`
`
`U.S. Patent No.: 8,865,921
`Petition for Inter Partes Review
`
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`Paper No. ___
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`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
`
`
`U.S. Patent No. 8,865,921
`Issue Date: October 21, 2014
`
`
`Entitled: METHOD FOR THE PREPARATION OF 2,5-
`FURANDICARBOXYLIC ACID AND FOR THE PREPARATION OF
`THE DIALKYL ESTER OF 2,5-FURANDICARBOXYLIC ACID
`
`____________________
`
`Inter Partes Review No.: Unassigned
`____________________
`
`PETITION FOR INTER PARTES REVIEW
`
`
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`

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`
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`TABLE OF CONTENTS
`
`
`Page No.
`
`I.
`
`Mandatory notices ................................................................................................................1
`
`A.
`
`B.
`
`C.
`
`D.
`
`E.
`
`Real Parties-In-Interest Pursuant to 37 C.F.R. § 42.8(b) (1) ...................................1
`
`Related Matters Pursuant to 37 C.F.R. § 42.8(b) (2) ...............................................1
`
`Lead and Back-Up Counsel Pursuant to 37 C.F.R. § 42.8(b) (3) ............................1
`
`Service Information Pursuant to 37 C.F.R. § 42.8(b) (4) ........................................1
`
`Payment of Fees under 37 C.F.R. §§ 42.15(a) and 42.103 ......................................2
`
`Grounds for Standing ...........................................................................................................2
`
`Statement of Precise Relief Requested ................................................................................2
`
`A.
`
`B.
`
`Identification of Claims Challenged ........................................................................2
`
`Statutory Grounds and Patents and Printed Publications Relied Upon for
`Each Ground ............................................................................................................2
`
`II.
`
`III.
`
`1.
`
`2.
`
`3.
`
`4.
`
`5.
`
`6.
`
`International Publication No. WO 01/072732 A2 (“the ’732
`publication” or “’732”) (Exh. 1002). ...........................................................3
`
`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”
`(“Partenheimer”) (Exh. 1003). .....................................................................3
`
`U.S Patent No. 8,558,018 (“the ’018 Patent” or “’018”) (Exh. 1004). ........3
`
`Lewkowski, “Synthesis, Chemistry and Applications of 5-
`Hydroxymethylfurfural and its Derivatives” (“Lewkowski”) (Exh.
`1005). ...........................................................................................................3
`
`Oae et al, “A Study of the Acid Dissociation of Furan- and
`Thiophenedicarboxylic Acids and of the Alkaline Hydrolysis of Their
`Methyl Esters” (“Oae”) (Exh. 1006). ...........................................................3
`
`USSR Patent Publication 448177A1 (“the RU ’177 publication” or
`“RU ’177”) (citations to Certified English Language Translation)
`(Exh. 1007). .................................................................................................3
`
`i
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`

`

`
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`IV.
`
`V.
`
`7.
`
`U.S. Patent Publication No. 2008/0103318 (“the ’318 publication” or
`“’318”) (Exh. 1008). ....................................................................................4
`
`Specific Claims and Ground for Relief ................................................................................4
`
`Statement of Reasons for the Requested Relief ...................................................................5
`
`A.
`
`B.
`
`C.
`
`D.
`
`E.
`
`Brief Summary of Reasons for Relief Requested ....................................................5
`
`The ’921 Patent ......................................................................................................10
`
`Prosecution History of the ’921 Patent ..................................................................12
`
`1.
`
`Flaws in PO’s Analysis and Argument ......................................................15
`
`Prior Art Admissions by the ’921 Patent ...............................................................18
`
`Construction of Claims of the ’921 Patent .............................................................19
`
`1.
`
`2.
`
`3.
`
`4.
`
`5.
`
`6.
`
`7.
`
`8.
`
`Preamble: “for the preparation of 2,5-furan dicarboxylic acid” ................19
`
`Transitional “comprising” and “consisting of” ..........................................20
`
`“hydroxymethylfurfural” and “furan based derivative” ............................22
`
`“an oxygen-containing gas” .......................................................................24
`
`“an oxidation catalyst comprising both Co and Mn” .................................24
`
`“a source of bromine” ................................................................................25
`
`“at an oxygen partial pressure of 1 to 10 bar” ...........................................25
`
`“temperature between 140° C. and 200° C” ..............................................26
`
`F.
`
`Specific Identification of Where Each Element of the Claims is Disclosed in
`Prior Art Patents and Printed Publications .............................................................26
`
`1.
`
`2.
`
`3.
`
`Claims 1-5 of the ’921 patent are obvious over International
`Publication WO 2001/072732, either alone or combined with RU
`’177 and the ’318 publication. ...................................................................27
`
`Claims 6 and 10 of the ’921 patent are obvious over the ’732
`publication in view of the ’018 patent, and optionally in view of RU
`’177 and ’318. ............................................................................................40
`
`Claims 7-9 of the ’921 patent are obvious over the ’732 publication in
`view of Applicants Admitted Prior Art, or, in addition or in the
`
`ii
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`alternative, Lewkowski and/or Oae, and optionally in view of RU
`’177 and ’318. ............................................................................................45
`
`4.
`
`5.
`
`Claim 1 is obvious over RU ’177 ..............................................................49
`
`Claims 1-4 are obvious over Partenheimer in view of the ’732
`publication combined with or further in view of the’018 patent ...............52
`
`VI.
`
`Conclusion .........................................................................................................................60
`
`
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`
`
`
`
`
`iii
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`
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`CASES
`
`TABLE OF AUTHORITIES 
`
`Page(s)
`
`Bristol-Myers Squibb Co. v. Teva Pharms. USA, Inc., 752 F.3d 967 (Fed. Cir.
`2014) ..................................................................................................................................16, 50
`
`Crystal Semiconductor Corp. v. Tritech Micro, Inc., 246 F.3d 1336 (Fed. Cir.
`2001) ........................................................................................................................................20
`
`Grasselli v. Rohm & Haas Co., 713 F.2d 731 (Fed. Cir. 1983)...........................................6, 17, 19
`
`In re Aller, 220 F.2d 454 (C.C.P.A. 1955).................................................................................9, 54
`
`In re Boesch (cf. MPEP 716.02(b) III). ....................................................................................... 14
`
`In re Cuozzo Speed Techs., LLC, 2014-1301 (Fed. Cir. Feb. 4, 2015) ..........................................19
`
`In re Lukach, 442 F.2d 967 (C.C.P.A. 1971) .................................................................................29
`
`In re Malagari, 499 F.2d 1297 (C.C.P.A. 1974) ...............................................................34, 38, 56
`
`In re Skoll, 523 F.2d 1392 (C.C.P.A. 1975)...................................................................................29
`
`Titanium Metals Corp. of Amer. v Banner, 778 F.2d 775 (Fed. Cir. 1985) ........................... passim
`
`Vehicular Techs. v Titan Wheel Int’l, Inc., 212 F.3d 1377 (Fed. Cir. 2000) .................................20
`
`STATUTES
`
`35 U.S.C. ..........................................................................................................................................4
`
`35 U.S.C. § 102 ..................................................................................................................12, 35, 46
`
`35 U.S.C. § 102(b) ...................................................................................................................26, 52
`
`35 U.S.C. §§ 102(b) and 102(e) .......................................................................................................3
`
`35 U.S.C. § 102(e) ...........................................................................................................................4
`
`35 U.S.C. § 103 ..........................................................................................................................2, 38
`
`35 U.S.C. § 112 ................................................................................................................................4
`
`35 U.S.C. §§ 311-318 ......................................................................................................................2
`
`iv
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`35 U.S.C. § 312(a) (3) ......................................................................................................................3
`35 U.S.C. § 312(a) (3) .................................................................................................................... ..3
`
`FDCA ..................................................................................................................................... passim
`FDCA ................................................................................................................................... .. passim
`
`REGULATIONS
`REGULATIONS
`
`37 C.F.R. § 42.8(b) (1) .....................................................................................................................1
`37 C.F.R. § 42.8(b) (1) ................................................................................................................... ..1
`
`37 C.F.R. § 42.8(b) (2) .....................................................................................................................1
`37 C.F.R. § 42.8(b) (2) ................................................................................................................... ..1
`
`37 C.F.R. § 42.8(b) (3) .....................................................................................................................1
`37 C.F.R. § 42.8(b) (3) ................................................................................................................... ..1
`
`37 C.F.R. § 42.8(b) (4) .....................................................................................................................1
`37 C.F.R. § 42.8(b) (4) ................................................................................................................... ..1
`
`37 C.F.R. § 42.10(b) ........................................................................................................................1
`37 C.F.R. § 42.10(b) ...................................................................................................................... ..1
`
`37 C.F.R. §§ 42.15(a) and 42.103 ....................................................................................................2
`37 C.F.R. §§ 42.15(a) and 42.103 .................................................................................................. ..2
`
`37 C.F.R. § 42.65 .............................................................................................................................5
`37 C.F.R. § 42.65 ........................................................................................................................... ..5
`
`37 C.F.R. §§ 42.100-42.123 .............................................................................................................2
`37 C.F.R. §§ 42.100-42.123 ........................................................................................................... ..2
`
`37 C.F.R. § 42.100(b) ....................................................................................................................19
`37 C.F.R. § 42.100(b) .................................................................................................................. ..19
`
`37 C.F.R. § 42.104(b) ......................................................................................................................2
`37 C.F.R. § 42.104(b) .................................................................................................................... ..2
`
`
`
`
`
`
`v
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`

`
`
`LISTING OF EXHIBITS
`
`
`Exhibit 1001: U.S. Patent No. 8,865,921 B2 (filed Oct. 6, 2010).
`International Application Publication WO 01/072732 A2 (filed
`Mar. 27, 2001).
`Walt 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, ADV. SYNTH. CATAL. 2001, 343, NO. 1, Published
`Online on Feb. 6, 2001.
`Exhibit 1004: U.S. Patent No. 8,558,018 B2 (filed May 14, 2010).
`Jaroslaw Lewkowski, Synthesis, Chemistry and Applications of 5-
`Hydroxymethylfurfural and its Derivatives, ARKIVOC 2001 (i)
`17-54, Published Online on Aug. 8, 2001.
`Shigeru 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.
`Exhibit 1007: USSR Patent RU-448177A1 (filed Oct. 30, 1972) (cited to
`Certified English Language Translation).
`Exhibit 1008: U.S. Patent Publication No. US 2008/0103318 (filed Oct. 31,
`2007).
`
`Exhibit 1002:
`
`Exhibit 1003:
`
`Exhibit 1005:
`
`Exhibit 1006:
`
`Exhibit 1009: Declaration of Dr. Kevin J. Martin.
`
`Exhibit 1010:
`
`Prosecution History of European Patent Application No. 2 486
`028 A0 (filed Oct. 7, 2009).
`Prosecution History of U.S. Patent No. 8,865,921 B2.
`Exhibit 1011:
`Exhibit 1012: Brian S. Furniss et al., VOGEL’S TEXTBOOK OF PRACTICAL
`ORGANIC CHEMISTRY (5th ed. 1989).
`Exhibit 1013: U.S. Patent No. 2,628,249 (filed Jan. 3, 1951).
`D.R. Kreile et al., Liquid-Phase Catalytic Oxidation of 5-
`Methylfurfural, Zhurnal Vsesoyuznogo Khimicheskogo
`Obshchestva, Vol. 22, 1977.
`CV of Dr. Kevin J. Martin.
`
`Exhibit 1014
`
`Exhibit 1015
`
`vi
`
`
`
`

`

`Exhibit 1018
`
`Exhibit 1020
`
`
`
`Exhibit 1016
`
`International Application Publication WO 2007/146636 A1 (filed
`June 4, 2007).
`Exhibit 1017 U.S. Patent No. 3,071,599 B2 (filed Feb. 25, 1959).
`B. F. M. Kuster, 5-Hydroxymethylfurfural (HMF). A Review
`Focusing on its Manufacture, Starch/ Stärke, 42, 1990, at 314.
`Exhibit 1019 G.B. Patent Specification No. 621,971 (filed Nov. 12, 1946).
`Claude Moreau et al., Recent Catalytic Advances in the Chemistry
`of Substituted Furans from Carbohydrats and in the Ensuing
`Polymers, Topics in Catalysis Vol. 27, Nos. 1-4, Feb. 2004, at 11.
`Exhibit 1021 MCGRAW-HILL ENCYCLOPEDIA OF CHEMISTRY, (Sybil P. Parker et
`al. eds., 5th ed. 1983).
`Exhibit 1022 U.S. Patent Publication No. 2009/0156841 (filed Dec. 12, 2008).
`Exhibit 1023 U.S. Patent No. 4,792,621 (filed Jul. 28, 1986).
`Exhibit 1024 HAWLEY’S CONDENSED CHEMICAL DICTIONARY (13th ed. 1997 at
`92).
`Exhibit 1025 U.S. PATENT NO. 5,099,064 (FILED MAR. 24, 1992).
`Exhibit 1026 KIRK-OTHMER ENCYCLOPEDIA OF CHEMICAL TECHNOLOGY,
`(Jacqueline I. Kroschwitz et al. eds., 4th ed. vol. 18, 1996).
`
`vii
`
`
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`

`

`
`
`I. MANDATORY NOTICES
`
`A. Real Parties-In-Interest Pursuant to 37 C.F.R. § 42.8(b) (1)
`
`E. I. du Pont de Nemours and Company and Archer-Daniels-Midland-
`
`Company (“Petitioners”) are the real parties-in-interest.
`
`B. Related Matters Pursuant to 37 C.F.R. § 42.8(b) (2)
`
`Records of the U.S. Patent and Trademark Office (“PTO”) indicate that U.S.
`
`Patent No. 8,865,921 (“the ’921 patent) (Exhibit 1001) issued on October 21, 2014
`
`from U.S. Patent Application No. 13/497,690 (“the ’690 application”), which
`
`claims the benefit of PCT Application No. PCT/NL2010/050654 (PCT Pub. No.
`
`WO 2011/043661), which claims benefit of U.S. Provisional Application No.
`
`61/249,395.
`
`C. Lead and Back-Up Counsel Pursuant to 37 C.F.R. § 42.8(b) (3)
`
`Petitioner identifies Michael S. Marcus (Reg. 31,727) as Lead Counsel and
`
`Dipu A. Doshi (Reg. No. 60,373) and Jonathan W.S. England (Reg. No. 71,223) as
`
`Backup Counsel. Pursuant to 37 C.F.R. § 42.10(b), a Power of Attorney
`
`accompanies this Petition.
`
`D.
`
`Service Information Pursuant to 37 C.F.R. § 42.8(b) (4)
`
`Lead counsel for Petitioner may be served by electronic mail or mail at:
`
`Michael S. Marcus
`Reg. No. 31,727
`DICKSTEIN SHAPIRO LLP
`1825 Eye Street NW
`
`1
`
`

`

`
`
`Washington, DC 20006
`Tel (202) 420-3702
`Fax (202) 420-2201
`marcusm@dicksteinshapiro.com
`DuPont.IPR@dicksteinshapiro.com
`
`E.
`
`Payment of Fees under 37 C.F.R. §§ 42.15(a) and 42.103
`
`The required fees are submitted herewith. If additional fees are owed during
`
`this proceeding, the PTO is authorized to charge Deposit Account No. 04-1073.
`
`II. GROUNDS FOR STANDING
`
`Petitioners certify that the ’921 patent is available for inter partes review.
`
`Petitioners are not barred or estopped from requesting inter partes review
`
`challenging the patent claims on the grounds set forth herein.
`
`III. STATEMENT OF PRECISE RELIEF REQUESTED
`
`A.
`
`Identification of Claims Challenged
`
`Pursuant to 37 C.F.R. § 42.104(b), Petitioner respectfully requests inter
`
`partes review of claims 1-10 of the ’921 patent under 35 U.S.C. §§ 311-318 and
`
`37 C.F.R. §§ 42.100-42.123, and the cancellation of those claims as being
`
`unpatentable under 35 U.S.C. § 103.
`
`B.
`
`Statutory Grounds and Patents and Printed Publications Relied
`Upon for Each Ground
`
`There is at least a reasonable likelihood that at least one of claims 1-10 of
`
`the ’921 patent will be found obvious based on the following prior art. All of the
`
`prior art patents and printed publications discussed herein constitute prior art
`
`
`
`2
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`

`

`
`
`against the ’921 patent under 35 U.S.C. §§ 102(b) and 102(e), and are submitted
`
`under 35 U.S.C. § 312(a) (3).
`
`1.
`
`International Publication No. WO 01/072732 A2 (“the ’732
`
`publication” or “’732”) (Exh. 1002).
`
`2. 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”
`
`(“Partenheimer”) (Exh. 1003).
`
`3. U.S Patent No. 8,558,018 (“the ’018 Patent” or “’018”) (Exh. 1004).
`
`4. Lewkowski, “Synthesis, Chemistry and Applications of 5-
`
`Hydroxymethylfurfural and its Derivatives” (“Lewkowski”) (Exh.
`
`1005).
`
`5. Oae et al, “A Study of the Acid Dissociation of Furan- and
`
`Thiophenedicarboxylic Acids and of the Alkaline Hydrolysis of Their
`
`Methyl Esters” (“Oae”) (Exh. 1006).
`
`6. USSR Patent Publication 448177A1 (“the RU ’177 publication” or “RU
`
`’177”) (citations to Certified English Language Translation) (Exh.
`
`1007).
`
`
`
`3
`
`

`

`
`
`7. U.S. Patent Publication No. 2008/0103318 (“the ’318 publication” or
`
`“’318”) (Exh. 1008).
`
`U.S. Patent No. 8,558,018 qualifies as prior art under 35 U.S.C. § 102(e) as
`
`it issued from U.S. Application No. 13/319,877, a National Stage filing under 35
`
`U.S.C. § 371 of PCT/US2010/034856 (“PCT ’856”), filed May 14, 2010. The U.S
`
`is a “designated state.” Priority is claimed to U.S. Provisional Application No.
`
`61/178,301 (“’301”), filed May 14, 2009. PCT ’856 and ’301 satisfy the
`
`requirement of 35 U.S.C. § 112, such that the ’018 patent has an effective filing
`
`date of May 14, 2009, which predates the earliest effective filing date to which the
`
`’921 patent may be entitled (October 7, 2009).
`
`IV. SPECIFIC CLAIMS AND GROUND FOR RELIEF
`
`Ground 1. Claims 1-5 of the ’921 patent are obvious over the ’732
`
`publication, either alone or combined with RU ’177 and the ’318 publication.
`
`Ground 2. Claims 6 and 10 of the ’921 patent are obvious over the ’732
`
`publication in view of the ’018 patent, and optionally in view of RU ’177 and ’318.
`
`Ground 3. Claims 7-9 of the ’921 patent are obvious over the ’732
`
`publication in view of Applicants Admitted Prior Art, or, in addition or in the
`
`alternative, Lewkowski and/or Oae, and optionally in view of RU ’177 and ’318.
`
`Ground 4. Claim 1 is obvious over RU ’177.
`
`
`
`4
`
`

`

`
`
`Ground 5. Claims 1-4 are obvious over Partenheimer in view of the ’732
`
`publication combined with or further in view of the ’018 patent.
`
`The grounds for unpatentability are supported by the Declaration under 37
`
`C.F.R. § 42.65 of Kevin J. Martin, Ph.D (Exh. 1009).
`
`V.
`
`STATEMENT OF REASONS FOR THE REQUESTED RELIEF
`
`A. Brief Summary of Reasons for Relief Requested
`
`Independent Claim 1 is directed to a method for the preparation of 2, 5-furan
`
`dicarboxylic acid (“FDCA” or “FDA”). Independent claim 7 relates to a process
`
`for the preparation of a dialkyl ester of FDCA. Each independent claim involves a
`
`first step in which a feed “comprising a compound selected from [a Markush]
`
`group consisting of hydroxymethylfurfural (‘HMF’), an ester of 5-hydroxymethyl-
`
`furfural, 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” is contacted “with an oxygen-containing gas.” ’921//7:61-8:1; 9:3-8.1
`
`
`1 The designation of X:Y refers to the column of the referenced patent or
`
`publication and the line numbers of that column, alternatively, if the publication
`
`does not include columns, X refers to the page number. Accordingly, the
`
`designation “’921//7:61-8:1” refers to patent ’921, column 7, line 61 through
`
`column 8, line 1.
`
`
`
`5
`
`

`

`
`
`The oxidation is conducted in the presence of known oxidation catalysts
`
`comprising both Co and Mn, and further a source of bromine (Br), at a temperature
`
`between 140°C and 200°C, and at an oxygen partial pressure (“pO2”) of 1 to 10 bar
`
`in the presence of a solvent or solvent mixture comprising acetic acid or a mixture
`
`of acetic acid and water. ’921//8:1-6; 9:8-14.
`
`Claim 7 is similar to claim 1 but adds the step of esterifying the oxidation
`
`product, i.e., 2, 5-furan dicarboxylic acid (or FDCA or FDA). ’921//9:1-14.
`
`Dependent claims 2-6 and 10 narrow the HMF specie/catalyst/temperature range of
`
`claim 1. Dependent claims 8 and 9 narrow the dialkyl ester of claim 7.
`
`During prosecution Patent Owner (“PO”) argued that the claimed
`
`combination of temperature and pressure ranges imparted patentability to the
`
`claims over the known prior art. That is, the claimed combination of temperature
`
`and pressure ranges resulted in higher yields for the oxidation process. However,
`
`PO’s purported, but unclaimed, higher yields were limited to the oxidation of HMF
`
`(which is only one of at least seven compounds or combinations of compounds
`
`within the Markush members recited by claims 1 and 7), at a temperature of 180°
`
`C (a single point within the claimed temperature range of “between 140° C and
`
`200° C), and at an pO2 of ~4 bar - a single point within the claimed oxygen partial
`
`pressure range “of 1 to 10 bar”). In other words, the PO’s evidence was not
`
`commensurate with the full scope of claims 1 and 7. See Grasselli v. Rohm &
`
`
`
`6
`
`

`

`
`
`Haas Co., 713 F.2d 731, 743 (Fed. Cir. 1983). In addition, the examiner did not
`
`rely upon the closest prior art we’re aware of.
`
`There is no dispute that the ’732 publication is the closest prior art. EP 02
`
`486 028 Prosecution History (Exh. 1010). See Exh. 1010 at 12 of 231. The ’732
`
`publication is cited by the ’921 patent’s specification. See ’921//1:48. The ’732
`
`publication expressly discloses HMF oxidation reaction conditions for the
`
`preparation of FDCA at an oxidation temperature of 150° C, which is within the
`
`claimed range of between 140° C and 200° C. The ’732 publication’s examples
`
`were performed at an oxygen partial pressure of 14.5 bar, which is close enough to
`
`the claimed range of 1 to 10 bar that it would have been expected that the process
`
`would have achieved substantially the same results, including yield, absent a
`
`showing otherwise. See, e.g., Titanium Metals Corp. of Amer. v Banner, 778 F.2d
`
`775 (Fed. Cir. 1985). Indeed, as reported by the ’732 publication, the process
`
`conditions were able to oxidize HMF (one of the starting materials encompassed
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`by claims 1 and 7) to FDCA with a yield of 54.6% at a temperature of 150° C and
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`at an oxygen partial pressure of 14.5 bar (or 13.8 bar using the ’921 patent’s
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`conversation parameters). See ’732//Table 4, Ex. 40. Example 40 was conducted
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`in the presence of lower levels of catalyst when compared to the oxidation of HMF
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`to FDCA conducted and reported by the ’921 patent. Dec. ¶ 84. The ’732
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`publication expressly discloses “that increasing catalyst concentration at a given
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`7
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`temperature [] nearly always increased the FDA yield.” ’732//15:9-11. The FDCA
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`yields of the ’732 publication are also calculated based on the solids content, where
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`the filtrate is not analyzed, and is known to be less accurate than HPLC
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`measurements (used by the ’921 patent). Dec. ¶ 61, 64, 70. Consequently, the
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`’732 publication underreports the actual FDCA yields, and true yields would have
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`been understood to be higher even at the lower catalyst concentration used. Dec. ¶
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`64, 70.
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`Thus, the claims of the ’921 patent are prima facie rendered obvious in view
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`of the ’732 publication because there is no evidence that reducing the oxygen
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`partial pressure by 4.5 bar2 is critical to the methods or process of oxidizing HMF
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`to FDCA. In fact, the ’921 patent admits that the oxygen partial pressure can
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`“suitably be between 1 and 30 bar,” which obviously encompasses 14.5 bar. The
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`’921 patent refers to an oxygen partial pressure between 1 and 10 as “preferabl[e].”
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`’921//4:51-55. Thus, the ’921 patent does not attribute any criticality to the oxygen
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`partial pressure of the claimed method or process.
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`2 The difference between the ’732 publication’s oxidation process conducted at an
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`oxygen partial pressure of 14.5 bar is about 4 to 4.5 bar higher than the oxygen
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`partial pressure claimed by the oxidation process of claims 1 and 7 of the ’921
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`patent (i.e., about 10.5 bar).
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`8
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`At the very least, the ’732 publication suggested to a person of ordinary skill
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`in the art to vary residence time, temperature and pressure to within the claimed
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`ranges, in order to maximize yield. ’732/7:2-7. The ’732 publication states:
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`For preparation of diacid [(FDCA)], the preferred temperatures are
`about 50° to 250°C, most preferentially about 50° to 160°C. The
`corresponding pressure is such to keep the solvent mostly in the
`liquid phase.
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`See Id. (emphasis added). These variations in temperature and pressure are
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`nothing more than the optimization of oxidation conditions explicitly suggested by
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`the ’732 publication (’732//7:5-7), and a person of ordinary skill in the art would
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`have been motivated and enabled to achieve the claimed process. Dec. ¶¶ 66, 73.
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`Conducting routine experimentation to determine optimal or workable ranges that
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`produce expected results is suggested to one of ordinary skill in the art by the ’732
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`publication. See In re Aller, 220 F.2d 454, 456 (C.C.P.A. 1955).
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`In addition, one of ordinary skill in the art would have been motivated to
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`reduce the pressure in view of RU ’177, which was not cited – and therefore not
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`relied upon – by the PTO during prosecution, as well as by prudent considerations
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`of reducing process cost. Dec. ¶ 66. RU ’177 discloses oxidizing 5-methylfurfural
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`(or 5-MF); a compound encompassed by the claimed Markush group of
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`compounds recited in claims 1 and 7 to FDCA at an oxygen partial pressure
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`(“pO2”) of 2.1 to 6.4 bar, which is within the claimed range “of 1 to 10 bar.” In
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`9
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`
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`Example 1 of RU ’177, 5-MF that is oxidized to FDCA at a temperature of 130° C
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`and a pO2 up to 6.4 bar, reported an FDCA solid’s yield of 36% (see RU ’177//3),
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`compared with the yield reported by the ’921 patent in Example 3b (39.94%),
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`obtained at 180°C at an oxygen partial pressure of 10.5 bar (see ’921//Table 3).
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`The teachings of RU ’177 undermines any alleged unexpected results or criticality
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`based on temperatures and or pressure, as PO’s 180° C only provided an increase
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`in FDCA yield to 39.94% when compared with 36% of the prior art. Dec. ¶¶ 87-
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`90. RU ’177 and the ’732 publication are not isolated teachings, as discussed in
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`greater detail below. As demonstrated herein, prior art of record shown in a new
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`light, as well as newly-cited prior art, discloses and suggests the claimed subject
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`matter to a person of ordinary skill at the time of the alleged invention with at least
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`a reasonable expectation of success.
`
`B.
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`The ’921 Patent
`
`The ’921 patent describes and claims methods for preparing 2, 5-furan
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`dicarboxylic acid (“FDCA”) through oxidation, or its ester through subsequent
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`esterification with, e.g., methanol. HMF, aka 5-hydroxymethylfurfural, and/or
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`HMF derivatives contact an oxygen-containing gas, in the presence of an oxidation
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`catalyst comprising Co, Mn, and Br. PO provides a selective, albeit misleading,
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`discussion of admitted prior art, e.g., the ’732 publication. See ’921//1:48;
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`’921//1:55-59. PO states, “WO 01/72732 describes the oxidation of HMF to
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`10
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`
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`FDCA. The maximum FDCA yield reported is 59%, obtained at 105° C.”
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`’921//1:48-49 (emphasis added). No mention is made regarding the 150°C
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`oxidation temperature of Exs. 38-40 of the ’732 publication. See ’732//Table 4.
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`No mention is made that the ’732 publication explicitly states that yield should be
`
`maximized. See ’732//7:5-7. No mention is made that the reported yields of the
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`’732 publication are based on the separated solid measurement, as compared with
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`the ’921 patent’s HPLC measurements, or that the reported yields are based on
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`lower catalyst concentrations which affect yield by any measurement.
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`Against this background, PO purportedly found that by using a known
`
`combination of oxidation catalysts of Co, Mn, and Br, at temperatures higher than
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`140° C, i.e., 180° C, derivatives of HMF “can be oxidized to FDCA in high
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`yields.” ’921//2:39-45 (emphasis added). As mentioned above, however, the
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`challenged claims fail to recite any limitation relating to yield, residence time, or
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`catalyst concentration. Moreover, it was not until the examiner rejected the
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`original claims that the purported importance of the oxygen partial pressure was
`
`even mentioned as resulting in higher yields. Indeed, the ’921 patent specification
`
`states that it is the higher temperature that allegedly leads to higher yields. See,
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`e.g., ’921//2:39-45.
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`The ’921 patent concurrently admits, however, that the temperature and
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`pressure “in a commercial oxidation process” are determined so that the solvent is
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`11
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`mainly in the liquid phase. See ’921//4:34-41. In the paragraph discussing
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`commercial oxidation, PO discloses that total pressures of between 5 and 100 bar
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`are practiced. ’921//4:39-43. The ’921 patent further states, “[i]n the case of
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`continuously feeding and removing the oxidant gas to and from the reactor, the
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`oxygen partial pressure will suitably be between 1 and 30 bar or more preferably
`
`between 1 and 10 bar.” ’921//4:51-55.
`
`The ’921 patent additionally describes that FDCA or its dialkyl ester can be
`
`reacted with a diol to produce polyester. ’921//3:30-36. FDCA is produced by
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`catalytic oxidation of HMF and its derivatives and “can be transformed using
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`common esterification reactions to a diester by contacting the starting material
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`under appropriate conditions with the relevant alcohol.” ’921//5:20-24 (emphasis
`
`added). The ’921 patent concedes the esterification of FDCA is well known.
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`‘921//5:42-48.
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`C.
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`Prosecution History of the ’921 Patent
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`In the first Office Action, the PTO rejected the claims in view of Sanborn et
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`al (US 2009/0156841), which discl