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 I (claims 1-4) in the reply filed on 2 April 2026 is acknowledged.
Applicant argues that unity exists because each group recites the production or use of a carbonyl halide generated from a halogenated methane/oxygen mixed gas under high-energy light irradiation. This argument is not persuasive because the mere presence or use of a common carbonyl halide intermediate does not establish a single general inventive concept, the common feature must be a “special technical feature,” i.e., a feature that defines the contribution which each claimed invention, considered as a whole, makes over the prior art. The identified common feature does not satisfy that standard.
The common feature relied upon by applicant is, at most, the production or use of a carbonyl halide intermediate. Carbonyl halides are known multifunctional reagents used in many unrelated chemical transformations. The prior art of record also shows photochemical production of carbonyl halides or carbonyl-halide-like compounds from halogenated hydrocarbons in the presence of oxygen and shows downstream reactions of such carbonyl species with different reactant classes. Therefore, the use of a carbonyl halide intermediate does not define the contribution of each claimed invention over the prior art.
Even assuming, solely for purposes of this analysis, that the particular photochemical production conditions of claims 1-4 may be novel, the later claims are not linked to that production step by a common special technical feature. Claims 5-6 are directed to reactions with fluorinated or non-fluorinated alcohols at a molar ratio of 1 or more to form carbonate compounds. Claims 7-8 are directed to reactions with fluorinated or non-fluorinated alcohols at a molar ratio of less than 1 to form halogenated formic acid ester compounds. Claim 9 is directed to a reaction with primary amine compounds to form isocyanates. Claim 10 is directed to a reaction with protected amino acid compounds or peptides to form amino acid-N-carboxylic anhydrides. Claim 11 is directed to reaction with amide compounds to form Vilsmeier reagents. These groups employ different reactant classes, proceed through different downstream reaction chemistries, and produce chemically and functionally different final products.
Applicant’s reliance on 37 CFR § 1.475(b)(3) is not persuasive. That provision concerns a product, a process specially adapted for the manufacture of that product, and a use of that product. The present claim set is not limited to one product, one specially adapted process for making that product, and one use of that same product. Rather, the claims recite one upstream production process and multiple downstream processes for making different product classes from different reactants. The claims therefore do not fit the product/process/use relationship contemplated by 37 CFR § 1.475(b)(3).
Applicant’s reliance on MPEP § 806.03 is also not persuasive. The claims do not merely define the same essential characteristics of a single disclosed embodiment with different breadth or terminology. Instead, the claims define multiple chemically distinct processes that require different starting reactants, different downstream reaction conditions, and different end products. The claims therefore are not directed to the same disclosed embodiment merely stated in different forms.
Applicant further argues that the Office has not established a serious search or examination burden. This argument is not persuasive. Examination of the elected photochemical carbonyl halide production process requires a search directed to gas-phase photochemical oxidation of halogenated methanes and carbonyl halide generation. Examination of the non-elected claims would additionally require searches directed to carbonate-forming reactions of alcohols, haloformate ester formation, isocyanate formation from amines, amino acid-N-carboxylic anhydride formation from protected amino acids or peptides, and Vilsmeier salt formation from amides. These are separate chemical product-forming technologies involving different reactant classes, reaction mechanisms, and end products. Requiring examination of all groups together would impose a serious search and examination burden.
Applicant’s argument that the International Searching Authority searched all claims is not controlling. The U.S. national-stage examiner must make an independent unity determination under 37 CFR § 1.475 and MPEP § 1893.03(d). A prior international search of multiple claims does not establish that the claims are linked by the same or corresponding special technical features, and it does not preclude the Office from requiring election in the national stage.
Accordingly, the traverse is not persuasive. Groups I-VI are not linked by the same or corresponding special technical feature and do not form a single general inventive concept. The restriction requirement is maintained. Applicant’s election of Group I, claims 1-4, is acknowledged. Claims 5-11 remain withdrawn from further consideration as drawn to non-elected inventions.
The requirement is still deemed proper and is therefore made FINAL.
Claim Objections
Claim 4 objected to because of the following informalities:
Claim 4 is objected to under 37 CFR § 1.75(c) as being in improper multiple dependent form. Claim 4 depends from “any one of claims 1 to 3.” However, claim 3 depends from “claim 1 or 2” and is itself a multiple dependent claim. A multiple dependent claim may not serve as a basis for another multiple dependent claim, directly or indirectly. See MPEP § 608.01(n).
For examination purposes, claim 4 is treated as a single dependent claim. Correction is required by rewriting claim 4 in proper dependent form, for example by making claim 4 depend from claim 1, claim 2, or claim 3 individually, or by otherwise eliminating the dependency from another multiple dependent claim.
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.
Claims 1-4 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 1 recites “irradiating a high energy light to the flowed mixed gas.” The term “high energy light” is a relative term and does not provide a clear, objective boundary for determining the scope of the claim. Claim 1 does not recite a wavelength, peak wavelength, photon energy, intensity, lamp type, spectral distribution, or other measurable parameter that identifies what light qualifies as “high energy light.”
Therefore, one of ordinary skill in the art would not be able to determine, with reasonable certainty, what light sources or irradiation conditions fall within the scope of claim 1.
The specification does not resolve the ambiguity. Although the specification describes preferred light including short wavelengths and provides examples of wavelength ranges, the claim itself does not incorporate any such objective limitation. As a result, the scope of “high energy light” remains uncertain because the claim does not define how much energy, what wavelength range, or what measurable property is required for the light to be considered “high energy.”
Claims 2-4 depend directly or indirectly from claim 1 and further recite the same “high energy light” limitation or irradiation of the mixed gas using such light. Accordingly, claims 2-4 are indefinite for the same reasons stated above with respect to claim 1.
Appropriate correction would require amendment of the claims to define the light using objective parameters, such as a wavelength or peak wavelength range, photon energy, intensity, or other measurable irradiation characteristic sufficient to establish the metes and bounds of the claimed method.
Claim Rejections - 35 USC § 102/103
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 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.
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.
Claims 1-4 is/are rejected under 35 U.S.C. 102(a)(1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Braun et al. (US Pat. 7,880,039 B2, hereafter “US’039.”
Regarding claim 1, US’039 discloses a method for producing a carbonyl halide, namely carbonyl fluoride, C(O)F₂, by photooxidizing CHClF₂ or CHF₃ with oxygen. See US’039, Abstract; col. 1, ll. 35-47. US’039 further discloses that CHClF₂, also identified as HCFC-22, is preferred. See US’039, col. 1, ll. 52-53. CHClF₂ is a halogenated methane having at least one chloro group. The claim recites a halogenated methane having one or more halogeno groups selected from chloro, bromo, and iodo, and does not exclude additional fluoro substituents. Thus, CHClF₂ reads on the claimed halogenated methane under the broadest reasonable interpretation.
US’039 further discloses preparing and flowing a mixed gas comprising oxygen and the halogenated methane. US’039 teaches continuously feeding the starting compound and an oxygen-containing gas, such as air or pure oxygen, into a flow apparatus and continuously drawing off the reaction product or reaction mixture. See US’039, col. 2, ll. 15-20. US’039 also discloses selecting pressure and temperature conditions so that the reaction mixture remains gaseous. See US’039, col. 1, ll. 58-60. US’039 further discloses irradiating the reaction mixture with light, including radiation outside the visible range, and radiation preferably in the range from 280 nm up to about 750 nm. See US’039, col. 1, ll. 35-51. Accordingly, US’039 discloses preparing a mixed gas comprising oxygen and a halogenated methane, flowing the mixed gas, and irradiating the flowed mixed gas with high energy light, as required by claim 1.
Regarding claim 3, US’039 discloses that the average residence time in the reaction vessel is advantageously between 0.01 and 30 minutes, preferably between 0.1 and 3 minutes, and more preferably between 0.3 and 1.5 minutes. See US’039, col. 2, ll. 20-24. These disclosed times correspond to 0.6 to 1800 seconds, preferably 6 to 180 seconds, and more preferably 18 to 90 seconds, which fall within the claimed irradiation time of 1 second or more and 10,000 seconds or less.
Regarding claim 4, US’039 discloses that the temperature is preferably in the range from 20 to 300°C, particularly 30 to 300°C, in particular 30 to 90°C, and very particularly 50 to 90°C. See US’039, col. 1, ll. 54-58. These disclosed ranges overlap and fall within the claimed temperature range of 40°C or higher and 200°C or lower.
To the extent US’039 is not considered to expressly anticipate claims 1-4, the claims would have been obvious over US’039. US’039 teaches the same gas-phase photochemical oxidation process using a halogenated methane and oxygen to produce a carbonyl halide. Any difference between the claimed method and US’039’s process, including the manner of preparing the gaseous mixture, irradiation time, and irradiation temperature, would have been an obvious matter of routine process optimization.
US’039 expressly teaches that the process may be continuous, that the starting compound and oxygen-containing gas are fed into a flow apparatus, that the reaction mixture remains gaseous, and that residence time depends on lamp type, radiation output, and irradiation-apparatus geometry. See US’039, col. 2, ll. 15-31. The claimed time and temperature ranges overlap US’039’s disclosed ranges. Absent evidence of criticality or unexpected results commensurate in scope with the claimed ranges, the claimed ranges would have been obvious. See In re Aller, 220 F.2d 454, 456 (CCPA 1955); In re Peterson, 315 F.3d 1325, 1329-30 (Fed. Cir. 2003).
Regarding claim 2, US’039 discloses irradiating the reaction mixture in a photochemical reactor using conventional irradiation lamps, including medium-pressure or high-pressure mercury radiators. See US’039, col. 2, ll. 42-54; col. 3, ll. 15-39. US’039 further teaches that the optimal residence time depends on, among other things, the type of lamps, radiation output of the lamps, and geometric parameters of the irradiation apparatus, and can be determined by simple manual experiments and analysis of the product stream. See US’039, col. 2, ll. 24-31. US’039 does not expressly state that the shortest distance from the light source to the flowed mixed gas is 1 m or less. However, the distance between the light source and the flowing reaction gas is an ordinary irradiation-geometry parameter affecting the intensity of light delivered to the gas stream. It would have been obvious to one of ordinary skill in the art to position the light source within 1 m of the flowed mixed gas in order to provide effective irradiation of the gas-phase reaction mixture, especially in view of US’039’s express teaching that lamp type, lamp output, and irradiation-apparatus geometry are routinely optimized by simple experimentation. See KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 417 (2007).
Accordingly, claims 1-4 are anticipated by US’039, or alternatively obvious over US’039, and obvious over US’039.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DEBORAH D CARR whose telephone number is (571)272-0637. The examiner can normally be reached Monday-Friday (10:30 am -6:30 pm).
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/DEBORAH D CARR/Primary Examiner, Art Unit 1691
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