IN THE UNITED STATES PATENT AND TRADEMARK OFFICE
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`
`
`HYDRITE CHEMICAL CO.
`Petitioner
`
`v.
`
`SOLENIS TECHNOLOGIES, L.P.
`Patent Owner
`
`
`
`Case IPR2015-_____
`
`U.S. Patent No. 8,962,059
`
`PETITION
`
`FOR
`
`INTER PARTES REVIEW
`
`OF
`
`U.S. PATENT NO. 8,962,059
`
`
`
`
`
`
`
`
`
`
`
`

`
`TABLE OF CONTENTS
`
`TABLE OF CONTENTS
`
`I.
`
`1.
`
`EXHIBIT LIST ........................................................................................... IV
`
`EXHIBIT LIST ......................................................................................... .. IV
`
`II. MANDATORY NOTICES ........................................................................ IX
`
`II. MANDATORY NOTICES ...................................................................... .. IX
`
`A.
`
`A.
`
`B.
`
`B.
`
`C.
`
`C.
`
`D.
`
`D.
`
`REAL PARTY-IN-INTEREST ......................................................................... IX
`
`REAL PARTY-IN-INTEREST ....................................................................... .. IX
`
`RELATED MATTERS .................................................................................... IX
`
`RELATED MATTERS .................................................................................. .. IX
`
`LEAD AND BACK-UP COUNSEL .................................................................... X
`
`LEAD AND BACK-UP COUNSEL .................................................................. .. X
`
`SERVICE INFORMATION .............................................................................. XI
`
`SERVICE INFORMATION ............................................................................ .. XI
`
`III. GROUNDS FOR STANDING ...................................................................... 1
`
`III. GROUNDS FOR STANDING .................................................................... ..1
`
`IV. THE ’059 PATENT IN CONTEXT ............................................................. 1
`
`THE ’059 PATENT IN CONTEXT ........................................................... ..1
`
`IV.
`
`V.
`V.
`
`PRECISE RELIEF REQUESTED .............................................................. 6
`PRECISE RELIEF REQUESTED ............................................................ ..6
`
`A.
`
`A.
`
`B.
`B.
`
`C.
`C.
`
`CLAIM CONSTRUCTION ................................................................................. 6
`
`CLAIM CONSTRUCTION ............................................................................... ..6
`
`GROUND 1: CLAIMS 1–5 AND 9 ARE OBVIOUS IN VIEW OF WINSNESS,
`GROUND 1: CLAIMS 1-5 AND 9 ARE OBVIOUS IN VIEW OF WINSNESS,
`ALTHER, MARTIN, AND ICI .......................................................................... 8
`ALTHER, MARTIN, AND ICI ........................................................................ ..8
`
`GROUND 2: CLAIMS 13–16 ARE OBVIOUS IN VIEW OF WINSNESS, ALTHER,
`GROUND 2: CLAIMS 13-16 ARE OBVIOUS IN VIEW OF WINSNESS, ALTHER,
`MARTIN, ICI, AND BUCHOLD ...................................................................... 23
`MARTIN, ICI, AND BUCHOLD .................................................................... ..23
`
`D. GROUND 3: CLAIMS 6 AND 7 ARE OBVIOUS IN VIEW OF WINSNESS, ALTHER,
`D.
`GROUND 3: CLAIMS 6 AND 7 ARE OBVIOUS IN VIEW OF WINSNESS, ALTHER,
`MARTIN, ICI, AND SCHEIMANN .................................................................. 36
`MARTIN, ICI, AND SCHEIMANN ................................................................ ..36
`
`E.
`E.
`
`F.
`F.
`
`GROUND 4: CLAIM 8 IS OBVIOUS IN VIEW OF WINSNESS, ALTHER, MARTIN,
`GROUND 4: CLAIM 8 IS OBVIOUS IN VIEW OF WINSNESS, ALTHER, MARTIN,
`ICI, SCHEIMANN, AND MUKERJEE .............................................................. 38
`ICI, SCHEIMANN, AND MUKERJEE ............................................................ ..3 8
`
`GROUND 5: CLAIMS 10 AND 12 ARE OBVIOUS IN VIEW OF WINSNESS,
`GROUND 5: CLAIMS 10 AND 12 ARE OBVIOUS IN VIEW OF WINSNESS,
`ALTHER, MARTIN, ICI, AND BONANNO ...................................................... 42
`ALTHER, MARTIN, ICI, AND BONANNO .................................................... ..42
`
`G. GROUND 6: CLAIM 11 IS OBVIOUS IN VIEW OF WINSNESS, ALTHER, MARTIN,
`G.
`GROUND 6: CLAIM 11 IS OBVIOUS IN VIEW OF WINSNESS, ALTHER, MARTIN,
`ICI, BONANNO, AND DAVID ........................................................................ 46
`ICI, BONANNO, AND DAVID ...................................................................... ..46
`ii
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`ii
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`
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`

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`H.
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`GROUND 7: CLAIMS 1 AND 6 ARE OBVIOUS IN VIEW OF BONANNO AND ICI
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`H. GROUND 7: CLAIMS 1 AND 6 ARE OBVIOUS IN VIEW OF BONANNO AND ICI
` ................................................................................................................... 47
`
`................................................................................................................. ..47
`
`I.
`I.
`
`J.
`J.
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`GROUND 8: CLAIMS 2, 3, AND 10 ARE OBVIOUS IN VIEW OF BONANNO, ICI,
`GROUND 8: CLAIMS 2, 3, AND 10 ARE OBVIOUS IN VIEW OF BONANNO, ICI,
`AND MARTIN .............................................................................................. 53
`
`AND MARTIN ............................................................................................ ..53
`
`GROUND 9: CLAIM 11 IS OBVIOUS IN VIEW OF BONANNO, ICI, MARTIN, AND
`GROUND 9: CLAIM 11 IS OBVIOUS IN VIEW OF BONANNO, ICI, MARTIN, AND
`DAVID ......................................................................................................... 58
`
`DAVID ....................................................................................................... ..58
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`VI. SUMMARY .................................................................................................. 59
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`SUMMARY ................................................................................................ ..59
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`VI.
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`
`
`
`
`
`
`iii
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`iii
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`

`
`EXHIBIT LIST
`
`I.
`The following Exhibit List is provided in accordance with 37 C.F.R. § 42.63(e):
`
`EXHIBIT LIST
`
`Number
`
`Brief Description
`
`1001
`
`1002
`
`1003
`
`1004
`
`U.S. Patent No. 8,962,059
`
`(“’059 Patent”)
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`Prosecution History of U.S. Patent No. 8,962,059
`
`(“’059 Prosecution”)1
`
`Assignment Records of U.S. Patent No. 8,962,059
`
`(“’059 Assignment Records”)
`
`Superior Oil Company, Inc. v. Solenis Technologies
`
`L.P., United States District Court for the District of
`
`Delaware, C.A. No. 15-0183-GMS, Notice of
`
`Dismissal, June 11, 2015 (“Interference Dismissal”)
`
`
`1 As available from PAIR.
`
`
`
`iv
`
`

`
`EXHIBIT LIST
`
`Number
`
`Brief Description
`
`Declaration of David A. Rockstraw, Ph.D., P.E.
`
`1005
`
`1006
`
`(“Rockstraw Decl.”)
`
`U.S. Patent No. 4,702,798
`
`(“Bonanno”)
`
`George Alther, “Put the Breaks On,” Chemical
`
`1007
`
`Engineering, Vol. 5, No. 3 (March 1998)
`
`(“Alther”)
`
`“The HLB System a time-saving guide to emulsifier
`
`1008
`
`selection,” ICI Americas Inc. (March 1980)
`
`(“ICI”)
`
`
`
`v
`
`

`
`EXHIBIT LIST
`
`Number
`
`Brief Description
`
`1009
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`1010
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`1011
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`1012
`
`1013
`
`Pasupati Mukerjee and Karol J. Mysels, “Critical
`
`Micelle Concentrations of Aqueous Surfactant
`
`Systems,” Nat. Stand. Ref. Data Ser., Nat. Bur. Stand.
`
`(Feb. 1971) (“Mukerjee”)
`
`U.S. Patent No. 5,283,322
`
`(“Martin”)
`
`U.S. Patent No. 5,558,781
`
`(“Buchold”)
`
`U.S. Patent Application Pub. No. 2008/0110577
`
`(“Winsness”)
`
`U.S. Patent No. 7,309,602
`
`(“David”)
`
`
`
`vi
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`

`
`EXHIBIT LIST
`
`Brief Description
`
`U.S. Patent Application Pub. No. 2007/0210007
`
`Number
`
`1014
`
`(“Scheimann”)
`
`Dictionary.com,
`
`1015
`
`http://dictionary.reference.com/browse/aqueous,
`
`definition of “aqueous,” last accessed July 12, 2015
`
`(“Aqueous”)
`
`McCutcheon’s Division, “McCutcheon’s Volume 1:
`
`1016
`
`Emulsifiers & Detergents North American Edition,” p.
`
`211 (1997) (“McCutcheon’s”)
`
`International Union of Pure and Applied Chemistry,
`
`1017
`
`“Compendium of Chemical Terminology,” Second
`
`Edition, pp. 16, 166 (1997) (“IUPAC”)
`
`
`
`vii
`
`

`
`EXHIBIT LIST
`
`Number
`
`Brief Description
`
`1018
`
`IUPAC-IUB Commission on Biochemical
`
`Nomenclature, “The Nomenclature of Lipids,”
`
`Biochem J., Vol. 171, Issue 1, pp. 21–35 (April 1978)
`
`(“Biochem”)
`
`Vigen K. Babayan, “Specialty Lipids and Their
`
`1019
`
`Biofunctionality,” LIPIDS, Vol. 22, No. 6, pp. 417–20
`
`(1987) (“Babayan”)
`
`1020
`
`1021
`
`
`
`
`
`
`
`Food and Drugs, 21 C.F.R. § 172.840, “Polysorbate
`
`80” (2015) (“F&D § 840”)
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`Food and Drugs, 21 C.F.R. § 573.860, “Polysorbate
`
`80” (2015) (“F&D § 860”)
`
`
`
`viii
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`

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`II. MANDATORY NOTICES
`
`As required under 37 C.F.R. § 42.8, the following mandatory notices are
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`filed with the Patent Trial and Appeal Board (“Board”).
`
`A. Real Party-In-Interest
`The real parties-in-interest, pursuant to 37 C.F.R. § 42.8(b)(1), include (i)
`
`
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`Hydrite Chemical Co., having a principal office at 300 North Patrick Boulevard,
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`Brookfield, Wisconsin 53045, (ii) Hydrite Chemical International Co., having a
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`principal office at 300 North Patrick Boulevard, Brookfield, Wisconsin 53045, and
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`(iii) Hydrite Advanced Resins LLC, having a place of business at 114 North Main
`
`Street, Cottage Grove, Wisconsin 53527.
`
`B. Related Matters
`United States Patent No. 8,962,059 (“’059 Patent”) is the subject of
`
`
`
`litigation in the United States District Court for the Eastern District of Wisconsin
`
`filed on July 14, 2015, between plaintiff Hydrite Chemical Co. and defendants
`
`Solenis Technologies, L.P and Solenis, LLC.
`
`U.S. patent application nos. 14/627,618 and 14/628,662 claim the benefit of
`
`the ’059 Patent.
`
`The ’059 Patent was also the subject of an interference proceeding filed by
`
`Superior Oil Company, Inc. (“Superior”) against Solenis Technologies L.P., which
`
`was dismissed with prejudice by Superior on June 11, 2015. See Ex. 1004.
`
`Superior sought adjudication of an interference between the ’059 Patent and United
`ix
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`

`
`States Patent No. 8,841,469 (“’469 Patent”). The ’469 Patent and the ’059 Patent
`
`are believed to now be commonly owned by Solenis Technologies L.P. See Ex.
`
`1003 (assigning the ’059 Patent from Superior to Solenis Technologies L.P.).
`
`Petitioner further believes that the ’469 Patent is the subject of litigation in
`
`the United States District Court for the Western District of Tennessee (Case No.
`
`2:15-cv-02063) filed under seal on January 23, 2015, between plaintiff Buckman
`
`Laboratories, Inc. and defendants Solenis Technologies, L.P. and Solenis, LLC.
`
`Lastly, the ’469 Patent is both subject to a petition for inter partes review
`
`and litigation in the United States District Court for the Eastern District of
`
`Wisconsin, which are concurrently filed by Hydrite Chemical Co.
`
`The above matters may be affected by a decision in this proceeding.
`
`C. Lead and Back-Up Counsel
`Lead and back-up counsel for the instant proceeding are:
`
`Lead Counsel
`
`Back-Up Counsel
`
`Richard Roche
`
`Joel Austin
`
`Reg. No. 38,599
`
`Reg. No. 59,712
`
`Attorney for Petitioner
`
`Attorney for Petitioner
`
`richard.roche@quarles.com
`
`joel.austin@quarles.com
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`x
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`QUARLES & BRADY LLP
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`QUARLES & BRADY LLP
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`411 East Wisconsin Avenue
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`411 East Wisconsin Avenue
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`Suite 2350
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`Suite 2350
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`Milwaukee, Wisconsin 53202
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`Milwaukee, Wisconsin 53202
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`Tel: (414) 277-5805
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`Tel: (414) 277-5617
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`
`
`A power of attorney appointing the above lead and back-up counsel
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`accompanies this Petition.
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`Service Information
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`D.
`Service information is as follows, with the postal mailing address being
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`
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`identical to the hand-delivery address:
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`QUARLES & BRADY LLP
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`c/o Richard Roche
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`richard.roche@quarles.com
`
`411 East Wisconsin Avenue
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`Suite 2350
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`Milwaukee, Wisconsin 53202
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`Tel: (414) 277-5805
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`Service via email to richard.roche@quarles.com, joel.austin@quarles.com,
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`and christopher.fahy@quarles.com is acceptable.
`xi
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`

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`
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`III. GROUNDS FOR STANDING
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`Petitioner certifies that United States Patent No. 8,962,059 (“’059 Patent”) is
`
`available for inter partes review having been filed on May 27, 2011, and that
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`Petitioner is not barred or estopped from requesting this inter partes review of
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`Claims 1–16 of the ’059 Patent on the Grounds identified in this Petition.
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`IV. THE ’059 PATENT IN CONTEXT
`The ’059 Patent is directed to a method of “extracting oil from a byproduct
`
`stream of a bio-based ethanol production process” including “applying an oil
`
`concentrator to a byproduct stream.” Ex. 1001, Abs. The claims of the ’059 Patent
`
`attempt to cover “extracting oil” with the use of a commercially available “oil
`
`concentrator.” Ex. 1001, 13:25–31, 14:28–38. Despite the use of chemical
`
`verbiage in the claims, and as described below in detail, the claims of the ’059
`
`Patent encompass what was known, with each aspect predictably behaving exactly
`
`as one of skill would have expected. See, e.g., Ex. 1005, ¶¶ 10–21, 41–176.
`
`As stated in the ’059 Patent, “[o]il from the byproduct stream of the bio-
`
`based production of ethanol may be a secondary product stream providing
`
`additional value to the overall process, so long as the cost of obtaining the oil is
`
`below the value derived.” Ex. 1001, 1:54–57 (emphasis added). Furthermore, “the
`
`byproduct streams may provide an important and significant revenue stream that
`
`provides additional economic incentive for production growth.” Ex. 1001, 1:69–
`
`1
`
`

`
`
`
`62.
`
`According to the ’059 Patent, the “dry grind ethanol production process,
`
`using corn, is presently the primary source of ethanol in the United States.” Ex.
`
`1001, 1:15–17. “In one popular method of removing the oil from the byproduct
`
`stream, mechanical forces are used to separate the oil from thin stillage,” such as
`
`evaporation, heating under pressure, and centrifuging. Ex. 1001, 2:25–34.
`
`Moreover, the ’059 Patent acknowledges “[o]ther known solutions for back-end
`
`recovery [of oil] include solvent extraction methods.” Ex. 1001, 13:1–2.
`
`With this as context, the ’059 Patent contends that the “present invention
`
`involves a method of extracting oil from a byproduct stream” using an “oil
`
`concentrator” (i.e., ethoxylated sorbitan ester or polyoxyethylene (20) sorbitan
`
`ester) that “reduces interactions between the oil and oil sequestering components . .
`
`. facilitating extraction of the oil from the byproduct stream.” Ex. 1001, 2:57–64,
`
`13:27–28, 14:36–37. The ’059 Patent declares that the Applicants discovered two
`
`concepts. First, “it was discovered that an oil concentrator may be used to enhance
`
`oil recovery.” Ex. 1001, 5:34–35. Second, it “was discovered that the hydrophile-
`
`lipophile balance (HLB) of a particular compound was a useful indicator for its
`
`efficacy as an oil concentrator.” Ex. 1001, 6:9–11.
`
`While these may have been “discoveries” to the Applicants, to one of
`
`ordinary skill “the use of surfactants to enhance oil recovery from various matrices
`
`2
`
`

`
`
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`is well known in the chemical arts.” Ex. 1002, pp. 182–83 (statement of the ex
`
`parte examiner in the first Office Action issued August 2, 2012); Ex. 1005, ¶¶ 10–
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`21, 53, 78–88. One of skill “would use standard methods in the art such as
`
`determining HLB criteria for optimal emulsion formation and subsequent
`
`demulsification; and optimal surfactant concentrations to ensure that the surfactant
`
`concentration is below a critical micellar concentration (CMC) for the surfactant in
`
`the liquid byproduct stream.” Ex. 1002, p. 183 (emphasis added); Ex. 1005, ¶¶ 10–
`
`21, 54–59, 68–72, 77–88, 132–138.
`
`Even the discussion set forth in the ’059 Patent underscores the fundamental
`
`nature of what the ’059 Patent boldly declares the Applicants had “discovered.”
`
`The ’059 Patent notes that the “HLB requirement for corn oil in water has been
`
`determined to be 10. Thus, a surfactant having a HLB of 10 is likely to form a
`
`stable emulsion of corn oil in water.” Ex. 1001, 6:48–51 (emphasis added). What
`
`is not explicitly stated, but confirmed by common knowledge and sense, is that a
`
`surfactant not having a HLB of 10 is likely to form an unstable emulsion of corn
`
`oil in water. Ex. 1005, ¶¶ 18, 68–72, 84–86.
`
`In purporting to support the Applicants’ “discovery,” the ’059 Patent
`
`describes a series of tests during which “a number of commercially available
`
`surfactants” (each having an HLB value) were tested to determine which will
`
`function as an “oil concentrator” when mixed with “liquid stillage obtained from a
`
`3
`
`

`
`
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`dry mill ethanol production facility using corn as the source material.” Ex. 1001,
`
`8:44–9:25. Not surprisingly, the tests confirmed what was known—surfactants
`
`with an HLB “in the range of 10” each “showed lower oil recovery than the
`
`benchmark, indicating that these surfactants contributed to the formation of stable
`
`emulsions,” whereas surfactants with an HLB not in the range of 10 (e.g., 13.1, 15,
`
`etc.) are “oil concentrators [that] increased the volume of oil recoverable from the
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`stillage.” Ex. 1001, 10:4–28, Table 1; Ex. 1005, ¶¶ 18, 68–72, 84–86.
`
`Despite the above, the ’059 Patent issued and included independent Claims 1
`
`and 13. Notably, none of the claims in the ’059 Patent actually claim any
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`improvement in the methods of oil extraction. The independent claims generally
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`require mixing an “oil concentrator,” limited to an “ethoxylated sorbitan ester” in
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`Claim 1 and a “polyoxyethylene (20) sorbitan ester” in Claim 13. For example,
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`Claim 1 states:
`
`A method of extracting oil from a byproduct stream of a bio-based
`ethanol production process, comprising:
`mixing an ethoxylated sorbitan ester with the byproduct
`stream;
`centrifuging the mixture of the ethoxylated sorbitan ester and
`the byproduct stream; and
`separating the oil from the mixture.
`Ex. 1001, 13:25–31 (emphasis added).
`
`These claimed “oil concentrators” (i.e., ethoxylated sorbitan ester and
`
`4
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`

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`
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`polyoxyethylene (20) sorbitan ester), as confirmed by the ’059 Patent itself, are
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`nothing more than commercially available surfactants. Ex. 1001, 8:21–23, 8:44–
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`48, Table 1; Ex. 1005, ¶¶ 10–21; 68–72, 75.
`
`
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`The ’059 Patent accurately discloses that (1) extracting oil from a byproduct
`
`stream of a bio-based ethanol production process was not new, (2) that there
`
`existed a desire to extract increasing amounts of corn oil from a byproduct stream,
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`and (3) that “oil concentrators” are commercially available. However, in an
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`attempt to support patentability, the ’059 Patent mischaracterized the known result
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`of adding an “oil concentrator” to a byproduct stream as a “discovery.” Ex. 1005,
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`¶¶ 10–21. The ’059 Patent uses a known “oil concentrator” in a known process to
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`achieve a known, predictable, and desired result. Ex. 1005, ¶¶ 10–21, 41–176.
`
`The ’059 Patent presents no “discovery” to one of ordinary skill. Ex. 1005, ¶¶ 10–
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`21, 41–176.
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`As will be described in detail throughout this Petition, the claims of the ’059
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`Patent are unpatentable over the prior art. For instance, Winsness recognized that
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`“efforts to recover usable oil from the byproducts of the dry milling process used
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`to create ethanol have not been terribly successful in terms of efficiency.” Ex.
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`1012, ¶ 7. Winsness specifically identified that the processing of “thin stillage” in
`
`a “centrifuge creates an emulsion phase that typically requires further processing
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`before useable oil can be recovered.” Ex. 1012, ¶ 7. Alther taught that “[s]ome of
`
`5
`
`

`
`
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`the havoc caused by emulsions can be avoided if emulsions are broken.” Ex. 1007,
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`p. 82, col. 1, ¶ 4. In addition, Alther taught that emulsion breakers (i.e., chemical
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`“oil concentrators”) can be added to a centrifugal separator. Ex. 1007, p. 86, col.
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`1, ¶¶ 5–6. Alther taught that “a strongly hydrophilic surfactant, such as
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`Polysorbate 80 [(i.e., a chemical “oil concentrator” commercially available as
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`TWEEN 80)] . . . can break the emulsion.” Ex. 1007, p. 83, col. 2, ¶ 5. Lastly, ICI
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`taught the HLB value of corn oil, and the increasing likelihood that a chemical “oil
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`concentrator,” such as a TWEEN ethoxylated sorbitan ester, with an HLB value
`
`greater than the HLB of corn oil will demulsify the mixture. Ex. 1008, pp. 2, 6
`
`(Table 2A), 13 (Figures 3 and 4).
`
`The prior art as understood by one of ordinary skill establishes more than a
`
`reasonable likelihood that each of Claims 1–16 of the ’059 Patent are unpatentable.
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`V.
`
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`PRECISE RELIEF REQUESTED
`
`Petitioner requests Claims 1–16 of the ’059 Patent be found unpatentable as
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`obvious under 35 U.S.C. § 103 for the reasons set forth in the following Grounds,
`
`which reference the noted patents and printed publications, in combination with the
`
`expert declaration testimony of David A. Rockstraw, Ph.D., P.E. (Ex. 1005).
`
`A. Claim Construction
`Claims 1–16 of the ’059 Patent are given their “broadest reasonable
`
`
`
`construction in light of the specification.” See 37 C.F.R. § 42.100(b). While Dr.
`
`6
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`

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`
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`Rockstraw includes a concise primer of certain chemical terms and concepts as
`
`understood by one of ordinary skill, Petitioner does not believe that any term in
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`Claims 1–16 requires a formal construction, except for the phrase “adding the oil
`
`concentrator” as used in Claim 8. See, e.g., Ex. 1005, ¶ 132.
`
`
`
`When given the broadest reasonable interpretation in view of the ’059
`
`Patent’s specification, the phrase “adding the oil concentrator” means “mixing the
`
`ethoxylated sorbitan ester.” Ex. 1005, ¶ 132. For completeness, the additional
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`occurrences of the phrase “oil concentrator” in Claim 8 mean “ethoxylated sorbitan
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`ester.” Ex. 1005, ¶ 132. This interpretation is consistent with the language of
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`Claim 1 and is confirmed by the prosecution history.
`
`Claim 8 provides no antecedent basis for the phrase “oil concentrator” found
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`in the step of “wherein adding . . . into . . . the byproduct stream.” However,
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`referring to Claim 1, from which Claim 8 ultimately depends, clarifies that the step
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`of “adding” in Claim 8 is referring to the step of “mixing an ethoxylated sorbitan
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`ester with the byproduct stream” of Claim 1. Therefore, coherency compels the
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`phrase “adding the oil concentrator” of Claim 8 to mean “mixing the ethoxylated
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`sorbitan ester.”
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`The prosecution history of the ’059 Patent confirms this interpretation.
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`Claim 8 is an original, unamended claim. Ex. 1002, p. 216. During prosecution,
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`the claim from which Claim 8 originally depended was canceled. Ex. 1002, pp.
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`7
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`
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`48–49. The dependency of Claim 8 was changed to issued Claim 1 (original Claim
`
`18). Ex. 1002, pp. 48–49. However, the terminology of Claim 8 was not amended
`
`concurrently and therefore became inconsistent with issued Claim 1—resulting in
`
`the current disconnect between Claim 1 and Claim 8. The Applicants stated that
`
`issued Claim 1 was “similar in scope to” the canceled claim, but “is more specific
`
`as to the additive used to facilitate separation of oil from the bio-based byproduct
`
`stream, reciting an ethoxylated sorbitan ester.” Ex. 1002, p. 166. Therefore,
`
`Applicants intended to narrow the scope of dependent Claim 8 by limiting the
`
`originally claimed “oil concentrator” to “ethoxylated sorbitan ester.” The broadest
`
`reasonable construction (and conclusion) is that “adding the oil concentrator” as
`
`used in Claim 8 means “mixing the ethoxylated sorbitan ester.”
`
`One of ordinary skill is considered to be a person who has, among other
`
`attributes, obtained a chemical engineering degree and accrued about five years of
`
`practical experience in design and application of chemical processes, such as corn
`
`to ethanol production and similar processes. See, e.g., Ex. 1005, ¶ 25.
`
`B. Ground 1: Claims 1–5 and 9 are obvious in view of Winsness,
`Alther, Martin, and ICI
`
`Claim
`1. A method of
`extracting oil from
`a byproduct stream
`of a bio-based
`ethanol production
`process,
`
`Specific Reference to Prior Art
` Winsness teaches “a method of recovering oil from a
`byproduct resulting from the production of ethanol from
`corn.” Ex. 1012, ¶ 39. Winsness teaches mechanically
`separating thin stillage from whole stillage using a
`centrifuge. Ex. 1012, ¶ 43. Winsness teaches concentrating
`the thin stillage to syrup, and centrifuging the syrup to
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`recover oil. Ex. 1012, ¶ 44.
` Alther teaches that “[s]ome of the havoc caused by
`emulsions can be avoided if emulsions are broken.” Ex.
`1007, p. 82, col. 1, ¶ 4. Alther further teaches that
`centrifugal separators use centrifugal force to separate oil
`from water and that emulsion breakers can be added to a
`centrifugal separator. Ex. 1007, p. 86, col. 1, ¶¶ 5–6. Alther
`also teaches that Polysorbate 80 can break an emulsion. Ex.
`1007, p. 83, col. 2, ¶ 5.
` Martin teaches “oxyalkylated sorbitan fatty esters.
`Representative surfactants are those surfactants marketed by
`ICI Americas Inc., under the trademark ‘Tween’ label. The
`‘Tween’ label surfactants are polyoxyethylene 20 sorbitan R
`surfactants with R being a fatty acid moiety. . . . When R
`equals monooleate the material is ‘Tween’ 80 (polysorbate
`80).” Ex. 1010, 2:47–66.
`
`
`
`comprising:
` mixing an
`ethoxylated
`sorbitan ester with
`the byproduct
`stream;
` centrifuging the
`mixture of the
`ethoxylated
`sorbitan ester and
`the byproduct
`stream; and
` separating the oil
`from the mixture.
`
`
`
`Claim 1 covers a method of mixing a known commercially available
`
`chemical into a known process to achieve a known (and desirable) result.
`
`Winsness teaches both a method of extracting oil from a byproduct stream and
`
`explicitly recognizes a problem with the method. Alther demonstrates a known
`
`solution to the recognized problem in Winsness, and Martin and ICI provide
`
`additional support that the specific solutions would have worked as expected. In
`
`addition, overall market demands and incentives were driving increased
`
`efficiencies and oil recovery in the bio-based ethanol production industry. Ex.
`
`1005, ¶¶ 10–21, 53–59, 78–88.
`
`
`
`Winsness teaches “a method of recovering oil from a byproduct resulting
`
`from the production of ethanol from corn.” Ex. 1012, ¶ 39. Winsness recognized
`
`that “efforts to recover usable oil from the byproducts of the dry milling process
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`
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`used to create ethanol have not been terribly successful in terms of efficiency.”
`
`Ex. 1012, ¶ 7. A problem with one previous approach is that the spinning of thin
`
`stillage using a centrifuge creates an emulsion phase that requires further
`
`processing. Ex. 1012, ¶ 7. Thus, at the time of the ’059 Patent, Winsness had
`
`recognized a problem caused by the creation of an emulsion phase in a centrifuge
`
`used to extract oil from the byproduct stream of a bio-based ethanol production
`
`process. Ex. 1005, ¶¶ 13–14, 53, 78–88.
`
`
`
`Alther teaches that “[s]ome of the havoc caused by emulsions can be
`
`avoided if emulsions are broken.” Ex. 1007, p. 82, col. 1, ¶ 4. Alther further
`
`teaches that centrifugal separators use centrifugal force to separate oil from water
`
`and that emulsion breakers can be added to a centrifugal separator. Ex. 1007, p.
`
`86, col. 1, ¶¶ 5–6. In addition, Alther teaches that Polysorbate 80 can break an
`
`emulsion. Ex. 1007, p. 83, col. 2, ¶ 5. Thus, at the time of the ’059 Patent, Alther
`
`had disclosed an identified, predictable potential solution (i.e., mix in Polysorbate
`
`80 to a centrifuge being used to separate oil from water) to the problem (i.e., the
`
`creation of an emulsion phase in a centrifuge) recognized by Winsness. Ex. 1005,
`
`¶¶ 13–15, 53–59, 78–88.
`
`
`
`Claim 1 recites “mixing an ethoxylated sorbitan ester with the byproduct
`
`stream.” Ex. 1001, 13:27–28. As noted, Alther teaches the use of Polysorbate 80
`
`to break an emulsion. Ex. 1007, p. 83, col. 2, ¶ 5. Martin further describes the use
`
`10
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`

`
`
`
`and selection of a series of polyoxyethylene 20 sorbitan fatty esters for the
`
`dewatering of the crude materials obtained in the processing of corn. Ex. 1010,
`
`2:32–4:40; Ex. 1005, ¶¶ 16, 61–62, 80. Martin recognizes the advantage of an
`
`appropriately selected surfactant on the ability to separate an aqueous liquid phase
`
`from an organic liquid phase in the presence of solids that act to form an emulsion.
`
`Ex. 1010, 2:12–16, 4:37–40; Ex. 1005, ¶¶ 16, 61–62, 80. Martin teaches the use of
`
`oxyalkylated sorbitan fatty esters [such as] . . . those surfactants
`marketed by ICI Americas Inc., under the trademark “Tween” label.
`The “Tween” label surfactants are polyoxyethylene 20 sorbitan R
`surfactants with R being a fatty acid moiety. . . . When R equals
`monooleate the material is “Tween” 80 (polysorbate 80).
`Ex. 1010, 2:47–66.
`
`The term ethoxylate can also be used as a noun or verb. The noun ethoxylate
`
`refers to a specific functional group. An ethoxy functional group is an ethyl group
`
`singular bonded to oxygen (CH3CH2O—). The verb form of ethoxylate means to
`
`perform a chemical reaction whereby an ethoxy group is chemically added to a
`
`compound. A polyoxyethylene group would have repeat units of oxyethylene (—
`
`OC2H4—) and is formed in an ethoxylation reaction. Ex. 1005, ¶ 81. When in an
`
`ester form, the fatty acid oleic acid is described as an “oleate.” Ex. 1005, ¶ 81.
`
`Therefore, Polysorbate 80 (“TWEEN” 80) is “an ethoxylated sorbitan ester” as
`
`recited in Claim 1 in that the sorbitan is “ethoxylated” with at least one
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`
`
`
`“oxyethylene” group and is an “ester” in view of the designation of an “oleate”
`
`group. Ex. 1005, ¶¶ 81–82.
`
`
`
`The teachings of ICI show that there was more than a reasonable expectation
`
`of success at the time of the ’059 Patent in using Polysorbate 80 (also known as
`
`TWEEN 80) listed in Alther for increasing the water/oil separation of a byproduct
`
`stream (e.g., stillage or resulting syrup) in a centrifuge thereby solving the problem
`
`recognized by Winsness. One skilled in the art reading ICI would have recognized
`
`that polyoxyethylene sorbitan fatty acid esters sold under the tradename TWEEN
`
`would increase the water/corn oil separation of a material including water and corn
`
`oil such as the corn stillage or resulting syrup processed in Winsness. Ex. 1005, ¶¶
`
`68–72, 84–87. Table 2A of ICI notes that the required Hydrophile-Lipophile
`
`Balance (“HLB”) for selecting a surfactant to create the most stable oil-in-water
`
`emulsion based on corn oil is 10. Ex. 1008, p. 3, col. 1, ¶ 3, p. 6, Table 2A; Ex.
`
`1005, ¶¶ 68–72, 84–87. However, Figure 4 of ICI demonstrates that when the
`
`HLB number varies (up or down) from the recommended HLB number, the
`
`emulsion stability decreases significantly. Ex. 1008, p. 13, FIG. 4; Ex. 1005, ¶¶
`
`68–72, 84–87.
`
`
`
`ICI shows 100% Tween 80 having an HLB of 15.0. Ex. 1008, p. 12. This
`
`HLB value is well above the ICI’s recommended HLB of 10 for corn oil. Ex.
`
`1005, ¶¶ 68–72, 84–87. Thus, looking at Figure 4 of ICI and comparing the
`
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`

`
`
`
`recommended HLB for corn oil (10) and the HLB of TWEEN 80 (15.0), it would
`
`have been apparent that TWEEN 80 would significantly decrease the emulsion
`
`stability of corn oil and water. Ex. 1005, ¶¶ 68–72, 84–87. Stated differently, the
`
`high HLB of TWEEN 80 (Polysorbate 80) will demulsify an emulsion of corn oil
`
`and water thereby promoting the water/corn oil separation of corn stillage in a
`
`centrifuge as used in Winsness. Ex. 1005, ¶¶ 68–72, 84–87.
`
`
`
`One skilled in the art would have been motivated to combine the teachings
`
`of Winsness and Alther because both teach separating oil using a centrifuge, and
`
`one would have looked to Alther to solve the emulsion problem (identified in both
`
`Alther and Winsness) by mixing Polysorbate 80 into the byproduct stream to form
`
`a mixture for improved processing of the byproduct stream in the centrifuge. Ex.
`
`1005, ¶¶ 78–88. The teachings of ICI show that there was more than a reasonable
`
`expectation of success at the time of the ’059 Patent in using Polysorbate 80 as
`
`specifically listed in Alther in the Winsness process for increasing the water/oil
`
`separation of corn stillage. See In re O’Farrell, 853 F.2d 894, 903–04 (Fed. Cir.
`
`1988) (“[O]bviousness does not require absolute predictability of success. . . . For
`
`obviousness under § 103, all that is required is a reasonable expectation of
`
`success.”).
`
`Claim
`2. The method of
`claim 1, wherein
`the ethoxylated
`
`Specific Reference to Prior Art
`Martin teaches “oxyalkylated sorbitan fatty esters.
`Representative surfactants are those surfactants marketed by
`ICI Americas Inc., under the trademark ‘Tween’ label.