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 .
Response to Arguments
Applicant’s arguments, see pages 4-7, filed 19 May 2026, with respect to the rejection(s) of claim(s) 1-20 under 35USC§102, 35USC§103, and 35USC§112 have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of CN102757302 in view of Grane , 35 USC§112(a), 35USC§112(b).
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.
Claims 1–4, 9–12, 14, 22–25, and 27 is/are rejected under 35 U.S.C. § 103 as being unpatentable over CN 102757302A (“CN”) in view of Grane, U.S. Patent No. 3,478,108 (“Grane”).
Claim 1
CN discloses a process for oxidizing isobutane by contacting isobutane with an ozone-containing gas under oxidation conditions. Isobutane is an alkane having a tertiary carbon. CN further discloses production of tert-butyl alcohol, the hydroxylate corresponding to isobutane. See CN, Abstract; claim 1; pp. 3 and 6–9, ¶¶ [0010], [0014], [0038]–[0039], [0044]–[0045], [0054]–[0055], and [0064]–[0065].
CN discloses that ozone may be supplied as pure ozone or as a mixture with oxygen, air, nitrogen, helium, carbon dioxide, or another diluent. Oxygen and air are identified as the most preferred diluents. CN also teaches controlling ozone concentration to control the severity of the reaction and discloses ozone concentrations of at least 1 volume percent, including 5 volume percent. See CN, pp. 3–4, ¶¶ [0015]–[0017]; claims 2–4; and p. 6, ¶¶ [0044]–[0045]. CN’s oxygen- and air-based embodiments are free of added CO₂. See CN, pp. 6–7, ¶¶ [0038], [0041], [0044], and [0054].
CN further discloses that the reaction may be conducted in the presence of water or an alcohol, including methanol and ethanol. CN states that use of solvent is preferred to make the reaction system homogeneous, but the basic process of CN claim 1 and paragraph [0014] does not require a solvent. See CN, pp. 4–5, ¶¶ [0023]–[0025], and pp. 6–9, ¶¶ [0041], [0054], [0067]–[0068], and [0088]–[0089]. CN does not expressly disclose that the protic additive constitutes 0.2–5 volume percent of the liquid-phase medium with the balance being the alkane.
Grane discloses liquid-phase oxidation of isobutane to produce tert-butyl alcohol and tert-butyl hydroperoxide, wherein water is added to control conversion and product selectivity. Grane teaches adding sufficient water to provide at least about 2 weight percent water, preferably no more than about 3 weight percent, with an upper limit of approximately 6 weight percent while maintaining the water miscible in the reaction mixture. See Grane, Abstract; col. 1, ll. 43–64; and claim 1, col. 3, l. 29 through col. 4, l. 4.
Grane further teaches that best results are obtained when the hydrocarbon feed contains at least 90 weight percent isobutane and that other hydrocarbon diluents are optional. Oxygen-containing gas is bubbled through the liquid isobutane. See Grane, col. 2, ll. 1–16. Thus, Grane expressly teaches an isobutane-rich liquid medium containing only a minor amount of added water, rather than a bulk-solvent system.
Grane’s batch example compares oxidation of isobutane with and without 5.4 percent added water and reports that water increases conversion and alters selectivity. See col. 2, ll. 29–58. Grane’s continuous example adds water directly to the isobutane feed and reports water levels of 1–6 weight percent in the reactor, with increased isobutane conversion at the lower water levels. See col. 2, ll. 61–70; col. 3, ll. 1–18; and the table bridging columns 3 and 4.
It would have been obvious to conduct CN’s ozone oxidation of isobutane using the isobutane-rich, minor-water liquid medium taught by Grane. Both references concern liquid-phase oxidation of the same substrate to tert-butyl alcohol and peroxide products. Grane expressly identifies water concentration as a process variable affecting conversion and selectivity and teaches an alkane-rich medium in which additional hydrocarbon diluents are optional. Applying Grane’s known water-control technique to CN’s ozone oxidation process would have been a predictable use of a known process technique for the same substrate and corresponding oxidation products.
The rejection does not depend on treating weight percent and volume percent as identical units. Grane establishes that a low, narrowly controlled water concentration is a result-effective variable in an isobutane-rich liquid oxidation system. It would have been within ordinary skill to express the concentration in volume percent and determine a workable amount within the claimed 0.2–5 volume percent range through routine process adjustment. Optimization is ordinarily obvious where the prior art recognizes the parameter as affecting the desired result.
CN and Grane also do not require added CO₂. CN’s preferred ozone diluents are oxygen or air, and Grane uses air. The combined process therefore would have been free of added CO₂.
Claim 2
Claim 2 further requires adding the protic additive to the liquid-phase medium before oxidizing the alkane. Grane teaches adding water to the isobutane reaction mixture and, in its continuous example, adding water directly to the isobutane feed supplied to the reaction zone. See Grane, col. 2, ll. 61–70 and col. 3, ll. 1–8. It would have been obvious to add water before or as the isobutane enters the reaction zone so that the selected water concentration is present when oxidation begins.
Claims 3 and 4
Claim 3 requires that the protic additive be water, an alcohol, or a combination thereof. Claim 4 requires water. CN identifies water, methanol, and ethanol as suitable protic solvents. See CN, pp. 4–5, ¶¶ [0023]–[0025], and Examples 2, 6, 8, 10, and 17. Grane expressly teaches added water as the minor component used to control isobutane oxidation. See Grane, col. 1, ll. 43–64.
Claims 9–11
Claim 9 requires a C4–C20 alkane. Claim 10 requires a branched alkane. Claim 11 requires isobutane.
CN and Grane each expressly disclose isobutane. Isobutane is a branched C4 alkane having a tertiary carbon and therefore satisfies each limitation. See CN, Abstract and claim 1; Grane, Abstract and col. 1, ll. 43–51.
Claim 12
Claim 12 requires a reaction temperature of at least 15°C and a total vapor-phase pressure of no more than 5 MPa. CN discloses reaction temperatures of 0–180°C and pressures of 0.1–3 MPa, including preferred temperatures of 20–160°C and preferred pressures of 0.3–2.5 MPa. Specific examples are conducted at 20°C and 1.5 MPa, 40°C and 0.1 MPa, 50°C and 1.0 MPa, and 80°C and 0.2 MPa. See CN, p. 5, ¶ [0026], and pp. 6–7, ¶¶ [0038], [0041], [0044], and [0054]. These disclosed conditions fall within the claimed ranges.
Claim 14
Claim 14 requires an ozone mole fraction of 1–5 percent in the feed-gas mixture.
CN discloses an ozone-containing mixed gas having at least 1 volume percent ozone and specifically discloses a gas mixture containing 5 volume percent ozone. See CN, claims 3–4; pp. 3–4, ¶¶ [0016]–[0017]; and p. 6, ¶¶ [0044]–[0045]. For a gas mixture at common temperature and pressure, the disclosed volume fraction corresponds to mole fraction.
Claims 22–25 and 27
Claim 22 requires, to the extent reasonably understood, that no additional bulk liquid solvent or catalyst be included in the alkane/protic-additive liquid charge. Grane teaches an isobutane-rich liquid reaction medium containing a minor amount of added water. The hydrocarbon feed preferably contains at least 90 weight percent isobutane, and other hydrocarbon diluents are optional. See Grane, col. 1, ll. 43–64 and col. 2, ll. 1–6. CN does not require a catalyst or bulk solvent in its general ozone oxidation process. See CN, claim 1 and ¶¶ [0010]–[0014].
Claim 23 limits the alkane to C4–C8. Isobutane is a C4 alkane. Claim 24 limits the protic additive to water, as expressly taught by Grane. Claim 25 limits the alkane to isobutane, as expressly taught by both references. Claim 27 repeats the water limitation already present through claims 24 and 25 and is met for the same reasons.
Response to Applicant’s Arguments
Applicant argues that CN is limited to a solvent-dominated reaction environment because paragraph [0023] discloses an isobutane-to-solvent molar ratio of 1:1–150 and the examples use solvent in excess. Applicant further argues that there would have been no reason to omit CN’s bulk solvent and use an alkane-rich medium containing only 0.2–5 volume percent protic additive.
The arguments are not persuasive. CN’s 1:1–150 ratio applies to its preferred solvent embodiments. CN’s basic process, set forth in claim 1 and paragraphs [0010] and [0014], requires contacting isobutane with ozone-containing gas but does not require solvent. Paragraph [0023] expressly characterizes solvent use as preferred. CN therefore does not require that solvent provide the continuous phase and does not criticize or exclude an alkane-rich reaction medium.
Grane is not relied upon merely for the general proposition that water may be added. Grane directly teaches the missing reaction-medium arrangement: at least 90 weight percent isobutane, optional hydrocarbon diluent, and a controlled minor amount of water that affects conversion and selectivity. See Grane, col. 1, ll. 43–64; col. 2, ll. 1–6 and 29–58; and col. 3, ll. 1–18. The proposed combination applies Grane’s alkane-rich, minor-water medium to CN’s ozone oxidation process; it does not retain CN’s solvent-rich examples.
Applicant also relies on the proposed stabilization of a hydrotrioxide intermediate and improved ozone utilization. The argument does not establish nonobviousness of claim 1. Claim 1 does not require a particular mechanism, minimum hydroxylate selectivity, or minimum ozone-utilization value. Further, the remarks do not provide comparative evidence establishing an unexpected result over the closest combined teachings of CN and Grane throughout the full claimed alkane and protic-additive scope.
The amendments therefore overcome the anticipation rejection based on CN alone, but they do not overcome the obviousness rejection based on CN in view of Grane.
Claims 26, 28, and 29
Claims 26, 28, and 29 is/are rejected under 35 U.S.C. § 103 as being unpatentable over CN in view of Grane, as applied above, and further in view of Barone, U.S. Patent No. 3,873,625 (“Barone”).
CN and Grane render obvious the ozone oxidation process, the alkane-rich liquid medium, the minor protic-additive concentration, and the use of water, as discussed above. Neither reference expressly identifies a C5–C20 or C5–C8 tertiary alkane.
Barone discloses liquid-phase oxidation of tertiary alkanes and teaches that suitable tertiary alkanes contain 3–30 carbon atoms, preferably 4–10 carbon atoms, and most preferably 5–8 carbon atoms. Barone expressly identifies isopentane, 2-methylpentane, 3-methylhexane, 2,3-dimethylhexane, 4-methylheptane, and higher tertiary alkanes. See Barone, col. 2, ll. 15–31.
Barone further identifies isopentane, isohexane, isoheptane, and isooctane as particularly preferred substrates and teaches that the tertiary carbon is the most reactive site in the oxidation. See col. 2, ll. 49–54 and col. 3, ll. 1–23.
It would have been obvious to substitute one of Barone’s known C5–C8 tertiary alkanes for the isobutane used by CN and Grane. Barone teaches that these compounds are closely related tertiary-alkane substrates suitable for liquid-phase oxidation and identifies C5–C8 as the most preferred carbon-number range. The substitution would have amounted to use of a known analogous substrate for the same type of liquid-phase oxidation reaction, with a reasonable expectation that oxidation would occur preferentially at the tertiary carbon.
Claim 26 requires a C5–C20 alkane. Barone’s 3–30-carbon genus and identified C5 and higher tertiary alkanes encompass this limitation. Claim 28 requires a C5–C8 alkane, which is Barone’s most preferred range. Claim 29 further requires water, as supplied by Grane.
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 15-16 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.
The specification enables ozone oxidation of isobutane under the disclosed conditions. The issue is whether the disclosure enables the full scope of the performance limitations recited in claims 15 and 16 without undue experimentation.
Claim 15 encompasses oxidation of any alkane having a tertiary carbon, using any protic additive within claim 1, while obtaining either at least 80 percent hydroxylate selectivity, an ozone-utilization value of at least 100 percent, or both. Claim 16 encompasses the same alkane and protic-additive scope while requiring CO₂ selectivity of no more than 10 percent. Neither claim is limited to isobutane.
The specification reports 85–90 percent tert-butyl-alcohol selectivity, ozone utilization of about 1.5 moles tert-butyl alcohol per mole ozone consumed, and less than 6 percent CO₂ selectivity under selected isobutane conditions. See specification ¶¶ [0006], [0021], [0034]–[0035], [0081]–[0095], and Tables 2 and 5. The working examples demonstrating the claimed performance thresholds are limited to isobutane.
The specification broadly identifies numerous alkanes but states only that the process “may be extended” to higher alkanes having tertiary carbons. See ¶¶ [0022] and [0095]. It does not disclose operating conditions that produce the claimed performance for isopentane, isohexane, isoheptane, isooctane, alkanes having multiple tertiary sites, or other covered substrates.
The disclosure also establishes that product selectivity and ozone utilization are highly condition-dependent. Ozone decomposes in the liquid phase; oxygenated products may react with ozone more rapidly than the starting alkane; and water concentration, ozone partial pressure, ozone fraction, contact time, accumulated alcohol, and product-removal conditions affect selectivity, ozone utilization, and over-oxidation. See ¶¶ [0020], [0030]–[0032], [0081]–[0095], and Figures 2–5.
Barone independently confirms that structurally different tertiary alkanes do not necessarily behave uniformly. Barone teaches that alkanes having more than one tertiary site may produce a profusion of products, that sites having similar structures may possess different activities, and that electron density, steric effects, and kinetic factors affect activity and selectivity. See Barone, col. 2, ll. 55–68 and col. 3, ll. 1–10.
The Wands factors are applied as follows:
Breadth of the claims. Claims 15 and 16 encompass an open genus of alkanes having a tertiary carbon, multiple protic additives, and broad operating conditions while requiring specified numerical performance throughout that scope.
Nature of the invention. The invention involves competing hydroxylation, peroxide formation, ozone decomposition, C–C bond cleavage, gas-phase oxidation, and liquid-phase over-oxidation pathways.
State of the art. The art recognizes that substrate structure, number and location of reactive sites, oxidant exposure, and reaction-medium composition affect product distribution.
Level of ordinary skill. A skilled artisan would understand alkane oxidation and reactor operation but would not be provided with a general structure-performance relationship identifying conditions that achieve the claimed thresholds for each covered alkane.
Predictability. The specification and Barone show that selectivity and oxidation behavior vary with substrate structure, phase behavior, competing reactive sites, and process conditions.
Direction provided. The specification provides substantial guidance for isobutane but does not provide corresponding conditions or predictive rules for other tertiary-carbon alkanes.
Working examples. All examples demonstrating at least 80 percent hydroxylate selectivity, at least 100 percent ozone utilization, or no more than 10 percent CO₂ selectivity concern isobutane.
Quantity of experimentation. Practice across the full scope would require screening alkane identity, protic-additive identity and concentration, temperature, total pressure, ozone fraction, ozone partial pressure, contact time, reactor configuration, and product-removal conditions for materially different substrates.
Considering these factors together, the disclosure enables the isobutane embodiments but does not enable the full scope of claims 15 and 16 without undue experimentation. Enablement must extend to the full claimed scope, and the Wands factors are used to determine whether the required experimentation is reasonable or undue.
Response to Applicant’s Arguments
Applicant argues that amended claim 1 is now limited to alkanes having a tertiary carbon and that the specification provides detailed guidance concerning isobutane, protic additives, temperature, pressure, ozone concentration, analytical methods, and tertiary C–H reactivity.
The amendment addresses the prior concern directed to primary-only alkanes and supports withdrawal of the broad enablement rejection against claims 1–14. It does not resolve the narrower enablement issue presented by claims 15 and 16. Those claims require numerical performance across the full tertiary-carbon alkane genus. The disclosure does not establish that isobutane is representative of all covered substrates or provide a rule by which the claimed selectivity, utilization, and CO₂ thresholds can be achieved for materially different tertiary alkanes without substantial experimentation.
Accordingly, the arguments are persuasive as to the general process claims but do not overcome the focused enablement rejection of claims 15 and 16.
Claims 22-29 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.
Claim 22 newly recites that “the liquid phase medium consists of the protic additive and the alkane.” The closed phrase “consists of” excludes components other than the recited protic additive and alkane.
The original disclosure does not describe the liquid-phase medium during the oxidation process as consisting only of the alkane and protic additive. Rather, the specification states that the liquid-phase medium comprises the alkane and ozone, that liquid alkane solubilizes ozone, and that the medium generally further comprises a protic additive. The specification further states that the medium may include a catalyst and resulting oxidation products. See specification ¶¶ [0025]–[0026].
Paragraph [0030] likewise states that the balance of the liquid-phase medium may be composed of the liquid alkane, “with ozone and any catalyst, if present, dissolved therein.” Original claim 8 used the open term “comprises” and did not exclude ozone, catalyst, or products.
Applicant identifies original claims 4 and 11, paragraphs [0022] and [0030], and the examples as support for claims 22–29. Those portions support water, isobutane, specified carbon-number ranges, and an alkane-rich medium. They do not reasonably convey possession of a liquid-phase medium that, during oxidation, excludes ozone and all components other than the alkane and protic additive.
Because the closed composition required by claim 22 is not described in the application as filed, claim 22 lacks adequate written-description support. Claims 23–29 incorporate the same unsupported limitation and are rejected for the same reason. A written-description rejection is proper where a new limitation is not reasonably conveyed by the original disclosure, even though related open-ended subject matter was disclosed.)
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 22-29 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 requires “combining an alkane and ozone in a liquid phase medium.” Claim 22 depends from claim 1 but states that the liquid-phase medium “consists of the protic additive and the alkane.” Given its ordinary closed meaning, the language of claim 22 excludes ozone from the same liquid-phase medium in which claim 1 requires ozone to be combined.
The specification does not resolve the conflict. Paragraph [0026] expressly states that the liquid-phase medium comprises the selected alkane and ozone and that the liquid alkane solubilizes at least some ozone. The specification also permits catalyst and reaction products in the liquid-phase medium.
It therefore cannot be determined whether claim 22 is intended to describe:
• the initial liquid charge before ozone introduction;
• the liquid-phase medium during oxidation;
• a medium free only of an additional bulk solvent or catalyst; or
• a medium that excludes ozone and products notwithstanding claim 1.
The metes and bounds of claim 22 are consequently unclear. Claims 23–29 depend from claim 22 and incorporate the same ambiguity.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 22-29 rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
A claim in dependent form must refer to a previously set forth claim and specify a further limitation of the subject matter claimed.
Claim 22 depends from claim 1 and therefore must retain claim 1’s requirement that alkane and ozone be combined in the liquid-phase medium. Claim 22 then recites that the medium “consists of” only the protic additive and alkane. To the extent the closed phrase excludes ozone, claim 22 removes or contradicts a limitation of claim 1 rather than further limiting the subject matter of claim 1.
Claim 22 therefore does not clearly include every limitation of the claim from which it depends and add a further limitation. Claims 23–29 depend from claim 22 and incorporate the same improper dependency.
Claim 27 is additionally rejected under 35 U.S.C. § 112(d) because it fails to specify a further limitation.
Claim 27 depends from claim 25 and recites that the protic additive is water. Claim 25 depends from claim 24, and claim 24 already requires that the protic additive be water. Claim 27 therefore repeats a limitation already incorporated through its dependency and does not further limit claim 25.
Claim 27 appears to have been intended to depend from claim 26. As written, claim 27 is not in proper dependent form.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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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