Trials@uspto.gov
`571-272-7822
`
`Paper No.43
`Entered: March 3, 2017
`
`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,
`
`Vv.
`
`FURANIX TECHNOLOGIESB.V.,
`Patent Owner.
`
`Case IPR2015-01838
`Patent 8,865,921 B2
`
`Before TONI R. SCHEINER, SHERIDAN K. SNEDDENand
`CHRISTOPHER G. PAULRAJ, Administrative Patent Judges.
`
`PAULRAJ, Administrative Patent Judge.
`
`FINAL WRITTEN DECISION
`35 U.S.C. § 318(a) and 37 CER. § 42.73
`
`

`

`IPR2015-01838
`Patent 8,865,921 B2
`
`lL
`
`INTRODUCTION
`
`E. J. du Pont de Nemours and Company and Archer-Daniels-Midland
`
`Company(collectively, “Petitioners”’) filed a Petition (Paper1, “Pet.”),
`
`requesting institution of an inter partes review of claims 1—10 of
`
`U.S. Patent No. 8,865,921 B2 (Ex. 1001, “the °921 Patent”). Furanix
`
`Technologies B.V. (“Patent Owner”) did not file a Preliminary Response.
`
`Wehavejurisdiction under 35 U.S.C. § 314, which provides that an inter
`
`partes review may notbeinstituted “unless. .
`
`. there is a reasonable
`
`likelihood that the petitioner would prevail with respect to at least 1 of the
`
`claims challengedin the petition.” We determined that the information
`
`presented in the Petition demonstrated that there was a reasonable likelihood
`
`that Petitioners would prevail in challenging claims 1—5 and 7-9 as
`
`unpatentable under 35 U.S.C. § 103(a). Pursuantto 35 U.S.C. § 314,the
`
`Boardinstituted trial on March 9, 2016, as to those claims of the ‘977 Patent.
`
`Paper 10 (“Institution Decision”; “Inst. Dec.”). We denied Petitioners’
`
`request for rehearing of our decision to denyinstitution as to the
`
`patentability challenge for claims 6 and 10. Paper 20.
`
`Following ourinstitution, Patent Ownerfiled a Response to the
`
`Petition. Paper 23 (“PO Resp.”). Petitioners filed a Reply to Patent
`
`Owner’s Response. Paper 29 (“Reply”). An oral hearing was held on
`
`November 16, 2016. The transcript of the hearing has been entered into the
`
`record. Paper 42 (‘‘Tr.”).
`
`Wehavejurisdiction under 35 U.S.C. § 6. This Final Written
`
`Decision is issued pursuant to 35 U.S.C. § 318(a) and 37 C.F.R. § 42.73.
`
`Based on the record before us, we conclude that Petitioners have not
`
`demonstrated by a preponderanceof the evidencethat claims 1-5 and 7-9 of
`
`

`

`IPR2015-01838
`Patent 8,865,921 B2
`
`the ’921 Patent are unpatentable based on the obviousness challenges
`
`presented in the Petition.
`
`A.
`
`Related Proceedings.
`
`The parties have not identified any separate related matters under 42
`CFR.§ 42.8(b)(2). Pet. 1; Paper5, 1.
`|
`B.
`The ’921 Patent (Ex. 1001)
`
`The °921 patent issued on October 21, 2014, and claimspriority to a
`
`provisional application filed on October 7, 2009.. See Ex. 1001, Title Page.
`
`It names Cesar Mufioz De Diego, Matheus Adrianus Dam,and Gerardus
`
`Johannes Maria Gruter as the inventors. Jd.
`
`The ’921 patent relates generally to methods for preparing 2, 5-furan
`dicarboxylic acid (FDCA), or a dialkyl ester of FDCA,bycontacting 5-
`.
`hydroxymethylfurfural (HMF), and/or derivatives thereof, with an oxygen-
`
`containing gas in the presence of oxidation catalysts comprising cobalt (Co),
`
`manganese (Mn), and bromine (Br)(i.e., a Co/Mn/Brcatalyst), and an acetic
`
`acid solvent at elevated temperatures. Jd., Abstract, 1:18-26, 2:39-45. The
`
`’921 patent states that “FDCA can be producedin particular from esters of
`
`HMF,such as for example 5-acetoxymethylfurfural (AMF) or a mixture of
`
`one or more of these compounds with HMF,such as for example from a
`
`mixture of AMF and HMF.” Jd. at 1:21-24. The 921 patent further
`
`discusses the use of FDCA obtained according to the process described
`
`therein to prepare a dialkyl ester of 2,5-dicarboxylic acid by the reaction of
`
`FDCAwith a Ci-Cs alkyl alcohol. Jd. at 5:20-41. The 921 patent
`
`acknowledgesthat the esterification of FDCA was knownin thepriorart.
`
`Id. at 5:42-58.
`
`

`

`IPR2015-01838
`Patent 8,865,921 B2
`
`According to the 921 patent, FDCA has beenidentified as a priority
`
`chemical for establishing a “green” chemistry industry, but no commercial
`
`process exists for its production. Jd. at 1:34-38. The specification states
`
`that FDCA,a furan derivative, is often synthesized in the laboratory from
`
`HMF obtained from carbohydrate containing sources such as glucose,
`
`fructose, sucrose, and starch. Jd. at 1:30-43. The derivatives of HMF are
`
`knownto be potential and versatile fuel components and precursors for the
`
`production ofplastics. Id. at 1:44-46. The specification identifies prior art
`
`processes for the oxidation of HMF to FDCA with a Co/Mn/Brcatalyst at
`
`temperatures ranging from 50 to 125°C, whichresulted in low reactivity or
`
`yield loss. Id. at 1:48-67, 2:1-35. The ’921 patent seeks to improveprior
`
`art yields by controlling the temperature and/or pressure under which the
`
`oxidation reaction occurs. Id. at 4:34-61.
`
`In particular, the °921 patent specification explains that “[t]he pressure
`
`in a commercial oxidation process may vary within wide ranges,” and “is
`
`determined by the solvent(e.g., acetic acid) pressure at a certain
`
`temperature.” Jd. at 4:34-39. Moreover, the pressure is preferably selected
`
`to maintain the solvent in the liquid phase, which “meansthat pressures
`
`between 5 and 100 bar can be used with a preference for pressures between
`
`10 and 80 bar.” Id. at 4:39-43. The oxidant can be an oxygen-containing
`
`gas, such as air, which “can be continuously fed to and removed from the
`
`reactor,” in which case “the oxygen partial pressure will suitably be between
`
`1 and 30 bar or more preferably between 1 and 10 bar.” Jd. at 4:43-46, 51-
`
`55. Conversely, all of the oxygen-containing gas can be supplied at the start
`
`of the reaction, but this will require a significantly higher pressure. Jd. at
`
`4:45-51. The specification further explainsthat “[t]he temperature of the
`
`

`

`IPR2015-01838
`Patent 8,865,921 B2
`reaction mixtureis at least 140° C., preferably from 140 and 200° C., most
`preferably between 160 and 190° C.” Jd. at 4:56-58. The specification
`
`notes that “[g]ood results” were achieved at about 180°C, but cautionsthat
`
`“Tt]emperatures higher than 180° C maylead to decarboxylation and to other
`
`degradation products.” Jd. at 4:58-61.
`
`The 921 patent includes working examples describing experiments in
`
`which the oxidation reaction wascarried out with a Co/Mn/Brcatalyst at an
`
`air pressure ranging from 20—60 bars and temperatures ranging from 100 to
`
`220°C. Id. at 6:8-11. More particularly, Example 1 describes the oxidation
`
`of HMF and/or AMF at 180°C for 1 hour with 20 barair pressure, which
`
`resulted in FDCAyields of up to 78.08%. Id. at 6:34-46, Table 1. Example
`
`2 provides a comparative example in which AMF oxidation was conducted
`
`at 100°C and 30 bar for 2 hours, showing that FDCA yields under those
`
`conditions were lower than the results obtained at higher temperature. Jd. at
`
`6:50-62, Table 2.
`
`C. Illustrative Claims
`
`Claims 1—5 and 7-6 are challengedin this inter partes review.
`
`Independent claim 1 is illustrative, and reproduced below:
`
`1. A methodfor the preparation of 2,5-furan dicarboxylic acid
`comprising the step of contacting a feed comprising a compound
`selected from the group consisting of S-hydroxymethylfurfural
`(“HMF”), an ester of 5-hydroxymethylfurfural, 5-methylfurfural, 5-
`(chloromethyl)furfural, S-methylfuroic acid, 5-(chloromethy])furoic
`acid, 2,5-dimethylfuran and a mixture of two or more of these
`compoundswith an oxygen-containing gas, in the presence of an
`oxidation catalyst comprisingboth Co and Mn,andfurther a source of
`bromine,at a temperature between 140° C and 200° C at an oxygen
`partial pressure of 1 to 10 bar, wherein a solvent or solvent mixture
`comprising acetic acid or acetic acid and water mixturesis present.
`
`

`

`IPR2015-01838
`Patent 8,865,921 B2
`
`Independent claim 7 is directed to the preparation of a dialkyl ester of
`
`FDCA,and additionally recites the step of “esterifying the thus obtained
`
`product.”
`
`D. Patentability Challenges
`The following patentability challenges are at issue in this proceeding:
`
`
`
`
`
`
`
`The ’732 publication,’ RU
`°177,2 and the ’318 application?
`The ’732 publication,
`Lewkowski,’ Oae,° RU 7177,
`and the °318 application
`
`§ 103(a)
`
`§ 103(a)
`
`1-5
`,
`7-9
`
`In addition to the teachings of the references, Petitioners rely upon the
`
`Declarations of Kevin J. Martin, Ph.D. (Ex. 1009; Ex. 1028) in support of
`
`these challenges.
`
`1 Grushin et al., WO 01/72732 A2, published Oct. 4, 2001 (Ex. 1002).
`? Slavinskayaet al., USSR Patent RU-448177A1, published Oct. 30, 1974
`(Ex. 1007, with certified English translation).
`3 Lilga et al., US 2008/0103318 Al, published May 1, 2008 (Ex. 1008).
`* Lewkowski, Synthesis, Chemistry and Applications of5-
`Hydroxymethylfurfural andits Derivatives, ARKIVOC 2001 (i) 17-54,
`Published Online on Aug. 8, 2001 (Ex. 1005).
`> Oae et al., A Study ofthe Acid Dissociation ofFuran- and
`Thiophenedicarboxylic Acids and ofthe Alkaline Hydrolysis ofTheir Methyl
`Esters, SOC. JPN. 1965, 38, Aug. 1965, at 1247 (Ex. 1006).
`
`6
`
`

`

`IPR2015-01838
`Patent 8,865,921 B2
`
`Il.
`
`DISCUSSION
`
`A. Claim Construction
`
`Weinterpret claims of an unexpired patent using the “broadest
`
`reasonable constructionin light of the specification of the patent in which
`
`[they] appear[].” 37 C.F.R. § 42.100(b); Cuozzo Speed Techs., LLC v. Lee,
`
`136 S. Ct. 2131, 2146 (2016). Under the broadest reasonable construction
`
`standard, claim termsare given their ordinary and customary meaning,as
`
`would be understood by one 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). “Absent claim language carrying a narrow meaning, the PTO should
`
`only limit the claim based on the specification .
`
`.
`
`. when [it] expressly
`
`disclaim[s] the broaderdefinition.” Jn re Bigio, 381 F.3d 1320, 1325 (Fed
`
`Cir. 2004). “Although an inventoris indeed free to define the specific terms
`
`used to describe his or her invention, this must be done with reasonable
`
`clarity, deliberateness, and precision.” In re Paulsen, 30 F.3d 1475, 1480
`
`(Fed. Cir. 1994).
`
`Wedeterminethat no explicit construction of any claim term is
`
`necessary to resolve the issues in this case. See, e.g., Wellman, Inc. v.
`
`Eastman Chem. Co., 642 F.3d 1355, 1361 (Fed. Cir. 2011) (“[C]laim terms
`
`need only be construed ‘to the extent necessary to resolve the
`
`controversy.””) (quoting Vivid Techs., Inc. v. Am. Sci. & Eng’g, Inc.,
`
`200 F.3d 795, 803 (Fed. Cir. 1999)).
`
`B. Prior Art Relied Upon
`
`Petitioners rely upon the followingpriorart in their challenges.
`
`

`

`IPR2015-01838
`Patent 8,865,921 B2
`
`J. The '732 publication (Ex. 1002)
`The ’732 publication describes the oxidation of HMF to FDCA,and
`
`the subsequent decarbonylation to unsubstituted furan. Ex. 1002, Title,
`2:17-20.° The catalyst used for the oxidation process described in the ’732
`
`publication “can be comprised of Co and/or Mn,and Br, and optionally
`
`{[zirconium,] Zr.” Jd. at 6:22—24. Acetic acid is identified as a preferred
`
`solvent because FDCAis insoluble in it, thereby facilitating purification. Jd.
`
`at 9:14-21.
`
`The ’732 publication explains further that “[f]or preparation of diacid,
`
`the preferred temperatures are about 50° to 250°C, most preferentially about
`50° to 160°C,”and “[t]he corresponding pressure is such to keep the solvent
`mostly in the liquid phase.” Jd. at 8:2-5. The ’732 publication discloses
`
`‘examples wherein “[p]lacing HMF in reactors with acetic acid and catalyst
`
`metals and having them react with air at 1000 psi (7 MPa) gave goodyields
`
`of FD[C]A.” Jd. at 16:3-4. In Examples 38-40,“the temperature was
`
`staged — initially it was held at 75°C for 2 hrs. and then raised to 150°C for
`
`two hrs,” which “gave higher yields.” Jd. at 16:13—15, Table 4.
`
`The ’732 publication is identified as prior art in the background
`
`section of the ’921 patent, which indicates that “[t]he maximum FDCAyield
`reported is 59%, obtained at 105° C.” Ex. 1001, 1:48-50.
`
`6 The ’732 publication uses the acronym “FDA”for 2,5-furan dicarboxylic
`acid. For the sake of consistency, we will refer to the compound as FDCA.
`Wealso refer herein to the page numbers addedto the very bottom ofthe
`exhibit (e.g., “Petitioners’ Exhibit 1002, Page 2 of 23”).
`
`8
`
`

`

`IPR2015-01838
`Patent 8,865,921 B2
`
`2. RU 7177 (Ex. 1007)
`
`RU 7177 is an “Inventor’s Certificate” issued by the former Union of
`
`Soviet Socialist Republics (USSR), which also teaches a method for
`
`producing FDCA. Ex. 1007, Title. Specifically, RU ’177 claims a process
`
`of producing FDCA using air oxidation wherein “5-methylfurfural [SMF]is
`
`subject to oxidation and mixed valance metalsalts, such as a mixture of
`
`cobalt acetate and manganeseacetate, as well as bromine-containing
`
`compounds, such as ammonium bromide,in the aliphatic carboxylic acid
`
`solution are used as a catalyst.” Jd. at 2, col. 4 (claim 1). RU 7177 also
`
`includes a claim specifying that the “oxidation is conducted at the
`
`temperature of 115—140°C andair pressure of 10-50 atm.” Jd. at 2, col. 4
`
`(claim 2). RU ’177 further discloses that oxidation is “typically conducted
`
`under 115-140°C and air pressure of 10-15 atm.” Jd. at 1, col. 1. In
`
`Example 1 of RU °177, SMF wasreacted at 118°C and 20 atm of pressure
`
`(4.26 bar pO2) for 4.5 hours and then the temperature was increased to
`
`130°C andpressure increased to 30 atm (6.38 bar pOz2). Jd. at 2, col. 3.
`
`RU 7177 states the method disclosed therein has a numberof
`
`advantages,i.e., “it utilizes readily available and inexpensive reagents as the
`
`initial compound and catalysts [and] the methodis a one-step process.” Id.
`
`at 1, col. 2.
`
`3. The ’318 application (Ex. 1008)
`
`The °318 application also relates to a method of oxidizing HMF to
`
`produce various derivatives, including FDCA. Ex. 1008 4 3. More
`
`specifically, the 7318 application teaches that “[t]he starting material
`
`comprising HMF is provided into a reactor andat least one ofair or O2is
`
`provided as oxidant.” Jd. 450. The ’318 application indicatesthat,
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`

`

`IPR2015-01838
`Patent 8,865,921 B2
`
`depending uponthe desired reaction rate, the pressure utilized may range
`
`from atmospheric pressure to the pressure rating of the equipment, and “[a]
`
`preferred pressure can typically be in the range of 150-500 psi.” Jd.
`
`“Similarly an appropriate reaction temperature can be from about 50° C to
`
`about 200° C, with a preferred range of from 100° C through about 160° C.”
`
`Id.
`
`The °318 application states that “under particular reaction conditions,
`
`HMF conversions of 100% were achieved with selectivity to FDCA as high
`
`as 98% relative to all other reaction products, intermediates and
`
`byproducts.” Jd. 955. In Example 1, 98% FDCAselectivity was achieved
`
`using a Pt/ZrO2 catalyst under conditions of 150 psi pressure and 100°C
`
`temperature. Id. {| 67-68.
`
`4. Lewkowski (Ex. 1005)
`
`Lewkowski discusses the methods of synthesis of FDCA,andits
`
`chemistry and application. Ex. 1005, 17. Lewkowskistates “[t]he synthesis
`
`of diethyl ester and dimethyl ester .
`
`.
`
`. have been reported.”Jd. at 44.
`
`Lewkowskicites Oae (Ex. 1006) for the synthesis process of dimethy]ester.
`
`Id. Lewkowski discloses that the diethyl ester of FDCA has “a strong
`
`anaesthetic action similar to cocaine,” and that another ester form of
`
`FDCA—dicalcium 2,5-furandicarboxylate—was shownto haveantibacterial
`
`activity. Id. at 45.
`
`5. Oae (Ex. 1006)
`
`Oaerelates to the acid dissociation of furandicarboxylic acids and the
`
`alkaline hydrolysis of their methyl esters. Ex 1006, 1247. Specifically,
`
`Oaestates that dimethyl esters of FDCA were synthesized in the following
`
`manner: “Dicarboxylic acid (0.064 mol.) was refluxed with 10 ml. of
`
`10
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`

`

`IPR2015-01838
`Patent 8,865,921 B2
`
`anhydrous methanolin a benzene solution with one or two drops of
`
`concentrated sulfuric acid for several hours,” and “[a]fter the removal of the
`
`excess methanol, the residual dimethyl ester was recrystallized from a
`
`suitable solvent several times to give the correct melting point.” Jd. at
`
`1249. This method yielded 68.7% dimethyl! 2,5-furandicarboxylate. Jd.
`
`6. Partenheimer (Ex. 1003)’
`
`Partenheimeris cited and discussed in the background section of the
`
`°921 patent. Ex. 1001, 1:55—2:6. Partenheimer describes synthesis of 2,5-
`
`diformylfuran and FDCA bycatalytic air-oxidation of HMF. Ex. 1003, 102
`
`(Title). Specifically, Partenheimer teaches synthesis of FDCA by contacting
`
`HMF in the presence of Co/Mn/Brcatalysts Co, and with an air pressure of
`
`70 bar at temperatures up to 125°C. Id. at 105 (Table 3).
`
`According to Partenheimer, the advantages of the oxidation process
`
`described therein are 1) “that the catalyst is composed of inexpensive,
`
`simple metal acetate salts and a source of ionic bromide (NaBr, HBr,etc.),”
`
`7 Partenheimeret al., Synthesis of2, 5-Diformylfuran and Furan-2, 5-
`Dicarboxylic Acid by Catalytic Air-Oxidation of5-Hydroxymethylfurfural.
`Unexpectedly Selective Aerobic Oxidation ofBenzyl Alcoholto
`Benzaldehyde with Metal/Bromide Catalysts, 343 ADV. SYNTH. CATAL. 102—
`111, Published Online on Feb. 6, 2001 (Ex. 1003) (““Partenheimer’’).
`Although Partenheimerdid not form the basis for the specific patentability
`challenges upon which weinstituted trial, both Petitioners and Patent Owner
`have relied upon Partenheimer’s teachings to support their respective
`arguments. See Pet. 15—16; PO Resp.3, 8, 10, 20, 26-28; Reply 7, 10-12,
`19. We, therefore, consider Partenheimeras relevant “background”art in
`our evaluation of Petitioners’ patentability challenges. See Ariosa
`Diagnostics v. Verinata Health, Inc., 805 F.3d 1359, 1365 (Fed. Cir. 2015)
`(“Art can legitimately serve to document the knowledgethat skilled artisans
`would bring to bear in reading the prior art identified as producing
`obviousness.”).
`
`11
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`IPR2015-01838
`Patent 8,865,921 B2
`
`2) “[t]he reaction times are within a few hoursat easily accessible
`
`temperatures,” and 3) “[t]he acetic acid solvent is inexpensive and nearly all
`
`alcohols are highly soluble in it.” Jd. at 106. Partenheimer teachesthat the
`
`reactions are performedat air pressure of 70 bar and cautionsthat “[t]he use
`
`of high pressures and the use of dioxygen/nitrogen mixturesis potentially
`
`explosive and dangerous,” and “should be performed only with adequate
`
`barriers for protection.” Jd. at 110.
`
`C. Level of Ordinary Skill in the Art
`
`Petitioners’ expert Dr. Martin opinesthat “one of ordinary skill in the
`
`art of oxidation of aromatic compounds, such as furan based compounds,is
`
`a person with a doctorate degree in chemistry and/or chemical engineering
`
`and havingat least 5 years of experience in oxidation catalysis and chemical
`
`process development.” Ex. 1009 § 14. Patent Owner contends that a person
`of ordinary skill in the art (“POSA”or “skilled artisan”) for the 921 patent
`
`would have had “at least a bachelor’s degree in chemistry or chemical
`
`engineering, having workedin the field of chemical process developmentfor
`
`at least five years and having experience in the preparation of furan
`
`compounds from biomassandin the catalysis of oxidation of furan
`
`compoundsfor a similar period.” PO Resp. 14 (citing Ex. 2003 4 44). In its -
`
`Reply, Petitioners contend that Patent Owner’s proposedlevel of skill in the
`
`art places too many limitations, “whereas Petitioner’s hypothetical POSA —
`
`as defined by Dr. Martin — would have the knowledge and experience to
`
`understand that catalyst concentration is a result-effective variable that
`
`impacts yield.” Reply 2 (citing Ex. 1028 4 7).
`
`12
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`IPR2015-01838
`Patent 8,865,921 B2
`
`Although we do not discern a significant difference between the
`
`qualifications for a skilled artisan proposed by the parties, we determine that
`
`Patent Owner’s proposedlevel of skill in the art is more appropriate for our
`
`analysis. Specifically, we determine that a skilled artisan need not have a
`
`doctorate degree. Patent Owner’s expert, Dr. Wayne P. Schammell, Ph.D.,
`
`states that in his experience “individuals workingin the field often have BS
`
`or MSdegrees with relevant experiencein the field.” Ex. 2003 9 44. At his
`
`deposition, Dr. Martin acknowledgedthat a chemist with a master’s degree
`
`could be a skilled artisan “with appropriate experience,” and that one with a
`
`bachelor’s degree that focuses on organic chemistry andat least 10 years of
`
`experience could also be a skilled artisan. Ex. 1027, 112:21-114:1. We
`
`have also taken into accountthe level of skill in the art that is reflected in the
`
`prior art references themselves. See Okajima v. Bourdeau, 261 F.3d 1350,
`
`135 (Fed. Cir. 2001). With regard to Petitioners’ contention as to whether a
`
`skilled artisan would have the knowledge and experience to understand
`
`whethera catalyst concentration is a result-effective variable (Reply 2), we
`
`determine that issue is more appropriately consideredas part of the
`
`substance of the obviousness analysis rather than our determination of the
`
`appropriate skill level for the ’921 patent.
`
`D. Analysis ofPetitioners’ Patentability Challenges
`
`Petitioners contend that claims 1-5 are obvious based on the teachings
`
`of the ’732 publication in combination with RU °177 and the ’318
`
`application. Pet. 27-40. Petitioners additionally contend that claims 7-9 are
`
`obvious over the combination of the ’732 publication, RU ’177, and the ’318
`
`application in further view of Lewkowski and Oae. Id. at 45-49.
`
`13
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`

`IPR2015-01838
`Patent 8,865,921 B2
`
`Independent claim 1 requires the preparation of FDCA bycontacting a
`feed comprising HMF,or certain derivatives of HMF, with an oxygen-
`
`containing gas in the presence of a Co/Mn/Br oxidation catalyst, and an
`
`acetic acid-based solvent or solvent mixture, at a temperature between 140°C
`
`and 200°C, and at an oxygen partial pressure (pO2) of 1 to 10 bar. Ex. 1001,
`
`7:60-8:6. Independent claim 7 recites the same process of claim 1, and
`
`further recites the additional step of “esterifying the thus obtained product”
`
`in order to produce a dialkyl ester of FDCA. Jd. at 9:1-14. We focus our
`
`analysis on these independentclaims.
`
`In ourInstitution Decision, we determinedthat Petitioners
`
`demonstrated a reasonable likelihood of prevailing with respect to these
`
`obviousness challenges based on the preliminary record at the time and
`
`instituted.trial on that basis. Inst. Dec. 13-15, 18-19. We have now
`
`reconsidered the arguments and evidence presented with the Petition, along
`
`with the additional arguments and evidence presented with Patent Owner’s
`
`Response and Petitioners’ Reply, under the preponderance of the evidence
`
`standard applicable to Final Written Decisions in an inter partes review. 35
`
`.
`U.S.C. § 316(e).
`Asan initial matter, we commenton Petitioners’ attempts to apply the
`
`“prima facie” burden-shifting framework typically applied during patent
`
`examination to argue obviousnessin this proceeding. See, e.g., Pet. 8
`
`(Thus, the claims of the °921 patent are prima facie rendered obviousin
`
`view of the ’732 publication because there is no evidence that reducing the
`
`oxygenpartial pressure by 4.5 bar[] is critical to the methodsor process of
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`oxidizing HMF to FDCA.”); id. at 50 (asserting that “[a] primafacie case of
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`obviousness exists where the claimed rangesandprior art ranges do not
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`overlap but are close enough that one skilled in the art would have expected
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`them to have the same properties”) (citing MPEP § 2144.05); Reply 9
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`(arguing that “[t]his overlap [in temperature] alone supportsa finding of a
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`prima facie case of obviousness.”’); id. at 14-15 (“Because the claimed
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`ranges ‘overlap or lie inside ranges disclosed bythe priorart,’ a primafacie
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`case of obviousness exists.”). Based on the prior art’s disclosure of broader
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`or overlapping ranges, Petitioners seek to shift the burden to Patent Ownerto
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`rebuttheir alleged prima facie case by showing “criticality” with the claimed
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`ranges. See, e.g., Reply 9, 13, 21-23. The Federal Circuit has stated,
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`however, that such a “burden-shifting framework does not apply in the
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`adjudicatory context of an [inter partes review].” In re Magnum Oil Tools
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`Int'l, Ltd., 829 F.3d 1364, 1375 (Fed. Cir. 2016). Rather, “[iJn an inter
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`partes review, the burden of persuasionis on the petitioner to prove
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`‘unpatentability by a preponderance of the evidence,’ 35 U.S.C. § 316(e),
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`and that burden nevershifts to the patentee.” Dynamic Drinkware, LLC vy.
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`Nat'l Graphics, Inc., 800 F.3d 1375, 1378 (Fed. Cir. 2015) (citation
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`omitted).
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`Taking Petitioners’ burden of persuasion into account, wefind that the
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`evidence fails to show it would have been obviousto adjust both the
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`temperature and pO?in the processes taught bythe prior art to within the
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`claimed ranges as a matter of routine optimization. We have also considered
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`Patent Owner’s “objective evidence” concerning unexpected results,
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`satisfaction of a long-felt but unmet need, and copying, but find that
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`evidenceto be less probative in supporting a conclusion of non-obviousness.
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`Nonetheless, based upon our consideration of the record as a whole, we
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`determinethat Petitioners have not established the unpatentability of claims
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`1—5 and 7-9 by a preponderanceof the evidence. We address these issues
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`separately in further detail below.
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`1. Optimization of Temperature to Between 140° and 200°C
`and Oxygen Partial Pressure to Between 1 and 10 Bar
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`Althoughthe prior art disclosed processes with broader or overlapping
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`temperature or pressure ranges, none of the references relied upon by
`Petitioners expressly taught a process in which HMF orits derivatives were
`oxidized to FDCA using a Co/Mn/Brcatalyst at a reaction temperature of
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`between 140°C and 200°C while also maintaining the pO2 between 1 and 10
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`bar as required by the challenged claims of the ’921 patent. Petitioners,
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`therefore, rely upon an “optimization”rationale to assert that the claimed
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`invention would have been obvious. See, e.g., Pet. 9 (“[V]ariations in
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`temperature and pressure are nothing more than the optimization of
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`oxidation conditions explicitly suggested by the ’732 publication...
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`Conducting routine experimentation to determine optimal or workable
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`ranges that produce expected results is suggested to one of ordinary skill in
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`the art by the ’732 publication.”).
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`It is well-established that “where the general conditions of a claim are
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`disclosedin the priorart, it is not inventive to discover the optimum or
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`workable ranges by routine experimentation.” Jn re Aller, 220 F.2d 454, 456
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`(CCPA 1955). However, the parameter to be optimized must have been
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`recognized by thoseskilled in the art to be a “result-effective variable.” In
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`re Antonie, 559 F.2d 618, 620 (CCPA 1977). “While the absence of any
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`disclosure regarding the relationship between the variable and the affected
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`property may precludea finding that the variable is result-effective, the prior
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`art need not provide the exact method of optimization for the variable to be
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`result-effective.” In re Applied Materials, Inc., 692 F.3d 1289, 1297 (Fed.
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`Cir. 2012). Rather, “[a] recognition in the prior art that a property is affected
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`by the variable is sufficient to find the variable result-effective.” Jd.
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`Moreover, where multiple result-effective variables are combined,
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`“Te]vidence that the variables interacted in an unpredictable or unexpected
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`waycould render the combination nonobvious.” Jd. at 1298 (citing KSR
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`Int’l Co. v. Teleflex Inc., 550 U.S. 398, 421 (2007)). Applying these
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`principles, we find that Petitioners have not demonstrated that it would have
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`been a matter of routine experimentation to optimize the reaction
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`temperature and pO: as result-effective variables.
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`Petitioners contend that “the ’732 publication suggested to a person of
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`ordinary skill in the art to vary residence time, temperature and pressure to
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`within the claimed ranges, in order to maximize yield.” Pet. 9. Petitioners
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`assert that the ’732 publication discloses oxidation of HMF to FDCA with
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`Co/Mn/Bror Co/Mn/Zr/Brcatalysts at a temperature range of about 50° to
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`250°C, most preferentially about 50° to 160°C, with a corresponding
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`pressure that keeps the acetic acid solvent mainly in the liquid phase. Jd. at
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`30-31 (citing Ex. 1002, 7:2—5, 4:37-41, 15:7-9; Ex. 1009 ff 20, 86). In
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`particular, Petitioners point to the general disclosure that “[flor preparation
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`of diacid, the preferred temperatures are about 50° to 250°C, most
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`preferentially about 50° to 160°C,” and that “/t/he corresponding pressure
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`is such to keep the solvent mostly in the liquidphase.” Id. at 9 (citing Ex.
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`1002, 7:2-7). Petitioners also point to the examples in the ’732 publication
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`showing reactions of HMF to FDCA at 150°C andat an air pressure of 1000
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`psi. Id. at 31 (citing Ex. 1002, 15-16; Ex. 1009 § 20). As noted by
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`Petitioners, 1000 psi air pressure converts to approximately 14.5 bar pO2
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`whencalculated using ~21% oxygenin air, and to 13.8 bar pOz2 when
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`calculated using 20% oxygenin air. Jd. at 33-34. Petitioners contend that
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`there is no evidence of a “patentable distinction (i.e., criticality) between the
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`claimed pO2 value 1—10 bar (properly construed up to 10.5 bar) and the prior
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`art 13.8 bar pO: practiced in the ’732 publication, especially since the ’732
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`publication relies on reaction pressures for the same reason proffered by the
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`’921 patent,”i.e., “pressure of the reaction mixtureis preferably selected
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`such that the solvent is mainly in the liquid phase.” /d. at 34 (citing Ex.
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`1001, 4:39-41).
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`Patent Ownerarguesthat “[t]he cited prior art describes inefficient,
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`non-commercially viable processes and does not teach or suggest the
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`combination of temperature, oxygen partial pressure and catalyst operating
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`parametersof the ‘921 patent’s invention.” PO Resp. 1. With respect to the
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`732 publication in particular, Patent Ownerasserts that “the ‘732
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`publication’s process is done at higher pressure and the oxidation of HMF is
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`outside the temperature range recited in” the claims. Jd. at 15. We are
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`persuaded by Patent Owner’s arguments and supporting evidence. Although
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`the ’732 publication teaches broadly a preferred temperature range of about
`50° to 250°C (most preferentially about 50° to 160°C), it does not suggest
`specifically keeping the temperature within the narrowerrange recited in
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`claims 1 and 7 (between 140 and 200°C) while also maintaining pO2
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`between 1 and 10 bar. The ’732 publication also teaches that “[t]he
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`preferred time of the reaction is determined by the temperature, pressure and
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`catalyst concentration such that a maximum yield of diacid is obtained.” Ex.
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`1002, 7:5—7. The reference also states that Table 4 “illustrates that
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`increasing catalyst concentrations at a given temperature and time, nearly
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`always increased the [FDCA] yield.” Jd. at 15:9-11. However, contrary to
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`Petitioners’ optimization rationale, we find nothing in the ’732 publication
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`or the other cited prior art to suggest that adjusting both reaction temperature
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`and pO?in the process could have predictably affected FDCAyields.
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`With respect to the claimed oxygenpartial pressure range, we find
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`that the disclosure in the ’732 publication that “corresponding pressureis
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`such to keep the solvent mostly in the liquid phase” (see Ex. 1002, 7:45)
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`would not have led the skilled artisan to optimize pO2 to within the claimed
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`range becauseit relates to the total pressure in the reaction chamberrather
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`than the partial pressure of oxygen, as Dr. Martin confirmed during his
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`deposition. See Ex. 1027 (Martin Depo.), 114:6-115:1. Moreover, the
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`examples of the ’732 publication used a pressure with a significantly higher
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`pO?(i.e., 14.5 bar), suggesting that an overall pressure sufficient to keep the
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`solvent in the liquid phase would not alwaysfall within the claimed pO2
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`range of 1 to 10 bar.
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`Likewise, while the 921 patent also states that “[t]he pressure of the ~
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`reaction mixture is preferably selected such that the solvent is mainly in the
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`liquid phase,”it further states that “[i]n practice this means that pressures
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`between 5 and 100 bar can be used with a preference for pressures between
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`10 and 80 bar.” Ex. 1001, 4:39-43. The ’921 patent also indicates that “[i]n
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`the case of continuously feeding and removing the oxidant gas to and from
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`the reactor, the oxygen partial pressure will be suitably between 1 and 30 bar
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`or more preferably between 1 and 10 bar.” Jd. at 4:51-55. As such, wefind
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`that the desire to keep the solventin the liquid phase that is common to both
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`the ’732 publication and the ’921 patent would not have necessarily required
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`a pObetween | and 10 bar.
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