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 1-20 were filed 07/14/2023. No preliminary amendments of the claims were submitted.
Claims 1-20 are currently pending and under examination.
Priority
The instant application claims domestic benefit to U.S. provisional application no. 63/390,045 filed on 07/18/2022. Applicant’s claim for benefit of a prior-filed application under 35 U.S.C. 119(e) is acknowledged.
Claim Objections
Claim 3 is objected to because of the following informalities: Instant claim 3 contains a misspelling of the word “amount”. Applicant is advised to correct the misspelling. Appropriate correction is required.
Claim Rejections - 35 USC § 112
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.
Claim 1 is 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.
The term “low concentration” in claim 1 is a relative term that is subjective which renders the claim indefinite. The term “low concentration” is not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. The instant invention is aimed at producing trifluoroiodomethane with a “low concentration” of methyl propane. There is no standard provided for defining the concentration of methyl propane as low and therefore, the scope of the claim of a “low concentration” of methyl propane remains unclear to one of ordinary skill in the art.
Claim 16 is 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.
Claim 16 recites the limitation "carbon methyl propane" in the 7th line of the composition claim. The term “carbon methyl propane” does not represent the chemical formula of a material known to one skilled in the art. (see MPEP 2173.05(e) and MPEP 2173.05(t)) There is insufficient antecedent basis for this limitation in the claim. It is presumed applicant is referring to methyl propane therefore, for purposed of compact prosecution, it will be interpreted as methyl propane.
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.
Claims 1, 4, 10-12, 15, and 19 are rejected under 35 U.S.C. 103 as being obvious over Nair et al. (US20200062679A1, found in PTO-892) in view of Kumma et al. (Environ Sci Pollut Res, published 05/24/2022, found in PTO-892).
Nair et al. teaches that trifluoroacetyl iodide (CF3COI) is a compound that can be converted to trifluoroiodomethane (CF3I). Trifluoroiodomethane (CF3I), also known as perfluoromethyliodide, trifluoromethyl iodide, or iodotrifluoromethane, is a useful compound in commercial applications as a refrigerant or a fire suppression agent, for example. Trifluoroiodomethane is a low global warming potential molecule with negligible ozone depletion potential. Trifluoroiodomethane can replace more environmentally damaging materials (see paragraph 0003). In one embodiment, the present invention provides a gas-phase process for producing trifluoroiodomethane. The process comprises providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof, reacting the reactant stream in the presence of a first catalyst at a first reaction temperature from about 25° C to about 400° C to produce an intermediate product stream comprising trifluoroacetyl iodide, and reacting the intermediate product stream in the presence of a second catalyst at a second reaction temperature from about 200° C to about 600° C to produce a final product stream comprising the trifluoroiodomethane (see paragraph 0010). The intermediate product stream may proceed directly to a first distillation column (see paragraph 0049). The first distillation column is configured for the separation of some of the by-products, reactants, and organic compounds from the trifluoroacetyl iodide to produce a purified intermediate product stream (see paragraph 0050). The concentration of the trifluoroacetyl iodide in the purified intermediate product stream may be greater than about 99 wt. % (see paragraph 0051). The concentration of some impurities in the purified intermediate product stream may detract from the further use of the trifluoroacetyl iodide. Thus, if the trifluoroacetyl halide in the reactant stream includes trifluoroacetyl chloride, the purified intermediate product stream includes from about 1 ppm (part per million by weight) to about 20,000 ppm (about 2 wt. %) in total of compounds selected from the group consisting of chlorotrifluoroethane, trifluoroacetyl chloride, iodotrifluoromethane, trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetic acid and chlorotrifluoromethane (see paragraph 0052). The trifluoroacetyl iodide in the purified intermediate product stream reacts within the second reactor to produce a final product stream comprising trifluoroiodomethane (see paragraph 0057). The final product stream may proceed directly to a second distillation column (See paragraph 0069). The purified final product composition has a trifluoroiodomethane concentration greater than 99 wt. % (see paragraph 0073). In another embodiment, the present invention provides a gas-phase process for producing trifluoroacetyl iodide. The process comprises providing a reactant stream comprising hydrogen iodide and at least one trifluoroacetyl halide selected from the group consisting of trifluoroacetyl chloride, trifluoroacetyl fluoride, trifluoroacetyl bromide, and combinations thereof, and reacting the reactant stream in the presence of a first catalyst at a reaction temperature from about 25° C to about 400° C to produce a product stream comprising the trifluoroacetyl iodide (see paragraph 0011). Examples are given of the processes as described above to produce the intermediate trifluoroacetyl iodide (see Examples 1-4). In an Example, the separation of trifluoroacetyl iodide is described. A mixture containing about 80 wt. % trifluoroacetyl iodide, about 10 wt. % trifluoroacetyl chloride, about 5 wt. % hydrogen iodide, and about 5 wt. % hydrogen chloride can be charged into a distillation column (See Example 7). Further examples are given for the process of producing trifluoroiodomethane from the intermediate trifluoroacetyl iodide (see Examples 8 and 9).
Nair et al. differs from that of the instantly claimed invention in that Nair et al. does not recite producing trifluoroiodomethane with a low concentration of methyl propane and purifying the intermediate product stream to remove methyl propane. As required by instant claim 11, Nair et al. does not teach wherein the amount of methyl propane in the purified intermediate stream is about 50 ppm or less. As required by instant claim 19, Nair et al. does not teach the process to produce trifluoroacetyl iodide with a low concentration of methyl propane.
Kumma et al. teaches the usage of domestic refrigeration units has been increased tremendously in recent times due to the dependency of the mankind on refrigeration. The advancement in refrigeration technology has reduced the cost of the refrigeration unit and also enhanced its performance. It must be appreciated here that it is also due to the availability of wide range of refrigerants such as HCs, HFCs, and HCFCs. Even though a variety of refrigerants exist to date, their usage is abandoned (negative impact on environment) due to the safety agreements signed by different nations. Therefore, researchers shifted their concentration in identifying safe, non-flammable, low GWP, and zero ODP eco-friendly refrigerants. Hydrocarbons are one set of the refrigerants that possess low GWP and ODP but are highly flammable. It is a common practice of the researchers to blend the flammable mixtures with the inert dilutants to reduce their flammability. In this context, various studies were conducted earlier with different refrigerant mixtures to meet the above requirements (see Introduction and Literature Review section). This paper presents the environment-friendly mixture compositions of hydrocarbons (HC)– and hydrofluorocarbon (HFC)–based ternary mixtures that can be better alternatives for R134a in domestic refrigeration units. Combustible refrigerant HCs (R290, R600, R600a (also known as methyl propane or isobutane)) and HFCs (R152a and R161) are used along with the dilutants R13I1 (also known as trifluoroiodomethane), R245fa, R134a, R227ea, and R125 and their flammability studies were carried out theoretically (see Abstract).
It would have been obvious before the effective filing date of the claimed invention to combine the method as taught by Nair et al. with the decrease in concentration of flammable impurities such as methyl propane as taught by Kumma et al. to arrive at the claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to combine the teachings of the method to produce trifluoroiodomethane or trifluoroacetyliodide with the decrease in concentration of methyl propane by appropriate methods known to one of skill in the art because, as taught by Kumma et al., methyl propane is a flammable refrigerant and it is commonly blended with inert dilutants to reduce flammability. One of ordinary skill in the art would have a reasonable expectation of success because both references are aimed to refrigerant mixtures that have minimal environmental impact.
Claims 2-3 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Nair et al. (US20200062679A1, found in PTO-892) in view of Kumma et al. (Environ Sci Pollut Res, published 05/24/2022, found in PTO-892). as applied to claim 1 and 19, above, and further in view of Monsanto et al. (GB1350726A, published 04/24/1974, found in PTO-892).
The combined teachings of Nair et al. and Kumma et al. were discussed above.
The combined teachings of Nair et al. and Kumma et al. differ from that of the instantly claimed invention in that Nair et al. and Kumma et al. do not teach wherein the amount of iodomethane or iodopropane in the hydrogen iodide (HI) is less than 250 ppm. As required by instant claim 20, the combined teachings of Nair et al. and Kumma et al. do not teach wherein the amount of iodomethane in the hydrogen iodide is less than 250 ppm.
Monsanto et al. teaches the purification of carboxylic acids produced by a catalytic system containing halogen components and which streams contain residual halogen components and water. Carboxylic acids produced by the above-described process contain water and relatively small amounts of halogen components as contaminants. In order that the carboxylic acids produced by such processes can be utilized in further reactions and other uses, they must generally be freed from any water which is present as well as the small amounts of halogen contaminants present (see page 1, left column, paragraphs 2-4). The carboxylic acid stream fed to the distillation column will comprise in addition to the carboxylic acid a substantial proportion of water and an alkyl halide such as methyl iodide and a relatively small proportion of an ionizable halide such as hydrogen iodide. An overhead stream is removed and condensed in a condenser, the condensed stream passing to either storage or recycle to the preceding catalytic process. Provision is made for recycle of a portion of the overhead to serve as reflux in the column. This overhead stream comprises by far the major portion of the water charged to the column as well as essentially all of the alkyl halide contained in the feed along with a very minor proportion of the hydrogen halide contained therein. Since recovery of the halogen values represents a distinct economic advantage of the process, the overhead stream is preferably recycled to the prior catalytic production process. It has been found that contrary to the alkyl halide component which is quite volatile under all normal column operating conditions, the hydrogen halide demonstrates an unexpected property which contributes to the efficient operation of the present purification process. The hydrogen halide is quite soluble in carboxylic acid/water mixtures containing at least a small amount of water, generally from about three to eight percent or more of water, while it is increasingly less soluble, or more volatile, in carboxylic acid/water mixtures containing lower quantities of water. In a distillation column operated so as to take overhead all or most of the water charged thereto as vapor then very little hydrogen halide will be present in the overhead vapor stream, but will tend to pass down the upper portion of the column in solution in the liquid carboxylic acid/water mixture.
It would have been obvious before the effective filing date of the claimed invention to combine the method for producing trifluoroiodomethane or trifluoroacetyl iodide as taught by the combined teachings Nair et al. and Kumma et al. with the purification process as taught by Monsanto et al. to arrive at the claimed invention of using hydrogen iodide essentially free of an alkyl halide (iodomethane or iodopropane) in the production of trifluoroiodomethane. It would have been prima facie obvious for one of ordinary skill in the art to combine the process of producing trifluoroiodomethane or trifluoroacetyl iodide as taught by Nair et al. and Kumma et al. with the purification process taught by Monsanto et al. because, as taught by Monsanto et al, recovery of the halogen components represents a distinct economic advantage of the process. One of ordinary skill in the art would have a reasonable expectation of success because all references are aimed at improvements in industrial catalytic systems.
Claims 5-7 are rejected under 35 U.S.C. 103 as being unpatentable over Nair et al. (US20200062679A1, published 02/27/2020, found in PTO-892) as applied to claim 1, above, and further in view of Merkel et al. (WO2023288198A1, filed 07/11/2022, found in PTO-892).
The applied reference (Merkel et al.) has a common inventor and assignee with the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2).
This rejection under 35 U.S.C. 103 might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C.102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B); or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement. See generally MPEP § 717.02.
The teachings of Nair et al. were discussed above.
The teachings of Nair et al. differ from that of the instantly claimed invention in that Nair et al. does not teach wherein the trifluoroacetyl iodide is purified by solvent extraction, wherein the solvent used for the solvent extraction is selected from the group consisting of hydrocarbons and chlorinated compounds, and wherein the solvent used for the solvent extraction is regenerated by distillation.
Merkel et al. teaches methods for solvation and removal of iodine-containing species. A feed stream comprising the components to be recovered, such as trifluoroacetyl iodide (TFAI), and trifluoroacetic acid, for example, is fed to a first column, along with a solvent. The first column includes a condenser and rectification section to allow for reflux. Optionally, the first column includes a reboiler and stripping section. A first overhead vapor product contains the component to be recovered, such as trifluoroacetyl iodide (TFAI). A first bottoms product 96 may include a solvent and iodine. The first bottoms product is conveyed to a second column. The second column includes a reboiler and a stripping section. Optionally, the second column includes a condenser and a rectification section. A second overhead product may include solvent in the form of a vapor or a liquid. The overhead product may be recycled back to the first column. Optionally, fresh solvent may be added to stream. A second bottoms product from the second column may include liquid iodine (see paragraph 0057). The solvent in the method described above may be a solvent with high solubility of iodine. The solvent may have a vapor pressure higher than that of iodine but lower than that of the components being recovered in the gas stream. Suitable solvents may include benzene; xylenes, such as paraxylene, metaxylene, and alkylated benzenes, such as mesitylene (1,3,5-trimethylbenzene) and toluene; dimethylformamide (DMF); and dimethyl sulfoxide (DMSO), for example (see paragraph 0059).
It would have been obvious before the effective filing date of the claimed invention to combine the process to produce trifluoroiodomethane as taught by Nair et al. with the purification of trifluoroacetyl iodide by solvent extraction (or stripping) using a hydrocarbon solvent and regenerating the solvent in the process of stripping or extraction to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to combine the method to make trifluoroiodomethane as taught by Nair et al. with the purification of the intermediate product (trifluoroacetyl iodide) by stripping (solvent extraction with regeneration of the solvent) using a hydrocarbon solvent because, as taught by Nair et al., the concentration of some impurities in the purified intermediate product stream may detract from the further use of the trifluoroacetyl iodide.
Claims 13 and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Nair et al. (US20200062679A1, published 02/27/2020, found in PTO-892) in view of Kumma et al. (Environ Sci Pollut Res, published 05/24/2022, found in PTO-892) as applied to claim 1, above, and further in view of Ota et al. (JP 2021173454A, published 11/01/2021, found in PTO-892).
The combined teachings of Nair et al. and Kumma et al. were discussed above.
The combined teachings of Nair et al. and Kumma et al. differ from that of the instant invention in that the combined teachings of Nair et al. and Kumma et al. do not teach further comprising purifying the final product stream comprising trifluoroiodomethane (CF3I) with an adsorbent selected from the group consisting of molecular sieves, carbon, carbon molecular sieves, alumina, and zeolites.
Ota et al. teaches when trifluoroiodomethane (CF3I) is mixed with a refrigerant such as difluoromethane (HFC32), combustibility can be suppressed while keeping GWP low. Among the deterioration reaction products produced by the decomposition of trifluoroiodomethane, trifluoromethane has a GWP = 12400 and is a substance having a high greenhouse effect. When the concentration of trifluoromethane increases, there is a problem that the GWP of the refrigerant increases. Therefore, it is possible to obtain a refrigerant having a low GWP and low flammability. However, trifluoroiodomethane undergoes a chemical reaction in the presence of water, oxygen, heat, etc. and decomposes to produce trifluoromethane (CHF3), which is a type of hydrofluorocarbon, hydrogen fluoride, hydrogen iodide, and the like (see lines 101-105). In the refrigeration cycle apparatus according to the present embodiment, an adsorbent that adsorbs trifluoromethane is installed at such a location. By installing an adsorbent that adsorbs trifluoromethane, the increase in the concentration of trifluoromethane in the refrigeration cycle is suppressed, the increase in GWP due to the deterioration of the refrigerant is continuously suppressed, and the environmental compatibility of the refrigeration cycle equipment is suppressed and ensure reliability (see lines 184-188). As the desiccant, synthetic zeolite having a pore size for adsorbing water, for example, zeolite such as molecular sieve, silica gel, activated alumina and the like can be used. As the desiccant, those having a pore size equal to or smaller than the effective diameter of water and larger than the effective diameter of the refrigerant component, refrigerating machine oil, additives, trifluoromethane and the like are preferable. That is, it is preferable that water is selectively adsorbed and it is difficult to adsorb a refrigerant component larger than water, refrigerating machine oil, additives, trifluoromethane and the like (see lines 234-239).
It would have been obvious to combine the teachings of Nair et al., Kumma et al., and Ota et al. before the effective filing date of the claimed invention by purifying the product stream of trifluoroiodomethane as produced by the method as taught by Nair et al. and Kumma et al. with an adsorbent such as molecular sieves, alumina, or zeolites as taught by the refrigeration cycle apparatus of Ota et al. It would have been prima facie obvious to combine the method to make trifluoroiodomethane with the purification of trifluoroiodomethane using an adsorbent because, as taught by Ota et al., trifluoroiodomethane can be used as a refrigerant with a low GWP if by-products such as trifluoromethane are removed by means such as adsorption. One of ordinary skill in the art would have a reasonable expectation of success because all references involve that are or could potentially be used as refrigerants.
Claims 16-18 are rejected under 35 U.S.C. 103 as being unpatentable over Nair et al. (US20200062679A1) in view of Tian et al. (JSEA, published 10/25/2016, found in PTO-892)
Claim 16 recites “carbon methyl propane” in the 7th line of the composition claim. In the interest of compact prosecution, the examiner will interpret the limitation of “less than 100 ppm carbon methyl propane” to mean “less than 100 ppm methyl propane”.
Nair et al. teaches the purified final product composition has a trifluoroiodomethane
concentration greater than 99 wt. %. Preferably, the concentration of the trifluoroiodomethane in the purified final product composition may be greater than 99.5 wt. %. More preferably, the concentration of the trifluoroiodomethane in the purified final product composition may be greater than 99.7 wt. %. Most preferably, the concentration of trifluoroiodomethane in the purified final product composition may be greater than 99.9 wt. % (see paragraph 0073). The concentration of some impurities in the purified final product stream may detract from the performance of the trifluoroiodomethane and its intended purpose as an environmentally safe, non-toxic gas. If the trifluoroacetyl halide in the reactant stream includes trifluoroacetyl chloride, the purified final product composition includes from 1 ppm (part per million by weight) to 500 ppm of chlorotrifluoroethane, less than 500 ppm hexafluoroethane, less than 500 ppm trifluoromethane, less than 100 ppm carbon monoxide, and less than 1 ppm hydrogen chloride. It is preferred that the purified final product stream includes from 1 ppm to 250 ppm of chlorotrifluoroethane, less than 250 ppm hexafluoroethane, less than 250 ppm trifluoromethane, less than 50 ppm carbon monoxide, and less than 0.5 ppm hydrogen chloride. It is more preferred that the purified final product stream includes from 1 ppm to 100 ppm of chlorotrifluoroethane, less than 10 ppm hexafluoroethane, less than 100 ppm trifluoromethane, less than 10 ppm carbon monoxide, and less than 0.2 ppm hydrogen chloride (see paragraph 0074). The purified final product composition may further comprise in amounts from 1 ppm to 500 ppm in total of compounds selected from the group consisting of trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde, and trifluoroacetyl chloride (see paragraph 0075).
Nair et al. differs from that of the instantly claimed invention in that Nair et al. does not teach the composition comprising less than 100 ppm methyl propane and wherein the amount of methyl propane is less than 70 ppm as required by instant claim 18.
Tian et al. teaches a theoretical and experimental study of explosion limits and the inhibition of flammable refrigerants. The purity of flammable gases could affect their explosion limits, because the presence of inert gases in unpurified flammable gases will decrease the range of explosion limits. Inert gases like nitrogen, carbon dioxide, and water vapor influence the explosion limits by diluting the flammable gases, isolating oxygen, and cooling the gases. When there are alkyl halides in the flammable gases, these alkyl halides can not only dilute, isolate and cool, but more importantly, they can also chemically inhibit combustion and explosion reactions. Furthermore, alkyl halides also have the ability to increase the minimum explosion limits and ignition energies of flammable refrigerants, which will significantly reduce the explosion limit range. For these reasons, most of the gas-extinguishing systems comprise alkyl halides (see Section 2.2). Flammable refrigerants such as R290, R600 and R600a are ideal substitutes for CFCs and HCFCs, but they can only be used in refrigerators with small volume since their flammability limits their use [10]. Azeotropic or non-azeotropic refrigerants are obtained by combining Halon alternatives (CF3I, R134a) with flammable refrigerants (R290, R600 and R600a). These refrigerants with different concentration ratios can reduce the explosion limits range and the flammability of flammable refrigerants, raise the lower explosion limit and ignition energy. When Halon substitutes reach a certain concentration, they can render the refrigerant mixture to be an inert nonflammable refrigerant, which can solve the safety problem of flammable refrigerants. Therefore, this method can be used to make substitutes such as the ideal R12 and R22 refrigerants (see Section 5).
It would have been obvious before the effective filing date of the claimed invention to combine the trifluoroiodomethane composition taught by Nair et al. with a low concentration of the flammable refrigerant R600a (methyl propane) as taught by Tian et al. to arrive at the claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to include an amount of methyl propane in the composition with trifluoroiodomethane because, as taught by Tian et al., azeotropic or non-azeotropic refrigerants are obtained by combining Halon alternatives such as trifluoroiodomethane with flammable refrigerants such as R600a or methyl propane which makes for an ideal R12 or R22 refrigerant substitute. One of ordinary skill in the art would have a reasonable expectation of success because both references aim to improve refrigerant mixtures.
Claim 19 is rejected under 35 U.S.C. 103 as being obvious over Nair et al. (US20200062679A1, found in PTO-892) in view of Wang et al. (US20220112226A1, found in PTO-892).
The applied reference (Wang et al.) has a common inventor and assignee with the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2).
This rejection under 35 U.S.C. 103 might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C.102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B); or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement. See generally MPEP § 717.02.
The teachings of Nair et al. were discussed above.
The teachings of Nair et al. differ from that of the instantly claimed invention in that Nair et al. does not teach producing trifluoroacetyl iodide with a low concentration of methyl propane.
Wang et al. teaches trifluoroacetyl iodide compositions including at least one organic impurity and at least one inorganic impurity. Compositions of trifluoroacetyl iodide are needed that allow more economical operation because the production of trifluoroiodomethane from trifluoroacetyl iodide may be subject to undesirable side reactions. Even with the impurities, the compositions have been found to be suitable for the manufacture of trifluoroiodomethane (see paragraph 0014). It has been found that some other organic impurities in the trifluoroacetyl iodide composition have relatively little effect in the efficiency of the process. Such impurities generally pass through the reactor without reacting and do not corrode the processing equipment. Examples of such organic impurities include a Markush group including methyl propane (see paragraph 0018). Figure 1 in Wang et al. shows a unit directed at the process of producing trifluoroacetyl iodide. The product stream 26 may proceed directly to a distillation column 28. The distillation column 28 is configured for the separation of some of the by-products, reactants, and organic compounds from trifluoroacetyl iodide to produce a purified product stream 32 (see paragraph 0040). The successful manufacture of trifluoroiodomethane from trifluoroacetyl iodide compositions according to the disclosure of Wang et al. is demonstrated.
It would have been obvious to combine the teachings of Nair et al. and Wang et al. before the effective filing date of the instant invention by producing trifluoroiodomethane with low concentrations of methyl propane by purifying the intermediate product stream to remove organic impurities such as methyl propane to arrive at the claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to combine the process for producing trifluoroiodomethane as taught by Nair et al. with the removal of methyl propane from the intermediate stream of trifluoroacetyl iodide to produce trifluoroiodomethane with a low concentration of methyl propane as taught by Wang et al. because, as taught by Wang et al., compositions of trifluoroacetyl iodide are needed that allow more economical operation because the production of trifluoroiodomethane from trifluoroacetyl iodide may be subject to undesirable side reactions. One of ordinary skill in the art would have a reasonable expectation of success because both references aim to improve processes to make trifluoroiodomethane.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
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Claims 1, 4, 8-10, and 19 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1, 11, 12, and 15 of copending Application No. 18/570415 (Kopkalli et al.) in view of Wang et al. (US20220112226A1, found in PTO-892).
Kopkalli et al. recites, in Claim 1, a process for producing trifluoroiodomethane (CF3I), the process comprising:
(a) providing a first reactant stream comprising hydrogen iodide (HI);
(b) reacting the first reactant stream with a second reactant stream comprising trifluoroacetyl chloride (TFAC) to produce an intermediate product stream comprising trifluoroacetyl iodide (TFAI); and
(c) reacting the intermediate product stream to produce a final product stream comprising trifluoroiodomethane (CF3I).
Kopkalli et al. recites, in claim 11, the process of claim 1, wherein the intermediate product stream further comprises at least one of trifluoroacetyl chloride (TFAC), hydrogen iodide (HI), hydrogen chloride (HCl), trifluoroacetic acid (TFA), trifluoroiodomethane (CF3I), an iodine-containing species and carbon monoxide (CO), and step (b) further comprises purifying the intermediate product stream to obtain a purified intermediate product stream having a concentration of trifluoroacetyl iodide (TFAI) of greater than about 99%. Kopkalli et al. recites, in claim 12, the process of claim 11, wherein purifying the intermediate product stream further comprises:
(i) feeding the intermediate product stream into a first distillation column to obtain a first overhead stream comprising at least one of trifluoroacetyl chloride (TFAC), hydrogen iodide (HI), hydrogen chloride (HCl), trifluoroiodomethane (CF3I), and carbon monoxide (CO) and first a bottoms stream comprising trifluoroacetyl iodide (TFAI), trifluoroacetic acid (TFA), and iodine-containing species; and
(ii) feeding the first overhead stream to a second distillation column to obtain a second overhead stream comprising hydrogen chloride (HCl) and a second bottoms stream comprising hydrogen iodine (HI) and trifluoroacetyl chloride (TFAC). Kopkalli et al. further recites, in claim 15, the process of claim 1, further comprising removing at least one iodine-containing species from a stream comprising trifluoroacetyl iodide (TFAI) or trifluoroiodomethane (CF3I) by contacting the stream comprising trifluoroacetyl iodide (TFAI) or trifluoroiodomethane (CF3I) with carbonaceous materials to remove at least one of hydrogen iodide (HI), hydrogen triiodide (HI3) and iodine (I2) from the stream.
The difference between the claims of Kopkalli et al. and the claimed invention is that Kopkalli et al. does not recite purifying the intermediate product stream to remove methyl propane as required by instant claim 1. As required by claim 19, Kopkalli et al. does not recite producing trifluoroacetyl iodide with a low concentration of methyl propane.
The independent teachings of Wang et al. are as discussed above.
It would have been obvious before the effect filing date of the claimed invention to combine the recited process of Kopkalli et al. with the purification of trifluoroacetyl iodide to remove methyl propane as disclosed in Wang et al. to arrive at the claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to combine the purification of trifluoroacetyl iodide to remove methyl propane with the process to produce trifluoroiodomethane because compositions of trifluoroacetyl iodide are needed that allow more economical operation because the production of trifluoroiodomethane from trifluoroacetyl iodide may be subject to undesirable side reactions. One of ordinary skill in the art would have a reasonable expectation of success because both references aim to improve the production of trifluoroiodomethane.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1, 4, 8-11, 15, and 19 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1, 11, 12, and 15 of copending Application No. 18/570415 (Kopkalli et al.) in view of Kumma et al. (Environ Sci Pollut Res, published 05/24/2022, found in PTO-892).
The claims as recited by Kopkalli et al. were discussed above.
The difference between the claims of Kopkalli et al. and the claimed invention is that Kopkalli et al. does not recite purifying the intermediate product stream to remove methyl propane as required by instant claim 1. As required by instant claim 11, Kopkalli et al. does not recite wherein the amount of methyl propane in the purified intermediate product stream is about 50 ppm or less. As required by instant claim 15, Kopkalli et al. does not recite wherein the amount of methyl propane in the trifluoroiodomethane product is about 70 ppm or less. As required by claim 19, Kopkalli et al. does not recite producing TFAI with a low concentration of methyl propane.
The teachings of Kumma et al. were discussed above.
It would have been obvious before the effective filing date of the claimed invention to combine the recited process of Kopkalli et al. with the removal or decrease in concentration of flammable impurities such as methyl propane as taught by Kumma et al. to arrive at the claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to combine the process to produce trifluoroiodomethane as recited by Kopkalli et al. with the removal or decrease in concentration of methyl propane by methods known to one of skill in the art because, as taught by Kumma et al., methyl propane is a flammable refrigerant and it is commonly blended with inert dilutants to reduce flammability. One of ordinary skill in the art would have a reasonable expectation of success because both references are aimed to refrigerant mixtures that have minimal environmental impact.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 16-18 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1, 11, 12, and 15 of copending Application No. 18/570415 (Kopkalli et al.) in view of Nair et al. (US20200062679A1) and in further view of Tian et al. (JSEA, published 10/25/2016, found in PTO-892)
Claim 16 recites “carbon methyl propane” in the 7th line of the composition claim. In the interest of compact prosecution, the examiner will interpret the limitation of “less than 100 ppm carbon methyl propane” to mean “less than 100 ppm methyl propane”.
The claims of Kopkalli et al. were discussed above.
The claims of Kopkalli et al. differ from that of the instantly claimed invention in that Kopkalli et al. does not recite a composition comprising at least 99 wt.% of trifluoroiodomethane, less than 500 ppm chlorotrifluoroethane, less than 500 ppm hexafluoroethane; less than 500 ppm trifluoromethane; less than 100 ppm carbon monoxide; less than 100 ppm carbon methyl propane and less than 1 ppm hydrogen chloride.
The teachings of Nair et al. were discussed above.
The teachings of Tian et al. were discussed above.
It would have been obvious before the effective filing date of the claimed invention to combine the method to make a trifluoroiodomethane composition recited by Kopkalli et al. and taught by Nair et al. with a low concentration of the flammable refrigerant R600a (methyl propane) as taught by Tian et al. to arrive at the claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to include an amount of methyl propane in the composition with trifluoroiodomethane because, as taught by Tian et al., azeotropic or non-azeotropic refrigerants are obtained by combining Halon alternatives such as trifluoroiodomethane with flammable refrigerants such as R600a or methyl propane which makes for an ideal R12 or R22 refrigerant substitute. One of ordinary skill in the art would have a reasonable expectation of success because both references aim to improve refrigerant mixtures.
Conclusion
No claim is found allowable.
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/KRISTEN W BRADY/Examiner, Art Unit 1692
/SCARLETT Y GOON/Supervisory Patent Examiner
Art Unit 1693