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
The claim amendments and remarks filed on 06/05/2026 is acknowledged. Claims 1, 16, and 19 are amended. Claim 20 is cancelled. Claims 21-25 have been added.
Claims 1-19 and 21-25 are pending.
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.
Withdrawn Objections
The claim objection for claim 3 is withdrawn in view of claim 3 being amended from reciting “amont” to “amount.”
Withdrawn Rejections
35 U.S.C. 112(b) rejection for claim 1 is withdrawn in view of claim 1 being amended from reciting a “low concentration” of methyl propane to “having an amount of methyl propane of 100 ppm or less.”
35 U.S.C. 112(b) rejection for claim 16 is withdrawn in view of claim 16 being amended from “carbon methyl propane” to “methyl propane.”
35 U.S.C. 103 rejection of claims 1, 4, 10-12, 15, and 19 over Nair et al. in view of Kumma et al. is
withdrawn in favor of the new 35 USC 103 rejections discussed below and claim 19 being amended to now include “having an amount of iodomethane less than 150 ppm.”
35 U.S.C. 103 rejection of claims 2-3 and 20 over Nair et al. in view of Kumma et al. in further
view of Monsanto et al. is withdrawn in favor of the new 35 USC 103 rejections discussed below and in view of claim 20 being cancelled.
35 U.S.C. 103 rejection of claims 5-7 over Nair et al. in view of Kumma et al. further in view of
Merkel et al. is withdrawn in favor of the new 35 USC 103 rejections discussed below.
35 U.S.C. 103 rejection of claims 13-14 over Nair et al. in view of Kumma et al. further in view of
Ota et al. is withdrawn in in favor of the new 35 USC 103 rejections discussed below.
35 U.S.C. 103 rejection of claims 16-18 over Nair et al. in view of Tian et al. is withdrawn in view
of claim 16 being amended to now include the composition having an amount of less than 100 ppm
chlorotrifluoroethane, less than 100 ppm hexafluoroethane, less than 100 ppm trifluoromethane, and
less than 20 ppm carbon monoxide.
35 U.S.C. 103 rejection of claim 19 over Nair et al. in view of Wang et al is withdrawn in view of claim 19 being amended to now include “having an amount of iodomethane less than 150 ppm.”
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, and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Nair et
al. (US20200062679A1, published 02/27/2020, 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.
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 teach the presence of methyl propane in the process to make trifluoroiodomethane and removing methyl propane by purifying the intermediate product stream. 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.
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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 (with the TFAI compositions shown above) according to the disclosure of Wang et al. is demonstrated.
It would have been obvious before the effective filing date of the claimed invention to combine
the teachings of Nair et al. with the teachings of Wang et al. by using the purification method to produce
trifluoroacetyl iodide compositions, as taught by Wang et al., in the method to produce
trifluoroiodomethane, as taught by Nair et al., 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 teachings of Nair et al. with
the teachings of Wang et al. because, as taught by Wang et al., the process to make trifluoroacetyl iodide includes methyl propane as a by-product which would flow naturally into the process to make trifluoroiodomethane from trifluoroacetyl iodide also having methyl propane as a by-product. Furthermore, as taught by Wang et al., a stream of trifluoroacetyl iodide can be purified to contain methyl propane in concentrations as low as 0 ppm and successfully be used to produce trifluoroiodomethane. One of ordinary skill in the art would have a reasonable expectation of success because trifluoroiodomethane was successfully manufactured using the compositions taught by Wang et al.
Regarding instant claim 1, Nair et al. teaches providing a gas stream comprising hydrogen iodide,
corresponding to the instant first reactant stream. The hydrogen iodide is reacted with at least one
trifluoroacetyl halide including trifluoroacetyl chloride, corresponding to the instant second reactant
stream. This produces an intermediate stream comprising trifluoroacetyl iodide, corresponding to the
instant intermediate product stream. Wang et al. teaches purifying a stream of trifluoroacetyl iodide
(TFAI) to produce TFAI compositions with concentrations of methyl propane as low as 0 ppm. The TFAI
compositions, as taught by Wang et al., would then be used in the second reactor, as taught by Nair et
al., to produce a final product stream of trifluoroiodomethane which would naturally flow into a
trifluoroiodomethane composition containing less than 100 ppm of methyl propane because methyl
propane would not be produced in the decarbonylation reaction of TFAI wherein the products would
consist of carbon monoxide and trifluoroiodomethane.
Regarding instant claim 4, Wang et al. teaches purifying the TFAI by distillation, corresponding to
the instant distillation.
Regarding instant claim 10, Wang et al. teaches concentrations as high as 99.4 wt%,
corresponding to the instant purified intermediate stream having a concentration greater than 99 wt%.
Regarding instant claim 11, Wang et al. teaches concentrations as low as 0 wt% methyl propane
in the purified TFAI, corresponding to the instant purified intermediate stream containing 50 ppm or less
of methyl propane.
Regarding instant claim 12, Nair et al. teaches the final product stream may proceed directly to a
second distillation column, corresponding to the instant purifying the final product stream CF3I by
distillation.
Regarding instant claim 15, a CF3I product containing 20 ppm or less of methyl propane would
naturally flow from a TFAI composition, as taught by Wang et al., which contains as low as 0 ppm methyl
propane.
Claims 2-3 are rejected under 35 U.S.C. 103 as being unpatentable over Nair et al.
(US20200062679A1, found in PTO-892) in view of Wang et al. (US20220112226A1, found in PTO-892)
as applied to claim 1 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 Wang et al. were discussed above.
The combined teachings of Nair et al. and Wang et al. differ from that of the instantly claimed
invention in that Nair et al. and Wang et al. do not teach wherein the amount of iodomethane and
iodopropane in the hydrogen iodide (HI) 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, as taught by the combined teachings Nair et al. and
Wang 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). 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 Wang et al., with the
purification process taught by Monsanto et al. because, as taught by Monsanto et al, purification of a mixture comprising alkyl halide and hydrogen iodide can be done as to remove any alkyl halide charged to the purification zone from the hydrogen iodide which flows naturally into producing hydrogen iodide containing less than 250 ppm of iodomethane and iodopropane. 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.
Regarding instant claims 2 and 3, Monsanto et al. teaches removing a stream containing a major
proportion of any hydrogen halide present in the zone which is essentially free of alkyl halide,
corresponding to the instant hydrogen iodide stream with less than 250 ppm of iodomethane and
iodopropane.
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) ) in view of Wang et al.
(US20220112226A1, 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 combined teaching of Nair et al. and Wang et al. were discussed above.
The combined teachings of Nair et al. and Wang et al. differ from that of the instantly claimed
invention in that Nair et al. and Wang et al. do 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. It was found that even purified trifluoroacetyl iodide (TFAI) feed material contained other iodine (l2)-containing species, such as I2, and HI3. During the conversion step of trifluoroacetyl iodide (TFAI) to trifluoroiodomethane (CF3I), the presence of iodine (I2)-containing species, such as I2 and HI3, together with additional I2 formed during this reaction as well as the reaction to produce trifluoroacetyl iodide (TFAI) from trifluoroacetyl chloride (TFAC) and hydrogen iodide (HI), caused increased corrosion of equipment and/or operational difficulties including flow, pressure control and plugging issues (see 007). 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. and Wang 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, as taught by Merkel et al., 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. and Wang et al., with
the purification of the intermediate product (trifluoroacetyl iodide) by stripping (solvent extraction with
regeneration of the solvent) using a hydrocarbon solvent, as taught by Merkel et al., because, as taught
by Merkel et al., the presence of Is-containing species causes corrosion to the equipment. One of ordinary skill in the art would have a reasonable expectation of success because Merkel et al. teaches a successful purification of TFAI by solvent extraction using hydrocarbon solvents.
Regarding instant claim 5, Nair et al. and Kumma et al. teach the process to make CF3I, corresponding to the instant process of claim 1, which is combined with the purification of TFAI by stripping, corresponding to the instant step of purifying TFAI by solvent extraction.
Regarding instant claim 6, Merkel et al. teaches suitable solvents for the extraction 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), corresponding to the instant solvent for the solvent extraction being hydrocarbons.
Regarding instant claim 7, Merkel et al. teaches a second overhead product may include solvent in the form of a vapor or a liquid and the overhead product may be recycled back to the first column, corresponding to the instant step of regenerating the solvent by distillation.
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 Wang et al.
(US20220112226A1, 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 teaching of Nair et al. and Wang et al. were discussed above.
The combined teachings of Nair et al. and Wang et al. differ from that of the instantly claimed
invention in that Nair et al. and Wang 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. and Wang et al. with the
teachings of 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 Wang 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 Ota et al. teaches a successful purification of CF3I using adsorbents.
Regarding instant claim 13, Ota et al. teaches purifying CF3I with an adsorbent, corresponding to
the instant purification of CF3I by adsorbent.
Regarding instant claim 14, Ota et al. teaches zeolite such as molecular sieve, silica gel, activated
alumina and the like can be used as the adsorbent, corresponding to the instant adsorbent selected
from the Markush group including molecular sieves, alumina, and zeolites.
Claims 19 and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (US20220112226A1, found in PTO-892) in view of Monsanto et al. (GB1350726A, published 04/24/1974, 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 Wang et al. were discussed above.
The teachings of Wang et al. differ from that of the instantly claimed invention in that Wang et al. does not teach the HI stream having an amount of iodomethane less than 150 ppm.
The teachings of Monsanto et al. were discussed above.
It would have been obvious before the effective filing date of the claimed invention to combine the teachings of Wang et al. with the teachings of Monsanto et al. by purifying the HI stream, as taught by Monsanto et al., and using this stream in the method to produce TFAI, as taught by Wang et al., to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to purify the HI stream and use this to make TFAI because, as taught by Monsanto et al., purification of a mixture comprising alkyl halide and hydrogen iodide can be done as to remove any alkyl halide charged to the purification zone from the hydrogen iodide which flows naturally into producing hydrogen iodide containing less than 150 ppm of iodomethane. One of ordinary skill in the art would have a reasonable expectation of success because Monsanto et al. teaches a successful example of a purified HI stream with essentially no iodoalkanes present.
Regarding instant claim 19, Wang et al. teaches a material flow of hydrogen iodide which is combined with the purification process of Monsanto et al. to achieve HI essentially free of alkyl halide, corresponding to the instant stream of HI having an amount of iodomethane less than 150 ppm. Wang et al. teaches reacting the HI with TFAC to produce a product stream comprising TFAI, corresponding to the instant reacting the first reactant stream with the second reactant stream to produce a final product stream.
Regarding instant claim 21, Wang et al. teaches, in Table 1, a TFAI composition sample comprising as low as 0 wt% methyl propane, corresponding to the instant TFAI stream having an amount of methyl propane of 100 ppm or less.
Claims 16-18 and 22-25 are rejected under 35 U.S.C. 103 as being unpatentable over Nair et al. (US20200062679A1, published 02/27/2020, PTO-892) in view of Tian et al. (JSEA, published 10/25/2016, found in PTO-892), as applied to claim 16 above.
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. 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. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976) (see MPEP 2144.05).
Regarding instant claim 16, 18, and 22-25, Nair et al. teaches a composition comprising a trifluoroiodomethane concentration greater than 99 wt. %, 1 ppm 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 which is combined with the teachings of Tian et al. which teaches the inclusion of methyl propane in refrigerant compositions in small volume.
Regarding instant claim 17, Nair et al. teaches the 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, corresponding to the instant composition comprising from 1 to 500 ppm in total of the compounds selected from the Markush group consisting of trifluoroacetyl fluoride, hexafluoropropanone, trifluoroacetaldehyde, and trifluoroacetyl chloride.
Response to Arguments
Applicant’s arguments filed on 06/05/2026 have been fully considered in so far as they apply to
the rejections of the instant office action, but were not persuasive.
In regard to the process to make trifluoromethyl iodide (CF3I), applicant states that the instant process is based on the identification of methyl propane as a specific impurity that is problematic because it causes difficult separation and points to [0013] to [0016] in the specification. Instant paragraphs 0013-0016 discuss the potential formation of a tangent pinch between methyl propane and CF3I as disclosed by Guo et al. and Maalem et al. Applicant further states the process of Nair et al. does not mention methyl propane or recognize the difficult separation of CF3I and methyl propane. Applicant further states the citation of Kumma et al. is based on hindsight because Kumma et al. discloses a very large number of refrigerants, with CF3I being only a single refrigerant of the many disclosed. Applicant further states methyl propane was preferentially selected from a number of potential components of refrigerant compositions which is, or may be, flammable. Lastly, applicant states a person having ordinary skill in the art would receive no guidance from Nair et al. that methyl propane is present in a process for producing CF3I and the skilled person would not select CF3I from Kumma et al. and know to minimize the amount of methyl propane.
The applicant’s argument has been fully considered, but is not found to be persuasive. Regarding applicant’s arguments that there is a problem of difficult separation between CF3I and methyl propane due to potential formation of a “tangent pinch” as evidenced by Guo et al. and Maalem et al., the references were only disclosed by the last name of the authors and did not include a citation. The reference being interpreted as Guo et al. (cited above) discusses the vapor-liquid equilibrium between trifluoroiodomethane and isobutane but teaches the system is zeotropic which one of ordinary skill in the art would not expect to cause separation issues (see Abstract). Furthermore, no publications by Maalem et al. were found to be focused on a tangent pinch between solely CF3I and methyl propane. Furthermore, one of ordinary skill in the art would not expect a difficult separation between CF3I and methyl propane due to vastly different boiling points which would be easily separatable by distillation. Therefore, this argument could not be evaluated as evidence to a potential separation difficulty.
In response to the arguments regarding the process to make CF3I, the rejection has been
withdrawn in favor of the new rejections discussed above. Therefore, applicant’s arguments are rendered moot.
In regard to the composition comprising CF3I, applicant states for similar reasons as set forth
above, instant claim 16 is patentable over Nair et al. as well as over Nair et al. in view of Tian et al.
In regard to the arguments regarding the composition, the rejection has been withdrawn in view
of applicant amending claim 16 in which the scope of the claim has been changed. Therefore, applicant’s
arguments are rendered moot.
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.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1, 4, and 8-10 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, 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 and a final product stream comprising CF3I having an amount of methyl propane of 100 ppm or less, as required by instant claim 1.
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 taught by 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.
Regarding instant claim 1, Kopkalli et al. recites a process for producing CF3I comprising (a) providing a first reactant stream comprising hydrogen iodide (HI), corresponding to the instant step of providing a first reactant stream of 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), corresponding to the instant step of reacting the first reactant stream with a second reactant stream comprising TFAC to produce an intermediate stream. Wang et al. teaches purifying a stream of trifluoroacetyl iodide (TFAI) to produce TFAI compositions with concentrations of methyl propane as low as 0 ppm, corresponding to the instant step of purifying the intermediate product stream. The TFAI composition, as taught by Wang et al., would then be used in the step (c), as recited by Kopkalli et al., to produce a final product stream of trifluoroiodomethane which would naturally flow into a trifluoroiodomethane composition containing less than 100 ppm of methyl propane because methyl propane would not be produced in the decarbonylation reaction of TFAI wherein the products would consist of carbon monoxide and trifluoroiodomethane.
Regarding instant claim 4, Wang et al. teaches purifying a stream of trifluoroacetyl iodide (TFAI) in a distillation column to produce TFAI compositions with concentrations of methyl propane as low as 0 ppm, corresponding to the instant step of purifying the intermediate product stream by distillation.
Regarding instant claims 8 and 9, Kopkalli et al. recites 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, corresponding to the instant TFAI being purified by an adsorbent of carbon.
Regarding instant claim 10, Wang et al. teaches a TFAI composition of 99.4 wt%, corresponding to the instant purified intermediate product stream being greater than about 99 wt%.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Response to Arguments
Applicant’s arguments filed on 06/05/2026 have been fully considered, but were not persuasive.
Applicant traverses the provisional nonstatutory double patenting rejection over Kopkalli et al. because of the amendments made to the independent claims as well as the arguments set forth above in view of Nair et al.
In regard to the arguments regarding the double patenting rejections, the rejections have been withdrawn in view of applicant amending independent claims 1, 16, and 19 in which the scope of the claims have been changed.
Conclusion
No claim is found allowable.
This action is made non-final in view of the new grounds of rejection made above, not necessitated by amendment.
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/KRISTEN W BRADY/Examiner, Art Unit 1692
/SCARLETT Y GOON/Supervisory Patent Examiner
Art Unit 1693
Prosecution Insights