UNITED STATES PATENT AND TRADEMARK OFFICE
`_________________________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`_________________________
`
`E. I. DU PONT DE NEMOURS AND COMPANY and
`ARCHER-DANIELS-MIDLAND COMPANY,
`Petitioners,
`
`v.
`
`FURANIX TECHNOLOGIES B.V.,
`Patent Owner
`_________________________
`
`Case IPR2015-01838
`Patent 8,865,921
`_________________________
`
`DECLARATION OF WAYNE P. SCHAMMEL, PH.D.
`
`Exhibit 2003
`E.I. du Pont de Nemours & Co. and
`Acher-Daniels-Midland Co. v. Furanix Technologies BV
`IPR2015-01838
`
`
`_________________________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`_________________________
`
`E. I. DU PONT DE NEMOURS AND COMPANY and
`ARCHER-DANIELS-MIDLAND COMPANY,
`Petitioners,
`
`v.
`
`FURANIX TECHNOLOGIES B.V.,
`Patent Owner
`_________________________
`
`Case IPR2015-01838
`Patent 8,865,921
`_________________________
`
`DECLARATION OF WAYNE P. SCHAMMEL, PH.D.
`
`Exhibit 2003
`E.I. du Pont de Nemours & Co. and
`Acher-Daniels-Midland Co. v. Furanix Technologies BV
`IPR2015-01838
`
`
`
`I, Wayne P. Schammel, Ph.D., declare and state as follows:
`
`I.
`
`QUALIFICATIONS
`
`1.
`
`For the past forty years, I have worked as a research chemist, specializing
`
`in the development of homogeneous and heterogeneous catalysts, in particular for
`
`use in oxidation reactions. I also have particular experience utilizing high
`
`throughput experimentation (“HTE”) methodologies for the development of such
`
`catalysts.
`
`2.
`
`I received my Bachelors of Science in chemistry from the University of
`
`Nebraska. I earned my PhD in inorganic chemistry from the Ohio State
`
`University.
`
`3.
`
`In 1976, I joined Amoco Chemicals Company as Research Chemist and
`
`was promoted to Staff Research Chemist in 1982. During my time as Research
`
`Chemist and Staff Research Chemist, I provided process design data for the
`
`Whiting polybutylene unit, conducted research relating to polyisobutylene during
`
`which I discovered the fundamental relationship between impurities and polymer
`
`molecular weight, and designed and constructed a low temperature xylene
`
`crystallization unit.
`
`4.
`
`I was promoted to Senior Research Chemist at Amoco Chemicals
`
`Company in 1985, and in 1992, I was promoted to Senior Research Associate.
`
`While I was Senior Research Chemist and Senior Research Associate, I was the
`
`-2-
`
`
`
`senior technical leader responsible for process improvements on the trimellitic
`
`anhydride (“TMA”) process. As part of this role, I designed, developed and
`
`implemented several significant catalyst improvements that enhanced the oxidation
`
`yield of pseudocumene to TMA. These improvements resulted in estimated annual
`
`savings of $2-3 million. I also reduced catalyst costs by $1 million per annum
`
`when catalyst metal prices escalated. In addition, I provided active technical
`
`support to Amoco’s Manufacturing department as needed which included solving
`
`significant corrosion, plugging and energy problems.
`
`5.
`
`In 2002, I joined BP Americas Company – Aromatics and Acetyls as
`
`Process Chemistry Lead for Aromatics. In this position, I led the Process
`
`Chemistry Community of Practice, a strategic network of chemists to ensure best
`
`in class position for process chemistry in BP Aromatics. I guided the development
`
`and implementation of tools to facilitate research and increase productivity, in
`
`particular using knowledge management and technical software tools. I identified,
`
`monitored and addressed worldwide threats and opportunities to the purified
`
`terephthalic acid (“PTA”) business by performing a SWOT analysis of projects and
`
`activities. As part of this analysis, gaps with competitors were addressed and
`
`strengths were enhanced. I also established new external partnerships with
`
`academic and industrial specialists, which served to leverage R&D resources
`
`effectively. HTE capabilities were enhanced and academic partnerships were
`
`-3-
`
`
`
`nourished and improved.
`
`6.
`
`In 2004, I was promoted to Senior Research Associate. In this role, I
`
`formed and guided a team of five chemists in a catalyst discovery program on
`
`PTA. I led the team that discovered and developed a new oxidation catalyst
`
`family, which has the potential to dramatically reduce both capital and operating
`
`costs for the production of PTA and other aromatic acid products. I stimulated the
`
`use of HTE in catalyst discovery and development projects, thus saving several
`
`hundred thousand dollars per year in research costs and making rapid and profound
`
`discoveries.
`
`7.
`
`In 2009, I joined Siluria Technologies, Inc. as Lead Principal Scientist,
`
`and I have maintained that role to date. At Siluria Technologies, I have discovered
`
`and developed several families of novel fixed bed catalysts for the oxidative
`
`coupling of methane, some of which are currently being scaled up for
`
`demonstration testing and eventual commercialization.
`
`8.
`
`I have also served as a consultant involving homogeneous oxidation with
`
`air or oxygen using cobalt/manganese/bromine based catalysts. One of the projects
`
`I consulted on concerned the oxidization of HMF ethers (for example 5-
`
`methoxymethylfurfural (MMF) and 5-ethoxymethylfurfural (EMF)) for the
`
`preparation of 2,5-furandicarboxylic acid (FDCA) and esters of FDCA. This
`
`consulting work led to my being an inventor on U.S. patent 8,519,167, assigned to
`
`-4-
`
`
`
`Patent Owner Furanix Technologies B.V.
`
`9.
`
`I am an inventor on twenty-eight U.S. patents, including patents on
`
`oxidation catalyst technology. I am also an inventor on eighteen active patent
`
`applications on new oxidation catalyst technology, and an inventor on five
`
`international patent applications on catalyst technology. I am author or co-author
`
`of seven publications, including papers on oxidation reactions and chemical
`
`synthesis. A copy of my CV is provided as Exhibit 2019.
`
`10.
`
`I am being compensated for my time working on this proceeding at a rate
`
`of $200/hour. My compensation in no way depends on the outcome of this
`
`proceeding.
`
`II.
`
`INFORMATION CONSIDERED
`
`11.
`
`In forming my opinion, I have relied upon my accumulated scientific
`
`knowledge and experience. I have reviewed U.S. patent 8,865,921, as well as the
`
`documents cited in this declaration. I have also reviewed the Declaration of Kevin
`
`J. Martin (“Martin Decl.,” Ex. 1009) and the documents cited in Dr. Martin’s
`
`declaration. I have reviewed the Declaration of Gert-Jan Gruter, Ph.D. (“Gruter
`
`Decl.,” Ex.2007) and the documents cited in Dr. Gruter’s declaration. A list of
`
`documents I reviewed in forming my opinions can be found as Appendix A, at the
`
`end of this declaration.
`
`-5-
`
`
`
`III. BACKGROUND
`The Present Inter Partes Review Proceeding
`Petitioners, E. I. Du Pont De Nemours and Company (“Dupont”) and
`
`12.
`
`A.
`
`Archer-Daniels-Midland Company (“ADM”) filed a Petition for Inter Partes
`
`Review (IPR) of all claims of U.S. patent 8,865,921, which is owned by Furanix
`
`Technologies B.V. (“Patent Owner”). The Board instituted this IPR proceeding as
`
`to claims 1–5 and 7–9 of the ’921 patent based only on the following proposed
`
`grounds:
`
`A. Claims 1–5 under 35 U.S.C. § 103(a) as obvious over the
`combination of the ’732 publication (Ex. 1002), RU ’177
`(Ex. 1007), and the ’318 application (Ex. 1008);
`
`B. Claims 7–9 under 35 U.S.C. § 103(a) as obvious over the
`combination of the ’732 publication (Ex. 1002),
`Admitted Prior Art, Lewkowski (Ex. 1005), Oae (Ex.
`1006), RU ’177 (Ex. 1007), and the ’318 application (Ex.
`1008).
`
`Decision (Paper 10) at 21. Regarding “Admitted Prior Art,” I understand that prior
`
`art to be the art specifically discussed in the ’921 patent, which was also raised by
`
`Petitioners: GB 621,971 (Ex. 1019); Partenheimer et al. (Ex. 1003); U.S.
`
`2009/0156841 (Ex. 1022); WO 2007/104515 and WO 2009/030512.
`
`13.
`
`I am informed by counsel that the prior art listed in the preceding
`
`paragraph is the only art upon which the IPR proceeding has been instituted and
`
`-6-
`
`
`
`that to the extent that Dr. Martin addresses additional art, that additional art is not
`
`part of this IPR proceeding. Accordingly, I do not provide an opinion on this
`
`additional art. I have, however, considered certain background art relied on by Dr.
`
`Martin as described below.
`
`B.
`
`2, 5-Furan Dicarboxylic Acid (FDCA) and its production
`
`14.
`
`2, 5-furan dicarboxylic acid (FDCA)1 is a small molecule with the
`
`following chemical structure:
`
`15.
`
`Terephthalic acid (TPA or TA) is large volume global commodity
`
`chemical used in the production of polyester polymers for applications such as
`
`polyester fibers, beverage bottles, and specialty polymers and resins. FDCA is a
`
`furan analog of TPA that may be utilized in place of TPA for the production of
`
`polyester polymers used in a variety of applications. See The Department of
`
`Energy Report, Top Value Added Chemicals from Biomass, 2004, (“the DOE
`
`Report,” Ex. 2005) p. 28.
`
`16. A major advantage of FDCA is that it can be made from HMF and related
`
`
`1 FDCA is also abbreviated “FDA” in certain references, however, except when
`
`quoting those references, I will use the abbreviation FDCA.
`
`-7-
`
`
`
`compounds that are derived from renewable resources. TPA, on the other hand is
`
`petroleum-based. Although FDCA has been known since 1876, as of 2009 there
`
`still was no commercially-viable process for making FDCA with high yield. The
`
`inventors in the ’921 patent describe a process for making FDCA from 5-
`
`hydroxymethyl-furfural (HMF), esters of HMF, and other related compounds. The
`
`inventors describe a process whereby these starting materials are oxidized using a
`
`particular selection of metals (Co and Mn) and a source of bromine as a
`
`homogeneous catalyst, a solvent containing acetic acid, and the combination of a
`
`temperature range and oxygen partial pressure that had not been previously
`
`described. This combination provided previously unheard of FDCA yields when
`
`these homogenous catalyst components are used.
`
`C.
`
`Temperature
`
`17.
`
`The role of temperature in an oxidation reaction is complicated by
`
`multiple, often competing, chemical processes. As temperature increases, the
`
`reaction rate of a chemical reaction also increases. The equation that describes the
`
`relationship between reaction rate for a particular chemical reaction and
`
`temperature is known as the Arrhenius equation. Generally, for each increase of
`
`10°C, the reaction rate doubles. This relationship between reaction rate and
`
`temperature, however, does not mean that an increase in temperature will result in
`
`an increased yield of a desired product.
`
`-8-
`
`
`
`18.
`
`If the temperature is too low, the chemical reaction that leads to the
`
`desired product may not happen at all. An increase in temperature will not lead to
`
`production of the product unless the minimum threshold temperature for the
`
`reaction to occur is met.
`
`19.
`
`In addition, oxidation processes, like the reactions discussed here, involve
`
`multiple chemical reactions that are occurring simultaneously. In addition to
`
`reactions converting the starting material through intermediate compounds to make
`
`the desired product, there are also undesirable side reactions that do not lead to the
`
`desired product. The desired product may itself undergo unwanted reactions or
`
`otherwise degrade. When the reaction temperature is raised, the rates of all of
`
`these reactions are also raised, although not necessarily at the same rate.
`
`D.
`
`Partial Pressure of Oxygen
`
`20.
`
`The oxygen partial pressure is a measure of the amount of oxygen in the
`
`feed gas. Depending on the gas used, the total pressure may be high, but the
`
`oxygen partial pressure may be much lower depending on the percentage of
`
`oxygen in the gas.
`
`21.
`
`In an oxidation reaction, such as the oxidation of HMF and its esters to
`
`FDCA, increasing the oxygen partial pressure in the feed gas would be expected to
`
`increase the reaction rate because the concentration of one of the reactants (O2) is
`being increased. However, as with temperature, an ordinarily skilled artisan would
`
`-9-
`
`
`
`understand that the effects on yield of the desired product by increasing or
`
`decreasing oxygen partial pressure in an oxidation reaction is complicated by the
`
`many reactions that take place and how each of these reactions depend (with
`
`respect to rate) on the oxygen partial pressure.
`
`IV. THE ’921 PATENT
`
`22.
`
`The ’921 patent describes the inventors’ discovery of a combination of
`
`conditions that provide for the production of FDCA at high yields from a feed
`
`stream containing 5-hydroxymethylfurfural (“HMF”), an ester of HMF, and other
`
`related starting materials.
`
`A.
`
`The ’921 Patent Specification
`
`23.
`
`The ’921 patent describes the inventors’ discovery that surprisingly high
`
`FDCA yields can be obtained using a CO/Mn/Br catalyst in an acetic acid solvent
`
`when a reaction temperature above 140°C is used, but as the temperature continues
`
`past 180°C, those higher temperatures “may lead to decarboxylation and to other
`
`degradation products.” ’921 patent (Ex. 1001), col. 4, lines 56-61; col. 2, lines 39-
`
`45.
`
`24.
`
`The ’921 patent specification also discusses the appropriate pressure and
`
`oxygen partial pressure of the inventive processes. See, e.g., col. 4, lines 34- 55.
`
`The specification states that the “pressure of the reaction mixture is preferably
`
`selected such that the solvent is mainly in the liquid phase.” Id., col. 4, lines 39-
`
`-10-
`
`
`
`41. “In practice, this means that pressures between and 100 bar can be used with a
`
`preference for pressures between 10 and 80 bar.” Id., col. 4, lines 41-43.
`
`Regarding the oxygen partial pressure, the ’921 patent states, for example, “In the
`
`case of continuously feeding and removing the oxidant gas to and from the reactor,
`
`the oxygen partial pressure will suitably be between 1 and 30 bar or more
`
`preferably between 1 and 10 bar.” Col. 4, lines 51-55.
`
`25.
`
`The Petitioner wrongly points to the above passages regarding pressure as
`
`discussing the prior art, arguing that the ’921 patent is describing existing
`
`commercial processes. Petition (Paper 1), pp. 11-12. I disagree. It is plain from
`
`the context and language of this part of the specification (including col. 4, lines 34-
`
`55) that it is describing the invention, which can be applied to future commercial
`
`processes. Dr. Martin agreed that this paragraph discusses the pressures that can
`
`be used in the invention and that it does not reference any prior art. Martin Depo.
`
`(Ex. 1027) 108:6-9; 109:2-12.
`
`26.
`
`The ’921 patent also contains three examples, which I discuss in detail
`
`below.
`
`B.
`
`The ’921 Patent Claims
`
`27.
`
`The ’921 patent contains 10 claims which are reproduced below:
`
`1. A method for the preparation of 2,5-furan dicarboxylic
`acid comprising the step of contacting a feed comprising
`a compound selected from the group consisting of 5-
`
`-11-
`
`
`
`hydroxymethylfurfural ("HMF"), an ester of 5-
`hydroxymethylfurfural, 5-methylfurfural, 5-
`(chloromethyl)furfural, 5-methylfuroic acid, 5-
`(chloromethyl)furoic acid, 2,5-dimethylfuran and a
`mixture of two or more of these compounds with an
`oxygen-containing gas, in the presence of an oxidation
`catalyst comprising both Co and Mn, and further a source
`of bromine, at a temperature between 140° C. and 200°
`C. at an oxygen partial pressure of 1 to 10 bar, wherein a
`solvent or solvent mixture comprising acetic acid or
`acetic acid and water mixtures is present.
`
`2. The method according to claim 1, wherein the feed
`comprises a compound selected from the group
`consisting of 5-hydroxymethylfurfural ("HMF"), esters
`of HMF and a mixture thereof.
`
`3. The method according to claim 1, wherein the oxidation
`catalyst comprises at least one additional metal.
`
`4. The method according to claim 3, wherein the additional
`metal is Zr and/or Ce.
`
`5. The method according to claim 1, wherein the
`temperature is between 160 and 190° C.
`
`6. The method according to claim 1, wherein the feed
`comprises an ester of HMF having an ester moiety of an
`
`-12-
`
`
`
`alkyl carboxylic acid wherein the alkyl group has up to 6
`carbon atoms.2
`
`7. A process for the preparation of a dialkyl ester of 2,5,-
`furan dicarboxylic acid, comprising the step of contacting
`a feed comprising a compound selected from the group
`consisting of 5-hydroxymethylfurfural ("HMF"), an ester
`of 5-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 with an
`oxygen-containing gas in the presence of an oxidation
`catalyst comprising both Co and Mn, and further a source
`of bromine, at a temperature between 140° C. and 200°
`C. at an oxygen partial pressure of 1 to 10 bar, wherein a
`solvent or solvent mixture comprising acetic acid or
`acetic acid and water mixtures is present, and esterifying
`the thus obtained product.
`
`8. The process according to claim 7, wherein the product is
`esterified with a C1-C5 alkyl alcohol.
`9. The process according to claim 8, wherein the C1-C5
`alkyl alcohol is methanol and the dialkyl ester is the
`dimethylester of 2,5-furan dicarboxylic acid.
`
`
`I understand that this IPR proceeding will not address claim 6 of the ’921
`2
`
`patent.
`
`-13-
`
`
`
`10. A method according to claim 2, wherein the feed
`comprises an HMF ester and optionally 5-hydroxymethyl
`furfural, which has been obtained by converting a
`carbohydrate source in the presence of an alkyl
`carboxylic acid.3
`
`28.
`
`I understand that claims 1 and 7 are independent claims because they do
`
`not reference other claims. Claim 2, for example, is a dependent claim because it
`
`references claim 1. I understand that a dependent claim contains all of the
`
`elements of the claim from which it depends plus the additional limitations recited
`
`in the dependent claim.
`
`V.
`
`LEGAL STANDARDS
`
`29.
`
`In forming my opinions, I have been asked by Patent Owner’s counsel to
`
`apply the following legal standards.
`
`30. Counsel has informed me that for the purposes of the opinions expressed
`
`in this declaration relating to the non-obviousness/obviousness of the ’921 patent
`
`claims, the proper timeframe in which to apply principles relating to one of
`
`ordinary skill in the art is as of October 7, 2009 (the earliest priority date for the
`
`’921 patent). When I discuss in this declaration that certain things were known by
`
`
`I understand that this IPR proceeding will not address claim 10 of the ’921
`3
`
`patent.
`
`-14-
`
`
`
`one of ordinary skill in the art, the timeframe to which I am referring is prior to
`
`October 2009, unless otherwise stated.
`
`31. With respect to the level of ordinary skill in the art, I understand that
`
`factors such as the education level of those working in the field, the sophistication
`
`of the technology, the types of problems encountered in the art, the prior art
`
`solutions to those problems, and the speed at which innovations are made may help
`
`establish the level of skill in the art. One with ordinary skill has the ability to
`
`understand the technology and make modest adaptations or advances. A person of
`
`ordinary skill in the art is also a person of ordinary creativity, not an automaton.
`
`32.
`
`I understand that a person of ordinary skill in the art provides a reference
`
`point from which the prior art and claimed invention should be viewed. This
`
`reference point prevents one from using his or her own insight or hindsight in
`
`deciding whether a claim would have been obvious.
`
`33. A patent claim is invalid as obvious in view of the prior art if the
`
`differences between the claim and the prior art are such that the claimed subject
`
`matter as a whole would have been obvious to one of ordinary skill in the art at the
`
`time of the invention.
`
`34.
`
`The following factors must be evaluated to determine whether the claimed
`
`invention would have been obvious or not obvious: (1) the scope and content of
`
`the prior art; (2) the difference or differences, if any, between each claim of the
`
`-15-
`
`
`
`patent and the prior art; and (3) the level of ordinary skill in the art at the time the
`
`invention of the patent was made.
`
`35.
`
`In addition to the above factors, the following objective factors
`
`concerning non-obviousness, also known as “secondary considerations,” must also
`
`be considered when present: (1) long-felt but unresolved needs that were satisfied
`
`by the invention of the patent; (2) failure of others to achieve the results of the
`
`invention; (3) commercial success of the claimed invention; (4); copying of the
`
`invention by others in the field; (5) initial expressions of disbelief or skepticism by
`
`experts in the field; (6) praise for the invention by others in the field; and (7)
`
`unexpected results achieved by the invention.
`
`36.
`
`I am informed that objective factors of non-obviousness, such as
`
`unexpected results, must be commensurate in scope with the claims for which the
`
`evidence is offered to support. In other words, the showing of unexpected results
`
`must be reviewed to see if the results occur over the entire claimed range.
`
`However, the nonobviousness of a broader claimed range can be supported by
`
`evidence based on unexpected results from testing a narrower range if one of
`
`ordinary skill in the art would be able to determine a trend in the exemplified data
`
`which would allow the artisan to reasonably extend the probative value of the data
`
`to the claimed range.
`
`-16-
`
`
`
`VI. CONSTRUCTION OF CLAIM TERMS
`
`37.
`
`I am informed by counsel for Patent Owner that a claim term should
`
`receive its broadest reasonable interpretation in light of the patent’s specification,
`
`as one of ordinary skill in the art would interpret it. The broadest reasonable
`
`interpretation does not mean the broadest possible interpretation. Rather, the
`
`meaning given to a claim term must be consistent with the ordinary and customary
`
`meaning of the term, unless the term has been given a special definition in the
`
`patent specification. The meaning given a claim term must be consistent with how
`
`the term is used in the specification. Further, the broadest reasonable interpretation
`
`of the claims must be consistent with the interpretation that those skilled in the art
`
`would reach.
`
`38. Based upon my review of the ’921 patent specification, it is my opinion
`
`that a person of ordinary skill in the art would assign to the terms in the claims the
`
`ordinary and customary meaning of the terms.
`
`39.
`
`I disagree with Dr. Martin’s interpretation of the temperature ranges
`
`recited in claims 1 and 5 of the ’921 patent. See Martin Decl. (Ex. 1009) ¶¶ 53-54.
`
`According to Dr. Martin, the ranges “between 140° C. and 200° C and between
`
`160° C. and 190° C” would include the temperature limits 140°C, 160°C, 190°C
`
`and 200°C.” Id. at ¶ 53.
`
`40.
`
`In my opinion, a person of ordinary skill in the art would understand the
`
`-17-
`
`
`
`claim language reciting temperature ranges to be clear and unambiguous. Claims 1
`
`and 5 recite that the temperature is between the two values. The ordinary and
`
`customary meaning to a person of ordinary skill would have been that this
`
`language means that the values 140°C and 200°C (in claims 1 and 7) and 160°C
`
`and 190°C (in claim 5) are not included in the recited ranges.
`
`41.
`
`The patent specification is consistent with the ordinary and customary
`
`meaning of the temperature ranges that I provide in the previous paragraph. Dr.
`
`Martin states that he “was unable to locate the term ‘between’ in the original
`
`specification.” Martin Decl. (Ex. 1009) ¶ 53. The specification, however, does
`
`recite the term “between” with regards to temperature ranges. For example, the
`
`specification in column 4 recites a preferred temperature range of “between 160
`
`and 190 °C” (col. 4, lines 57-58). In addition, the originally-filed claims, which I
`
`understand are also considered to be part of the patent specification, recite a
`
`temperature range “higher than 140°C” (see Ex. 1011 at page 28 of 629 (original
`
`claim 1)) and dependent claims that limit this range to “between 140 and 200°C”
`
`(id. (original claim 9)).
`
`42. As Dr. Martin admits, a person of ordinary skill in the art would
`
`understand that the temperature range “higher than 140°C” would not include
`
`140°C. See e.g., Martin Depo. (Ex. 1027) 107:5-8. A person of ordinary skill
`
`would also recognize that when this range is narrowed to “between 140 and
`
`-18-
`
`
`
`200°C” as in the original claim 9, it also would not include 140°C. For these
`
`reasons, it is my opinion that the ranges “between 140° C and 200° C” recited in
`
`claims 1 and 7 of the ’921 patent would not include the temperature limits 140°
`
`and 200°C.
`
`43. An ordinarily skilled artisan would also understand that the phrase
`
`“between 160° C. and 190° C,” recited in claim 5, would not include 160°C and
`
`190°C. The artisan would apply the same understanding that “between 160 and
`
`190°C” does not include the endpoints.
`
`VII. THE PRIOR ART RELIED UPON BY PETITIONERS AND DR.
`MARTIN DOES NOT TEACH OR SUGGEST THE CLAIMED
`INVENTION
`
`A.
`
`Person of Ordinary Skill in the Art
`
`44. Dr. Martin describes what he believes to be a person of ordinary skill in
`
`the art in paragraph 14 of his declaration. I disagree with Dr. Martin’s description
`
`of a person of ordinary skill in the art as he has written it in his declaration because
`
`he requires such a person to have a doctorate degree. In my experience,
`
`individuals working in the field often have BS or MS degrees with relevant
`
`experience in the field. Thus, in my opinion, a person of ordinary skill in the art in
`
`2009 would have been a person having at least a bachelor’s degree in chemistry or
`
`chemical engineering, having worked in the field of chemical process development
`
`for at least five years and having experience in the preparation of furan compounds
`
`-19-
`
`
`
`from biomass and in the catalysis of oxidation of furan compounds.
`
`45.
`
`In his deposition, Dr. Martin broadened his definition of a person of
`
`ordinary skill stating that such a person would also include individuals with a
`
`bachelor’s degree or master’s degree in chemistry with appropriate experience in
`
`the field of catalysis. Martin Depo. (Ex. 1027) 112:21-114:2.
`
`46. My opinions provided in this declaration do not change whether Dr.
`
`Martin’s definition of a person of ordinary skill in the art is used or my definition
`
`is used.
`
`B. WO 01/72732 (“the ’732 Publication,” Ex. 1002)
`
`47. WO 01/72732 (“the ’732 publication,” Ex. 1002) does not teach or
`
`suggest the methods of the claimed invention. In particular, the ’732 publication
`
`does not teach or suggest a method for the preparation of FDCA comprising
`
`contacting a feed containing the claimed starting materials with an oxygen-
`
`containing gas, in the presence of an oxidation catalyst comprising both Co and
`
`Mn, and further a source of bromine, at a temperature between 140°C and 200°C at
`
`an oxygen partial pressure of 1 to 10 bar.
`
`(1). The ’732 publication does not teach or suggest an oxygen
`partial pressure of 1 to 10 bar
`
`48.
`
`The ’732 publication does not teach or suggest an oxygen partial pressure
`
`of 1 to 10 bar as recited in the ’921 patent claims. The disclosure in the ’732
`
`publication that “corresponding pressure is such to keep the solvent mostly in the
`
`-20-
`
`
`
`liquid phase” (see p. 7, lines 4-5) would not teach or suggest the claimed oxygen
`
`partial pressure of 1 to 10 bar. Dr. Martin relies on this disclosure in his
`
`declaration. See, e.g., Martin Decl. (Ex. 1009) ¶¶ 66, 91, 94. This disclosure in the
`
`’732 publication relates to the total pressure in the reaction chamber and does not
`
`state the partial pressure of oxygen. Dr. Martin admits this point in his deposition
`
`testimony:
`
`Q. Good afternoon. Let's turn to -- actually, let's turn briefly
`to the 732 publication and specifically page 7, starting at
`line 4.
`
`A. Starting at line --
`
`Q. It states, "The corresponding pressure is such to keep the
`solvent mostly in the liquid phase," and you cite to this
`passage in your declaration. Correct?
`
`A. I did, yes.
`
`Q. Okay. The -- this passage, the sentence I just read relates
`to the total pressure in the chamber. Correct?
`
`A. That’s correct.
`
`Q. Okay. It doesn't relate to the -- any particular amount of
`oxygen that’s present in the chamber?
`
`A. Correct.
`
`Martin Depo. (Ex. 1027) 114:6-115:1.
`
`49.
`
`In addition, Examples 16-40 in the ’732 publication, disclosing the
`
`-21-
`
`
`
`reaction of HMF to CFF and FDCA, used an oxygen partial pressure that is about
`
`45% higher than the upper limit of the claimed range. Those examples use air at
`
`1000 psi, which converts to 69 bar air, or a partial pressure of oxygen of 14.5 bar.
`
`(2). The ’732 publication would not have motivated an
`ordinarily skilled artisan to employ a temperature in the
`claimed ranges
`
`50.
`
`The ’732 publication states that “for preparation of the diacid, the
`
`preferred temperatures are about 50° to 250°C, most preferentially about 50° to
`
`160°C.” ’732 publication (Ex. 1002), p. 7, lines 2-4. This statement does not
`
`disclose the range recited in claim 1 (between 140 and 200°C) or in claim 5
`
`(between 160 and 190°C). As discussed below, the examples in the ’732
`
`publication describing the conversion of HMF to FDCA provide reaction
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`temperatures of 100°C, 105°C, and 125°C, with the highest FDCA yields obtained
`
`at 105°C. In addition, the ’732 publication examples include staged reactions
`
`performed at 75°C for two hours and 150°C for two hours. However, as I discuss
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`below, a person of ordinary skill in the art would understand that the reaction at
`
`150°C in these examples did not contain HMF, because it was converted to other
`
`compounds before the reaction reached 150°C.
`
`51. Dr. Martin incorrectly states that the ’732 publication would have
`
`provided to a person of ordinary skill in the art the motivation to use increased
`
`temperatures. Martin Decl. (Ex. 1009) ¶ 65. Specifically, Dr. Martin states:
`
`-22-
`
`
`
`it would be predicted by one of ordinary skill in the art
`that increasing the temperature of an incomplete reaction
`would drive the reaction toward increased yield of the
`final product FDCA.
`
`Id. (comparing staged reactions to 12 hour reactions). Dr. Martin’s conclusions,
`
`however, are not supported by the data he cites. Examples 38-40 of the ’732
`
`publication demonstrate that the staged reactions with 2 hours at 75°C and 2 hours
`
`at 150°C have some of the highest levels of CFF intermediate. Reactions
`
`performed at lower temperatures, 105°C and 125°C, generally have lower amounts
`
`of CFF. ’732 publication (Ex. 1002), p. 15 (see, e.g., examples 22, 32, and 33).
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`Thus, contrary to Dr. Martin’s assertions, the staged reactions (with 2 hours at
`
`150°C) have more of the CFF intermediate than many reactions at lower
`
`temperatures. A person of ordinary skill in the art would therefore not have
`
`concluded based on the data in the ’732 publication that increased temperature
`
`would drive the reaction toward increased yield of the desired FDCA.
`
`52. Dr. Martin also states in his declaration:
`
`The ‘732 publication data similarly conveys an
`expectation to one of ordinary skill in the art that
`increasing the oxidation temperature would
`contemporaneously increase yield of a catalytically
`oxidized heterocyclic furan precursor.
`
`See Martin Decl. (Ex. 1009) ¶ 92. I disagree. To make his point, Dr. Martin
`
`-23-
`
`
`
`cherry picks from the ’732 publication, specifically from Table 4. In paragraph 92
`
`of his report, Dr. Martin selects reactions showing “increasing FDCA yield with a
`
`temperature change from 100°C to 125°C.” Id. However, increasing the
`
`temperature does not necessarily increase yield as demonstrated by Table 4 of the
`
`’732 publication, relied on by Dr. Martin. For example, comparing examples 20
`
`and 25, and examples 19 and 24 (reproduced below) from Table 4 of the ’732
`
`publication, shows that in some instances increasing the reaction temperature from
`
`100 to 125°C has little or no effect on yield, and may even decrease yield of
`
`FDCA.
`
`In addition, a comparison of Example 17 and 35 (reproduced below) would
`
`indicate that an increase of 5°C from 100 to 105°C could cause a significant
`
`reduction in FDCA yield.
`
`-24-
`
`
`
`Thus, a person of ordinary skill in the art would understand that the effect of
`
`increasing temperature on FDCA yield is unpredictable and does not necessarily
`
`lead to increased FDCA yield as Dr. Martin states.
`
`53. A person of ordinary skill in the art when considering the ’732 publication
`
`would have understood that the optimal temperature for the conversion of HMF to
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`FDCA is around 105°C. The highest FDCA yields recited the ’732 publication,
`
`58.8%, was achieved at a reaction temperature of 105°C (see Table 4, Example 28,
`
`reproduced below), and not at the higher temperature of 125°C or in the staged
`
`reactions performed at 75°C and 150°C.
`
`54. Dr. Martin
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