Ex Parte Rissio

Patent Trial and Appeal Board

Sep 20, 2016

12672385 (P.T.A.B. Sep. 20, 2016)

UNITED STA TES p A TENT AND TRADEMARK OFFICE
APPLICATION NO. FILING DATE
12/672,385 03/01/2011
22045 7590 09/22/2016
BROOKS KUSHMAN P,C
1000 TOWN CENTER
TWENTY-SECOND FLOOR
SOUTHFIELD, MI 48075
FIRST NAMED INVENTOR
John Rissio
UNITED STATES DEPARTMENT OF COMMERCE
United States Patent and Trademark Office
Address: COMMISSIONER FOR PATENTS
P.O. Box 1450
Alexandria, Virginia 22313-1450
www .uspto.gov
ATTORNEY DOCKET NO. CONFIRMATION NO.
SOAP0149PUSA 9080
EXAMINER
PO, MING CHEUNG
ART UNIT PAPER NUMBER
1771
NOTIFICATION DATE DELIVERY MODE
09/22/2016 ELECTRONIC
Please find below and/or attached an Office communication concerning this application or proceeding.
The time period for reply, if any, is set in the attached communication.
Notice of the Office communication was sent electronically on above-indicated "Notification Date" to the
following e-mail address( es):
docketing@brookskushman.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte JOHN RISSIO and JOHN CAMERON
Appeal2015-004135
Application 12/672,385
Technology Center 1700
Before CHUNG K. PAK, JEFFREY T. SMITH, and
WESLEY B. DERRICK, Administrative Patent Judges.
PAK, Administrative Patent Judge.
DECISION ON APPEAL
Appellants 1 appeal under 35 U.S.C. § 134(a) from the Examiner's
decision rejecting claims 1through28. We have jurisdiction under 35
U.S.C. § 6(b).
We AFFIRM.
The subject matter on appeal is generally directed to a method of
forming a bio-organic composition and to a bio-organic composition.
(Spec. 2, 11. 9-18.)
1 Appellants do not identify the Real Party in Interest. (See generally Appeal
Brief filed July 21, 2014 ("App. Br.").)
Appeal2015-004135
Application 12/672,385
Details of the appealed subject matter are recited in representative
claims 1 and 16, which are reproduced below from the Claims Appendix to
the Appeal Brief:
1. A method of forming a bio-organic composition, the
method comprising:
a) mixing a fatty acid glyceride-containing composition
and a first reaction promoter at a first predetermined
temperature to form a first intermediate reaction mixture;
b) adding a first epoxide or glycol to the first reaction
mixture to form a second intermediate reaction mixture;
c) combining at least a portion of the second intermediate
reaction mixture with a solvent and additional reaction
promoter to form a third intermediate reaction mixture;
d) adding a second epoxide to the third intermediate
reaction mixture to form a fourth intermediate reaction mixture;
and
e) removing the solvent such that the bio-organic
composition is recovered.
16. A bio-organic composition comprising:
residues of a fatty acid glyceride-containing composition,
the fatty acid glyceride-containing composition having a first
viscosity and a first pour point;
residues of a first epoxide present in a first epoxide
concentration or residues of a first glycol present in a first
glycol concentration; and
residues of a second epoxide present in a second epoxide
concentration, wherein the first epoxide is the same or different
than the second epoxide and wherein the first and second
concentrations are such that the bio-organic composition has a
viscosity lower that [sic] the first viscosity and/or a pour point
lower than the first pour point.
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Application 12/672,385
The Examiner entered a new ground of rejection in the Answer entered
on December 22, 2014 ("Ans.") of claims 1-28 under 35 U.S.C. § 103(a) as
unpatentable over the disclosures of U.S. Patent 4,364,743 issued in the
name of Erner on December 21, 1982 (hereinafter referred to as "Erner") in
view of U.S. Patent 6,310,233 Bl issued in the name of Maurer et al. on
October 30, 2001 (hereinafter referred to as "Maurer"). (Ans. 2---6.) The
Examiner also relied upon Holliday et al., "Hydrolysis of Vegetable Oils in
Sub- and Supercritical Water," Ind. Eng. Chem. Res., Vol. 36, No. 3, pp.
932-35 (1997), and Susanti et al., Supercritical Fluid Technology for Energy
and Environmental Applications, pp 113-15 (Vladimir Anikeev and
Maohong Fan, eds., 2014), to support the official notice that obtaining free
fatty acids from glycerides in vegetable oils by hydrolysis reaction (in the
presence of water at high temperature) was well known in the art at the time
of the invention. (Ans. 10-11.)
DISCUSSION
Upon consideration of the evidence on this appeal record and each of
Appellants' contentions, we determine that Appellants have not identified
reversible error in the Examiner's rejection of claims 1-28 under 35 U.S.C.
§ 103(a). Accordingly, we affirm this rejection for the reasons set forth in
the Answer. We add the discussion below primarily for emphasis and
completeness.
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Application 12/672,385
Claims 1-10, 15, 17-19, and 23-282
Appellants do not dispute the Examiner's finding that Erner discloses
a synthetic fuel comprising fatty acid esters that are prepared by epoxide
addition of free fatty acids derived from vegetable oils (fatty acid glyceride-
containing composition). (Compare Ans. 3 with App. Br. 3-8.) The
Examiner acknowledged that Erner does not explicitly disclose the process
of deriving the free fatty acids from vegetable oils, but took the official
notice and provided evidence that hydrolysis of vegetable oils to form free
fatty acids was a conventional process at the time of the invention, involving
conversion of water at high temperature into ions (first reaction promoter)
that catalyze the formation of free fatty acids from vegetable oils (fatty acid
glyceride-containing composition) (corresponding to step a) of claim 1 ).
(Ans. 3, 10-11.)
Appellants also do not dispute the Examiner's finding that Erner
discloses an epoxide addition reaction involving reacting the free fatty acids
2 We limit our discussion to those claims separately argued, and claims not
separately argued stand or fall with the argued claims. 37 C.F.R.
§ 41.37(c)(l)(iv). Appellants argue claims 1-10, 15, 17-19, and 23-28 as a
group on the basis of claim 1. (See generally App. Br. 3-8.) Therefore, for
the purposes of this appeal, we select claim 1 as representative, and decide
the propriety of the rejection of claims 1-10, 15, 17-19, and 23-28 based on
claim 1 alone.
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Application 12/672,385
derived from vegetable oils (first intermediate reaction mixture) with
alkylene oxides such as ethylene or propylene oxides (first epoxide) at
temperatures between 105QC and 120°C in the presence of a potassium
hydroxide catalyst (corresponding to step b) of claim 1 ). (Compare Ans. 3
with App. Br. 3-8.) Nor do Appellants dispute the Examiner's finding that
Erner discloses adding the epoxide continuously or further until the reaction
is complete, which according to the Examiner, corresponds to adding a
second epoxide as recited in step d) of claim 1. (Compare Ans. 4 with App.
Br. 3-8.)
The Examiner acknowledged that Erner does not disclose adding
solvent and an additional reaction promoter to the reaction (corresponding to
step c) of claim 1 ), and relied on Maurer for this feature missing from
Erner's disclosures. (Ans. 3--4.) Appellants do not dispute the Examiner's
finding that Maurer discloses a process for preparing hydroxyl alkyl esters
that involves reacting one or more dicarboxylic acids with one or more
alkylene oxides in the presence of a solvent, an optional co-solvent such as
water or methanol, and an optional catalyst (corresponding to step c) of
claim 1). (Compare Ans. 4 with App. Br. 3-8.) Nor do Appellants dispute
the Examiner's finding that Maurer discloses removing the solvents from the
reaction products subsequent to the epoxide addition reaction (corresponding
to step e) of claim 1 ). (Compare Ans. 4 with App. Br. 3-8.) Because both
Erner and Maurer disclose an epoxide addition reaction for producing
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Application 12/672,385
hydroxyl alkyl esters, the Examiner concluded that it would have been
obvious to one of ordinary skill in the art at the time of the invention to add
an optional solvent such as water and catalyst (reaction promoter) to the
epoxide addition reaction disclosed in Erner. (Ans. 4.)
Appellants argue that Erner fails to disclose a multistep process in
which epoxides are added to a reaction mixture before and after addition of a
solvent, as recited in claim 1. (App. Br. 4--5.) Appellants further argue that
Maurer fails to cure the deficiencies of Erner because Maurer, like Erner,
does not disclose or suggest a multistep process as recited in claim 1 in
which at least four intermediate mixtures are formed, and Maurer's reactions
conditions are incompatible with those of Erner. (App. Br. 6-8.)
Appellants also argue that Maurer is directed to the preparation of monomers
from dicarboxylic acids, which differ from fatty acid glycerides and free
fatty acids. (App. Br. 6.)
However, we agree with the Examiner that the combined disclosures
of Erner and Maurer would have suggested the process recited in claim 1 to
one of ordinary skill in the art at the time of the invention, for at least the
following reasons.
Erner discloses a method for preparing fatty acid esters that involves
epoxide addition of free fatty acids derived from vegetable oils such as
coconut oil, com oil, cottonseed oil, palm oil, and safflower oil, which,
according to Appellants, contains fatty acid glyceride. (Erner col. 5, 11. 51-
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Application 12/672,385
62; col. 6, 11. 28--40 and Spec. 4, 11. 15-20.) The Examiner provided
evidence demonstrating that hydrolysis of vegetable oils (fatty acid
glyceride-containing compositions) to form free fatty acids---corresponding
to step a) of claim I-was a conventional process at the time of the
invention in which ions formed from water (first reaction promoter) catalyze
the reaction. (Ans. 10-11 citing Holliday, et al., Hydrolysis of Vegetable
Oils in Sub- and Supercritical Water, 36 Ind. Eng. Chem. Res. 932 (1997),
and Susanti et al., Supercritical Fluid Technology for Energy and
Environmental Applications, pp 113-15 (Vladimir Anikeev and Maohong
Fan, eds., 2014).) Accordingly, we concur with the Examiner that one of
ordinary skill in the art reasonably would have used such a conventional
process to prepare the free fatty acids derived from vegetable oils disclosed
in Erner.
As also indicated supra, there is no dispute that that Erner' s disclosure
of an epoxide addition reaction in which free fatty acids derived from
vegetable oils are reacted with ethylene oxide or propylene oxide (first
epoxide) using potassium hydroxide as a catalyst (reaction promoter)
corresponds to step b) of claim 1, and Erner' s disclosure of continuous or
further addition of an epoxide to the reaction until it is complete corresponds
to adding a second epoxide as recited in step d) of claim 1. (Ans. 3; Erner
col. 6, 11. 28--40.) Although Erner does not mention adding a solvent and an
additional promoter during its epoxide addition reaction as required by step
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Application 12/672,385
c) of claim 1 or removing the solvent after its epoxide addition reaction as
required by step e) of claim 1, the Examiner correctly found that Maurer
discloses a process for preparing hydroxyl alkyl esters in its epoxide addition
reaction in the presence of an optional co-solvent such as water or methanol,
and an optional catalyst as recited in step c) of claim 1 and removing the
solvent after forming the hydroxyl alkyl esters as recited in step e) of
claim 1. In particular, Maurer, like Erner, discloses a process for producing
hydroxylalkyl esters. (Maurer col. 4, 11. 33-37; Erner col. 6, 11. 37-38.)
Maurer also discloses a process that involves ethoxylation of dicarboxylic
acids using alkylene oxide, which is an epoxide addition reaction like the
one described in Erner. (Maurer col. 3, 11. 35-38; Erner col. 6, 11. 35-36.)
As Appellants point out, Maurer' s reaction utilizes dicarboxylic acids as the
starting material, rather than free fatty acids as utilized by Erner, but both
dicarboxylic acids and free fatty acids possess the same acidic functional
groups. (App. Br. 6; Maurer col. 4, 11. 33-37; Erner col. 6, 11. 28-31.)
Maurer discloses that the ethoxylation reaction ( epoxide addition reaction) is
conducted at a temperature of 1 OOQC to 240QC, overlapping the temperature
used for Erner's epoxide addition reaction (105QC to 120QC). (Maurer col. 5,
11. 29-31; Erner col. 6, 11. 31-33.) Maurer further discloses conducting the
ethoxylation reaction in the presence of an optional catalyst and an optional
co-solvent, which can be water or methanol, and discloses removing the co-
solvent and catalyst after completion of the reaction. (Maurer col. 4, 11. 33-
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Application 12/672,385
38; col. 5, 11. 13-15; col. 6, 11. 11-22.) Therefore, contrary to Appellants'
arguments, Maurer' s reaction conditions are not incompatible with the
conditions used for Erner's reaction.
Because Mauerer discloses that an optional co-solvent such as water
or methanol can be used in an epoxide addition reaction to produce the same
product from starting materials having the same reactive functional group at
the same temperature as Erner's epoxide addition reaction, one of ordinary
skill in the art reasonably would have understood that Mauer' s optional co-
solvent could also be present during Erner's reaction contrary to Appellants'
argument. Furthermore, because Erner' s epoxide addition reaction involves
continuous addition of epoxide, one of ordinary skill in the art reasonably
also would have understood that the optional co-solvent could-like the
epoxy-be added during the course of the ongoing reaction. Thus, we
concur with the Examiner that the combined disclosures of Erner and
Maurer reasonably would have led one of ordinary skill at the time of the
invention to add the optional co-solvent disclosed in Maurer to the epoxide
addition reaction disclosed in Erner at any point during the reaction,
including at the beginning of the reaction, or during the course of the
reaction after an initial addition of epoxide, but before a further addition of
epoxide as recited in step c) of claim 1.
Appellants' arguments do not demonstrate that Maurer' s optional co-
solvent would not be useful in Erner's epoxide addition reaction involving
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Application 12/672,385
the same reaction chemistry as Mauer's ethoxylation reaction. Nor do
Appellants' arguments establish the criticality of the timing of the solvent
addition in the method of claim I. Cf In re Woodruff, 919 F.2d 1575, 1578
(Fed. Cir. 1990) (indicating that in cases in which the difference between the
claimed invention and the prior art is some range or other variable within the
claims, the applicant must show that the particular range is critical, generally
by showing that the claimed range achieves unexpected results relative to the
prior art range.). Appellants' arguments are therefore unpersuasive of
reversible error.
Appellants also argue that "Maurer is directed to preparing monomers
used in the polymerization to polyesters, and therefore, on its face
completely irrelevant to the present rejection." (App. Br. 6.) However, the
hydroxyalkyl esters produced by Erner' s epoxide addition reaction are
inclusive of the hydroxylalkyl ester monomers produced by Maurer' s
ethoxylation reaction. Both Mauer and Erner are directed to producing the
same products using the same reaction chemistry and thus one of ordinary
skill in the art interested in improving the process of Erner would look to
Mauer, and their combined disclosures would have suggested the process
recited in claim 1 as discussed above, regardless of whether the products of
Maurer's reaction are intended to be used in a further reaction. Appellants'
arguments are therefore unpersuasive of reversible error.
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Application 12/672,385
Appellants further argue that the Examiner impermissibly speculates
in asserting that water reacts with a fatty acid glyceride-containing
composition, such as vegetable oil, to form free carboxylic acids, or free
fatty acids. (App. Br. 6.) However, as discussed above, the Examiner took
an official notice and provided evidence in the Answer establishing that
hydrolysis of vegetable oils to form free fatty acids was a conventional
process at the time of the invention involving the conversion of water at high
temperature into ions that catalyze the conversion of vegetable oils into free
fatty acids. Appellants' arguments are therefore unpersuasive of reversible
error.
Appellants also argue that the evidence provided in Exhibits A---C of
the Appeal Brief establishes that the bio-organic composition produced by
the process of claim 1 exhibits superior performance over commercial bio-
diesel products, demonstrating "the unique nature of this sequence of steps"
recited in claim 1. (App. Br. 3--4.) However, Exhibits A---C do not describe
the method that was used to produce the bio-organic composition that was
tested and do not compare such bio-organic composition to the bio-organic
composition taught by Erner, the closest prior art. Accordingly, it is
impossible to determine whether the asserted superior bio-organic
composition was produced according to the method of claim 1 and has
unexpected properties relative to those produced by the closest prior art,
namely Erner. Thus, we determine that the evidence provided in Exhibits
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Application 12/672,385
A---C does not outweigh the evidence of obviousness proffered by the
Examiner.
Therefore, we sustain the Examiner's rejection of claims 1-10, 15,
17-19, and 23-28 under 35 U.S.C. § 103(a).
Claims 11 and 16
Appellants assert that claims 11 and 16 require the first epoxide to be
ethylene oxide and the second epoxide to be propylene oxide, and argue that
the Examiner does not identify any teaching in the applied prior art in which
two different epoxides are utilized. (App. Br. 8.)
However, claim 16 recites that "the first epoxide is the same or
different than the second epoxide," and Appellants' arguments regarding this
claim therefore lack merit.
With respect to claim 11, Erner discloses that the epoxide addition
reaction involves introduction of ethylene oxide or propylene oxide to a
mixture of free fatty acids. (Erner col. 6, 11. 31-33.) Erner thus indicates
that ethylene oxide and propylene oxide can be used interchangeably to
effect epoxide addition of free fatty acids. Accordingly, one of ordinary
skill in the art reasonably would have been led to use either ethylene oxide
or propylene oxide, or a combination of both ethylene oxide and propylene
oxide as recited in claim 11, in Erner's epoxide addition reaction, with a
reasonable expectation that using a combination of both epoxides would
result in a successful epoxide addition reaction to produce hydroxylalkyl
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Application 12/672,385
esters. KSR Int'! Co. v. Teleflex Inc., 550 U.S. 398, 417 (2007) (quoting
Sakraida v. Ag Pro, Inc., 425 U.S. 273, 282 (1976) ("[W]hen a patent
'simply arranges old elements with each performing the same function it had
been known to perform' and yields no more than one would expect from
such an arrangement, the combination is obvious."); In re Kerkhoven, 626
F .2d 846, 850 (CCP A 1980) ("It is prima facie obvious to combine two
compositions each of which is taught by the prior art to be useful for the
same purpose, in order to form a third composition which is to be used for
the very same purpose.") Appellants' arguments are therefore unpersuasive
of reversible error.
Therefore, we sustain the Examiner's rejection of claims 11 and 16
under 35 U.S.C. § 103(a).
Claims 12-15 and 20--233
Claim 12 recites a bio-organic composition prepared according to the
method of claim 1 that has a viscosity of less than or equal to about 30
centipoise at 25°C, while claim 14 also recites a bio-organic composition
prepared according to the method of claim 1, which has a pour point less
than or equal to about 0°F. The Examiner finds that the process for
3 Appellants argue claims 12-15 and 20-23 as a group. (App. Br. 8-9.)
Therefore, for the purposes of this appeal, we select claims 12 and 14 as
representative, and decide the propriety of the rejection of claims 12-15 and
20-23 based on claims 12 and 14 alone.
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Application 12/672,385
producing hydroxyalkyl esters disclosed in Erner as modified by Maurer is
substantially similar to the process recited in claim 1, and the Examiner
determines that one of ordinary skill in the art would have expected that the
products formed from both processes would have similar viscosities and
pour points, such as those recited in claims 12 and 14. (Ans. 5.)
Appellants argue that different epoxides can be used as the first and
second epoxides in the process of claim 1 for preparing a bio-organic
composition, and contend that the particular epoxides utilized in the process
affect the viscosity and pour point of the composition produced. (App. Br.
8-9.)
However, claim 1 is directed to using either the same epoxides or
different epoxides to produce bio-diesel fuel having the broadly recited
viscosity and pour point characteristics, inclusive of those recited in claims
12 and 14. Moreover, as discussed above, one of ordinary skill in the art
reasonably would have been led to use a combination of different epoxides,
such as ethylene oxide and propylene oxide, in Erner's epoxide addition
reaction to produce a bio-diesel fuel comprising hydroxylalkyl esters. In
other words, we agree with the Examiner that the process of Erner alone, or
as modified by Maurer, is identical or substantially identical to the method
of claim 1 and produces the same or substantially the same bio-diesel fuel
recited in claims 1, 12, and 14. (See also Erner col. 1, 11. 62---69.)
Accordingly, we concur with the Examiner that the collective teachings of
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Erner and Maurer would have suggested the process as recited in claim 1 to
produce a bio-diesel fuel, inclusive of those bio-diesel fuels having
particular viscosities and pour points recited in claims 1, 12, and 14. See
also Ex parte Obiaya, 227 USPQ 58, 60 (BPAI 1985) ("The fact that
appellant has recognized another advantage which would flow naturally
from following the suggestion of the prior art cannot be the basis for
patentability when the differences would otherwise be obvious."); In re
Kubin, 561F.3d1351, 1357 (Fed. Cir. 2009) ("Even if no prior art of record
explicitly discusses the [limitation], [applicants'] application itself instructs
that [the limitation] is not an additional requirement imposed by the claims
on the [claimed invention], but rather a property necessarily present in [the
claimed invention]"). On this record, Appellants do not show that such
broadly recited viscosities and pour points of such bio-diesel fuel would
further require unobvious steps or conditions in the process of claim 1 or
would not be present in the bio-diesel fuel produced in the process suggested
by Erner alone or Erner, as modified by Maurer. Accordingly, we sustain
the rejection of claims 12-14 and 20-22 under 35 U.S.C. § 103(a).
CONCLUSION
In view of the reasons set forth above, we affirm the Examiner's
rejection of claims 1 through 28 under§ 103(a).
No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136(a)(l )(iv).
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AFFIRMED
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