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 Status
Claims 1-20 were filed on 11/15/2023. In a preliminary amendment filed on the same day, claims 3, 4, and 11 were amended. Claims 1-20 are pending.
Priority
The instant application was filed on 11/15/2023 and claims the benefit of priority to:
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See filing receipt dated 4/22/2024.
Specification/Drawings
The disclosure is objected to because of the following informalities: the Figures and text in [0019] and [0116] are objected to because they are blurry and/or difficult to read.
Additionally, in [0143] the “mix zone 731” should recite “mix zone 730” as depicted in Fig. 2.
Appropriate correction is required.
The drawings are objected to as failing to comply with 37 CFR 1.84(p)(5) because they include the following reference character(s) not mentioned in the description: “400” and “420” of Fig. 1.
Corrected drawing sheets in compliance with 37 CFR 1.121(d), or amendment to the specification to add the reference character(s) in the description in compliance with 37 CFR 1.121(b) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Claim Rejections - 35 USC § 112(b)
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 1-20 are 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.
The last paragraph of claim 1 recites the following:
“and R3 is hydrogen or an alkyl group having 1 to 6 carbon atoms; wherein R3 is hydrogen or an alkyl group having 1 to 3 carbon atoms, and wherein R2 is not a methyl group; and said mother liquor stream in a solvent recovery zone to form an impurity rich waste stream; and routing a portion of said impurity rich waste stream to a solid-liquid separation zone to form a purge mother liquor stream.”
This paragraph is indefinite for multiple reasons. First, is that the definitions of variables R2 and R3 are unclear. R2 is first defined as an alkyl group having 1 to 6 carbon atoms and R3 is first defined as hydrogen or an alkyl group having 1 to 6 carbon atoms. However, the claim then recites “wherein R3 is hydrogen an alkyl group having 1 to 3 carbon atoms, and wherein R2 is not a methyl group”. It is not clear if this is a proviso, if it is reciting preferred embodiments of the broader ranges, or if they are further limiting the definitions of R2 and R3. Therefore, it is not clear if R3 includes alkyl groups having 4 to 6 carbon atoms and if R2 includes methyl groups (C1 alkyl).
The paragraph is further indefinite because there is a lack of antecedent basis for the limitation “said mother liquor stream in a solvent recovery zone”. Nor does the limitation make sense because there appears to be at least a verb missing for some process step which follows the contacting step and forms a mother liquor stream in a solvent recovery zone. Therefore, it is not clear what other steps are being required in this limitation. Instant Figure 1 teaches that the contacting step takes place in oxidation zone (100) to produce product stream (110), which is sequentially fed to a cooling zone (200) and a solid-liquid separation zone (300) to produce a mother liquor stream (330) comprising oxidation solvent, catalyst, and impurities. See [0129] of the specification as filed. The mother liquor stream is then routed to a mother liquor purge zone (700) in Fig. 1. Fig. 2 teaches that the mother liquor purge zone comprises feeding the mother liquor stream comprising impurities into a solvent recovery zone (710) to produce an impurity rich stream (712) that is fed to a second solid-liquid separation zone (720) to produce a purge mother liquor stream (723). Therefore, there appears to be at least three steps missing from the claimed process to get to the “impurity rich waste stream” (cooling, solid/liquid separation, solvent recovery), which is then fed to “a solid-liquid separation zone to form a purge mother liquor stream” as required by the last lines of claim 1.
For the purposes of examination, the process will be interpreted to require at least a solvent recovery step to form an impurity rich waste stream and a step of routing a portion of said impurity rich waste stream to a solid-liquid separation zone to form a purge mother liquor stream. None of the dependent claims cure this deficiency.
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) 1-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Janka (US2019/0389822A1, published on 12/26/2019) in view of Parker (US2016/0221980A1, published on 8/4/2016).
Applicant claims a process for preparing a compound of formula (I):
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comprising contacting a compound of formula (II):
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with an oxidizing agent in the presence of an oxidation catalyst and a solvent, wherein a stream is fed to a solvent recovery zone to form an impurity rich waste stream and routing a portion of said impurity rich waste stream to a solid-liquid separation zone to form a purge mother liquor stream.
Janka teaches a method for preparing 5-(alkoxycarbonyl)furan-2-carboxylic acids (ACFC), including 5-(methoxycarbonyl)furan-2-carboxylic acid (MCFC), from feedstocks comprised of furoates, including methyl 5-methylfuran-2-carboxylate (MMFC). See abstract. MMFC is a compound of instant formula (II) wherein R1 is hydrogen and R2 is methyl, a C1 alkyl and MCFC is a compound of instant formula (I) wherein R2 is methyl. See [0019]. Janka teaches that the furoates further include those of instant formula (II) wherein R1 is R3O or R3C(O)O-, R2 is a C1-C3 alkyl; and R3 is hydrogen or C1-2 alkyl. See [0019]. Janka teaches that the reaction of MMFC to MCFC corresponds to eq. 1 in [0019]:
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in the presence of air as an oxidizing agent; an oxidation catalyst comprising cobalt (Co), manganese (Mn), and bromine (Br); and acetic acid (C2 monocarboxylic acid-claim 7) as a solvent. The oxidizing step is further discussed in [0016-0041].
Janka teaches that the process is preferably carried out according to that in Fig. 1:
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. The process comprises feeding an oxidizable raw material stream comprising a furoate of instant formula (II) (30), a solvent stream (20), and an oxidizing gas stream (10) to an oxidation zone (125) to produce a carboxylic acid composition (110) comprising a compound of instant formula (I) (AFCA) and a furan dicarboxylic acid (FDCA). See [0005] for definition of FDCA and [0016-0022 and 0041]. The composition (110) is fed to a liquid displacement zone (225) with a fresh solvent stream (220) to produce an impurity rich displaced mother liquor stream (230) and a low impurity slurry stream (210) comprising ACFC. See [0042-0043]. The impurity rich displaced mother liquor stream (230) can be recycled back to the oxidation reactor with (910) or without (230) further treatment in a purge zone (235). The purge zone produces an impurity rich purge mother liquor stream (920) and a recovered solvent stream (910) comprising solvent and catalyst. See [0044].
Janka is silent regarding the specific processes employed in the purge zone does not explicitly teach that the purge zone comprises a solid-liquid separation zone. However, Janka does teach that solids may be present in the oxidation zone (125). See [0031]. Janka also teaches that stream (210) comprising ACFC comprises 1 to 50 wt% of solids. See [0042-0043]. Therefore, solids are expected in the mother liquor stream (230).
Parker is directed toward an analogous oxidation process to that of Janka, wherein a feed stream comprising at least one oxidizable furfural compound is used to generated a crude carboxylic acid slurry comprising FDCA and compositions thereof. See abstract and claims. Parker teaches according to equation 3 in [0020] that the oxidation of furfural derivative (5-EMF) under similar conditions to that of Janka (Co/Mn/Br catalyst, AcOH solvent, O2 and heat) produces a mixture of FDCA; FFCA; and EFCA:
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. EFCA is a compound of instant formula (I) wherein R2 is ethyl, a C2 alkyl. The fufurals of Parker are one oxidation state lower than the furoates of Janka, but can produce a product mixture comprising FDCA and EFCA. Also see Table 3 in [0050-0051].
Parker teaches that the furfural oxidation takes place according to the process of Fig. 1:
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. This process is analogous to that of Janka and produces an impurity rich mother liquor (330) which can be fed to a mother liquor purge zone (700) to produce an impurity rich mother liquor purge stream (751), a recycle oxidation stream (711) comprising oxidation solvent, and a raffinate stream comprising oxidation catalyst (742), wherein streams (711) and (742) may be recycled back to the oxidation reaction. See [0034-0043].
In Fig. 2, Parker discusses a preferred embodiment of the mother liquor purge zone:
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. See [0043-0049]. Parker teaches that the mother liquor comprising impurities (330) is fed to a solvent recovery zone (710) to produce solvent recycle stream (711) and an impurity rich waste stream (712) comprising oxidation by products and catalyst. The impurity rich waste stream (712) can be fed to a catalyst recovery zone (760) and/or solid-liquid separation zone (720) to generate a purge mother liquor stream (723) and a wet cake stream (722). Stream (723) may be further extracted and distilled to recover the oxidation catalyst (742) and a waste purge stream (751).
It would have been prima facie obvious to combine the teachings of Janka and Parker to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to include the claimed mother liquor purification steps in the process of Janka because Parker teaches that such steps are already known in the art for purifying analogous mixtures and recovering impurity lean oxidation solvent and catalyst for recycle. Further, both Janka and Parker teach that solid impurities are further expected in the mother liquor of the similar processes. Therefore, including the specific purge zone purification process of Parker in the process of Janka will predictably result in a more efficient process which recycles higher purity solvent and catalyst back to the oxidation reaction. Also see MPEP 2143(I)(A).
Regarding claims 2 and 4, Janka teaches that the oxidizing gas can be oxygen or air. See [0024]. Regarding claims 3 and 5, Janka teaches that the oxidation temperature can very from 100°C to 180°C, which is identical to the claimed range. See [0031] and MPEP 2144.05. Regarding claim 6, Janka teaches that the pressure of the oxidation falls within the range of 50 psig to 1000 psig, which is the same as that claimed. See claim 21 and MPEP 2144.05. Regarding claim 8, Janka teaches that the bromine is present as an anion can be derived from hydrobromic acid or sodium bromide. See [0036]. Regarding claims 9-12, Janka teaches that the weight ratio of Co:Mn ranges from 0.01 to 400:1, which encompasses the claimed ranges. See [0037]. Janka also teaches the weight ratio is preferably 10 to 400 or 1 to 400 or 10 to 200 or 20 to 100 to produce the ACFC compound of instant formula (I) at a minimum of 60-99.5% yield. If the yield of ACFC is above 80%, then the yield of FDCA will be less than 20%. See [0040] and MPEP 2144.05. Also see examples in [0065-0089]. Regarding claims 13-19, Janka teaches that the final ACFC produce is a dried solid comprising up to about 99.4 wt% ACFC, as low as 0.036 wt% of FDCA; and 0 ppmw of FFCA and AFFC, based on the total weight of the product. Janka teaches that the b* of the dried solid product ranges from -0.59 to 0.62. See examples in [0065-0089] and [0056-0059]. Thus, Janka meets all the limitations of the claims. Also see MPEP 2144.05.
Further regarding claim 20, Janka does teach a secondary oxidation zone (335) in Fig. 1 to enhance impurity removal to produce the dried solid ACFC. See [0047-0049]. However, the experimental data in [0065-0089] does not appear to have been generated using a secondary oxidation step and meets all of the purity limitations claimed.
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 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-21 of US Patent No. 10941245 (‘245) in view of Parker (US2016/0221980A1, published on 8/4/2016).
The claims of ‘245 are directed toward the claimed reaction to produce ACFC products in the purity levels set forth in claims 11-19. The claims of ‘245 do not explicitly teach that a stream is sent to a solvent recovery zone to form an impurity rich waste stream which is then routed to a solid-liquid separation zone to form a purge mother liquor stream.
The teachings of Parker were discussed above and are incorporated by reference herein.
It would have been prima facie obvious to combine the teachings of the claims of ‘245 and Parker to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to include the claimed mother liquor purification steps in the process of the claims of ‘245 because Parker teaches that such steps are already known in the art for purifying analogous mixtures and recovering impurity lean oxidation solvent and catalyst for recycle. Therefore, including the specific purge zone purification process of Parker in the process of the claims of ‘245 will predictably result in a more efficient process which recycles higher purity solvent and catalyst back to the oxidation reaction. Also see MPEP 2143(I)(A).
Claims 1-20 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-13 of US Patent No. 11440895 (‘895) in view of Parker (US2016/0221980A1, published on 8/4/2016).
The claims of ‘895 are directed toward the claimed reaction to produce ACFC products in the purity levels set forth in claims 11-19. The claims of ‘895 do not explicitly teach that a stream is sent to a solvent recovery zone to form an impurity rich waste stream which is then routed to a solid-liquid separation zone to form a purge mother liquor stream.
The teachings of Parker were discussed above and are incorporated by reference herein.
It would have been prima facie obvious to combine the teachings of the claims of ‘895 and Parker to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to include the claimed mother liquor purification steps in the process of the claims of ‘895 because Parker teaches that such steps are already known in the art for purifying analogous mixtures and recovering impurity lean oxidation solvent and catalyst for recycle. Therefore, including the specific purge zone purification process of Parker in the process of the claims of ‘895 will predictably result in a more efficient process which recycles higher purity solvent and catalyst back to the oxidation reaction. Also see MPEP 2143(I)(A).
Claims 1-20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of co-pending Application No. 18/560956 (‘956, reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘956 are directed to the product of the claimed process, which is recited using product-by-process language. Therefore, if the product of ‘956 is produced using the steps recited in the claims, then the process will be identical to that claimed. Also see MPEP 2113 and MPEP 2131.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of co-pending Application No. 18/560953 (‘953, reference application) in view of Parker (US2016/0221980A1, published on 8/4/2016).
The claims of ‘953 are directed toward the claimed reaction wherein a portion of said solvent is recycled from purge process. The claims of ‘953 do not explicitly teach that a stream is sent to a solvent recovery zone to form an impurity rich waste stream which is then routed to a solid-liquid separation zone to form a purge mother liquor stream.
The teachings of Parker were discussed above and are incorporated by reference herein.
It would have been prima facie obvious to combine the teachings of the claims of ‘953 and Parker to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to include the claimed mother liquor purification steps in the process of the claims of ‘953 because Parker teaches that such steps are already known in the art for purifying analogous mixtures and recovering impurity lean oxidation solvent and catalyst for recycle. Therefore, including the specific purge zone purification process of Parker in the process of the claims of ‘953 will predictably result in a more efficient process which recycles higher purity solvent and catalyst back to the oxidation reaction. Also see MPEP 2143(I)(A).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of co-pending Application No. 18/293923 (‘923, reference application) in view of Parker (US2016/0221980A1, published on 8/4/2016).
The claims of ‘923 are directed toward the claimed reaction wherein a portion of said solvent is recycled from purge process. The claims of ‘923 do not explicitly teach that a stream is sent to a solvent recovery zone to form an impurity rich waste stream which is then routed to a solid-liquid separation zone to form a purge mother liquor stream.
The teachings of Parker were discussed above and are incorporated by reference herein.
It would have been prima facie obvious to combine the teachings of the claims of ‘293 and Parker to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to include the claimed mother liquor purification steps in the process of the claims of ‘923 because Parker teaches that such steps are already known in the art for purifying analogous mixtures and recovering impurity lean oxidation solvent and catalyst for recycle. Therefore, including the specific purge zone purification process of Parker in the process of the claims of ‘923 will predictably result in a more efficient process which recycles higher purity solvent and catalyst back to the oxidation reaction. Also see MPEP 2143(I)(A).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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