U.S. Patent No.: 8,865,921
`Petitioners’ Reply
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`Paper No. ___
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`UNITED STATES PATENT AND TRADEMARK OFFICE
`____________________
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`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`____________________
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`E. I. DU PONT DE NEMOURS AND COMPANY and
`ARCHER-DANIELS-MIDLAND COMPANY,
`Petitioners,
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`v.
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`FURANIX TECHNOLOGIES B.V.,
`Patent Owner.
`
`____________________
`
`Inter Partes Review No.: IPR2015-01838
`U.S. Patent No. 8,865,921
`____________________
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`PETITIONERS’ REPLY
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`Petitioners’ Reply
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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.
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`FURANIX TECHNOLOGIES B.V.,
`Patent Owner.
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`____________________
`
`Inter Partes Review No.: IPR2015-01838
`U.S. Patent No. 8,865,921
`____________________
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`PETITIONERS’ REPLY
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`Page No.
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`TABLE OF CONTENTS
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`Introduction & Summary of Argument ........................................................... 1
`I.
`II. Argument ......................................................................................................... 2
`A.
`Person Having Ordinary Skill in the Art ............................................... 2
`B.
`Claim Construction................................................................................ 2
`1.
`“Between 140° C. and 200° C.” .................................................. 3
`2.
`“At an Oxygen Partial Pressure of 1 to 10 bar” .......................... 3
`3.
`Claim Terms Not Present ............................................................ 4
`Claims 1-5 of the ’921 patent are unpatentable as obvious over the
`’732 publication in view of RU ’177 and the ’318 publication ............ 5
`1.
`The Prior Art ............................................................................... 5
`2.
`Secondary Considerations ......................................................... 15
`Claims 7-9 of the ’921 patent are obvious. ......................................... 26
`D.
`III. Conclusion ..................................................................................................... 26
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`C.
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`i
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`TABLE OF AUTHORITIES
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` Page(s)
`
`Cases
`In re Aller,
`220 F.2d 454 (C.C.P.A. 1955) .............................................................................. 9
`In re Applied Materials, Inc.,
`692 F.3d 1289 (Fed. Cir. 2012) ............................................................................ 7
`EWP Corp. v. Reliance Universal Inc.,
`755 F.2d 898 (Fed. Cir. 1985) .............................................................................. 6
`In re Peterson,
`315 F.3d 1325 (Fed. Cir. 2003) ............................................................................ 6
`Titanium Metals Corp. v. Banner,
`778 F.2d 775 (Fed. Cir. 1985) ............................................................................ 15
`In re Wertheim,
`541 F.2d 257 (C.C.P.A. 1976) ............................................................................ 14
`In re Woodruff,
`919 F.2d 1575 (Fed. Cir. 1990) .......................................................................... 15
`
`
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`
`ii
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`UPDATED LISTING OF EXHIBITS
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`U.S. Patent No. 8,865,921 B2 (filed Oct. 6, 2010).
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`
`
`Exhibit 1001:
`
`Exhibit 1002:
`
`International Application Publication WO 01/072732 A2 (filed
`Mar. 27, 2001).
`
`Exhibit 1003: 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.
`
`U.S. Patent No. 8,558,018 B2 (filed May 14, 2010).
`
`Exhibit 1004:
`
`Exhibit 1005:
`
`
`Exhibit 1006:
`
`
`Exhibit 1007:
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`Exhibit 1008:
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`Exhibit 1009:
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`Exhibit 1010:
`
`Exhibit 1011:
`
`
`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.
`
`USSR Patent RU-448177A1 (filed Oct. 30, 1972) (cited to
`Certified English Language Translation).
`
`U.S. Patent Publication No. US 2008/0103318 (filed Oct. 31,
`2007).
`
`Declaration of Dr. Kevin J. Martin.
`
`Prosecution History of European Patent Application No. 2 486
`028 A0 (filed Oct. 7, 2009).
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`Prosecution History of U.S. Patent No. 8,865,921 B2.
`
`iii
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`
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`Exhibit 1012:
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`Exhibit 1013:
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`Exhibit 1014:
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`Exhibit 1015:
`Exhibit 1016:
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`Exhibit 1017:
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`Exhibit 1018:
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`Exhibit 1019:
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`Exhibit 1020:
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`Exhibit 1021:
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`Exhibit 1022:
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`Exhibit 1023:
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`Exhibit 1024:
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`Exhibit 1025:
`
`
`Brian S. Furniss et al., VOGEL’S TEXTBOOK OF
`PRACTICAL ORGANIC CHEMISTRY (5th ed. 1989).
`
`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.
` International Application Publication WO 2007/146636 A1
`(filed June 4, 2007).
`
` 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.
`
` 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.
`
`MCGRAW-HILL ENCYCLOPEDIA OF CHEMISTRY, (Sybil
`P. Parker et al. eds., 5th ed. 1983).
`
` U.S. Patent Publication No. 2009/0156841 (filed Dec. 12,
`2008).
`
` U.S. Patent No. 4,792,621 (filed Jul. 28, 1986).
`
`HAWLEY’S CONDENSED CHEMICAL DICTIONARY
`(13th ed. 1997 at 92).
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` U.S. PATENT NO. 5,099,064 (FILED MAR. 24, 1992).
`
`iv
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`
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`Exhibit 1026:
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`Exhibit 1027:
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`Exhibit 1028:
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`Exhibit 1029:
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`Exhibit 1030:
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` KIRK-OTHMER ENCYCLOPEDIA OF CHEMICAL
`TECHNOLOGY, (Jacqueline I. Kroschwitz et al. eds., 4th ed.
`vol. 18, 1996).
`Deposition Transcript of Dr. Kevin J. Martin (Dated May 25,
`2016).
`Declaration #2 of Dr. Kevin J. Martin.
`
`U.S. Patent No. 8,519,167 (filed Aug. 27, 2013).
`
`International Application Publication WO 2010/111288
`(Published Sept. 30, 2010).
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`v
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`I.
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`INTRODUCTION & SUMMARY OF ARGUMENT
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`The challenged claims of U.S. Patent 8,865,921 (“the ’921 patent”) relate to
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`the admittedly well-known Co/Mn/Br catalysis of furan derivative substrates (e.g.,
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`5-hydroxymethylfurfural (“HMF”)) in the presence of acetic acid to produce 2,5-
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`furandicarboxylic acid (“FDCA”), and are prima facie obvious in light of
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`International Publication No. WO 01/072732 (“the ’732 publication”), USSR
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`Patent Publication 448177 (“RU ’177”), and U.S. Patent Publication 2008/0103318
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`(“the ’318 application”), which disclose the two allegedly distinguishing claim
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`limitations argued by Patent Owner (“PO”) – temperature and oxygen partial
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`pressure.
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`PO’s reliance on alleged unexpected results cannot withstand scrutiny as PO
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`fails to provide an apples-to-apples comparison between the claimed process and
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`processes outside the scope of the claims; rather, PO provides an “apples and
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`oranges” comparison by comparing reactions having very different catalyst
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`concentrations - a variable known to affect process yield. Moreover, PO’s failure
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`to explain commercial viability and its failure to show unexpected yields or the
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`criticality of the claimed ranges cannot support its arguments of meeting a long-felt
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`need. And, PO’s fabricated copying narrative cannot confer patentability to an
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`unpatentable process.
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`Accordingly, claims 1-5 and 7-9 should be canceled.
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`II. ARGUMENT
`Person Having Ordinary Skill in the Art
`A.
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`PO’s construction of a person having ordinary skill in the art (“POSA”) is
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`untenable, especially in light of PO’s expert’s deposition testimony; the
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`construction places too many limitations on a POSA. See Exh. 1028, ¶ 7. For
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`example, it appears PO’s POSA – a person with a Bachelor’s degree and limited
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`experience in the field – would not have considered the effect catalyst
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`concentration would have had on the catalytic oxidation reaction of HMF to
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`FDCA. As a result, PO’s POSA appears to be limited, whereas Petitioner’s
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`hypothetical POSA – as defined by Dr. Martin – would have the knowledge and
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`experience to understand that catalyst concentration is a result-effective variable
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`that impacts yield. See, e.g., id. As such, to the extent necessary, the Board should
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`adopt Petitioner’s POSA.
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`B. Claim Construction
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`PO did not address many of the phrases or terms appearing in the challenged
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`claims, such as “comprising”. See Paper 1 at 21. As a result, to the extent that
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`interpretations of these phrases and terms are required for a Final Written Decision
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`in this proceeding, Petitioners’ claim interpretations stand unchallenged.
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`2
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`There are two phrases in dispute, the temperature range and the pressure
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`range. However, PO also appears to be reading limitations into the claims that
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`simply are not there. Petitioners address these below.
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`“Between 140° C. and 200° C.”
`1.
`As Dr. Martin previously explained, the specification does not use the phrase
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`“between 140° C and 200° C.” Ex. 1009, ¶ 53. PO’s expert similarly could not
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`find the phrase “between 140° C and 200° C” in the specification. Exh.
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`2020//26:3-28:2. The specification, however, does state that the “temperature of
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`the reaction mixture is at least 140° C., preferably from 140 and 200° C. . . ,”
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`which would imply that the claimed temperature range could include 140° C and
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`200° C. See id. at 28:17-20. PO relies on an original claim that stated that the
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`temperature was “higher than 140° C,” but the issued claims do not recite such
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`language. Exh. 2020//26:21-27:15.1 Accordingly, the broadest reasonable
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`interpretation of the phrase should include the endpoints. Ex. 1009, ¶ 53.
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` “At an Oxygen Partial Pressure of 1 to 10 bar”
`2.
`PO’s interpretation of the phrase is based purely on attorney argument, and
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`is not factually supported. Indeed, PO’s expert admitted that he did not address the
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`1 Dr. Martin’s alleged admission referred to his reading of the original claims, but
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`his declaration addressed the issued claims. Ex. 1027//107:5-8.
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`3
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`limitation. Exh. 2020//48:20-49:7. He also admitted that Example 3 of the ’921
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`patent was run at a pressure of 50 bar air (see id. at 53:11-14), which translates to
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`an oxygen partial pressure of greater than 10 bar (or as Dr. Martin testified, about
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`10.5 bar (see Exh. 1009, ¶¶ 52, 87)).
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`3. Claim Terms Not Present
`It appears that PO is relying on yield and commercial viability to support the
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`patentability of the claims. The claims, however, are silent on both.
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`The yield is a direct function of certain known result-effective variables;
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`namely, temperature, pressure, catalyst concentration, and time of reaction. See
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`Exh. ’732//7:5-7 (“The preferred reaction time is determined by the temperature,
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`pressure and catalyst concentration such that a maximum yield of diacid [(i.e.,
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`FDCA)] is obtained.”) (emphasis added). Of the four identified result-effective
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`variables, the claims only recite two - temperature and pressure (within ranges that
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`overlap or abut known ranges (see, e.g., Paper 1 at 27)). The claims do not recite a
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`catalyst concentration. See ’921//7:61-9:23. As Dr. Martin previously explained,
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`and which PO failed to address, the ’921 patent’s experiments use nearly three
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`times the amount of catalyst to HMF ratio as compared to the ’732 publication’s
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`experiments. See Exh. 1009, ¶¶ 83-84. The claims also do not recite the time of
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`reaction. See ’921//7:61-9:23. Indeed, PO even relies on data from experiments
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`where the reaction times are different. See, e.g., Exh. 2007, ¶ 37 (showing reaction
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`4
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`times of 2 hours at 145° C and 0.5 hours at 190° C).2 It is not surprising, therefore,
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`that the claims do not recite a yield percentage (especially since some of the
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`claimed reactions give a yield percentage as low as 7.19%). See ’921//Table 3.
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`Because the claims are silent as to yield, they cannot be relied upon to allege
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`commercial viability (especially since PO’s expert conceded that many of the yield
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`percentages achieved by the claimed reaction were not commercially viable. Exh.
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`2020//37:14-38:8 and 39:13-41:8 (“There’s not like a line in the sand.”).
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`C. Claims 1-5 of the ’921 Patent are Unpatentable as Obvious Over
`the ’732 Publication in View of RU ’177 and the ’318 Publication
`Nothing presented in the Response, including the exhibits, substantiates the
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`patentability of the challenged claims.
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`1. The Prior Art
`The ’732, ’318 and RU ’177 publications all relate to the catalytic oxidation
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`and conversion of aromatic furan derivatives, e.g., HMF or 5-
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`Hydroxymethyfurfural (“5-MF”), to FDCA over temperature ranges that
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`completely encompass, or at least abut, the claimed ranges, and at oxygen partial
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`pressures either overlapping the claimed ranges or close enough that a POSA
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`2 Interestingly, the Response (at 40) (Paper 23) incorporates Figure 1 from Exh.
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`2007, but omits the reaction time of the experiments. Compare Paper 23 at 40 with
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`Exh. 2007 at 31.
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`5
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`would have expected that the reactions had the same properties. See Paper 1 at 27-
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`28. All three references are concerned with solving the same problem: finding
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`oxidation reactions to obtain high FDCA yields. See, e.g., ’732//7:2-7;
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`’318//[0055].
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`PO simply ignores these teachings, and instead only focuses on specific
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`examples provided therein. But such an analysis is improper. “A reference must
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`be considered for everything it teaches by way of technology and is not limited to
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`the particular invention it is describing and attempting to protect.” EWP Corp. v.
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`Reliance Universal Inc., 755 F.2d 898, 907 (Fed. Cir. 1985) (emphasis in original);
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`see also In re Peterson, 315 F.3d 1325, 1330 (Fed. Cir. 2003) (“The normal desire
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`of scientists or artisans to improve upon what is already generally known provides
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`the motivation to determine where in a disclosed set of percentage ranges is the
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`optimum combination of percentages.”).
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`Temperature
`a.
`It is undisputed that the ’732 publication teaches preparing the diacid FDCA
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`at a preferred temperature of “about 50° to 250°C, most preferentially about 50° to
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`160°C” (’732//7:2-4), as exemplified by FDCA production at temperatures of
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`6
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`75°C, 100°C, 105°C, 125°C, and 150°C.3 See Paper 23 at 16 (citing ’732//7:2-4);
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`see also id. at 16-17; ’732//Tables 3 and 4. Thus, the ’732 publication would have
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`provided guidance to a POSA of the temperature range to have been used in
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`oxidation reactions converting HMF to FDCA. See Paper 1 at 30-31; see also,
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`Exh. 2020//20:19-21:1 (admitting that PO’s POSA would have been able to
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`conduct reactions within a provided temperature range). In addition, and even
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`though the claims are not limited to any particular yield, a POSA would have
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`known that an increased temperature within the range provided would have
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`increased the FDCA yield, either by increasing the conversion rate, the selectivity,
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`or both. See Exh. 1009, ¶ 71 (citing ’732//FIG. 7 and Partenheimer//Tables 2 and
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`3). This result would not have been surprising or unexpected; indeed, such a result
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`would have been expected. See Partenheimer//105 (“The yield increases . . . with
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`temperature.”); see also Partenheimer//105 (“the conversion increases with
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`temperature, as expected.”) (emphasis added); Exh. 1028, ¶ 7 (citing Figures 30
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`3 “A reference must be considered for everything that it teaches, not simply a
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`preferred embodiment or working examples.” In re Applied Materials, Inc., 692
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`F.3d 1289, 1298 (Fed. Cir. 2012).
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`7
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`and 31 of the ’318 publication showing increased yield at increased temperatures);
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`Exh. 2003, ¶ 59.
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`While PO acknowledges that “[t]he ’732 publication states that ‘for
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`preparation of the diacid, the preferred temperatures are about 50° to 250°C, most
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`preferentially about 50° to 160°C,’” it concludes (without evidence or explanation)
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`that “[t]his disclosure does not provide the range recited in claim 1 (between 140
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`and 200°C) or in claim 5 (between 160 and 190°C.).” Paper 23 at 16. But that
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`simply ignores the evidence which shows significant overlap between the prior art
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`and claimed temperature ranges (as depicted below).4
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`4 While Ex. 2004 – introduced by PO – is not prior art, its temperature range is
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`within the prior art’s range.
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`8
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`This overlap alone supports a finding of a prima facie case of obviousness.5
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`See In re Aller, 220 F.2d 454, 456 (C.C.P.A. 1955) (“[W]here the general
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`conditions of a claim are disclosed in the prior art, it is not inventive to discover
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`the optimum or workable ranges by routine experimentation.”).
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`Rather than address the prima facie case of obviousness, PO instead
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`attempts to obfuscate the teachings of the ’732 publication by focusing exclusively
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`on its examples. According to PO, temperature-staged examples of the ’732
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`publication show HMF first converted to DFF at a lower temperature, and
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`subsequently converted to FDCA at a higher temperature. See id. at 16-17.
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`PO’s arguments rely on Ex. 13 of Table 3 in which the HMF is oxidized in
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`the presence of Zr and has a conversion percentage of 99.7%. Other examples
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`disclosed in the ’732 publication, however, show HMF conversion percentages of
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`as little as 60.4%. Thus, not all of the HMF has been converted as PO suggests.
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`Even if the small amount of HMF is entirely converted to other starting
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`materials, which has not been shown, one such starting material that HMF converts
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`to is 5-acetoxymethyl furfural, which is an HMF ester, and falls within the scope of
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`the challenged claims. See Exh. 1009, ¶ 22; see also ’732//Table 3 (showing a
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`5 As discussed below, PO fails to provide any evidence to support any criticality to
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`its claimed pressure range.
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`9
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`DFF selectivity of only 61.6%). Once the temperature is raised, and as PO’s expert
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`implicitly admits, at least the HMF ester is contacted at the elevated temperature,
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`which falls within the claimed scope. See Exh. 2003, ¶ 56.
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`And while the ’732 publication provides specific examples where
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`temperatures are staged, it does not change its disclosure of FDCA production at
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`the temperature ranges provided above. A POSA would have known at the time of
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`the invention that “staging the temperature from an initial value [for 1 hour and
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`then a higher temperature] for 2 h[ours] gave no better results than the oxygenation
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`at [the higher value] for 3 h[ours] (Figure 7).” Partenheimer//105. As a result, a
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`POSA would not have considered that staging the temperature would have resulted
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`in higher yields, and would have been motivated to simply react HMF at a higher
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`contact temperature to obtain FDCA. See Exh. 1028, ¶¶ 13-17. A POSA would
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`have further been motivated to react HMF at a higher, constant temperature
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`because it would have simplified the reaction process. See id. at ¶ 17.
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`Further, a POSA would have also looked to the ’318 publication and RU
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`’177 that also relate to the production of FDCA. See Exh. 1028, ¶¶ 24-28. The
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`’318 discloses a process of forming FDCA from HMF while RU ’177 discloses a
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`process of forming FDCA from 5-MF (another one of the claimed starting
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`materials). Both references provide oxidation reaction at constant temperatures
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`that overlap with or abut the claimed temperature ranges. PO concedes that the
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`10
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`’318 publication teaches conducting the reactions at a temperature “from about 50°
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`C. to about 200° C., with a preferred range of from 100° C. through about 160° C.”
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`(Paper 23 at 22), which overlaps with the ’732 publication’s preferred range.
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`Certainly, a POSA would have been further motivated to optimize the ’732
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`publication’s temperature range with the ’318 publication’s confirmation that the
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`range of 50° C. to 250° C. is a range within which HMF converts to FDCA. Exh.
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`1028, ¶ 28; see also ’318//Figs. 30 and 31. Similarly, RU ’177 discloses oxidation
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`reactions at temperatures of 115° - 140° C, which overlaps or at least abuts the
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`claimed range. See Paper 1 at 35 (quoting RU ’177 at 1).
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`Moreover, as explained by Dr. Martin, and which PO fails to address, the
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`preferred range for aqueous acidic solvents (e.g., acetic acid-water mixture) – that
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`all three references teach using – “is in the range of about 120° C. to about 240°
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`C., preferably about 150° C. to about 230° C. Various narrower ranges may be
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`preferred for a particular aromatic alkyl being oxidized.” See Exh. 1009, ¶ 66
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`(quoting ’064//3:39-44) (emphasis added)).6
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`6 Contrary to PO’s representations (Paper 23 at 57), Dr. Martin’s testimony is
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`entirely consistent with the ’064 patent. Moreover, Partenheimer specifically
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`states that “HMF oxidation reactions are based on large scale industrial synthesis
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`11
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`Thus, the teachings of these references, and the knowledge in the art, would
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`have motivated a POSA to optimize the temperature conditions with the ranges
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`provided therein depending on the acetic acid-water mixture used and the amount
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`of substrate and catalyst used. In addition, because it was known that increased
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`temperatures provide higher yields, and that these increased temperatures were not
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`required to be staged and indeed that staging provided no better results, a POSA
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`would have optimized the oxidation temperature based on the desired solvent,
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`reaction time, and catalyst concentration in the range provided by the prior art
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`references. See, e.g., Exh. 1009, ¶ 66.
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`Pressure
`b.
`The ’732 publication teaches that the “corresponding pressure [of the
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`oxidation reaction to form FDCA] is such to keep the solvent mostly in the liquid
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`phase,” and further provides motivation to optimize what the art demonstrates to be
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`result-influencing variables: “[t]he preferred time of the reaction is determined by
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`the temperature, pressure and catalyst concentration such that a maximum yield of
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`[FDCA] is obtained.” ’732//7:2-7 (emphasis added).
`
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`of hydrocarbons including xylene,” which are discussed in both the ’064 and ’621
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`patents. See Partenheimer//102 (emphasis added); see also Exh. 1009, ¶ 66.
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`12
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`Examples of the ’732 publication’s oxidation reactions were performed at an
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`oxygen partial pressure of 14.5 bar. Likewise, RU ’177 teaches oxidation reactions
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`to form FDCA at oxygen partial pressures of 2.1 to 6.4 bar. The ’318 publication
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`teaches the production of FDCA at a “preferred pressure” “in the range of 150-500
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`psi.” This translates to an oxygen partial pressure of 2.17 to 7.24 bar (for air) and
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`10.34 to 34.47 bar (for pure oxygen-fed reactions). According to the ’921 patent,
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`the oxygen partial pressures can “suitably be between 1 and 30 bar,” which
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`obviously encompasses the prior art’s ranges as shown below.
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`PO fails to provide any evidence that the oxygen partial pressure imparts any
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`criticality to the claimed reaction as none of the experiments it relies on were
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`conducted outside of the claimed range. Moreover, a POSA would have been
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`13
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`motivated to lower the oxygen partial pressure based on RU ’177 because a POSA
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`would have known that 5-MF is an HMF derivative, and has a substantially similar
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`chemical structure as HMF. See Exh. 1009, ¶ 22. A POSA would have understood
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`the conditions of oxidizing 5-MF can apply to the HMF oxidation reactions taught
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`by the ’732 publication. See Exh. 1009, ¶ 96.
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`A POSA also would have considered the ’318 publication as relevant to the
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`teachings of the ’732 publication because like the ’732 publication (and RU ’177),
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`the ’318 publication specifically teaches the oxidation reaction of HMF to FDCA
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`in acidic aqueous solution solvent systems including acetic acid in either batch
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`reactors or continuous flow processes. See ’318//[0049]; see also Exh. 1028, ¶¶
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`28-28. While PO argues that the catalyst system differs from the claimed one,
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`there is no evidence that such a difference is material to the oxygen partial
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`pressure.
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`As Dr. Martin explained, a POSA would have known that the pressures used
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`are a function of the solvent system. “[W]hen the aqueous acidic solvent is an
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`acetic acid-water mixture, suitable gauge pressures in the reactor can be up to
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`about . . . [9.8 bar to 29.42 bar],” which translates to an oxygen partial pressure of
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`2.05 to 6.15 bar. See Exh. 1009, ¶ 66 (quoting ’064//3:31-33).
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`Because the claimed ranges “overlap or lie inside ranges disclosed by the
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`prior art,” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257,
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`14
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`267 (C.C.P.A. 1976); In re Woodruff, 919 F.2d 1575, 1578 (Fed. Cir. 1990); see
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`also Titanium Metals Corp. v. Banner, 778 F.2d 775, 783 (Fed. Cir. 1985) (a prima
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`facie case of obviousness exists where the claimed ranges are close).
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`In this case, PO’s expert admitted that a POSA, as he defined it, would have
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`been able to run oxidation reactions to arrive at FDCA, design experiments, run
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`tests within a particular range, and would have reviewed peer-reviewed
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`publications. See Exh. 2020//20:5-21:6. All of that information, including the
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`peer-reviewed papers, would have provided that person with all of the necessary
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`tools to find the optimal and workable ranges. See Exh. 1028, ¶ 7. Indeed, Dr.
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`Schammel testified that he “would [have] tr[ied] a bunch of different variables
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`obviously, but you don’t know what to expect until you do it.” Exh. 2020//67:20-
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`68:12; see also Exh. 2020//71:8-73:2 (agreeing that temperature, pressure, and time
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`are all parameters that affect yield).
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`2. Secondary Considerations
`PO relies – as it did during prosecution – on allegedly high, yet unclaimed,
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`yields achieved by the claimed process. According to PO, the allegedly high yields
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`render the process “commercially viable” despite the following: a) the examples
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`relied upon were conducted at a scale of 5 milliliters, and according to PO’s expert,
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`a POSA as he defined it, could “not necessarily” have scaled up the process; b)
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`PO’s expert admitted that the achieved yields – many of which were close to the
`
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`15
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`
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`yields achieved by the prior art – were not commercially viable; and c), PO’s
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`allegedly unexpected yields rely on an “apples and oranges” comparison between
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`the claimed process and the prior art.
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`a.
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`Commercially Viable
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`The ’921 patent provides examples conducted at a scale of about 5 mL in 8
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`mL reaction vessels. Production of FDCA at this scale is not commercially viable.
`
`See Exh. 1028, ¶¶ 30-32. Commercial processes are typically orders of magnitude
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`higher. See id. There is no evidence that the claimed process could be scaled up
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`by these orders of magnitude to achieve the yields reported by the ’921 patent at a
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`5 mL scale; indeed, the May 2016 experiments conducted by Dr. Gruter were on
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`the same scale as those in the ’921 patent. See Exh. 2007, ¶ 33. One would have
`
`expected that the May 2016 experiments would have been conducted at
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`commercial (or near commercial) scale, if the examples of the ‘921 patent – testing
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`conducted about seven years ago – indeed demonstrated commercial viability. But
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`PO failed to provide that evidence. Moreover, when asked whether a POSA would
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`have known how to scale up the claimed process, Dr. Schammel said “not
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`necessarily,” and continued that he was an expert and would not rely on the ‘921
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`patent’s disclosure. Exh. 2020//78:11-22. And while he added that the results
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`were “promising,” there is no evidence to support his conclusion despite the fact
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`that Dr. Gruter had the opportunity to provide that evidence, but did not. Implicit
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`16
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`
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`in Dr. Schammel’s testimony is that additional experiments are necessary to ensure
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`the reaction vessel can both safely and successfully conduct the oxidation. See
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`Exh. 1028, ¶ 32. Thus, yields at small scale alone do not guarantee commercial
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`viability if a full-sized reactor cannot safely or successfully operate at such
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`conditions. See id. Because PO failed to address these points, the argument that
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`the claimed process is commercially viable should be given little if any weight.
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`b.
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`Yields
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`Product yields is not a claim limitation, likely because the yields of the
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`claimed process, ranging from as low as 7.19% to as high as 78.08%, overlap the
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`yield percentages reported by the cited prior art references. Indeed, PO’s
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`experiments 2a and 2b – conducted at 100° C and therefore outside of the claimed
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`range – had yields greater than 16.17%. See ’921//Table 2.
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`With respect to 5-MF, PO relies on yields of 39.94% and 42.62%, which is
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`not much different from the yield of 39% reported by RU ’177. See Paper 23 at
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`38. Aside from the yields not being “surprising” or “unexpected” to distinguish
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`over the prior art, PO’s expert admitted that these yields – and yields less than
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`these – are “probably not” commercially viable. See Exh. 2020//37:11-38:8; see
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`also id. at 36:11-37:10.
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`17
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`Accordingly, the yields encompassed, but not claimed, by the claim 1
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`process – which overlap with the prior art – cannot be said to be any more or any
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`less commercially viable than the yields achieved by the prior art processes.
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`c.
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`Catalyst Concentration
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`The Petition addressed the differences in the catalyst concentration – not a
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`recited claim limitation – in the oxidation reactions reported in both the ’921 patent
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`and the ’732 publication, each concerning the oxidation of HMF to FDCA (i.e.,
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`claim 2). As Dr. Martin previously testified, the catalyst concentration relative to
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`the feed (or substrate) can have a significant impact on the yield. See Ex. 1009, ¶
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`72. If the relative concentration (or molar percent) of the catalysts is increased, the
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`yields of the reaction will naturally increase. See id. Dr. Martin testified that the
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`experiments in the ’921 patent used over three times as much catalyst
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`concentration relative to the HMF substrate as compared with the catalyst
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`concentration used in the ’732 publication’s examples. See id. at ¶ 83-85.
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`Dr. Gruter’s experiments similarly used the same catalyst concentration as
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`the experiments reported in the ’921 patent. See Exh. 1028, ¶ 35. Thus, the
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`experiments and data relied upon by PO’s Response are not apple-to-apple
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`comparisons with the prior art; rather, they are “apples and oranges” comparisons
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`with changes to variables known and expected to increase yields of FDCA. See
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`18
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`Exh. 2020//59:9-14. Both the ’732 publication and Partenheimer state that yield
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`increases with increased catalyst concentration. ’732//15:9-11; Partenheimer//105.
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`The Response argues that a POSA would have understood that the maximum
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`obtainable yield of an HMF oxidation reaction to form FDCA would have been
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`70%. The Response (and Dr. Schammel) cites to Partenheimer for that
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`proposition. However, Partenheimer says no such thing. Instead, Partenheimer
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`states that the “[e]xtrapolat[ed]”data “suggests” that the maximum obtainable
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`FDCA yield is about 70% using the catalyst system “at the specified molar ratios
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`of these elements.” Partenheimer//105 (emphasis added). Partenheimer then goes
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`on to specifically invite POSAs to optimize the catalyst system by stating “[i]t is
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`believed that variation of the molar amounts of the Co, Mn, Zr, and Br could well
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`improve the yield of [FDCA].” Id. This language by Partenheimer explicitly
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`contemplates that the yield can be improved to a percentage greater than 70% by
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`varying the molar amounts of the catalyst system.
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`The ’921 patent reports nothing more than what Partenheimer suggested and
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`expected; increased yields with increased catalyst concentration.7 Indeed, even the
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`7 PO only provides allegedly surprising or unexpected results for one species of a
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`Markush group, and cannot show that each specie in the Markush group provided
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`surprising or unexpected resul
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