CTFR 18/683,043 CTFR 88613 DETAILED ACTION 07-03-aia AIA 15-10-aia The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Claim Status Claims 1, 2, 5-9, 12, 14, and 17-19 are amended. Claims 3, 4, and 16 are cancelled. The amendments to claims 2, 5-9, 12, 14, and 17-19 overcome the previous claim objections and 112(b) rejections. Claims 1, 2, 5-14, and 17-20 are pending for examination below. Response to Arguments Applicant’s arguments filed 30 December 2025 have been fully considered. Some are persuasive and some are not, as explained below. Applicant argues on page 9 of the Remarks that Bogan Jr. is directed to two processes, one for conversion of alkanes to alkenes and one for conversion of alkanes to unsaturated carboxylic acids or nitriles, and that the second process of conversion to unsaturated carboxylic acids or nitriles including paragraph [0113] as cited by the Examiner is not relevant to the claimed process of producing olefins from alkanes. Thus, Bogan Jr does not teach oxidative dehydrogenation of alkanes to olefins in the absence of oxygen as claimed. In response, the Examiner respectfully disagrees with this conclusion. Bogan Jr. teaches a variety of embodiments, each of which includes at least an intermediary step of conversion of alkanes to alkenes (see paragraphs [0045]-[0061]) which list 5 aspects of the invention of Bogan Jr). The Examiner’s rejection focuses on the second and third aspects , which are methods of producing an unsaturated carboxylic acid in two subzones, where the first catalyst and/or the first subzone are most favorable to producing alkenes (paragraphs [0049]-[0055], [0119], and [0131]). Paragraphs [0077]-[0126] discuss the second aspect and paragraphs [0127]-[0131] discuss the third aspect. Both the second and third aspects start with only alkane feed, use two subzones, and arrive at the carboxylic acid. Paragraph [0113] states that it is possible to use an alkane feed substantially in the absence of molecular oxygen for the vapor phase catalytic reaction of alkanes to carboxylic acids through alkenes, where when the molecular oxygen is not used, the catalyst is regenerated with an oxidative gas from time to time. Paragraph [0112] explains that molecular oxygen is not necessarily specifically O2 gas, but that molecular oxygen can include other oxygen-containing gases such as air. Thus, Bogan Jr. clearly contemplates a reaction of alkane to form alkene as part of a reaction scheme which converts alkane to unsaturated carboxylic acids, and also explains that it is possible to perform the reaction without a presence of oxygen, as claimed. Applicant also argues on pages 9-10 of the Remarks that Bogan Jr. explicitly teaches that the process for alkane dehydrogenation in Bogan Jr. requires the presence of oxygen, citing paragraphs [0069] and [0074]. In response, the Examiner agrees that when Bogan Jr. is discussing the first aspect, which is a method comprising only oxidative dehydrogenation of alkanes to alkenes, the presence of oxygen appears to be required as in the paragraphs cited by Applicant. However, as explained above, Bogan Jr. also teaches multiple other aspects, including the second aspect, where the second aspect is a process having two catalysts in two subzones, including a first subzone which produces alkene from alkanes (paragraphs [0049]-[0050] and [0119]). In this case, as explicitly stated in paragraph [0113] which discusses this second aspect, there is an option that the process can proceed in an absence of oxygen (paragraph [0113]). Thus, the rejection over Bogan Jr. is maintained. Applicant argues on page 10 of the Remarks that Sanchez Valente does not teach the reaction taking place without a presence of oxygen, as claimed in amended claims 1 and 2. In response, the Examiner agrees that Sanchez Valente does not teach the conversion takes place without a presence of oxygen, and the rejection as previously presented has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of a new interpretation of the previously presented prior art in view of the amendment. Claim Rejections - 35 USC § 103 07-20-aia AIA 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. 07-21-aia AIA Claim s 1, 2, 5-14 and 17-20 are rejected under 35 U.S.C. 103 as being unpatentable over Bogan Jr. et al. (US 2005/0176985) in view of Sanchez Valente et al. (US 9,409,156, cited on IDS of 2/12/2024) . With regard to claims 1 and 2 , Bogan Jr. teaches a process for conversion of alkanes in two sequential subzones, where the first subzone is maintained at reaction conditions most favorable to the production of the corresponding alkene (paragraphs [0054]-[0055]). The catalyst in the subzones comprises a mixed metal oxide having the formula A a M b N c X d O e , where A is Mo, M is V, N is Bi, and X is Nb (paragraphs [0129]-[0130]). The catalyst has an absence of tellurium, as claimed in instant claim 1 . The amounts for the subscripts are shown in the Table below. Claimed Mo v V w Nb y A z O x , where A is Bi Bogan Jr. Mo a V b Bi c Nb d O e v or a, respectively 1 1 w or b, respectively 0.1 to 0.5 0.01 to 1 y or d, respectively 0.001 to 0.3 0.01 to 1 z or c, respectively 0.01 to 0.3 0.01 to 1 x or e, respectively Oxygen required to charge balance Dependent on oxidation state of other elements The amounts of Bogan Jr. overlap the claimed amounts, rendering the ranges prima facie obvious. Thus, the catalyst of Bogan Jr. is equivalent to the catalyst of instant claims 1 and 2 . Bogan Jr. further teaches the reaction of alkanes to further products including alkenes and carboxylic acids takes place in the absence of molecular oxygen ( instant claims 1 and 2 ) (paragraph [0113]). Bogan additionally teaches the catalyst has a crystal structure comprising at least 2θ peaks observed at 22.1±0.3 and 28.2±0.3, at a relative intensity of 100 and 20-450, respectively (paragraph [0084]-[0085]). These match up with the claimed 2θ at 22.17±0.3 and 28.1±0.3, where the claimed 2θ have relative intensities of 100 and 10-30. The intensity of Bogan of 20-450 overlaps the claimed intensity of 10-30, rendering the intensity prima facie obvious. Bogan further teaches the crystal structure is useful if it shows other peaks than the observed 2θ, as long as the 2θ peaks at 22.1±0.3 and 28.2±0.3 are observed (paragraph [0085]). Bogan Jr. does not explicitly teach the remaining claimed 2θ values and intensities or that the crystallographic structure has the Pba2-32 space group. Sanchez Valente teaches an oxidative dehydrogenation process (column 15, line 48) having a similar catalyst comprising the elements Mo, V, Sb, Nb and Bi, and O in similar amounts and being without tellurium (column 4, lines 63-64). Sanchez Valente further teaches that the catalyst XRD pattern exhibits an orthorhombic pattern, which is a genus which comprises the Pba2-32 space group species, and also teaches the 2θ lines corresponding to a dominant M1 crystalline phase shown in the Table below (column 12, lines 8-11). Claimed 2θ (±0.3) Sanchez Valente 2θ(±0.4) 5.3 6.6 6.6 7.84 7.7 8.95 9.0 22.17 22.2 27.2 27.1 28.1 Thus, the 2θ of Sanchez Valente are very similar to the claimed 2θ. Sanchez Valente further teaches that when the XRD pattern comprises the M1 2θ lines above, along with additional diffraction lines not corresponding to M1, the catalysts having said XRD patterns such as Figure 2 are much more active and selective for the alkane dehydrogenation (column 12, lines 19-21). Sanchez Valente does not explicitly teach the relative intensities. However, in at least the XRD of Figure 2 of Sanchez Valente, if the peak at 22.1 (marked with an Asterisk in the Figure 2) is set to 100 relative intensity, the peaks at 6.6, 7.84, and 8.95 (marked with an Asterisk in the Figure 2) appear to be similar in relative intensity to the claimed ranges of 1.5-15, 2.5-45, and 4-21, and the peak at 27.1 (marked with an Asterisk in the Figure 2) appears to be similar in relative intensity to the claimed range of 20-50. Thus, one of ordinary skill in the art would reasonably expect the relative intensities of Sanchez Valente to be similar to the claimed relative intensities, rendering the claimed relative intensities prima facie obvious. Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to form the catalyst of Bogan Jr. such that the catalyst has the claimed crystallographic Pba2-32 space group, the claimed 2θ, and the claimed relative intensity data, because Bogan Jr. and Sanchez Valente each teach oxidative dehydrogenation with a catalyst comprising Mo, V, Bi, Nb, and O in similar amounts, Bogan Jr. teaches the catalyst should comprise at least 2θ of 22.1±0.3 and 28.1±0.3, having overlapping intensities with the claimed intensities and that other 2θ can be present, and Sanchez Valente teaches a catalyst having an orthorhombic pattern, a majority of the claimed 2θ with similar relative intensities, and that a catalyst comprising the M1 2θ lines with other crystal phases 2θ lines have much more activity and selectivity in the oxidative dehydrogenation reaction than catalysts which only have a single crystal phase (column 12, lines 19-21). With regard to claims 5, 6, and 17 , Bogan Jr. teaches the temperature is 200-700°C (paragraph [0115]), which overlaps the ranges of 300-700°C of instant claims 5 and 16 and 400-500°C of instant claim 6. With regard to claims 7, 8, and 18 , Bogan Jr. teaches the pressure is up to 50 psig (up to 3.45 barg) (paragraph [0115]). This is within the ranges of 0 to 20 barg of instant claims 7 and 18 and 0 to 10 barg of instant claim 8. With regard to claims 9 and 19 , Bogan Jr. only teaches a GHSV, not a WHSV, and the conversion is unable to be performed by the Examiner. However, one of ordinary skill in the art understands the WHSV affects the throughput and conversion of the reactants. Therefore, the WHSV is a result-effective variable, and can be optimized. Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to adjust the WHSV to 1 to 10 hr -1 as claimed, since it has been held that discovering an optimum value of a result effective variable involves only routine skill in the art. See MPEP 2144.05(II). With regard to claims 10, 11, and 20 , Bogan Jr. teaches a fluidized bed reactor (paragraph [0114]). With regard to claims 12 and 13 , Bogan Jr. teaches regeneration of the catalyst in a regeneration zone in the presence of air (paragraph [0113]). Air is understood to have an oxygen content in the claimed range of 2 to 22 vol%. With regard to claim 14 , Bogan Jr. does not specifically teach the pressure in the regeneration reactor. However, one of ordinary skill in the art understands the pressure is a process parameter than can be optimized without undue experimentation and with a reasonable expectation of success. Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to adjust the WHSV to 1 to 10 hr -1 as claimed, since it has been held that discovering an optimum value of a variable involves only routine skill in the art. See MPEP 2144.05(II) . 07-22-aia AIA Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Bogan Jr. et al. (US 2005/0176985) in view of Sanchez Valente et al. (US 9,409,156) as applied to claim 1 above, and further in view of Diefenbacher et al. (US 2006/0258529) . With regard to claim 15 , Bogan Jr. teaches the method above. Bogan Jr. further teaches the process comprises and additional step of forming carboxylic acids from the alkenes and alkenes from dehydrogenation (page 13, claim 19). Bogan Jr. does not specifically teach separation after the dehydrogenation step. Diefenbacher teaches a method for forming products from propane by oxidative dehydrogenation and oxidation (Abstract). Diefenbacher further teaches separating components other than propane and propene from the produce of the dehydrogenation before sending to the next step (paragraph [0003]). Diefenbacher additionally teaches this separation allows the process to function effectively and without catalyst poisons (paragraph [0008]). Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to add the step of separating of oxygenates, carbon monoxide, and/or carbon dioxide to the process of Bogan Jr, because each of Bogan Jr. and Diefenbacher teaches oxidative dehydrogenation and oxidation of alkanes to products in a two-step process, and Diefenbacher teaches that the process can comprise separation of components which are not propane and propene to allow the process to function without catalyst poisons (paragraph [0008]) . Double Patenting 08-33 AIA 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. 08-35 Claim s 1, 2, 5-9, 15, and 17-19 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim s 12, 14, and 15 of copending Application No. 18/683,045 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because claim 12 of Application 18/683,045 renders obvious instant claims 1 and 2. Instant claim 1 recites a process for oxidative dehydrogenation of an alkane to an alkene in the presence of a catalyst having the formula Mo v V w Nb y A z O x where A is Bi, v is 1, w is 0.1-0.5, y is 0.001 to 0.3, is 0.01 to 0.3, and x is charge balance. Instant claim 1 further recites an absence of tellurium in the catalyst, and an absence of a co-feed of oxygen to the dehydrogenation step. The catalyst of instant claim 1 further has the following XRD data and a Pba2-32 space group crystallographic structure. PNG media_image1.png 215 278 media_image1.png Greyscale Instant claim 2 recites a process for oxidative dehydrogenation of an alkane to an alkene in the presence of a catalyst having the formula Mo v V w Nb y Bi z O x where v is 1, w is 0.1-0.5, y is 0.001 to 0.3, is 0.01 to 0.3, and x is charge balance. Instant claim 1 further recites an absence of tellurium in the catalyst. The catalyst of instant claim 1 further has the following XRD data and a Pba2-32 space group crystallographic structure. PNG media_image1.png 215 278 media_image1.png Greyscale Claim 12 of Application 18/683,045 recites a process for oxidative dehydrogenation of an alkane to an alkene in the presence of a catalyst having the formula Mo v V w Nb y Bi z O x where v is 1, w is 0.1-0.5, y is 0.001 to 0.3, is 0.01 to 0.3, and x is charge balance. Instant claim 1 further recites an absence of tellurium in the catalyst. The catalyst of instant claim 1 further has the following XRD data and a Pba2-32 space group crystallographic structure. PNG media_image2.png 200 434 media_image2.png Greyscale The differences between instant claim 1 and claim 12 of Application 18/683,045 are i) claim 12 of Application 18/683,045 includes a specific example of the catalyst formula where A is Bi, rather than the more general formula of claim 1 where A can be Bi, Sb, or Pr, ii) claim 12 of Application 18/683,045 does not explicitly state the reaction is in the absence of oxygen, and iii) the presence of an additional separation step in claim 12 not present in independent claim 1. With regard to i), the recitation of the catalyst formula of Application 18/683,045 is a specific example of the broader formula of instant claim 1, and the formula of 18/683,045 anticipates the claimed formula. With regard to ii), claim 13 of Application 18/683,045 goes on to explicitly state the presence of oxygen in a feed in the dehydrogenation process, thus implying that claim 12, which has no explicit statement, can be done in the presence or absence of oxygen. One of ordinary skill in the art is capable of selecting the option of no oxygen, without undue experimentation, and with a reasonable expectation of success. With regard to iii), because of the additional step, the claims are not identical, but claim 12 of Application 18/18/683,045 encompasses instant claim 1. The difference between instant claim 2 and claim 12 of Application 18/683,045 is that there is an additional separation step in the claim 12 which is not present in instant claim 2 or the claims depending from instant claim 2. Thus, the claims are not identical, but claim 12 of Application 18/683,045 encompasses instant claim 2. Dependent instant claims 4-9, 15, and 17-19 recite the temperature, pressure, and WHSV of the reaction, and a step to separate the product to remove oxygenates, carbon monoxide, carbon dioxide, and/or alkanes. Dependent claims 14 and 15 of 18/683,045 recite the same temperature, pressure, and WHSV as the instant claims, and claim 12 of 18/683,045 recites separation of alkanes from the product. Thus, claims 12, 14, and 15 of 18/683,045 render obvious instant claims 1, 2, 5-9, 15, and 17-19, and the instant claims are unpatentable . This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented. Conclusion 07-40 AIA Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL . See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a). A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action. Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALYSSA L CEPLUCH whose telephone number is (571)270-5752. The examiner can normally be reached M-F, 8:30 am-5 pm, EST. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, In Suk Bullock can be reached at 571-272-5954. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. 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If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /Alyssa L Cepluch/Examiner, Art Unit 1772 /Renee Robinson/Primary Examiner, Art Unit 1772 Application/Control Number: 18/683,043 Page 2 Art Unit: 1772 Application/Control Number: 18/683,043 Page 3 Art Unit: 1772 Application/Control Number: 18/683,043 Page 4 Art Unit: 1772 Application/Control Number: 18/683,043 Page 6 Art Unit: 1772 Application/Control Number: 18/683,043 Page 7 Art Unit: 1772 Application/Control Number: 18/683,043 Page 8 Art Unit: 1772 Application/Control Number: 18/683,043 Page 9 Art Unit: 1772 Application/Control Number: 18/683,043 Page 10 Art Unit: 1772 Application/Control Number: 18/683,043 Page 11 Art Unit: 1772 Application/Control Number: 18/683,043 Page 12 Art Unit: 1772 Application/Control Number: 18/683,043 Page 13 Art Unit: 1772 Application/Control Number: 18/683,043 Page 14 Art Unit: 1772 Application/Control Number: 18/683,043 Page 15 Art Unit: 1772 Application/Control Number: 18/683,043 Page 16 Art Unit: 1772
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