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
This Final Office action is based on the 18/631125 application originally filed April 10, 2024.
Amended claims 5, 6, 8-13 and 17-24, filed March 31, 2026, are pending and have been fully considered. Claims 1-4, 7 and 14-16 have been canceled.
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) 5, 6, 8-13 and 15-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Lehtonen et al. (US 2005/0080304) hereinafter “Lehtonen” in view of Gough et al. (US 5,585,530) hereinafter “Gough”.
Regarding Claim 5
Lehtonen discloses in paragraph 0005, a process for the manufacture of a gasoline blending component containing sulphur-free paraffinic hydrocarbons from a feed mixture comprising olefinic hydrocarbons obtained from dimerization of butenes.
Lehtonen discloses in paragraph 0008, a hydrocarbon feed-stock containing 80-97 wt % of C8 olefins, 3-20 wt % of C12 olefins, 0.1-7 wt % of C9, C10, C11 and heavier>C12 olefins, and optionally minor amounts of lighter C6-C7 olefins, is used. The feed-stock may originate from an olefinic hydrocarbon mixture obtained from dimerization of butenes.
Lehtonen discloses in paragraph 0010, suitable hydrogenation catalysts to be used in the process according to the invention are noble metal catalysts on aluminum oxide support. Preferable noble metals are platinum and/or palladium, particularly preferably platinum. The content of the noble metal on the support is <1 wt %. In some cases the noble metal may be replaced with nickel.
Lehtonen discloses in paragraph 0016, a fixed-bed three-phase hydrogenation reactor and preferably a trickle-bed or pulse flow reactor is used. The reactor typically performs as a trickle-bed reactor with a more than two times fluid circulation stream when compared with fluid feed. This controls the rise of temperature in the reactor catalyst bed. In a trickle-bed reactor the catalyst is placed in a fixed bed and liquid olefin feed as well as gaseous hydrogen feed flow concurrently downwards through the bed. The preferable flow regimes for this three-phase flow are trickling and pulse flow regimes. Also other flow patterns of three-phase hydrogenation like counter current flow and concurrent up-flow are possible.
Lehtonen discloses in paragraph 0017, high hydrogen concentration in the first step is maintained with fluid circulation and by introducing fresh hydrogen to the first step. Recycled fluid is saturated with dissolved hydrogen. The advantage of high hydrogen concentration in the first step is that it favors olefin hydrogenation and breaking of the sulphur components and at the same time effectively reduces coke formation on the catalyst.
Lehtonen discloses in paragraph 0028, the hydrogen/olefin molar ratio is from 0.9 to 2.0, resulting in low hydrogen consumption. Low excess of hydrogen and mild operating conditions decrease hydrogen loss with vapor product and a hydrogen recycling compressor is not normally needed for hydrogen recovery.
Lehtonen discloses the process of hydrogenation of olefins but fails to further teach the heat of reaction of hydrogenation.
However, Gough discloses in column 2 lines 20-37, a process for the production of olefins comprising dehydrogenating at least one hydrogen-donor hydrocarbon that is essentially free from olefinic unsaturation, e.g. a paraffin, in the presence of a dehydrogenation catalyst and in the presence of at least one hydrogen-acceptor hydrocarbon that is more highly unsaturated than a mono-olefin, e.g. a diene and/or acetylene, under conditions effective to cause at least part of said hydrogen-donor hydrocarbon to be dehydrogenated and at least part of the hydrogen-acceptor to be hydrogenated. The amount of hydrogen-acceptor is such that there are 0.5 to 20 moles of said hydrogen-donor for each mole of hydrogen-acceptor. Preferably the amount of said hydrogen-acceptor hydrocarbon hydrogenated is such that the heat of hydrogenation of said hydrogen-acceptor hydrocarbon provides at least 25% of the heat required for dehydrogenation of said hydrogen-donor hydrocarbon.
Gough discloses in column 4 lines 65-67 and column 5 lines 1-6, although elevated temperatures are required, often necessitating preheating of the reactants, since the process is preferably operated such that at least 25% of the heat required for the dehydrogenation of the hydrogen-donor is supplied by hydrogenation of the hydrogen-acceptor, far less heat input is required than in dehydrogenation in the absence of the hydrogen-acceptor. Thus heat can be recovered from the products and by feed/effluent heat exchange used to provide most, if not all, of the heat required for the reaction.
In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
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 Claim 6
Lehtonen discloses in paragraph 0016, a fixed-bed three-phase hydrogenation reactor and preferably a trickle-bed or pulse flow reactor is used. The reactor typically performs as a trickle-bed reactor with a more than two times fluid circulation stream when compared with fluid feed. This controls the rise of temperature in the reactor catalyst bed. In a trickle-bed reactor the catalyst is placed in a fixed bed and liquid olefin feed as well as gaseous hydrogen feed flow concurrently downwards through the bed. The preferable flow regimes for this three-phase flow are trickling and pulse flow regimes. Also other flow patterns of three-phase hydrogenation like counter current flow and concurrent up-flow are possible.
Regarding Claims 8-10
Lehtonen discloses in paragraph 0028, the hydrogen/olefin molar ratio is from 0.9 to 2.0, resulting in low hydrogen consumption. Low excess of hydrogen and mild operating conditions decrease hydrogen loss with vapor product and a hydrogen recycling compressor is not normally needed for hydrogen recovery.
In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Regarding Claims 11 and 13
Lehtonen discloses in paragraph 0008, a hydrocarbon feed-stock containing 80-97 wt % of C8 olefins (linear and/or branched dibutenes), 3-20 wt % of C12 olefins (linear and/or branched tributenes), 0.1-7 wt % of C9, C10, C11 and heavier>C12 olefins, and optionally minor amounts of lighter C6-C7 olefins, is used. The feed-stock may originate from an olefinic hydrocarbon mixture obtained from dimerization of butenes.
Regarding Claims 7, 12, 17 and 18
Lehtonen discloses in paragraphs 0013 and 0014, the reaction temperature in the first step is in the range of 150-230℃ and the pressure is in the range of 20-70 bar. In the second step a higher reaction temperature is applied in the reactor than in the first step. The reaction temperature is in the range of 180-300℃ and the pressure is in the range of 20-70 bar.
Lehtonen discloses in paragraph 0018, the process in the first step one reactor or several reactors parallel with each other can be used, or the reactor can be divided into more than one reactor beds with a cooler between each reactor bed. By using inter-space coolers the amount of circulation stream can be decreased. The reaction heat can be removed from the process from the circulating stream by process exchangers whereby the reaction heat can be used for preheating of incoming feed-stock to the dimerization unit of butenes, or as an energy source for distillation columns of bottom boilers of dimerization unit of butenes, either directly or indirectly via utility system of the plant or site area. The heat can also be directly used to other process units at site.
Regarding Claims 19 and 20
Lehtonen discloses in paragraph 0010, suitable hydrogenation catalysts to be used in the process according to the invention are noble metal catalysts on aluminum oxide support. Preferable noble metals are platinum and/or palladium, particularly preferably platinum. The content of the noble metal on the support is <1 wt %. In some cases the noble metal may be replaced with nickel.
Claim(s) 21 and 24 is/are rejected under 35 U.S.C. 103 as being unpatentable over Lehtonen et al. (US 2005/0080304) hereinafter “Lehtonen” in view of Gough et al. (US 5,585,530) hereinafter “Gough” and further in view of Dai et al. (US 2002/0068843) hereinafter “Dai”.
Regarding Claims 21 and 24
Lehtonen discloses the process of claim 1 of the present invention but fails to further teach the catalyst layer of claims 21 and 24 of the present invention.
However, Dai discloses in 0022-0026, the selective hydrogenation catalyst of this invention for selectively hydrogenating unsaturated olefin comprises mainly the following active components loaded on a porous inorganic supporter: (1) at least one of Pt, Pd, Ni, Rh, Co, and Ru; (2) at least one of Ag, Cu, Zn, K, Na, Mg, Ca, Be, Sn, Pb, Sr, Ba, Ra, Fe, An, Zr, Mo, and Ge; (3) at least one of rare earth metals; and wherein the rare earth metal is selected from Sc, Y and Lanthanides including La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, and Lu.
Dai discloses in paragraph 0032, the porous inorganic supporter can be the well-known supporter in the prior art. For example, diatomaceous earth, spinel, SiO2, TiO2, Al2O3, or mixtures thereof. The preferred supporter is Al2O3 or SiO2; Its shape can be granular, gear-shaped, spherical, laminar or strip, preferably gear-shaped or spherical, more preferably gear-shaped (such a shape has an advantage of low bed pressure drop at high space velocity); its specific surface area is 1-200 m2/g. Dai further discloses the catalyst is a thin layer with a thickness of 1 to 30 µm.
It would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to apply a layer support, including the platinum or palladium of Dai and Lehtonen, in an amount of less than 500 µm in order to disperse uniformly on catalyst surface and forms a thickness of a thin layer.
Claim(s) 22 and 23 is/are rejected under 35 U.S.C. 103 as being unpatentable over Lehtonen et al. (US 2005/0080304) hereinafter “Lehtonen” in view of Gough et al. (US 5,585,530) hereinafter “Gough and further in view of Degnan et al. (US 2002/0107139) hereinafter “Degnan”.
Regarding Claims 22 and 23
Lehtonen discloses the process of claim 1 of the present invention but fails to further teach the catalyst layer of claims 22 and 23 of the present invention.
However, Degnan discloses in the abstract, a coated hydrogenation catalyst that includes a porous support material, an active metal component and a silica precursor. Degnan discloses in paragraph 0020, the catalysts have an active metal component, such as platinum anchored in a primarily siliceous environment, that can be modified in order to control its activity. The catalysts can use any of the zeolites used in hydrogenation catalysts to produce catalysts with anchored active metal components. The active metal component can be a noble metal or other metals, such a promoter, a modifier, a cation or a combination thereof. In addition to the noble metals, other metals such as nickel, cobalt, chromium, vanadium, molybdenum, tungsten, nickel-molybdenum, cobalt-nickel-molybdenum, nickel-tungsten, cobalt-molybdenum and nickel-tungsten-titanium can be used. The binder for the catalysts are conventionally a porous solid, usually alumina, or silica-alumina but other porous solids such as magnesia, titania or silica, either alone or mixed with alumina or silica-alumina may also be used, as convenient. Ideally, the catalysts also contain a zeolite as one of the components. The catalysts are formed before being contacted with the silica precursor (e.g., silicone or volatile silica compound).
It would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to apply the zeolite and/or silica support of Degnan to the hydrogenation catalyst of Lehtonen. The motivation to do so is to use a support material, zeolites and/or silica, that aids in coating catalysts that provide controlled dispersion and activity.
Response to Arguments
Applicant’s arguments directed to the newly submitted claimed amendments, filed March 31, 2026, with respect to the rejection(s) of claim(s) 5-13 and 17-18 under 35 USC 102(a)(1) Lehtonen et al. (US 2005/0080304) hereinafter “Lehtonen” have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of Lehtonen et al. (US 2005/0080304) hereinafter “Lehtonen” in view of Gough et al. (US 5,585,530) hereinafter “Gough.
Applicant's arguments directed Lehtonen et al. (US 2005/0080304) hereinafter “Lehtonen” failing to disclose the claimed olefin conversion due to Lehtonen only discloses 94% of all olefins, filed March 31, 2026, have been fully considered but they are not persuasive. It is maintained Lehtonen discloses the claimed amount of 99% olefins due to Lehtonen discloses in paragraph 0008, a hydrocarbon feed-stock containing 80-97 wt % of C8 olefins, 3-20 wt % of C12 olefins, 0.1-7 wt % of C9, C10, C11 and heavier>C12 olefins, and optionally minor amounts of lighter C6-C7 olefins, is used. The Total amount of olefins is in the range of approximately 76 to over 100 wt%. Therefore, it is maintained Lehtonen discloses the claimed olefin conversion amount.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Risch et al. (US 2005/0043575) discloses in the abstract, a process is disclosed for selectively removing isobutene and butadiene from a stream, the process comprising contacting the stream with a hydrogenation catalyst to hydrogenate butadiene and an oligomerization catalyst to oligomerize isobutene.
Suzuki et al. (US 2007/0161500) discloses in the abstract, a method for regenerating a hydrogenation catalyst without using alkanes and a diolefin purification plant comprising an equipment which is used in this method and is simpler than ever. The first method comprises a contact step of contacting a composition for regeneration containing 50% by mass or more of an olefin having the carbon number of from 4 to 8 with the hydrogenation catalyst. The hydrogenation catalyst can be a hydrogenation catalyst used in hydrogenation of an acetylenic compound contained in a starting composition containing at least one diolefin having the carbon number of from 4 to 8.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LATOSHA D HINES whose telephone number is (571)270-5551. The examiner can normally be reached Monday thru Friday 9:00 AM - 6:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Prem Singh can be reached at 571-272-6381. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Latosha Hines/Primary Examiner, Art Unit 1771
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