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 Objections
Claim 17 is objected to under 37 CFR 1.75 as being a substantial duplicate of claim 5. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m).
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 1-3 and 5-19 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-18 of U.S. Patent No. 12,084,622. Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims drawn to a method for converting C2+ olefins to higher number olefins useful in producing isoparaffinic composition. There are minor differences and such differences would have been obvious to one of skill in the art.
Claims 1-3 and 5-19 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of U.S. Patent No. 12,012,562. Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims drawn to a method for converting C2+ olefins to higher number olefins useful in producing isoparaffinic composition. There are minor differences and such differences would have been obvious to one of skill in the art.
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.
Claims 1-3, 5-8, 10, and 15-19 are rejected under 35 U.S.C. §103 as being unpatentable over Lilga et al. (US 2017/0369804 A1) in view of Deimund et al. (US 2020/0056106 A1) and Peters (US 2014/0051897 A1).
Regarding claims 1 and 15, Lilga teaches a process for producing jet-range hydrocarbons by oligomerizing an ethylene-containing feedstock in a first oligomerization stage to produce C4+ olefins, further oligomerizing the intermediate olefins in a second oligomerization stage, hydroprocessing the oligomerization products with hydrogen, and recovering hydrotreated jet-range hydrocarbons suitable for aviation fuel blending (Lilga, Fig. 13; ¶¶ [0140]-[0144]). Lilga further teaches recycling light olefin fractions to increase conversion of ethylene into fuel-range hydrocarbons (Lilga ¶¶ [0142]-[0144]). Thus, Lilga teaches a two-stage ethylene oligomerization process followed by hydrotreating to produce a jet-range blendstock.
Lilga, however, does not expressly teach that the first oligomerization unit comprises a serial reactor and a lights-removal column, does not expressly teach purification of the intermediate olefin stream prior to the second oligomerization stage, and does not expressly teach the claimed jet-fuel blend composition comprising 30-99 vol% hydrotreated blend component, 1-70 vol% mineral jet fraction, a blend component containing at least 50 wt.% combined isoolefins and isoparaffins, no greater than 5 wt.% C19+ hydrocarbons, and the claimed distillation and freeze-point properties.
Deimund teaches an integrated oxygenate-to-distillate process in which an oxygenate-derived light olefin stream is subjected to a first oligomerization reactor, the reactor effluent is passed to a separation column to remove light components, and the purified olefin stream is forwarded to a downstream oligomerization reactor (Deimund Fig. 2; ¶¶ [0013], [0020], [0039]-[0041]). Deimund further teaches recycling C2-C4 olefins to the oligomerization process and removing carbon monoxide, carbon dioxide, water, and other light impurities prior to downstream oligomerization (Deimund ¶¶ [0039]-[0041]). Thus, Deimund teaches a first oligomerization unit including a reactor followed by a lights-removal separation column, purification of the intermediate olefin stream, and recycle of light olefins.
Peters teaches making a renewable jet fuel blendstock by oligomerizing olefins and hydrogenating/hydrotreating the oligomerization product to produce saturated isoparaffinic jet fuel blendstock (Peters ¶¶ [0070]-[0072], [0118]-[0121]). Peters further teaches that hydroprocessed SPK requirements include a T10 distillation temperature of no greater than 205°C, a final boiling point of no greater than 300°C, and a freezing point of no greater than ------40°C (Peters ¶ [0071], Table 1). Peters also teaches removing C20 and higher hydrocarbons, when present, to meet the final boiling point specification, and that fractionation may be performed before or after hydrogenation/hydrotreating (Peters ¶ [0121]). Peters further teaches that the hydrotreated jet blendstock can comprise primarily C12 and C16 isoparaffins, and that C3-C6 olefins may be oligomerized to a C10-C16 olefin mixture which, upon hydrogenation/hydrotreating, meets or exceeds D7566 specifications (Peters ¶¶ [0123]-[0125]). Thus, Peters teaches the claimed hydrotreated jet-fuel blend component and the claimed blended jet boiling-range composition.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify the first oligomerization unit of Lilga by incorporating the reactor/separation arrangement taught by Deimund because Deimund teaches that intermediate removal of light components before downstream oligomerization improves olefin conversion, facilitates recycle, and increases production of fuel-range hydrocarbons (Deimund ¶¶ [0039]-[0041]). It would have been further obvious to modify the hydrotreated product of Lilga by blending and fractionating the hydrotreated oligomerization product in accordance with Peters because Peters teaches that hydrotreated oligomerization products are suitable synthetic jet-fuel blendstocks and that blending with mineral jet fuel while controlling boiling-range properties produces aviation fuels meeting ASTM specifications.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify the process of Lilga by fractionating and blending the hydrotreated oligomerization product in view of Peters so that the blend component contains predominantly isoolefin/isoparaffin-derived hydrocarbons, contains 5.0 wt.% or less C19+ hydrocarbons, and is blended with a mineral jet boiling range fraction to meet the claimed T10, final boiling point, and freeze point because Peters teaches that oligomerized-and-hydrotreated olefin products are useful SPK jet blendstocks, that C20+ hydrocarbons should be removed to meet final boiling point requirements, and that the ratio of synthetic isoparaffinic blendstock to conventional/mineral jet fuel is selected to meet ASTM jet fuel specifications (Peters ¶¶ [0071]).
Regarding claim 2, Lilga teaches hydroprocessing the oligomerization products to produce paraffinic jet-range hydrocarbons suitable for aviation fuels (Lilga ¶¶ [0140]-[0144]).
Peters teaches hydrogenating oligomerized olefins to produce hydrotreated synthetic jet-fuel blendstocks having a predominantly isoparaffinic composition suitable for blending into conventional jet fuel (Peters ¶¶ [0118]-[0125]). Thus, Peters teaches a hydrotreated blend component containing a substantial amount of isoparaffinic hydrocarbons. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify the hydroprocessing operation of Lilga in view of Peters to produce a hydrotreated stream containing at least 60 wt. % combined isoolefins and isoparaffins because Peters teaches controlling the hydrogenation product composition to achieve aviation-fuel properties. The claimed composition merely reflects optimization of the hydroprocessing severity and resulting hydrocarbon distribution. Regarding claims 3 and 16, Lilga teaches hydroprocessing oligomerization products to produce paraffinic jet-range hydrocarbons (Lilga ¶¶ [0140]-[0144]). Peters teaches maximizing the isoparaffinic content of hydrotreated synthetic jet-fuel blendstocks for aviation fuel applications (Peters ¶¶ [0118]-[0125]). It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify the hydroprocessing operation of Lilga in view of Peters so that the hydrotreated stream or blend component contains at least 70 wt.% combined isoolefins and isoparaffins because Peters teaches producing highly isoparaffinic jet-fuel blendstocks to satisfy aviation-fuel performance requirements. The particular percentage represents routine optimization of the hydrogenation process.
Regarding claims 5 and 17, Lilga does not expressly teach that the C4+ olefin stream contains no greater than 5 wt.% methane, ethylene, and ethane combined. Deimund teaches passing the effluent from the first oligomerization reactor through a separation column to remove lighter components before downstream oligomerization (Deimund Fig. 2; ¶¶ [0020], [0039]). Thus, Deimund teaches separating methane, ethylene, ethane, and other light components from the heavier olefin stream. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify the first oligomerization and separation process of Lilga by incorporating the separation operation taught by Deimund and operating the separation unit so that the C4+ olefin stream contains no greater than 5 wt.% methane, ethylene, and ethane combined because Deimund teaches removal of light hydrocarbons prior to downstream oligomerization, and the concentration of residual light hydrocarbons remaining in the heavier olefin stream depends upon routine optimization of the operating conditions of the separation unit. Claim 6 is rejected for the same reasons set forth with respect to claim 5. It would have been obvious to modify the separation process of Lilga in view of Deimund so that the concentration of methane, ethylene, and ethane remaining in the C4+ olefin stream is no greater than the claimed amount because the degree of removal of light hydrocarbons is controlled by routine optimization of the operating conditions of the separation process.
Regarding claims 8 and 19, Lilga does not expressly disclose combining the C4+ olefin stream with a propylene/C4+ olefin stream before the second oligomerization stage. Deimund teaches recovering light olefin streams from the oxygenate conversion section, separating the streams, and supplying the recovered olefins to a downstream oligomerization reactor (Deimund Fig. 2; ¶¶ [0020], [0039]-[0041]). Thus, Deimund teaches combining recovered olefin streams before downstream oligomerization. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify the second oligomerization stage of Lilga by combining the C4+ olefin stream with the recovered propylene/C4+ olefin stream before the second oligomerization stage as taught by Deimund because Deimund teaches combining recovered olefin streams for downstream oligomerization to improve overall conversion and increase production of fuel-range hydrocarbons. Regarding claim 10, Lilga does not expressly disclose recycling unconverted C4+ olefins through the second oligomerization stage. Deimund teaches recycling C2-C4 olefins from the separation section back to the oligomerization process to increase conversion of light olefins into higher molecular weight hydrocarbons (Deimund ¶ [0041]; Fig. 2). Thus, Deimund teaches recycle of unconverted olefins to the oligomerization section. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify the recycle process of Lilga by recycling a portion of the unconverted C4+ olefin stream through the second oligomerization stage in accordance with the recycle scheme taught by Deimund because Deimund teaches that recycling unconverted light olefins improves olefin conversion, increases production of fuel-range hydrocarbons, and improves overall process efficiency. Claims 7, 11-14 and 18 are rejected under 35 U.S.C. 103 as being unpatentable over references as applied to claims 1 and 15 above, and further in view of Kuzma (US 2016/0362352 A1). The processes of Lilga, Deimund and Peters are as discussed above.
Regarding claims 7 and 18, Lilga does not expressly teach that the ethylene stream contains at least 2000 wppm ethane and no greater than 5 wppm each of carbon monoxide and hydrogen.
Kuzma teaches recovering an ethylene stream from a methanol-to-olefins process by removing hydrogen, carbon monoxide, methane, and other light components from the MTO reactor effluent through an absorber-demethanizer and downstream separation system while recovering an ethylene/ethane stream for downstream processing (Kuzma ¶¶ [0009]-[0013], [0038]-[0040]).
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify the process of Lilga by employing the MTO recovery and purification process of Kuzma, together with the olefin purification techniques of Cantrell, so that the recovered ethylene stream contains only trace amounts of carbon monoxide and hydrogen while retaining a desired amount of ethane. Kuzma teaches removing hydrogen and carbon monoxide from the ethylene product stream while recovering ethylene together with ethane for downstream processing, and Duimund teaches further purification of olefin streams before oligomerization. Therefore, selecting purification operating conditions that produce an ethylene stream containing no greater than 5 wppm carbon monoxide and hydrogen while retaining at least 2000 wppm ethane would have constituted routine optimization of the purification process, which is a result-effective variable.
Neither Lilga nor Deimund expressly teaches the specific methanol-to-olefins recovery process recited in claims 11-14.
Regarding claim 11, it would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify the oxygenate-derived ethylene feed preparation process of Lilga, as implemented through the integrated oxygenate conversion process of Deimund, by employing the MTO recovery process taught by Kuzma because Kuzma teaches an efficient industrial process for recovering and purifying an ethylene-rich stream from an MTO reactor effluent while removing hydrogen, carbon monoxide, methane, and heavier hydrocarbons prior to downstream olefin conversion. Employing Kuzma's recovery process would have predictably provided a purified ethylene feed suitable for the oligomerization process of Lilga.
Claim 12 further recites that the ethylene stream contains at least 90% of the ethane present in the raw olefin stream.
Kuzma teaches recovering an ethylene/ethane fraction from the MTO separation train while separating methane overhead and heavier hydrocarbons in downstream fractionation units (Kuzma ¶¶ [0038]-[0040]). Thus, Kuzma teaches recovering ethane together with the ethylene product stream.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify the ethylene recovery process incorporated into Lilga by operating the ethylene/ethane separation of Kuzma so that substantially all of the ethane remains with the recovered ethylene stream because the degree of ethylene/ethane separation depends upon routine optimization of the operating conditions of the separation process, including reflux ratio, pressure, and separation efficiency.
Claim 13 recites that the methanol is converted to olefins using a silicoaluminophosphate catalyst, an aluminosilicate catalyst, or steam cracking.
Deimund teaches converting oxygenates to light olefins using oxygenate conversion catalysts including zeotype catalysts having 8-member or 10-member ring framework structures, including SAPO-34, CHA, AEI, EMM-2, ZSM-48, and other aluminosilicate or silicoaluminophosphate catalysts (Deimund ¶¶ [0019]-[0035]). Thus, Deimund teaches methanol-to-olefins conversion utilizing both silicoaluminophosphate and aluminosilicate catalysts.
Accordingly, the selection of a silicoaluminophosphate catalyst or an aluminosilicate catalyst for producing the raw olefin stream would have been obvious because Deimund expressly identifies such catalysts as suitable oxygenate-conversion catalysts for producing the olefin feed employed in the integrated oligomerization process.
Claim 14 recites that separating the raw olefin stream further comprises producing at least a portion of the propylene/C4+ stream.
Kuzma teaches separating the MTO reactor effluent into individual hydrocarbon fractions, including ethylene, propylene, and heavier C4+ hydrocarbons, through the absorber-demethanizer and downstream fractionation system (Kuzma ¶¶ [0038]-[0040]). Thus, Kuzma teaches producing a propylene/C4+ stream from the raw olefin stream.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify the feed preparation process incorporated into Lilga by recovering a propylene/C4+ stream from the MTO separation train as taught by Kuzma because Kuzma teaches that separation of the raw olefin stream into individual olefin fractions provides suitable feed streams for downstream hydrocarbon conversion processes, including oligomerization.
Claim 9 is rejected under 35 U.S.C. 103 as being unpatentable over references as applied to claim 1 above, and further in view of Anina et al. (EP 2684857 A1).
The process of Liga is as discussed above.
Lilga does not teach that the first oligomerization unit utilizes a homogeneous catalyst.
Anina teaches a method for oligomerization of ethylene by feeding ethylene, solvent, and a catalyst composition comprising a catalyst and cocatalyst into a reactor to produce C4+ linear α-olefins (Abstract; ¶¶ [0001], [0007]-[0010], [0014]-[0018]). Anina further expressly teaches that the process employs a homogeneous catalyzed ethylene oligomerization technology, wherein the homogeneous catalyst system is introduced with the solvent into the oligomerization reactor (EP '857 ¶¶ [0007]-[0010]).
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the process of Lilga by utilizing the homogeneous ethylene oligomerization catalyst system taught by Anina in the first oligomerization stage of Lilga because homogeneous transition-metal catalyst systems were well known for selectively converting ethylene into C4+ α-olefins while Cantrell teaches subsequent oligomerization of intermediate olefins using heterogeneous catalysts. Such a modification merely substitutes one known ethylene oligomerization catalyst system for another to obtain the predictable production of C4+ olefins.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to TAM M NGUYEN whose telephone number is (571)272-1452. The examiner can normally be reached Mon - Frid.
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/TAM M NGUYEN/Primary Examiner, Art Unit 1771
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