Syntroleum Corporationv.Neste Oil OYJ

Patent Trial and Appeal Board

Aug 29, 2014

13107146 (P.T.A.B. Aug. 29, 2014)

Trials@uspto.gov Paper 63
571-272-7822 Entered: August 29, 2014

UNITED STATES PATENT AND TRADEMARK OFFICE
_____________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
____________

REG SYNTHETIC FUELS, LLC,
1

Petitioner,

v.

NESTE OIL OYJ,
Patent Owner.
____________

Case IPR2013-00178
Patent 8,212,094 B2
____________

Before RAMA G. ELLURU, CHRISTOPHER L. CRUMBLEY, and
JON B. TORNQUIST, Administrative Patent Judges.

TORNQUIST, Administrative Patent Judge.

FINAL WRITTEN DECISION
35 U.S.C. § 318(a) and 37 C.F.R. § 42.73

1
On June 24, 2014, REG Synthetic Fuels, LLC (“REG”) filed updated
Mandatory Notices informing the Board that it had acquired—and is the
successor-in-interest to—Syntroleum Corporation, the originally-named
Petitioner in this proceeding. Paper 62. REG also filed a Power of Attorney
on that date, retaining the same counsel that filed the Petition on behalf of
Syntroleum. Paper 61.
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I. BACKGROUND
On March 8, 2013, Syntroleum Corp. (“Petitioner”) filed a Petition for inter
partes review of claims 1–20 of U.S. Patent No. 8,212,094 B2 (Ex. 1001, “the ’094
patent”). On March 21, 2013, Petitioner filed a corrected Petition. (Paper 7,
“Pet.”). On June 14, 2013, Nestle Oil Oyj (“Patent Owner”) filed a Preliminary
Response (Paper 11, “Prelim. Resp.”). In a Decision to Institute (Paper 22, “Dec.
on Inst.”) issued September 4, 2013, we instituted an inter partes review of claims
1–20 of the ’094 patent.
Patent Owner did not file a Patent Owner Response, and chose instead to file
a Motion to Amend (Paper 38, “Mot.”). Petitioner filed an Opposition to the
Motion to Amend (Paper 42, “Opp.”), and Patent Owner filed a Reply (Paper 46,
“PO Reply”). We held an oral hearing on April 1, 2014, and a transcript of the oral
hearing (Paper 60, “Tr.”) is included in the record.
Both Petitioner and Patent Owner presented declaration testimony in support
of their respective positions. With its Petition, Petitioner provided a declaration
from Edward L. Sughrue II, PhD. (Ex. 1002). With its Motion to Amend, Patent
Owner provided a declaration from Michael T. Klein, Sc.D. (Ex. 2019). With its
Opposition, Petitioner provided a second declaration from Dr. Sughrue (Ex. 1040),
and with its Reply, Patent Owner provided a second declaration from Dr. Klein
(Ex. 2041).
We have jurisdiction under 35 U.S.C. § 6(c). This final written decision,
issued pursuant to 35 U.S.C. § 318(a) and 37 C.F.R. § 42.73, addresses issues
raised during trial.
In its Motion to Amend, Patent Owner requests cancellation of claims 1–20
and substitution of those claims with proposed claims 21–30. For the reasons
discussed below, we determine that Patent Owner has not met its burden to prove
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by a preponderance of the evidence that the proposed substitute claims are
patentable. Accordingly, Patent Owner’s Motion to Amend is granted with respect
to the cancellation of claims 1–20 and denied with respect to the substitution of
claims 21–30.
A. The ’094 Patent
The ’094 patent relates to a process for the manufacture of diesel range
hydrocarbons from renewable sources, such as plant and animal oils or fats. Ex.
1001, 5:22–24. In the ’094 patent, a two-step process comprising a
hydrodeoxygenation, or HDO, step and an isomerization step is used to convert the
fatty acids and fatty acid derivatives in the fresh feed stream into branched n-
paraffin reaction products suitable for blending with diesel fuel. Id. at 5:22–39,
6:27–30, 10:8–20. In the HDO step, a stream of hydrogen and fresh feed is
introduced on catalyst beds. Id. at 6:17–24. As the hydrogen and fresh feed pass
over the catalyst beds, “oxygen from organic oxygen compounds” is removed as
water. Id. at 4:48–50. “[I]n the isomerization step, isomerization is carried out
which causes branching of the hydrocarbon chain and results in improved
performance of the product oil at low temperatures.” Id. at 10:9–13.
In the process of the ’094 patent, the HDO step is performed at a
“temperature between 200 and 400 °C, preferably between 250 and 350 °C, and
most preferably between 280 and 340 °C.” Id. at 9:4–8. Because the HDO step is
highly exothermic, a hydrocarbon diluting agent is introduced during the HDO step
to limit the temperature rise in the reactor. Id. at 1:66–2:8, 5:65–6:7. The diluting
agent may be a separate hydrocarbon or recycled product from the HDO step that
has been cooled using a heat exchanger. Id. at 6:42–48, 7:13–16. “[T]he ratio of
the dilution agent/fresh feed is 5-30:1, preferably 10-30:1, most preferably 12-
25:1.” Id. at 8:65–67.
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B. Instituted Challenges
In the Decision to Institute, we considered Petitioner’s and Patent Owner’s
arguments for and against the patentability of claims 1–20 and instituted inter
partes review of the ’094 patent on the following grounds:
1) Claims 1, 4, 7, and 9–20 as anticipated by Jakkula;2
2) Claims 1–7 and 9–20 as having been obvious over Jakkula;
3) Claim 8 as having been obvious over Jakkula and Monnier;3 and
4) Claims 5 and 6 as having been obvious over Jakkula and Harrison.4
Dec. on Inst. 24.
Patent Owner did not file a Patent Owner response addressing the
patentability of claims 1–20, nor did Patent Owner provide additional
reasoning or argument to support the patentability of these claims in the
Motion to Amend.
C. Illustrative Claims
In its Motion to Amend, Patent Owner proposes to add substitute
claims 21–30. Mot. 2. Substitute claims 21 and 30 are illustrative of the
proposed substitute claims and are reproduced below:
5

21. (Substitute for Original Claims 1, 3, 4, and 7) A process for the
manufacture of diesel range hydrocarbons comprising:
combining a fresh feed stream of biological origin containing more
than 5 wt-% of free fatty acids and a stream of diluting agent containing
hydrocarbons of biological origin to form a total feed stream,

2
EP Pub. App. 1396531 A2 (Ex. 1006) (“Jakkula”).
3
U.S. Patent No. 5,705,722 (Ex. 1031) (“Monnier”).
4 U.S. Patent No. 5,093,535 (Ex. 1014) (“Harrison”).
5
Subject matter deleted from original claim 1 is enclosed by brackets; subject
matter added to that claim is underlined.
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introducing the total feed stream to a hydrodeoxygenation step,
hydrodeoxygenating the total feed, in the hydrodeoxygenating step, at a
reaction temperature between 280-330 ºC to form a hydrodeoxygenated
product containing n-paraffins in the diesel range and less than 1 wt-% of
high molecular weight hydrocarbons,
introducing the hydrodeoxygenated product to an isomerization step,
and isomerizing the hydrodeoxygenated product in the isomerization step to
form isoparaffins in the diesel range,
wherein the total feed stream contains less than [10] 1 w-ppm alkali
and alkaline earth metals, calculated as elemental alkali and alkaline earth
metals, less than [10] 1 w-ppm other metals, calculated as elemental metals,
and less than [30] 5 w-ppm phosphorous, calculated as elemental
phosphorous.
30. (New) The process according to claim 21, wherein the
hydrodeoxygenating step is at a reaction temperature between 280-305 ºC.
Dependent claims 22–29 are proposed substitutes for original claims
5, 6, and 8–13 of the ’094 patent. Mot. 4–5. These proposed substitute
claims differ from the original claims only in that they recite dependency
from newly proposed claim 21, instead of original claim 1. Id.

II. DISCUSSION
A. Claim Construction
Neither party challenges the claim constructions provided in the
Decision to Institute. Accordingly, to the extent that they are necessary for
assessing Patent Owner’s Motion to Amend, those previous constructions
are adopted for purposes of this final decision. See Dec. on Inst. 8–13.
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With respect to the newly added limitations, Patent Owner submits
proposed constructions for the terms: reaction temperature, n-paraffins, high
molecular weight hydrocarbons, and isoparaffins. Mot. 7–8.
1. Isoparaffins and n-Paraffins
Patent Owner argues that isoparaffins “should be construed to mean
alkanes having one or more C1-C9, typically C1-C2 alkyl side chains,
typically mono-, di-, tri-, or tetramethylalkanes” and n-paraffins “should be
construed to mean normal alkanes or linear alkanes that do not contain side
chains.” Mot. 8. Petitioner does not dispute these proposed constructions.
As Patent Owner’s proposed constructions mirror the express definitions
provided in the patent, we construe the terms in a manner consistent with
Patent Owner’s proposals. See Ex. 1001, 5:12–16.
2. Reaction Temperature and High Molecular Weight Hydrocarbons
Patent Owner asserts that reaction temperature should be construed to
mean “the temperature at which a hydrodeoxygenation reaction occurs” and
high molecular weight hydrocarbons should be construed to mean
“hydrocarbons having a molecular weight double or more of the feed,”
which “are not in the boiling range of diesel fuel.” Mot. 8; Ex. 2019 ¶¶ 36,
38. In its Opposition, Petitioner asserts that reaction temperature should be
construed as the “temperature of the HDO reactor” and that the term high
molecular weight hydrocarbons is indefinite. Opp. 1.
At oral argument the parties conceded that their respective written
description and patentability arguments did not rely on the construction of
either term. Tr. 8:10–17, 11:12–20, 61:2–9, 62:19–63:3. As our decision in
this case, likewise, does not turn on a particular construction for these terms,
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we decline to provide an express construction for reaction temperature and
high molecular weight hydrocarbons.
B. The Motion to Amend
An inter partes review is more adjudicatory than examinational. See
generally Abbott Labs. v. Cordis Corp., 710 F.3d 1318, 1326 (Fed. Cir.
2013). Unlike examination, entry of the proposed substitute claims in an
inter partes review is not automatic. Patent Owner must establish that it is
entitled to the requested relief. See 37 C.F.R. § 42.20(c).
In its Motion to Amend, Patent Owner bears the burden to show, inter
alia, that a reasonable number of substitute claims are proposed, that these
claims are adequately supported by the written description of the application
as originally filed, and that the proposed claims are patentable over the prior
art. See 37 C.F.R. § 42.121; Idle Free Sys. Inc. v. Bergstrom, Inc., Case
IPR2012-00027, slip op. at 5–6 (PTAB June 11, 2013) (Paper 26). We
address each of these requirements in turn.
1. Reasonable Number of Substitute Claims
A patent owner may propose a reasonable number of substitute claims
for each challenged claim. 35 U.S.C. § 316(d)(1). Absent special
circumstances, it is presumed that only one substitute claim is needed to
replace each challenged claim. 37 C.F.R. § 42.121(a)(3). This presumption
may be rebutted by showing that the substitute claims are patentably distinct
from each other. Idle Free, Paper 26, 8–9. To the extent that no patentable
distinction is shown, we may deny entry of the excess claims or group them
together for purposes of considering patentability over prior art. See id.
In its Motion to Amend, Patent Owner proposes to add claim 21 as a
substitute for original claims 1, 3, 4, and 7. Mot. 3. Patent Owner also
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proposes to add “new” substitute claim 30, which depends from claim 21
and is directed to HDO temperatures in the range of 280–305 °C. Mot. 5, 7.
Claim 30 is not identified as a substitute for any original claim and, as it
depends from claim 21, contains all of the limitations of that claim.
Accordingly, claims 21 and 30 are both considered substitutes for original
claims 1, 3, 4, and 7. See Idle Free, Paper 26, 8. As more than one
substitute claim is proposed for a single original claim, for example, both
claim 21 and claim 30 substitute for claim 1, Patent Owner must establish a
need for new claim 30. Id.
Patent Owner argues that claim 30 is needed because its temperature
range of 280–305 °C is “narrower and distinct from the 280–330 °C range of
proposed substitute claim 21,” further distinguishing the claim from the prior
art. Mot. 17; Tr. 66:1–15. Although we agree that the temperature range of
280–305 °C is narrower than 280–330 °C, Patent Owner has not established
that this narrower range renders claim 30 patentably distinct from claim 21.
Mot. 17; Ex. 2019 ¶ 78; Ex. 2041 ¶ 59. We, therefore, are not persuaded
that Patent Owner has satisfied its burden to show a need for substitute claim
30. Instead of denying entry of claim 30, however, we exercise our
discretion to group claim 30 with claim 21 for purposes of considering
patentability of the claims over prior art. See Idle Free, Paper 26, 8–9.
2. Written Description Support
Patent Owner bears the burden to show written description support in
the original disclosure for each proposed substitute claim. 37 C.F.R.
§ 42.121(b)(1); 37 C.F.R. § 42.20(c). The test for written description
support is “whether the disclosure of the application relied upon reasonably
conveys to those skilled in the art that the inventor had possession of the
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claimed subject matter as of the filing date.” Ariad Pharm., Inc. v. Eli Lilly
& Co., 598 F.3d 1336, 1351 (Fed. Cir. 2010).
Substitute claim 21 recites obtaining an HDO product having “less
than 1 wt-% of high molecular weight hydrocarbons” using “a stream of
diluting agent.” Proposed substitute claims 22 and 23, which depend from
claim 21, further require the diluting agent be in a ratio of 5–30:1 and 10–
30:1, respectively. Thus, claim 21 presumptively encompasses the use of
dilution ratios outside a 5–30:1 ratio. See Liebel-Flarsheim Co. v. Medrad,
Inc., 358 F.3d 898, 910 (Fed. Cir. 2004) (“[T]he presence of a dependent
claim that adds a particular limitation raises a presumption that the limitation
in question is not found in the independent claim.”)
Patent Owner argues that obtaining “less than 1 wt-% high molecular
weight hydrocarbons” using an unbounded dilution ratio is supported by the
reported experimental results and the disclosure that product recycle dilution
can prevent or remarkably decrease the reactions between free fatty acids
and the formation of high molecular weight compounds during
hydrotreating. See Mot. 6–7; PO Reply 3; Ex. 2017 ¶ 64.
We are not persuaded by this argument. The reported “surprising[]”
experimental results, including the ability to “prevent or remarkably
decrease” the formation of high molecular weight hydrocarbons, are directly
tied to a dilution ratio of “at least 5:1”:
It was surprisingly observed in examples that product recycle
dilution can prevent or remarkably decrease the reactions
between free fatty acids and the formation of high molecular
weight compounds during hydrotreating, when at least 5:1
(product recycle):(fresh oil)-ratio was used.
. . .
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In the examples it was be (sic) seen that the ratio of at least 5:1
(recycle:fresh) significantly decreased the formation of high
molecular weight products, when the feedstock contains 10 wt-
% of free fatty acids (calculated from fresh oil) is used. Using
at least 5:1 recycle ratio and reduced reaction temperature, free
fatty acids can be processed without the need for
deacidification. High quality hydrocarbons are obtained,
suitable for the diesel fuel pool with high yield.

Ex. 2017 ¶¶ 64, 73 (emphases added). Moreover, throughout the ’094 patent
specification, the dilution ratio is described as “5-30:1, preferably 10-30:1,
most preferably 12-25:1.” Id. ¶¶ 38, 43, 56, 62.
In its reply, Patent Owner points to several paragraphs of the ’094
patent disclosure that describe the invention without mentioning a 5-30:1
dilution ratio, and argues that “[t]he examples, which use a 5:1 ratio of
product recycle/fresh feed, do not diminish” these “broader statements nor
suggest that this is the only ratio possible.” PO Reply 2; Mot. 7; Ex. 2017
¶¶ 2, 23, 24, 37, 64, 72, 73, 84; Ex. 2041 ¶ 19. We are not persuaded by this
argument. First, several of the identified disclosures indicate that the
dilution level is “high,” not unbounded.
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Ex. 2017 ¶¶ 2, 72. Second, even if
other dilution ratios are “possible,” the general descriptions identified by
Patent Owner do not establish that these alternate dilution ratios would
achieve a product having “less than 1 wt-% of high molecular weight
hydrocarbons.” See Ex. 2041 ¶ 19; Opp. 5. For example, paragraphs 2, 23,
24, 37, and 72 of the ’094 patent specification merely suggest that the level
of high molecular weight compounds may be “reduced” or “decreased,” and

6
At his deposition, Dr. Klein testified that a “high product recycle/fresh oil ratio”
encompasses any dilution ratio. Ex. 1088, 63:22–64:19; Paper 46, 5 (Patent
Owner’s Reply to Petitioner’s Motion for Observations). This reading, however,
would render the term “high” in the ’094 patent specification superfluous.
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not that the specific level of “less than 1 wt-%” may be achieved. See Ex.
2017 ¶¶ 2, 23, 24, 37, 72. And paragraphs 64, 73, and 84 of the ’094 patent
specification do not support Patent Owner’s argument as they are each
directly tied to the use of at least a 5:1 dilution ratio. Id. ¶¶ 64, 73, 84.
Patent Owner also asserts that an unbounded dilution ratio is
adequately supported because the “same language appeared in original
application claim 1.” PO Reply 2. We agree that original application claim
1 discloses using a “stream of diluting agent,” as does proposed claim 21.
Original claim 1 does not recite, however, the quality of the resulting
product, much less a product having “less than 1 wt-% high molecular
weight hydrocarbons.” Ex. 2017, 28 (claim 1). We, therefore, are not
persuaded that original claim 1 provides sufficient written description
support for proposed claim 21. See Lizardtech, Inc. v. Earth Resource
Mapping, Inc., 424 F.3d 1336, 1346 (Fed. Cir. 2005) (noting that, in order to
provide adequate written description support for later claims, the original
claim must actually support the limitation at issue).
Based on the foregoing, we are not persuaded that Patent Owner has
met its burden to show adequate written description support for obtaining a
product having “less than 1 wt-% high molecular weight hydrocarbons”
using an unbounded dilution ratio, as recited in proposed substitute claim 21
and proposed dependent claims 24–30.
3. Patentability over the Prior Art
In the Motion to Amend, Patent Owner combines in substitute claim
21 the limitations from claims 1, 3, 4, and 7, and argues that these
limitations now “distinguish the claims over the prior art.” Mot. 17–18.
Patent Owner does not address, however, why these claim limitations, either
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in isolation or as combined in substitute claim 21, would render the claim
non-obvious. See Mot. 18. Nor does Patent Owner meaningfully discuss the
knowledge, skill, and creativity of one of ordinary skill in the art with
respect to these limitations. Id. Accordingly, we are not persuaded that
Patent Owner has carried its burden to show that the limitations contained in
original claims 1, 3, 4, and 7, either alone or in combination, patentably
distinguish claim 21 from the prior art.
We focus, therefore, as have both of the parties, on whether the two
newly added limitations—an HDO reaction temperature of 280-330 °C and a
hydrodeoxygenated product containing “less than 1 wt-% of high molecular
weight hydrocarbons”—render claim 21 patentable over the prior art. See
Mot. 3, 10–17.
a. Prior Art (Jakkula)
Jakkula relates to a process for producing hydrocarbons from
biological raw materials that are suitable as diesel fuel. Ex. 1038 ¶¶ 1, 12.
Like the ’094 patent, Jakkula utilizes a two-step process comprising a HDO
step and an isomerization step. In the HDO step, “the structure of the
biological component is decomposed, oxygen, nitrogen, phosphorus and
sulfur compounds, and light hydrocarbons as gas are removed, and the
olefinic bonds are hydrogenated.” Id. ¶ 16. In the isomerization step, the
product of the HDO step is passed over an isomerization catalyst to initiate
branching of the hydrocarbon chains, thereby improving the performance of
the product at low temperatures. Id.
In Jakkula, the HDO step is performed at temperatures between 200
and 500 °C, and preferably in the range of 300–400 °C. Id. ¶ 20. To control
the “exothermal character of the reactions” in the HDO step, Jakkula
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discloses that the hydrocarbon reaction products may be recycled back to the
reaction chamber as a diluent. Id. ¶¶ 19, 24, 61.
In Jakkula, “it was surprisingly found that the problems of the prior
art processes may be avoided or at least substantially reduced by the process
of the invention having at least two steps.” Id. ¶ 16. For example, Jakkula
reports that it was surprisingly found “that the use of a biological feed stock
in the processes is possible” and that “the composition of the feed may vary
considerably without affecting the quality of the end product.” Id. ¶ 65.
Jakkula further reports that the properties of the resulting product are
“excellent” and “very suitable as a component in diesel fuels without any
blending restrictions.” Id. ¶ 73. Jakkula reports no issues with the formation
of high molecular weight hydrocarbons or with plugging within the system.
See id. ¶¶ 70–73.
b. 280-330 °C
The proposed 280-330 °C temperature range of claim 21 is fully
encompassed by Jakkula’s disclosed 200-500 °C range, and partially
overlaps the preferred temperature range of 300-400 °C. When a claimed
range is encompassed by, or overlaps with, a prior art range, the claimed
range is presumed to be obvious. See In re Peterson, 315 F.3d 1325, 1329
(Fed. Cir. 2003). “This presumption can be rebutted if it can be shown that
the prior art teaches away from the claimed range, or the claimed range
produces new and unexpected results.” Ormco Corp. v. Align Tech., Inc.,
463 F.3d 1299, 1311 (Fed. Cir. 2006).
Patent Owner argues that the presumption of obviousness is rebutted
in this case because a prior art patent to Craig et. al. (U.S. Patent No.
4,992,605, Ex. 1013, “Craig”) allegedly teaches away from the use of HDO
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temperatures below 350 °C. Mot. 11. Craig, which issued in 1995,
discloses a series of bench top HDO experiments using various feedstocks.
Ex. 1013, 4:3–10, Table 8. Craig reports that at HDO reaction temperatures
below 350 °C “the product collection system was plugged with a solid
margarine-like material,” and concludes that “350 °C was the lower limit for
trouble-free operation.” Ex. 1013, 7:11–13, 9:39–10:16; Ex. 2041 ¶¶ 29–30.
Patent Owner asserts that, because Craig, unlike Jakkula, conducted a series
of experiments to identify the working temperatures for the HDO step, and
because Craig allegedly conducted these experiments using similar
feedstocks, pressures, and catalysts as Jakkula, one of ordinary skill in the
art would have given Craig’s teachings more weight and would have
avoided HDO temperatures below 350 °C. Mot. 11–14; PO Reply 3–4; Ex.
2041 ¶¶ 29–32, 35, 41.
“A reference may be said to teach away when a person of ordinary
skill in the art, upon reading a reference, would be discouraged from
following the path set out in the reference, or would be led in a direction
divergent from the path that was taken by the applicant.” In re Gurley, 27
F.3d 551, 553 (Fed. Cir. 1994). “[I]n weighing the suggestive power of each
reference, [the Board] must consider the degree to which one reference
might accurately discredit another.” In re Young, 927 F.2d 588, 591 (Fed.
Cir. 1991). When two references do not use directly comparable techniques
or operating conditions, the impact of an allegedly discrediting reference
may be significantly reduced. See id. at 592.
Dr. Sughrue testifies that one of ordinary skill in the art would have
understood that the “different reactor configurations and catalysts” used in Jakkula
“could and would lead to differing optimal temperatures from those reported in
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Craig.” Ex. 1040 ¶ 36 (emphasis added). For example, Dr. Sughrue testifies that
one of ordinary skill in the art would have understood that reduced temperatures,
as well as dilution—which was used in Jakkula but was not studied as an operating
variable in Craig—could “greatly reduce the rate of dimerization and
oligomerization of free fatty acids” and would lead to lower levels of high
molecular weight hydrocarbons. Ex. 1040 ¶¶ 42, 60, 90; Ex. 1013, 4:11–13. Dr.
Sughrue also provides evidence that in the years after the publication of Craig “the
activity of hydroprocessing catalysts increased dramatically,” permitting lower
reaction temperatures in the HDO step. Id. ¶¶ 31, 33. In light of these differences,
Dr. Sughrue concludes that one of ordinary skill in the art “would not have been
dissuaded from considering HDO reaction temperatures at or near the low end of
the preferred temperature range taught in [Jakkula], e.g., 300 °C, or even lower
temperatures within the more broadly taught range of 200-500 °C.” Ex. 1040 ¶ 37.
We find Dr. Sughrue’s testimony persuasive. In particular, in light of
Jakkula’s disclosed successful results, we are persuaded that one of ordinary skill
in the art would not have viewed Craig’s 350 °C minimum temperature for
“trouble-free operation” as a line not to be crossed, but would have understood that
the optimal and minimum temperatures for the HDO step would vary depending on
the particular reactor configuration and operating conditions used. See In re
Boesch, 617 F.2d 272, 276 (CCPA 1980) (“Discovery of an optimum value of a
results effective variable in a known process is ordinarily within the skill in the
art.”). Although Dr. Klein presents an opposing view from that of Dr. Sughrue,
upon review of both expert declarations and their corresponding depositions, on
balance, we find that Dr. Sughrue’s testimony more persuasively considers not
only the express teachings of Craig and Jakkula, but also the timing of the two
disclosures, the differences in reactor configuration and operating conditions, and
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the knowledge, skill, and reasoning ability of one of ordinary skill in the art.
Syntex (U.S.A.) LLC v. Apotex, Inc., 407 F.3d 1371, 1380 (Fed. Cir. 2005) (“What
a reference teaches or suggests must be examined in the context of the knowledge,
skill, and reasoning ability of a skilled artisan.”)
We, therefore, are not persuaded that Patent Owner has carried its burden to
show that Craig sufficiently teaches away from, or discredits, the lower end of
Jakkula’s preferred temperature range to rebut the presumption of obviousness.
c. Less Than 1 wt-% of High Molecular Weight Hydrocarbons
Patent Owner asserts that it would not have been obvious to obtain an
HDO product having “less than 1 wt-% of high molecular weight
hydrocarbons.” Mot. 15. According to Patent Owner, because one of
ordinary skill in the art would not have appreciated “the problem of high
molecular weight hydrocarbon formation when hydrodeoxygenating
feedstocks containing free fatty acids, no reason existed at the time of the
’094 invention to optimize the prior art HDO processes to minimize the
negative effects” of such compounds. Id. In support of this argument, Dr.
Klein testifies that “[t]o my knowledge no publication before the ’094 patent
identified that the presence of free fatty acids in a biological feedstock was a
recognized source of problems in hydrodeoxygenation.” Ex. 2019 ¶ 11; Ex.
2041 ¶ 60.
In its Opposition, Petitioner argues that Patent Owner and Dr. Klein
“are flat wrong when they claim that no one before the ’094 patent
recognized that the processing of streams containing [free fatty acids] could
promote the formation of [high molecular weight hydrocarbons]” as the
propensity for free fatty acids to form high molecular weight compounds has
been “well-known and well-studied in the art for decades,” and was
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expressly acknowledged during prosecution of the ’094 patent. Opp. 11–12;
Ex. 1040 ¶¶ 39–41.
We find Petitioner’s argument persuasive. In particular, during
prosecution of the parent application to the ’094 patent, the patentee
repeatedly asserted that one of ordinary skill in the art would understand that
operating an HDO process on biologic feedstocks with high levels of free
fatty acids would result in the formation of high molecular weight
hydrocarbons. For example, it was argued in a March 17, 2008, Amendment
in response to an Office Action that it was known in the art that free fatty
acids contributed to the formation of high molecular weight compounds:
As is known in the art, several problems arise during processing
of bio-oils and fats, including general deoxygenation activity,
potential side reactions, catalyst deactivation due to free fatty
acids and high hydrogen consumption in the hydrotreatment
step. Side reactions in the hydrotreatment step, resulting in the
formation of heavy molecular weight compounds, are
significantly increased, due to the presence of free fatty acids
and/or their derivatives in the feed.

Ex. 1052, 9 (emphasis added). Likewise, in a declaration submitted
by Jukka Myllyoja—a common inventor on both the ’094 patent and
Jakkula—it was asserted that “[a] man skilled in the art would expect
to encounter problems when a feed containing high amounts of free
fatty acids is hydroprocessed on an industrial scale,” including “[t]he
formation of high molecular weight compounds.” Ex. 1048, 3.
In light of the assertions made during prosecution, we are not
persuaded that the propensity for free fatty acids to promote the
formation of high molecular weight hydrocarbons was unknown prior
to the ’094 patent. See also Ex. 1040 ¶¶ 38–61 (asserting that the
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dimerization of unsaturated free fatty acids was well-known in the art
from as early as 1984 and was disclosed in Jakkula (Ex. 1038 ¶ 21)).
Patent Owner further argues that “each part of the claimed process—
the low HDO reaction temperature, the dilution, and the low metallic and
phosphorus contaminant levels—is needed to achieve” less than 1 wt-% high
molecular weight hydrocarbons using feedstock with more than 5 wt-% free
fatty acids. Mot. 15. According to Patent Owner, because the synergy of
these reaction parameters was not known prior to the ’094 patent, one of
skill would not have been able to optimize the Jakkula process to achieve the
claimed results. Id.; Ex. 2019 ¶ 79; Tr. 31:22–32:6.
Patent Owner identifies Example 5 as alleged support for its argument
that all three elements (temperature, dilution, and low levels of impurities)
are required to achieve “less than 1 wt-% high molecular weight
hydrocarbons.” Mot. 15. Patent Owner does not establish sufficiently,
however, that the combination of purified rapeseed oil and stearic acid used
in Example 5 was within the purity limitations of proposed substitute claim
21. Ex. 1088, 76:13–24; Ex. 1040 ¶ 73; Ex. 2019 ¶¶ 22, 34, 84. Moreover,
Dr. Sughrue testifies that in Figure 5, which represents an experiment run
with a feedstock containing high levels of impurities, the level of high
molecular weight hydrocarbons was kept below 1 wt-% for at least 8 days.
See Ex. 1040 ¶ 90. We agree with Dr. Sughrue that “Figure 5 thus illustrates
that the combination of a low HDO temperature, dilution, and feeds having
low impurities is not necessary to achieve the allegedly surprising result.”
Id. Accordingly, we are not persuaded that Patent Owner has established
that each of the claimed limitations is necessary to achieve an HDO product
containing “less than 1 wt-% high molecular weight hydrocarbons,” or that
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one of ordinary skill in the art could not optimize reaction conditions to
minimize the level of “high molecular weight hydrocarbons” without the
disclosure of the ’094 patent.
Based on the foregoing, Patent Owner has not met its burden to
demonstrate that claim 21 is patentable. As claim 30 is grouped with claim
21 for purposes of analyzing the patentability of the claims over the prior art,
we are also not persuaded that claim 30 is patentable. Moreover, even if we
were to address claim 30 individually, Patent Owner has not demonstrated
that this claim is patentable, as Patent Owner relies upon essentially the
same teaching away argument for claim 30 that we rejected for claim 21.
d. Proposed Substitute Claims 22–30
Patent Owner also argues that it would not have been obvious from
the combined teachings of Jakkula and Harrison to obtain the dilution ratios
of substitute claims 22 and 23:
Although Harrison uses dilution to control the temperature of
hydrogenation reactions (Ex. 1014 at 10:66-11:2), it provides
no reason to adjust the dilution ratio in combination with a low
reaction temperature and low metallic and phosphorus
contaminant levels to achieve less than 1 wt-% high molecular
weight hydrocarbons in an HDO reaction, as claimed.
Mot. 16.
Patent Owner’s argument, however, is limited to the grounds of
unpatentability asserted by Petitioner, and does not address the “prior art
known to the patent owner.” See Idle Free, Paper 26, 7. Patent Owner also
does not address the patentability of claims 22 and 23 with respect to the
knowledge and skill of an ordinary artisan. As noted above, the propensity
for free fatty acids to form high molecular weight hydrocarbons was known.
Dr. Sughrue testifies that, because these reactions are generally second
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order, one of ordinary skill in the art would have understood that dilution
should significantly reduce the formation of these high molecular weight
hydrocarbons. Ex. 1040 ¶¶ 41–42, 51, 88; Opp. 12. Dr. Sughrue further
testifies that one of ordinary skill in the art would be able to determine the
optimal dilution ratio while working within the dilution ratios set forth in the
prior art. Ex. 1040 ¶¶ 39–42, 90, 93; Ex. 1014, 14:22–39 (disclosing
dilution ratios between 1:3 to 1:99); Ex. 1008, 2 (disclosing dilution ratios
between 5:1 to 200:1). In light of this testimony, and Patent Owner’s failure
to specifically address the knowledge and skill of an ordinary artisan in the
Motion to Amend, we are not persuaded that Patent Owner has established
that claims 22 and 23 are patentable.
Patent Owner does not individually address the patentability of claims
24–29, relying instead on its arguments with respect to substitute claim 21.
As Patent Owner has not carried it burden to show that claim 21 is
patentable, we are not persuaded that Patent Owner has carried its burden to
show that claims 24–29 are patentable.
For all the foregoing reasons,
7
Patent Owner has not, in its Motion to
Amend, demonstrated the patentability of proposed substitute claims 21–30
to the ’094 patent.

III. CONCLUSION
Patent Owner has not demonstrated by a preponderance of the
evidence that proposed substitute claims 21–30 are patentable. Therefore,

7
Petitioner also argues that claims 21-30 are indefinite. Opp. 2-3. In light of our
determination that Petitioner has not shown by a preponderance of the evidence
that claims 21-30 satisfy the written description and other requirements for
patentability, we decline to address Petitioner’s indefiniteness argument.
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we deny the Motion to Amend with respect to the substitution of claims 21–
30. We grant the Motion to Amend solely with respect to Patent Owner’s
non-contingent request to cancel claims 1–20.

IV. ORDER
In consideration of the foregoing, it is
ORDERED that Patent Owner’s Motion to Amend is granted with
respect to the cancelation of claims 1–20;
FURTHER ORDERED that Patent Owner’s Motion to Amend is
otherwise denied; and
FURTHER ORDERED that because this is a final decision, parties to
the proceeding seeking judicial review of the decision must comply with the
notice and service requirements of 37 C.F.R. § 90.2.

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Petitioner:
Joseph Meara
jmeara@foley.com

Jeanne Gills
jgills@foley.com

Michael Houston
mhouston@foley.com

Patent Owner:

Michael Flibbert
michael.flibbert@finnegan.com

Anthony Hartmann
hartmana@finnegan.com

Maureen Queler
maureen.queler@finnegan.com