’ FORM 5. Petition for Review or Notice of Appeal of an Order or Decision of an AGENCY, BOARD,
`COMMISSION, OFFICE OR BUREAU
`
`Form 5
`Rev. 03/16
`
`UNITED STATES COURT OF APPEALS FOR THE FEDERAL CIRCUIT
`
`E. I. DuPont De Nemours and
`Company and Archer-Daniels-
`Midland Company
`
`Petitioner or Appellant,
`
`PETITION FOR REVIEW
`
`Furanix Technologies B.V.
`
`Respondentor Appellee.
`
`E. J. DuPont De Nemours and Company and
`Archer-Daniels-Midland Company
`
`(nameall parties* bringing the petition or appeal).
`
`(describe
`
`(Address, phone numberand e-mail ofpetitioner, appellant or attorney)
`
`hereby petition/appeal the court for review of the Final Written-Decision, Paper No. 43, IPR2015-01838
`the order or decision and inciude decision number) of the U.S. Patent and Trademark Office
`(mame the agency, board, office or bureau) entered on Mar3, 2017
`(date).
`The order or decision was received on Mar3, 2017
`(date).
`
`/s/ Michael S. Marcus
`Date: May 2, 2017
`é+Ane
`(Signatureof petitioner, appellants
`“3
`—w
`or attorney)
`8
`Blank Rome LLP
`
`1825 Eye Street NW
`
`Washington, DC 20006°
`
`(202) 420-2200, MMarcus@BlankRome.com
`
`*SeeFed. R. App. P. 15 (a) (2)-for-permissible ways of identifying petitioners.
`
`
`COMMISSION, OFFICE OR BUREAU
`
`Form 5
`Rev. 03/16
`
`UNITED STATES COURT OF APPEALS FOR THE FEDERAL CIRCUIT
`
`E. I. DuPont De Nemours and
`Company and Archer-Daniels-
`Midland Company
`
`Petitioner or Appellant,
`
`PETITION FOR REVIEW
`
`Furanix Technologies B.V.
`
`Respondentor Appellee.
`
`E. J. DuPont De Nemours and Company and
`Archer-Daniels-Midland Company
`
`(nameall parties* bringing the petition or appeal).
`
`(describe
`
`(Address, phone numberand e-mail ofpetitioner, appellant or attorney)
`
`hereby petition/appeal the court for review of the Final Written-Decision, Paper No. 43, IPR2015-01838
`the order or decision and inciude decision number) of the U.S. Patent and Trademark Office
`(mame the agency, board, office or bureau) entered on Mar3, 2017
`(date).
`The order or decision was received on Mar3, 2017
`(date).
`
`/s/ Michael S. Marcus
`Date: May 2, 2017
`é+Ane
`(Signatureof petitioner, appellants
`“3
`—w
`or attorney)
`8
`Blank Rome LLP
`
`1825 Eye Street NW
`
`Washington, DC 20006°
`
`(202) 420-2200, MMarcus@BlankRome.com
`
`*SeeFed. R. App. P. 15 (a) (2)-for-permissible ways of identifying petitioners.
`
`
`
`FORM 380. Certificate ofService
`
`Form 30
`Rev, 03/16
`
`UNITED STATES COURT OF APPEALS FOR THE FEDERAL CIRCUIT
`
`
`
`q
`
`CERTIFICATE OF SERVICE
`
`I certify that I served a copy on counsel of record on May2, 2017
`by:
`
`C U.S. Mail
`
`C] Fax
`
`| Hand
`Electronic Means(by E-mail or CM/ECF)
`
`Michael S. Marcus
`
`‘
`
`/s/ Michael S. Marcus
`
`Nameof Counsel
`
`Signature of Counsel
`
`Law Firm
`
`Address
`
`Blank Rome LLP
`
`1825 Eye Street NW
`
`City, State, Zip
`
`Washington, DC 20006
`
`Telephone Number
`
`(202) 420-2200.
`
`Fax Number
`
`202) 420-2201
`
`E-Mail Address
`
`MMarcus@BlankRome.com
`
`
`
`NOTE: For attorneys filing documents electronically, the name of the filer under whose log-in and
`lpassword a document is submitted must be preceded by an "/s/" and typed in the space where the
`signature would otherwise appear. Graphic and otherelectronic signatures are discouraged.
`
`| ResetFields
`
` -
`
`
`
`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 Gwner.
`
`Case IPR2015-01838
`Patent 8,865,921 B2
`
`PETITIONERS’ NOTICE OF APPEAL
`
`
`
`
`
`Pursuant to 35 U.S.C. § 142 and 37 C.F.R. 90.2(a), Petitioners E. I. du
`Pont de Nemours and Company and Archer-Daniels-Midland Company
`(collectively, “Petitioners”) hereby givenotice oftheir appeal under 35 U.S.C.
`§ 141(c) to the United States Court ofAppeals for the Federal Circuit from the
`
`Final Written Decision (Paper 43) issued by the Patent Trial andAppeal Board
`(“the Board”) on March 3, 2017 in the above-captioned proceeding, and from
`
`all other orders, decisions, rulings, and opinions underlyingorrelated to the
`
`Final Written Decision.
`
`In accordance with 37 C.F.R. § 90.2(a)(3)(i1), the expected issues on
`
`appeal include, but are not limited to, the Board’s failure to construe the
`disputed claim terms; its misapplication ofthe law of obviousnessin the
`
`context of overlapping ranges; and its decision that Petitioners did not show by
`
`a preponderanceof the evidence that claims 1-5 and 7-9 of U.S. Patent
`
`8,865,921 B2 are unpatentable as obvious under 35 U.S.C. § 103(a) and any
`
`finding or determination supporting orrelating to that issue, as well as all other
`
`issues decided adversely to Petitioners or not considered in any orders,
`
`decisions, rulings, or opinions.
`This Notice ofAppeal isbeing filed simultaneously withthe Director of
`
`the United States Patent and Trademark Office, the Board, and the Clerk’s
`
`
`
`Office for the United States Court of Appeals for the Federal Circuit.
`
`Dated: May 2, 2017
`
`/Michael S. Marcus/
`
`By:
`Michael S. Marcus
`Registration No.: 31,727
`Dipu.A. Doshi
`Registration No.: 60,073
`Jonathan W.S. England
`Registration No.: 71,223
`BLANK ROME LLP
`1825 Eye Street, NW
`Washington, DC 20006-5403
`(202) 420-2200
`Attorneys for Petitioners
`
`
`
`‘CERTIFICATE OF FILING
`
`Pursuant to 37 C.F.R. § 104.2, the undersigned certifies that, in addition to
`
`being filed electronically through the Patent Trial and Appeal Board End to End
`system, theoriginal version ofthe foregoing PETITIONERS’ NOTICE OF
`APPEAL-was filed with the Director ofthe United States Patent and Trademark
`
`Office at the following address:
`
`‘
`
`Director of the United States Patent and Trademark Office
`
`c/o Office of the General Counsel
`
`Madison Building East, 10B20
`
`600 Dulany Street
`
`Alexandria, Virginia
`
`The undersigned also certifies that a copy of the foregoing PETITIONERS’
`
`NOTICE OF APPEAL,andthe filing fee, were filed with the Clerk’s Office for
`
`the United States Court of Appeals for the Federal Circuit via CM/ECF.
`
`
`
`CERTIFICATE OF FILING
`
`The undersignedcertifies that a copy of the foregoing PETITIONERS’
`
`NOTICE OF APPEAL is being served on counsel of record by electronic mail.
`
`Dated: May 2, 2017
`
`/Jonathan W.S. England/
`
`By:
`Jonathan W.S. England
`Registration No.: 71,223
`BLANK-ROME LLP
`1825 Eye Street, NW
`Washington, DC 20006-5403
`(202) 420-2200
`Attorney for Petitioner
`
`
`
`EXHIBIT 1
`
`
`
`Trials@uspto.gov
`571-272-7822
`
`Paper No. 43
`Entered: March 3, 2017
`
`UNITED STATES PATENT AND FRADEMARK OFFICE
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`E. I. DU PONT DE NEMOURS AND COMPANY AND
`ARCHER-DANIELS-MIDLAND COMPANY,
`Petitioners,
`
`V.
`
`FURANLX TECHNOLOGIESB.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.
`
`FINAL WRITTEN DECISION
`35 US.C. § 318(a) and 37 CFR. § 42.73
`
`
`
`‘ IPR2015-01838
`Patent 8,865,921 B2
`
`I.
`
`INTRODUCTION
`
`E. E. 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 notfile a Preliminary Response.
`Wehave jurisdiction under 35 U.S.C. § 314, which provides that an inter
`partes review may notbeinstituted “unless .
`.
`. there is a reasonable
`likelihoodthat the petitioner would prevail with respectto at least 1 of the
`claims challenged in the petition.” We determined that the information
`presented in the Petition demonstrated that there was a reasonable likehhhood
`that Petitioners wouldprevail in challenging claims 1-5 and 7—9 as
`unpatentable under 35 U.S.C. § 103(a). Pursuant to-35 U.S.C. § 314, the
`Boardinstituted trial on March 9, 2016, as to those claims ofthe ‘977 Patent.
`
`Paper 10 (“Institution Decision”; “Inst. Dec.”). We denied Petitioners’
`request for rehearing of our decision-to deny institution 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 aReply to Patent
`Owner’s Response. Paper 29 (“Reply”). An oral hearing was held on
`November16, 2016. The transcript ofthe 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 preponderanceofthe.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 notidentified any separate related matters under 42
`C.F.R. § 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 forpreparing 2, 5-furan
`dicarboxylic acid (FDCA), or a dialkyl ester of FDCA,by contacting 5-
`hydroxymethylfurfural (HME), and/or derivativesthereof, 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. Id., Abstract, 1:18-26, 2:39-45. The
`°921 patent states that “FDCA can be producedin particular from esters of
`HME,suchas for example 5-acetoxymethylfurfural (AMF) or a mixture of
`one or more of thesé 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 accordingto 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
`acknowledges that the esterification ofFDCA 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. Id. at 1:34-38. The.specification states.
`that FDCA, a furan derivative, is often synthesized inthe laboratory from
`HME obtained from carbohydrate containing sources such-as glucose,
`fructose, sucrose, and starch. Id. at 1:30-43. The derivatives of HME are
`known to bepotential and versatile fuel components and precursors for the
`production ofplastics. Jd. 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, 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 explainsthat “[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.” Id. 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.” Jd. 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-containinggas 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 explains that“[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.” Id. at 4:56-58. The specification
`notes that “Eg]ood results” were achieved at about 180°C,but cautions that
`“It]emperatures higher than 180° C may lead to decarboxylation andto 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 a Co/Mn/Brcatalystat 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 HME and/or AMF at 180°C for 1 hour with 20 bar air 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. /d. at
`
`6:50-62, Table 2.
`
`C. Illustrative Claims
`
`Claims 1-5 and 7-6 are challengedin this inter partes review.
`
`Independent claim1isillustrative, and reproduced below:
`
`1. A methodforthe 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
`(“MF”), an ester of 5S-hydroxymethylfurfural, 5-methylfurfural, 5-
`(chloromethy!)furfural, 5-methylfuroic acid, 5-(chloromethyl)furoic
`acid, 2,5-dimethylfuran and a mixture of two or moreof these
`compounds with an oxygen-containing gas, in the presence of an
`oxidation catalyst comprising both 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
`
`Independentclaim 7 isdirected to the preparation of a dialkyl ester of
`FDCA,and additionally recites the step of “esterifying the thus obtained
`
`product.”
`
`
`
`
`
`§ 103(a)
`
`D. Patentability Challenges
`The following patentability challenges are at issue in this proceeding:
`
`References
`ao ‘Basis _ ~..
`| Claims challenged -
`The °732 publication,‘RU
`mee
`°177,? and the *318 application?
`The °732 publication,
`
`
`Lewkowski,’ Oae,° RU 7177,
`and the °318 application
`
`
`In addition to theteachingsof the references, Petitioners rely upon the
`
`oe
`
`
`
`7-9
`
`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).
`2 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).
`4 Lewkowski, Synthesis, Chemistry and Applicationsof5-
`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 of Their Methyl
`Esters, SOC. JPN. 1965, 38, Aug. 1965, at 1247 (Ex. 1006).
`
`6
`
`
`
`IPR2015-01838
`Patent 8,865,921 B2
`
`fl.
`
`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). Underthe 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 thespecification .
`.
`. when[it] expressly
`disclaim[s] the broaderdefinition.” In re Bigio, 381 F.3d 1320, 1325 (Fed .
`Cir. 2004). “Although an inventor is indeed free to define the specific terms.
`
`used to describehis or her invention, this must be done with reasonable
`
`clarity, 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 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 following priorart in their challenges.
`
`
`
`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.° Thecatalyst 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 insolublein it, thereby facilitating purification. Id.
`
`.
`at 9:14—21.
`The ’732 publication explains furtherthat “[fJor 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 havingthem react with air at 1000 psi (7 MPa) gave goodyields
`
`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 publicationis identified as prior art in the background
`section ofthe °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.
`Wealsorefer herein to the page numbers addedto the very bottem of the
`exhibit (e.g., “Pefitioners’ Exhibit 1002, Page 2 of 23”).
`
`8
`
`
`
`IPR2015-01838
`Patent 8,865,921 B2
`
`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 aprocess
`ef producing FDCAusing 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.” Id. at 2, col. 4 (claim 1). RU°177 also
`includes a claim specifying that the “oxidation is conductedatthe
`temperature of 115—140°C andair pressure of 10—SO atm.” Jd. at 2, col. 4
`(claim 2). RU ’177 further discloses that oxidationis “typically conducted
`under 145-140°C andair pressure of 10-15 atm.” Jd. at 1, col. 1. In
`Example 1 of RU ’177, SMF was reacted at 118°C-and 20 atm ofpressure
`(4.26 bar pO2) for 4.5 hours andthen the temperature was increased to
`130°C and pressure increased to 30 atm (6.38 bar pO2). Id. at 2, col. 3.
`RU °177 states the methoddisclosed therein has a numberof
`advantages,i.e., “it utilizes readily available and inexpensive reagents as the
`initial compoundandcatalysts [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 7 3. More
`specifically, the °318 application teachesthat“(t]he starting material
`comprising HMF is providedinto a reactor andat least oneofair or Ois.
`- provided as oxidant.” Id. 450. The’318 application indicatesthat,
`
`
`
`IPR2015-01838
`Patent 8,865,921 B2
`
`depending upon the desired reactionrate, the pressure utilized may range
`from atmospheric pressureto the pressure rating of the equipment, and “[a]
`preferred pressure can typically be in the rangeof 150-500 psi.” Id.
`“Similarly an appropriate reaction teraperature can be from about 50° C to
`about 200° C, with apreferred range of from 100° C through about 160° C.”
`
`Ia.
`
`The °318 application states that “underparticular reaction conditions,
`HME conversions of 100% were achieved with selectivity to FDCA as high
`as 98% relative to all other reaction products, intermediates and
`byproducts.” Jd. § 55. In Example 1, 98% FDCA selectivity was achieved
`using a Pt/ZrO> catalyst under conditions of 150 psi pressure and 100°C
`temperature. Id. {{ 67-68.
`4. Lewkowski (Ex. 1005)
`Lewkowski discusses the methodsof 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.” Jd. at 44.
`Lewkowski cites 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,
`Oae states that dimethyl esters of FDCA were synthesized: in the following
`manner: “Dicarboxylic-acid (0:064 mol.) was refluxed with 10 ml. of
`
`10
`
`
`
`IPR2015-01838
`Patent 8,865,921 B2
`
`anhydrous methanolin a benzene sohition 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. Id.
`6. Partenheimer (Ex. 1003)’
`.
`Partenheimeris cited and discussed in-the backgroundsection ofthe
`921 patent. Ex. 1001, 1:55-2:6. Partenheimer describes synthesis of 2,5-
`diformylfuran and FDCAbycatalytic air-oxidation of HMF. Ex. 1003, 102.
`(Title). Specifically, Partenheimer teaches synthesis of FDCA by contacting
`HMEF 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 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 Partenheimeretal., Synthesis of2, 5-Diformylfuran and Furan-2, Jj-
`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 whichweinstitutedtrial, both Petitioners and Patent Owner
`haverelied 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 knowledge that skilled artisans
`would bring to bear in readingthe priorart identified as producing
`obviousness.”).
`
`11
`
`
`
`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 solublein it.” Id. at 106. Partenheimerteaches. thatthe
`reactions are performedat air pressure of 70 bar and-cautionsthat“[t]he use
`of high pressures and the use of dioxygen/nitrogen mixtures is potentially
`explosive and dangerous,” and “should be performed only with adequate
`barriers for protection.” Id. at 110.
`
`C. Level ofOrdinary Skill in the Art
`
`Petitioners’ expert Dr. Martin. opines that “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 having at 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 offuran
`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 manylimitations, “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 { 7).
`
`
`
`IPR2015-01838
`Patent 8,865,921 B2
`
`Although wedonot discern a significant difference between the
`qualifications for a skilled artisan proposed by the parties, we determine that
`Patent Owner’s proposedlevel ofskill in the art is more appropriate for our
`analysis. Specifically, we determinethat 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 working in the field often have BS
`or MS degrees with relevant experience in the field.” Ex. 2003 4 44. At his
`deposition, Dr. Martin acknowledged that a chemist with a master’s degree
`could beaskilled artisan “with appropriate experience,” and that one with a
`bachelor’s degree that focuses on organic chemistry and at least 10 years of
`experience could also be a skilled artisan. Ex. 1027, 112:21-114:1. We
`have also taken into account the level of skill in the art that is reflected in the
`
`prior art references themselves. See Okajima v. Bourdeau, 261 F3d 4350,
`135 (Fed. Cir. 2001). With regard to Petitioners’ contention as to whethera
`skilled artisan would have the knowledge and experience to understand
`whether a catalyst concentration is a result-effective variable (Reply 2), we
`determinethat issue is more appropriately considered as part ofthe
`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 andthe 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
`
`
`
`IPR2015-01838 ©
`Patent 8,865,921 B2
`
`Independent claim 1 requires the preparation of FDCA by contacting a
`feed comprising HMF,orcertain derivatives of HMF, with an oxygen-
`containing gas in the presence of a Co/Mn/Broxidation 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. Independentclaim 7 recites the same process of claim 1, and
`furtherrecites the additional step of “esterifying the thus obtained product”
`in order to produce a dialkyl ester of FDCA. Jd. at 9:1-14. Wefocus our
`analysis on these independent claims.
`.
`In ourInstitution Decision, we determined that Petitioners
`
`demonstrated a reasonable likelihood of prevailing with respect to these
`obviousness challenges based onthe preliminary recordat 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 andPetitioners’ Reply, underthe preponderanceofthe 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 primafacie rendered obviousin
`view of the ’732 publication because there is no evidence that reducing the
`oxygen partial pressure by 4.5 bar[]is critical to the methodsor process of
`oxidizing-HMF to FDCA.”); id. at 50 (asserting that “[a]primafacie case of
`obviousness exists where the claimed ranges andprior art ranges donot
`
`14
`
`
`
`IPR2015-01838
`Patent 8,865,921 B2
`
`overlap but are close enough that one skifledin the art would have expected
`them to have the same properties”) (citing MPEP § 2 144.05); Reply 9
`(arguing that “[tJhis overlap [in temperature] alone supports a finding of a
`primafacie case of obviousness.”); id. at 14-15 (“Because the claimed
`ranges ‘overlap orlie inside ranges disclosed by the priorart,’ a primafacie
`case of obviousness exists.”). Based on thepriorart’s disclosure of broader
`or overlapping ranges,Petitioners seek to shift the burden to Patent Ownerto
`rebut their alleged prima facie case by showing “criticality” with the claimed
`ranges. See, e.g., Reply 9, 13, 21-23. The Federal Circuit has stated,
`however, that such a “burden-shifting framework does not apply in the
`adjudicatory context of an [inter partes review}.” In re Magnum Oil Tools
`Int'l, Ltd., 829 F.3d 1364, 1375-(Fed. Cir. 2016). Rather, “[i]n an inter
`partes review,the*burdenof persuasionis on the petitioner to prove
`‘unpatentability by a preponderanceof the evidence,’ 35 U.S.C. §316€e),
`and that burden nevershifts to the patentee.” Dynamic Drinkware, LLCv.
`Nat'l Graphics, Inc., 800 F.3d 1375, 1378 (Fed. Cir. 2015) (citation:
`
`omitted).
`TakingPetitioners’ burden of persuasion into account, we find that the
`evidence fails to show it would have been obvious to adjust both the
`temperature and pO> in the processestaught by the prior art to within the
`claimed ranges as a matter of routine optimization. We have also considered
`Patent Owner’s “objective evidence” conceming unexpectedresults,
`satisfaction of a long-felt but unmet need, and copying, butfind that
`evidenceto be lessprobative in supporting a conclusion of non-obviousness.
`Nonetheless, based upon ourconsideration ofthe record as a whole, we
`determine that Petitioners have not establishedthe unpatentability of claims
`
`15
`
`
`
`IPR2015-01838
`Patent 8,865,921 B2
`
`1-5 and 7-9 by a preponderanceofthe evidence. We address these issues
`
`separately in further detail below.
`
`1. Optimization ofTemperature to Between 140° and 200°C
`and Oxygen Partial Pressure to Between 1 and 10 Bar
`
`Although the prior art disclosed processes with broaderor overlapping
`temperature or pressure ranges, none ofthe references relied upon by
`Petitioners expressly taught a process in which HME orits derivatives were
`oxidized to FDCA using a‘Co/Mn/Brcatalyst at a reaction temperature of
`between 140°C and 200°C while also maintaining the pO2 between | and 10
`
`bar as required by the challenged claimsof the °921 patent. Petitioners,
`therefore, rely upon an “optimization” rationale to assert that the claimed-
`invention would have been obvious. See, e.g., Pet. 9 (“[V]ariations in
`temperature and pressure are nothing more than the optimization of
`oxidation conditions explicitly suggested by the.’732 publication...
`Conducting routine experimentation to determine optimal or workable
`ranges that produce expectedresults is suggested to one ofordinary skill in
`
`the-art by the ’732 publication.”).
`It is well-established that “where the general conditions of a claim are
`disclosedin the priorart, it is not inventive to discover the optimum or
`workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456
`(CCPA 1955). However, the parameter to be optimized must have been
`recognized bythose skilled in the art to be a “result-effective variable.” Jn
`re Antonie, 559 F.2d 618, 620 (CCPA 1977). ‘While the absence of any
`disclosure regarding the relationship between the variable and the affected
`property mayprecludea findingthat the variable is result-effective,the prior
`art need not provide the exact method ofoptimization for the variable to be
`
`16
`
`
`
`IPR2015-01838
`Patent 8,865,921 B2
`
`result-effective.” In re Applied Materials, Inc., 692 F.3d 1289, 1297 {Fed.
`Cir. 2012). Rather, “{a] recognition in the prior art that a property is affected
`by the variable is sufficient to find the variable result-effective.” Id.
`Moreover, where multiple result-effective variables are combined,
`“elvidence that the variables interacted in an unpredictable or unexpected
`way could render the combination nonobvious.” Jd. at 1298 (citing ASR
`Int’l Co. v. Teleflex Inc., 550 U.S. 398, 421 (2007)). Applying these
`principles, wefind that Petitioners have not demonstrated that itwould have
`been a matter of routine experimentation to optimize the reaction
`temperature and pO>asresult-effective variables.
`Petitioners contend that “the ’732 publication suggested to a person of
`ordinary. skill in the art to vary residence time, temperature and pressure to
`withinthe claim
Accessing this document will incur an additional charge of $.
After purchase, you can access this document again without charge.
Accept $ Charge
Still Working On It
This document is taking longer than usual to download. This can happen if we need to contact the court directly to obtain the document and their servers are running slowly.
Give it another minute or two to complete, and then try the refresh button.
A few More Minutes ... Still Working
It can take up to 5 minutes for us to download a document if the court servers are running slowly.
Thank you for your continued patience.
This document could not be displayed.
We could not find this document within its docket. Please go back to the docket page and check the link. If that does not work, go back to the docket and refresh it to pull the newest information.
Your account does not support viewing this document.
You need a Paid Account to view this document. Click here to change your account type.
Your account does not support viewing this document.
Set your membership
status to view this document.
With a Docket Alarm membership, you'll
get a whole lot more, including:
- Up-to-date information for this case.
- Email alerts whenever there is an update.
- Full text search for other cases.
- Get email alerts whenever a new case matches your search.
One Moment Please
The filing “” is large (MB) and is being downloaded.
Please refresh this page in a few minutes to see if the filing has been downloaded. The filing will also be emailed to you when the download completes.
Your document is on its way!
If you do not receive the document in five minutes, contact support at support@docketalarm.com.
Sealed Document
We are unable to display this document, it may be under a court ordered seal.
If you have proper credentials to access the file, you may proceed directly to the court's system using your government issued username and password.
Access Government Site
