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 .
DETAILED ACTION
1. Claims 1-16 are pending in the current application.
2. This application is a 371 of PCT/EP2020/081896 11/30/2020; FOREIGN APPLICATIONS: NETHERLANDS 2024242 11/15/2019.
Claim Rejections/Objections Withdrawn
3. The provisional rejection of claims 1-16 under 35 U.S.C. 101 as claiming the same invention as that of claim 1-16 of copending Application No. 17/736,415 (reference application) is withdrawn in view of the abandonment of the ‘415 application.
Claim Rejections Maintained
4. The rejection of claim(s) 1-16 is/are under 35 U.S.C. 103 as being unpatentable over North US 2011/0015409 A1 and Melendez in view of Balthasart 6,723,861 and Jokiel is maintained. Applicant's arguments filed July 31, 2025 have been fully considered but they are not persuasive. According to the arguments Balthasart is not prior art because it is non-analogous art. In response to applicant's argument that Balthasart is nonanalogous art, it has been held that a prior art reference must either be in the field of the inventor’s endeavor or, if not, then be reasonably pertinent to the particular problem with which the inventor was concerned, in order to be relied upon as a basis for rejection of the claimed invention. See In re Oetiker, 977 F.2d 1443, 24 USPQ2d 1443 (Fed. Cir. 1992). In this case, the art is chemical engineering. Therefore the entire field of chemical engineering is analogous art. However, the art is so similar that the compound produced in Balthasart is the starting material of the instant process, the epoxide. Those working in the field would be apprised of methods and apparatus related to preparing the starting materials for the claimed process and such a connected reactor design would dovetail nicely into product streams therefrom. As discussed in MPEP 2141.01(a), “The Supreme Court’s decision in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 82 USPQ2d 1385 (2007), did not change the test for analogous art as stated in Bigio. Under Bigio, a reference need not be from the same field of endeavor as the claimed invention in order to be analogous art. Bigio, 381 F.3d at 1325, 72 USPQ2d at 1212. This is consistent with the Supreme Court's instruction in KSR that "[w]hen a work is available in one field of endeavor, design incentives and other market forces can prompt variations of it, either in the same field or a different one."
According to the arguments, the differences between the prior art and the instant claims “have not been properly acknowledged” pointing to the terms “slurry” and the product as a liquid that is “discharged”. As discussed in the rejection, the catalyst is the same and the instant claim 2, which is drawn to the solid supported materials. As North explains “Solid supports for covalent binding of particular interest in the present invention include siliceous MCM-41 and MCM-48 (modified with 3-aminopropyl groups), ITQ-2 and amorphous silica, SBA and hexagonal mesoporous silica. Also of particular interest are sol-gels.” If these materials are mixed with immiscible liquids they are described as slurries. A slurry is a thin mixture of an insoluble solid suspended in a liquid, which is a property of the prior art. With respect to discharging the product cyclic carbonate, this is just separation from the rest of the reaction mixture, which is shown in the prior art.
According to the arguments, “the requisite motivation has not been articulated” however the rejection gives a number of motivations to use serially linked reactors. By using serially linked reactors, it is possible to isolate the catalyst from the product and reactivate it, without interrupting product flow. No catalyst has an infinite lifetime. The accepted view of a catalytic cycle is that it proceeds via a series of reactive species, be they transient transition state type structures or relatively more stable intermediates. Reaction of such intermediates with excess reagent or substrate can give rise to very stable complexes that are kinetically incompetent of sustaining catalysis. Removing the excess reagent would remove the over ligated complexes by reversing the reactions that led to their formation and would improve catalyst performance. A series of linked reactors is highly advantageous to limit the interval between regenerations by extending contact with regenerated or fresh catalyst for as long as possible in separate reaction vessels. Such a system is more tolerant of upsets, and blockage than a facility containing a single reactor which must be shut down periodically for catalyst replacement or reactivation. Furthermore, the catalyst consumption of the serially connected cascade reactors will be less than the single reactors for an equivalent total reactor volume. In this case Melendez has shown in the discussion on pages 3891-3893 that the catalyst is deactivated and can be reactivated with benzyl bromide or other quaternization reagents.
The provisional rejection of claims 1-16 rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-19 of copending Application No. 17/771,223 in view of Balthasart 6,723,861 and Jokiel is maintained.
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.
5. Claim(s) 1-16 is/are rejected under 35 U.S.C. 103 as being unpatentable over North US 2011/0015409 A1 and Melendez “One-component bimetallic aluminium(salen)-based catalysts for cyclic carbonate synthesis and their immobilization” Dalton Trans., 2011, 40, 3885–3902 in view of Balthasart 6,723,861 and Jokiel “Miniplant-Scale Evaluation of a Semibatch-Continuous Tandem Reactor System for the Hydroformylation of Long-Chain Olefins” Ind. Eng. Chem. Res. 2019, 58, 2471-2480. The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
Determination of the scope and content of the prior art
(MPEP 2141.01)
North teaches the process of the instant claims in a single pot with the catalyst of claim 5-6 and a halide source. Page 1 “[0011] The present inventor has now found that it is possible to incorporate the co-catalyst required in this work into the catalyst molecule, so as to reduce or eliminate the amount of separate components needed. Furthermore, the present inventor has also found it is possible to immobilise the combined catalyst and co-catalyst on a solid support.” Example 5 is immobilized (supported) and is the catalyst of claim 2. Additional supports of claim 4 are described “Solid supports for covalent binding of particular interest in the present invention include siliceous MCM-41 and MCM-48 (modified with 3-aminopropyl groups), ITQ-2 and amorphous silica, SBA and hexagonal mesoporous silica. Also of particular interest are sol-gels. Other conventional forms may also be used.” [Page 3 paragraph 0035]. Regarding claim 3, “Such supports will preferably take the form of small beads, pins/crowns, laminar Surfaces, pellets or disks. They may also take the form of powders.” Such powders appear to have the properties of claim 3.
PNG
media_image1.png
432
384
media_image1.png
Greyscale
Melendez teaches the same catalyst of claim 6, as compound 12 b on page 3888, Scheme 5. Additional supported catalysts such as 15c are disclosed on page 3889 in Scheme 6.
Melendez on page 3890 column 1, discusses the deactivation and regeneration of the catalyst with halide compounds:
It is apparent from Fig. 1 that silica-supported catalyst 16a does lose its catalytic activity over the first eleven reactions. However, this is entirely due to dequaternization of the ammonium salts by a reverse Menschutkin reaction49 as previously observed for reactions catalysed by the two-component catalyst system of 1 and tetrabutylammonium bromide (Scheme 2).39b,42 For the two-component system, catalyst activity could be restored by adding fresh batches of tetrabutylammonium bromide as the tributylamine was distilled out of the reaction mixture at the end of each reaction….. In the event, treatment of deactivated catalyst 16a with benzyl bromide totally restored its catalytic activity and the process was reproducible over at least three deactivation–activation cycles, covering a total of 32 sequential reactions (Fig. 1). This suggests that the dequaternization occurs selectively by cleavage of the ethyl or benzyl groups (Fig. 2; bond type a), presumably because these are the least hindered carbon–nitrogen bonds, consistent with the SN2 nature of the reverse Menschutkin reaction.49”
Melendez explains in the discussion of the flow reactor on page 3891, “This suggested that the catalyst would be suitable for prolonged usage in a continuous flow reactor, even if elevated temperatures were required to achieve good conversions, but that occasional reactivation of the catalyst might be required.”
Balthasart, who was making one of the starting materials of the instant process, the oxirane, in US ‘231 teaches reactors serially connected in a cascade, where products and unreacted reactants are removed from the heterogenous catalyst and added to the next serially linked reactor. As described in the abstract, “at least two reactors arranged in series, each of which contains a portion of the catalyst”. “In the process according to the invention, a plant comprising at least two epoxidation reactors arranged in series and connected together is used…..Needless to say, the plant may comprise more than two reactors connected in series.” [col. 2 lines 54 to col. 3 line 2]. Balthasart explains that by using this tandem reactor arrangement, “Specifically, this makes it possible to minimize the formation of by-products. The distillation serves to remove the oxirane as quickly as possible as it is formed in the reaction medium in order to prevent it from being in contact with the other constituents of the reaction medium and to prevent by-products from being thus formed.”
Balthasart does not mention the use of buffer tanks in the tandem reaction set up. Jokiel describes the use of buffer tanks in a tandem reactor set up in Figure 2 on page 2473. The buffer vessels allow additional control of product, which would allow further manipulation of product flows into distillation columns or other processing.
Ascertainment of the difference between the prior art and the claims
The instant claims differ from the prior art by the use of serially linked reactors or a holding or buffer tank.
Finding of prima facie obviousness
Rationale and Motivation
(MPEP 2142-2143)
By using serially linked reactors in claim 12-13, it is possible to isolate the catalyst from the product and reactivate it, without interrupting product flow. No catalyst has an infinite lifetime. The accepted view of a catalytic cycle is that it proceeds via a series of reactive species, be they transient transition state type structures or relatively more stable intermediates. Reaction of such intermediates with excess reagent or substrate can give rise to very stable complexes that are kinetically incompetent of sustaining catalysis. Removing the excess reagent would remove the over ligated complexes by reversing the reactions that led to their formation and would improve catalyst performance. A series of linked reactors is highly advantageous to limit the interval between regenerations by extending contact with regenerated or fresh catalyst for as long as possible in separate reaction vessels. Such a system is more tolerant of upsets, and blockage than a facility containing a single reactor which must be shut down periodically for catalyst replacement or reactivation. Furthermore, the catalyst consumption of the serially connected cascade reactors will be less than the single reactors for an equivalent total reactor volume. In this case Melendez has shown in the discussion on pages 3891-3893 that the catalyst is deactivated and can be reactivated with benzyl bromide or other quaternization reagents.
It would have been obvious to one of ordinary skill in the art at the time the claimed invention was made to use serially connected reactors to produce the instant invention. A reference is good not only for what it teaches by direct anticipation but also for what one of ordinary skill in the art might reasonably infer from the teachings. (In re Opprecht 12 USPQ 2d 1235, 1236 (Fed Cir. 1989); In re Bode 193 USPQ 12 (CCPA) 1976). In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103. From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Regarding the limitation of volume ratios it would be routing to adjust the volume ratios to improve process.
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 claims at issue 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); and 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 a nonstatutory double patenting ground provided the reference application or patent either is shown to be commonly owned with this application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The USPTO internet Web site contains terminal disclaimer forms which may be used. Please visit http://www.uspto.gov/forms/. The filing date of the application will determine what form 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 http://www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
6. Claims 1-16 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 5-7, 9, 11-19 of copending Application No. 17/771,223 in view of Balthasart 6,723,861 and Jokiel “Miniplant-Scale Evaluation of a Semibatch-Continuous Tandem Reactor System for the Hydroformylation of Long-Chain Olefins” Ind. Eng. Chem. Res. 2019, 58, 2471-2480. Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of the ‘223 patent application while broader in term of the catalyst are drawn to same process of the instant claims in claim 1 in claim 6. Claim 1 is just a 1 step process with the buffer tank of claim 16. Claim 13 has all the reactors of the copending claim 1. When viewing claim 1, it is obvious to use tandem reactions of the instant claims to produce the instant invention for the reasons as set forth above in Balthasart or the pending claim 13 of the ‘223. By using serially linked reactors, it is possible to isolate the catalyst from the product and reactivate it, without interrupting product flow. No catalyst has an infinite lifetime. The accepted view of a catalytic cycle is that it proceeds via a series of reactive species, be they transient transition state type structures or relatively more stable intermediates. Reaction of such intermediates with excess reagent or substrate can give rise to very stable complexes that are kinetically incompetent of sustaining catalysis. Removing the excess reagent would remove the over ligated complexes by reversing the reactions that led to their formation and would improve catalyst performance. A series of linked reactors is highly advantageous to limit the interval between regenerations by extending contact with regenerated or fresh catalyst for as long as possible in separate reaction vessels. Such a system is more tolerant of upsets, and blockage than a facility containing a single reactor which must be shut down periodically for catalyst replacement or reactivation. Furthermore, the catalyst consumption of the serially connected cascade reactors will be less than the single reactors for an equivalent total reactor volume.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
7. THIS ACTION IS MADE FINAL. 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 DAVID K O'DELL whose telephone number is (571)272-9071. The examiner can normally be reached on Monday - Friday 9:30 - 7:00 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton Brooks can be reached on 571-270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of an application may be obtained from Patent Center. Status information for published applications may be obtained from Patent Center. Status information for unpublished applications is available through Patent Center for authorized users only. Should you have questions about access to Patent Center, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free).
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) Form at https://www.uspto.gov/patents/uspto-automated- interview-request-air-form.
/DAVID K O'DELL/Primary Examiner, Art Unit 1621