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 2 – 13 and 15 – 21 in the reply filed on May 21, 2026 is acknowledged. The traversal is on the ground(s) that the claims as amended all read on the invention of Group II. This is found persuasive.
Status of Claims
Claims 2 – 13 and 15 – 21 are pending.
Claims 1 and 14 have been cancelled.
Claims 2 – 13 and 15 – 21 are rejected.
Claim 17 is objected.
Claim Objections
Claim 17 is objected to because of the following informalities: the sentence ends with a partial parenthesis [)] before the period.. 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.
Claims 3, 4, 5, 6, 8 and 18 – 21 are rejected under 35 U.S.C. 112(b), 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.
Regarding claims 3, 4, 5, 8, 18,20 and 21, the phrases "for example" or “such as’ renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
Claims 6 and 19 are rejected for being dependent upon a rejected base claim.
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.
Claims 2 – 13 and 15 – 21 are rejected under 35 U.S.C. 112(a), because the specification, while being enabling for preparing an alcohol or carbonyl compound from an hydrocarbon of terpene or terpenoid using ozone wherein in step (1) the hydrocarbon of terpene or terpenoid are dissolved or suspended in an alkaline aqueous solution or emulsion, does not reasonably provide enablement for the method wherein the alkane is any alkane according to IUPAC Compendium of Chemical Terminology. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention commensurate in scope with these claims.
The test for enablement is whether one skilled in the art could make and use the claimed invention from the disclosures in the specification coupled with information known in the art without undue experimentation (United States v. Telectronice, 8, USPQ2D 1217 (Fed. Cir, 1988). Whether undue experimentation is needed is not based upon a single factor but rather in a conclusion reached by weighing many factors. The factors to be considered in determining whether a disclosure meets the enablement requirements of 35 U.S.C. 112, first paragraph, have been described in In re Wands, 858 F.2d 731, 8 USPQ2d 1400 (Fed. Cir., 1988). The court in Wands states, “Enablement is not precluded by the necessity for some experimentation, such as routine screening. However, experimentation needed to practice the invention must not be undue experimentation. The key word is ‘undue’, not ‘experimentation’” (Wands, 8 USPQ2sd 1404). Clearly, enablement of a claimed invention cannot be predicated on the basis of quantity of experimentation required to make or use the invention. “Whether undue experimentation is needed is not a single, simple factual determination, but rather is a conclusion reached by weighing many factual considerations” (Wands, 8 USPQ2d 1404). Among these factors are: (1) the nature of the invention; (2) the breadth of the claims; (3) the state of the prior art; (4) the predictability or unpredictability of the art; (5) the relative skill of those in the art; (6) the amount of direction or guidance presented; (7) the presence or absence of working examples; and (8) the quantity of experimentation necessary.
While all of these factors are considered, a sufficient amount for a prima facie case is discussed below.
(1) The nature of the invention and (2) the scope of the claims:
The nature of the claims are drawn to a method of preparing an alcohol or carbonyl compound from an alkane using ozone, comprising the steps of (1) exposing the alkane to ozone, and (2) isolating or purifying the resulting alcohol or carbonyl product; wherein in step (1) the alkane is dissolved or suspended in an alkaline aqueous solution or emulsion.
The scope of the invention in the claims is such that any alkane according to IUPAC Compendium of Chemical Terminology. Further, according to the disclosure’s definition of alkane this includes any “alkane” having at least one alkyl group and can comprise any other structural elements, double bond, triple bond or aromatic rings.
Additonally, according to the scope of claim 7, preparing a carbonyl compound from an alkane, comprising the steps of (1) exposing the alkane to ozone to form an alcohol according to claim 2, (2) reacting the alcohol with an acid to yield an alkene, (3) exposing the resulting alkene to ozone to yield a secondary ozonide, (d) oxidatively or reductively decomposing the secondary ozonide to yield one or more carbonyl compounds, and (e) isolating or purifying one or more of said carbonyl compounds.
(3) The state of the prior art: Chantal et al. (EP0459861) discloses a process for the oxidation of alkanes or cyclanes has now been found, and even more broadly a process for the oxidative activation of C-H bonds whose carbon atom is in the sp³ hybridization state in a hydrocarbon, by the action of hydrogen peroxide on the hydrocarbon in the presence of a catalyst, which does not use superacids, makes it possible to dispense with a solvent as well as a co-surfactant, and results in a selectivity of the activation of the C-H bond in alcohol and/or ketone. (pp.2, [0008]). Examples of hydrocarbons to which the process of the Chantal invention applies include octane, cyclooctane, decahydronaphthalene or decalin, ethylbenzene, isopropyl benzene or cumene, and tetrahydro-1,2,3,4 naphthalene or tetraline. (pp. 8, [0016]).
Dillemuth et al. discusses the reaction of ozone with methane. (Journal of Physical Chemistry, 1960). Methane being the simplest hydrocarbon and a saturated alkane. The abstract discloses:
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Also, in the experimental results, the infrared adsorption spectra of he products of the reaction showed principally, carbon monoxide, carbon dioxide, formic acid and water. Formaldehyde was not detected n any of the infrared spectra. (pp. 1497, left col. (a)).
Toby et al. discusses reactivity of the ozone-ethane system. (Journal of Physical Chemistry, 1998). The abstract discloses:
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Toby concluded that ethane and ozone react at room temperature. There is no evidence for a molecular reaction (as is the case for virtually all low-temperature alkane oxidations), but radical concentrations build up and a chain reaction then occurs. Added oxygen scavenges the radicals and slows the buildup, causing remarkable induction periods that can be several hours long. The highly oxygen-inhibited induction periods in the O3-C2H6 system depend on a catalyst for ozone decomposition. (pp. 4531).
Timerghazin et al. presents a theoretical study of the reaction between ozone and C-H bond: gas-phase reactions of hydrocarbons with ozone. (Journal of Molecular Structure, 1999). The abstract discloses:
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(4) the predictability or unpredictability of the art:
Chemistry is unpredictable. In re Marzocchi, 439 F2d 220, 169 USPQ 367 para. 3. However, the "predictability or lack thereof” in the art refers to the ability of one skilled in the art to extrapolate the disclosed or know results to the claimed invention. If one skilled in the art can readily anticipate the effect of a change within the subject matter to which the claimed invention pertains, then there is predictability in the art. MPEP 2164.03.
With regard to the predictability of Applicant’s method of preparing a carbonyl compound from an alkane using ozone, when the alkane is methane, ethane, propane or isobutane base on Timerghazin is highly unpredictable.
(5) The relative skill of those in the art: One of ordinary skill is a practicing organic chemist.
(6) The amount of direction or guidance presented and (7) the presence or absence of working examples:
The specification has provided guidance for preparing an alcohol or carbonyl compound from an hydrocarbon of terpene or terpenoid using ozone wherein in step (1) the hydrocarbon of terpene or terpenoid are dissolved or suspended in an alkaline aqueous solution or emulsion.
However, the specification does not provide guidance for method wherein the alkane is any alkane according to IUPAC Compendium of Chemical Terminology; any “alkane” having at least one alkyl group and can comprise any other structural elements, double bond, triple bond or aromatic rings.
(8) The quantity of experimentation necessary:
Considering the state of the art as discussed by the references above, particularly with regards to teaching of the prior art and the high unpredictability in the art as evidenced therein, and the lack of guidance provided in the specification, one of ordinary skill in the art would be burdened with undue experimentation to practice the invention commensurate in the scope of the 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 (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.
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.
Claim(s) 2, 9 – 12, 17, 18, 19, 20 and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Menyailo et al. (US 3,664,810).
The rejected claim covers, inter alia, a method of preparing an alcohol or carbonyl compound from an alkane using ozone, comprising the steps of (1) exposing the alkane to ozone, and (2) isolating or purifying the resulting alcohol or carbonyl product; wherein in step (1) the alkane is dissolved or suspended in an alkaline aqueous solution or emulsion.
Dependent claim 9 further limits the alkaline aqueous solution to an inorganic base. Dependent claim 10 further limits the inorganic base to an alkoxide, hydroxide, oxide, carbonate or bicarbonate of an alkali or alkaline earth metal. Dependent claim 11 further limits the method to not having a catalyst. Dependent claim 17 further limits the method by limiting the alkane to being dissolved in an aqueous solution of an alkoxide, hydroxide, oxide, carbonate or bicarbonate of an alkali or alkaline earth metal. Dependent claim 18 further limits the method by limiting the alkane to being dissolved in an aqueous solution of a sodium, potassium, lithium, calcium or magnesium hydroxide, alkoxide, oxide, carbonate or bicarbonate (e.g., sodium hydroxide or potassium hydroxide). Dependent claim 19 further limits the aqueous solution to having a pH from 7.5 to 12, or from 8 to 12, or from 9 to 11, or from 9 to 10. Dependent claim 20 further limits the method by the addition of an aqueous solvent. Dependent claim 21 further limits the method to continuous flow.
During patent examination, the pending claims must be "given their broadest reasonable interpretation consistent with the specification." In re Hyatt, 211 F.3d 1367, 1372, 54 USPQ2d 1664, 1667 (Fed. Cir. 2000). Claim terms are presumed to have the ordinary and customary meanings attributed to them by those of ordinary skill in the art. Sunrace Roots Enter. Co. v. SRAM Corp., 336 F.3d 1298, 1302, 67 USPQ2d 1438, 1441 (Fed. Cir. 2003); Brookhill-Wilk 1, LLC v. Intuitive Surgical, Inc., 334 F.3d 1294, 1298 67 USPQ2d 1132, 1136 (Fed. Cir. 2003). In this instance Applicant chose to define an “alkane” as only required to have at least one alkyl group and can comprise any other structural elements, double bond, triple bond or aromatic rings. Therefore, this rejection alkane is being interpreted as such.
However, Menyailo disclose a process for ozonizing unsaturated compounds to form carbonyl compounds and inorganic peroxides. Specifically, Menyailo discloses
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(col. 1, abstract)
At completion of the ozonization reaction the carbonyl (i.e. aldehyde or ketone) is isolated and purified. (Examples 1 – 8). The reaction is caried out at -30°C and under atmosphere pressure. The aqueous-organic medium can be water-acetone or water-heptane. (col. 1,ln 66 – 69). The alkaline earth metal hydroxides employed are Mg(OH)2, Ca(OH)2, Sr(OH)2 and Ba(OH)2. (col. 2, ln 3 – 8). There is no teaching of the addition or presence of a catalyst. (Examples 1 – 8). Ozone is the only oxidizing agent present. (Examples 1 – 8). The alkaline earth metal hydroxide in a aqueous medium has pH ranging from 10.5 (Mg(OH)2) to 14 (Ba(OH)2). (general knowledge). The unsaturated hydrocarbons are dissolved in an aqueous or aqueous organic medium as a co-solvent). (col. 1, ln 66 – 67). The process can be carried out continuously. (col. 1, ln 69 – 70).
The difference between Menyailo and the claimed invention is that they do not teach the invention with particularity so as to amount to anticipation (See M.P.E.P. §2131: "[t]he identical invention must be shown in as complete detail as is contained in the ...claim." Richardson v. Suzuki Motor Co., 868 F.2d 1226, 1236, 9 USPQ2d 1913, 1920 (Fed. Cir. 1989). The elements must be arranged as required by the claim, but this is not an ipsissimis verbis test, i.e., identity of terminology is not required. In re Bond, 910 F.2d 831, 15 USPQ2d 1566 (Fed. Cir. 1990).).
However, based on the above, Menyailo teaches the elements of the claimed invention with sufficient guidance, particularity, and with a reasonable expectation of success, that the invention would be prima facie obvious to one of ordinary skill (the prior art reference teaches or suggests all the claim limitations with a reasonable expectation of success. (see M.P.E.P. § 2143).
Art Made of Record
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Varkony et al. (J.C.S. Chem. Comm., 1974) discloses reactions of ozone with saturated hydrocarbons. Dishman Pharmaceuticals and Chemicals, LTD. (WO2010/011134) discloses the preparation of Nopinone from beta-pinene with ozone. (Example 2).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to YATE' K. CUTLIFF whose telephone number is (571)272-9067. The examiner can normally be reached Monday-Friday (8:30 - 5:30).
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/YATE' K CUTLIFF/Primary Examiner, Art Unit 1692
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