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 1-15 of M. Machat et al., US 18/565,264 (Jun. 1, 2022) are pending and under examination on the merits. Claims 1, 3 and 5-15 are rejected. Claims 2 and 4 are objectionable.
Claim Interpretation
Examination requires claim terms first be construed in terms in the broadest reasonable manner during prosecution as is reasonably allowed in an effort to establish a clear record of what applicant intends to claim See MPEP § 2111. Claim interpretation is modified in this Office action over the previous in view of Applicant’s amendments.
Interpretation of the Claim 1 “proportion by mass of Al2O3”
Independent claim 1 recites “proportion by mass of Al2O3” in the following context:
1. A process for preparing aniline or an aniline conversion product, comprising:
(I) providing aminobenzoic acid;
(II) decarboxylating the aminobenzoic acid to aniline in the presence of an inorganic heterogeneous metal oxide catalyst
containing a proportion by mass of Al2O3, based on the total mass of metal oxide, of 40.0% to 100%, and
a proportion by mass of Al2O3, based on the total mass of the inorganic heterogeneous metal oxide catalyst, of 25% to 100%; and
(III) optionally converting the aniline to an aniline conversion product.
The specification teaches that the “proportion by mass of Al2O3” is calculated as follows:
In the terminology of the present invention, a metal oxide catalyst means a catalyst which contains at least one metal oxide or can be represented in terms of formula as containing at least one metal oxide.
The total mass of the metal oxides refers to the maximum number of metal oxides which can be represented in terms of formula.
If, for example, the composition of a catalyst can be represented in terms of formula as a "mixture" of aluminum oxide (Al2O3), magnesium oxide (MgO) and water (H2O) (for instance “mAl2O3 • nMgO • o H2O" - first formula), then it is generally also possible to describe the same catalyst in a second formula as a "mixture" of aluminum hydroxide (Al(OH)3) or aluminum oxide hydroxide (AIO(OH)) and magnesium hydroxide (Mg(OH)2), with neither one nor the other formula necessarily being a correct representation of the actual structure.
To determine the proportion by mass of Al2O3 for the purposes of the present invention, that description in terms of the formula which contains the maximum number of metal oxides is taken as a basis, regardless of whether or not the formula drawn up in this way adequately reflects the actual structure of the catalyst.
In this sense, the proportion by mass of Al2O3 in the sense of the present invention can therefore be a theoretical value. The first formula is therefore decisive in the example chosen. The same applies to the proportions by mass of any further metal oxides.
Specification at pages 2-3 (emphasis added). Thus, the specification defines “proportion by mass of Al2O3” as the theoretical atom amount of Al2O3 for a particular “inorganic heterogeneous metal oxide catalyst” that comprises both aluminum and oxygen, irrespective of the bonding pattern of the aluminum and oxygen. See also specification at page 1, lines 26-28.
Note that the claim 1 meaning of “inorganic heterogeneous metal oxide catalyst” encompasses zeolites, provided the zeolite meets the claim 1 “proportion by mass of Al2O3, based on the total mass of metal oxide”.
Zeolites are a member of the microporous crystalline aluminosilicates family and have three-dimensional structures which are composed of the networks of [SiO4]4− and [AlO4]5− tetrahedral linked to each other with oxygen atoms (Fig. 1 a). A. Khaleque et al., 2 Environmental Sciences, 1-24 (2020) (“Khaleque”).
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The general chemical composition of a zeolite is Ma/b [(AlO2)a(SiO2)y] . c H2O, where M represents either an alkali metal or an alkaline earth metal cation, b represents the valence earth metal cation, c is the amount of water of crystallization per unit cell and “a” and “y” represent the total number of the [SiO4]4− and [AlO4]5- tetrahedral in a unit cell of the zeolite. Khaleque at page 1, col. 1. The ratio y/a ratio (i.e., ratio [SiO4]4− / [AlO4]5-) ranges from 1 to 5. Khaleque at page 1, cols. 1-2.
Claim Objections
Claims 2 and 4 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 1, 3, 5-9, 12, 13 and 15 are rejected under AIA 35 U.S.C. 103 as being unpatentable over G. Jaeger et al., WO 2015/124686 (2015) (“Jaeger”) in view of H. Taghdisian et al., 64 Journal of Chemical & Engineering Data, 3092-3104 (2019) (“Taghdisian”); S. Veerapandian et al., 9 Catalysts, 1-40 (2019) (“Veerapandian”); and D. Miller et al., US 6,504,055 (2003) (“Miller”).
Claims 10 and 11 are obvious as claim 1 above in further view of Z. Onsan et al., Catalytic reactor types and their industrial significance, In Multiphase Catalytic Reactors, 1-16 (2016) (“Onsan”).
Claim 14 is obvious as claim 1 above in further view of B. Amini et al., Kirk-Othmer Encyclopedia of Chemical Technology, Aniline and Its Derivatives, 783-809 (2000) (“Amini”).
G. Jaeger et al., WO 2015/124686 (2015) (“Jaeger”)
Jaeger discloses method for producing aniline, comprising the steps of providing o-aminobenzoate, wherein said o-aminobenzoate comprises anthranilate anion and a suitable cation, and converting said anthranilate anion to aniline by thermal decarboxylation in the presence or absence of a catalyst. Jaeger at page 5, lines 9-16.
With respect to the catalyst, Jaeger teaches that:
. . . the catalyst, if used, can be a heterogeneous acid catalyst, preferably a zeolite, most preferably zeolite H-Y, zeolite H-Y (G0257), e.g. as obtained from Zeolyst International, catalog no. CBV600.
The acid catalyst zeolite H-Y (G0257, SiO2/Al2O3 =5.5) has a particularly high acidic character and has a wider pore size (0.7-0.8 nm) than e.g. ZSM5-27, which also possesses acidic character, but which has smaller pore size (0.5 nm) so that AA molecules cannot penetrate into them and consequently do not have access to the active sites of the acidic catalyst.
Jaeger at lines bridging pages 6-7 (emphasis added).
In working Example 3, Jaeger teaches decarboxylation of NH4+ anthranilic acid according to the procedure of Example 2, but employing zeolite H-Y as a catalyst. Jaeger at page 13, lines 10-17. Thus, Jaeger Example 3 teaches conversion of anthranilic acid to ammonium anthranilate followed by zeolite catalyzed decarboxylation in aqueous buffer solution at 160 °C. Jaeger at page 6, [0080] (citing Example 2 procedure at page 12, lines 5-14).
The Examiner summarizes Jaeger Example 3 as follows:
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Jaeger teaches that the zeolite catalysts employed were zeolite H-Y and zeolite H-ZSM5. Jaeger at page 13, lines 10-17.
Jaeger teaches that the o-aminobenzoate (anthranilic acid) can be obtained means of a recombinant microbial host that is capable of producing o-aminobenzoate by fermentation. Jaeger at page 3, lines 21-30. Jaeger teaches that such a recombinant microbial host can be E. coli W3110 trpD9923, as shown in Example 1, or it can be Corynebacterium glutamicum ATCC l3032 or it can also be Pseudomonas putida KT2440. Jaeger at page 4, lines 6-8.
Differences between Jaeger and Claim 1
Jaeger Example 3 differs from claim 1 in that the catalysts zeolite H-Y and zeolite H-ZSM5 do not meet the claims 2 limitation of:
Claim 1 . . . a proportion by mass of Al2O3, based on the total mass of the inorganic heterogeneous metal oxide catalyst, of 25% to 100% . . .
because the silicon content is too high.
H. Taghdisian et al., 64 Journal of Chemical & Engineering Data, 3092-3104 (2019) (“Taghdisian”)
Taghdisian teaches that the pore openings in zeolite 13X are larger than those of 5A. Theoretically, molecules with a kinetic diameter of 7.4 Å can be adsorbed in 13X, while this maximum allowable adsorbate molecule size for 5A is limited to 5 Å. Taghdisian at page 3092, col. 2.
Taghdisian teaches that the chemical formula of 13X is Na86[(AlO2)86(SiO2)106], in which the Si/Al ratio and molecular weight are 1.23 and 13,444 g/g mol, respectively. Taghdisian at page 3093, col. 2.
The value of “a proportion by mass of Al2O3, based on the total mass of the inorganic heterogeneous metal oxide catalyst” in zeolite 13X of formula Na86[(AlO2)86(SiO2)106] is Al86O129 (where Al86O129 is 4384g) is 4384/13,444 [Symbol font/0xB4] 100% = 33%. The value of 33% meets the claim 1 limitation of:
Claim 1 . . . a proportion by mass of Al2O3, based on the total mass of the inorganic heterogeneous metal oxide catalyst, of 25% to 100% . . .
S. Veerapandian et al., 9 Catalysts, 1-40 (2019) (“Veerapandian”)
Veerapandian teaches that zeolites are traditional adsorbents due to their unique micropores, cavities, and channels. The pore diameter in zeolites is in the range of 5–20 Å which is suitable for the adsorption of various VOC molecules. At page 4, lines 15-17.
Veerapandian teaches that the pore size of zeolite HY is 7.4 Å. Veerapandian at page 8, last full paragraph. Veerapandian teaches that the pore size of zeolite 13X is 1 nm (i.e., 10 Å). Veerapandian at page 8, 2nd paragraph. Thus, Veerapandian teaches that the pore size of zeolite 13X is a bit larger than zeolite H-Y.
D. Miller et al., US 6,504,055 (2003) (“Miller”)
Miller teaches that zeolite 13X has strong acid sites. Miller at col. 10, lines 55-57.
Obviousness Rationale
Claim 1 is obvious because one of ordinary practicing the decarboxylation of anthranilate acid to produce aniline as taught by Jaeger (for instance, Jaeger Example 3) is motivated to employ zeolite 13X as the catalyst, thereby meeting the claim 1 catalyst limitations, as well as the other claim 1 limitations. That is, as discussed above, zeolite 13X is Na86[(AlO2)86(SiO2)106], in which the Si/Al ratio and molecular weight are 1.23 and 13,444 g/g mol, respectively. Taghdisian at page 3093, col. 2. The value of “a proportion by mass of Al2O3, based on the total mass of the inorganic heterogeneous metal oxide catalyst” in zeolite 13X of formula Na86[(AlO2)86(SiO2)106] is Al86O129 (where Al86O129 is 4384g) is 4384/13,444 [Symbol font/0xB4] 100% = 33%. The value of 33% meets the claim 1 limitation of:
Claim 1 . . . a proportion by mass of Al2O3, based on the total mass of the inorganic heterogeneous metal oxide catalyst, of 25% to 100% . . .
Furthermore, zeolite 13X comprises no metal oxide other than Al2O3 (i.e., Si is not a metal) and thus meets the claim 1 limitation of:
Claim 1 . . . containing a proportion by mass of Al2O3, based on the total mass of metal oxide, of 40.0% to 100% . . .
One of ordinary skill is motivated to employ zeolite 13X as the catalyst in Jaeger’s decarboxylation because Jager teaches that zeolites are preferred catalysts. Jaeger at page 18, line 9.
One of ordinary skill is further motivated to employ zeolite 13X as the zeolite catalyst because of its similarity to Jaeger’s preferred catalyst zeolite H-Y, its favorable pore size and acidic character.
. . . the catalyst, if used, can be a heterogeneous acid catalyst, preferably a zeolite, most preferably zeolite H-Y, zeolite H-Y (G0257), e.g. as obtained from Zeolyst International, catalog no. CBV600.
The acid catalyst zeolite H-Y (G0257, SiO2/Al2O3 =5.5) has a particularly high acidic character and has a wider pore size (0.7-0.8 nm) than e.g. ZSM5-27, which also possesses acidic character, but which has smaller pore size (0.5 nm) so that AA molecules cannot penetrate into them and consequently do not have access to the active sites of the acidic catalyst.
Jaeger at lines bridging pages 6-7 (emphasis added). That is, Miller teaches that zeolite 13X has strong acid sites. Miller at col. 10, lines 55-57. And Veerapandian teaches that the pore size of zeolite 13X is a bit larger than zeolite H-Y. Veerapandian at page 8. Claim 1 is therefore obvious over Jaeger in view of the secondary art.
Claim 3 is obvious for the following reasons. In zeolite 13X, having the formula Na86[(AlO2)86(SiO2)106], the SiO2 in a proportion by mass is 3169 g/g mol and the total mass of the inorganic heterogeneous metal oxide catalyst is 13,444 g/g mol. So, the claim 3 value of:
Claim 3 . . . SiO2 in a proportion by mass, based on the total mass of the inorganic heterogeneous metal oxide catalyst . . .
for zeolite 13X is 3169/13,444 [Symbol font/0xB4] 100% = 23.5 %, which falls within the claim 3 range.
The limitations of claim 5 are met because Jaeger performs the decarboxylation at 160 °C.
Claim 6, which recites:
6. The process as claimed in claim 5, in which the decarboxylation of the aminobenzoic acid is performed at an absolute pressure of 0.05 bar to 300 bar.
is obvious for the following reasons. Jaeger teaches that the pressure in the reactor, wherein the thermal decarboxylation step b) can be performed, can be selected as a function of how much of the water and aniline is allowed to evaporate during the reaction and to leave the reactor with the CO2 produced during the thermal decarboxylation reaction. Jaeger at page 7, lines 23-25. Claim 5 is obvious because one of ordinary skill is motivated to adjust the reactor pressure to within the broad claim 5 range simply as a matter of design choice. Moreover, the general decarboxylation conditions mediated by a zeolite catalyst are set forth by Jaeger. Where the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation. MPEP § 2144.05(II) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955)). Furthermore, by way of a caption in Fig. 2, Jaeger teaches a reactor pressure of 24 bar, which falls within the claimed range. Jaeger at Fig. 2.
With respect to claims 7 and 8, the specification teaches the following regarding “the presence of aniline”. MPEP § 2111.
In one embodiment of the invention, the decarboxylation is effected in the presence of aniline, i.e. the aminobenzoic acid is dissolved in aniline. In the case of batchwise performance of the reaction, a proportion by mass of aniline, based on the total mass of aniline and aminobenzoic acid, of 0.1 % to 90%, preferably 1.0% to 70%, particularly preferably of 5.0% to 50%, is preferably established before the start of the decarboxylation. In the case of continuous performance of the reaction, a proportion by mass of aniline, based on the total mass of aniline and aminobenzoic acid, of 0.1 % to 90%, preferably 1.0% to 70%, particularly preferably 5.0% to 50%, is always established during the decarboxylation.
Specification at page 9, lines 6-13.
Claims 7 and 8 are obvious because one of ordinary skill is motivated to perform successive batch reactions, using the same reaction apparatus, where residual aniline is present, thereby meeting the further limitations of claim 7.
Claim 9 recites as follows:
9. The process as claimed in claim 7, in which the decarboxylation of the aminobenzoic acid is performed continuously and a proportion by mass of aniline, based on the total mass of aniline and aminobenzoic acid, of 0.1 % to 90% is always established during the decarboxylation.
With respect to claim 9, Jaeger teaches that in a preferred embodiment, the decarboxylation of o-aminobenzoate can be performed in a continuous manner. Jaeger at page 6, lines 14-15. Jaeger teaches that Figure 2 shows a more detailed overview of the method according to the invention. Jaeger at page 10, lines 11-12. Jaeger Figure 2 clearly diagrams a continuous process whereby ammonium anthranilate is continuously fed and decarboxylated in a reactor and a stream 5% aniline solution in water is continuously removed. Jaeger at Figure 2. Generally, differences in concentration or temperature 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). Here one of ordinary skill is motivated to practice Jaeger’s disclosed continuous process of Figure 2 where “a proportion by mass of aniline, based on the total mass of aniline and aminobenzoic acid, of 0.1 % to 90% is always established during the decarboxylation” because aniline product is continuously being formed at an established concentration. The broad range of “0.1 % to 90%” cannot distinguish over practice of Jaeger as proposed because the specification teaches no associated criticality. MPEP § 2144.05(II)(A).
Claims 10 and 11 are obvious over Jaeger and secondary art as above in further view of Z. Onsan et al., Catalytic reactor types and their industrial significance, In Multiphase Catalytic Reactors, 1-16 (2016) (“Onsan”). Jaeger teaches that in a preferred embodiment, the decarboxylation of o-aminobenzoate can be performed in a continuous manner. Jaeger at page 6, lines 14-15. Onsan teaches that in packed-bed reactors (PBRs), the solid particulate catalyst particles forming the bed are fixed in an enclosed volume and the particles are randomly packed, so there is not a regular structure, and, as a result, fluid flow takes place through irregular, random paths; the reactions take place over the active sites that are buried within the pores of the catalyst particles. Onsan at lines bridging pages 3-4. Onsan teaches that owing to their relatively simple configuration and operation, PBRs are widely used in the chemical industry; and used in high-throughput, continuous operations. Onsan at page 4, col. 1. Claims 10 and 11 are obvious because one of ordinary skill is motivated to practice Jaeger’s embodiment of decarboxylation in continuous reaction by use of a fixed bed reactor as taught by Onsan as a matter of design choice as they are taught to be widely used in the chemical industry; and used in high-throughput, continuous operations. Here, the solid particulate zeolite catalyst is well suited for use in a fixed bed reactor as taught by Onsan. One of ordinary skill is clearly motivated to practice (per claim 11) “the inorganic heterogeneous metal oxide catalyst being regenerated and reused after decarboxylation” in the interest of reaction efficiency.
Claim 12 is obvious because one of ordinary skill is motivated to prepare the o-aminobenzoate (anthranilic acid) for use in Jaeger’s decarboxylation process, as proposed above, by fermenting a raw material containing a fermentable carbon-containing compound and a nitrogen-containing compound in the presence of microorganisms because Jaeger teaches that:
(1) the o-aminobenzoate (anthranilic acid) can be obtained means of a recombinant microbial host that is capable of producing o-aminobenzoate by fermentation. Jaeger at page 3, lines 21-30; and
(2) that such a fermentation can be performed in a fermentation reactor, in which a recombinant microbial host cell capable of converting the raw material comprising a fermentable carbon substrate to o-aminobenzoate by fermentation is cultivated, in the presence of a suitable carbon source, for example com syrup, sugar can juice, molasses and the like and in the presence of a suitable nitrogen source, for example ammonia gas, ammonium hydroxide solution, ammonium sulfate, ammonium nitrate, com steep liquor and the like. Jaeger at page 5, lines 26-34.
Claim 13 is obvious because Jaeger teaches that the recombinant microbial host can be E. coli W3110 trpD9923, as shown in Example 1, or it can be Corynebacterium glutamicum ATCC l3032 or it can also be Pseudomonas putida KT2440. Jaeger at page 4, lines 6-8.
Claim 14 is obvious because one of ordinary skill is motivated to perform the claim 14 alternative of:
Claim 14 . . . (1) acid-catalyzed reaction of the aniline with formaldehyde to form di- and polyamines of the diphenylmethane series . . .
In view of B. Amini et al., Kirk-Othmer Encyclopedia of Chemical Technology, Aniline and Its Derivatives, 783-809 (2000) (“Amini”). Amini teaches that reaction of aniline hydrochloride and formaldehyde yields polymeric products; and under certain conditions, the predominant product is 4,40-methylenedianiline [101-77-9] (26), an important intermediate for 4,40-methylenebis(phenylisocyanate) [101-68-8], or MDI.
The limitations of claim 15 are clearly met.
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 G. Jaeger et al., US 10,703,709 (2020)
Claims 1, 3 and 5-15 are rejected on the ground of non-statutory double patenting as being unpatentable over conflicting claims 1 and 7 of G. Jaeger et al., US 10,703,709 (2020) or the conflicting claims in further view of G. Jaeger et al., WO 2015/124686 (2015) (“Jaeger”) and H. Taghdisian et al., 64 Journal of Chemical & Engineering Data, 3092-3104 (2019) (“Taghdisian”); S. Veerapandian et al., 9 Catalysts, 1-40 (2019) (“Veerapandian”); and D. Miller et al., US 6,504,055 (2003) (“Miller”), and additional secondary art as set forth in the § 103 rejection above. Conflicting claims 1 and 7 recite:
1. A method for producing aniline or an aniline conversion product, comprising:
(I) decarboxylating aminobenzoic acid to aniline in a reactor in the presence of a catalyst, wherein a stream containing aniline is withdrawn from the reactor;
(II) purifying a portion of the stream containing aniline withdrawn in step (I) to obtain aniline;
(III) recirculating another portion of the stream containing aniline withdrawn in step (I) into the reactor of step (I); and
(IV) optionally further reacting the aniline purified in step (II) to give an aniline conversion product.
7. The method of claim 1, in which the catalyst used in step (I) is a zeolite catalyst.
Differences between Instant Claim 1 and the Conflicting Claims
Conflicting claim 7 differs from instant claim 1 in that the genus of zeolite recited in conflicting claim 7 does teach the instant claim 1 catalyst subgenus of:
Claim 1 . . . an inorganic heterogeneous metal oxide catalyst containing a proportion by mass of Al2O3, based on the total mass of metal oxide, of 40.0% to 100%, and
a proportion by mass of Al2O3, based on the total mass of the inorganic heterogeneous metal oxide catalyst, of 25% to 100%; and
Obviousness Rationale
The same obviousness rationale applied in the § 103 rejection above also applies here. That is, instant claim 1 is obvious over conflicting claim 7 alone and/or claim 7 in further view of Jaeger/secondary art because one of ordinary practicing the decarboxylation of anthranilate acid to produce aniline mediated by a zeolite catalyst, as taught by conflicting claim 7, is motivated to employ zeolite 13X as the catalyst because it is a zeolite. One of ordinary skill thereby meets the claim 1 catalyst limitations, as well as the other claim 1 limitations. That is, as discussed above, zeolite 13X is Na86[(AlO2)86(SiO2)106], in which the Si/Al ratio and molecular weight are 1.23 and 13,444 g/g mol, respectively. Taghdisian at page 3093, col. 2. The value of “a proportion by mass of Al2O3, based on the total mass of the inorganic heterogeneous metal oxide catalyst” in zeolite 13X of formula Na86[(AlO2)86(SiO2)106] is Al86O129 (where Al86O129 is 4384g) is 4384/13,444 [Symbol font/0xB4] 100% = 33%. The value of 33% meets the claim 1 limitation of:
Claim 1 . . . a proportion by mass of Al2O3, based on the total mass of the inorganic heterogeneous metal oxide catalyst, of 25% to 100% . . .
Furthermore, zeolite 13X comprises no metal oxide other than Al2O3 (i.e., Si is not a metal) and thus meets the claim 1 limitation of:
Claim 1 . . . containing a proportion by mass of Al2O3, based on the total mass of metal oxide, of 40.0% to 100% . . .
One of ordinary skill is further motivated to employ zeolite 13X as the catalyst in in conflicting claim 7’s zeolite-mediated decarboxylation because Jager teaches that a preferred catalyst is zeolite H-Y, due to its favorable pore size and acidic character.
. . . the catalyst, if used, can be a heterogeneous acid catalyst, preferably a zeolite, most preferably zeolite H-Y, zeolite H-Y (G0257), e.g. as obtained from Zeolyst International, catalog no. CBV600.
The acid catalyst zeolite H-Y (G0257, SiO2/Al2O3 =5.5) has a particularly high acidic character and has a wider pore size (0.7-0.8 nm) than e.g. ZSM5-27, which also possesses acidic character, but which has smaller pore size (0.5 nm) so that AA molecules cannot penetrate into them and consequently do not have access to the active sites of the acidic catalyst.
Jaeger at lines bridging pages 6-7 (emphasis added). Miller teaches that zeolite 13X has strong acid sites. Miller at col. 10, lines 55-57. And Veerapandian teaches that the pore size of zeolite 13X is a bit larger than zeolite H-Y. Veerapandian at page 8. Claim 1 is therefore obvious over conflicting claim 7 and/or Jaeger in view of the secondary art.
Instant claims 3 and 5-15 are obvious over conflicting claims 1 and 13 as above, in further view of G. Jaeger et al., WO 2015/124686 (2015) (“Jaeger”) and secondary art as set forth in the § 103 rejection above.
Non-statutory Double Patenting Rejection over G. Jaeger et al., US 10,731,187 (2020)
Claims 1, 3 and 5-15 are rejected on the ground of non-statutory double patenting as being unpatentable over conflicting claims 5, 13, 29 and 30 of G. Jaeger et al., US 10,731,187 (2020) or the conflicting claims in further view of G. Jaeger et al., WO 2015/124686 (2015) (“Jaeger”) and H. Taghdisian et al., 64 Journal of Chemical & Engineering Data, 3092-3104 (2019) (“Taghdisian”); S. Veerapandian et al., 9 Catalysts, 1-40 (2019) (“Veerapandian”); and D. Miller et al., US 6,504,055 (2003) (“Miller”), and additional secondary art as set forth in the § 103 rejection above. Conflicting claims 5, 13, 29 and 30 recite:
5. A method for producing aniline, the method comprising:
a) producing o-aminobenzoate by fermentation of a raw material comprising at least one fermentable carbon substrate using the recombinant microbial host cell of claim 1, wherein said o-aminobenzoate comprises an anthranilate anion,
b) converting said o-aminobenzoate from said anthranilate anion to anthranilic acid by acid protonation,
c) recovering said anthranilic acid by precipitation or by dissolving in an organic solvent, and
d) converting said anthranilic acid to aniline by thermal decarboxylation in an organic solvent.
13. The method of claim 5, wherein step d) is performed in the presence of a catalyst
29. The method of claim 13, wherein said catalyst is a zeolite catalyst and wherein the thermal decarboxylation step d) is followed by a further step e) of purifying the aniline.
30. The method of claim 29, wherein said zeolite catalyst is zeolite H-Y.
Differences between Instant Claim 1 and the Conflicting Claims
Conflicting claim 30 differs from instant claims 29 and 30 in that zeolite or zeolite H-Y recited in the conflicting claims does teach the instant claim 1 catalyst subgenus of:
Claim 1 . . . an inorganic heterogeneous metal oxide catalyst containing a proportion by mass of Al2O3, based on the total mass of metal oxide, of 40.0% to 100%, and
a proportion by mass of Al2O3, based on the total mass of the inorganic heterogeneous metal oxide catalyst, of 25% to 100%; and
Obviousness Rationale
The same obviousness rationale applied above for US 10,703,709 and in the § 103 rejection above also applies here. That is, instant claim 1 is obvious over conflicting claims 29 and/or 30 alone or these claims in further view of Jaeger/secondary art because one of ordinary practicing the decarboxylation of anthranilate acid to produce aniline mediated by a zeolite catalyst, as taught by the conflicting claims, is motivated to employ zeolite 13X as the catalyst because it is a zeolite for the same reasons discussed above.
Provisional Non-statutory Double Patenting Rejection over M. Machat et al., US 18/853,466 (2023), Published as US 2025/0223255 (2025)
Claims 1, 3 and 5-15 are provisionally rejected on the ground of non-statutory double patenting as being unpatentable over conflicting claims 1, 13, 15 of M. Machat et al., US 18/853,466 (2023), published as US 2025/0223255 (2025) or the conflicting claims in further view of G. Jaeger et al., WO 2015/124686 (2015) (“Jaeger”) as set forth in the § 103 rejection above. The rejection is provisional because the conflicting claims have not been patented.
Conflicting claims 1 and 13 recite:
1. A process for preparing aniline or an aniline conversion product, comprising:
(A) providing aminobenzoic acid;
(B) decarboxylating the aminobenzoic acid in a reactor, wherein the aminobenzoic acid is introduced into the reactor (i) as a solid, (ii) in molten form or (iii) dissolved or suspended in a solvent and converted at a reaction temperature of 170° C to 350° C to aniline and carbon dioxide,
wherein the conversion is conducted at a reaction pressure at which the boiling point of aniline is reached or exceeded, such that (a) first, liquid, phase possibly containing solid particles and (b) a second, gaseous, phase form in the reactor, with a gaseous stream containing aniline and carbon dioxide being discharged from the reactor; and
(C) condensing and optionally purifying the aniline present in the gaseous stream; and
(D) optionally, converting the aniline obtained in (C) to an aniline conversion product.
13. The process as claimed in claim 1, in which (α) step (B) is conducted without the addition of a catalyst and without adding aniline; or
in which ([Symbol font/0x62]) step (B) is conducted in the presence of a catalyst comprising (a) an aqueous mineral acid, (b) a zeolite, ( c) an Si-Ti molecular sieve, (d) a hydroxyapatite, (e) hydrotalcite, (f) an ion-exchange resin and/or
(g) an inorganic heterogeneous metal oxide catalyst containing a proportion by mass of Al2O3, based on the total mass of the metal oxides, of 40.0% to 100%,
where the proportion by mass of Al2O3, based on the total mass of the inorganic heterogeneous metal oxide catalyst, is 25% to 100%; or
in which ([Symbol font/0x67]) step (B)(iii) is included, where the solvent comprises aniline and no catalyst is added.
Conflicting claim 13, alternative (g) recites the same catalyst as instant claim 1. Base conflicting claim 1 recites each and every method step of instant claim 1. Instant claim 1 is therefore patentably indistinct from conflicting claim 13 because it is anticipated by conflicting claim 13 alternative (g).
Instant claims 3 and 5-15 are obvious over conflicting claims 1 and 13 as above, in further view of G. Jaeger et al., WO 2015/124686 (2015) (“Jaeger”) and secondary art as set forth in the § 103 rejection above.
Terminal Disclaimer
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The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory 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.
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Subject Matter Free of the Art of Record
Claims 2 and 4 are free of the art of record. The closest art of record is G. Jaeger et al., WO 2015/124686 (2015) (“Jaeger”). As discussed above, Jaeger teaches a method for producing aniline, comprising the steps of providing o-aminobenzoate, wherein said o-aminobenzoate comprises anthranilate anion and a suitable cation, and converting said anthranilate anion to aniline by thermal decarboxylation in the presence or absence of a catalyst. Jaeger at page 5, lines 9-16.
With respect to the catalyst, Jaeger teaches that:
. . . the catalyst, if used, can be a heterogeneous acid catalyst, preferably a zeolite, most preferably zeolite H-Y, zeolite H-Y (G0257), e.g. as obtained from Zeolyst International, catalog no. CBV600.
The acid catalyst zeolite H-Y (G0257, SiO2/Al2O3 =5.5) has a particularly high acidic character and has a wider pore size (0.7-0.8 nm) than e.g. ZSM5-27, which also possesses acidic character, but which has smaller pore size (0.5 nm) so that AA molecules cannot penetrate into them and consequently do not have access to the active sites of the acidic catalyst.
Jaeger at lines bridging pages 6-7 (emphasis added). Jaeger also teaches that heterogeneous base catalyst, such as the double layered Mg-Al hydrotalcite catalyst (Mg5Al2(CO3)(OH)16 • 4H2O are suitable for the disclosed thermal decarboxylation. Jaeger at page 7, lines 7-11.
However, Jaeger does not teach or suggest the claim 2 catalyst that “contains MgO in a proportion by mass, based on the total mass of metal oxide of 1.0% to 60.0%” and also meets the base claim 1 requirement that:
Claim 1 . . . a proportion by mass of Al2O3, based on the total mass of the inorganic heterogeneous metal oxide catalyst, of 25% to 100% . . .
As correctly noted by the specification, in Jaeger’s Mg-Al hydrotalcite (Mg6Al2(CO3)(OH)16 • 4H2O, the corresponding theoretical proportion by mass of ‘Al2O3’ is 16.88%. Specification at page 1, lines 26-29.
Respecting claim 4, Jaeger does not teach or suggest [Symbol font/0x67]-Al2O3 or [Symbol font/0x68]-Al2O3 as a catalyst. As discussed in the § 103 rejection, Jaeger’s zeolites comprise a theoretical atom amount of ‘Al2O3’. See Claim Interpretation above. However, the ‘Al2O3’ in a zeolite is not [Symbol font/0x67]-Al2O3 or [Symbol font/0x68]-Al2O3. Rather, Gamma-alumina ([Symbol font/0x67]-Al2O3) and eta-alumina ([Symbol font/0x68]-Al2O3) are transition aluminas. See, G. MacZura, Calcined Alumina, Tabular Alumina, and Aluminate Cements, In Kirk-Othmer Encyclopedia of Chemical Technology, Vol. 2, pp. 403-421 (2003). Alumina is a different inorganic compound than a zeolite.
Conclusion
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ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
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