicarboxylic acid (“FDCA”) in surprisingly high yields, along with methods
`
`for esterifying FDCA. Ex. 1001, 2:39-45; Ex. 2003, ¶¶ 22-28. The inventors of
`
`the ‘921 patent were the first to develop a commercially viable process for making
`
`FDCA, operating at efficient temperature and pressure. Ex. 2003, ¶¶ 16, 22, 170.
`
`Claims 1-5 (to a process for making FDCA) and claims 7-9 (to a process for
`
`esterifying FDCA made as in claim 1) are subject to this IPR. The patentability of
`
`each of those claims should be affirmed. The cited prior art describes inefficient,
`
`non-commercially viable processes and does not teach or suggest the combination
`
`of temperature, oxygen partial pressure and catalyst operating parameters of the
`
`‘921 patent’s invention. The inventors engaged in far more than “routine
`
`optimization,” as the effect of altering those parameters was unpredictable. Ex.
`
`1
`
`

`
`2003, ¶¶ 17-21, 52, 64, 107-9. Further, even if there were a prima facie case of
`
`obviousness over the prior art, it is overcome by the very strong objective evidence
`
`of non-obviousness here, including unexpected results, satisfaction of a long-felt,
`
`but unmet need and copying by Petitioner ADM (in later filing a patent application
`
`describing the claimed subject matter of the ‘921 patent, see Ex. 2004).
`
`Table 1 of the ‘921 patent and recent testing performed by the Patent Owner
`
`for this IPR show the criticality of the claimed temperature range to producing
`
`unexpectedly high FDCA yields of almost 80% using the process of claims 1-5.
`
`Table 1 of the ‘921 patent demonstrates FDCA yields as high as 76.66% for the
`
`claimed process operating at 180 ºC when oxidizing when oxidizing 5-
`
`hydroxymethylfurfural (“HMF”), and a yield of 77.66% when oxidizing a mixture
`
`of HMF and an ester of HMF (5-(acetoxymethyl) furfural) or “AMF”) at the same
`
`temperature. Ex. 1001, col 7; Ex. 2003, ¶¶ 123-125. The Patent Owner’s recent
`
`tests repeated some of the experiments in Table 1 at 180 ºC (starting with HMF or
`
`HMF/AMF) and carried out the same experiments at temperatures of 145 ºC, 160
`
`ºC and 195 ºC, also using a Co/Mn/Br catalyst and oxygen partial pressure in the
`
`scope of the claims. At each of those temperatures, the FDCA yields approached
`
`80%. Ex. 2007, ¶¶ 35-38; Ex. 2003, ¶¶ 137-154.
`
`These yields are significantly higher than the 58.8% FDCA yield reported in
`
`the asserted closest prior art in this IPR, namely WO 0172732A2 (“the ‘732
`
`2
`
`

`
`publication,” Ex. 1002, assigned to Petitioner DuPont). Ex. 1002, 15-16 (Table 4).
`
`One of the named inventors on the ‘732 publication, Walter Partenheimer,
`
`authored a related publication in 2000 on behalf of DuPont (Ex. 1003, “the
`
`Partenheimer article” or “Partenheimer”), predicting that the maximum obtainable
`
`yield for oxidizing HMF to FDCA is “about 70%.” Ex. 1003, 105. Thus, the
`
`Patent Owner’s recent tests have demonstrated FDCA yields (almost 80%) using
`
`the process of claims 1-5 that are much higher than the ‘732 publication (58.8%)
`
`and even exceed the predicted theoretical maximum (about 70%).
`
`These results are very strong, objective evidence of the non-obviousness of
`
`the claims. This is particularly true for claim 2 of the ‘921 patent, which recites a
`
`feed comprised of a compound selected from the group consisting of HMF, esters
`
`of HMF and a mixture thereof, because the feed used for the Table 1 test and
`
`Patent Owner’s recent tests was HMF alone (both Table 1 and recent tests), or an
`
`HMF ester alone (Table 1) or an HMF/HMF ester mixture. Ex. 2003, ¶¶ 113-115,
`
`173.
`
`The beauty of FDCA is its role as a centerpiece of the “green” chemical
`
`industry. It can be made from HMF as a starting material (as recited in the ‘921
`
`patent), which itself is obtained from carbohydrate containing sources such as
`
`glucose, fructose, sucrose and starch. Ex. 2003, ¶¶ 16, 157; Ex. 2007, ¶ 10. FDCA
`
`is a replacement for terephthalic acid (“TA”), a petroleum-based monomer used to
`
`3
`
`

`
`produce polyethylene-terephthalate (“PET”). Ex. 2003, ¶¶ 14-15; Ex. 2007, ¶ 17;
`
`Ex. 2005, 28. The FDCA monomer can be used to create a wide range of
`
`polymers, such as polyesters, polyamides and polyurethanes, as well as coating
`
`resins, plasticizers and other chemical products. Scientists (including the ‘921
`
`patent inventors) at Avantium (which wholly owns Furanix) have been
`
`polymerizing FDCA, have been polymerizing FDCA with ethylene glycol to make
`
`a polyester called polyethylene-furanoate (“PEF”). PEF has excellent barrier and
`
`mechanical properties, so Avantium uses it to develop bottles, films (e.g., for food
`
`packaging) and fibers. PEF is a 100% bio-based alternative to PET. Ex. 2007¶¶
`
`17-21.
`
`FDCA was first identified in 1876. Ex. 1001, 1:30-32. Over 125 years after
`
`its discovery, the U.S. Department of Energy issued a 2004 report (“DOE report,”
`
`Ex. 2005) pointing to FDCA as one of 12 priority chemicals for establishing the
`
`green chemical industry. Ex. 2005, 1, 13; Ex. 2003, ¶ 157. However, the benefits
`
`of FDCA in the green chemical industry could not be realized before the invention
`
`of the ‘921 patent because there was not a commercially viable, efficient process
`
`for producing FDCA in high yields. Ex. 2003, ¶¶ 159-160. The 2004 report noted
`
`that there were technical barriers to producing FDCA in an industrially viable and
`
`cost effective manner, and that research and development work would have to take
`
`place. Ex. 2005, 26 (Table 13); Ex. 2003, ¶ 159; Ex. 2007, ¶ 11. There was a
`
`4
`
`

`
`long-felt need in the art for a solution to such technical barriers for making FDCA,
`
`so that the potential of the green chemical industry could be fully unlocked. None
`
`of the prior art cited in the institution of this IPR solved those problems or even
`
`suggested a viable solution.
`
`The inventors of the ‘921 patent solved this problem. They developed a
`
`commercially viable, efficient process for making FDCA at high yields, which was
`
`absent from the prior art. They achieved that by oxidizing a feed stream
`
`comprising a compound selected from HMF, an ester of HMF, related compounds
`
`and mixture thereof, in the presence of a Co/Mn/Br catalyst, at a temperature
`
`between 140 ºC and 200 ºC, at an oxygen partial pressure of 1 to 10 bar, and using
`
`an acetic acid solvent or water/acetic acid solvent mixture. Ex. 2003, ¶¶ 16, 170.
`
`The Decision found a reasonable likelihood that Petitioners will prevail in
`
`showing the obviousness of claims 1-5 over WO 0172732A2 (“the ‘732
`
`publication”), in combination with RU 448177 (“RU ‘177”) and U.S. Patent
`
`Publication 2008/0103318 (“the ‘318 application”). Patent Owner disputes that it
`
`would have been obvious to pick and choose from parts of these three references
`
`and combine them to create the claimed processes. Nor would a person of ordinary
`
`skill in the art (“POSA”) have been motivated to do so.
`
`Examples in the ’732 publication describe the conversion of HMF to FDCA
`
`at reaction temperatures of 100°C, 105°C, and 125°C, with the highest FDCA yield
`
`5
`
`

`
`(58.8%) obtained at 105°C and an oxygen pressure of 14.5 bar. Examples 38-40 of
`
`the ‘732 publication present a two-stage process for oxidizing HMF to
`
`diformylfuran (“DFF”) at 75 ºC and an oxygen partial pressure of 14.5 bar,
`
`followed by oxidizing that DFF product at 150 ºC and an oxygen partial pressure
`
`of 14.5 bar to produce FDCA, using a Co/Mn/Br/Zr catalyst and acetic acid solvent
`
`at each stage. The ‘732 publication’s process is performed at higher pressure and
`
`the oxidation of HMF is outside the temperature range recited in claims 1-5. The
`
`FDCA yields reported in the ‘732 publication top out at 58.8% when a temperature
`
`of 105°C was used (at Example 28). Ex. 1002, 15. There is no suggestion to
`
`oxidize HMF in the claimed temperature range and at lower oxygen partial
`
`pressures of 1-10 bar, as recited in claims 1-5. Ex. 2003. ¶¶ 47-59.
`
`Likewise RU ‘177 fails to disclose the claimed process. RU ‘177 describes
`
`a process for oxidizing 5-MF in the presence of acetic acid and a Co/Mn/Br
`
`catalyst, operating at a temperature of 115-140 ºC and air pressure of 10-15 atm or
`
`10-50 atm. In Example 1 of RU ‘177, the air pressure is 20-30 atm (about 4-6 bar
`
`oxygen partial pressure), the temperature is 118-130 ºC, and the reported FDCA
`
`yield is 36%. Ex. 1007, 2. RU ‘177 does not describe the combination of features
`
`in the process of claims 1-5. Ex. 2003. ¶¶ 67-68.
`
`The ‘318 application describes oxidizing HMF to produce FDCA, using
`
`either air or O2 as the oxidant and a preferred pressure of 150-500 psi. Ex. 1008 ¶
`
`6
`
`

`
`[0050]. The actual oxygen partial pressure in the process of this application is
`
`ambiguous since one does not know what the gaseous feed stream actually
`
`comprises. The temperature range for the oxidation can be from 50 ºC to about
`
`200 ºC, with a preferred range of from 100 ºC through about 160 ºC. Id. The ‘318
`
`application’s process is a fixed-bed process using an extremely diluted feedstock
`
`and a different catalyst (Pt/ZrO2) from the Co/Mn/Br catalyst recited in the claims
`of the ‘921 patent. Id., ¶¶ [0067]-[0068]. While it may produce high yields of
`
`FDCA, it does it in a much different way than the ‘921 patent’s process and it is
`
`not a commercially viable process. Ex. 1008, ¶¶ 69-76. Finally, the Examples of
`
`the ‘318 application use water as a solvent (Ex. 1008, ¶¶ [0067-69]), in contrast to
`
`the acetic acid or acetic acid/water solvent of claims 1-5 of the ‘921 patent.
`
`According to the Decision, “in the absence of any showing of criticality or
`
`unexpected results associated with the claimed temperature ranges,” it would have
`
`been obvious to optimize the temperature between 140 ºC and 200 ºC following the
`
`teachings of the ‘732 publication, and to further optimize the oxygen partial
`
`pressure to 1-10 bar based on the teachings of RU ‘177 and the ‘318 application.
`
`There is nothing in the ‘732 publication that suggests oxidizing HMF (or any other
`
`starting material in claims 1-5) in that temperature range, much less lowering the
`
`operating pressure to 1-10 bar in view of other references with a lower yield (RU
`
`‘177) or commercially non-viable steps and ambiguous teachings as to pressure
`
`7
`
`

`
`(the ‘318 application). The effect of raising the oxidation temperature on yield was
`
`shown in Partenheimer to be unpredictable. Ex. 1003, 105; Ex. 2003, ¶ 64.
`
`Moreover, Patent Owners have now demonstrated a higher FDCA yield (nearly
`
`80%) at 145 ºC than the ‘732 publication achieved (54%) at a higher temperature
`
`of 150 ºC. Finally, lowering the pressure would be counterintuitive relative to
`
`increasing yields, as a POSA would want more oxygen in the process as a reactant,
`
`not less. Ex. 2003, ¶ 112.
`
`Even if such a combination were prima facie obvious, Patent Owner has
`
`resoundingly demonstrated the criticality of the claimed temperature range
`
`(between 140 ºC and 200 ºC), in combination with the other claim features, for
`
`producing FDCA in unexpectedly high yields. This strong evidence of unexpected
`
`results, together with the satisfaction of a long-felt need for a commercially viable
`
`process for making FDCA and evidence of copying by ADM in the ‘755
`
`publication, demonstrate the non-obviousness of claims 1-5 and together overcome
`
`any prima facie obviousness case for those claims.
`
`The Decision also found that there is a reasonable likelihood that Petitioners
`
`will prevail in showing that claims 7-9 of the ‘921 patent would have been obvious
`
`over the combination of the ‘732 publication, Admitted Prior Art (i.e., that
`
`esterifying FDCA was “known”), an article by Lewkowski (“Lewkowski”), an
`
`article by Oae (“Oae”), RU ‘177 and the ‘318 application, which Petitioners
`
`8
`
`

`
`asserted as Ground 3 in their IPR Petition. Paper 1 at 4. Independent claim 7
`
`recites the same process steps as claim 1, with the additional step of esterifying the
`
`FDCA obtained by that process. Claims 8 and 9 depend from claim 7. For the
`
`same reasons discussed above, the ‘732 publication, RU ‘177 and the ‘318
`
`application do not render the FDCA oxidation process recited in claims 7-9
`
`obvious, and none of Admitted Prior Art, Lewkowski or Oae fills in any of the
`
`above deficiencies or overcomes the strong objective indicia of non-obviousness.
`
`The patentability of claims 7-9 should be affirmed as well.
`
`II.
`
`The ‘921 Patent, Prosecution History and Claims Construction
`
`A. The ‘921 Patent’s Specification and Claims
`
`The invention of the ‘921 patent is a commercially viable, efficient process
`
`for producing FDCA by oxidizing HMF, an ester of HMF or related compounds
`
`and mixtures, at a particular temperature range, pressure range, catalyst and
`
`solvent, which provides unexpectedly high yields compared to the prior art. Ex.
`
`2003, ¶¶ 22-27, 123-162; Ex. 1001, 2:39-45. Claim 1 of the ‘921 patent recites a
`
`method of preparing FDCA by oxidizing a feed comprising a compound selected
`
`from the group consisting of HMF, an ester of HMF, 5-methylfurfural, 5-
`
`(chloromethyl)furfural, 5-methylfuroic acid, 5-(chloromethyl)furoic acid, 2,5-
`
`dimethylfuran (“DMF”) and a mixture of two or more of these compounds, in the
`
`presence of a catalyst comprising Co, Mn and Br, at a temperature between 140 ºC
`
`9
`
`

`
`and 200 ºC, at an oxygen partial pressure of 1 to 10 bar, using an acetic acid
`
`solvent or water/acetic acid solvent mixture. Ex. 1001, 7:61-8:6. Claims 2-5
`
`depend from independent claim 1 and add further limitations. Claim 2 narrows the
`
`feed stream to HMF, esters of HMF and a mixture thereof. Claim 3 requires at
`
`least one additional metal in the oxidation catalyst. Claim 4 depends from claim 3
`
`and states that the additional metal is Zr and/or Ce. Claim 5 narrows the
`
`temperature range to between 160 and 190 ºC. Ex. 1001, 8:7-63.
`
`Independent claim 7 is directed to a method for the preparation of a dialkyl
`
`ester of FDCA and recites the same process steps as claim 1, with the additional
`
`step of esterifying the FDCA obtained by that process. Claims 8 and 9 depend
`
`from claim 7 and further specify that the FDCA is esterified with a C1-C5 alcohol
`
`(claim 8) and that the C1-C5 alcohol is methanol and the dialkyl ester is the
`
`dimethylester of FDCA (claim 9). Ex. 1001, 9:1-19.
`
`The ‘921 patent describes that FDCA was identified as a priority chemical
`
`for the “green” chemical industry by the U.S. Department of Energy, in a 2004
`
`report. Ex. 1001, 1:34-36 (citing Ex. 2005). The patent further states that FDCA
`
`can be prepared by oxidizing HMF obtained from carbohydrate containing sources
`
`such as glucose, fructose, sucrose and starch. Ex. 1001, 1:38-43. The ‘921 patent
`
`specification describes certain prior art, including the ‘732 publication and
`
`Partenheimer, and notes that the highest FDCA yield realized in those prior art
`
`10
`
`

`
`processes was 59% in the ‘732 publication. Ex. 1001, 1:49-36.
`
`B. Prosecution History of the ‘921 Patent
`
`The ‘921 patent issued on October 21, 2014 from Application Serial No.
`
`13/497,690 (“the ‘690 application”) filed on October 6, 2010, which claims
`
`priority to a Provisional Application (No. 61/249,395) filed on October 7, 2009.
`
`Notably, the originally-filed claims of the ‘690 application recited a
`
`temperature range “higher than 140°C” (see Ex. 1011 at page 28 of 629, original
`
`claim 1) and there are dependent claims from original claim 1 (i.e., original claim
`
`9) that further limit this range to “between 140 and 200°C.” Id. This demonstrates
`
`that the ordinary meaning of “between 140 °C and 200 °C” in claim 1 of the ‘921
`
`patent is that the temperature of oxidation is between those two temperatures and
`
`does not include either temperature point of 140 °C or 200 °C.
`
`The original claims were rejected for anticipation over Sanborn US
`
`2009/0156841 (Ex. 1011, 165) and later, after amendment to require a further
`
`source of bromine in the Co/Mn catalyst, they were rejected for obviousness over
`
`the combination of Sanborn and Gruter. (Ex. 1011, 198). In response, the
`
`Applicants pointed to the experiments of Table 2 of the ‘921 patent’s specification,
`
`which compares the FDCA yields achieved using the claimed invention to oxidize
`
`AMF at 180 ºC to those realized using the Sanborn process to oxidize AMF at 100
`
`ºC. Ex. 1011, 223-24. The FDCA yields using the claimed process are much
`
`11
`
`

`
`higher in Table 2 (up to 64.82%) than those of Sanborn (topping out at 29.05%).
`
`The PTO then allowed the claims. Ex. 1011, 629.
`
`C. “Construction” of the Claims in the ‘921 Patent
`
`As noted in the Decision, the broadest reasonable construction standard
`
`applies to claims in an IPR, as set forth in 37 C.F.R. § 42.100(b). Paper 10, 6.
`
`Under that standard, claim terms are given their ordinary and customary meaning,
`
`as would have been understood by a person of ordinary skill in the art at the time
`
`of the invention. In re Translogic Tech., Inc., 504 F.3d 1249, 1257 (Fed. Cir.
`
`2007). The Decision found that “no explicit construction” of any claim term was
`
`necessary to institute the IPR. Patent Owner agrees, as the ordinary and customary
`
`meaning of each claim term is apparent on its face. The various compounds of the
`
`feed (e.g., HMF, HMF ester, 5-MF, DMF) and the product (FDCA) in the claimed
`
`processes certainly need no construction, as they are chemical compounds with
`
`recognized meanings in the art. The same is true of the recited process steps.
`
`Moreover there is absolutely no support for the arguments made by
`
`Petitioners in their attempt to construe the claim terms reciting the temperature
`
`range (between 140 ºC and 200 ºC in claim 1; between 160 ºC and 190 ºC in claim
`
`5) or oxygen partial pressure range (1 to 10 bar). According to Petitioners’ expert,
`
`Dr. Martin, the ranges “between 140° C. and 200° C and between 160° C. and 190°
`
`C” would include the temperature limits 140°C, 160°C, 190°C and 200°C.” See
`
`12
`
`

`
`Martin Decl. (Ex. 1009) at ¶ 53. The ordinary and customary meaning of the word
`
`“between” to a POSA would mean that the points 140°C and 200°C (in claims 1
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`and 7) and 160°C and 190°C (in claim 5) are not included in the recited ranges.
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`Dr. Schammel agrees. Ex. 2003, ¶¶ 37-43.
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`The specification in column 4 recites a preferred temperature range of
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`“between 160 and 190 °C.” The originally-filed claims of the ‘690 application
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`recited a temperature range “higher than 140°C” (see Ex. 1011 at 28 of 629,
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`original claim 1) and there are dependent claims from original claim 1 (original
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`claim 9) that further limit this range to “between 140 and 200 °C.” Id. Thus, a
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`temperature “between” 140 and 200 °C plainly excludes the 140 °C point in the
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`‘921 patent since the original claims dictate that it must be at least “higher” than
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`140 °C. Dr. Martin also admitted at his deposition that a POSA would understand
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`that the temperature range “higher than 140°C” would not include 140°C. See e.g.,
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`Martin Depo. (Ex. 1027) 107:5-8. For the same reasons, a POSA would also
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`understand that the phrase “between 160° C. and 190° C,” recited in claim 5,
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`would not include the points of 160°C and 190°C.
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`Likewise, the recitation of 1 to 10 bar for oxygen partial pressure in the
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`claims has an ordinary and customary meaning that would be plain to a POSA at
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`the time of invention. There is no basis for importing the word “about” into the
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`literal meaning of this claim term as advocated by Petitioners. An “oxygen partial
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`13
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`pressure of 1 to 10 bar” means what it says and needs no further construction.
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`IV. ARGUMENT – PATENTABILITY SHOULD BE AFFIRMED
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`An obviousness analysis involves four factors: (1) the “scope and content of
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`the prior art; (2) “the level of ordinary skill in the art”; (3) “differences between the
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`prior art and the claims at issue”; and (4) objective “indicia of obviousness or non-
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`obviousness,” also called secondary considerations. Graham v. John Deere Co.,
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`383 U.S. 1, 17-18 (1966). The Petitioners bear the burden of proof throughout the
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`analysis, and all four factors must be considered in making the determination. In
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`re Cyclobenzaprine Hydrochloride Extended-Release Capsule Patent Litig., 676
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`F.3d 1063, 1075 (Fed. Cir. 2012). Here, the patentability of claims 1-5 and 7-9
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`should be affirmed over the prior art. There is no prima facie obviousness case.
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`A. A Person of Ordinary Skill in the Art
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`As explained by Dr. Schammel, a person of ordinary skill in the art (or
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`“POSA”) in 2009 would have been a person having at least a bachelor’s degree in
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`chemistry or chemical engineering, having worked in the field of chemical process
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`development for at least five years and having experience in the preparation of
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`furan compounds from biomass and in the catalysis of oxidation of furan
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`compounds for a similar period. Ex. 2003, ¶ 44.
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`In his declaration, Dr. Martin described a higher level of education for a
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`POSA, reqiring a Ph.D. (Ex. 1009, ¶ 14), but he later broadened his definition of a
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`14
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`POSA in his deposition. There, he testified that such a person would also include
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`individuals with a bachelor’s degree or master’s degree in chemistry with
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`appropriate experience in the field of catalysis. Martin Depo. (Ex. 1027) 112:21-
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`114:2. In either case, whether Dr. Schammel uses his own POSA definition or the
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`original one posited in Dr. Martin’s declaration, Dr. Schammel’s opinions on the
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`non-obviousness of claims 1-5 and 7-9 do not change. Ex. 2003, ¶ 46.
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`B. The Asserted Prior Art and Its Differences from the Claims at Issue
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`1. WO 01/72732 (“the ’732 Publication, Ex. 1002)
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`WO 01/72732 (“the ’732 publication, Ex. 1002) does not teach or suggest
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`the methods of the claimed invention. Ex. 2003, ¶¶ 47-59. Examples in the ’732
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`publication describe the conversion of HMF to FDCA at reaction temperatures of
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`100°C, 105°C, and 125°C, with the highest FDCA yield (58.8%) obtained at
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`105°C and a pressure of 14.5 bar. Ex. 1002, 14-15. Examples 38-40 of the ‘732
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`publication present a two-stage process for oxidizing HMF to diformylfuran
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`(“DFF”) at 75 ºC and an oxygen partial pressure of 14.5 bar, followed by oxidizing
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`that DFF product at 150 ºC and an oxygen partial pressure of 14.5 bar to produce
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`FDCA, using a Co/Mn/Br/Zr catalyst and acetic acid solvent at each stage. Ex.
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`2003, ¶¶ 56-59; Ex. 1002, 16.
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`Thus, the ‘732 publication’s process is done at higher pressure and the
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`oxidation of HMF is outside the temperature range recited in claims 1-5.
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`15
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`

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`Examples 16-40 in the ’732 publication use an oxygen partial pressure that is 44%
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`higher than the claimed range. Those examples use air at 1000 psi, which converts
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`to 68.97 bar air, or a partial pressure of oxygen of 14.5 bar. The FDCA yields
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`reported in the ‘732 publication top out at 58.8% (at Example 28). Ex. 2003, ¶ 49;
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`Ex. 1002, 15.
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`The ’732 publication does not teach or suggest an oxygen partial pressure of
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`1 to 10 bar as recited in the ’921 patent claims. Ex. 2003, ¶¶ 48-9. The disclosure
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`in the ’732 publication that “corresponding pressure is such to keep the solvent
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`mostly in the liquid phase” (see p. 7, lines 4-5) would not teach or suggest the
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`claimed oxygen partial pressure of 1 to 10 bar because it relates to the total
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`pressure in the reaction chamber. It does not describe the partial pressure of
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`oxygen, as Dr. Martin confirmed in his deposition. Martin Depo. (Ex. 1027)
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`114:6-115:1.
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`The ’732 publication states that “for preparation of the diacid, the preferred
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`temperatures are about 50° to 250°C, most preferentially about 50° to 160°C.”
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`’732 publication (Ex. 1002) p. 7, lines 2-4. This disclosure does not provide the
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`range recited in claim 1 (between 140 and 200°C) or in claim 5 (between 160 and
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`190°C). In addition, in the two-staged reactions performed at 75°C for two hours
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`and 150°C for two hours, the reaction at 150°C contains no HMF because it was
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`converted to other compounds during the first stage of the reaction. Ex. 2003, ¶¶
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`16
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`

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`56-59.
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`Likewise, the ’732 publication would not have provided a POSA with the
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`motivation to use increased temperatures. Examples 38-40 of the ’732 publication
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`demonstrate that the two-stage reactions with 2 hours at 75°C and 2 hours at 150°C
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`have some of the highest levels of CFF intermediate. Reactions performed at
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`lower temperatures, 105°C and 125°C, generally have lower amounts of CFF.
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`’732 publication (Ex. 1002), p 15 (see, e.g., examples 22, 32, and 33). The staged
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`reactions (with 2 hours at 150°C) have more of the CFF intermediate than many
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`reactions at lower temperatures. A person of ordinary skill in the art would
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`therefore not have concluded based on the data in the ’732 publication that
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`increased temperature would drive the reaction toward increased yield. Ex. 2003, ¶
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`51.
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`Petitioners and Dr. Martin simply cherry pick from the ’732 publication,
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`especially from Table 4, to make their arguments. Dr. Martin selects reactions
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`showing “increasing FDCA yield with a temperature change from 100°C to
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`125°C.” Ex. 1009, ¶ 92. However, increasing the temperature does not necessarily
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`increase yield as demonstrated by Table 4 of the ’732 publication. Comparing
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`examples 20 and 25, and examples 19 and 24 (reproduced below) f