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 1-8 were filed on 5/30/2024. In a preliminary amendment filed on the same day, claims 1-8 were canceled and claims 9-16 were newly filed. Claims 9-16 are pending and under examination.
Priority
The instant application was filed on 5/30/2024 and claims benefit of priority to:
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See filing receipt dated 10/11/2024. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Drawings
The drawings are objected to because Figure 1 does not provide a legend for all of the symbols used in the graph.
Corrected drawing sheets in compliance with 37 CFR 1.121(d) 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. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. 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 Objections
Claim 16 is objected to because of the following informalities: in line 1 of claim 16, the word “isoprenol” is misspelled as “isoproenol”. Appropriate correction is required.
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 12-14 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.
Claim 12, depending from independent claim 9, recites the limitation "the unreacted isoprenol stream” in lines 1-2 and “prior to combining the unreacted isoprenol stream with the fresh feed stream” in line 2. There is insufficient antecedent basis for this limitation in the claim. These limitations are introduced in claim 10.
Claim 13, depending from independent claim 9, recites the limitation “the unreacted isoprenol stream” in line 1. There is insufficient antecedent basis for this limitation in the claim. These limitations are introduced in claim 10.
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) 9-16 is/are rejected under 35 U.S.C. 103 as being unpatentable over Sauer (US 4440960, published on 4/3/1984, of record in the IDS filed on 6/19/2024) in view of Dyga (“Vapor-Liquid Equilibria and Chemical Equilibria in the System (Formaldehyde + Water + Isoprenol)” Industrial and Engineering Chemistry Research, published 3/15/2021, p. 4471).
Applicant claims a process for preparing 3-methyl-3-buten-1-al (isoprenal) or 3-methylbut-2-enal (prenal), by contacting 3-methyl-3- buten-1-ol (isoprenol) with a silver-containing heterogeneous catalyst in the presence of molecular oxygen wherein a weight ratio of formaldehyde to isoprenol is maintained at less than 0.04. Also see p. 1, lines 5-10 of the specification as filed.
Sauer claims a process for the continuous preparation of 3-alkyl-buten-1-als by oxidative dehydrogenation of 3-alkyl-buten-1-ols at from 320° to 650°C with (molecular) oxygen over a catalyst containing copper and/or silver, wherein, within one second after contact with the catalyst, the vaporous reaction mixture, which is at from 320° to 650°C., is brought into contact with a liquid comprising water and/or the condensed reaction mixture at from -20° to 50° C., and the 3-alkyl-buten-1-als are separated off from the resulting condensate. See abstract and claim 1:
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. When R is hydrogen and R’ is H2C=C(CH3)- these compounds correspond to prenal and prenol. When R and R’ together are H3C-C(CH3)= these compounds correspond to isoprenal and isoprenol. Sauer teaches that the catalyst is heterogeneous and present as a catalyst bed or as loose in the reactor. See col. 1, line 65-col. 2, line 7 and examples 1-3 (which refer to Fig. 1-3) in col. 3-6. Example 1 comprises the use of a bed of silver crystal catalyst crystals, which are interpreted to correspond to the claimed “full-metallic silver catalyst bodies” of claim 15. See col. 4, lines 1-14.
Sauer describes an example composition of the vaporous reaction mixture (product stream) in col. 2, lines 19-29.
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The product stream comprises 0.3 wt% of formaldehyde, 12.6 wt% of unreacted isoprenol, 34.5 wt% of isoprenal, and 6.7 wt% of prenal. After the condensation, Sauer teaches an example composition of the condensed product mixture in col. 2, lines 46-54:
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. The condensed product stream comprises 0.5 wt% of formaldehyde, 18.3 wt% of unreacted isoprenol, 50.1 wt% of isoprenal, and 9.6 wt% of prenal. Thus, all liquid components of the previous stream are concentrated because the non-condensable gases (isobutene, carbon monoxide, carbon dioxide, hydrogen, and nitrogen) are removed in the condensation step.
Sauer teaches “the yields in the case of the reaction of 3-methyl-but-3-en-1-ol are increased by about 10% by the process according to the invention. At the same time, the content of some of the atmosphere-polluting substances in the off-gas, such as carbon monoxide, hydrocarbons and formaldehyde, is significantly reduced, so that purification of the off-gases can be improved. Working up of the crude products is also simplified, because of the lower level of by-products, in particular of high-boilers and components which form high-boilers.” See col. 2, line 67-col. 3, line 8. Sauer further teaches: “there are other advantages of the process according to the invention, in respect of direct further processing of the crude products without prior working up, since the purity, for example measured according to color number, acid number and residue content of the crude products obtained are better by comparison, so that the secondary products can also be prepared in a better yield and purity.
These advantageous results were not to be expected, since 3-alkyl-buten-1-als, being unsaturated aliphatic aldehydes, are known to be very reactive substances (c.f. Ullmann, 4th edition, volume 7, page 118 et seq., especially 130-133). For example, they are readily oxidized to the corresponding carboxylic acids, form Diels-Alder adducts, readily polymerize and undergo a large number of addition reactions. Many of these reactions are accelerated by a polar medium and traces of acids, bases or salts.
It is therefore surprising that when the hot reaction gases are brought into contact with the finely divided condensing liquid, by-product formation is not increased since, compared with the process in German Laid-Open Application DOS No. 2,715,209, a significantly greater contact area of non-condensing reactive components in the reaction gas, such as oxygen, hydrogen, carbon monoxide, formaldehyde and isobutene, is presented to the 3-alkyl-buten-1-al, and water and other concomitant substances which promote by-product formation, such as acids, are also present. An increase in the formation of by-products was to be expected particularly, in the preferred embodiment in which recycled aqueous product solution is used as the condensing liquid, since the very reactive unsaturated aldehyde is continually being exposed to the hot reaction gases whilst it is in the form of finely divided droplets, a form which greatly promotes reaction”. See col. 3, lines 16-52.
Therefore, Sauer teaches that formaldehyde is an undesired by-product in the reaction and that there is no motivation to include it in the reactant stream comprising isoprenol. Sauer does not explicitly teach that a weight ratio of formaldehyde to isoprenol of less than 0.04 is maintained in the reactant stream. Nor does Sauer explicitly teach where the formaldehyde in the vaporous product stream is coming from.
Dyga teaches that isoprenol is produced from aqueous formaldehyde and isobutene and is separated by distillation from mixtures containing formaldehyde, water, and isobutene (claim 16). Dyga also teaches that as formaldehyde forms oligomers with both water and isoprenol, these mixtures are complex reaction systems which are not easy to separate. Therefore, Dyga used experimental data to extend a physical-chemical model of the system to simplify the separation. See abstract and introduction section. Dyga also teaches that an alternative to this chemical isoprenol process, also bio-synthetic routes for the production of isoprenol were developed recently. See first column of introduction section. Dyga teaches that “the system (water + isoprenol) shows a low-boiling azeotrope and a miscibility gap in the liquid phase, that is, heteroazeotropic behavior. The system (formaldehyde + isoprenol) shows a high-boiling azeotrope at low pressures, which vanishes above about 92 kPa.” See conclusions section on p. 4481-4482. Therefore, Dyga teaches conditions under which the three components can be separated from each other using at least two distillations (claim 11).
It would have been prima facie obvious to combine the teachings of Sauer and Dyga to arrive at the 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 exclude formaldehyde from the reactant isoprenol stream, such that the reactant stream comprises 100 wt% isoprenol, because Sauer teaches that formaldehyde is an impurity of the product mixture and that there is no benefit to it being present during the reaction. Further, the desired isoprenal product would then have to be purified to remove the impurity which is further undesirable. Sauer does not explicitly teach what the concentration, if any, of formaldehyde is in the reactant stream fed to the reactor. Sauer only teaches that formaldehyde is present in the vaporous product stream after the reaction between the gaseous reactant stream and oxygen in reactor. Dyga is cited to teach that it is known that the reaction between formaldehyde and isobutene is a well-known method to prepare isoprenol, such that traces of formaldehyde may be present in the reactant stream. However, Dyga also teaches that alternative bio-synthetic methods are known which would avoid the use of formaldehyde as a reagent such that none would be expected to be in the reactant stream of isoprenol. Further, even if formaldehyde impurities are expected in the reactant stream of isoprenol because of how the isoprenol is prepared, Dyga teaches a model for the efficient separation of formaldehyde from isoprenol. Therefore, Dyga teaches at least two methods for avoiding formaldehyde as an impurity in a reactant isoprenol stream which may be utilized by the skilled artisan to obviate the presence of unwanted formaldehyde in the reactant stream of Sauer. As Sauer teaches it is undesirable to have formaldehyde present in the reaction, the skilled artisan would have been motivated to use a source of isoprenol having as little formaldehyde present as possible, as taught is possible by Dyga, which falls within the claimed range of “less than 0.04”. Also see MPEP 2144.05.
Regarding claim 10, Sauer teaches that the liquid reaction products (8 in figs) obtained at the bottom of the quenching column (3 in figures) comprise isoprenal, prenal, and unreacted isoprenol. See col. 4, lines 58-66, col. 5, lines 43-49, and col. 6, lines 25-30. Sauer teaches that a portion of this liquid is separated and recycled back to reactor as the quenching liquid (10 in figures), below the catalyst bed (2 in figures). See examples. Sauer also teaches that the liquid condensates (8 in figs) are worked up, in order to separate the (iso)prenals in a conventional manner, for example by fractional distillation. Sauer teaches that the (iso)prenals are lower-boiling compared to the unreacted isoprenol, such that they are easily separated from one another. See col. 2, lines 55-66. Therefore, it would be prima facie obvious to collect the recovered unreacted isoprenol from the distillation and reuse it as a source of isoprenol in the reaction in order to increase the efficiency of the reaction.
Regarding claims 12-13, Sauer does not explicitly teach removing formaldehyde from any of the sources of isoprenol. However, Dyga teaches that isoprenol and formaldehyde can be separated by distillation. As Sauer teaches that no formaldehyde should be introduced into the reactor then it would be prima facie obvious to distill any of the isoprenol streams in any combination to remove formaldehyde. Further, Sauer teaches that formaldehyde is present in the product mixture, which indicates it could be being formed during the reaction even if none is being added with the isoprenol and would need to be removed prior to recycling. Also see MPEP 2143(I)(B).
Regarding claim 14, Dyga teaches that “the system (water + isoprenol) shows a low-boiling azeotrope and a miscibility gap in the liquid phase, that is, heteroazeotropic behavior. The system (formaldehyde + isoprenol) shows a high-boiling azeotrope at low pressures, which vanishes above about 92 kPa.” See conclusions section on p. 4481-4482. Dyga teaches that in the chemical equilibria of a mixture of formaldehyde + water + isoprenol, that formaldehyde strongly prefers isoprenol to form high-boiling oligomers. The oligomers separated from lower-boiling water at atmospheric pressure (1 bar, which falls within the claimed range) in a first column to produce a bottoms stream comprising isoprenol and a distillate stream comprising at least water. Dyga then teaches at high pressure (above 92 kPa / 0.92 bar, which encompasses the claimed range) that formaldehyde can be separated from isoprenol to produce a distillate comprising aqueous formaldehyde and a second bottoms stream comprising isoprenol. See discussion of “System (Formaldehyde + Water + Isoprenol)” and “Chemical Equilibria” on p. 4478-4479 and abstract. Additionally, all of the data provided in Dyga would provide enough direction to the skilled artisan to be able to optimize the system to separate all of the components. Also see MPEP 2144.05. Dyga does not explicitly teach a final distillation of the isoprenol stream obtained from the second distillation, however, it would be prima facie obvious to conduct a final distillation to remove any high-boilers from the isoprenol to further purify the product. Isoprenol is obtained in the bottoms of the first and second column, so it is likely that high-boilers would be present which could be removed in a final column wherein isoprenol is the distillate. As discussed previously, it is also prima facie obvious to recover and recycle any unreacted isoprenol product to the reactant stream in order to increase the efficiency of the 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 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 9-13 and 15-16 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 38-57 of co-pending Application No. 19/489329 (‘329, reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because the independent claim of ‘329 are a broader version of the claimed process, wherein any heterogeneous catalyst may be used and wherein the weight ratio of any aldehyde to isoprenol is maintained to less than 0.04. However, formaldehyde, and its use to prepare isoprenol by reaction with isobutene (claim 16), is recited in claims 42, 44, 45, 51, 55, and 57 and a silver catalyst is recited in claims 46-48. Regarding claims 10-14, see claims 45, 52, and 53.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 9-13 and 15-16 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 18-34 of co-pending Application No. 19/115825 (‘825, reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘825 recite a process which requires the instantly claimed process. See claims 30-33. Further regarding claims 10-13, as the claims of ‘825 teach the level of formaldehyde should be controlled in the reactant stream, then it would be prima facie obvious to distill any of the isoprenol streams in any combination to remove formaldehyde. It is further obvious to recover and recycle unreacted reactants in order to provide a more efficient reaction.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 9-13 and 15-16 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 21-40 of co-pending Application No. 18/874169 (‘169, reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘169 recite a process which requires the instantly claimed process. See claims 33-38. Further regarding claims 10-13, as the claims of ‘169 teach the level of formaldehyde should be controlled in the reactant stream, then it would be prima facie obvious to distill any of the isoprenol streams in any combination to remove formaldehyde. It is further obvious to recover and recycle unreacted reactants in order to provide a more efficient reaction.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claim 10 is rejected on the ground of nonstatutory double patenting as being unpatentable over:
claims 38-57 of co-pending Application No. 19/489329 (‘329, reference application);
claims 18-34 of co-pending Application No. 19/115825 (‘825, reference application); or
claims 21-40 of co-pending Application No. 18/874169 (‘169, reference application), as applied above, and further in view of Dyga (“Vapor-Liquid Equilibria and Chemical Equilibria in the System (Formaldehyde + Water + Isoprenol)” Industrial and Engineering Chemistry Research, published 3/15/2021, p. 4471).
The claims of ‘329, ‘825, and ‘169 teach at least one of the distillations in claim 14, but not the entire sequence. The teachings of Dyga were discussed in the previous section and are incorporated by reference herein.
It would have been prima facie obvious to arrive at the claimed invention based on the teachings of the claims of ‘329, ‘825, or ‘169 and Dyga with a reasonable expectation of success before the effective filing date of the claimed invention. Dyga provides all of the information needed to arrive at the claimed series of distillations using experimental and modeling data. Therefore, the skilled artisan could predictably arrive at the distillation sequence claimed based on the direction in Dyga. ‘329, ‘825, and ‘169 Also see MPEP 2144.05. Dyga does not explicitly teach a final distillation of the isoprenol stream obtained from the second distillation, however, it would be prima facie obvious to conduct a final distillation to remove any high-boilers from the isoprenol to further purify the product. Isoprenol is obtained in the bottoms of the first and second column, so it is likely that high-boilers would be present which could be removed in a final column wherein isoprenol is the distillate. As discussed previously, it is also prima facie obvious to recover and recycle any unreacted isoprenol product to the reactant stream in order to increase the efficiency of the process.
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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/AMY C BONAPARTE/ Primary Examiner, Art Unit 1692
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