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 of group I, claims 1-4 and 11 in the reply filed on 02/26/2026 is acknowledged. Claims 5-10 and 12-14 are withdrawn. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
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) as being anticipated by Zhao et al. (App. Cat. A. General 2020, 594, 117470).
Regarding claim 1, Zhao teaches an ionic liquid supported Ti-SBA-15 catalyst where Ti-SBA-15 is a titanium and silicon containing molecular sieve and the ionic liquid 3-methyl-1-(3-sulfonic acid) imidazolium zinc sulfate ([MIMPS]+(1/2Zn2+)SO42−)], which is a Bronsted-Lewis acidic ionic liquid (Title; Abstract; Pg. 1-2, Introduction; Scheme 1). Zhao teaches the ionic liquid is supported on the Ti-SBA-15 carrier, equivalent to the limitation “an acidic ionic liquid bonded to the titanium-silicon molecular sieve.”
Regarding claim 2, Zhao anticipates the product of claim 1 and Zhao further teaches the ionic liquid is 3-methyl-1-(3-sulfonic acid) imidazolium zinc sulfate [MIMPS]+(1/2Zn2+)SO42−)], which is a Bronsted-Lewis acidic ionic liquid containing a sulfonic (SO3) group (Title; Abstract; Pg. 1-2, Introduction; Scheme 1).
[AltContent: textbox (Figure 1. Reproduced Scheme 1 of Zhao, lower right, showing the sulfonic acid containing ionic liquid.)]
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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.
Claims 3 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Zhao et al. (App. Cat. A. General 2020, 594, 117470) in view of Wang et al. (CN105879907A English), with evidentiary supported by Morais et al. (New. J. Chem. 2018, 42, 10774).
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[AltContent: textbox (Figure 2. Reproduced Fig. 3 of Morais showing the structure of [HSO3-pmim])] Regarding claim 3, Zhao anticipates the product of claim 1 and Zhao further teaches the acidic ionic liquid cation is 3-methyl-1-(3-sulfonic acid) imidazolium (abbreviated [MIMPS] in Zhao), which is known by skilled artisans to be equivalent to [HSO3-pmim]. For example, evidentiary reference Morais depicts [HSO3-pmim] in Fig. 3, which when compared to 3-methyl-1-(3-sulfonic acid) imidazolium (i.e. [MIMPS]) in Zhao, these cations are clearly identical.
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[AltContent: textbox (Figure 3. Reproduced Scheme 1 of Zhao, lower right, showing the sulfonic acid containing ionic liquid.)]
The claim further requires the anion in the acidic ionic liquid is H2PO4, to which Zhao is silent.
Wang teaches an immobilized ionic-liquid catalyst where the ionic liquids contains sulfate (SO4), dihydrogen phosphate (H2PO4), or trifluoroacetate (C2F3O2) anions and are supported on silicon-containing supports (Abstract; Claims 1-2, Pg. 2, par. 7-10).
Advantageously, the immobilized ionic liquids of Wang allow for simple separation and regeneration (following catalysis) while being low corrosion and low cost (Pg. 2, par. 3).
It is noted Wang teaches three anions for the ionic liquid and does not explicitly use solely H2PO4, however, a skilled artisan would recognize the equivalence of these anions in the art and could routinely select any of the anion options of Wang when using the 3-methyl-1-(3-sulfonic acid) imidazolium ([MIMPS], i.e. HSO3-pmim) cation taught by Zhao. Wang teaches the ionic liquid prepared with any of the anions (SO4, H2PO4, C2F3O2) display the advantageous effects of providing a catalyst that is simple to separate and regenerate, while being low in corrosion and cost, and therefore a person of ordinary skill in the art would have recognized the interchangeability of the anion in the prior art Wang for the corresponding element disclosed in the claims. See MPEP 2144.06.II.
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 utilize a dihydrogen phosphate (H2PO4) anion with the 3-methyl-1-(3-sulfonic acid) imidazolium ([MIMPS], i.e. HSO3-pmim) cation in the product of Zhao in order to provide a catalyst that is simple to separate and regenerate, while being low in corrosion and cost, as taught by Wang.
Regarding claim 11, Zhao anticipates the product of claim 1 and 2 and Zhao further teaches the acidic ionic liquid cation is 3-methyl-1-(3-sulfonic acid) imidazolium (abbreviated [MIMPS] in Zhao), which is known by skilled artisans to be equivalent to [HSO3-pmim]. For example, evidentiary reference Morais depicts [HSO3-pmim] in Fig. 3, which when compared to 3-methyl-1-(3-sulfonic acid) imidazolium (i.e. [MIMPS]) in Zhao, these cations are clearly identical.
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[AltContent: textbox (Figure 4. Reproduced Scheme 1 of Zhao, lower right, showing the sulfonic acid containing ionic liquid.)]
The claim further requires the anion in the acidic ionic liquid is H2PO4, to which Zhao is silent.
Wang teaches an immobilized ionic-liquid catalyst where the ionic liquids contain sulfate (SO4), dihydrogen phosphate (H2PO4), and trifluoroacetate (C2F3O2) anions and are supported on silicon-containing supports (Abstract; Claims 1-2, Pg. 2, par. 7-10).
Advantageously, the immobilized ionic liquids of Wang allow for simple separation and regeneration (following catalysis) while being low corrosion and low cost (Pg. 2, par. 3).
It is noted Wang teaches three anions for the ionic liquid and does not explicitly use solely H2PO4, however, a skilled artisan would recognize the equivalence of these anions in the art and could routinely select any of the anion options of Wang when using the 3-methyl-1-(3-sulfonic acid) imidazolium ([MIMPS], i.e. HSO3-pmim) cation taught by Zhao. Wang teaches the ionic liquid prepared with any of the anions (i.e. SO4, H2PO4, C2F3O2) display the advantageous effects of providing a catalyst that is simple to separate and regenerate, while being low in corrosion and cost, and therefore a person of ordinary skill in the art would have recognized the interchangeability of the anion in the prior art Wang for the corresponding element disclosed in the claim. See MPEP 2144.06.II.
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 utilize a dihydrogen phosphate (H2PO4) anion with the 3-methyl-1-(3-sulfonic acid) imidazolium ([MIMPS], i.e. HSO3-pmim) cation in the product of Zhao in order to provide a catalyst that is simple to separate and regenerate, while being low in corrosion and cost, as taught by Wang.
Claim 4 is rejected under 35 U.S.C. 103 as being unpatentable over Zhao et al. (App. Cat. A. General 2020, 594, 117470) in view of Csendes et al. (Eur. J. Inorg. Chem. 2019, 3503-3510).
Regarding claim 4, Zhao anticipates the product of claim 1 and the claim further requires “the acidic ionic liquid accounts for 20% to 30% by mass of the ionic liquid-immobilized titanium-silicon molecular sieve catalyst.” Zhao teaches at example containing about 17% ionic liquid by weight percent (Fig. 4; Pg. 5, right col.) however does not disclose the weight percent of the other samples prepared.
Csendes teaches a supported ionic liquid Fe catalyst supported on silica (Title; Abstract; Pg. 3504, right col.). Csendes teaches the catalyst contains supported ionic liquids with concentrations ranging from 10 to 40 wt.% (Pg. 3506, left and right col.).
Advantageously, increasing the ionic liquid concentration continuously decreases the pore volume of the catalyst due to filling of the pores, where catalysts containing up to 40% continue to operate (Pg. 3506, right col.; Fig. 5; Table 2).
It is noted Csendes teaches an Fe-based ionic liquid-supported catalyst on silica while the claims are directed to a titanium-silicon molecular sieve based catalyst. However, the teachings of Csendes are considered to be relevant prior art because the disclosure is in the field of ionic liquid supported catalysts, where the support contains silica, and because the teaching of increased loading of ionic liquid past 40% being detrimental to pore volume (due to filling) is considered general and motivating to all skilled artisans in this field.
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 between 10 to 40 wt.% of ionic liquid in the ionic liquid-supported catalyst of Zhao in order to provide a catalyst that includes ionic liquid but also retains pore volume for performing catalysis, as taught by Csendes.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Hu et al. (ChemistrySelect 2018, 3, 5087-5091); Hu teaches a titanium incorporated mesoporous silica immobilized functional ionic liquid (Title). Cruz et al. (RSC Adv. 2016, 6, 19723-19733); Cruz teaches a titanium immobilized on silica-imidazolium based ionic liquids (Title; Abstract).
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/JORDAN W TAYLOR/Examiner, Art Unit 1738