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 .
DETAILED ACTION
This Office action is responsive to Applicant's Transmittal of New Application filed Dec. 12, 2024. As filed, claims 18-37 are pending. Claims 1-17 are canceled.
Priority
This application, filed 12/12/2024 is a Divisional of 17157173, filed 01/25/2021, now U.S. Patent Nr. 12187670;17157173 Claims Priority from Provisional Application 62965513, filed 01/24/2020.
Information Disclosure Statement
No information disclosure statement (IDS)has been filed in the instant application. Applicants are reminded of the duty to disclose anything believed to be material to the patentability of the instant application in accordance with 37 CPR 1.56.
Claim Objections
Claim 37 is objected to because of the following informalities: claim 37 lacks end period.
Appropriate correction is required.
Specification
The abstract of the disclosure is objected to because is not descriptive of the disclosure. Specifically, the phrase: “Oxidizing a first aromatic compound in the presence of a metal salt to yield a second aromatic compound includes combining the first aromatic compound, the metal salt, and water to yield an aqueous mixture, and heating the aqueous mixture at a temperature exceeding 200° C to yield a reaction product that includes the second aromatic compound.” is not related of the claimed invention which is drawn to a method of reducing a first aromatic compound.
Applicant is reminded of the proper content of an abstract of the disclosure.
See MPEP § 608.01(b). Correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 21 recites the limitation " the second aromatic compound comprises benzene, phenol, or both” which renders the scope of claim 21 indefinite because the phrase is self-contradictory. Hawley’s Condensed Chemical Dictionary (11th Ed., Sax, N. I. and Lewis, R. J. (editors), Van Nostrand Reinhold Co. (NY), 1987, p. 302, (emphasis added)) defines compound as:
A substance of atoms or ions of two or more elements in chemical combination. The constituents are united by bonds or valence forces. A compound, a homogeneous entity where the elements have definite proportions by weight and are represented by a chemical formula. . .
The transitional term “compound comprising” is synonymous with including, containing, and characterized by. The word “comprising” is inclusive or open-ended and does not exclude additional elements or method steps that are not recited in the claim. Genentech, Inc. v. Chiron Corp., 112 F.3d 495, 501 (Fed. Cir. 1997) (“Comprising” is a term of art used in claim language which means that the named elements are essential, but other elements may be added and still form a construct within the scope of the claim.); Moleculon Research Corp. v. CBS, Inc., 793 F.2d 1261, 229 USPQ 805 (Fed. Cir. 1986); In re Baxter, 656 F.2d 679, 686, 210 USPQ 795, 803 (CCPA 1981); Ex parte Davis, 80 USPQ 448, 450 (Bd. App. 1948) (“comprising” leaves “the claim open for the inclusion of unspecified ingredients even in major amounts”).
Therefore, a contradiction arises in the claim because a compound requires a definite chemical structure or formula therefor the claimed “compound comprises benzene, phenol, or both” renders the scope of the claim indefinite.
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.
Claims 18-22, 32, 33 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by JP 0601658, 1994 by Ishida et al. (“the ‘659 publication”; cited in PTO-892 attached herewith). The 659 publication teaches conversion of aryl halide in water to aryl hydroxide over a catalyst containing metals as a catalyst. The aryl halide substrates include chlorotoluene converted to hydroxytoluene mediated by catalyst containing copper; the reaction temperature in the present invention is usually 250-600 ℃- which corresponds to method steps as claimed (abstract; examples; instant claims 18-21, 33, 36).
[Comparative Example 2] shows reacting water / chlorobenzene (molar ratio) = 4.0, WHSV (chlorobenzene criteria) = 1.0hr-1, reaction temperature = 450 ℃, atmospheric pressure. Result of the reaction for 3-4 hours was a phenol selectivity of = 99% (instant claims 21, 33).
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Therefore, the prior art teaches the limitations of instant claims.
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 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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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 18-37 are rejected under 35 U.S.C. 103 as being unpatentable over Yang et al Organic Letters (2011), 13(16), 4340-4343 (cited in PTO-892 attached herewith).
Instant claims are drawn to a method of reducing a first aromatic compound in the presence of a metal to yield a second aromatic compound, the method comprising: combining the first aromatic compound, the metal, and water to yield an aqueous mixture; and heating the aqueous mixture at a temperature exceeding 200° C. to yield a reaction product comprising the second aromatic compound, wherein the first aromatic compound is halogenated; the second aromatic compound is dehalogenated; the first aromatic compound is chlorobenzene and the second aromatic compound comprises benzene, phenol, or both. The article by Yang teaches a highly direct efficient synthesis of phenols which corresponds to the second aromatic compounds of claimed method by copper-catalyzed hydroxylation of aryl iodides, bromides, and chlorides which corresponds to the claimed first aromatic compound. The inexpensive catalytic system showed great functional group tolerance and excellent selectivity
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(abstract).
Regarding instant claims 18-23, 26, 31-33, 35-37, the article by Yang teaches on schemes 1- 3 on page 4342 reaction of aryl chlorides including chlorobenzene, halogenated toluene, choronaphthalene mediated by copper catalyst, in water, under argon atmosphere, while heating to produce the corresponding phenols including hydroxytoluene, choro naphthalene, in good to excellent yields. 2-Chloronaphthalene was also converted into the corresponding naphthol under these conditions (6e). Additionally, steric hindrance has no influence on the coupling reaction (6f vs 6g). All of these results demonstrated the high efficiency of the CuBr/L5 catalyst system for the conversion of aryl
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Regarding instant claim 25, disclosed on table 2, page 4343 is the reaction time of 24-36h, 12h.
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Regarding insta claims 22-24, 26-31, 34, the general procedures are listed in the supporting information of the article by Yang, describing the reaction conducted in a flask- glass reaction vessel, under argon atmosphere:
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The instant claims differ from the prior art in that the article by Yang teaches the reaction of halogenated aryl substrates to phenols at temperature of 100-120 C, at atmospheric pressure and reaction times of up to 32h, while instant claims
With respect to the limitation of claims “heating the aqueous mixture at a temperature exceeding 200 ºC, since the article by Yang teaches reaction temperature of 100-120 ºC, and since temperature is a result-effective variable in the oxidation of benzene reaction, the skilled artisan would have been motivated to modify the reaction conditions such as time, temperature as part of routine optimization in attempting to obtain the highest product yield in the shortest amount of time. In other words, it is inherent that a person of ordinary skill in art would be motivated to optimize a reaction by varying experimental parameters in search of optimal conditions. See MPEP 2144.05 II.A:
“[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955)
Regarding the pressure and reaction time, the prior art teaches reaction time of 2h, at normal pressure the determination of the appropriate reaction time and pressure as an art recognized result-effective variables, is subject to routine optimization in the course of modification of the process of the prior art.
Moreover, the normal desire of scientists or artisans to improve upon what is already generally known provides the motivation to determine where in a disclosed set of percentage ranges is the optimum combination of percentages. See In re Boesch, 617 F.2d 272, 276 (CCPA 1980) (“[Discovery of an optimum value of a result effective variable in a known process is ordinarily within the skill of the art.” In re Peterson, 315 F.3d 1325, 1329 (Fed. Cir. 2003). See MPEP 2144.05.
Therefore, in view of the teachings and suggestions from the article by Yang, it 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 to modified the reaction condition of the process of prior art by conducting the reaction at various parameters – temperature, pressure, time, thereby arriving at the instantly claimed process merely by the normal course of research and development for the reasons outlined above, with reasonable expectation of success and thereby rendering the instant claims obvious.
Pertaining to the temperature, time, pressure of a process, it is noted that generally, differences such parameters will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such parameter is critical. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) See MPEP 2144.5.
The instantly claimed process therefore corresponds to the combination of prior art elements according to known methods to yield predictable results. There would have been a reasonable expectation for success since each element retains its intended function in the combination.
Absent factual unexpected, unobvious, and beneficial results, the claimed invention would have been suggested to one skilled in the art and therefore, the instant claimed invention would have been obvious to one skilled in the art.
Conclusion
Claims 18-37 are rejected.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANA MURESAN whose telephone number is (571)-270-7587. The examiner can normally be reached on Monday through Friday, 8:30 am to 5:30 pm EST.
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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/ANA Z MURESAN/Primary Examiner, Art Unit 1692
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