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 .
Patent Prosecution Highway
The decision dated 17 July 2025 granting the request and petition under 37 CFR 1.102(a) to accord the instant application “special” status is acknowledged.
Status of the Claims
Claims 1, 3, 7, and 10 are pending.
Claims 2, 4-6, 8, and 9 are cancelled.
Response to Amendments
Applicant’s amendments filed 30 September 2025 are acknowledged.
Claim Rejections - 35 USC § 112
Applicant’s amendment to claim 1 is sufficient to overcome the rejection of claims 1, 3, 7, and 10 under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Claim 1 has been amended to define R1, to define the pressure, and for clarity regarding the nitrogen-containing compound. The rejection is withdrawn.
Applicant’s amendment to claim 10 is sufficient to overcome the rejection of claim 10 under 35 U.S.C. 112(d) 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. Claim 10 has been amended to delete the temperature limitation and to further limit the reaction time within the range stated in claim 1. The rejection is withdrawn.
Claim Rejections - 35 USC § 103
Applicant’s amendment to claim 1 is sufficient to overcome the rejection of claims 1, 3, 7, and 10 under 35 U.S.C. 103 as being unpatentable over Gunnoe et al. (US20190062255, cited by applicant 17 August 2023, hereinafter Gunnoe), as evidenced by Sandgren et al. (US20160208412), in view of Vismans et al. (US20140066649, hereinafter Vismans). Due to the amendment to claim 1 the rejection is withdrawn and a new ground(s) of rejection is/are provided below.
Response to Arguments
Applicant’s arguments filed 30 September 2025 have been fully considered but they are not persuasive.
Applicant argues that Gunnoe, as evidenced by Sandgren, and Vismans do not disclose the limitations as recited in amended claim 1. These arguments have been considered but are not persuasive for the reasons set forth in the new grounds of rejection below and the response to arguments below.
In response to applicant’s argument on page 9 of the remarks filed on 30 September 2025 that the references fail to show certain features of the invention, it is noted that the features upon which applicant relies (i.e., inexpensive nitrogen oxide) are not recited in the rejected claim(s). Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims, see In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). The claims are drawn to the “nitrogen-containing compound catalyst is selected from the group consisting of nitric acid, nitrous acid, nitrates, nitrites, nitrogen oxides, and mixtures thereof”. The claims are not specifically drawn to an inexpensive nitrogen oxide. For the reasons indicated above, applicant’s above argument is not persuasive.
In response to applicant’s argument on pages 9-11 of the remarks filed on 30 September 2025 that “oxygen is excluded as a reactant in the reaction of Gunnoe”, “Gunnoe does not include alkanes and oxygen, and Gunnoe fails to teach on the step of “mixing a gaseous alkane with oxygen or air to obtain a mixed gas recited in the amended claim 1 of the present application”, and Gunnoe is not concerned with gas exchange. As stated on page 6 of the previous office action (OA), Gunnoe teaches “converting alkanes, such as methane, see Paras. [0040];[0058]-[0059], into esters, such as methyl trifluoroacetate, by the reaction of a mixed gas comprising methane, oxygen, and air, see Paras. [0058]-[0061]”. Specifically, Para. [0061] of Gunnoe teaches “the salt, the iodine-based compound, and the source of functionalization can be added (e.g., separately, mixed prior to introduction and then added, or simultaneously added) to a reaction vessel to form a first mixture and then the hydrocarbon can be added to the reaction vessel … the reaction vessel can be pressurized with a gas sufficient to provide an internal pressure … the gas used to obtain this pressure are methane, ethane, propane, butane, carbon dioxide, nitrogen, helium, argon, neon, carbon monoxide, hydrogen, oxygen, air, the hydrocarbon itself, or mixtures thereof … to accomplish flowing gas into and out of the vessel”. In addition, Paras. [0100];[0128] of Gunnoe state “[t]he reaction with ethane and oxygen were charged first with 255 kPa O2 then filled to a final pressure of 2070 kPa with ethane”, which specifically refers to a mixture of alkane and oxygen. Therefore, Gunnoe specifically teaches the step of “mixing a gaseous alkane with oxygen or air to obtain a mixed gas” and using pressure to control the gas exchange within the system. For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s argument on page 9 of the remarks filed on 30 September 2025 that Vismans objective and materials involved are different from Gunnoe and a person of skill in the art would not be motivated to combine the two, the test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981). Since both Gunnoe and Vismans teach the vapor phase catalytic production of esters from alkanes, a person of ordinary skill in the art has good reason to produce an ester by pursuing the known options within their technical grasp for the benefit of safely and efficiently producing an ester via oxidation of hydrocarbons in an acid environment that has a reduced/increased heat capacity that supports higher oxygen concentrations, see Vismans, Paras. [0011];[0016];[0019];[0024] and MPEP 2141. For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s argument on page 10 of the remarks filed on 30 September 2025 that Sandgren is non analogous art. Sandgren is not relied upon for the basis of any rejection. Sandgren is simply relied upon to provide evidence of room temperature, standard ambient temperature, and atmospheric pressure. For the reason indicated above, applicant’s above argument is moot.
In response to applicant’s argument on pages 10-11 of the remarks filed on 30 September 2025 that changing the sequence of adding ingredients “should not be considered as obvious try” and the “[e]xamples shown in the instant specification strictly adhere to this specific order, demonstrating that this order is crucial to the successful implementation of the present invention, and should not be interpreted as an arbitrary choice or obvious try”, the fact that the inventor has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious, see Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985). Base claim 1 of the instant application states “comprising …”. MPEP 2111.03 I. states “[t]he transitional term “comprising”, which is synonymous with “including,” “containing,” or “characterized by,” is inclusive or open-ended and does not exclude additional, unrecited elements or method steps” and MPEP 2144.04 IV.C. states “selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results”. Therefore, the instantly claim steps do not “exclude additional, unrecited elements or method steps” and the instant claims also do not exclude “selection of any order of performing [the] process steps”.
As instantly claimed, the steps of mixing, adding, conducting, followed by adding, conducting, followed by extraction, drying, filtration, distillation, and separation may be performed in any order that is obvious to a person of skill in the art and may have additional “unrecited elements or method steps” in between each step. It appears only one step in lines 4-6 of base claim 1, includes the limiting claim language of “in sequence” stating “followed by adding the mixed gas, and then an acid and a solvent in sequence to carry out a reaction”. Gunnoe Para. [0061] teaches “the salt, the iodine-based compound, and the source of functionalization can be added (e.g., separately, mixed prior to introduction and then added, or simultaneously added) to a reaction vessel to form a first mixture and then the hydrocarbon can be added to the reaction vessel” and Para. [0062] teaches “contact the hydrocarbon with the salt, the iodine-based compound, the source of functionalization and pressurization gas to generate a mixture including the functionalized hydrocarbon formed from the hydrocarbon and an adduct of the source of functionalization”. It would have been obvious for a person of ordinary skill in the art to rely upon Gunnoe before the effective filing date of the claimed invention for knowledge generally available within the art regarding rearranging the sequence of adding ingredients to obtain the desired mixture of reactants, concentration of reactants, product, and product yield, see MPEP 2144.04 VI.C. For the reasons indicated above, applicant’s above arguments are not persuasive.
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 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.
Claims 1, 3, 7, and 10 are rejected under 35 U.S.C. 103 as being unpatentable over Gunnoe et al. (US20190062255, hereinafter Gunnoe), as evidenced by Sandgren et al. (US20160208412), in view of Vismans et al. (US20140066649, hereinafter Vismans), Periana et al. (US5306855, patented 26 April 1994, hereinafter Periana) and Zhang et al. (CN102212086, published 12 October 2011, see machine translation, hereinafter Zhang).
Gunnoe teaches the claims 1, 3, 7, and 10 limitations of converting alkanes, such as methane, see Paras. [0040];[0058]-[0059], into esters, such as methyl trifluoroacetate, by the reaction of a mixed gas comprising methane, oxygen, and air, see Paras. [0058]-[0061], with a calcium and nitrogen containing catalysts, such as HCl, KCl, NH4Cl, and the nitrogen containing ammonium iodate, NH4IO3 or ammonium periodate, NH4IO4, see Paras. [0021];[0058]-[0059];[0068];[0072];[0098]; and Fig. 5.1. An aqueous trifluoroacetic acid is used as a source of functionalization which is supplied to the reactor separately, mixed prior to introduction and then added, or simultaneously added, i.e., the solvent is water and trifluoroacetic acid is the acid; or, water, trifluoracetic acid, and acetic acid are a mixture of individual solvents, see Paras. [0058]-[0061];[0073];[0121], meeting the mixed gas, the catalyst, the acid, the solvent, the specific R1-H hydrocarbon aka methane, where R1 is a methyl group and R2 is CF3, trifluoromethyl-COOH aka trifluoroacetic acid, the specific calcium compound, the specific acid solvent in claim 1;
The reaction is carried out at pressures ≤ 3500 kPa which includes a lower limit of zero, i.e., ambient/atmospheric pressure is 101.3 kPa or 1 atmosphere, and a temperature of about 25 to 300° C or ≤ 250° C which includes a lower limit of zero for 10 minutes to 5 days, i.e., room temperature is 25° C, in a vessel containing a light source which is a 500W compact fluorescent light bulb in an oxygen in air atmosphere, see Paras. [0059];[0061]-[0063];[0083];[0106];[0122], and the reaction is carried out without applying pressure, i.e., in ambient/atmospheric pressure, see Paras. [0103]-[0104]; as evidenced by Sandgren et al., Para. [0020], room temperature is 25° C and standard ambient temperature and atmospheric pressure is 25° C. and 1 atmosphere, meeting the light-transmission reaction vessel, specific light source, the reaction pressure, the reaction temperature, and the equation in claim 1 and meeting and within the ranges in claim 10;
After the reaction the esterified alkane product is separated and collected by separating the reactants by extraction, drying, diffusion through a membrane aka filtering under ambient conditions, see Paras. [0081];[0103]-[0104], then the yield is analyzed by nuclear magnetic resonance, NMR, and gas chromatography-mass spectrometry applying a fused silica PLOT column separating the ester, see Paras. [0087];[0121]-[0122], meeting the analysis, extraction, drying, filtration, distillation, and separation by column chromatography in claim 1; and,
0.676 mmol of KCl is used to convert 6.7 mmol of ethane to 2.03 mmol EtTFA, ethyl trifluoroacetate, as calculated by the examiner, a molar amount of KCl of 10.09% of that of ethane, see Para. [0098], and 7.70 mmol NH4IO3 is used to convert 8.4 mmol of methane to 1.81 mmol MeTFA, methyl trifluoroacetate, as calculated by the examiner, a molar amount of NH4IO3 91.67% of that of methane, see Para. [0110], meeting and within the range of the chlorine and nitrogen compounds in claim 7.
Gunnoe does not teach:
The claim 1 limitations of the sequence of adding ingredients to the reaction vessel, and the sequence of the steps of obtaining the product;
The claim 3 limitations; and,
The claim 7 limitation of a molar amount of the acid is 100% to 500% of the chlorine-containing compound catalyst and/or the nitrogen-containing compound catalyst.
Vismans relates to the vapor phase catalytic production of vinyl acetate by contacting acetic acid, oxygen, ethylene, water, and heat capacity modifiers, such as nitrogen, water, ethane, methane, and mixtures thereof at a reaction pressure of 0.1 MPa or 1 atmosphere, see Paras. [0019]-[0020];[0024];[0043];[0059]-[0060]. The volume of the reactor has oxygen present in an amount of from 1 mol % to 15 mol % oxygen, see Para. [0027], and methane/ethane present from 1 mol % to 50 mol % as heat capacity modifier(s), see Paras. [0024];[0026];[0042];[0060], meeting and within the volume ratio in claim 3. The acetic acid is present in an amount of from 1 mol % to 85 mol %, see Para. [0028], and nitrogen is present from 1 mol % to 50 mol % as heat capacity modifier(s), see Paras. [0024];[0026], meeting and within the range in claim 7.
Although Gunnoe does not teach the exact sequence of adding ingredients to the reaction vessel and the exact sequence of the steps of obtaining the product, it does not appear that the claim language or limitations result in a manipulative difference in the method steps when compared to the prior art disclosure. Since selection of any order of mixing ingredients is prima facie obvious, see MPEP 2144.04 C., and Gunnoe teaches ingredients may be mixed separately, later added, and simultaneously, where the steps can be executed in different sequence if logically possible, see Gunnoe, Paras. [0032];[0061]. On this record, it is reasonable to conclude that any sequence of reactant mixing order of Gunnoe would lead to the predictable result of functionalizing a hydrocarbon. The fact that applicant may have discovered yet another beneficial effect from the method set forth in the prior art by changing the sequence of adding ingredients does not mean that they are entitled to receive a patent on that method.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified Gunnoe to mix the reactants in any order, see MPEP 2144.04 C., and to vary the concentrations of the alkane, acid, nitrogen, and oxygen as taught by Vismans, with a reasonable predictability of success for the purpose of safely and efficiently producing an ester via oxidation of hydrocarbons in an acid environment that has a reduced/increased heat capacity that supports higher oxygen concentrations, see Vismans, Paras. [0011];[0016];[0019];[0024].
By applying “routine optimization” and “predictable results” to select the optimal reactant concentrations, one of ordinary skill in the art would have been motivated to make these modifications because Vismans provides a finite number of identified, predictable solutions. A person of ordinary skill in the art has good reason to produce an ester by oxidation of hydrocarbons in an acid environment by pursuing the known options within their technical grasp for the benefit of safely and efficiently producing an ester via oxidation of hydrocarbons in an acid environment that has a reduced/increased heat capacity that supports higher oxygen concentrations, see Vismans, Paras. [0011];[0016];[0019];[0024] and MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
In addition, “[t]he normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as the concentration of the reactants, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
Gunnoe does not teach the claim 1 limitations of the specific nitrogen compound.
Periana relates to a process for converting lower alkanes into their corresponding esters, see Abstract, through use of a catalytic process involving contacting methane with an organic or inorganic acid solvent, such as HNO3, CF3CO2H, and mixtures thereof, and an oxidizing agent, such as Cl2, I2, perchloric acid, hypochlorites, O2, 1/2O2, O3, NO2, SO3, H2SO4, and mixtures thereof, in the presence of a catalyst, such as Hg(NO3)2 and HgCl2, see Col. 3, Ln. 54-Col. 5, Ln. 46; Col. 7, Lns. 25-33 and Lns. 52-62, meeting the methane, specific acid, chlorinated metal salt, specific nitrogen containing compound, and solvent in claim 1.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified Gunnoe to use the nitrogen containing compounds as taught by Periana with a reasonable predictability of success for the purpose of efficiently using a nitrogen containing compound that functions as a reactant, an oxidant, and a solvent to form the oxy-ester with high conversion and selectivity, see Periana, Col. 3, Lns. 47-51; Col. 4, Lns. 65-68.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since both Gunnoe and Periana teach the reaction is conducted with methane, oxygen, trifluoroacetic acid, chlorine, iodine, and nitrogen reactants, a person of ordinary skill in the art has good reason to esterify an alkane by pursuing the known options within their technical grasp for the benefit of efficiently using a nitrogen containing compound that functions as a reactant, an oxidant, and a solvent to form the oxy-ester with high conversion and selectivity, see Periana, Col. 3, Lns. 47-51; Col. 4, Lns. 65-68 and MPEP 2141.
Selection of a known material, such as nitric acid, nitrates, nitrites, and nitrogen oxides, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied, 426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
Gunnoe does not teach the claim 1 limitation of conducting vacuumization for gas exchange.
Gunnoe teaches the reaction is conducted in a mixed gas environment of methane, ethane, propane, butane, nitrogen, oxygen, and/or air in a pressurized vessel having a pressure system that includes “pumps, valves, metering gauges, computer system, and the like to accomplish flowing gas into and out of the vessel”, see Para. [0061].
Zhang is in the field of catalytically converting hydrocarbons in a mixed gas and nitrogen environment, see Abstract; Paras. [0032];[0036];[0040];[0044]. Zhang solves the problem of gas flow and gas exchange by using a vacuum, see Paras. [0036];[0040];[0044] and MPEP 2143 B & G, meeting the vacuum gas exchange in claim 1.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified Gunnoe to use a degassing or vacuum exchange to mix the gases as taught by Zhang with a reasonable predictability of success for the purpose of mixing and replacing the gases in order to ensure appropriate contact time amongst the reactants and a high product yield, see Zhang, Abstract; Paras. [0024];[0036];[0040];[0044].
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since both Gunnoe and Zhang teach the reaction is conducted under a nitrogen and mixed gas environment with pressure control, a person of ordinary skill in the art has good reason to conduct a mixed gas reaction with vacuum degassing and mixing by pursuing the known options within their technical grasp for the benefit of mixing and replacing the gases in order to ensure appropriate contact time amongst the reactants and a high product yield, see Zhang, Abstract; Paras. [0024];[0036];[0040];[0044] and MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied, 426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Y. Lynnette Kelly-O'Neill whose telephone number is (571)270-3456. The examiner can normally be reached Monday-Thursday, 8 a.m. - 6 p.m., EST, with Flex Time.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Yen-Ye Goon can be reached at (571) 270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/YO/Examiner, Art Unit 1692
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691