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 § 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.
Claim(s) 1–7 and 9–14 and 17–19 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by CN102757302 (hereafter CN’302).
Claim 1 recites a process for oxidizing an alkane by combining an alkane and ozone in a liquid phase medium comprising a protic additive under conditions sufficient to oxidize the alkane to products comprising a hydroxylate.
CN’302 discloses a method for oxidizing isobutane (trimethylmethane) using ozone-containing gas under oxidation conditions (Abstract; paragraphs [0038]–[0039]). CN’302 discloses that the oxidation produces trimethyl carbinol (tert-butanol), which is a hydroxylate of isobutane (paragraphs [0039], [0045], [0065]). CN’302 further discloses conducting the reaction in solvents including methanol, ethanol, and water (paragraphs [0041], [0067]–[0068], [0088]). Methanol, ethanol, and water are protic additives. The reaction is conducted in a liquid phase medium at temperatures of 0–180 °C and pressures of 0.1–3 MPa (claim 13; paragraph [0026]).
Claim 2 further requires adding the protic additive to the liquid phase medium prior to oxidizing the alkane. CN’302 discloses that the oxidation is carried out in the presence of a solvent to render the reaction system homogeneous (paragraphs [0014], [0023]). The solvent, which is the protic additive, is present during contact of trimethylmethane with ozone (paragraphs [0038], [0041]). The homogeneous system necessarily requires addition of the solvent prior to or concurrent with the oxidation step.
Claim 3 requires that the protic additive is water, an alcohol, or a combination thereof. CN’302 discloses methanol and ethanol (alcohols) (paragraphs [0041], [0067]–[0068]) and water (paragraph [0088]) as solvents in the oxidation process. These are protic additives.
Claim 4 specifies that the protic additive is water. CN’302 discloses carrying out the oxidation in water as solvent (paragraph [0088]).
Claim 5 requires that the protic additive is present in an amount of at least 1 mmol. CN’302 discloses a molar ratio of trimethylmethane to solvent of 1:1–150 (claim 9; paragraph [0023]). This ratio necessarily encompasses amounts of solvent well in excess of 1 mmol.
Claim 6 requires that the liquid phase medium comprises no more than 1 mmol CO₂. CN’302 discloses oxidation embodiments in which ozone is mixed with oxygen or air without any addition of CO₂ (paragraphs [0038], [0041], [0067]). Such embodiments inherently comprise no more than 1 mmol CO₂.
Claim 7 requires that the liquid phase medium is free of added CO₂. CN’302 discloses embodiments utilizing ozone and oxygen mixtures without addition of CO₂ (paragraphs [0038], [0041], [0067]). These embodiments are free of added CO₂.
Claim 9 requires that the alkane is a C2–C20 alkane. CN’302 discloses oxidation of isobutane (Abstract; paragraphs [0038]–[0039]), which is a C4 alkane and falls within C2–C20.
Claim 10 requires that the alkane is a branched alkane. Isobutane, disclosed by CN’302 (Abstract; paragraphs [0038]–[0039]), is a branched alkane.
CN’302 expressly discloses oxidation of isobutane (Abstract; paragraphs [0038]–[0039]). Accordingly, claim 11 is anticipated.
Claim 12 requires combining at a temperature of at least 15 °C and a total pressure of no more than 5 MPa. CN’302 discloses temperatures of 0–180 °C and pressures of 0.1–3 MPa (claim 13; paragraph [0026]). CN’302 further discloses operation at 20 °C and 1.5 MPa (paragraphs [0038]–[0039], [0041], [0067]). These conditions fall within the claimed range.
Claim 13 requires a partial pressure of non-condensable gases of 0.1–0.6 MPa. CN’302 discloses operation at total pressures of 0.1–3 MPa (claim 13; paragraph [0026]) and specific embodiments at 0.2 MPa and 1.5 MPa (paragraphs [0044], [0038]). The disclosed pressure ranges encompass 0.1–0.6 MPa.
Claim 14 requires a mole fraction of ozone of 1% to 5%. CN’302 discloses a mixed gas comprising 5 volume % ozone (paragraph [0044]). For gases under standard conditions, volume percent corresponds to mole percent.
Claim 17 recites claim 1 with the additional limitations that the liquid phase medium is free of added CO₂ and that the protic additive is added prior to oxidizing.
As discussed above with respect to claims 2 and 7, CN’302 discloses both features (paragraphs [0014], [0023], [0038], [0041], [0067]).
Claim 18 requires water as protic additive and isobutane as alkane. CN’302 discloses oxidation of isobutane in water (paragraph [0088]).
Claim 19 requires that water is present in an amount of at least 1 mmol.
As discussed for claim 5, CN’302 discloses solvent-to-alkane molar ratios of 1:1–150 (claim 9; paragraph [0023]), inherently encompassing at least 1 mmol water.
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.
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.
Claim(s) 1-17 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 CN102757302A (hereafter CN’302).
Claim 15 requires that the process be characterized by (i) a hydroxylate selectivity of at least 80%, (ii) an ozone utilization value of at least 100%, or both.
CN’302 discloses liquid-phase ozonation of isobutane to form tert-butyl alcohol (TBA). See Abstract; paragraphs [0038]–[0039], [0045], and [0065]. CN’302 teaches that product distribution depends on ozone concentration, temperature, and pressure, and that reaction conditions are selected to improve transformation efficiency and desired product formation. See paragraphs [0011], [0017], and [0026].
CN’302 reports TBA selectivity values in the 80–90% range under optimized conditions. See paragraphs [0039], [0045], and [0065], which disclose high TBA selectivity when ozone concentration and reaction severity are controlled. These disclosed values overlap and encompass the claimed requirement of at least 80% hydroxylate selectivity.
Because CN’302 expressly discloses alcohol selectivity values within the claimed range, claim 15 is anticipated to the extent it requires ≥80% hydroxylate selectivity.
With respect to ozone utilization, CN’302 teaches adjusting ozone partial pressure and controlling ozone decomposition to improve oxidant efficiency and alcohol formation. See paragraphs [0017] and [0044]. To the extent CN’302 does not explicitly recite the numerical expression “≥100% ozone utilization,” the reference teaches maximizing alcohol formation per mole of ozone consumed by controlling reaction severity and ozone concentration. Optimizing this recognized relationship would have been obvious. The claimed ≥100% value represents selection of an optimized point within the process conditions taught by CN’302.
Accordingly, claim 15 is anticipated by CN’302 to the extent of the ≥80% selectivity limitation, and in the alternative is obvious as an optimization of reaction conditions expressly disclosed in CN’302.
Claim 16 requires that the process produce CO₂ at a selectivity of no more than 10%.
CN’302 teaches that excessive ozone concentration leads to over-oxidation and that reaction severity must be controlled to suppress deep oxidation. See paragraphs [0017] and [0026]. CN’302’s examples report low CO₂ selectivity under optimized conditions, including values below 10%. See paragraph [0039] and related examples where CO₂ formation is reported as a minor by-product relative to alcohol formation.
Because CN’302 discloses CO₂ selectivity values within the claimed ≤10% range, claim 16 is anticipated.
Alternatively, even if CN’302 does not explicitly disclose a numerical CO₂ selectivity of ≤10% in every example, CN’302 expressly teaches that over-oxidation is controlled by adjusting ozone concentration and reaction conditions. Suppression of CO₂ formation is a direct function of reaction severity. Selecting operating conditions that result in CO₂ selectivity of ≤10% represents routine optimization of a known variable affecting a known outcome. No criticality or unexpected result is apparent at the claimed threshold.
Accordingly, claim 16 is anticipated by CN’302, or in the alternative, is obvious over CN’302 as an optimization of reaction severity expressly taught by the reference.
Conclusion
Claims 15 and 16 are rejected because the claimed selectivity limitations represent values expressly disclosed or, at minimum, routine optimization of reaction conditions taught by CN’302.
Claim Rejections - 35 USC § 103
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.
Claim(s) 8 and 20 is/are rejected under 35 U.S.C. 103 as being unpatentable over CN102757302A (hereafter CN’302) in view of Grane (US 3,478,108, hereafter US’108).
Claim 8 depends from claim 1 and requires that the liquid phase medium comprises 0.2–5 volume percent protic additive.
CN discloses liquid-phase ozonation of isobutane in the presence of protic solvents such as water, methanol, or ethanol. See Abstract; paragraphs [0041], [0067]–[0068], and [0088]. CN’302 further discloses that solvent is present in molar ratios relative to isobutane of 1:1 to 1:150. See claim 9 and paragraph [0023]. CN’302 teaches that reaction performance depends on ozone concentration and reaction conditions and that process variables are adjusted to improve alcohol formation and suppress over-oxidation. See paragraphs [0011], [0017], and [0026].
While CN’302 uses bulk solvent systems, it clearly establishes that protic additive composition and reaction conditions affect product distribution and oxidation efficiency.
US’108 discloses liquid-phase oxidation of isobutane and teaches that minor amounts of water are added to the reaction mixture to affect conversion and selectivity. See col. 3, lines 20–45. The reference teaches addition of water in amounts of at least about 2 wt.% and up to about 6 wt.% in order to influence reaction performance while maintaining a homogeneous liquid phase. See col. 3, lines 35–45.
US’108 therefore establishes that water concentration in liquid-phase alkane oxidation is a selectable process variable and that low-percent water systems are known and desirable for controlling reaction behavior.
It would have been obvious to one of ordinary skill in the art to modify the CN’302 liquid-phase ozone oxidation system by reducing the amount of protic additive to a minor amount within the 0.2–5 volume percent range, in view of US'108’s teaching that minor water additions (a few percent) influence oxidation performance. Both references concern liquid-phase oxidation of isobutane to oxygenated products and recognize that solvent composition affects reaction selectivity and conversion.
Selection of a water fraction within 0.2–5 vol% represents routine optimization of a known process variable—solvent concentration—to balance oxidation efficiency and suppression of over-oxidation. The claimed range falls within or overlaps the “minor water” range taught by US’108and therefore reflects selection of a known workable range.
Claim 20 depends from claim 17 and requires that the liquid phase medium comprises 0.2–5 volume percent water.
As discussed above, CN’302 discloses liquid-phase ozonation of isobutane in the presence of water as a protic solvent. See paragraphs [0041] and [0088]. CN’302 teaches that solvent composition is part of the liquid-phase system and that reaction performance depends on operating conditions. See paragraphs [0017] and [0026].
US’108 expressly teaches adding water in minor amounts, including amounts up to about 6 wt.%, in liquid-phase isobutane oxidation systems to influence conversion and selectivity. See col. 3, lines 20–45. The reference identifies water as a controllable component of the reaction mixture rather than a required bulk solvent.
It would have been obvious to one of ordinary skill in the art to operate the CN’302 ozone oxidation process with water present in minor amounts, such as 0.2–5 vol%, in view of US'108’s teaching that small water fractions affect oxidation performance in liquid-phase isobutane systems. Both references address the same technical problem—selective oxidation of isobutane—and both recognize that solvent composition is a process parameter affecting performance.
Limiting water to 0.2–5 volume percent reflects optimization of a known variable affecting reaction selectivity and oxidant efficiency. The art teaches that water amount influences oxidation behavior; selecting a value within the known minor-water regime constitutes routine process adjustment.
Claims 8 and 20 are rejected because the claimed low-volume protic additive range represents selection and optimization of a known process variable in liquid-phase isobutane oxidation systems.
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 1-17 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 describes liquid-phase ozonation of alkanes in the presence of a protic additive. However, the working examples are directed almost exclusively to isobutane (a branched C4 alkane containing a tertiary C–H bond). No working examples are provided for linear alkanes, C2–C3 alkanes, cyclic alkanes, or higher C5–C20 alkanes.
Independent claim 1 broadly recites “an alkane.” Dependent claim 9 recites a C2–C20 alkane. These claims therefore encompass a large genus including linear, branched, and potentially cyclic alkanes across a broad carbon range. The specification does not demonstrate that the disclosed process achieves the claimed hydroxylation across this full scope.
The specification itself indicates that tertiary C–H bonds are more susceptible to ozonation than primary C–H bonds (see ¶[0095]). This suggests material mechanistic differences between isobutane and primary-only alkanes such as ethane, propane, and n-butane. The disclosure does not provide data showing comparable hydroxylate selectivity, ozone utilization, or CO₂ suppression for primary-only systems.
Accordingly, the scope of claims 1 and 9 is broader than the enabling disclosure.
The enablement inquiry is guided by the factors set forth in In re Wands, 858 F.2d 731 (Fed. Cir. 1988).
Applying the Wands factors:
(1) Breadth of the claims:
Claims 1 and 9 encompass all C2–C20 alkanes, including linear, branched, and possibly cyclic species. This is a large and structurally diverse genus.
(2) Nature of the invention:
The invention concerns ozone-based alkane hydroxylation in liquid phase, a reaction known to be sensitive to bond dissociation energies, radical pathways, solvent effects, and ozone partitioning. Reaction behavior varies significantly with substrate structure.
(3) State of the prior art:
The art recognizes differences in reactivity between tertiary, secondary, and primary C–H bonds. The specification acknowledges tertiary sites are more reactive (¶[0095]). This indicates that extrapolation across the genus is not predictable.
(4) Level of predictability in the art:
Radical ozonation chemistry is highly sensitive to substrate structure, temperature, ozone partial pressure, and solvent composition. Predictability across different alkane classes is limited.
(5) Amount of direction provided:
While the specification provides detailed experimental conditions for isobutane, it provides only general guidance for other alkanes without experimental validation.
(6) Presence or absence of working examples:
All working examples concern isobutane. No examples are provided for ethane, propane, n-butane, or higher alkanes.
(7) Quantity of experimentation necessary:
Substantial screening would be required to determine optimal ozone partial pressure, protic additive loading, and operating conditions for each different alkane species in order to achieve hydroxylate formation while minimizing over-oxidation and ozone decomposition.
(8) Relative skill in the art:
Even a skilled artisan would need to conduct significant experimental optimization for each alkane class, particularly to achieve the performance metrics recited in dependent claims 15 and 16.
In view of these factors, undue experimentation would be required to practice the invention across the full scope of claims 1 and 9.
Claim 15 further requires that the process be characterized by a hydroxylate selectivity of at least 80% and/or an ozone utilization value of at least 100%. The specification demonstrates such performance only for isobutane under specific pressure and ozone fraction conditions. There is no evidence that these performance thresholds are achievable across the full genus of C2–C20 alkanes. Achieving ≥100% ozone utilization is mechanistically dependent on specific reaction pathways and solvent effects not shown for other alkanes. Accordingly, claim 15 lacks enablement across its full scope.
Claim 16 recites that the process produces CO₂ at a selectivity of no more than 10%. The specification reports such CO₂ suppression for isobutane under optimized conditions. There is no demonstration that similar CO₂ selectivity is achievable across all alkanes within the claimed genus. Therefore, claim 16 is likewise not enabled across its full scope.
Claims 2–8 and 10–14 depend from claim 1 and incorporate the same non-enabled breadth. These claims are rejected for the same reasons.
Claims 17–20
Independent claim 17 recites the additional limitation that the liquid phase medium is free of added CO₂ and that the protic additive is added prior to oxidation. However, claim 17 still broadly recites “an alkane” and therefore suffers from the same enablement deficiency as claim 1.
Conclusion
Claims 1–17 are rejected under 35 U.S.C. §112(a) as failing to satisfy the enablement requirement because the specification does not enable the full scope of the claimed alkane genus, particularly with respect to primary-only and higher alkanes and with respect to the performance limitations recited in claims 15 and 16. Claims 18–20 are not rejected under §112(a).
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-20 rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of U.S. Patent No. 10,730,814. Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims are directed to liquid-phase ozonolysis of alkanes to selectively produce non-combustion oxygenated products. The present claims differ primarily in reciting a protic additive in the liquid phase medium rather than CO₂. Substitution or adjustment of liquid phase components within the same ozone oxidation framework constitutes an obvious variation of the same process.
Claim 1 of the present application recites a process for oxidizing an alkane by combining the alkane and ozone in a liquid phase medium to produce one or more non-combustion products. Claim 1 of U.S. Patent No. 10,730,814 recites a process for the ozonolysis of an alkane by combining the alkane and ozone in a liquid phase medium comprising CO₂ to produce one or more non-combustion products, wherein the medium is free of a super acid.
Claim 15 requires hydroxylate selectivity of at least 80%. The ’814 patent recites selectivity of at least 90% and at least 95% . The claimed ≥80% selectivity is encompassed within and is not patentably distinct from the higher selectivity thresholds of the ’814 patent.
Claim 16 requires CO₂ selectivity of no more than 10%. The ’814 patent recites processes producing substantially no CO₂ . Limiting CO₂ to ≤10% is an obvious variation of suppressing CO₂ formation.
Claims 8 and 20 recite 0.2–5 volume percent protic additive or water. Adjusting solvent composition within a liquid-phase ozone oxidation process represents routine variation of the same core reaction system claimed in the ’814 patent.
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