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 12/01/2023 and no preliminary amendment was filed.
Claims 1-20 are currently pending and under examination.
Priority
The instant application claims domestic benefit to provisional application no. 63385875 filed on 12/02/2022.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 06/03/2024 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement has been considered by the examiner.
Drawings
The drawings are objected to as failing to comply with 37 CFR 1.84(p)(4) because reference character “132” in Fig. 1A and Fig. 1B. has been used to designate both hydrogen and hydrogenation product (see 0072). 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. 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.
The drawings are objected to as failing to comply with 37 CFR 1.84(p)(5) because they do not include the following reference sign(s) mentioned in the description: reference character 236, disclosed in paragraphs 0075 and 0076 are not present in Fig. 2A, 2B, or 2C. 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. 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.
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: reference character 215, shown in Fig. 2A, is not disclosed in the specification. 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.
Specification
The use of the term Raney™, which is a trade name or a mark used in commerce, has been noted in this application. The term should be accompanied by the generic terminology; furthermore the term should be capitalized wherever it appears or, where appropriate, include a proper symbol indicating use in commerce such as ™, SM , or ® following the term.
Although the use of trade names and marks used in commerce (i.e., trademarks, service marks, certification marks, and collective marks) are permissible in patent applications, the proprietary nature of the marks should be respected and every effort made to prevent their use in any manner which might adversely affect their validity as commercial marks.
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 9 and 18 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.
Claims 9 and 18 both contain a period in the body of the claim after the phrase “dehydration cleavage reaction zone.” The claims are indefinite because it is not clear whether the recitation following the period is encompassed by the claim scope. Furthermore, each claim begins with a capital letter and ends with a period. Periods may not be used elsewhere in the claims except for abbreviations (see MPEP 608.01(m)).
Regarding the interpretation of claims 9 and 18, the period will be interpreted as a comma with the rest of the claim after the period being encompassed by the claim scope.
Claim 11 is 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 11 contains the trademark/trade name Raney™. Where a trademark or trade name is used in a claim as a limitation to identify or describe a particular material or product, the claim does not comply with the requirements of 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph. See Ex parte Simpson, 218 USPQ 1020 (Bd. App. 1982). The claim scope is uncertain since the trademark or trade name cannot be used properly to identify any particular material or product. A trademark or trade name is used to identify a source of goods, and not the goods themselves. Thus, a trademark or trade name does not identify or describe the goods associated with the trademark or trade name. In the present case, the trademark/trade name is used to identify/describe a Ni hydrogenation catalyst and, accordingly, the identification/description is indefinite.
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.
Claims 1 and 3-11 are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (NPL, published 03/25/2020, PTO-892) in view of U.S. Patent No. 5,462,971 (‘971, published 10/31/1995, PTO-892).
Liu et al. teaches a one-pot synthesis hydrogenolysis of related alcohols over a tungsten-modified platinum on silica catalyst. The one-pot hydrogenolysis of Liu et al. is being interpreted by the examiner as corresponding to a dehydration-hydrogenation cascade reaction. Diols are widely used as co-monomers in polymer formation, and the preparation of ethylene glycol, for example, from cellulose and propanediols (PrDs) (glycerol selective hydrogenolysis to 1,2-PrD and 1,3-PrD) via biomass-based hydroconversion is available using heterogeneous metal catalysis (see paragraph 1). The optimized Pt–WOx/SiO2 (4 wt% Pt, W/Pt = 0.25) catalyst was applied to the hydrogenolysis of related alcohols (Table 2). First, the catalyst and water solvent were added. A desired amount of substrate was added. Once the temperature was increased to 413 K (reaction temperature, corresponds to 139.85 °C), the reactor was pressurized with H2 rapidly to 8 MPa and defined as 0 h. The standard reaction was carried out in the following conditions: initial hydrogen pressure at 8.0 MPa (8000 KPa), reaction temperature at 413 K (139.85 °C), reaction time for 24 h, 0.5 g (4.8 mmol) of 1,4-anhydroerythritol, 4 g of water, and 200 mg of 4 wt% Pt-WOx/SiO2 (41 [Symbol font/0x6D]mol Pt, W/Pt = 0.25). Some of the parameters were adjusted to optimize catalytic performance (see Activity Test, Supplemental Information). Regarding Table 2, specifically entries 12 and 13, 1,2- and 1,3-propanediol are reacted with a catalyst, water, and hydrogen gas to form propanol in 88 and 96%, respectively, through a one-pot
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reaction. Entry 12 also shows other C3 hydrocarbons including 2-propanol, acetone, and propane making up a total of about 12%.
The teachings of Liu et al. differs from that of the instantly claimed invention in that Liu et al. does not teach forming a product stream comprising propionaldehyde, a dioxolane component, and a dioxane component as required by instant claim 1.
‘971 teaches a process for the fluid bed cracking of polyether polyols to volatile lower molecular weight products through a process for reclaiming a poly ether polyol comprising the steps of: (a) heating the polyether polyol and a zeolite-containing particulate catalyst in a fluidized bed reaction zone at a temperature effective to produce a volatile organic component, and a spent catalyst component having carbon deposited thereon; (b) withdrawing a first stream comprising the volatile organic component from the reaction zone; (c) withdrawing a second stream comprising spent catalyst, and (d) heating the second stream in a regeneration zone in the presence of oxygen at a temperature effective to convert the carbon to carbon dioxide and water and to regenerate the catalyst (see Summary of the Invention). A distinct advantage of the process of this invention is that mixtures of polyether polyols polymers may be utilized as the feed. Another advantage of the invention is that thermo plastic polymers such as a Markush group including polypropylene may also be employed as admixtures with the polyether polyols polymer, since such thermoplastics, thermosets and rubbers will be successfully cracked or converted to useful volatile organic compounds simultaneous with transformation of the polyether polyols polymer (see Detailed Description of the Invention). Zeolite containing group 5A elements, especially phosphorus containing zeolite, are particularly preferred for use since it has been unexpectedly found that this class of zeolite is very tolerant of steam and tends to retain an unusually high degree of activity and selectivity in the presence of steam. Also suitable for use will be zeolite catalysts loaded or doped with Group VIII metals such as platinum and palladium to help carry out secondary functions such as hydrogenation or hydrogenolysis in addition to the basic cracking reaction (see second to last paragraph of column 3). If desired, a catalyst separation zone may be positioned such that products exiting the reaction zone are treated so as to remove any catalyst that may have been inadvertently carried over and to return this catalyst to the reaction zone (see column 5, paragraph 2). In the following examples polyether polyol was cracked at elevated temperatures and the product distribution determined. The Table 1 data demonstrates the usefulness of catalysts for converting polyols to light products, especially to propionaldehyde. The pre-mix method appears to be more efficient in converting the polyol, including lower MW polyol, to propionaldehyde. This may be due to better contact between the feed and the catalyst. Addition of 10 vs. 33 mol% steam to the nitrogen feed is preferred. The lower mol % steam may minimize saturation of the catalyst's active sites with absorbed water as opposed to polyol and its derivatives. Catalyst A contains approximately 15 wt % HZSM-5 and 3 wt % P within a binder. The Table II data demonstrates the usefulness of adding 10 mole % steam to the nitrogen feed. The steam may increase the number of Brönstead acid sites and thus the catalyst's activity. An optimal temperature of 350 °C to 450 °C is demonstrated. The Table III data demonstrates that SAPOs and metal APSOs may be used in place of HZM-5. The Table IV data demonstrate that lower reaction temperatures and the use of steam favor production of propylene glycol and dipropylene glycol which are extremely valuable products.
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Although Liu et al. does not teach the intermediates from the dehydration product, it would have been prima facie obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art that the intermediates produced after dehydration of a polyol would contain propionaldehyde, dioxolane, and dioxane based on the teachings of ‘971. One of ordinary skill in the art would have a reasonable expectation of success because both references teach the dehydration of polyols using an electrophilic acid catalyst.
Regarding instant claim 4, ‘971 teaches example 3 in Table 1 containing 81.6 wt% propionaldehyde, 2.3 wt% dioxolane component, and 4.2 wt% dioxane. While the teachings of ‘971 regarding the propionaldehyde and dioxolane do not within the range given in instant claim 4, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close (see MPEP 2144.05(I)). Regarding water, ‘971 teaches that water is removed in another stream and will be interpreted by the examiner to be 0 wt%.
Regarding instant claims 5-8, Liu et al. teaches entry 12 containing 88% 1-propanol (a propylene precursor), 9% 2-propanol (a propylene precursor), <1% acetone (a propylene precursor), and 2% propane all corresponding to organics other than water. This corresponds to 0 wt% water and 100 wt% organics other than water in the product stream with 1-propanol being 88 wt%, and other C3 hydrocarbons being approximately 12 wt%.
Regarding instant claim 9, ‘971 teaches regenerating the spent catalyst, the spent catalyst being interpreted as a product of the reaction taught by ‘971, equivalent to the instant dehydration cleavage, in steps (c) and (d). The catalyst is regenerated and returned to the reaction to be reused.
Claims 12-14 are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (NPL, published 03/25/2020, PTO-892) U.S. Patent No. 5,462,971 (‘971, published 10/31/1995, PTO-892), as applied to claim 1 above, and further in view of Taheri et al. (US20140179972A1, published 06/26/2014, PTO-892).
The combined teachings of Liu et al. and ‘971 were discussed above.
The combined teachings of Liu et al. and ‘971 differ from that of the instantly claimed invention in that the combined teachings of Liu et al. and ‘971 do not teach adding the hydrogenation product stream (propanol) to a dehydration reaction zone in the presence of a second solid acid catalyst to form a third reaction mixture; and reacting the third reaction mixture at a temperature in the range of from 20 °C to 600 °C, a pressure in the range of from 15 psig (103 kPa(g)) to 500 psig (689 kPa(g)), or a combination thereof, to form a dehydration product stream comprising propylene as required by instant claim 12. Liu et al. and ‘971 does not teach wherein the hydrogenation product stream (propanol) is added to the dehydration reaction zone at a weight hourly space velocity (WHSV) in the range of from 0.1 h-1 to 100 h-1 as required by instant claim 13. Liu et al. and ‘971 does not teach wherein the second solid catalyst component comprises a Markush group of solid acid catalysts including aluminum oxide.
Taheri et al. teaches a process for the catalytic dehydration of propanol to propylene. Propylene is the second most important raw material in the petrochemicals industry after ethylene. It is the primary feedstock in such diverse materials as polypropylene, propylene oxide, propylene glycol, acrylonitrile, epichlorohydrin, etc. (see 0004). A hydrous or anhydrous propanol stream (analogous to the instant hydrogenation product stream) is first vaporized and preheated in a heat exchanger. Propanol is added to each stage at a rate of between 0.01 to 10 kg per hour per kg catalyst (also known as the WHSV) and has a weight ratio of between 0.0 to 0.06 and preferably between 0.01 to 0.1 to the weight of the inert gas at the inlet to each stage. Within each stage as optimized according to the present invention, the operating temperature is from 250 °C to 550 °C and preferably from 300 °C to 500 °C at the inlet to each stage and wherein the outlet temperature of each stage is maintained at 200 °C to 500 °C and preferably from 300 °C to 450 °C at operating pressure of each stage is from 2 bar(g) to 50 bar(g) (about 29-725 psi(g)) and preferably from 4 bar(g) to 40 bar(g) (see 0032 and 0033). The catalyst employed in this process may be alumina, silica-alumina, zeolites, or other suitable catalysts as are described in the patent literature (see 0047).
It would have been obvious before the effective filing date of the claimed invention to combine the teachings of Liu et al. and ‘971 with the teachings of Taheri et al. by dehydrating the propanol, as taught by Taheri et al., that resulted from the process, as taught by Liu et al. and ‘971, to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to combine the teachings of Liu et al. and ‘971 with the teachings of Taheri et al. because the combination of the steps, as taught by Liu et al., ‘971, and Taheri et al. would allow for recycling of propylene monomers from propylene polyols. One of ordinary skill in the art would have a reasonable expectation of success because the dehydration of propanol to propylene is a highly efficient, well-established process.
Claims 15-16 are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (NPL, published 03/25/2020, PTO-892) in view of U.S. Patent No. 5,462,971 (‘971, published 10/31/1995, PTO-892), as applied to claim 1 above, and further in view of Purvis et al. (NPL, published 03/14/2011, PTO-892).
The combined teachings of Liu et al. and ‘971 were discussed above.
The combined teachings of Liu et al. and ‘971 differ from that of the instantly claimed invention in that the combined teachings of Liu et al. and ‘971 do not teach further comprising adding an organic waste stream, comprising one or more propylene polyols and a first content of one or more impurities harmful to the dehydration cleavage catalyst, to a guard reaction zone to form the feed stream comprising one or more propylene polyols, as required by instant claim 15. The combined teachings of Liu et al. and ‘971 do not teach wherein the impurities comprise a Markush group including amines.
Purvis et al. teaches ethylene units have traditionally supplied polymer grade ethylene and propylene monomers to polyethylene (PE) and polypropylene (PP) process units. Any additional purification of these monomers to remove catalyst poisons has typically been carried out in the polyolefin units. Polyolefin units vary in the process technologies employed (i.e., gas, slurry or solution phase) and in the types of catalysts used (i.e., Ziegler Natta, advanced Ziegler Natta, Chromium Oxide (Phillips type) and more recently metallocene or single site). Catalyst can be used in heterogeneous or homogeneous forms. Nearly all of the catalyst currently employed in polyolefin production are susceptible to poisoning from heteroatoms (O, N and S). Also, the latest co-catalysts used with metallocene or simple site catalysts, such as modified aluminoxane (MAO), is also susceptible to poisoning. Catalyst poisons consume catalyst and co-catalyst with the result that operating costs and the residual concentration of the catalysts in the final product increase. In addition, polyolefin units must also purge impurities brought into the units by the feedstocks (methane, ethane, propane, etc.) and also generated within the polyolefin unit itself, in some cases from the deactivation of catalysts and co-catalysts. These purge streams can be managed internally within the polyolefin unit or recycled back to the ethylene unit.
It would have been obvious before the effective filing date of the claimed invention for a person having ordinary skill in the art to be motivated to remove heteroatom containing impurities from a propylene recycling stream, as taught by Purvis et al., prior to performing the rest of the process, as taught by Liu et al. and ‘971, to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to be motivated to remove heteroatom impurities because, as taught by Purvis et al., polyolefin production catalysts are susceptible to heteroatom poisoning. One of ordinary skill in the art would have a reasonable expectation of success because amines and polyols (due to their different chemical properties) are highly responsive to standard separation techniques.
Claims 17-18 are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (NPL, published 03/25/2020, PTO-892) in view of U.S. Patent No. 5,462,971 (‘971, published 10/31/1995, PTO-892) in further view of Katritzky et al. (NPL, published 11/01/1997, PTO-892).
The teachings of Liu et al. were discussed above.
The teachings of Liu et al. differ from that of the instantly claimed invention in that Liu et al. does not teach a dehydration cleavage product stream comprising propionaldehyde, a dioxolane component, and a dioxane component; withdrawing the dehydration cleavage product as a first hydrogenation feed or routing the dehydration cleavage product to a first distillation column to produce a dehydration cleavage product overhead stream and a dehydration cleavage product bottoms stream and withdrawing the dehydration cleavage overhead product as a second hydrogenation feed and withdrawing the hydrogenation product as a first propanol-containing product or routing the hydrogenation product to a second distillation column to produce a hydrogenation product overhead stream and a hydrogenation product bottoms stream and withdrawing the hydrogenation overhead product as a second propanol-containing product; wherein at least one of the second hydrogenation feed and the second propanol-containing product is formed during the process. The teachings of Liu et al. differ from that of the instantly claimed invention in that Liu et al. does not teach adding at least a portion of the first hydrogenation feed or the second hydrogenation feed to the dehydration cleavage reaction zone as required by instant claim 18.
The teachings of ‘971 were discussed above.
Katritzky et al. teaches normal boiling points for organic compounds. The boiling point of 1,2-propylene glycol is 460.8 K. The boiling point of 1,3-propylene glycol is 487.6 K. The boiling point of propanol is 370.4 K. The boiling point of propionaldehyde is 321.1 K. The boiling point of 1,4-dioxane is 374.1 K. The boiling point of 1,3-dioxane is 378.6 K.
Although Liu et al. does not teach the intermediates from the dehydration product, it would have been prima facie obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art that the intermediates produced after dehydration of a polyol would contain propionaldehyde, dioxolane, and dioxane based on the teachings of ‘971. One of ordinary skill in the art would have a reasonable expectation of success because both references teach the dehydration of polyols using an electrophilic acid catalyst. It would have been obvious before the effective filing date of the claimed invention to regenerate the spent catalyst, which is interpreted by the examiner to be a portion of the instant first hydrogenation feed, as taught by ‘971, to the beginning of the reaction taught by ‘971, being interpreted as equivalent to the instant dehydration cleavage reaction, to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to recycle the spent catalyst because this improves the catalyst economics. One of ordinary skill in the art would have a reasonable expectation of success because ‘971 teaches a successful example of catalyst regeneration. It would have been prima facie obvious for one of ordinary skill to be motivated to route the dehydration cleavage product to a first distillation column because, as taught by Katritzky et al., propionaldehyde has the lowest boiling point and would boil first to produce the instant dehydration overhead stream which could then be the instant second hydrogenation feed. One of ordinary skill in the art would have a reasonable expectation of success because distillation is a common purification technique.
Claims 19-20 are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (NPL, published 03/25/2020, PTO-892) in view of U.S. Patent No. 5,462,971 (‘971, published 10/31/1995, PTO-892) in further view of Katritzky et al. (NPL, published 11/01/1997, PTO-892), as applied to claim 17 above, and in further view of Taheri et al. (US20140179972A1, published 06/26/2014, PTO-892).
The combined teachings of Liu et al., ‘971, and Katritzky et al. were discussed above.
The combined teachings of Liu et al., ‘971, and Katritzky et al. differ from that of the instantly claimed invention in that the combined teachings of Liu et al., ‘971, and Katritzky et al. does not teach further comprising: a) adding the first propanol-containing product or the second propanol-containing product to a dehydration reaction zone in the presence of a dehydration catalyst to form a third reaction mixture; and b) reacting the third reaction mixture at a temperature in the range of from 20 °C to 600 °C, a pressure in the range of from 15 psig (103 kPa g) to 500 psig (689 kPa g), or a combination thereof, to form a dehydration product stream comprising propylene as required by instant claim 19. The combined teachings of Liu et al., ‘971, and Katritzky et al. does not teach further comprising: a) withdrawing the dehydration product as a first propylene-containing product; or b) routing the dehydration product to a third distillation column to produce a dehydration product overhead stream and a dehydration product bottoms stream and withdrawing the dehydration overhead product as a second propylene-containing product, as required by instant claim 20.
The teachings of Taheri et al. were discussed above.
It would have been obvious before the effective filing date of the claimed invention to combine the teachings of Liu et al. and ‘971 with the teachings of Taheri et al. by dehydrating the propanol, as taught by Taheri et al., that resulted from the process, as taught by Liu et al. and ‘971 in further view of Katritzky et al., to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to combine the teachings of Liu et al., ‘971, and Katritzky et al. with the teachings of Taheri et al. because, as taught by Taheri et al., propylene is the primary feedstock in such diverse materials. One of ordinary skill in the art would have a reasonable expectation of success because the dehydration of propanol to propylene is a highly efficient, well-established 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 1-20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of copending Application No. 18/526362 (‘362) in view of Hayashi et al. (NPL, published 01/06/2016, PTO-892).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Although the claims at issue are not identical, they are not patentably distinct from each other because ‘362 recites:
1. A process comprising: a) adding a feed stream comprising one or more propylene polyols, hydrogen, and optionally water, to a catalytic conversion reaction zone in the presence of a first solid acid catalyst component and a hydrogenation catalyst component to form a first reaction mixture; and b) reacting the first reaction mixture at a temperature in the range of from 20 °C to 600 °C, a pressure in the range of from 100 psig (689 kPa(g)) to 1,500 psig (10,340 kPag), or a combination thereof, to form a hydrogenation product stream comprising a propanol component.
2. The process of claim 1, wherein the feed stream is added to the catalytic conversion reaction zone at a weight hourly space velocity in the range of from 0.1 h-1 to 100 h-1.
3. The process of claim 1, wherein the one or more propylene polyols comprise propylene glycol, di-propylene glycol, tri-propylene glycol, tetra-propylene glycol, or a combination thereof.
4. The process of claim 1, wherein the catalytic conversion product comprises 0 wt% to 90 wt% water and 10 wt% to 100 wt% organics other than water, wherein weight percentages are based on the total weight of the catalytic conversion product.
5. The process of claim 4, wherein the organics other than water comprise 1-propanol in the range of from 50 wt% to 90 wt% and other C3 hydrocarbons in the range of from 10 wt% to 50 wt%, wherein weight percentages are based on the total weight of the organics other than water.
6. The process of claim 1, wherein the catalytic conversion product stream further comprises a propylene precursor component.
7. The process of claim 6, wherein the propylene precursor component comprises 1 -propanol,2-propanol, propionaldehyde, acetone, C3 dioxanes, C3 dioxolanes, propylene glycol, hydroxyacetone, or a combination thereof.
8. The process of claim 1, further comprising adding at least a portion of the catalytic conversion product to the catalytic conversion reaction zone.
9. The process of claim 1, wherein the first solid acid catalyst component comprises a zeolite component, an alumina silicate component, aluminum phosphate, zirconium sulfate, titanium sulfate, supported phosphoric acid, one or more supported tungsten oxides, supported tungstosilicic acid, supported phosphomolybdic acid, aluminum oxide, niobium oxide, one or more polystyrene sulfonate acidic resins, sulfonate functionalized support, tethered organic sulfonic acids, acidic clays, or a combination thereof.
10. The process of claim 1, wherein the hydrogenation catalyst component comprises sulfided NiMo/Al2, sulfided CoMo/Al2 Ni/SiO2, Ni/Al2O3, Raney Ni, Cu/SiO2, Cu/Al2 Pd/SiO2, Pd/Al2O3, Pd/C, Pt/SiO2, Pt/Al2O3, Ru/C, In2O3In2O3/Al2O3, In2O3/SiO2, or a combination thereof.
11. The process of claim 1, wherein: a) the first solid acid catalyst component is a first discrete catalyst, and the hydrogenation catalyst component is a second discrete catalyst; or b) a hybrid catalyst comprises the first solid acid catalyst component and the hydrogenation catalyst component.
12. The process of claim 1, further comprising: a) adding the catalytic conversion product stream to a dehydration reaction zone in the presence of a second solid acid catalyst to form a second reaction mixture; and b) reacting the second reaction mixture at a temperature in the range of from 200C to 6000C, a pressure in the range of from 15 psig (103 kPag) to 500 psig (689 kPag), or a combination thereof, to form a dehydration product stream comprising propylene.
13. The process of claim 12, wherein the catalytic conversion product stream is added to the dehydration reaction zone at a weight hourly space velocity in the range of from 0.1 h-1 to 100 h-1.
14. The process of claim 12, wherein the second solid catalyst component comprises a zeolite component, an alumina silicate component, aluminum phosphate, zirconium sulfate, titanium sulfate, supported phosphoric acid, one or more supported tungsten oxides, supported tungstosilicic acid, supported phosphomolybdic acid, aluminum oxide, niobium oxide, or a combination thereof.
15. The process of claim 1, further comprising adding an organic waste stream, comprising one or more propylene polyols and a first content of one or more impurities harmful to the first solid acid catalyst component and/or the hydrogenation catalyst component, to a guard reaction zone to form the feed stream comprising one or more propylene polyols.
16. The process of claim 15, wherein the impurities comprise amines, urethane, amides, other nitrogen containing hydrocarbons, organic bases, caustic, or a combination thereof.
17. A process comprising: a) adding a feed stream comprising one or more propylene polyols, hydrogen, and optionally water, to a catalytic conversion reaction zone in the presence of a first solid acid catalyst component and a hydrogenation catalyst component to form a first reaction mixture; b) reacting the first reaction mixture at a temperature in the range of from 20 °C to 600 °C, a pressure in the range of from 100 psig (689 kPag) to 1,500 psig (10,340 kPag), or a combination thereof, to form a catalytic conversion product stream comprising a propanol component; and c) adding the catalytic conversion product to a first distillation column to produce a catalytic conversion product overhead stream and a catalytic conversion product bottoms stream and withdrawing the catalytic conversion overhead product stream as a first conversion product.
18. The process of claim 17, further comprising adding at least a portion of the first conversion product to the catalytic conversion reaction zone.
19. The process of claim 17, further comprising: a) adding the first conversion product to a dehydration reaction zone in the presence of a second solid acid catalyst to form a second reaction mixture; and b) reacting the second reaction mixture at a temperature in the range of from 200C to 6000C, a pressure in the range of from 15 psig (103 kPag) to 500 psig (689 kPag), or a combination thereof, to form a dehydration product stream comprising propylene.
20. The process of claim 19, further comprising: a) withdrawing the dehydration product as a first propylene-containing product; or b) routing the dehydration product to a second distillation column to produce a dehydration product overhead stream and a dehydration product bottoms stream and withdrawing the dehydration overhead product as a second propylene-containing product.
The claims of ‘362 differs from that of the instantly claimed invention in that ‘362 does not recite different zones for the dehydration cleavage step and the hydrogenation step.
The teachings of Hayashi et al. were discussed above.
It would have been obvious before the effective filing date of the claimed invention to vary the elements of the pot economy, as taught by Hayashi et al., of the method, as claimed by ‘362, to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to vary the elements of the pot economy of the method because, as taught by Hayashi et al., pot economy is a promising green approach to contemporary synthesis and some intermediates, side-, or byproducts could be economically useful. One of ordinary skill in the art would have a reasonable expectation of success because ‘362 recites the same elementary reaction steps, reagents, and final products.
Conclusion
No claim is found allowable.
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/KRISTEN W BRADY/ Examiner, Art Unit 1692
/SCARLETT Y GOON/ Supervisory Patent Examiner, Art Unit 1693
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