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 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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-10 is/are rejected under 35 U.S.C. § 103 as being unpatentable over Ito et al. (US 6,720,458, hereafter “US’458”) in view of Periana eta l. (US 7,285,679, hereafter “US’679”), Choudary et al. (US 7,411,099, hereafter “US’099”), Srinivas et al. (US 7,189,882, hereafter “US’882”), and MacDonald (US 4,609,444, hereafter “US’444”).
US’458 teaches the core light-promoted oxidation process of claim 1. US’458 discloses photooxidizing methyl groups of methylbenzene and substituted methylbenzene derivatives in the presence of oxygen and a photooxidation catalyst under light irradiation to produce aldehydes. See US’458, lines 404-407, lines 424-427, lines 435-439, and claims 1 and 4-7, lines 488-510. US’458’s working examples disclose oxygen-saturated acetonitrile, methylbenzene derivative substrates, tetrafluoroterephthalonitrile catalyst, high-pressure mercury-lamp irradiation, room-temperature reaction conditions, and aldehyde products. See US’458, lines 457-470 and 475-476.
US’679 teaches oxidation of C1-C4 alkanes, including methane, ethane, and propane, to oxygen-containing organic compounds such as alcohols, aldehydes, ketones, and carboxylic acids. See US’679, lines 619-623. US’679 further claims oxidation of C1-C5 alkanes with oxygen and teaches propane as an alkane substrate. See US’679, claim 1, lines 757-758, claim 4, lines 762-763, and claim 17, line 784.
US’099 teaches liquid-phase oxidation of toluene using a catalyst containing manganese acetate, a Lewis acid, and a bromide promoter, specifically sodium bromide, in acetic acid solvent and under air pressure to form benzaldehyde, benzyl alcohol, and benzoic acid. See US’099, lines 333-337 and Example 1, lines 395-402. US’099 also discloses compressed air, oxidation temperatures of 70-140°C, lean oxygen pressure of 70-400 psig, and organic or inorganic halide promoters. See US’099, lines 376-385.
US’882 teaches liquid-phase oxidation of toluene to benzaldehyde using a catalyst system comprising transition metal/metals and a bromide source as promoter in the presence of diluted oxygen. See US’882, lines 360 and 384-388. US’882 discloses temperature and pressure ranges of 70-180°C and 1-80 bar, respectively. See US’882, lines 379-387. US’882 further discloses that the bromide promoter may be sodium bromide, hydrogen bromide, or zinc bromide. See US’882, line 390.
US’444 teaches that photochemical reactions may be carried out using radiation having a wavelength from about 100 to about 750 nm. See US’444, lines 463-465 and claim 1, lines 877-885. This range overlaps the claimed 300-800 nm range and supports the routine selection of UV/visible wavelengths for photochemical reactions.
It would have been obvious to one of ordinary skill in the art to apply US’458’s photooxidation process to the broader saturated C-H substrates taught by US’679 because US’458 and US’679 both concern oxidation of saturated carbon-hydrogen bonds to oxygenated products. US’458 teaches photooxidation of benzylic methyl C-H bonds, while US’679 teaches that lower alkanes such as methane, ethane, and propane were known oxidation substrates for producing alcohols, aldehydes, ketones, and carboxylic acids. The substitution or extension of known photooxidation conditions to known alkane oxidation substrates would have been a predictable use of known oxidation chemistry to obtain known oxygenated products.
As to claim 1, US’458 teaches light-promoted oxidation of methylbenzene derivatives in oxygen using a catalyst at room temperature to generate aldehyde oxidation products. US’679 further teaches that saturated lower alkanes are known oxidation substrates. US’099 and US’882 further establish that toluene/benzylic C-H oxidation using oxygen or air and halide/bromide promoter systems was known.
As to claim 2, US’458 teaches use of a photooxidation catalyst. US’099 and US’882 teach halide/bromide-promoted oxygen oxidation of toluene. US’882 expressly identifies hydrogen bromide as a bromide promoter, and US’099 teaches sodium bromide as an inorganic halide promoter. In view of these teachings, it would have been obvious to use hydrobromic acid or bromide/acetic acid systems as known bromide/halide promoter sources in oxidation of benzylic saturated C-H bonds. It also would have been obvious to select related hydrohalic acid or hypohalite systems, including hydrochloric acid, hydrobromic acid, tert-butyl hypochlorite, chloride/acetic acid mixtures, and bromide/acetic acid mixtures, as predictable acid/halogen sources for promoting C-H oxidation.
As to claim 3, US’679 teaches oxidation of C1-C5 alkanes and specifically identifies methane, ethane, propane, and propane embodiments. See US’679, lines 619-623, lines 757-763, and line 784. Since claim 3 recites C1-C8 alkanes, the claimed genus encompasses the lower alkanes taught by US’679.
As to claim 4, US’458 teaches photooxidation of methylbenzene and substituted methylbenzene derivatives, including substrates bearing halogen, cyano, nitro, hydroxyl, carboxyl, alkyl, alkoxy, sulfonic acid, and aldehyde substituents. See US’458, lines 412-415, 424-427, and 439. US’099 and US’882 further teach oxidation of toluene, which is a phenyl-substituted C1 alkane.
As to claim 5, the use of acidic oxidation systems and acid/halide promoter systems was known in the art. US’099 teaches use of Lewis acid and bromide promoter with acetic acid solvent, and US’882 teaches bromide promoter sources including hydrogen bromide. See US’099, lines 333-337 and 376-385; US’882, lines 384-390. Selection of oxyacids such as sulfuric acid, nitric acid, or p-toluenesulfonic acid would have been an obvious acidic promoter choice for oxidation conditions where acidity and radical/oxidation promotion are result-effective variables.
As to claim 6, US’458 teaches light irradiation using a high-pressure mercury lamp. See US’458, lines 457-470 and 475-476. US’444 teaches that photochemical reactions may use radiation from about 100 to about 750 nm, which overlaps the claimed 300-800 nm range. See US’444, lines 463-465 and claim 1, lines 877-885. Selecting a wavelength within 300-800 nm would have been routine optimization based on the absorption characteristics of the catalyst and desired reaction rate.
As to claim 7, US’458 teaches aldehyde oxidation products, US’679 teaches alcohols, aldehydes, ketones, and carboxylic acids as alkane oxidation products, and US’099/US’882 teach benzaldehyde, benzyl alcohol, and benzoic acid products in toluene oxidation. See US’458, lines 404-407 and 496-510; US’679, lines 619-623; US’099, lines 401-402 and 411; US’882, lines 381 and 386.
As to claim 8, US’458 teaches oxygen in the reaction system. See US’458, lines 435-437 and 457-470. US’099 teaches compressed air and pressure ranges of 70-400 psig, and US’882 teaches diluted oxygen at pressures of 1-80 bar. See US’099, lines 381-385 and Example 1, lines 395-402; US’882, lines 379-387. These pressures overlap or render obvious the claimed 1 atm to 100 atm pressure range.
As to claim 9, US’458 teaches a substrate-to-catalyst molar ratio within the claimed range, as Example 1 uses 30 mM p-tolunitrile and 10 mM catalyst. See US’458, lines 457-458. US’099 and US’882 further teach varying catalyst/promoter amounts relative to toluene. See US’099, lines 376-379 and 395-402; US’882, lines 389-390. Catalyst loading is a result-effective variable, and selecting a molar ratio within the broad claimed range would have been routine optimization.
As to claim 10, US’458 teaches acetonitrile as a solvent. See US’458, lines 457-458, 468-469, and 475-476. US’099 and US’882 teach acetic acid and other organic acid solvents for liquid-phase oxidation. See US’099, lines 380-381 and 395-402; US’882, lines 374-376 and 384-388. Selection of the claimed organic solvents would have been routine solvent optimization based on substrate solubility, oxygen compatibility, catalyst compatibility, and reaction efficiency.
Claim Rejections - 35 USC § 102
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) 1, 4, 7, 9-10 is/are rejected under 35 U.S.C. 102(a)(1)/(a)(2) as being anticipated by Ito et al. (US 6,720,458, hereafter “US’458”).
US’458 discloses a method of photooxidation of a substrate comprising reacting the substrate with oxygen by applying light in the presence of a halogenated aromatic nitrile photooxidation catalyst. See US’458, claim 1, Google Patents lines 488-491. US’458 further discloses that the photooxidation catalyst is used for converting a methyl group into an aldehyde group, including converting a methyl group of methyl group-substituted aromatics and methylbenzene derivatives into an aldehyde group. See US’458, lines 404-407 and claims 4-6, lines 496-502.
As to claim 1, US’458 discloses mixing a compound containing a saturated carbon-hydrogen bond with a catalyst and subjecting the compound to oxidation in the presence of oxygen under light irradiation to generate an oxidation product. US’458’s methylbenzene and substituted methylbenzene substrates contain benzylic methyl saturated carbon-hydrogen bonds. US’458 discloses that the photooxidation reaction is performed by applying light in the presence of oxygen and a photooxidation catalyst. See US’458, lines 435-437. US’458’s examples disclose acetonitrile saturated with oxygen, p-tolunitrile or o-chlorotoluene substrate, tetrafluoroterephthalonitrile catalyst, light irradiation at room temperature using a high-pressure mercury lamp, and aldehyde product formation. See US’458, Example 1, lines 457-466; Example 2, lines 468-470; and Example 4, lines 475-476. Room temperature is within the claimed 20°C to 100°C range.
As to claim 4, US’458 discloses methylbenzene and substituted methylbenzene substrates, which correspond to C1 alkane groups substituted with phenyl or substituted phenyl. US’458 expressly identifies substituents on the methylbenzene ring including chlorine, fluorine, cyano, nitro, hydroxyl, carboxyl, alkyl, alkoxy, sulfonic acid, and aldehyde groups. See US’458, lines 412-415 and lines 424-427. US’458 also lists methyl group-substituted aromatics including toluene, cresols, methylanisoles, p-toluenesulfonic acid, tolunitriles, methylbenzoic acids, halogenated methylbenzene, methyl naphthalenes, and methyl heteroaromatics. See US’458, line 439.
As to claim 7, US’458 discloses that the oxidation product is an aldehyde. See US’458, lines 404-407 and claims 4-7, lines 496-510.
As to claim 9, US’458’s Example 1 uses 30 mM p-tolunitrile and 10 mM tetrafluoroterephthalonitrile, corresponding to a substrate-to-catalyst molar ratio of 1:0.333, which falls within the claimed range of 1:0.0001 to 1:1. See US’458, lines 457-458.
As to claim 10, US’458 discloses acetonitrile saturated with oxygen as the reaction solvent. See US’458, Example 1, lines 457-458; Example 2, lines 468-469; and Example 4, lines 475-476.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1-10 rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the enablement requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to enable one skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention.
Claim 1 is directed to a method for light-promoted oxidation of “a compound containing a saturated carbon-hydrogen bond,” comprising mixing the compound with “a catalyst” and subjecting the compound to an oxidation reaction in oxygen or air at a temperature of 20°C to 100°C under light irradiation to generate an oxidation product. The claim is not limited to any particular substrate class, any particular saturated carbon-hydrogen bond environment, any particular catalyst class, any particular reaction mechanism, any particular solvent, any particular pressure except as broadly recited in dependent claim 8, or any particular oxidation product except as broadly recited in dependent claim 7.
The specification provides working examples directed to selected substrates and selected reaction systems, including selected alkylarenes or lower alkanes oxidized under particular acid/light/oxygen or air conditions. However, the disclosure does not provide sufficient guidance to enable one of ordinary skill in the art to practice the full scope of claim 1 across the entire genus of compounds containing saturated carbon-hydrogen bonds and the entire scope of “a catalyst” without undue experimentation.
The factors set forth in In re Wands support a finding of nonenablement.
First, the breadth of the claims is very large. Claim 1 covers any compound containing a saturated carbon-hydrogen bond. This includes compounds having widely different structures, functional groups, bond dissociation energies, steric environments, electronic effects, solubilities, volatilities, and oxidation susceptibilities. The claim also covers any catalyst, without limiting the catalyst to the disclosed acids, hypohalites, hydrohalic acids, or in situ hydrohalic-acid-generating mixtures. The breadth of the claim is therefore substantially broader than the working examples and guidance provided in the specification.
Second, the nature of the invention is unpredictable. Selective oxidation of saturated carbon-hydrogen bonds is highly dependent on substrate structure, the strength and accessibility of the carbon-hydrogen bond, radical stability, oxygen incorporation, catalyst compatibility, solvent effects, light wavelength, oxygen pressure, temperature, and competing side reactions. A reaction condition that oxidizes one substrate may fail with another substrate, may produce different products, or may result in overoxidation, decomposition, or poor selectivity. This unpredictability weighs against enablement of the full genus.
Third, the amount of direction or guidance provided in the specification is insufficient relative to the full scope claimed. The specification identifies certain preferred catalysts and certain preferred reaction conditions, but it does not provide a general predictive rule that would allow one of ordinary skill to determine which catalysts and conditions will successfully oxidize the full range of compounds containing saturated carbon-hydrogen bonds. The specification also does not adequately explain how to select catalyst identity, catalyst loading, solvent, light wavelength, pressure, temperature, and reaction time across the broad range of substrates encompassed by claim 1.
Fourth, the working examples are not commensurate in scope with the claims. The examples demonstrate selected embodiments, but they do not represent the full range of substrate classes and catalyst classes encompassed by claim 1. The examples do not establish that the claimed method operates broadly for all compounds containing saturated carbon-hydrogen bonds or for all catalysts covered by the claim. The number and variety of working examples are insufficient to support enablement of the full claimed genus.
Fifth, the state of the prior art does not cure the deficiency. Although light-promoted and aerobic oxidation reactions were known, the prior art also reflects that carbon-hydrogen bond oxidation is substrate-dependent and condition-dependent. Knowledge that some saturated carbon-hydrogen bonds can be oxidized under certain light/oxygen/catalyst conditions does not enable the full scope of claim 1, which encompasses any compound containing a saturated carbon-hydrogen bond and any catalyst.
Sixth, the relative skill in the art is high, but even a skilled artisan would still need to engage in substantial experimentation to practice the full scope of the claim. A person of ordinary skill may be able to practice the disclosed examples and make routine adjustments for closely related substrates. However, the claim extends far beyond closely related substrates and encompasses chemically diverse compounds and undefined catalyst systems. The level of skill in the art therefore does not eliminate the need for undue experimentation.
Seventh, the predictability of the art is low. Carbon-hydrogen oxidation reactions are sensitive to small structural and reaction-condition changes. Product distribution can vary significantly depending on substrate, catalyst, oxygen pressure, solvent, wavelength, and temperature. The broad claim scope requires successful oxidation across a wide and unpredictable chemical field without sufficient guidance in the specification.
Eighth, the quantity of experimentation required would be extensive. To practice the full scope of claim 1, one of ordinary skill would need to screen numerous substrate classes, catalysts, solvents, light sources, wavelengths, oxygen or air pressures, temperatures, reaction times, and concentrations to identify operable combinations and desired oxidation products. Such experimentation would go beyond routine optimization because the specification does not provide sufficient guidance for predicting which combinations will work across the full claim scope.
Accordingly, considering the Wands factors as a whole, the specification does not enable the full scope of claim 1 without undue experimentation.
Claims 2-10 are rejected because they depend from claim 1 and do not cure the enablement deficiency for the full breadth of the claimed method. Although the dependent claims narrow certain features, they still rely on the broad method of claim 1 and do not provide sufficient limitation to render the full claimed scope enabled.
Claims 1-10 rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
To satisfy the written description requirement, the specification must reasonably convey to one of ordinary skill in the art that the inventor had possession of the claimed invention as of the effective filing date. Claim 1 broadly encompasses light-promoted oxidation of any compound containing a saturated carbon-hydrogen bond using a catalyst in oxygen or air at 20°C to 100°C under light irradiation to generate an oxidation product.
The specification does not reasonably convey possession of that full genus. The disclosure identifies selected catalysts and selected substrate classes and provides working examples for particular reactions, but it does not describe a representative number of species sufficient to support the full scope of “a compound containing a saturated carbon-hydrogen bond.” The specification also does not describe common structural or functional features that would allow one of ordinary skill in the art to recognize which compounds and catalysts across the full scope of claim 1 would successfully undergo the claimed light-promoted oxidation.
The written description deficiency is particularly evident because the claim is not limited to the specific catalysts described in the specification or to the preferred substrate classes recited in dependent claims. Instead, claim 1 covers any catalyst and any compound containing a saturated carbon-hydrogen bond. The disclosure of selected acid-promoted or halogen-related embodiments does not demonstrate possession of all catalyst/substrate combinations encompassed by claim 1.
Accordingly, claim 1 lack adequate written description support. Claims 2-10 are rejected because they depend from claim 1 and do not cure the written-description deficiency for the full breadth of the claimed method.
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 1-10 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 “a catalyst” without identifying the catalyst by structure, class, function, or property. The term “catalyst,” as used in claim 1, renders the scope of the claim indefinite because the specification uses the term broadly to include materials such as hydrochloric acid, hydrobromic acid, tert-butyl hypochlorite, oxyacids, and mixtures capable of generating hydrochloric acid or hydrobromic acid in situ. These materials may function differently in the disclosed reactions, including as acid promoters, halogen sources, radical-generating species, or reactive components. Because claim 1 merely recites “a catalyst” without limiting the catalyst to any identifiable class or operative function, one of ordinary skill in the art would not be able to determine the metes and bounds of the catalyst limitation with reasonable certainty.
Claim 2 further illustrates the ambiguity by reciting specific materials as “catalyst,” including tert-butyl hypochlorite, hydrochloric acid, hydrobromic acid, and mixtures capable of in situ generating hydrochloric acid or hydrobromic acid. The claim does not make clear whether the term “catalyst” requires the material to be regenerated, not consumed, or merely present in an amount that promotes oxidation. Thus, the scope of claim 1, and the dependent claims relying on that term, is unclear.
Claim 4 is rejected because the substituent list is unclear. Claim 4 recites that the compound containing the saturated carbon-hydrogen bond is a C1-C8 alkane substituted with phenyl, biphenyl, or substituted phenyl, wherein a substituent of the substituted phenyl is selected from halogen, nitro, cyano, hydroxyl, amino, carboxyl, C2-C8 carboxylic ester group, and a displayed chemical group. The claim does not clearly identify the final recited substituent group in words, and the relationship between the displayed structure and the substituted phenyl group is unclear. As a result, one of ordinary skill in the art would not be able to determine with reasonable certainty the full scope of the substituted phenyl compounds encompassed by claim 4.
Claim 7 is rejected because the phrase “the oxidation product is at least one of alcohol, peroxyalcohol, aldehyde, ketone, carboxylic acid or peroxyacid” does not clearly define whether the claimed method requires formation of a recoverable product, a predominant product, any detectable amount of the listed product, or merely any transient or byproduct amount. In view of the breadth of claim 1 and the unpredictable nature of C-H oxidation product mixtures, the claim does not provide reasonable certainty as to when the method satisfies the oxidation-product limitation.
Claim 8 is not rejected merely for use of the unit “atm.” The term “atm” is a commonly understood pressure unit and, by itself, does not render the claim indefinite under U.S. practice.
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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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Renee Claytor can be reached at 572-272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DEBORAH D CARR/Primary Examiner, Art Unit 1691
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