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 .
Election/Restrictions
Applicant’s election without traverse of claims 1-10 in the reply filed on 5 December 2025 is acknowledged.
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 (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 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.
Claim(s) 1-5 and 7-9 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zeidan et al in the Journal of Catalysis (2006, vol 239, pp 299-306).
With respect to claims 1, 5, 7, and 9, Zeidan et al discloses “a thiol/sulfonic acid functionalized SBA-15,” which is obtained by Scheme 1:
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Zeidan et al further teaches “one-pot syntheses of SBA-15 that simultaneously incorporate sulfonic acid and thiol functional groups through co-crystallization were used to create a set of solid materials that immobilize these two functional groups at varying ratios. By adding 3-mercaptopropyltrimethoxysilane and 2-(4-chlorosulfonylphenyl)-ethyltrimethoxysilane (sulfonyl chloride hydrolyzes under acidic synthesis conditions) to a mixture of TEOS, 2.0M HCl, H2O, and P123 (53:348:484:1), SBA-15 functionalized with thiol and sulfonic acid was obtained” [last paragraph on left hand side of page 302 and first paragraph on right hand side of the same]. Note that the sulfonic acid functionalized silica in the scheme above is an ethylbenzenesulfonic acid silica (brought about by the (phenyl-ethyl) and corresponds to the acidic heterogeneous catalyst comprising amorphous silica having organosulfonic acid groups chemically bonded thereto, wherein the catalyst has a pKa value of 3.5 or less of the instant application. While Zeidan et al does not explicitly disclose the pKa value of the ethylbenzenesulfonic acid silica, the instant application discloses “[n]on-limiting examples of suitable organosulfonic acid functionalized silica compounds having the required pKa value of 3.5 or less include…ethylbenzenesulfonic acid silica” [paragraph 0021 of the published application]. Consequently, the pKa limitation is obvious. Moreover, the thiol functionalized silica corresponds to the catalyst promoter of the instant application.
With respect to claim 2, Zeidan et al discloses “[p]owder X-ray diffraction (XRD) data were acquired on a Brucker D5005 diffractometer using Cu-Kα radiation” [first paragraph under heading “2.3 Characterization”]. Furthermore, it is well known in the art that SBA-15 prepared in a manner similar to that of Zeidan et al (with P123, HCl, and TEOS) may in in powder form, which powder corresponds to the particles of the instant claim.
With respect to claim 3, it is well known in the art that SBA-15 may also be prepared by an extrusion method to produce granules, which corresponds to extrudates comprising silica particles.
With respect to claim 4, Zeidan et al does not disclose zirconium; therefore, absent evidence to the contrary, it is expected that the SBA-15 functionalized with thiol and sulfonic acid is substantially free of zirconium.
With respect to claim 8, the thiol appears to be a propyl mercaptan (propanethiol) [see Scheme 1 above].
Claim(s) 6 and 10 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zeidan et al in the Journal of Catalysis (2006, vol 239, pp 299-306) as applied to claims 1-5 and 7-9 above and in further view of Dufaud et al in the Journal of the American Chemical Society (2003, 125, 9403-9413).
With respect to claim 6, clearly, ethylbenzenesulfonic acid silica does not contain an R1 group having from 1 to 4 carbons.
However, Dufaud et al, which is concerned with “the condensation reaction of phenol and acetone to bisphenol A” [abstract], discloses “[t]he alkyl sulfonic acid modified material 10•SBA derived from the cleavage and oxidation of the dipropyl disulfide modified material 3•SBA is more active than not only its monosite analogue 9•SBA, but also the presumably stronger acid aryl sulfonic acid material 11•SBA” [see, again, abstract], wherein 9•SBA has the molecular structure depicted in the upper left hand corner of figure 7 and 10•SBA has the molecular structure depicted in the upper right hand corner of the same and the SBA support is SBA-15 like Zeidan et al.
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Note that 9•SBA and 10•SBA have R1 groups with 3 carbons.
At the time of the effective filing date of the instant application, it would have been obvious to one of ordinary skill in the art to either (1.) substitute 9•SBA and/or 10•SBA for the ethylbenzenesulfonic acid silica of Zeidan et al, which corresponds to 11•SBA ([Si]-CH2CH2aryl-SO3H—see Table 1] or (2.) add 9•SBA and/or 10•SBA to the ethylbenzenesulfonic acid silica of Zeidan et al. With respect to (1.), said substitution would have been obvious because 10•SBA has a greater per site yield of bisphenol A compared to 11•SBA as well as a higher ratio of p,p′-bisphenol A (the preferred product) to o,p′-bisphenol A [see Table 3] while “[t]he ratio of p,p′-bisphenol A to o,p′-bisphenol A is much higher for the propylsulfonic acid modified SBA-15, 9•SBA, than the aryl sulfonic acid modified SBA-15, 11•SBA (10 vs 3)” [see last paragraph on right hand side of page 9410]. With respect to (2.), said addition would have been obvious because it has been held to be “prima facie obvious to combine two compositions each of which is taught by the prior art to be useful for the same purpose, in order to form a third composition to be used for the very same purpose.... [T]he idea of combining them flows logically from their having been individually taught in the prior art.” In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072. Consequently, the invention as a whole would have been prima facie obvious.
With respect to claim 10, in an embodiment where 9•SBA and/or 10•SBA is substituted for the ethylbenzenesulfonic acid silica of Zeidan et al, it is well known in the art to add thiols as a homogeneous feed additive; that is, chemically and physically separate from SBA.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. [1.] Hoshino et al (US 2010/0069677 A1), which discloses “SBA-15 type mesoporous silica was synthesized as follows using a triblock copolymer (Pluronic P123) as a structure-directing agent…4 g of Pluronic P123…was added to 30 g of water to be dispersed and, while stirring the dispersion, thereto were then added 120 g of 7 wt %-hydrochloric acid (an aqueous hydrogen chloride solution), 0.3 g of cobalt nitrate and 0.9 g of citric acid. Then, 8.5 g of tetraethoxysilane (ethyl orthosilicate…) was added and stirred at 60o C. for 41 hours, and then, the mixture was subjected to hydrothermal synthesis at 100o C. for 2 days. The obtained mixture was filtered and collected residue was washed with water and then dried at 60o C. overnight. The obtained dried product was calcined at 500o C. for 7 hours under air flow. When an analysis according to the above method was carried out on the powder obtained by calcination (SBA-15 type mesoporous silica)” [paragraph 0046]; [2.] Oliveira de Magalhães et al in “Production of Pure Granules of Sba-15 Mesoporous Silica” in Materials Research (2018, vol 21, no.6, 6 pp.), which discloses “[t]his study reports the production and characterization of clay-free granules of SBA-15 mesoporous silica, by applying the extrusion technique. The suggested methodology uses only methocel as the organic binder, which is removed after calcination. The granulation process was successfully achieved, producing pure granules of SBA15 mesoporous silica, in size of millimeters, with 8.3 MPa of compacting pressure (by axial crushing test). The surface area and pore volume of SBA-15 mesoporous silica granules (calcined at 800 ºC) were around 392 m2/g and 0.53 cm3/g, respectively” [abstract] and “[t]he SBA-15 extrudates were prepared by extrusion procedure, involving six main steps: powder mixing, paste preparation, extrusion, cutting, drying and calcination” [see first paragraph under the heading “2.3 Preparation of SBA-15 mesoporous silica extrudates]; [3.] Margelefsky et al in the Journal of the American Chemical Society (2008, 130, 13442-13449), which discloses “[t]hiols have been either added as a homogeneous feed additive or bound to the resin surface by ion-pairing. Several solid catalysts bearing both acid and thiol groups covalently attached to a solid support have been reported. Thiols have been covalently tethered to polymeric resins containing sulfonic acid groups, and polysiloxane catalysts containing randomly organized alkylsulfonic acid and alkylthiol groups have also been reported to have good catalytic” [see last paragraph on right hand side of page 13442].
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/BRIAN A MCCAIG/Primary Examiner, Art Unit 1772
5 January 2026