Ex Parte Krafft et al

Patent Trial and Appeal Board

Jan 13, 2017

12502342 (P.T.A.B. Jan. 13, 2017)

United States Patent and Trademark Office
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
APPLICATION NO. FILING DATE FIRST NAMED INVENTOR ATTORNEY DOCKET NO. CONFIRMATION NO.
12/502,342 07/14/2009 Philippe KRAFFT 345445US0DIV 6056
22850 7590 01/18/2017
OBLON, MCCLELLAND, MAIER & NEUSTADT, L.L.P.
1940 DUKE STREET
ALEXANDRIA, VA 22314
EXAMINER
KEYS, ROSALYND ANN
ART UNIT PAPER NUMBER
1671
NOTIFICATION DATE DELIVERY MODE
01/18/2017 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):
patentdocket @ oblon. com
oblonpat @ oblon. com
ahudgens@oblon.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte PHILIPPE KRAFFT, PATRICK GILBEAU,
BENOIT GOSSELIN, and SARA CLAESSENS1
Appeal 2014-008426
Application 12/502,342
Technology Center 1600
Before ULRIKE W. JENKS, KIMBERLY McGRAW, and
KRISTI L. R. SAWERT, Administrative Patent Judges.
JENKS, Administrative Patent Judge.
DECISION ON APPEAL
This is an appeal under 35 U.S.C. § 134(a) involving claims directed
to a method of producing dichloropropanol. The Examiner rejects the
claims as obvious. We have jurisdiction under 35 U.S.C. § 6(b).
We AFFIRM.
1 According to Appellants, the Real Party in Interest is SOLVAY (SOCIETE
ANONYME). (App. Br. 1.)
Appeal 2014-008426
Application 12/502,342
STATEMENT OF THE CASE
Claims 1 and 8—20 are on appeal and can be found in the Claims
Appendix of the Appeal Brief. Claim 1 is representative of the claims on
appeal, and reads as follows:
1. A process for producing dichloropropanol, wherein
glycerol is reacted with at least one chlorinating agent in a
reactor made of or coated with enameled steel,
the chlorinating agent comprises substantially anhydrous
hydrogen chloride or is an aqueous solution of hydrogen chloride
with a hydrogen chloride content higher than or equal to 4 % by
weight, and
a carboxylic acid, a carboxylic acid anhydride, a
carboxylic acid chloride, a carboxylic acid salt or a carboxylic
acid ester is present in the reaction as a catalyst.
(App. Br. Claims Appendix)
Appellants seek review of the Examiner’s rejection of claims 1 and 8—
20 under 35 U.S.C. § 103(a) as unpatentable over Britton2 in view of Steen3
and Smidt,4 and further in view of C. F. Boehringer,5 Griesheim-Elektron,6
Solvay,7 Jakobson,8 and Wang.9
The issue is: Does the preponderance of evidence of record support
the Examiner’s conclusion that the combination of references renders
2 Britton et al., US 2,144,612, issued Sept. 10, 1936 (“Britton”).
3 Van den Steen et al., US 3,406,007, issued Oct. 15, 1968 (“Steen”).
4 Smidt et al., US 3,131,226, issued Apr. 24, 1964 (“Smidt”).
5 Boehringer et al., DE197308, published Apr. 16, 1908 (“Boehringer”).
6 Griesheim-Elektron, DE238341, published Sep. 19, 1911 (“Griesheim-
Elektron”).
7 Solvay & Cie, GB 799,567, published Apr. 30, 1956 (“Solvay”).
8 Jakobson & Siemanowski, US 4,960,953 issued Oct. 2, 1990 (“Jakobson”).
9 Wang et al. US 4,499,255, issued Feb. 12, 1985 (“Wang”).
2
Appeal 2014-008426
Application 12/502,342
obvious the use of “a reactor made of or coated with enameled steel” in the
production of dichloropropanol as claimed?
Findings of Fact
We adopt the Examiner’s findings of fact and reasoning regarding the
scope and content of the prior art as set out in the Answer mailed July 17,
2014 and Final Action mailed Jan. 14, 2014. For emphasis only we
highlight the following:
FF1. Britton teaches that it was known to
react glycerol with hydrogen chloride in the presence of a
suitable catalyst such as acetic acid to form glycerol
dichlorohydrin and two molecules of water, the known
processes either allow the water of reaction to accumulate,
favoring equilibrium conditions long before complete
reaction can be obtained, or drive the water out of the
reaction mixture by conducting the reaction at elevated
temperatures, i. e., approximately 120° C. or higher.
(Britton col. 1,11. 4—13.)
FF2. Glycerol dichlorohydrin is also known as dichloropropanol (see Final
Act. 5).
FF3. Britton teaches including “an inert, water immiscible organic solvent
in which the dichlorohydrin product is soluble” in the organic solvent
mixture. (Britton col. 1,11. 30—35.)
FF4. Britton teaches that “[i]n carrying out the reaction, glycerol and the
solvent are mixed together in a suitable reaction vessel, together with
a catalyst such as formic or acetic acid, and hydrogen chloride reacted
therewith at temperatures varying with the particular solvent
employed, to produce glycerol dichlorohydrin and water.” (Britton
col. 1,11. 48-54.)
3
Appeal 2014-008426
Application 12/502,342
FF5. Britton teaches continuous distillation of the reaction mixture.
This distillate, hence forth termed the “acid fraction”, on
standing forms two layers, one comprising the organic
solvent and the other the aqueous hydrochloric acid. The
organic solvent layer may be separated therefrom in any
convenient manner and returned to the reaction zone, and
serves as an extractant to, remove the greater portion of
the dichlorohydrin product from the aqueous hydrochloric
acid solution, which tends to dissolve the same.
(Britton col. 2,11. 15—24.)
FF6. The Examiner finds that Britton “do[es] not disclose any details of the
vessel used to carry out their reaction.” (Final Act. 6.)
FF7. Steen discloses a process for producing molybdenum trioxide in a
reactor vessel using a hydrochloric gas reaction. The process
“comprises the steps of contacting a solid bed of material containing
molybdenum in an hexavalent oxidized form with a recycling gaseous
stream consisting essentially of hydrogen chloride at a temperature
between about 150° C. and 500° C.” (Steen col. 9,11. 1—5.)
FF8. Steen discloses that many different types of reactors can be employed
to carry out the reaction (see Steen col. 4,11. 2—14).
The reactor can be made of any materials resistant to
gaseous hydrochloric acid and oxidation at the above
stated temperatures; for example, nickel and nickel alloys,
special steels, or various ceramic materials (bricks or
quartz for example), ordinary enamelled steel may be
used, or glasses which have a high softening point such as
Vycor and Pyrex (trademarks).
(Steen col. 4,11. 15-21).
FF9. Smidt discloses a process for the production of carbonyl compounds.
Smidt explains that the process
4
Appeal 2014-008426
Application 12/502,342
can be carried out in all apparatus suited for the conversion
of gases with solid catalysts such as for example, tube
system or fluidized bed reactor. Of course care must be
taken that the parts of the apparatus which come into
contact with the catalyst are corrosion resistant. Suitable
corrosion resistant materials, for example, are enamel,
glass, porcelain, stone ware, synthetic resins, rubber,
titanium, tantalum, Hastelloy and the like.
(Smidt col. 4,1. 73 to col. 5,1. 6.)
Principle of Law
“If the claim extends to what is obvious, it is invalid under § 103.”
KSRInt’l Co. v. Teleflex Inc., 550 U.S. 398, 419 (2007). “Where a skilled
artisan merely pursues ‘known options’ from ‘a finite number of identified,
predictable solutions,’ the resulting invention is obvious under Section 103.”
In re Cyclobenzaprine Hydrochloride Extended-Release Capsule Patent
Litig., 676 F.3d 1063, 1070 (Fed. Cir. 2012) (quoting KSR, 550 U.S. at 421).
Analysis
The Examiner finds that Britton discloses “a process for preparing
glycerol dichlorohydrin (dichloropropanol) comprising reacting glycerol
with hydrogen chloride (chlorinating agent)” (Final Act. 5; Ans. 2; FF1—
FF4.) The Examiner recognizes that “Britton et al. differ from the claimed
invention in that Britton et al. do[es] not disclose any details of the vessel
used to carry out their reaction. However, since Britton et al. use hydrogen
chloride/hydrochloric acid in their reaction the skilled artisan would be
motivated to use a vessel that is resistant to corrosive materials” (Final
Act. 6; FF1—FF4). The Examiner concludes that because “hydrogen
chloride/hydrochloric acid is known to be corrosive[, t]he skilled artisan
5
Appeal 2014-008426
Application 12/502,342
would have been motivated to use corrosive resistant materials in order to
avoid contamination of the desired product” (Final Act. 6).
“[A] person of ordinary skill has good reason to pursue the known
options within his or her technical grasp. If this leads to the anticipated
success, it is likely that product [was] not of innovation but of ordinary skill
and common sense. In that instance the fact that a combination was obvious
to try might show that it was obvious under § 103.” KSR, 550 U.S. at 421.
Britton discloses the production of glycerol dichlorohydrin (a.k.a.
dichloropropanol) using a suitable reaction vessel (FF1—FF4). Because
Britton is silent with respect to the reaction vessel itself the Examiner
reasonably turned to other references that also use hydrogen chloride gas in
the reaction process (FF7—FF9). Steen and Smidt each teach several suitable
reaction vessels that can be used in chemical reactions utilizing hydrogen
chloride gas in the process (FF8 & FF9). A skilled artisan would have
reasonably expected success in carrying out Britton’s process in an
enameled steel reaction vessel, a corrosion-resistant material, as disclosed in
Steen or Smidt would.
The Examiner further articulated that because hydrochloric acid is a
known corrosive “[t]he skilled artisan would have been motivated to use
corrosive resistant materials in order to avoid contamination of the desired
product” (Ans. 4). Steen discloses that each of the disclosed reactors are
made of materials resistant to gaseous hydrochloric acid (FF7 & FF8). In
other words, Steen discloses multiple materials that are suitable in carrying
out reactions using hydrogen chloride gas, and any one of the reactors made
with the materials disclosed in Steen would have been obvious to use in
6
Appeal 2014-008426
Application 12/502,342
Britton’s reaction. Accordingly, we agree with the Examiner’s position that
the combination of references renders claim 1 obvious.
Selecting a suitable reaction vessel from the list of materials disclosed
in Steen and Smidt would have been obvious because each of the materials
is suitable to carry out a reaction requiring hydrogen chloride gas (FF8 &
FF9). The selection of a known material based on its suitability for its
intended use supported a prima facie obviousness determination in Sinclair
& Carroll Co. v. Interchemical Corp., 325 U.S. 327 (1945). Because any
one of the materials disclosed in Steen and Smidt is taught as suitable for
hydrochloric gas processing this renders each of the vessels equally obvious
for use in the Britton’s process and thereby sufficiently supports a finding of
obviousness. Furthermore, as the list in Steen and Smidt is small, the
ordinary artisan would have readily recognized enameled steel as one of the
suitable materials for use in a reaction vessel that is exposed to hydrogen
chloride gas in the reaction process.
We have reviewed Appellants’ contention that the Examiner erred in
rejecting the claims as obvious. We are not persuaded and adopt the
Examiner’s findings of fact and reasoning regarding the scope and content of
the prior art as set out in the Answer and Final Office Action, and agree that
claim 1 would have been obvious over the combination of Britton, Steen,
and Smidt in addition to the other listed references. We address Appellants’
arguments below.
Appellants contend that “under the conditions in Britton et ah such
corrosion would not be expected to be a problem.” (Reply Br. 2; see App.
Br. 8 (“HC1 gas is not corrosive at the temperatures used in [Britton et al]”
7
Appeal 2014-008426
Application 12/502,342
citing the Gilbeau Declaration10 in support).) “[I]t is not disputed that the
solvent used in Britton et al is in contact with water which forms by reaction
of glycerol with HC1, which is included in aqueous HC1 or which is distilled
off. . . . Such disclosure by no means suggests that a water-HCl mixture
exists in the vessel, given Britton et al’s disclosure that the water of reaction
is removed substantially as formed.” (App. Br. 11.) In other words,
Appellants contend that because the reaction temperatures in Britton are
such that corrosiveness of HC1 gas is not an issue and water is removed from
the reaction chamber, one would not look to other references for finding
vessels that resist corrosion (see App. Br. 9).
We are not persuaded. As recognized by both Appellants and the
Examiner, Britton does not disclose any particularities with respect to the
reaction vessel, stating simply that any suitable reaction vessel would suffice
(FF4 & FF6; see App. Br. 4 (“Britton et al discloses using ‘a suitable
reaction vessel’”)). Because there are no details with respect to the reaction
vessel, it would have been reasonable for an ordinary artisan to consult other
references that similarly disclose reaction procedures using hydrogen
chloride gas, as the Examiner has done here (FF7 & FF8). The Examiner
further reasoned that one of ordinary skill in the art would have been
motivated to look to reactor vessels that are corrosion resistant because one
of the byproducts of Britton’s reaction is the production of hydrochloric acid
(see Ans. 4).
10 Declaration under 35 U.S.C. § 1.1.32 by Patrick Gilbeau, signed Nov. 7,
2013.
8
Appeal 2014-008426
Application 12/502,342
We are also not persuaded by Appellants’ contention that there is no
suggestion that water-HCl mixture exists in the reaction vessel (see App. Br.
11). As explained by the Examiner,
if water is not present in the reaction mixture of Britton then why
does Britton teach employing solvents that are able to withstand
hydrolysis during the reaction and distilling steps. . . . This
disclosure implies that water is expected to be present during the
reaction and distillation steps. In fact, Britton teaches that water
forms in the reaction mixture. . . . The presence of this water
along with hydrogen chloride [gas] forms hydrochloric acid,
which is present in the reaction vessel prior to being distilled out
portionally. . . . Thus, the vessel walls of Britton are subject to
hydrochloric acid exposure.
(Ans. 8.) Britton explains that the distillate, in other words the product that
is removed from the reaction chamber, contains both aqueous hydrochloric
acid and organic solvent (FF5). This disclosure in Britton provides
sufficient evidence to support the Examiner’s position that hydrochloric acid
is present in the reaction chamber at least for some period of time even if it
is periodically or continuously removed because it would be expected that
some water is always present as more dichloropropanol is formed during the
reaction process.
Appellants point to the Gilbeau Declaration as evidencing that not all
the reaction vessels disclosed in Steen would be considered resistant to
aqueous hydrogen chloride. Appellants assert that this undermines the
Office’s position that any one of the reaction vessels in Steen would be
suitable reaction vessel in Britton (App. Br. 9; see Gilbeau Dec. 1 8 (some
metals “surprisingly do not in fact resist a reaction medium made of organic
compounds and chlorinating agent contradict the statement that ‘all of the
known corrosion resistant materials would be expected to be suitable for the
9
Appeal 2014-008426
Application 12/502,342
reaction of Britton’ and show that unique and surprising properties are
provided by enameled steel”)). Specifically, the “results of resistance tests
showing that several alloys and metals which show low corrosion rates in
boiling - 1-1.5 % HC1 aqueous solution (Monel 400, a Ni-Cu alloy;
Hastelloy C 276, a Ni-Cr-Mo alloy; Alloy 33, a Fe-Cr-Ni-Mo alloy;
Titanium grade 2, unalloyed titanium; Titanium grade 26, a Ti-Ru alloy and
Duplex SAF 2507, a Fe-Cr-Ni-Mo alloy).” (Gilbeau Dec. 1 8.)
We recognize, but are not persuaded by, the resistance testing as
shown in the Gilbeau Declaration. The Examiner explains that “the
materials used in the comparisons of Gilbeau are not known to be materials
which are as resistant to hydrochloric acid as those disclosed by Steen and
Smidt.” (Ans. 12). The Examiner notes that based on what is known about
hydrochloric acid “the results shown by Gilbeau are not unexpected” {id. at
15). We agree with the Examiner’s position that “aqueous hydrochloric acid
attacks most metals and that the rate of reaction depends on acid
concentration” (Ans. 12; see Kirth-Othermer-2, 18 (“[m]ost metals react
with aqueous HC1. . . . Tantalum and zirconium exhibit the highest
corrosion resistance to HC1”)). The art also recognizes that ceramic and
glass materials as being resistant to hydrochloric acid as evidenced by Kirk-
Othemer-2. “Glass and ceramic-coated equipment is widely used for
handling hydrochloric acid. The glass lining is normally 0.5-1.0mm (20-40
mil) thick and can be applied to various base metals” (Kirth-Othermer-2,
19). Even if some of the suggested reactor materials disclosed in Steen and
Smidt are not resistant to hydrochloric acid under the conditions tested in the
Gilbeau Declaration or under the conditions used in Britton’s reaction, some
of materials disclosed in Steen are in fact resistant, such as the enameled
10
Appeal 2014-008426
Application 12/502,342
steel vessel, as well as the glass and ceramic vessels taught by Steen and
Smidt (FF8 & FF9). O ’Farrell states that “[ojbviousness does not require
absolute predictability of success. ... all that is required is a reasonable
expectation of success.” In re O’Farrell, 853 F.2d 894, 903 (Fed. Cir.
1988). Here, the Examiner has sufficiently articulated a reason why in the
absence of any disclosure about the reaction vessel in Britton, one of
ordinary skill in the art would have looked to other references such as Steen
and Smidt to find materials that are suitable for carrying out reactions with
hydrogen chloride gas and a skilled artisan would have reasonably expected
that selecting enameled steel, a corrosion-resistant material, for use in
Britton would have been successful (see Ans. 2-4). Whether or not some of
the materials disclosed in Steen and Smidt are indeed upon further testing
found not to be as resistant to degradation by hydrogen chloride as initially
thought and disclosed in the references, such observation does not detract
from the reasonableness of the Examiner’s obviousness rejection as
articulated in the rejection.
On balance, the totality of the evidence presented favors a finding of
obviousness. Furthermore, just because some of the materials tested in the
Gilbeau Declaration are somewhat reactive with hydrochloric acid does not
mean that reactors made of those materials are not suitable for carrying out
Britton’s reaction with a reasonable expectation of producing
dichloropropanol. It is important to note that the claims do not recite any
limitation with respect to reactivity to the reactor material. There is
insufficient evidence on this record to establish that the use of an enameled
steel reactor in producing dichloropropanol provides some unexpected
11
Appeal 2014-008426
Application 12/502,342
benefit other than resistance to hydrochloric acid which was already known
and recognized in the references.
Accordingly, for the reasons discussed, we are not persuaded that the
Examiner failed to make out a prima facie case of obviousness. We are also
not persuaded that the evidence advanced by Appellants shows any
unexpected results that outweighs the evidence of prima facie obviousness.
We affirm the rejection of claim 1 under 35 U.S.C. § 103(a) as being
obvious. As claims 8, 10—14, and 18—20 have not been argued separately,
they fall together with claim 1. 37 C.F.R. § 41.37(c)(l)(iv).
Claim 9
Appellants contend because Britton’s “process continuously removes
water from the reaction zone would lead one of ordinary skill in the art to
avoid adding the extra water of associated with aqueous HC1” into the
reaction chamber (App. Br. 12).
We are not persuaded. As explained by the Examiner, “Britton places
not [sic] limits on the water content. . . and 4% or higher reads upon the
amounts disclosed in the examples of Britton” (Ans. 15.) Additionally, we
note that as long as the hydrogen chloride gas, glycerol and catalyst are
present, more water would accumulate as the reaction proceeds.
Claim 15 & 16
Appellants contend that Britton “neither discloses or suggests relating
a residence time to a ratio of the volume of liquid medium in the reactor to
the flow rate by volume of reactants” (App. Br. 13). Appellants contend that
Britton “neither discloses or suggests relating a residence time to a ratio of
the volume of liquid medium in the reactor to the flow rate by volume of
glycerol, let alone the residence time of this claim” (App. Br. 13).
12
Appeal 2014-008426
Application 12/502,342
We are not persuaded. As explained by the Examiner, “in example 1
Britton discloses the hydrogen chloride (a reactant) is continuously added
for approximately 35 hours (flow rate) at the end of which time no more
water (a liquid medium) is distilled from the reaction mixture” (Ans. 16).
Claim 17
Appellants contend that Britton “neither disclosure nor suggestion of a
particular reaction time associated with a batch process, let alone the
presently-recited reaction time of from 1 h to 10 h” (App. Br. 13).
We are not persuaded. As explained by the Examiner, “Example 4 [of
Britton] conducts a digestion for 3 hours, so there is a suggestion that the
batch reaction took at least 3 hours” (Ans. 16).
SUMMARY
We affirm the rejection of claims 1 and 8—20 under 35 U.S.C.
§ 103(a) over Britton in view of Steen and Smidt, and further in view of C.
F. Boehringer, Griesheim-Elektron, Solvay, Jakobson, and Wang.
TIME PERIOD FOR RESPONSE
No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136(a).
AFFIRMED
13