DETAILED ACTION
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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-10, in the reply filed on 06/15/2026 is acknowledged.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-2 are rejected under 35 U.S.C. 102(a)(1)/(a)(2) as being anticipated by Miller et al. (US20190201880A1).
Regarding claim 1, Miller teaches a catalyst comprising aluminum, silica (SiO2), an element E consisting of boron, and a metal (M) consisting of sodium, potassium, magnesium, calcium and combinations thereof (Abstract; [0012]). Miller teaches the catalyst displays a Raman spectrum that does not have any peaks within 1050±10 cm-1 (Fig. 6). A catalyst lacking a Raman peak at 1050±10 cm-1 would necessarily have an I2 value of zero, which would make any I2/I1 ratios derived therefrom be equal to zero, anticipating the claimed “peak height ratio I2/I1 of from 0 to 1.2.” Fig. 6 from Miller is reproduced below for convenience.
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[AltContent: textbox (Figure 1. Reproduced Fig. 6 from Miller showing the Raman spectrum of the inventive catalyst.)]
Regarding claim 2, Miller anticipates the catalyst of claim 1 and Miller teaches the catalyst displays a Raman spectrum that does not have any peaks within 1050±10 cm-1 (Fig. 6). A catalyst lacking a Raman peak at 1050±10 cm-1 would necessarily have an I2 value of zero, which would make any I2/I1 ratios derived therefrom be equal to zero, anticipating the claimed “peak height ratio I2/I1 of from 0 to 1.2.”
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C.
102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the
statutory basis for the rejection will not be considered a new ground of rejection if the prior art
relied upon, and the rationale supporting the rejection, would be the same under either status.
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 for establishing a background for determining obviousness under 35 U.S.C.
103 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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over Miller et al. (US020190201880A1).
Regarding claim 3, Miller anticipates the catalyst of claim 1. The claim further requires the catalyst “is a catalyst for producing an unsaturated carboxylic acid and/or unsaturated carboxylic acid ester” to which Miller does not explicitly discuss.
However, although Miller does not explicitly disclose the catalyst “is a catalyst for producing an unsaturated carboxylic acid and/or unsaturated carboxylic acid ester”, when the structure recited in the reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established (see MPEP 2112.01 [R-3].) In the instant case, the catalyst of Miller comprising the claimed elements X, Y, silica and a Raman spectrum lacking a peak at 1050±10 cm-1 (i.e. I2/I1 = 0) would be expected to operate as a catalyst for producing unsaturated carboxylic acid and/or unsaturated carboxylic acid ester because the catalyst of Miller and the claimed catalyst have the same or similar properties as the instantly claimed catalyst. Therefore, a rejection based alternatively on 35 U.S.C. 103 is eminently fair and acceptable.
Claims 4, 6-7, and 9 are rejected under 35 U.S.C. 103 as being unpatentable over Miller et al. (US020190201880A1) in view of Li et al. (Ind. Eng. Chem. Res. 2014, 53, 1386-1394; hereafter referred to as Li Ind. Chem.).
Regarding claim 4, Miller anticipates the catalyst of claim 1 and the claim further requires “the element X comprises zirconium,” to which Miller is silent.
Li Ind. Chem. teaches a SBA-15 (i.e. silica) supported metal-doped cesium catalyst for methyl methacrylate synthesis via condensation of methyl propionate with formaldehyde (Title; Abstract). Li teaches the metals are iron and zirconium (Pg. 1387, 2.1; Figure 1).
Advantageously, incorporating zirconium into the catalyst gives improvements in the retardation of the loss of surface area (Pg. 1390, right col.).
Thus, prior to the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to include zirconium in the catalyst of Miller in order to retard the loss of surface area as taught by Li Ind. Chem.
Regarding claim 6, Miller anticipates the catalyst of claim 1 and the claim further requires “the element Y comprises cesium,” to which Miller is silent.
Li Ind. Chem. Teaches a SBA-15 (i.e. silica) supported metal-doped cesium catalyst for methyl methacrylate synthesis via condensation of methyl propionate with formaldehyde (Title; Abstract).
Advantageously, catalysts comprising cesium display better selectivity and yield in methyl methacrylate synthesis (Abstract; Pg. 1386).
Thus, prior to the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to include cesium in the catalyst of Miller in order to provide better selectivity and yield in methyl methacrylate synthesis as taught by Li Ind. Chem.
Regarding claim 7, Miller anticipates the catalyst of claim 1 and the claim further requires “the content of element Y is from 3 to 25% by mass with respect to the total mass of the catalyst,” to which Miller is silent.
Li Ind. Chem. teaches a SBA-15 (i.e. silica) supported metal-doped cesium catalyst for methyl methacrylate synthesis via condensation of methyl propionate with formaldehyde (Title; Abstract). Li Ind. Chem. teaches cesium is present in the catalyst from 4.35 to 21.85% by weight based on the total catalyst contents (Pg. 1390, Table 2). Weight percent is equivalent to mass percent. 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). In the instant case, the range taught by Li Ind. Chem. (Cs from 4.35 to 21.85% by weight) overlaps with the claimed range (element Y is from 3 to 25% by mass). Therefore, the range in Li Ind. Chem. renders obvious the claimed ranges.
Advantageously, catalysts comprising cesium at 15 wt.% display better activity and higher dispersion of cesium on the silica support (Pg. 1392, right col.; Pg. 1392-1393, Conclusions).
Thus, prior to the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to include cesium from 4.35 to 21.85% by weight in the catalyst of Miller in order to provide better activity and a higher dispersion of cesium as taught by Li Ind. Chem.
Regarding claim 9, Miller anticipates the catalyst of claim 1 and the claim further requires “a BET specifics surface area from 50 to 600 m2/g,” to which Miller teaches a surface area of 640 m2/g [0080].
Li Ind. Chem. teaches a SBA-15 (i.e. silica) supported metal-doped cesium catalyst where the catalyst has a BET surface area from 123.3 to 369.1 m2/g when the SBA-15 support is loaded with Zr, Fe, and Cs (Title; Abstract; Table 1; Pg. 1388). 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). In the instant case, the range taught by Li Ind. Chem. (123.3 to 369.1 m2/g) overlaps with the claimed range (50 to 600 m2/g). Therefore, the range in Li Ind. Chem. renders obvious the claimed ranges.
Advantageously, providing a surface area within the range taught by Li Ind. Chem. allows reagents to enter the inner surface of the catalyst by avoiding Cs depositing in the channels of the support (Pg. 1391, left col.).
Thus, prior to the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to provide a BET surface area from 123.3 to 369.1 m2/g in the catalyst of Miller in order to allow reagents to enter the inner surface of the catalyst to allow for the conversion of reagents as taught by Li Ind. Chem.
Claims 5 and 8 are rejected under 35 U.S.C. 103 as being unpatentable over Miller et al. (US020190201880A1) in view of Li et al. (CN112844356A English; hereafter referred to as Li ‘356).
Regarding claim 5, Miller anticipates the catalyst of claim 1 and the claim further requires “a content of the element X is from 0.3 to 10% by mass with respect to the total mass of the catalyst,” where Miller teaches a convoluted chemical formula based on ratios ([0123]).
Li ‘356 teaches a catalyst for synthesizing methyl methacrylate that comprises the main active components of Cs and Al with an auxiliary agent selected from one or more of Zr, La, Ce, and Zn, that are supported on a porous SiO2 carrier (Abstract). Li ‘356 teaches the loading amount of the main active component Cs is 5-20 wt%, and the loading amount of Al is 1-10 wt% calculated according to oxides; the loading amount of the auxiliary agent is 0.1-5 wt% calculated by oxide based on the carrier (Pg. 2, par. 6). Mass percent is equivalent to weight percent. 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). In the instant case, the range taught by Li ‘356 (auxiliary agent is 0.1-5 wt%) overlaps with the claimed range (element X is from 0.3 to 10% by mass). Therefore, the range in Li ‘356 renders obvious the claimed ranges.
Advantageously, the catalyst containing the auxiliary agent concentration taught by Li ‘356 provides a catalyst with high activity, good stability, and that is suitable for large-scale industrial production (Pg. 2, par. 3).
Thus, prior to the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to include zirconium from 0.1-5 wt% by weight in the catalyst of Miller in order to provide a catalyst with high activity, good stability, and that is suitable for large-scale industrial production as taught by Li ‘356.
Regarding claim 8, Miller anticipates the catalyst of claim 1 and the claim further requires “a molar ratio MY/MX of from 1.3 to 8, wherein MX represents the number of moles of the element X, and MY represents the number of moles of the element Y,” where Miller is silent regarding this ratio.
Li ‘356 teaches the loading amount of the main active component Cs is 5-20 wt%, and the loading amount of Al is 1-10 wt% calculated according to oxides; the loading amount of the auxiliary agent is 0.1-5 wt% calculated by oxide based on the carrier (Pg. 2, par. 6). Converting the wt.% of the elements Cs (i.e. element Y) and Zr (i.e. element X) to molar amounts gives a molar ratio of Y/X of from 0.7 to 137 (calculations below). 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). In the instant case, the range taught by Li ‘356 (molar ratio of Y/X of from 0.7 to 137) overlaps with the claimed range (molar ratio MY/MX of from 1.3 to 8). Therefore, the range in Li ‘356 renders obvious the claimed ranges.
Advantageously, the catalyst containing the ratio of Y/X taught by Li ‘356 provides a catalyst with high activity, good stability, and that is suitable for large-scale industrial production (Pg. 2, par. 3).
Thus, prior to the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to provide a molar ratio of Y/X from 0.7 to 137 in the catalyst of Miller in order to provide a catalyst with high activity, good stability, and that is suitable for large-scale industrial production as taught by Li ‘356.
Calculations:
Cs molar mass = 132.905 g/mol; Zr molar mass = 91.224 g/mol
5 wt.% Cs = 5 g/100 g catalyst; 5 g Cs / 132.905 g/mol = 0.04 mol Cs
20 wt.% Cs = 20 g/100 g catalyst; 20 g Cs /132.905 g/mol = 0.15 mol Cs
0.1 wt% Zr = 0.1 g/ 100 g catalyst; 0.1 g Zr/ 91.224 g/mol = 0.001 mol Zr
5 wt% Zr = 5 g/ 100 g catalyst; 5 g Zr/ 91.224 g/mol = 0.05 mol Zr
High Zr / low Cs = 0.007
Low Zr / high Cs = 1.5
Claim 10 is rejected under 35 U.S.C. 103 as being unpatentable over Li et al. (Ind. Eng. Chem. Res. 2014, 53, 1386-1394; hereafter referred to as Li Ind. Chem.) in view of Miller et al. (US020190201880A1).
Regarding claim 10, Li Ind. Chem. teaches a method of synthesizing methyl methacrylate via condensation of methyl propionate with formaldehyde with a SBA-15 (i.e. silica) supported metal-doped cesium catalyst (Title; Abstract). Methyl methacrylate is a unsaturated carboxylic.
The claim further requires the “method uses the catalyst according to claim 1.” Li Ind. Chem. teaches a SBA-15 (i.e. silica) supported metal-doped cesium catalyst for methyl methacrylate synthesis via condensation of methyl propionate with formaldehyde (Title; Abstract). Li teaches the metals are iron and zirconium (Pg. 1387, 2.1; Figure 1).
The catalyst of claim 1 further requires a peak height ratio I2/I1 from 0 to 1.2, to which Li Ind. Chem. does not explicitly teach this property.
Miller teaches a catalyst comprising aluminum, silica (SiO2), an element E consisting of boron, and a metal (M) consisting of sodium, potassium, magnesium, calcium and combinations thereof (Abstract; [0012]). Miller teaches the catalyst displays a Raman spectrum that does not have any peaks within 1050±10 cm-1 (Fig. 6). A catalyst lacking a Raman peak at 1050±10 cm-1 would necessarily have an I2 value of zero, which would make any I2/I1 ratios derived therefrom be equal to zero, anticipating the claimed “peak height ratio I2/I1 of from 0 to 1.2.” Fig. 6 from Miller is reproduced below for convenience.
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[AltContent: textbox (Figure 2. Reproduced Fig. 6 from Miller showing the Raman spectrum of the inventive catalyst.)]
Advantageously, the catalyst of Miller is useful in conversion of aromatics and contains uniform pore openings that can allow for ions to be exchanged within the catalyst ([0002]-[0004]; [0070]-[0071]).
Thus, prior to the effective filing date of the claimed invention, it would have been obvious to one of ordinary skill in the art to provide a catalyst with a I2/I1 ratio of 0 in the catalyst when performing the method of Li Ind. Chem. in order to provide a catalyst useful in hydrocarbon conversions that also contains uniform pore openings and the ability to exchange ions into the catalyst, as taught by Miller
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jordan Wayne Taylor whose telephone number is (571)272-9895. The examiner can normally be reached Monday - Friday, 7:30 AM - 5 PM EST; Second Fridays Off.
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/JORDAN W TAYLOR/Examiner, Art Unit 1738
Prosecution Insights