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. SNEDDEN and
`CHRISTOPHER G. PAULRAJ, Administrative Patent Judges.
`
`PAULRAJ, Administrative Patent Judge.
`
`
`DECISION
`Institution of Inter Partes Review
`37 C.F.R. § 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. SNEDDEN and
`CHRISTOPHER G. PAULRAJ, Administrative Patent Judges.
`
`PAULRAJ, Administrative Patent Judge.
`
`
`DECISION
`Institution of Inter Partes Review
`37 C.F.R. § 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
`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.
`We have jurisdiction under 35 U.S.C. § 314, which provides that an inter
`partes review may not be instituted “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 shown that there is a reasonable
`likelihood that it would prevail with respect to at least one of the challenged
`claims. We thus institute 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 claims priority to a
`provisional application filed on October 7, 2009. See Ex. 1001, Title Page.
`It names Cesar Muňoz De Diego, Matheus Adrianus Dam, and Gerardus
`Johannes Maria Gruter as the inventors. Id.
`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-
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`containing gas in the presence of oxidation catalysts comprising cobalt (Co),
`manganese (Mn), and bromine (Br), and an acetic acid solvent at elevated
`temperatures. Id., Abstract, 1:18–26, 2:39–45. The ’921 patent states that
`“FDCA can be produced in 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.” Id. 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 FDCA with a C1–C5
`alkyl alcohol. Id. at 5:20–41. The ’921 patent acknowledges that the
`esterification of FDCA was known in the prior art. Id. at 5:42–58.
`According to the ’921 patent, FDCA has been identified as a priority
`chemical for establishing a “green” chemistry industry, but no commercial
`process exists for its production. Id. 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 of HMF are
`known to be potential and versatile fuel components and precursors for the
`production of plastics. Id. at 1:44–46. The specification identifies prior art
`processes for the oxidation of HMF to FDCA with Co/Mn/Br catalysts at
`temperatures ranging from 50 to 125oC, which resulted 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. 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
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`determined by the solvent (e.g., acetic acid) pressure at a certain
`temperature.” Id. at 4:34–39. Moreover, the pressure is preferably selected
`to maintain the solvent in the liquid phase, which “means that 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.” Id. 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. Id. at
`4:45–51. The specification further explains that “[t]he temperature of the
`reaction mixture is at least 140° C., preferably from 140 and 200° C., most
`preferably between 160 and 190° C.” Id. at 4:56–58. The specification
`notes that “[g]ood results” were achieved at about 180°C, but cautions that
`“[t]emperatures higher than 180° C may lead to decarboxylation and to other
`degradation products.” Id. at 4:58–61.
`The ’921 patent includes working examples describing experiments in
`which the oxidation reaction was carried out with Co/Mn/Br catalysts 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 bar air pressure, which
`resulted in FDCA yields 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 and 30 bar for 2 hours, showing that FDCA yields under those
`conditions were lower than the results obtained at higher temperature. Id. at
`6:50–62, Table 2.
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`C. Illustrative Claims
`Petitioners challenge claims 1–10 of the ’921 patent. Independent
`claim 1 is illustrative, and reproduced below:
`
`1. A method for 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
`compounds with 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 mixtures is present.
`
`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. The Asserted Grounds of Unpatentability
`Petitioners challenge the patentability of the claims of the ’921 patent
`on the following grounds:
`References
`The ’732 publication,1 RU
`’177,2 and the ’318 application3
`
`Claims challenged
`1–5
`
`Basis
`§ 103(a)
`
`
`1 Grushin et al., WO 01/72732, published Oct. 4, 2001 (Ex. 1002).
`
` 2
`
` Slavinskaya et al., USSR Patent RU-448177A1, published Oct. 30, 1974
`(Ex. 1007, with certified English translation).
`
`3 Lilga et al., US 2008/0103318 A1, published May 1, 2008 (Ex. 1008).
`
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`References
`The ’732 publication, the ’018
`Patent,4 RU ’177, and the ’318
`application
`The ’732 publication,
`Lewkowski,5 Oae,6 RU ’177,
`and the ’318 application
`RU ‘177
`
`Partenheimer,7, the ’732
`publication1, and the ’018
`patent4
`
`
`II. DISCUSSION
`
`A. Claim Construction
`
`Basis
`§ 103(a)
`
`§ 103(a)
`
`§ 103(a)
`
`§ 103(a)
`
`Claims challenged
`6 and 10
`
`7–9
`
`
`1
`
`1–4
`
`We interpret 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
`
`
`4 Sanborn, US 8,558,018 B2, issued Oct. 15, 2013 (Ex. 1004).
`
`5 Lewkowski, Synthesis, Chemistry and Applications of 5-
`Hydroxymethylfurfural and its Derivatives, ARKIVOC 2001 (i) 17-54,
`Published Online on Aug. 8, 2001 (Ex. 1005).
`
`6 Oae et al., A Study of the Acid Dissociation of Furan- and
`Thiophenedicarboxylic Acids and of the Alkaline Hydrolysis of Their Methyl
`Esters, SOC. JPN. 1965, 38, Aug. 1965, at 1247 (Ex. 1006).
`
`7 Partenheimer et al., Synthesis of 2, 5-Diformylfuran and Furan-2, 5-
`Dicarboxylic Acid by Catalytic Air-Oxidation of 5-Hydroxymethylfurfural.
`Unexpectedly Selective Aerobic Oxidation of Benzyl Alcohol to
`Benzaldehyde with Metal/Bromide Catalysts (Ex. 1003).
`
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`interpretation standard in enacting the AIA,”8 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 (U.S. 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. 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 broader definition.”
`In re Bigio, 381 F.3d 1320, 1325 (Fed. Cir. 2004). “Although an inventor is
`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).
`We determine that no explicit construction of any claim term is
`necessary to determine whether to 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”).
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`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,
`2:17–20.9 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.” Id. at 6:22–24. Acetic acid is identified as a preferred
`solvent because FDCA is insoluble in it, thereby facilitating purification. Id.
`at 9:14–21.
`The ’732 publication explains further that “[f]or preparation of diacid,
`the preferred temperatures are about 50o to 250oC, most preferentially about
`50o to 160oC,” and “[t]he corresponding pressure is such to keep the solvent
`mostly in the liquid phase.” Id. 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 good yields
`of FD[C]A.” Id. 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.” Id. 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 FDCA yield
`reported is 59%, obtained at 105° C.” Ex. 1001, 1:48–50.
`
`
`
`
`9 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.
`We also refer herein to the page numbers added to the very bottom of the
`exhibit (e.g., “Petitioners’ Exhibit 1002, Page 2 of 23”).
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`2. RU ’177 (Ex. 1007)
`RU ’177 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 [5MF] is
`subject to oxidation and mixed valance metal salts, such as a mixture of
`cobalt acetate and manganese acetate, as well as bromine-containing
`compounds, such as ammonium bromide, in the aliphatic carboxylic acid
`solution are used as a catalyst.” Id. at 2, col. 4 (cl. 1). RU ’177 further
`discloses that oxidation is “typically conducted under 115-140°C and air
`pressure of 10-15 atm.” Id. at 1, col. 1. RU ’177 specifies the use of acetic
`acid solution as the solvent. Id. 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 compound and catalysts [and] the method is 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 ¶3. More
`specifically, the ’318 application teaches that “[t]he starting material
`comprising HMF is provided into a reactor and at least one of air or O2 is
`provided as oxidant.” Id. ¶ 50. The ’318 application indicates that,
`depending upon the 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
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`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.” Id. ¶ 55. In Example 1, 98% FDCA selectivity was achieved
`using a Pt/ZrO2 catalyst under conditions of 150 psi pressure and 100°C
`temperature. Id. ¶¶ 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(III) 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 “FDCA is a difficult product to handle,” the ’018 patent
`indicates that an FDCA precursor that is easy to separate and subsequently
`converted to FDCA in a different reaction would be beneficial. Id. 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,”10 and
`“oxidation of [5-alkoxymethylfurfurals] can also readily be achieved using
`the same catalyst as used for oxidizing HMF.” Id. at 4:23–33. The ’018
`patent further explains that “[t]he major resulting product is surprisingly
`
`
`10 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.
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`found to 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:
`
`
`
`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 FDCA is highly insoluble.” Id. at 5:10–
`12. When FDCA is ultimately the desired product, this ester derivative can
`be further oxidized to provide FDCA. Id. 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),
`manganese acetate (0.13 g), and sodium bromide (0.11 g) that was subjected
`to 500 psi oxygen at 100°C for 2 hours. Id. at 12:9–13. This resulted in a
`54% molar yield of FDCA. Id. at 12:13–16.
`5.
`Lewkowski (Ex. 1005)
`Lewkowski discusses the methods of synthesis of FDCA, and its
`chemistry and application. Ex. 1005, 17. Lewkowski states “[t]he synthesis
`of diethyl ester and dimethyl ester . . . have been reported.” Id. at 44.
`Lewkowski cites Oae (Ex. 1006) for the synthesis process of dimethyl ester.
`Id. Lewkowski discloses that the diethyl ester of FDCA has “a strong
`anaesthetic action similar to cocaine,” and that another ester form of
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`FDCA—dicalcium 2,5-furandicarboxylate—was shown to have antibacterial
`activity. Id. at 45.
`
`Oae (Ex. 1006)
`6.
`Oae relates to the acid dissociation of furandicarboxylic acids and the
`alkaline hydrolysis of their methyl esters. Ex 1006, 1247. Specifically,
`Oae states 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 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.” Id. at
`1249. This method yielded 68.7% dimethyl 2,5-furandicarboxylate. Id.
`7.
`Partenheimer (Ex. 1003)
`Partenheimer describes synthesis of 2,5-diformylfuran and FDCA by
`catalytic air-oxidation of HMF. Ex. 1003, 102 (Title). Specifically,
`Partenheimer teaches synthesis of FDCA by contacting HMF in the presence
`of Co/Mn/Br catalysts Co, and with an air pressure of 70 bar at temperatures
`up to 125o 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.),”
`2) “[t]he reaction times are within a few hours at easily accessible
`temperatures,” and 3) “[t]he acetic acid solvent is inexpensive and nearly all
`alcohols are highly soluble in it.” Id. at 106. Partenheimer teaches that the
`reactions are performed at air pressure of 70 bar and cautions that “[t]he use
`of high pressures and the use of dioxygen/nitrogen mixtures is potentially
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`explosive and dangerous,” and “should be performed only with adequate
`barriers for protection.” Id. at 110.
`
`C. Analysis of Petitioners’ 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. Id. 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 not relied upon or applied against the claims of the ’921 patent
`and that they have presented new evidence not previously of record. Pet. 27.
`Independent claim 1 requires the preparation of FDCA by contacting 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 140oC and 200oC, 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
`dependent claim 4 specifies that the additional metal is Zr and/or Ce.
`Dependent claim 5 recites that the temperature is between 160° and 190°C.
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`Petitioners assert that the ’732 publication discloses oxidation of HMF
`to FDCA with Co/Mn/Br or Co/Mn/Zr/Br catalysts 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 ¶¶
`20, 86). Petitioners also point to the examples in the ’732 publication
`showing reactions of HMF to FDCA at 150oC and at an air pressure of 1000
`psi. Id. at 31 (citing Ex. 1002, 15–16; Ex. 1009 ¶ 20). As noted by
`Petitioners, 1000 psi air pressure converts to approximately 14.5 bar pO2
`when calculated using ~21% oxygen in air, and to 13.8 bar pO2 when
`calculated using 20% oxygen in air. Id. at 33–34. Petitioners contend that
`there is no evidence of a “patentable distinction (i.e., criticality) between the
`claimed pO2 value 1–10 bar (properly construed up to 10.5 bar) and the prior
`art 13.8 bar pO2 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.” Id. at 34 (citing Ex.
`1001, 4:39–41).
`Petitioners further rely upon RU ’177’s disclosure regarding the
`oxidation of an HMF derivative—5MF—to FDCA in the presence of acetic
`acid and a Co/Mn/Br catalyst, conducted under 115–140°C and air pressure
`of 10–15 atm. Id. at 35 (citing Ex. 1007, 1). Petitioners assert that the
`oxidation conducted according to RU ’177 was at pressures that correlated to
`about 4.26 bar and 6.38 bar pO2, which fell within the claimed range of 1–10
`bar, albeit at lower temperatures. Id. at 36. Petitioners further rely upon the
`’318 application’s teaching of conducting catalytic oxidation of HMF at a
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`preferred temperature of “from 100°C[] through about 160°C.” and a
`pressure of 150–500 psi. Id. at 35 (citing Ex. 1008, ¶ 50). Thus, Petitioners
`assert that the skilled artisan “would have been motivated and enabled to
`lower the pO2 to 1-10 bars based on RU ’177 and ’318, and based on
`standard cost reduction considerations.” Id. (citing Ex. 1009 ¶ 96).
`Based on the record at this stage of the proceeding, we are persuaded
`that Petitioners have shown a 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.11
`Specifically, in the absence of any showing of criticality or unexpected
`results associated with the claimed temperature ranges, we are persuaded by
`Petitioners’ evidence and argument that it would have been obvious for 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 solvent in the
`liquid phase. See In re Aller, 220 F.2d 454, 456 (CCPA 1955)(“[W]here the
`general conditions of a claim are disclosed in the prior art, it is not inventive
`to discover the optimum or workable ranges by routine experimentation.”).
`
`
`11 Because our institution 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 combined teachings of the ’732 publication, the ’018 patent, RU ’177,
`and the ’318 application. Pet. 40–45. Petitioners include a claim chart for
`claim 6. Id. 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 acknowledge that the ’732 patent does not disclose producing
`FDCA from an ester of HMF, but assert that this is suggested by the ’018
`patent. Id. 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 compounds while
`FDCA is highly insoluble. The ester derivatives [can be] further oxidized to
`provide FDCA when FDCA is 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.
`We are 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 shown in
`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 when he states
`“[b]ased on my review of the ’018 patent, it is advantageous to produce
`FDCA from its [i.e., FDCA’s] ester instead of from HMF.” Ex. 1009 ¶ 32
`(emphasis added). An ester of FDCA is not the same as an ester of HMF, as
`also shown by Dr. Martin. Id. ¶¶ 22–23 (providing chemical formulas of 5-
`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 on that teaching. See
`In re Kahn, 441 F.3d 977, 988 (Fed. Cir. 2006) (“[R]ejections on
`obviousness grounds cannot be sustained by mere conclusory statements;
`instead, there must be some articulated reasoning with some rational
`underpinning to support the legal conclusion of obviousness.”), cited in KSR
`Int’l Co. v. Teleflex Inc., 550 U.S. 398, 418 (2007).
`We accordingly determine that Petitioners have not made the requisite
`showing to proceed with an inter partes review based on this challenge.
`
`
`
`17
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`IPR2015-01838
`Patent 8,865,921 B2
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`
`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.
`Independent claim 7 recites identical method steps as claim 1, and
`further includes the step of “esterifying the thus obtained product” in order
`to produce a dialkyl ester of FDCA. Dependent claim 8 recites that the
`product is 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 manner as discussed with respect to
`claim 1 above. With respect to the requirement of 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 Lewkowski and
`Oae as confirmation that esterification of FDCA was known in the prior art,
`and that a motivation to produce dialkyl ester of FDCA would have been its
`“important-anti-bacterial action.” Id. at 47 (citing Ex. 1005, 45).
`Lewkowski further teaches that the “diethyl ester [of FDCA] had a 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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`
`Based on the record at this stage of the proceeding, we are persuaded
`that Petitioners have shown a reasonable likelihood that they would prevail
`in showing the obviousness of claims 7–9 based on this challenge.
`
`4. Obviousness of Claim 1 Based on RU ’177
`Petitioners contend that claim 1 is obvious over RU ’177. Pet. 49–52.
`Petitioners state that “[t]he only difference between claim 1 and the
`teachings of RU ’177 is the reaction temperature,” and “the upper limit of
`the oxidation temperature range disclosed by RU ’177 is close enough to the
`lower limit of the claimed range of 140 to 200ºC.” 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. Id. at 50–51.
`As discussed above, our institution of an inter partes review of claims
`1–5 based on the combination of the ’732 publication, RU ’177, and the ’318
`application, fully encompasses the 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
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`
`5. Obviousness of Claims 1–4 Based on Partenheimer, the ‘732
`Publication, and the ‘018 Patent
`
`Petitioners contend that claims 1–4 are rendered obvious by the
`combined teachings of Partenheimer, the ’732 publication, and the ’018
`patent. Pet. 52–60.
`Partenheimer is discussed in the background section of the ’921
`patent. Ex. 1001, 1:55–2:6. Two of the co-authors of Partenheimer are
`named as inventors of the ‘732 publication, and the references contain
`similar disclosures regarding the oxidation of HMF to produce FD
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