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 .
Claim Status
Claims 1-48 were filed on 3/10/2023. In a preliminary amendment filed on the same day, claims 1, 5-10, 14, 15, 17, 19, 20, 25, 29-34, 38, 39, 41, 43 and 44 were amended, claim 49 was newly added, and claims 2-4, 11-13, 16, 18, 21-24, 26-28, 35-37, 40, 42, and 45-48 were canceled. Claims 1, 5-10, 14, 15, 17, 19, 20, 25, 29-34, 38, 39, 41, 43, 44, and 49 are pending.
Priority
The instant application was filed on 3/10/2023 and claims the benefit of priority to the following applications:
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See filing receipt dated 5/29/2024.
Claim Objections
Claims 7, 14, 17, 20, 38, 41, and 44 are objected to because of the following informalities:
Claim 7 is objected to because it is missing a period at the end of the claim. See MPEP 608.01(m).
Line 3 of claims 14 and 38 are objected because there is a word missing between the limitations “group” and “Nb2O5”. For example, --of--. Appropriate correction is required.
Line 4 of claims 14 and 38 is objected to because there is a comma missing to separate the limitation “ZrWxOy” and the limitation “V2O5”.
Line 4 of claims 14 and 38 recite the following: “ZrWxOy (wherein x is 2 and y is 0.5 to 8)”. The “wherein” limitation should be taken out of parentheticals.
Lines 1-2 of claims 17 and 41 recite “wherein the acidic material is…”. The limitation “acidic material” should be deleted and replaced by –heterogenous catalyst”. The options in the Markush describe the full acidified transition metal catalyst and not the acidic material as defined in claims 15 and 39.
Lines 2-3 of claim 20 recite “the catalyst is an amphoteric material exhibiting basic sites includes any or combination of …”. The limitation should be amended to recite –the catalyst is an amphoteric material exhibiting basic sites, including any one or combination of …--.
Line 3 of claims 20 and 44 recite “Fe2O3, Cr2O3,”. The word –and—should be inserted between these limitations to close the Markush group defining the amphoteric material exhibiting basic sites.
Claim Rejections - 35 USC § 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 15, 25, 29-34, 38, 39, 41, 43, 44, and 49 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Lines 3-4 of claims 15 and 39 recite “with a transition metal selected from the group consisting of Fe, Ti, Zr, Hf, Sn and Si an Al and combinations thereof”. The limitation contains at least one spelling error (“an” in line 4 should presumably be –and--). However, even assuming that the word “an” is –and—, the scope of the Markush group is unclear. “Si” and “Al” correspond to silicon and aluminum, which are not transition metals; and because of the spelling error above and the use of three “and” limitations in a row it is not clear what the Markush group for the transition metal includes. Traditional Markush language uses the phrase “selected from the group consisting of A, B, and C”, which clearly elucidates what the alternatives are. The present claim language does not. Does it only include Fe, Ti, Zr, Hf, and Sn? Or does it also include “Si and Al”? If so, are those a single option (Si and Al) or can either option be used alone (Si or Al)? Alternatively, are Si and Al alternatives to the transition metals (Fe, Ti, Zr, Hf, Sn) for the heterogeneous catalyst and therefore, not considered to be transition metal oxides? If so, are those a single option (Si and Al) or can either option be used alone (Si or Al)? If the “metal oxide” is limited to “Si” or “Al” oxides, then must these also be treated with the acidic material? According to claims 17 and 41, silicon oxides and aluminum oxides can be used alone as the “transition metal oxide” which is treated with acidic material. However, this is not clear from the present claim language of claims 15 and 39.
In claim 25, the final paragraph recites:
optionally withdrawing a proportion of the unreacted formic acid, unreacted oxidizing agent and reaction byproducts from a reboiler located at the bottom of the stripping section, and [[withdrawing some or all of the performic acid enriched product from a condenser located at the top of the rectification section to create a performic acid rich distillate product stream, for point of use application,]] optionally cooling the performic acid product and optionally storing the performic acid product (annotations added for discussion).
While it is clear that the first withdrawing step, the cooling, and the storing steps (all underlined) are optional, is it not clear if the second withdrawing step in brackets [[]] is also optional. None of the claims that depend from claim 25 cure this deficiency, therefore, they are also rejected for depending from an indefinite claim and failing to cure the deficiency.
Claim 44 recites “the amphoteric material exhibiting basic sites includes any one or combination of …. or is a basic anion exchange resin”. It is not clear how a basic anion exchange resin can be amphoteric. As evidenced by Sensorex (downloaded from https://sensorex.com/ion-exchange-and-industrial-applications/?srsltid=AfmBOoogermx3kgkF2RKTiJbg1N666cKNx-cw_ObpSfLEVLJjo_lvVzh
On 1/22/2026), anionic exchange resins are basic and distinct from amphoteric resins. See “Cation, Anion, and Amphoteric Exchanges” section on p. 7-8 of the printout.
Claim Rejections - 35 USC § 112(d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 17 and 41 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Line 4 in claims 17 and 41 recite the option “B2O3/ZrO2”. This does not further limit claims 15 and 39, from which claims 17 and 41 respectively depend. The final line in claims 15 and 39 requires the acidic material to be a sulphate (SO4), tungstate (WO3) or molybdate (MoO3). The limitation above corresponds to boron trioxide.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
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.
Claim(s) 1, 5-8, and 10 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhou (CN 105646435A, published on 6/8/2016, of record in the IDS filed on 3/13/2023; a machine generated English translation is also provided with the instant OA) in view of Ebrahimi (“Heterogeneously catalyzed synthesis of performic acid in a microstructure reactor” Chemical Engineering Journal, 179, 2002, p. 312-317, of record in the IDS filed on 3/13/2023).
The instant claims are directed toward a catalytic distillation process for the production of performic (peroxyformic, HC(O)O-OH) acid comprising:
Feeding separate aqueous solutions of formic acid (HC(O)OH) and an oxidizing agent, under controlled flow rates, into a catalytic distillation column above one or more reaction zones located generally in the middle of the column, said one or more reaction zones including one or more immobilized heterogeneous catalysts;
Said column being operated at sub-atmospheric pressure (a vacuum) and pre-selected temperature such that the oxidizing agent and formic acid are introduced into the reaction zones and undergo reaction to produce performic acid and reaction by-products;
Wherein a performic acid enriched liquid product containing some unreacted oxidizing agent flows downwards into a stripping section located below the one or more reaction zones and wherein a vapour phase containing unreacted formic acid, some unreacted oxidizing agent and reaction by-products rise up through a rectification section located above the one or more reaction zones; and
Withdrawing the vapor phase containing unreacted formic acid, some unreacted oxidizing agent and reaction by-products from a condenser located at the top of the rectification section and returning some of all of the condensed distillate back to the column as reflux and withdrawing the performic acid enriched liquid product from the bottom of the stripping section to create a performic acid rich bottoms product stream.
Zhou teaches a process and apparatus for producing epsilon-caprolactone from anhydrous peroxy isobutyric acid, wherein the peroxy isobutyric acid is produced in situ from the reaction of iso-butyric acid (a C3 saturated carboxylic acid) and hydrogen peroxide (H2O2, an oxidizing agent, claim 8) in catalytic reaction rectifying column (a catalytic distillation column). See abstract. Zhou teaches that the process is carried out in the following apparatus of Fig. 1:
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. Element (A1) corresponds to the catalytic rectification/distillation column which is equipped with a heterogeneous strong acid cation exchange resin catalyst (claim 10) and a filler/packing on top and bottom such that the catalyst is immobilized in a reaction zone which is generally in the middle of the column. Preferably the strongly acidic cation exchange resin is a sulfonic acid and/or a perfluorosulfonic acid resin. See claim 8. A stream of aqueous hydrogen peroxide (1) and a stream of carboxylic acid and an organic solvent (2) are separately fed to the catalytic distillation column above the reaction zone. The column further contains a rectification section at the top of the column and a stripping section at the bottom of the column. Organic solvent, unreacted starting materials and water are removed as a vapor from the top of the column, wherein the water and organic solvent form an azeotrope to facilitate removal of the water. The vapor is condensed using a condenser and fed to water separation reflux tank (V1), wherein the organic phase is refluxed back to the reactor and the aqueous phase (3) is withdrawn from the bottom of the tank (VI). The peroxycarboxylic acid product, along with some unreacted starting materials, by-products, and water are fed to the stripping section at the bottom of column (A1) to obtain an anhydrous stream of the peroxycarboxylic acid (4) which is sent downstream for further processing into epsilon-caprolactone. See Figure, and lines 126-251 of the translation of the specification of Zhou.
Zhou teaches that the catalytic distillation column is operated at a preselected temperature in the range of 30-70°C and a pressure in the range of 2 to 8 kPa (approx. 0.02 to 0.08 atm). See claim 2. Thus, the catalytic distillation of Zhou is operated at sub-atmospheric pressure (< 1 atm) and the temperature range of Zhou falls within or overlaps with all of the claimed ranges in claims 5-7. Zhou also teaches that the entire process is run continuously and defines the molar ratio of hydrogen peroxide to isobutyric acid. See claims 1 and 6. Therefore, it is obvious that the carboxylic acid and oxidizing agent are being added at controlled flow rates which correspond to the desired reaction stoichiometry in the continuous process.
Zhou does not explicitly teach the use of an aqueous solution of formic acid to produce performic acid when contacted with hydrogen peroxide.
Ebrahimi is directed toward a heterogeneous cation exchange resin catalyzed synthesis of performic acid in a microstructured reactor. See abstract. Ebrahimi teaches that performic acid, though unstable, is an efficient oxidizer which has found many uses in the chemical industry for disinfection and bleaching purposes. Ebrahimi teaches that the cation exchange resins explored in the paper, Dowex® 50Wx8 and Dowex® 50Wx2, are strongly acidic cation exchange resins (claim 10). Ebrahimi teaches that the same types of catalysts (heterogenous strong acids) can generally facilitate the reactions between other carboxylic acids and oxidants to produce peroxycarboxylic acids. See introduction section on p. 312. Ebrahimi teaches that strongly acidic cation exchange resins catalyze the reaction between formic acid (HCOOH) and hydrogen peroxide (H2O2, oxidizing agent) to produce water (H2O) and performic acid (HCOOOH) in the same reaction as set forth in claim 8.
Ebrahimi teaches that the formic acid and hydrogen peroxide are introduced into the reaction system as separate aqueous streams. Ebrahimi also teaches that the flow rates of the two streams is adjustable in the continuous reaction. Ebrahimi teaches the reaction is carried out at atmospheric pressure and at a temperature in the range of 283-313 K (about 10-40°C), which falls within or overlaps with all of the ranges of claims 5-7. See Fig. 3 on p. 314 and sections 2.2 and 2.3 on p. 313-314.
It would have been prima facie obvious to combine the teachings of Zhou and Ebrahimi to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated carry out the oxidation of formic acid with hydrogen peroxide in a catalytic distillation reactor because Ebrahimi teaches the value of producing performic acid, and that it can be carried out under the same conditions as Zhou (catalyst and temperature) in the presence of water. Therefore, substituting one know reaction apparatus for another is prima facie obvious. Further, the apparatus of Zhou can also provide a purified, dried product directly from the bottom of the reaction column, thus simplifying the reaction process by combining reaction and purification steps. Also see MPEP 2143(I)(B).
Claim(s) 9, 14, 15, 17, and 19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhou (CN 105646435A, published on 6/8/2016, of record in the IDS filed on 3/13/2023; a machine generated English translation is also provided with the instant OA) in view of Ebrahimi (“Heterogeneously catalyzed synthesis of performic acid in a microstructure reactor” Chemical Engineering Journal, 179, 2002, p. 312-317, of record in the IDS filed on 3/13/2023), as applied to claims 1, 5-8, and 10 above, and further in view of McSherry (US 2008/0275132, published 11/6/2008), as evidenced by Krause (“Acidic and basic surface sites of zirconia-based biomass gasification gas clean-up catalysts” Applied Catalysis A: General 362, 2009, p. 169-177).
The instant claims are directed toward the use of a compound/source that can be used to generate oxidizing agent hydrogen peroxide in situ and the use of metal oxides as the heterogeneous catalyst. Zhou and Ebrahimi only contemplate the use of an aqueous solution of hydrogen peroxide in the presence of cation exchange resin catalysts.
McSherry is directed toward an apparatus and method for making a peroxycarboxylic acid in the presence of a heterogeneous catalyst. See abstract and [0066]. McSherry teaches that the heterogeneous catalysts catalyze the reaction of hydrogen peroxide or a hydrogen peroxide donor (a source/compound which provides hydrogen peroxide in situ, as required by claim 9) with a short chain carboxylic acid to produce the corresponding peroxycarboxylic acid in the presence of water. See [0003-0007 and 0086-0093] and [0054, 0110-0111]. McSherry teaches that the short chain acids include formic acid, which will produce performic acid. See [0021, 0271, and 0278]. McSherry teaches that a wide variety of heterogeneous acids can be used as the catalyst, including ZrO2 (claim 14) and sulfated (SO4) or tungstated (WO3) zirconia (ZrO2) (claims 15 and 17). See [0106-0107]. As evidenced by Krause, ZrO2 is amphoteric and exhibits basic sites (claim 19). See section 3.2 (all subsections) on p. 172-174 of Krause.
It would have been prima facie obvious to combine the teachings of Zhou, Ebrahimi, and McSherry to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated employ an in situ generated hydrogen peroxide source because McSherry teaches that compounds are known for this purpose and can be used as alternatives to hydrogen peroxide in the combined process of Zhou and Ebrahimi. A person of ordinary skill in the art would have been motivated to substitute the strong acid cation exchange resins of the combined process of Zhou and Ebrahimi with one of the claimed catalysts because McSherry teaches that strongly acidic cation exchange resins can be predictably substituted for other types of solid acid catalysts, including the claimed metal oxides and acidified versions thereof. Also see MPEP 2143(I)(B).
Claim(s) 20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhou (CN 105646435A, published on 6/8/2016, of record in the IDS filed on 3/13/2023; a machine generated English translation is also provided with the instant OA) in view of Ebrahimi (“Heterogeneously catalyzed synthesis of performic acid in a microstructure reactor” Chemical Engineering Journal, 179, 2002, p. 312-317, of record in the IDS filed on 3/13/2023), as applied to claims 1, 5-8, and 10 above, and further in view of Matsuda (EP 0974581A1, published on 1/26/2000).
Claim 20 is directed toward the use of one of the claimed amphoteric materials which are exhibiting basic sites or a basic anion exchange resin as the catalyst. Zhou and Ebrahimi only contemplate the use of cation exchange resin catalysts.
Matsuda is directed toward a process for preparing equilibrium peroxy acid which is then used to produce a lactone. Matsuda teaches that carboxylic acids, including formic acid, are reacted with hydrogen peroxide in water in a reaction distillation apparatus containing a catalyst to produce the peroxyacid while continuously removing water. See abstract and claims. Matsuda teaches that the catalysts for the reaction can comprise basic and acid ion exchange resins. See [0024].
It would have been prima facie obvious to combine the teachings of Zhou, Ebrahimi, and Matsuda to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill in the art would have been motivated to substitute the strong acid cation exchange resins of the combined process of Zhou and Ebrahimi with one of the claimed catalysts because Matsuda teaches that both acidic cationic and basic anionic exchange resins can predictably be used as a catalyst for the combined process of Zhou and Ebrahimi. Therefore, Matsuda teaches that the catalyst of the combined process of Zhou and Ebrahimi can be substituted for basic anionic exchange resins with a reasonable expectation of success. Also see MPEP 2143(I)(B).
Claim(s) 25, 29-32, 34, and 49 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhou (CN 105646435A, published on 6/8/2016, of record in the IDS filed on 3/13/2023; a machine generated English translation is also provided with the instant OA) in view of Ebrahimi (“Heterogeneously catalyzed synthesis of performic acid in a microstructure reactor” Chemical Engineering Journal, 179, 2002, p. 312-317, of record in the IDS filed on 3/13/2023), as applied to claims 1, 5-8, and 10 above, and further in view of Boiling (https://www.chem.purdue.edu/gchelp/liquids/boil.html , as captured on 9/14/2001, downloaded from https://web.archive.org/web/20010914160144/https://www.chem.purdue.edu/gchelp/liquids/boil.html on 1/22/2026) and Horsley (“Table of Azeotropes and Nonazeotropes, 1947, p. 508 and 516-517).
Claim 25 is directed to a process of claim 1, wherein the performic acid is obtained as a vapor from the top of the rectification section and the unreacted products and by-products stream is obtained as a bottoms product from the stripping section of the column. In other words, the composition of the vapor from the top of the column and the composition of the liquid at the bottom column are reversed as compared to claim 1.
The combination of Zhou and Ebrahimi teach that the performic acid is obtained as an anhydrous product from the bottom of the column and that a top stream containing an azeotrope of water and organic solvent is obtained from the top of the column and, after separation of water from the condensed top stream, the organic solvent is refluxed back to the column. Zhou further teaches that the organic solvent (ethyl butyrate, methyl pivalate, or ethyl pivalate) forms an azeotrope with water and acts as an entrainer to efficiently remove all water from the reaction column. See claim 1 and lines 49-69 of the translation of the specification.
Neither Zhou nor Ebrahimi suggest that the distillation can be altered such that performic acid is obtained from the top of the column as a gas and obtaining unreacted reactants and byproducts from the bottom of the column.
Boiling is a generic reference to teach that the boiling point of liquids is affected by pressure. See all. At atmospheric pressure (1 atm), the liquid boils at a normal boiling point. When the external pressure is sub-atmospheric (<1 atm), the boiling point of the liquid is lower than its normal boiling point and when the pressure is above atmospheric (>1 atm), the boiling point of the liquid is greater than its normal boiling point. Thus, the reference establishes that it is known that the boiling points of liquids change with pressure, and that as the pressure decreases so does the boiling point of the liquid.
Horsley is a reference material for known azeotropes. See p. 508. Horsley is used to teach that formic acid, a reactant in the combined process of Zhou and Ebrahim, forms a plethora of known binary azeotropes with common organic solvents. The table of Horsley further teaches that azeotropes can affect the boiling point of the mixture of liquids. The normal boiling point of formic acid is 100.7°C, but can form both minimum azeotropes (those with lower boiling points than the normal boiling point) and maximum azeotropes (those with higher boiling points than the normal boiling point), depending upon the identity of the solvent. See p. 516-517.
It would have been prima facie obvious to combine the teachings of Zhou, Ebrahimi, Boiling, and Horsley to arrive at the instantly claimed process with a reasonable expectation of success. A person of ordinary skill would have been motivated to modify the pressure of the distillation because Zhou teaches that it can predictably proceed over a range of sub-atmospheric pressures. Further, Zhou does not explicitly exemplify formic acid in the system. Therefore, the exact distillation conditions for obtaining performic acid as a bottoms product are not known. However, what is known is how to affect the boiling point of the mixture and components thereof by forming (or preventing) azeotropes and/or modifying the pressure of the distillation. The skilled artisan could optimize one or both of these variables to arrive at the instantly claimed process with a reasonable expectation of success using predictable and well-known techniques.
Regarding claims 29-32, see above discussion regarding claims 5-8.
Regarding claim 34, see discussion regarding claim 10 above.
Further regarding claim 49, the combined process of Zhao and Ebrahim teaches that the distillation comprises a reflux. Therefore, if the distillation were modified to obtain performic acid as a distillate (top) product performic acid would be contained in the reflux.
Claim(s) 33, 38, 39, 41, and 43 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhou (CN 105646435A, published on 6/8/2016, of record in the IDS filed on 3/13/2023; a machine generated English translation is also provided with the instant OA) in view of Ebrahimi (“Heterogeneously catalyzed synthesis of performic acid in a microstructure reactor” Chemical Engineering Journal, 179, 2002, p. 312-317, of record in the IDS filed on 3/13/2023), as applied to claims 1, 5-8, and 10 above, and further in view of Boiling (full citation above) and Horsley (“Table of Azeotropes and Nonazeotropes, 1947, p. 508 and 516-517), as applied to claims 25, 29-32, 34, and 49 and further in view of McSherry (US 2008/0275132, published 11/6/2008), as evidenced by Krause (“Acidic and basic surface sites of zirconia-based biomass gasification gas clean-up catalysts” Applied Catalysis A: General 362, 2009, p. 169-177).
The instant claims are directed toward the use of a compound/source that can be used to generate oxidizing agent hydrogen peroxide in situ and the use of metal oxides as the heterogeneous catalyst. Zhou and Ebrahimi only contemplate the use of an aqueous solution of hydrogen peroxide in the presence of cation exchange resin catalysts. Boiling and Horsley are silent regarding these limitations.
McSherry is directed toward an apparatus and method for making a peroxycarboxylic acid in the presence of a heterogeneous catalyst. See abstract and [0066]. McSherry teaches that the heterogeneous catalysts catalyze the reaction of hydrogen peroxide or a hydrogen peroxide donor (a source/compound which provides hydrogen peroxide in situ, as required by claim 33) with a short chain carboxylic acid to produce the corresponding peroxycarboxylic acid in the presence of water. See [0003-0007 and 0086-0093] and [0054, 0110-0111]. McSherry teaches that the short chain acids include formic acid, which will produce performic acid. See [0021, 0271, and 0278). McSherry teaches that a wide variety of heterogeneous acids can be used as the catalyst, including ZrO2 (claim 38) and sulfated (SO4) or tungstated (WO3) zirconia (ZrO2) (claims 39 and 41). See [0106-0107]. As evidenced by Krause, ZrO2 is amphoteric and exhibits basic sites (claim 43). See section 3.2 (all subsections) on p. 172-174 of Krause.
It would have been prima facie obvious to combine the teachings of Zhou, Ebrahimi, Boiling, Horsley, and McSherry to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated employ an in situ generated hydrogen peroxide source because McSherry teaches that compounds are known for this purpose and can be used as alternatives to hydrogen peroxide in the combined process of Zhou, Ebrahimi, Boiling, and Horsley. A person of ordinary skill in the art would have been motivated to substitute the strong acid cation exchange resins of the combined process of Zhou, Ebrahimi, Boiling, and Horsley with one of the claimed catalysts because McSherry teaches that strongly acidic cation exchange resins can be predictably substituted for other types of solid acid catalysts, including the claimed metal oxides and acidified versions thereof. Also see MPEP 2143(I)(B).
Claim(s) 44 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhou (CN 105646435A, published on 6/8/2016, of record in the IDS filed on 3/13/2023; a machine generated English translation is also provided with the instant OA) in view of Ebrahimi (“Heterogeneously catalyzed synthesis of performic acid in a microstructure reactor” Chemical Engineering Journal, 179, 2002, p. 312-317, of record in the IDS filed on 3/13/2023), as applied to claims 1, 5-8, and 10 above, and further in view of Boiling (full citation above) and Horsley (“Table of Azeotropes and Nonazeotropes, 1947, p. 508 and 516-517), as applied to claims 25, 29-32, 34, and 49 and further in view of Matsuda (EP 0974581A1, published on 1/26/2000).
Claim 44 is directed toward the use of one of the claimed amphoteric materials which are exhibiting basic sites or a basic anion exchange resin as the catalyst. Zhou and Ebrahimi only contemplate the use of cation exchange resin catalysts. Boiling and Horsley are silent regarding the limitation.
Matsuda is directed toward a process for preparing equilibrium peroxy acid which is then used to produce a lactone. Matsuda teaches that carboxylic acids, including formic acid, are reacted with hydrogen peroxide in water in a reaction distillation apparatus containing a catalyst to produce the peroxyacid while continuously removing water. See abstract and claims. Matsuda teaches that the catalysts for the reaction can comprise basic and acid ion exchange resins. See [0024].
It would have been prima facie obvious to combine the teachings of Zhou, Ebrahimi, Boiling, Horsley and Matsuda to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill in the art would have been motivated to substitute the strong acid cation exchange resins of the combined process of Zhou, Ebrahimi, Boiling, and Horsley with one of the claimed catalysts because Matsuda teaches that both acidic cationic and basic anionic exchange resins can predictably be used as a catalyst for the combined process of Zhou, Ebrahimi, Boiling, and Horsley. Therefore, Matsuda teaches that the catalyst of the combined process of Zhou, Ebrahimi, Boiling, and Horsley can be substituted for basic anionic exchange resins with a reasonable expectation of success. Also see MPEP 2143(I)(B).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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/AMY C BONAPARTE/Primary Examiner, Art Unit 1692