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 .
Election/Restrictions
Applicant's election with traverse of Group II, claims 11-20 in the reply filed on 4/10/2026 is acknowledged. The traversal is on the ground(s) that as a result of the present amendments Groups I and II share the common feature of a liquid composition containing an organic solvent and IF5, wherein the concentration of IF5 is 1.8 mol or more per liter of the organic solvent. This is not found persuasive because the instant application was filed as a CON of PCT/JP2021/035763 and the restriction is not based on the Unity of Invention requirement. The application was properly restricted under US practice and remains valid for the reasons of record. See MPEP 800.
The requirement is still deemed proper and is therefore made FINAL.
Claims 1-10 and 22 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention there being no allowable generic or linking claim.
The Applicant’s election of species is also acknowledged. However, upon further consideration the species restriction requirement in the 2/12/2026 office action is withdrawn. Therefore, all species of organic solvent are under examination.
Claim Status
Claims 1-20 and 22 are pending. Claims 1-10 and 22 are withdrawn. Claims 11-20 are under examination.
Priority
The instant application was filed on 3/29/2023 and claims the benefit of priority to:
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See filing receipt dated 4/27/2023. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Specification
The disclosure is objected to because of the following informalities: the schemes and equations in the following paragraphs of the specification as filed are objected to because they are blurry and illegible or difficult to read: 0020, 0025, 0031, 0035, 0039, 0042, 0046, 0049, 0052, 0055, and 0087.
Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 15-20 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Each of claims 15-20, all depending from claim 11, refer to “the acid” or “the base”. There is a lack of antecedent basis for these limitations in the claims.
Notes for Calculations and Conversions in Prior Art Rejections
Osborne (Calorimetric Study of Iodine Pentafluoride: Heat Capacity between 5 and 350°K, Enthalpy of Fusion and Vaporization, Standard Entropy of the Vapor, and Other Thermodynamic Properties” J. Chem. Phys, 1971, p. 3790) may be cited as an evidentiary reference in the following rejections to teach that the density of liquid iodine pentafluoride (IF5) is 3.2 g/cm3 (g/mL) (see Table IV on p. 3793) and that the molecular weight (MW) of IF5 is 221.9 g/mol (top of Table I on p. 3791).
When converting from a weight of IF5 to mol of IF5, the weight in grams (g) is divided by the molecular weight in (g/mol). For example: X g IF5 x (1 mol/221.9 g IF5) = Y mol IF5.
When converting from a volume of IF5 to mol of IF5, the volume in (mL) is converted to weight in (g) using the density, and then the weight is converted to moles using the MW as shown above. For example, X mL IF5 x (3.2 g/mL IF5) x (1 mol/221.9 g IF5) = Y mol IF5.
The same calculations are applied when other chemicals have to be converted between volume, weight, and moles.
It is also noted that a concentration of mol per liter (mol/L) is equivalent to a concentration recited in mmol per mL (mmol/mL); and that the conversion between mmol to mol and mL to L is 1000 to 1.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 11-20 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Otsuka (JP2018104408A, published on 7/8/2018; US equivalent = US2020/0087230, published on 3/19/2020) as evidenced by Dichloromethane (“Density” from PubChem record for CID 6344 downloaded from https://pubchem.ncbi.nlm.nih.gov/compound/Dichloromethane#section=Density&fullscreen=true on 5/8/2026).
Otsuka teaches an example 2 in [0207] comprising a liquid solution of 6.6 g (20 mmol) of IF5-HF-pyridine complex and 5 mL of dichloromethane (a halogenated hydrocarbon). Otsuka teaches examples 3-5 in [0208-0218] comprising a liquid solution of 3.85 g (12 mmol) of IF5-HF-pyridine complex and 2.5 mL of dichloromethane. Otsuka teaches an example 6 in [0219-0223] comprising a liquid solution of 7.70 g (24 mmol) of IF5-HF-pyridine complex and 10 mL of dichloromethane. These correspond to concentrations of IF5 in dichloromethane of 4 mmol/mL; 4.8 mmol/mL; and 2.4 mmol/mL respectively. Therefore, all of these solutions meet the limitations of claims 11 and 13-20.
Further regarding claim 12, as evidenced by Dichloromethane, the density of said compound is 1.3 g/mL. Therefore, example 2 comprises 6.5 g dichloromethane; examples 3-5 comprise 3.25 g dichloromethane; and example 6 comprises 13 g dichloromethane. The total composition mass (dichloromethane + IF5-HF-pyridine complex) is 13.1 g for example 2; 7.1 g for examples 3-5; and 20.7 g for example 6. The mass percentage of dichloromethane is 50% for example 2; 46% for examples 3-5; and 63% in example 6. Therefore, all of the liquid solutions meet the limitations of claim 12. Also see MPEP 2131.
Claim(s) 11 and 13-20 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Adachi (JP2006151894A, published on 6/15/2006, including translation thereof).
Adachi teaches an Example 13, wherein 0.83 mL of acetonitrile (a nitrile organic solvent-claims 13 and 14) are combined with 6.6 g (30 mmol) of IF5, 5.0 mmol of compound 1, and 9.6 g (60 mmol) of Et3N-3HF to form a liquid mixture, which is stirred at 75°C for 4 hours to produce compounds of formula 2 and 3:
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. Thus, the concentration of IF5 in the acetonitrile is 36 mmol/mL, which falls within the claimed range. Adachi further teaches that the liquid composition comprises the Bronsted acid hydrogen fluoride (HF) and organic base triethylamine (Et3N) (claims 15-20). Also see MPEP 2131.
Claim(s) 11-14 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Engel (“Photolysis of Azoalkanes. Reactions and Kinetics of the 1-Cyclopropylcyclopentane-1,3-diyl Biradical and the 1-cyclopropylcyclopentyl Radical” J. Am. Chem. Soc. 1991, p. 2686) as evidenced by Osborne (full citation above) and Dichloromethane (“Density” from PubChem record for CID 6344 downloaded from https://pubchem.ncbi.nlm.nih.gov/compound/Dichloromethane#section=Density&fullscreen=true on 5/8/2026).
Engel teaches an experimental procedure for compound (61a) on p. 2694 which employs a 2.8 M (2.8 mol/liter) stock solution of IF5 in CH2Cl2 (a halogenated hydrocarbon) and 3.0 mL (8.5 mmol) of the 2.8M stock solution are used in the reaction. Both of these liquid compositions comprising IF5 and CH2Cl2 meet the limitations of claims 11, 13, and 14. Further regarding the 3.0 mL use solution above, as evidenced by Dichloromethane, the density of said compound is 1.3 g/mL and as evidenced by Osborne, the molecular weight of IF5 is 221.9. Converting 3.0 mL of the CH2Cl2 use solution to weight provides 3.9 g CH2Cl2; and 8.5 mmol of IF5 corresponds to a weight of 1.9 g. Therefore, the mass percentage of the CH2Cl2 based on the total amount of the composition (IF5 and CH2Cl2, 5.8 g total) 67%, which falls within the range of claim 12.
Also see MPEP 2131.
Claim(s) 11, 13, and 14 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kunigami (“Synthesis of fluoromethyl ethers and fluoromethyl esters by the reaction of the corresponding methylthiomethyl ethers and methylthiomethyl esters with IF5-pyridine-HF” Journal of Fluorine Chemistry, 2014, p. 101, of record in the IDS filed on 4/25/2023).
Kunigami teaches the preparation of IF5-pyridine-HF in section 4.2 on p. 103. The process comprises mixing (94 g, 0.37 mol) of IF5, with 200 mL (0.2 L) of CCl4, a halogenated hydrocarbon (claims 13-14). The concentration of IF5 in the liquid mixture is 1.85 mol/L, which falls within the claimed range. See MPEP 2131. A mixture of (37.5 g, 0.37 mol) pyridine-HF in CCl4 (50 mL, 0.05 L) is then added, however the concentration of IF5 in this liquid mixture is 1.48 mol/L, which falls outside the claimed range.
Claim(s) 11, 13, and 14 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Stevens (“Fluorination of Some Nitriles and Ketones with Bromine Trifluoride” J. Org. Chem, 1961, p. 1627) as evidenced by Osborne (full citation above) and Acetonitrile (“Density” from PubChem record for CID 6342 downloaded from https://pubchem.ncbi.nlm.nih.gov/compound/Acetonitrile#section=Density&fullscreen=true on 5/11/2026).
Stevens teaches an example of the fluorination of acetonitrile bridging col. 1-2 of p. 1629, wherein 0.87 g (0.021 mole) of acetonitrile, an organic solvent, is contacted with 10 mL of anhydrous hydrogen fluoride (HF) to produce a mixture thereof. Stevens then teaches an example wherein “the fluorination was conducted as described above, except that 8 mL of iodine pentafluoride (IF5) was the solvent”. This corresponds to a liquid mixture of 0.87 g (0.021 mole) acetonitrile and 8 mL of IF5. As evidenced by Acetonitrile, the density of acetonitrile is 0.79 g/mL. Therefore, the volume of the acetonitrile in the mixture is 1.10 mL, or 0.0011 L. There are 0.12 mol in 8 mL of IF5. Therefore, the concentration of IF5 is 0.12/.0011, or 109 mmol IF5 in acetonitrile, which meets the limitations of claims 11, 13, and 14. Also see MPEP 2131.
Claim(s) 11, 13, and 14 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Ayuba (“Selective trifluorination of alkyl aryl sulfides using IF5”, Tetrahedron, 2004, p. 11445, of record in the IDS filed on 11/6/2024) as evidenced by Osborne (full citation above) and Dichloromethane (“Density” from PubChem record for CID 6344 downloaded from https://pubchem.ncbi.nlm.nih.gov/compound/Dichloromethane#section=Density&fullscreen=true on 5/8/2026).
In section 4.2.1. on p. 11448-11449, Ayuba discloses a liquid solution of IF5 in methylene chloride (CH2Cl2, a halogenated hydrocarbon-claims 13-14) which comprises 0.776 g of a 16.7 mol% solution, 1.2 mmol). As evidenced by Dichloromethane, the density of said compound is 1.3 g/mL and as evidenced by Osborne, the density of IF5 is 3.2 g/mL therefore the density of the Ayuba solution is assumed to fall between these values. When 0.776 g of the solution is converted to volume using both densities, the volume range for the methylene chloride is 0.60 to 0.24 mL, which provides a concentration of IF5 in an amount from 2.0 to 3.2 mmol of IF5. This range completely falls within the range of claim 11. Also see MPEP 2131.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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