Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
DETAILED ACTION
Claims 16-30 of T. Heidemann et al., US 18/558,408 (May. 5, 2022) are pending. Claims 27-30, drawn to the non-elected inventions of Groups (V), (VI) and (VII), are withdrawn from consideration pursuant to 37 CFR 1.142(b). Claims 16-26 are under examination on the merits. Claims 16, 17 and 20-26 are rejected. Claims 18 and 19 are objectionable.
Election/Restrictions
Applicant elected Group (I), with traverse in the Reply to Restriction Requirement filed on June 8, 2026:
Group (I) drawn to a catalytic material for the hydrogenation of functional groups of organic compounds, said catalytic material comprising Ni, one or more additional metals M, and an oxidic support material comprising Zr in oxidic form and Si in oxidic form;
Towards efficient prosecution and Office guidance regarding restriction by way of linking claims, the restriction among groups (I)-(IV) is reconsidered and withdrawn. The PCT rules do not specify how claims must be restricted once unity of invention is broken, as the present case. International Preliminary Examination Under Chapter II Of The PCT, Chapter 10, Unity of Invention, (July 1, 2020). And restriction under US practice permits use of linking claims among claims that are otherwise properly divisible. MPEP § 809.03. However, the restriction among Groups (I)-(IV) is reconsidered and withdrawn, in the interest of efficient prosecution, because all claims of these groups are dependent upon claim 16.
In view of the rejoinder, the groups of inventions are now as follows:
Group (I) Claims 16-26 drawn to a catalytic material for the hydrogenation of functional groups of organic compounds, said catalytic material comprising Ni, one or more additional metals M, and an oxidic support material comprising Zr in oxidic form and Si in oxidic form;
Group (II) Rejoined with Group (I);
Group (III) Rejoined with Group (I);
Group (IV) Rejoined with Group (I);
Group (V) Claims 27 drawn to a process for the preparation of a catalytic material according to Group (I);
Group (VI) Claims 28 drawn to catalytic material obtained by the process of Group (V); and
Group (VII) Claims 29 and 30 drawn to a method comprising providing the catalytic material according to Group (I), and employing the catalytic material as a catalyst or catalyst component for a hydrogenation reaction.
Claims 27-30, drawn to the non-elected inventions of Groups (V), (VI) and (VII), are withdrawn from consideration pursuant to 37 CFR 1.142(b). The restriction/election requirement is made FINAL.
Applicant’s Traversal Regarding the Common Technical Feature
Applicant argues that A. Lange De Oliveira et al., US 2019/0233364 (2019) (“Lange De Oliveira”, cited in the previous Office action as breaking unity of invention) does not disclose or suggest the specific combination required by claim 16, namely, a catalytic material comprising Ni, one or more additional metals M, and an oxidic support comprising both Zr in oxidic form and Si in oxidic form. Reply at page 8. Applicant argues that in Lange de Oliveira, SiO2[Symbol font/0xB7]ZrO2 is described only as a support for the first catalyst embodiment, which does not include an additional metal beyond Ni. Reply at page 8. Applicant argues that while additional metals are present in Lange de Oliveira’s second and third embodiments, these utilize different supports, such as activated carbon or other metal oxides, and do not teach or suggest the simultaneous use of SiO2 and ZrO2 in the oxidic support. Reply at page 8. In sum, Applicant argues that there is insufficient motivation to combine Lange de Oliveira embodiment one with embodiment two so as to arrive at the common technical feature.
Examiner Response
This argument is not persuasive for the following reasons. As set forth in the § 103 rejection below, one of ordinary skill is motivated to modify Lange De Oliveira’s second catalyst embodiment (i.e., nickel in combination with platinum, per Lange De Oliveira at page 5, [0090]), by employing SiO2[Symbol font/0xB7]ZrO2 as the support material, because US 6,140,539 (2000) (“Sander”) teaches nitro-hydrogenation catalysts comprising nickel crystallites in combination with metals of transition group I, V, VI and/or VIII of the Periodic Table, where preference is given to using palladium, platinum, rhodium, iron, cobalt, chromium, vanadium, copper, silver or a mixture of two or more thereof can be supported on SiO2-ZrO2. Sander at col. 6, lines 42-46; Sander at col. 4, lines 30-46. This reference combination teaches the limitations of claim 16 and renders claim 16 obvious. Unity of invention is therefore lacking among the restricted Groups.
Applicant’s Argument Regarding Unexpected Results
Applicant argues that Ni, at least one additional metal M, and an oxidic support comprising both Zr and Si in oxidic form, forms the common special technical feature of the inventions across Groups I-VII of the present application. Reply at page 8. Applicant argues that the inventive contribution over the prior art is further underscored by the technical effects demonstrated in the examples. Specifically, the catalytic material of the present invention is particularly suitable for the hydrogenation of nitro group-containing compounds. Experimental data (Examples 1 and 2) show that the catalyst achieves remarkable stability and selectivity: a TDA selectivity of at least 98.9% after 100 hours and at least 98.6% after 200 hours time on stream, compared to Comparative Example 1 (prior art), which showed 98.6% after 100 hours and only 97.1 % after 200 hours and selectivity towards by-products is markedly lower with the inventive catalyst. Reply at page 8. Applicant argues that these results clearly evidence a surprising and advantageous effect attributable to the specific combination of features claimed. Reply at page 8.
Examiner Response
This argument is not persuasive because there does not appear to be a legal basis for overcoming restriction based on lack of unity of invention in view of unexpected results. International Preliminary Examination Under Chapter II Of The PCT, Chapter 10, Unity of Invention, (July 1, 2020).
Further, the proffered unexpected results of specification Examples 1 and 2 are not persuasive of overcoming a § 103 issue at least because they are not commensurate in scope with the claims. MPEP § 716.02(d). In specification Example 1, the catalytic material comprises Ni (70.7 wt%), Re (3.0 wt%), and the support material comprises ZrO2 and SiO2 at a specific wt%. Specification at pages 36-37. In specification Example 2, the catalytic material comprises Ni (72.8 wt%), Pt (0.2 wt%), and the support material comprises ZrO2 and SiO2 at a specific wt%. Specification at pages 37-38. The proffered catalysts are clearly not commensurate with, for example the supported catalyst of claim 16, which claims nickel as well as ZrO2/SiO2 support in any amount and where claim 16 permits the additional metal can be any of Re, Ru, Os, Rh, Ir, Pd, and Pt (where the proffered results are directed only to Re and Pt) in a range of from 0.01 to 10 weight-%. MPEP § 716.02(d).
Claim Objections
Claims 18 and 19 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under AIA 35 U.S.C. 103(a) are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 16, 20 and 23-26 are rejected under AIA 35 U.S.C. 103 as being unpatentable over A. Lange De Oliveira et al., US 2019/0233364 (2019) (“Lange De Oliveira”) in view of M. Sander et al., US 6,140,539 (2000) (“Sander”) and/or P. Birke et al., US 6,680,280 (2004) (“Birke”).
Claims 17, 21 and 22 are rejected under AIA 35 U.S.C. 103 over Lange De Oliveira in view of Sander and/or Birke, as above, in further view of U. Birkenstock et al., US 5,120,875 (1992) (“Birkenstock”).
A. Lange De Oliveira et al., US 2019/0233364 (2019) (“Lange De Oliveira”)
Lange De Oliveira teaches continuous hydrogenation of a nitro compound to the corresponding amine using a supported catalyst. Lange De Oliveira at pages 1-2, [0015]. Lange De Oliveira is directed to the same utility as the instant application, that is a nickel-based hydrogenation catalyst for nitro groups.
Lange De Oliveira teaches that the active component of the supported catalyst preferably comprises at least one element from groups 7 to 12 of the periodic table of the elements, particularly preferably at least one element from the group consisting of nickel, platinum, palladium and cobalt and especially preferably at least nickel. Lange De Oliveira at page 5, [0070] (emphasis added). Lange De Oliveira teaches the catalyst generally comprises 0 to 10 wt %, preferably 1 to 5 wt %, of noble metal based on the total weight of the catalyst. Lange De Oliveira at page 5, [0071]. Platinum is a noble metal.
First Catalyst Embodiment
Lange De Oliveira teaches that in a first embodiment nickel may be used as the active component on a support as described in U.S. Pat. No. 6,140,539, wherein the catalyst is stabilized and the nickel crystallites. Lange De Oliveira at page 5, [0075].
Lange De Oliveira teaches that the support in this first embodiment preferably comprises ZrO2, ZrO2HfO2, SiO2[Symbol font/0xB7]ZrO2 or SiO2[Symbol font/0xB7]ZrO2HfO2 or mixtures comprising at least two of these substances, where the SiO2 content is preferably 0 to 20 wt % based on the total mass of the catalyst, the ZrO2 content is preferably 0 to 40 wt% based on the total mass of the catalyst., the HfO2 content is preferably 0 to 4 wt% based on the total mass of the catalyst. Lange De Oliveira at page 5, [0078]-[0081].
Second Catalyst Embodiment
Lange De Oliveira teaches that in a second embodiment the process according to the invention for continuous hydrogenation of nitro compounds to the corresponding amines uses a supported catalyst whose active component comprises a mixture of nickel and platinum and optionally at least one additional metal, as described in EP 1678118B1 [US 2007/0149814] or DE 102005041532A1 [US 2008/0242537]. Lange De Oliveira at page 5, [0084]. Lange De Oliveira teaches the additional metal is particularly preferably at least one metal from the group consisting of copper, cobalt, iron and zinc. Lange De Oliveira at page 5, [0086].
Respecting this second catalyst embodiment, Lange De Oliveira teaches the following catalyst:
[0090] The hydrogenation catalyst based on nickel and platinum and at least one additional metal and used in the process according to the invention is particularly preferably composed of
1 to 5 wt % of platinum,
0.3 to 1.5 wt% of nickel,
0.05 to 1.5 wt % of the at least one additional metal and
94.65 to 97.45 wt% of support material,
each based on the total weight of the catalyst, wherein the sum amounts to 100 wt%.
Lange De Oliveira at page 5, [0090]. Lange De Oliveira teaches that supports for the catalysts of this second embodiment are generally known to one skilled in the art or are described in EP 1678118B1 [US 2007/0149814] or DE 102005041532A1 [US 2008/0242537], where activated carbon, carbon black, graphite or metal oxides, preferably hydrothermally stable metal oxides, for example ZrO2 and/or TiO2, or oxides of aluminum, such as Al2O3, or of silicon or other materials are generally employed, where graphite is a preferred support. Lange De Oliveira at page 6, [0092].
Third Catalyst Embodiment
Lange De Oliveira teaches in a third embodiment of the process according to the invention catalysts may be employed which comprise as the active component a mixture of nickel, palladium and an additional element selected from the group consisting of cobalt, iron, vanadium, manganese, chromium, platinum, iridium, gold, bismuth, molybdenum, selenium, tellurium, tin and antimony on a support. Lange De Oliveira at page 6, [0099].
Lange De Oliveira teaches that as the support for the catalyst of this third embodiment the materials known and customary therefor may generally be employed; preferable activated carbon, carbon black, graphite or hydrothermally stable metal oxides such as ZrO2, TiO2, Al2O3, where particular preference is given to activated carbons, in particular physically or chemically activated carbons, or carbon blacks, such as acetylene black. Lange De Oliveira at page 6, [0099].
Lange De Oliveira teaches that the performance of a hydrogenation of nitro compounds to the corresponding amines using this catalyst is generally known to one skilled in the art or is described in WO 2008/138784 [US2010/0130788].
Differences between Lange De Oliveira and Claim 16
It is first noted that instant claim 16 requires one or more additional metal in a “range of from 0.01 to 10 weight-%”
16 . . . wherein the one or more additional metals M are selected from the group consisting of Re, Ru, Os, Rh, Ir, Pd, and Pt, and
wherein the catalytic material comprises the one or more additional metals M in an amount in the range of from 0.01 to 10 weight-% . . .
Claim 16 requires the percentage be calculated as follows:
16 . . . calculated as sum of the weights of the one or more additional metals M calculated as the elements, respectively, and
based on 100 weight-% of the sum of the weights of Ni and of the one or more additional metals M calculated as the elements, respectively, and of Zr and Si calculated as the oxides ZrO2 and SiO2, respectively.
The Examiner puts this claim 16 recitation in the form of the following equation:
PNG
media_image1.png
200
400
media_image1.png
Greyscale
Lange De Oliveira teaches the limitations of claim 16 (where the additional claim 16 metal is platinum) but does not put them together in a single embodiment and does not teach the specific claim 16 range of additional metal. That is, respecting the second catalyst embodiment, Lange De Oliveira teaches the following catalytic material:
[0090] The hydrogenation catalyst based on nickel and platinum and at least one additional metal and used in the process according to the invention is particularly preferably composed of
1 to 5 wt % of platinum,
0.3 to 1.5 wt% of nickel,
0.05 to 1.5 wt % of the at least one additional metal and
94.65 to 97.45 wt% of support material,
each based on the total weight of the catalyst, wherein the sum amounts to 100 wt%.
Lange De Oliveira at page 5, [0090].
For this particular second-embodiment catalyst, Lange De Oliveira teaches hydrothermally stable metal oxides, generally, such as ZrO2, TiO2, Al2O3. Lange De Oliveira at page 6, [0092]. But does not specifically, teach the claim 16 support of “oxidic support material comprising Zr in oxidic form and Si in oxidic form”, for this second-embodiment catalyst.
However, Lange De Oliveira does teach claim 16 support of “oxidic support material comprising Zr in oxidic form and Si in oxidic form” for the first catalyst embodiment where nickel may be used as the active component on a support (this first Lange De Oliveira catalyst embodiment as described in U.S. Pat. No. 6,140,539, which is reference Sander below). Lange De Oliveira at page 5, [0075]. In this first catalyst embodiment, Lange De Oliveira/Sander teach that the support may be SiO2[Symbol font/0xB7]ZrO2. Lange De Oliveira at page 5, [0078]-[0081].
Thus, substituting Lange De Oliveira’s first-catalyst-embodiment support of SiO2[Symbol font/0xB7]ZrO2 for the support of Lange De Oliveira’s second catalyst embodiment meets the limitations of claim 16.
M. Sander et al., US 6,140,539 (2000) (“Sander”)
Sander teaches a process for preparing amines by hydrogenation of the corresponding nitro compounds. Sander at col. 1. Ines 4-5. Sander was cited by Lange De Oliveira, with respect to Lange De Oliveira’s first catalyst embodiment.
Sander is directed to the same utility as the instant application, that is a nickel-based hydrogenation catalyst for nitro groups.
Sander teaches a process for preparing amines, in particular aromatic amines, in which at least one compound containing at least one nitro group is hydrogenated in the presence of a supported catalyst comprising, as catalytically active metal, nickel, if desired together with at least one metal of transition group I, V, VI and/or VIII, wherein the reduced and stabilized supported catalyst comprises nickel crystallites having a bimodal nickel crystallite size distribution having maxima at 30-80 Angström and 81–150 Angström on a support comprising ZrO2, ZrO2 HfO2 and/or SiO2-ZrO2 and/or SiO2-ZrO2-HfO2 and in the reduced and passivated state has a nickel content of 60-80 percent by mass, an SiO2 content of 0-20 percent by mass, a ZrO2 content of 0-40 percent by mass, an HfO2 content of 0-4 percent by mass and after further reduction for one hour at 100° C has a degree of reduction of at least 70%. Sander at col. 4, lines 30-46 (emphasis added).
Sander teaches that as metals of transition group I, V, VI and/or VIII of the Periodic Table, preference is given to using palladium, platinum, rhodium, iron, cobalt, chromium, vanadium, copper, silver or a mixture of two or more thereof. Sander at col. 6, lines 42-46 (emphasis added).
Sander teaches that the process of the present invention makes it possible to carry out the hydrogenation of nitroaromatics at significantly lower catalyst concentrations in the hydrogenation bath than in the known processes. Sander at col. 7, lines 30-35.
P. Birke et al., US 6,680,280 (2004) (“Birke”)
Birke is directed to the same utility as the instant application, that is a nickel-based hydrogenation catalyst for nitro groups. Birke at Abstract; Id. at cols. 7-8 (Example 5); instant specification at page 12, lines 31-40.
Birke teaches a reduced catalyst having nickel crystallites with a bimodal nickel crystallite size distribution, a nickel content of from 60, in particular 61% by mass to 80% by mass (based on the total mass of the catalyst) and a degree of reduction of at least 70%. Birke at col. 2, lines 13-19. Birke teaches that in preferred embodiment, the above-mentioned catalyst is supported on a zirconium containing support, preferably contains or consists of ZrO2, ZrO2HfO2, SiO2.ZrO2, SiO2.ZrO2HfO2 or mixtures of at least two of these substances. Birke at col. 2, lines 31-99. Birke teaches that in a particularly preferred embodiment, the SiO2 content is 0 to 20% by mass (based on the total mass of the catalyst) and the ZrO2 content is 20 to 40% by mass (based on the total mass of the catalyst). Birke at col. 2, lines 36-41.
Birke teaches the following working Examples 2 and 3 of the disclosed nickel hydrogenation catalysts. Birke at cols 5-7.
Content of Birke Working Examples 2 and 3
Example
Ni
ZrO2
SiO2
2
65%
18%
3%
3
60%
16%
5%
In working Example 5, Birke teaches that catalyst Example 2 gave a 99.85% yield in the hydrogenation of nitrobenzene to form aniline. Birke at cols. 7-8 (data in Table at col. 8).
U. Birkenstock et al., US 5,120,875 (1992) (“Birkenstock”)
Birkenstock teaches an active-charcoal supported nickel/platinum catalyst, for hydrogenation of chlorinated aromatic nitro compounds to the corresponding amines. Birkenstock at col. 1, line 65 to col. 2, line 18.
A catalyst on active charcoal as the support material is employed as hydrogenation catalyst in the process according to the invention. The catalyst contains platinum, for example in an amount of 0.3 to 7% by weight, preferably 0.5 to 2% by weight, and nickel and/or cobalt, for example in each case in amounts of 1 to 100% by weight, preferably 10 to 30% by weight, based on the platinum. Catalysts which contain platinum and nickel are particularly preferred.
The active charcoal support for the catalyst can consist of any desired porous or non-porous material.
Birkenstock at col. 2, lines 54-64 (emphasis added).
Obviousness Rationale
Claim 16 is obvious because one of ordinary skill is motivated to by Sander and/or Birke to employ SiO2[Symbol font/0xB7]ZrO2 as the support material for Lange De Oliveira catalytic material of the following paragraph [0090]:
[0090] The hydrogenation catalyst based on nickel and platinum and at least one additional metal and used in the process according to the invention is particularly preferably composed of
1 to 5 wt % of platinum,
0.3 to 1.5 wt% of nickel,
0.05 to 1.5 wt % of the at least one additional metal and
94.65 to 97.45 wt% of support material,
each based on the total weight of the catalyst, wherein the sum amounts to 100 wt%.
Lange De Oliveira at page 5, [0090]. Upon making such substitution, one of ordinary skill arrives at a SiO2[Symbol font/0xB7]ZrO2 supported nickel (0.3 to 1.5 wt%) and platinum (1 to 5 wt %) catalyst where per the following claim 16 calculation:
Claim 16 . . . wherein the Ni is supported on the oxidic support material,
wherein the one or more additional metals M are selected from the group consisting of Re, Ru, Os, Rh, Ir, Pd, and Pt, and
wherein the catalytic material comprises the one or more additional metals M in an amount in the range of from 0.01 to 10 weight-%,
calculated as sum of the weights of the one or more additional metals M calculated as the elements, respectively, and
based on 100 weight-% of the sum of the weights of Ni and of the one or more additional metals M calculated as the elements, respectively, and of Zr and Si calculated as the oxides ZrO2 and SiO2, respectively.
The cited weight percent of platinum of 0.01 to 5 wt % falls within the claim 16 range of “from 0.01 to 10 weight-%”. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP § 2144.05(I). The above proposed modification meets each element of claim 16, where the “one or more additional metals M” is Pt.
One of ordinary skill is motivated to modify Lange De Oliveira, as proposed above, because Lange De Oliveira teaches hydrothermally stable metal oxides, generally, as suitable supports for catalyst embodiment two (Lange De Oliveira at page 6, [0092]) and Sander teaches nitro-hydrogenation catalysts comprising nickel crystallites in combination with metals of transition group I, V, VI and/or VIII of the Periodic Table, where preference is given to using palladium, platinum, rhodium, iron, cobalt, chromium, vanadium, copper, silver or a mixture of two or more thereof can be supported on SiO2-ZrO2. Sander at col. 6, lines 42-46; Sander at col. 4, lines 30-46. Birke provides similar teachings. In this regard, Sander teaches that the process of the present invention makes it possible to carry out the hydrogenation of nitroaromatics at significantly lower catalyst concentrations in the hydrogenation bath than in the known processes. Sander at col. 7, lines 30-35. Claim 16 is therefore obvious in view of the cited art.
Claims 17 and 21 are obvious over Lange De Oliveira and Sander, as above, in further view of U. Birkenstock et al., US 5,120,875 (1992) (“Birkenstock”). Claim 17 requires a Ni to additional metal (M) atomic ratio of “in the range of from 10:1 to 2000:1”.
17. The catalytic material according to claim 16,
wherein the catalytic material exhibits an atomic ratio, Ni:M, of Ni, calculated as atomic amount of Ni comprised in the catalytic material,
to the one or more additional metals M,
calculated as sum of the atomic amounts of the respective additional metals M comprised in the catalytic material,
in the range of from 10:1 to 2000:1.
Claim 21 recites similarly, but states an atomic ratio of “250:1 to 2000:1”. Birkenstock teaches that for hydrogenation of chlorinated aromatic nitro compounds to the corresponding amines a preferred range is 0.3 to 7% by weight of nickel and 0.3 to 7 wt % of platinum” in the catalyst. Birkenstock at col. 2, lines 54-64. Birkenstock’s ranges (in the case of a 100 g of catalyst) convert to an Ni atom number range of 170 mmol to 511 mmol and a Pt atom number range of 1.5 mmol to 10 mmol Pt. Thus, the atomic ratio of nickel to platinum taught by Birkenstock overlaps with the claim 17 and 21 ranges. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP § 2144.05(I). Further, differences in concentration or temperature generally will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. MPEP § 2144.05(II)(A) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). Here, one of ordinary skill seeking to use the above proposed modified Lange De Oliveira SiO2[Symbol font/0xB7]ZrO2 supported Ni/Pt catalyst for hydrogenation of chlorinated aromatic nitro compounds is motivated to optimize the Ni/Pt atomic ratio within the ranges taught by Birkenstock, which overlap with the claim 17 and 21 ranges. Claims 17 and 21 are therefore obvious over Lange De Oliveira and Sander in further view of Birkenstock.
Claim 20 is obvious over Lange De Oliveira in view of Sander because the further limitations of claim 20 are clearly met by platinum as the additional metal M as proposed above.
Claim 22 is obvious over Lange De Oliveira and Sander, as above, in further view of Birkenstock under a similar rationale for claims 17 and 21. Claim 22 recites as follows:
22. The catalytic material according to claim 16,
wherein the catalytic material comprises from 50 to 97 weight-% of Ni, calculated as elemental Ni, and
based on 100 weight-% of the sum of the weights of Ni and of the one or more additional metals M calculated as the elements, respectively, and of Zr and Si calculated as the oxides ZrO2 and SiO2, respectively.
As discussed above, for hydrogenation of chlorinated aromatic nitro compounds, Birkenstock teaches 1 to 100% by weight, by weight of nickel and 0.3 to 7 wt % of platinum” in the catalyst. Birkenstock at col. 2, lines 54-64 (emphasis added). Claim 22 is obvious because one of ordinary skill seeking to use the above proposed modified Lange De Oliveira SiO2[Symbol font/0xB7]ZrO2 supported Ni/Pt catalyst for hydrogenation of chlorinated aromatic nitro compounds is motivated to optimize the Ni amount to within the ranges taught by Birkenstock, which overlaps with the claim 22 Ni range. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP § 2144.05(I).
Claims 23 and 24 are obvious over Lange De Oliveira and Sander, as above, in further view of Birke. Claims 23 and 24 recites as follows:
23. The catalytic material according to claim 16,
wherein the catalytic material comprises from 2 to 25 weight-% of Zr, calculated as elemental Zr, and
based on 100 weight-% of the sum of the weights of Ni and of the one or more additional metals M calculated as the elements, respectively, and of Zr and Si calculated as the oxides ZrO2 and SiO2, respectively.
24. The catalytic material according to claim 16,
wherein the catalytic material comprises from 0.3 to 3.0 weight-% of Si,
calculated as elemental Si, and based on 100 weight-% of the sum of the weights of Ni and of the one or more additional metals M calculated as the elements, respectively, and of Zr and Si calculated as the oxides ZrO2 and SiO2, respectively.
Sander teaches a support comprising ZrO2, ZrO2 HfO2 and/or SiO2-ZrO2 and/or SiO2-ZrO2-HfO2 and in the reduced and passivated state has a nickel content of 60-80 percent by mass, an SiO2 content of 0-20 percent by mass, a ZrO2 content of 0-40 percent by mass, an HfO2 content of 0-4 percent by mass and after further reduction for one hour at 100° C has a degree of reduction of at least 70%. Sander at col. 4, lines 30-46 (emphasis added).
Birke teaches that in a particularly preferred embodiment, the SiO2 content is 0 to 20% by mass (based on the total mass of the catalyst) and the ZrO2 content is 20 to 40% by mass (based on the total mass of the catalyst). Birke at col. 2, lines 36-41. Birke teaches the following working Examples 2 and 3 of the disclosed nickel hydrogenation catalysts. Birke at cols 5-7.
Content of Birke Working Examples 2
Example
Ni
ZrO2
SiO2
2
65%
18%
3%
The ranges of Zr (calculated as ZrO2) and Si (calculated as SiO2) taught by Sander and Birke overlap with the claim 23 and 24 ranges. Further Birke teaches working Example 2, where the Zr (calculated as ZrO2) and Si (calculated as SiO2) respectively fall within the claim 23 and 24 ranges. Birke at col. 6, lines 47-50. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP § 2144.05(I). Here, claims 23 and 24 are obvious because one of ordinary skill seeking to use the above proposed modified Lange De Oliveira SiO2[Symbol font/0xB7]ZrO2 supported Ni/Pt catalyst for hydrogenation, is motivated to optimize the amounts of Zr (calculated as ZrO2) and Si (calculated as SiO2) within the ranges taught by Sander and/or Birke because such ranges lead to effective catalyst supports for nickel-based catalysts.
Claims 25 and 26 are obvious over Lange De Oliveira and Sander, as above, because both Sander and Lange De Oliveira teaches the catalyst introduced into the reactor in a reduced state which indicates conversion of the nickel salts to elemental nickel. Lange De Oliveira at page 6, [0014]; Sander at col. 4, lines 54-5. Respecting claim 26, Sander teaches a degree of reduction of at least 70%. Sander at col. 4, lines 45-46.
Non-Statutory Double Patenting
The non-statutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A non-statutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
Non-statutory Double Patenting Rejection over A. Lange De Oliveira et al., US 10,538,478 (2020)
Claims 16, 20 and 23-26 are rejected on the ground of non-statutory double patenting as being unpatentable over conflicting claim 4 of A. Lange De Oliveira et al., US 10,538,478 (2020) in view of M. Sander et al., US 6,140,539 (2000) (“Sander”) and/or P. Birke et al., US 6,680,280 (2004) (“Birke”)
Claims 17, 21 and 22 are rejected on the ground of non-statutory double patenting as being unpatentable over conflicting claim 4 of A. Lange De Oliveira et al., US 10,538,478 (2020) in view of Sander and/or Birke, as above, in further view of U. Birkenstock et al., US 5,120,875 (1992) (“Birkenstock”).
Conflicting claim 4 recites
Conflicting claim 4. The process of claim 1, wherein the supported catalyst comprises
1 to 5 wt % of platinum,
0.3 to 1.5 wt% of nickel,
0.05 to 1.5 wt % of the at least one additional metal and
94.65 to 97.45 wt% of support material,
based on the total weight of the catalyst, wherein the sum amounts to 100 wt%.
where conflicting claim 1 is directed to a process for continuous hydrogenation of dinitrotoluene in the presence of a supported catalyst. Conflicting claim 4 teaches the same catalyst that is the basis of the above § 103 rejection over A. Lange De Oliveira et al., US 2019/0233364 (2019) (“Lange De Oliveira”).
Instant claims 16, 20 and 23-26 are patentably indistinct from conflicting claim 4 of A. Lange De Oliveira et al., US 10,538,478 (2020) in view of secondary art M. Sander et al., US 6,140,539 (2000) (“Sander”) and/or P. Birke et al., US 6,680,280 (2004) (“Birke”) under the same reasoning give above in the § 103 rejection.
Instant claims 17, 21 and 22 are patentable indistinct from conflicting claim 4 of A. Lange De Oliveira et al., US 10,538,478 (2020) in view of secondary references Sander and/or Birke, as above, in further view of U. Birkenstock et al., US 5,120,875 (1992) (“Birkenstock”) under the same reasoning give above in the § 103 rejection. .
Terminal Disclaimer
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on non-statutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a non-statutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Subject Matter Free of the Art of Record
Claims 18 and 19 are free of the art of record. Claims 18 and 19 require that the “one or more additional metals M” of base claim 16 be rhenium (Re). This limitation distinguishes claims 18 and 19 over the art.
The closest art of record is A. Lange De Oliveira et al., US 2019/0233364 (2019) (“Lange De Oliveira”) as discussed in detail above. Lange De Oliveira teaches continuous hydrogenation of a nitro compound to the corresponding amine using a supported catalyst. Lange De Oliveira at pages 1-2, [0015].
Also as discussed above, respecting the second catalyst embodiment, Lange De Oliveira teaches the following catalytic material:
[0090] The hydrogenation catalyst based on nickel and platinum and at least one additional metal and used in the process according to the invention is particularly preferably composed of
1 to 5 wt % of platinum,
0.3 to 1.5 wt% of nickel,
0.05 to 1.5 wt % of the at least one additional metal and
94.65 to 97.45 wt% of support material,
each based on the total weight of the catalyst, wherein the sum amounts to 100 wt%.
Lange De Oliveira at page 5, [0090]. For this particular second-embodiment catalyst, Lange De Oliveira teaches hydrothermally stable metal oxides, generally. Lange De Oliveira at page 6, [0092]. As argued above, base claim 16 is obvious because one of ordinary skill is motivated by Sander and/or Birke to employ SiO2[Symbol font/0xB7]ZrO2 as the support material for Lange De Oliveira catalytic material of above paragraph [0090], thereby arriving at each element of claim 16.
With respect to claims 18 and 19 (which require rhenium as the additional metal M), Lange De Oliveira teaches that the supported catalyst generally comprises at least one element from groups 7 to 12 of the periodic table of the elements as the active component, where suitable active components include, for example, iron, cobalt, nickel, ruthenium, rhodium, palladium, silver, osmium, iridium, platinum, gold, copper, rhenium, zinc and/or manganese. Lange De Oliveira at page 4-5, [0069]. However, this is the only mention of rhenium in Lange De Oliveira, with no working examples or other guidance respecting rhenium. Thus, Lange De Oliveira itself provides little motivation to specifically select rhenium as the instantly claimed secondary metal from Lange De Oliveira’s listing, for use in combination with nickel.
Secondary reference Liu teaches the addition of Re to Ni on TiO2 yields efficient catalysts for the hydrogenation of acids and esters to alcohols under mild conditions. Rhenium promotes the formation of atomically dispersed and sub-nanometre-sized bimetallic species interacting strongly with the oxide support. K. Liu et al., 53 ChemComm, 9761-9764 (2017) (“Liu”) (see Abstract). While one of ordinary skill arrives as the limitations of claim 18 by combining Liu with Lange De Oliveira/Sander, there is insufficient motivation to make this reference combination at least because Liu provides no teaching or suggestion of supports other than TiO2.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALEXANDER R PAGANO whose telephone number is (571)270-3764. The examiner can normally be reached 8:00 AM through 5:00 PM.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format.
For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
Prosecution Insights