Trials@uspto.gov
`571-272-7822
`
`Paper No. 10
`Entered: March 9, 2016
`
`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 B2
`
`Before TONI R. SCHEINER, SHERIDAN K. SNEDDENand
`CHRISTOPHER G. PAULRAJ, Administrative Patent Judges.
`
`PAULRAJ, Administrative Patent Judge.
`
`DECISION
`Institution of Inter Partes Review
`37 CER. § 42.108
`
`
`571-272-7822
`
`Paper No. 10
`Entered: March 9, 2016
`
`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 B2
`
`Before TONI R. SCHEINER, SHERIDAN K. SNEDDENand
`CHRISTOPHER G. PAULRAJ, Administrative Patent Judges.
`
`PAULRAJ, Administrative Patent Judge.
`
`DECISION
`Institution of Inter Partes Review
`37 CER. § 42.108
`
`
`
`IPR2015-01838
`Patent 8,865,921 B2
`
`I.
`
`INTRODUCTION
`
`E. I. du Pont de Nemours and Company and Archer-Daniels-Midland
`
`Company(collectively, “Petitioners”) filed a Petition (Paper 1, “Pet.”),
`
`requesting institution of an inter partes review of claims 1—10 of
`
`USS. 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 providesthat an inter
`
`partes review maynotbeinstituted “unless .
`
`.
`
`. there is a reasonable
`
`likelihood that the petitioner would prevail with respect to at least 1 of the
`
`claims challenged in the petition.”
`
`Upon consideration of the Petition, and for the reasons explained
`
`below, we determine that Petitioners have shownthatthere is a reasonable
`
`likelihood that it would prevail with respect to at least one of the challenged
`
`claims. Wethusinstitute an inter partes review of claims 1-5 and 7-9 of
`
`the °921 patent.
`
`A.
`
`Related Proceedings.
`
`The Petition does not identify any separate related matters under 42
`
`C.F.R. § 42.8(b)(2). Pet. 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 Mujioz 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, by contacting 5-
`
`hydroxymethylfurfural (HMF), and/or derivatives thereof, with an oxygen-
`
`
`
`IPR2015-01838
`Patent 8,865,921 B2
`
`containing gas in the presence of oxidation catalysts comprising cobalt (Co),
`manganese (Mn), and bromine (Br), and an acetic acid solventat elevated
`temperatures. Jd., Abstract, 1:18-26, 2:39-45. The ’921 patent states that
`“FDCAcan 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,suchas for example from a mixture of AMF
`and HMF.” Jd. at 1:21—24. The ’921 patent further discusses the use of
`
`FDCAobtained according to the process described therein to prepare a
`
`dialkyl ester of 2,5-dicarboxylic acid by the reaction of FDCA with a Ci-Cs
`alkyl alcohol. Jd. at 5:20-41. The ’921 patent acknowledgesthat the
`esterification of FDCA was knownin the prior art. Jd. at 5:42—-58.
`
`According to the ’921 patent, FDCA hasbeenidentified as a priority
`
`chemical for establishing a “green” chemistry industry, but no commercial
`
`processexists 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. Id. at 1:30-43. The derivatives ofHMF are
`knownto be potential and versatile fuel components and precursors for the
`production ofplastics. /d. at 1:44-46. The specification identifies prior art
`processesfor the oxidation of HMF to FDCA with Co/Mn/Brcatalysts 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 improve prior
`art yields by controlling the temperature and/or pressure under which the
`oxidation reaction occurs.
`/d. 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
`
`
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`IPR2015-01838
`Patent 8,865,921 B2
`
`determinedbythe 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 oxygenpartial 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 suppliedat the start
`of the reaction, but this will require a significantly higher pressure. Id. at
`4:45-51. The specification further explains that “[t]he temperature of the
`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
`notesthat “[g]ood results” were achieved at about 180°C, but cautions that
`“It]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 was carried out with Co/Mn/Brcatalysts at an
`
`air pressure ranging from 20-60 bars and temperatures ranging from 100 to
`220°C. Id. at 6:8-11. Moreparticularly, Example 1 describes the oxidation
`of HME and/or AMF at 180°C for 1 hour with 20 bar air pressure, which
`
`resulted in FDCAyields of up to 76.66%. Id. at 6:34—-46, Table 1. Example
`2 provides a comparative example in which AMF oxidation was conducted
`at 100°C and30 bar for 2 hours, showing that FDCAyields under those
`
`conditions were lower than the results obtained at higher temperature. Jd. at
`
`6:50-62, Table 2.
`
`
`
`IPR2015-01838
`Patent 8,865,921 B2
`
`C. Illustrative Claims
`
`Petitioners challenge claims 1-10 of the ’921 patent. 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 5-hydroxymethylfurfural
`(“HMF”),an ester of 5-hydroxymethylfurfural, 5-methylfurfural, 5-
`(chloromethyl)furfural, 5-methylfuroic acid, 5-(chloromethyl)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 comprising both Co and Mn,and further 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.
`Independent claim 7 is directed to the preparation ofa dialkyl ester of
`FDCA,and additionally recites the step of “esterifying the thus obtained
`
`product.”
`
`D. The Asserted Grounds of Unpatentability
`. Petitioners challenge the patentability of the claims of the °921 patent
`on the following grounds:
`
`
`The °732 publication,’ RU-__|
`
`
`°177,? and the °318 application?
`
`§ 103(a)
`
`1-5
`
`
`
`
`
`
`' Grushin et al., WO 01/72732, published Oct. 4, 2001 (Ex. 1002).
`
`2 Slavinskayaet al., USSR Patent RU-448177A1, published Oct. 30, 1974
`(Ex. 1007, with certified English translation).
`
`> Lilga et al., US 2008/0103318 Al, published May1, 2008 (Ex. 1008).
`
`5
`
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`IPR2015-01838
`Patent 8,865,921 B2
`
`
`
`
`
`
`
`
`
`
`The ’732 publication, the 018|§ 103(a) 6 and 10
`Patent,* RU °177, and the ’318
`application
`The ’732 publication,
`Lewkowski,° Oae,® RU 7177,
`and the ’318 application
`
`§ 103(a)
`
`7-9
`
`0
`
`Partenheimer,’, the ’732
`publication’, and the ’018
`
`patent*
`
`§ 103(a)
`
`14
`
`II.
`
`DISCUSSION
`
`A. Claim Construction
`
`Weinterpret claims using the “broadest reasonable construction in
`
`light of the specification of the patent in which [they] appear[].” 37 C.F.R.
`
`§ 42.100(b); see also In re Cuozzo Speed Techs., LLC, 793 F.3d 1268, 1278-
`79 (Fed. Cir. 2015) (“Congress implicitly approved the broadest reasonable
`
`* Sanborn, US 8,558,018 B2, issued Oct. 15, 2013 (Ex. 1004).
`
`> Lewkowski, Synthesis, Chemistry and Applications of5-
`Hydroxymethylfurfural and its Derivatives, ARKIVOC 2001 (i) 17-54,
`Published Online on Aug. 8, 2001 (Ex. 1005).
`
`® Oae etal., 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).
`
`’ 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 (Ex. 1003).
`
`6
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`IPR2015-01838
`Patent 8,865,921 B2
`
`interpretation standard in enacting the AIA,”® and “the standard was
`
`properly adopted by PTO regulation.”), cert. granted, sub nom. Cuozzo
`
`Speed Techs. LLC v. Lee, 84 U.S.L.W. 3218 (US. Jan. 15, 2016) (No. 15-
`
`446). Under the broadest reasonable construction standard, claim terms are
`
`given their ordinary and customary meaning, as would be understood by one
`
`of ordinary skill in the art at the time of the invention. Jn 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 broader definition.”
`
`In 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 reasonableclarity, deliberateness, and precision.” Jn
`
`re Paulsen, 30 F.3d 1475, 1480 (Fed. Cir. 1994).
`
`Wedeterminethat no explicit construction of any claim term is
`
`necessary to determine whetherto institute a trial 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 following prior art in its challenges.
`
`8 The Leahy-Smith America Invents Act, Pub. L. No. 112-29, 125 Stat. 284
`(2011) (“AIA”).
`
`
`
`IPR2015-01838
`Patent 8,865,921 B2
`
`1. 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 “[flor 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.
`
`° 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 added to the very bottom ofthe
`‘exhibit (e.g., “Petitioners’ Exhibit 1002, Page 2 of 23”).
`
`8
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`IPR2015-01838
`Patent 8,865,921 B2
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`2. RU ?177 (Ex. 1007)
`
`RU 7177is 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 usingair 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 (cl. 1). RU °177 further
`
`discloses that oxidationis “typically conducted under 115-140°C andair
`
`pressure of 10-15 atm.” Jd. at 1, col. 1. RU °177 specifies the use of acetic
`
`acid solution as the solvent. Jd. at 1-2, cols. 2-3.
`
`RU °177 states the method disclosed therein has a number of
`
`advantages,i.e., “it utilizes readily available and inexpensive reagents as the
`
`initial compoundand 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
`
`producevarious derivatives, including FDCA. Ex. 1008 43. More
`
`specifically, the °318 application teachesthat “[t]he starting material
`comprising HMF is provided into a reactor andat least one of air or O»is
`provided as oxidant.” Jd. 950. The ’?318 application indicates that,
`
`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.” Id.
`
`“Similarly an appropriate reaction temperature can be from about 50° C to
`
`
`
`IPR2015-01838
`Patent 8,865,921 B2
`
`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 FDCAas high
`
`as 98% relative to all other reaction products, intermediates and
`
`byproducts.” Jd. 4 55. In Example 1, 98% FDCAselectivity was achieved
`using a Pt/ZrO2 catalyst under conditions of 150 psi pressure and 100°C
`
`temperature. Jd. J] 67-68.
`
`4. The ’018 Patent (Ex. 1004)
`
`The ’018 patent discloses a process for the oxidation of furfural
`
`compounds,including HMF,in the presence of dissolved oxygen and a
`
`Co(II), Mn(II), Ce(IID) salt catalyst, wherein the “[t]he products from HMF
`
`can be selectively chosen to be predominantly 2,5-diformylfuran (DFF).. .
`
`or can be further oxidized to [FDCA] by the omission of methyl ethyl ketone
`
`and inclusion of bromide.” Ex. 1004, Abstract.
`
`Because “FDCAis a difficult product to handle,” the 018 patent
`
`indicates that an FDCAprecursorthat is easy to separate and subsequently
`
`converted to FDCAin a different reaction would be beneficial. Jd. at 1:65-
`
`2:4. The ’018 patent states that “[o]ther embodiments of particular interest
`are oxidation of ethers of HMF a.k.a. 5-alkoxymethylfurfurals,”!° and
`
`“oxidation of [5-alkoxymethylfurfurals] can also readily be achieved using
`
`the same catalyst as used for oxidizing HMF.” /d. at 4:23-33. The ’018
`
`patent further explains that “[t]he major resulting productis surprisingly
`
`'0 Although the ’018 patent refers to 5-alkoxymethylfurfural as “AMF,”it is
`not to be confused with 5-acetoxymethylfurfural, which is also identified as
`“AMF”in the 921 patent.
`
`10
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`IPR2015-01838
`Patent 8,865,921 B2
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`foundto be ester derivative [of] a 5-(alkoxycarbonyl) furancarboxylic acid
`
`(AcMF)where the alkoxymethyl ether linkage has been oxidized to an ester
`
`and while the furan aldehyde is oxidized to the acid shown”in the reaction
`
`below:
`
`He
`HOC
`
`CH,OH
`
`0,
`HQ
`
`Fractose
`
`ROH,3804
`
`“Thiec.
`
`~ontinved
`“TOVC.1000paiOy
`CoM,NaBs,ACOH,
`
`
`“9
`
`Ro
`
`c5
`
`AME
`
`6
`
`ou
`
`5
`
`)
`(
`ACME
`
`Id. at 4:34-5:9. According to the ’018 patent, “[t]he benefit of the ester
`
`derivative is that unlike FDCA,the ester derivative is readily soluble in a
`
`variety of organic compounds while FDCAis highly insoluble.” Jd. at 5:10—
`
`12. When FDCAis ultimately the desired product, this ester derivative can
`
`be further oxidized to provide FDCA.
`
`/d. at 5:12-15.
`
`Example 15 of the ’018 patent describes a reaction mixture containing
`
`acetoxymethylfurfural (5.0 g), acetic acid (50 mL), cobalt acetate (0.13 g),
`
`manganeseacetate (0.13 g), and sodium bromide (0.11 g) that was subjected
`
`to 500 psi oxygen at 100°C for 2 hours. Jd. at 12:9-13. This resulted in a
`
`54% molar yield of FDCA.
`
`/d. at 12:13-16.
`
`J.
`
`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.
`
`Lewkowski cites Oae (Ex. 1006) for the synthesis process of dimethylester.
`
`Id. Lewkowskidiscloses that the diethyl ester of FDCA has “a strong
`
`anaesthetic action similar to cocaine,” and that another ester form of
`
`11
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`IPR2015-01838
`Patent 8,865,921 B2
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`FDCA—dicalcium 2,5-furandicarboxylate—was shownto haveantibacterial
`
`activity. Id. at 45.
`
`6.
`
`Oae (Ex. 1006)
`
`Oae relates 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
`
`anhydrous methanol in a benzenesolution 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.
`
`7.
`
`Partenheimer (Ex. 1003)
`
`Partenheimerdescribes synthesis of 2,5-diformylfuran and FDCA by
`
`catalytic air-oxidation of HMF. Ex. 1003, 102 (Title). Specifically,
`
`Partenheimerteaches 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. Jd. at 105 (Table 3).
`
`According to Partenheimer, the advantagesof 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.),”
`|
`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 solublein 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
`
`12
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`IPR2015-01838
`Patent 8,865,921 B2
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`explosive and dangerous,” and “should be performed only with adequate
`barriers for protection.” Jd. at 110.
`
`C. Analysis ofPetitioners’ Patentability Challenges
`
`1. Obviousness of Claims 1-5. Based on the ’732 Publication,
`Either Alone or Combined with RU ’177, and the ’318
`Application
`
`Petitioners contend that claims 1—5 are obvious based on the teachings
`
`of the ’732 publication, alone or in combination with RU ’177 and the ’318
`
`application. Pet. 27-40. Petitioners include a claim chart for claim 1. Jd. at
`
`39-40. In addition to the teachings of the references, Petitioners also rely
`
`upon the Declaration of Kevin J. Martin, Ph.D. (Ex. 1009) in support of this
`
`challenge. Petitioners acknowledge that the ’732 publication is listed among
`
`the references cited on the front page of the °921 patent, but assert that this
`
`reference was notrelied upon or applied against the claims of the °921 patent
`
`and that they have presented new evidence not previously of record. Pet. 27.
`
`Independentclaim 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 an oxidation catalyst comprising Co and
`
`Mn, a source of bromide, 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. Dependent claim 2 more specifically
`
`recites that the feed comprises HMF and/or esters of HMF. Dependent
`
`claim 3 recites that the oxidation catalyst comprises an additional metal, and
`
`dependentclaim 4 specifies that the additional metal is Zr and/or Ce.
`
`Dependentclaim 5 recites that the temperature is between 160° and 190°C.
`
`13
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`IPR2015-01838
`Patent 8,865,921 B2
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`Petitioners assert that the ’732 publication discloses oxidation of HMF
`
`to FDCA with Co/Mn/Bror Co/Mn/Zr/Brcatalysts at a temperature range of
`
`about 50° to 250°C, most preferentially about 50° to 160°C, with a
`
`corresponding pressure that keeps the acetic acid solvent mainly in the liquid
`
`phase. See Pet. 30-31 (citing Ex. 1002, 7:2—-5, 4:37-41, 15:7-9; Ex. 1009 {ff
`
`20, 86). Petitioners also point to the examples in the ’732 publication
`
`showing reactions of HMF to FDCAat 150°C andat an air pressure of 1000
`
`psi. Jd. at 31 (citing Ex. 1002, 15-16; Ex. 1009 § 20). As noted by
`
`Petitioners, 1000 psi air pressure converts to approximately 14.5 bar pO
`
`when calculated using ~21% oxygenin air, and to 13.8 bar pO2 when
`
`calculated using 20% oxygenin air. Jd. at 33-34. Petitioners contend that
`
`there is no evidenceof a “patentable distinction(i.e., criticality) between the
`
`claimed pO) value 1—10 bar (properly construed up to 10.5 bar) and the prior
`
`art 13.8 bar pO» practiced in the ’732 publication, especially since the ’732
`
`publication relies on reaction pressures for the same reason proffered by the
`
`°921 patent,”i.e., “pressure of the reaction mixture is preferably selected
`
`such that the solvent is mainly in the liquid phase.” Jd. at 34 (citing Ex.
`
`1001, 4:39-41).
`
`Petitioners further rely upon RU °177’s disclosure regarding the
`
`oxidation of an HMF derivative—SMF—to FDCAin the presence ofacetic
`
`acid and a Co/Mn/Brcatalyst, conducted under 115—140°C andair pressure
`
`of 10-15 atm.
`
`/d. at 35 (citing Ex. 1007, 1). Petitioners assert that the
`
`oxidation conducted according to RU °177 wasat pressuresthat correlated to
`
`about 4.26 bar and 6.38 bar pO, which fell within the claimed range of 1-10
`
`bar, albeit at lower temperatures. Jd. at 36. Petitioners further rely upon the
`
`’318 application’s teaching of conducting catalytic oxidation of HMF at a
`
`14
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`IPR2015-01838
`Patent 8,865,921 B2
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`preferred temperature of “from 100°C[] through about 160°C.” and a
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`pressure of 150-500 psi. Jd. at 35 (citing Ex. 1008, 7 50). Thus, Petitioners
`
`assert that the skilled artisan “would have been motivated and enabled to
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`lower the pO» to 1-10 bars based on RU °177 and °318, and based on
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`standard cost reduction considerations.” /d. (citing Ex. 1009 { 96).
`
`Based on the recordat this stage of the proceeding, we are persuaded
`
`that Petitioners have showna reasonable likelihood that they would prevail
`
`in showing that the combination of the ‘732 publication, RU ’177, and the
`
`°318 application renders claims 1—5 of the ’921 patent obvious.!!
`
`Specifically, in the absence of any showing ofcriticality or unexpected
`
`results associated with the claimed temperature ranges, we are persuaded by
`
`Petitioners’ evidence and argumentthat it would have been obviousfor the
`
`skilled artisan to optimize the temperature between 140° and 200°C by
`
`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 in order to reduce costs and to keep the solventin the
`
`liquid phase. See In re Aller, 220 F.2d 454, 456 (CCPA 1955)(“[W]here the
`
`general conditions of a claim are disclosed inthe priorart, it is not inventive
`
`to discover the optimum or workable ranges by routine experimentation.”’).
`
`'l Because ourinstitution of this challenge is based on the combination of
`the ’732 publication, RU ’177, and the ’318 application, we do not reach the
`merits of Petitioner’s alternative obviousness argument based on the ’732
`publication alone. See Pet. 31-34.
`
`15
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`IPR2015-01838
`Patent 8,865,921 B2
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`2. Obviousness of Claims 6 and 10 Based on the ’732
`Publication, the ’018 Patent, RU '177, and the ’318
`Application.
`Petitioners contend that dependent claims 6 and 10 are obvious based
`on the combinedteachingsof the ’732 publication, the ’018 patent, RU °177,
`
`and the ’318 application. Pet. 40-45. Petitioners include a claim chart for
`claim 6. Jd. at 42. Petitioners also rely upon Dr. Martin’s Declaration in
`
`.
`
`support of this challenge.
`
`Claims 6 and 10 both require that the feed comprises an ester of HMF.
`
`Petitioners acknowledgethat the ’732 patent does not disclose producing
`
`FDCAfrom an ester of HMF,but assert that this is suggested by the ’018
`
`patent. Jd. at 41. More specifically, Petitioners rely upon the ’018 patent’s
`
`teaching that “[t]he benefit of the ester derivative is that unlike FDCA,the
`
`ester derivative is readily soluble in a variety of organic compoundswhile
`
`FDCAis highly insoluble. The ester derivatives [can be] further oxidized to
`
`provide FDCA when FDCAis ultimately the desired product.” Pet. 42
`
`(citing Ex. 1004, 5:9-19). Petitioners thus assert that “the ’018 patent
`
`provides both motivation and suggestion to use the acetate ester derivative of
`
`HMF in lieu of HMF to produce FDCA.” Id.
`
`Weare not persuaded that Petitioners have demonstrated a reasonable
`
`likelihood of prevailing with respect to this obviousness challenge. The
`
`“ester derivative” identified in the portion of the 018 patent that Petitioners
`
`cite refers to the ester of FDCA,not the ester of HMF as required by claims
`
`6 and 10 of the 921 patent. This is clear from the reaction scheme shownin
`
`columns 4 and 5 of the ’018 patent, in which an ether of HMF,i.e., 5-
`
`alkoxymethylfurural, is converted to produce an ester of FDCA,i.e., 5-
`
`(alkoxycarbonyl)furancarboxylic acid (AcMFA). Ex. 1004, 4:23-5:9.
`
`16
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`IPR2015-01838
`Patent 8,865,921 B2
`
`There is nothing in that portion of the ’018 patent to suggest that an ester of
`
`HMF,e.g., 5-acetoxymethylfurfural, could be used to form FDCA. Indeed,
`
`Petitioners’ own expert, Dr. Martin, acknowledges as much whenhestates
`
`“{bjased on my review ofthe ’018 patent, it is advantageous to produce
`
`FDCAfrom its [i.e., FDCA’s] ester instead of from HMF.” Ex. 1009 § 32
`
`(emphasis added). An ester of FDCAis not the same as an ester of HMF,as
`
`also shownby Dr. Martin. Jd. § 22-23 (providing chemical formulas of5-
`
`-acetoxymethylfurfural and an “esterified FDCA”).
`
`To be sure, we recognize that Example 15 of the ’018 patent
`
`separately describes the oxidation of acetoxymethylfurural under 500 psi
`
`oxygen (i.e., ~ 34 bar pO2) at 100°C to produce FDCA. Ex. 1004, 12:9-16.
`
`However, other than a single cursory citation to this Example in the Petition
`
`(Pet. 42), Petitioners fail to provide any further explanation as to the
`
`relevance of this teaching to their obviousness contentions. A conclusory
`
`cite to a prior art teaching, without more,is insufficient to demonstrate that
`
`the claimed invention would have been obvious based onthat teaching. See
`
`In re Kahn, 441 F.3d 977, 988 (Fed. Cir. 2006) (“[R]ejections on
`
`obviousness grounds cannotbe sustained by mere conclusory statements;
`
`instead, there must be somearticulated reasoning with somerational
`
`underpinning to support the legal conclusion of obviousness.”), cited in KSR
`
`Int’l Co. v. Teleflex Inc., 550 U.S. 398, 418 (2007).
`
`Weaccordingly determinethat Petitioners have not made the requisite
`
`showing to proceed with an inter partes review based onthis challenge.
`
`17
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`IPR2015-01838
`Patent 8,865,921 B2
`
`3. Obviousness of Claims 7-9 Based on the ’732 Publication,
`Admitted Prior Art, Lewkowski, Oae, RU ’177 and the ’318
`Application
`
`Petitioners contend that claims 7—9 are obvious over the ’732
`
`publication, in view of admitted prior art in the °921 patent, and/or in further
`
`view of Lewkowski, Oae, RU ’177, and the ’318 application. Pet. 45-49.
`
`Petitioners also rely upon Dr. Martin’s Declaration in support of this
`
`challenge.
`
`Independentclaim 7 recites identical method steps as claim 1, and
`
`further includes the step of “esterifying the thus obtained product” in order
`
`to producea dialkyl ester of FDCA. Dependent claim 8 recites that the
`
`productis esterified with a C1—-C5 alkyl alcohol, and dependent claim 9
`
`more specifically recites that the dialkyl ester is the dimethyl ester of FDCA.
`Petitioners rely upon the teachings of the ’732 publication, RU °177,
`and the ‘318 application in the same manneras discussed with respect to
`
`claim 1 above. With respect to the requirementof esterifying FDCA,
`
`Petitioners point to admissions in the ’921 patent that “[t]he esterification of
`
`2,5-furan dicarboxylic acid is known.” Pet. 46 (citing Ex. 1001, 5:20-24,
`
`5:42-48). Petitioners additionally point to the teachings in Lewkowskiand
`
`Oaeas confirmation that esterification of FDCA was knownin thepriorart,
`and that a motivation to produce dialkyl ester of FDCA would have beenits
`
`“{mportant-anti-bacterial action.” /d. at 47 (citing Ex. 1005, 45).
`
`Lewkowski further teaches that the “diethyl ester [of FDCA] hada strong
`
`anaesthetic action similar to cocaine.” Ex. 1005, 45. As such, Petitioners
`
`have demonstrated that the skilled artisan would have had a sufficient reason
`
`to further esterify FDCA.
`
`18
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`IPR2015-01838
`Patent 8,865,921 B2
`
`Based onthe recordat this stage of the proceeding, we are persuaded
`
`that Petitioners have shown a reasonable likelihood that they would prevail
`
`in showingthe obviousness ofclaims 7—9 based onthis challenge.
`
`4. Obviousness of Claim I Based on RU ’177
`
`Petitioners contend that claim 1 is obvious over RU 7177. Pet. 49-52.
`
`Petitioners state that “[t]he only difference between claim 1 and the
`teachings of RU ’177is the reaction temperature,” and “the upperlimit of
`
`the oxidation temperature range disclosed by RU ’177 is close enoughto the
`
`lowerlimit of the claimed range of 140 to 200°C.” Pet. 50 (citing Ex. 1007,
`
`1). Petitioners additionally assert that RU ’177 reported yields that are close
`
`to the yields reported by the ’921 patent, thus demonstrating the lack of any
`
`unexpected results associated with the increased temperature conditions
`
`required for the claims. Jd. at 50-51.
`
`Asdiscussed above,ourinstitution of an inter partes review of claims
`
`1—5 based on the combination of the ’732 publication, RU ’177, and the ’318
`
`application, fully encompassesthe relevant teachings of RU 177 cited for
`
`this challenge. Petitioners, therefore, have not demonstrated a sufficient
`
`basis to proceed on a separate obviousness challenge based on RU °177
`
`alone.
`
`Board rules require us to “secure the just, speedy, and inexpensive
`
`resolution of every proceeding.” 37 C.F.R. § 42.1(b). In view of the
`foregoing, we decline to institute on the basis of this additional obviousness
`challenge in order to conserve Board and party resources and ensure timely
`
`completion of the inter partes review.
`
`19
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`IPR2015-01838
`Patent 8,865,921 B2
`
`5. Obviousness of Claims 1-4 Based on Partenheimer, the ‘732
`Publication, and the ‘018 Patent
`
`Petitioners contend that claims 1—4 are rendered obviousby the
`
`combined teachings of Partenheimer, the ’732 publication, and the ’018
`
`patent. Pet. 52-60.
`Partenheimeris discussed in the backgroundsectionof the ’921
`
`patent. Ex. 1001, 1:55-2:6. Twoof the co-authors of Partenheimerare
`namedas inventors of the ‘732 publication, and the references contain
`
`similar disclosures regarding the oxidation of HMF to produce FDCA.
`
`Partenheimer describes its oxidation process as taking place at temperatures
`up to 125°C,andat pressures of 70 bar (14.5 bar pO2). Ex. 1003, 105 (Table
`3). Partenheimer, however,does not expressly teach temperatures higher
`than 140°C,as required by the claims of the 921 patent. Petitioners have
`not identified any additional teachings of Partenheimer that would render
`claims 1-4 obvious beyond whatis already encompassedbythe challenge
`based on the combination of the ’732 publication, RU °177, and the ’318
`
`application.
`Board rules require us to “secure the just, speedy, and inexpensive
`resolution of every proceeding.” 37 C.F.R. § 42.1(b). In view ofthe
`foregoing, we declineto institute on the basis of this additional obviousness
`challengein order to conserve Board and party resources and ensure timely
`completion of the inter partes review.
`
`Il.
`
`CONCLUSION
`
`For the foregoing reasons, based the information presentedin the
`Petition, we determine that Petitioners have demonstrated that there is a
`
`20
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`IPR2015-01838
`Patent 8,865,921 B2
`
`reasonable
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