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 18/638522 application originally filed April 17, 2024.
Amended claims 1 and 3-21, filed June 08, 2026, are pending and have been fully considered. Claim 2 has been canceled. Claims 15-19 are withdrawn from consideration due to being drawn to a nonelected invention.
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) 1, 3, 4, 9 and 20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Senetar (US 2007/0203382) in view of Senetar et al. (WO 2008/039552 A1) hereinafter “Senetar ‘552”.
Regarding Claims 1, 3, 4, 9 and 20
Senetar discloses in paragraph 0001, conversion of oxygenates to olefins and, more particularly, to light olefins with enhanced carbonyl and, in particular, acetaldehyde, removal or recovery.
Senetar discloses in paragraph 0021, an oxygenate-containing feedstock can be converted to olefins and, more particularly, to light olefins via a catalytic reaction. The light olefins produced or resulting from such conversion can be recovered from the oxygenate conversion reactor effluent via a recovery system employing water.
Senetar discloses in paragraph 0023, particularly, an oxygenate-containing feedstock or feedstream 12 such as generally composed of light oxygenates such as one or more of methanol, ethanol, dimethyl ether, diethyl ether, or mixtures thereof, is introduced into an oxygenate conversion zone or reactor section 14 wherein the oxygenate-containing feedstock contacts with an oxygenate conversion catalyst at reaction conditions effective to convert the oxygenate-containing feedstock to form an oxygenate conversion effluent stream comprising fuel hydrocarbons (i.e. petroleum hydrocarbons), light olefins, and C4+ hydrocarbons, in a manner as is known in the art, such as, for example, utilizing a fluidized bed reactor.
Senetar discloses in paragraph 0028, the oxygenate conversion reactor section 14 produces or results in an oxygenate conversion product or effluent stream 16 such as generally comprising hydrocarbon product materials such as fuel gas hydrocarbons, light olefins, and C4+ hydrocarbons; by-product water; and remaining oxygenates such as methanol, dimethyl ether (DME) and other trace oxygenates including carbonyls such as acetaldehyde.
Senetar discloses in paragraph 0029, the compressed oxygenate conversion effluent stream 22 or at least a portion thereof, is introduced into an oxygenate absorber zone 26, such as in the form of at least one absorber column. In the oxygenate absorber zone 26, oxygenates such as methanol, dimethyl ether (DME) and other trace oxygenates including carbonyls such as acetaldehyde are absorbed in circulated water, such as provided by the streams 30 and 32, described in greater detail below, and thus are separated from the hydrocarbon product materials.
Senetar discloses in paragraph 0030, thus, the absorber zone 26 forms or results in an oxygenate-rich water stream 36 such as comprises such oxygenate materials in water and a stream 40 such as comprises such hydrocarbon product materials. The hydrocarbon product material stream 40, if desired and as described above, can be further processed such as by being conventionally washed with a caustic solution to neutralize any acid gases and dried prior to passage on to a desired gas concentration and product recovery system.
Senetar discloses in paragraph 0031, the oxygenate-rich water stream 36 is passed to an oxygenate stripper zone 44, such as in the form of at least one stripper column and such as includes a selected number stages such as in the form of trays or packing. In the oxygenate stripper zone 44, at least a portion of oxygenate species such as dimethyl ether and methanol, for example, can be stripped or otherwise effectively removed from the water such as to form an oxygenate-containing overhead stream 50, such as can be ultimately returned to the oxygenate conversion zone or reactor section 14 for further reaction processing, and a recycle water stream 52.
Senetar discloses in paragraph 0034, the water of recycle water stream 52 may subsequently be appropriately utilized in the associated process scheme as may be desired. For example, as shown for the process scheme 10 in FIG. 1, a portion of the recycle water stream, designated by the reference numeral 30, is returned to the oxygenate absorber zone 26 for contact with the compressed oxygenate conversion effluent stream 22, such as described above.
Senetar discloses in paragraph 0035, another portion of the recycle water stream, designated by the reference numeral 56, is passed to a wash water stripper 60. In the wash water stripper 60, methanol and remaining oxygenates are effectively removed so as to produce an overhead stream 64 containing the recovered oxygenates and such as can be returned to the oxygenate stripper zone 44. The wash water stripper 60 also produces a bottoms water stream 68 containing insignificant amounts of dissolved oxygenates. A portion of the bottoms stream, designated by the reference numeral 70 and such as containing undesirable materials, can be returned to the effluent treatment zone 20 in which it is further processed for use in the treatment zone 20 and portions of which are removed from the process in water streams 80 and 90, such as in a manner known in the art. Another portion of the bottoms water stream, i.e., the above-referred to circulated water stream 32, can desirably be introduced into the oxygenate absorber zone 26, as described above, for the purpose of recovering additional oxygenates beyond the limitations imposed by the oxygenate content of the stream 30. An additional portion of the bottoms water stream 68, designated by the reference numeral 86, may be utilized to wash and recover methanol and other oxygenates from the liquid products formed in the zone 20, and ultimately recycled back to the zone 44 via the stream 24.
Senetar discloses oxygenate conversion through an absorber. Senetar further discloses providing a oxygenate stream comprising fuel gas hydrocarbons, light olefins, C4+ hydrocarbons and remaining oxygenate materials to an absorber but fails to teach the oxygenate stream to undergo fluid cracking.
However, it is known in the art to apply cracking to oxygenates in order to generate C3 and/or C4 hydrocarbon oxygenates, as taught by Senetar ‘552.
Senetar ‘552 discloses in paragraph 0025, oxygenate conversion processing to produce olefins can advantageously be integrated with olefin cracking processing to result in increased relative amounts of light olefin products through either or both reducing the water content and/or reducing the oxygenate content of the feed to the olefin cracking zone. Such processing may be embodied in a variety of processing arrangements. As representative, FIG. 1 illustrates a simplified schematic process flow diagram for a process scheme, generally designated by the reference numeral 310, for the conversion of oxygenates to olefins and integrated with product olefin cracking for increased light olefin production in accordance with one preferred embodiment.
Senetar ‘552 discloses in paragraph 0026, in the process scheme 310, an oxygenate-containing feedstock or feedstream 312 such as generally composed of light oxygenates such as one or more of methanol, ethanol, dimethyl ether, diethyl ether, or mixtures thereof, is introduced into an oxygenate conversion zone or reactor section 314 wherein the oxygenate-containing feedstock contacts with an oxygenate conversion catalyst at reaction conditions effective to convert the oxygenate-containing feedstock and to form an oxygenate conversion effluent stream comprising fuel gas hydrocarbons, light olefins, and C4+ hydrocarbons, in a manner as is known in the art, such as, for example, utilizing a fluidized bed reactor.
Senetar ‘552 discloses in paragraph 0044, at least a portion of the dried treated C4+ hydrocarbon fraction stream 372 is subsequently appropriately introduced into an olefin cracking reactor section 386 wherein the at least a portion of the process stream 372 contacts with an olefin cracking catalyst and at reaction conditions, in a manner as is known in the art, effective to convert C4 and C5 olefins therein contained to a cracked olefins effluent stream 388 comprising light olefins.
Senetar ‘552 discloses in paragraph 0058, between such a mixed C4+ hydrocarbon stream 458 and such a washed stream 466, the vast bulk of the oxygenates will typically be present in the washed stream 466, this embodiment introduces such hydrocarbon-containing stream into a treatment zone 476, introduced into the treatment zone 476 as shown by the line 482 from a sulfite-containing reservoir 484 added to in order to form the treated C4+ hydrocarbon fraction stream 477 containing oxygenates in an appropriately reduced or minimized relative amount.
Therefore, it would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to place the oxygenates of Senetar under the cracking of Senetar ‘552 in order to convert C3 and/or C4 hydrocarbons and increase the amount of light olefins.
Claim(s) 5-8, 10-14 and 21 is/are rejected under 35 U.S.C. 103 as being unpatentable over Senetar (US 2007/0203382) in view of Senetar et al. (WO 2008/039552 A1) hereinafter “Senetar ‘552” and further in view of de Menezes et al. (US 2022/0041529).
Regarding Claims 5-8, 10-14 and 21
Senetar modified by Senetar ‘552 discloses the process for removing oxygenates from a fuel hydrocarbons of independent claims 1 and 20 of the present invention but fails to further teach and/or suggest the process steps of claims 5-8, 10-14 and 21.
However, it is known in the art to apply further methods of removing oxygenates from hydrocarbons, as taught by de Menezes.
de Menezes discloses in paragraph 0021, proper treatment of hydrocarbon containing liquid and gaseous streams in the propane and/or butane dehydrogenation complex. In some cases, the propane and/or butane dehydrogenation complex include propylene and/or iso-butylene derivative process units. Various effluent streams from different parts of the propane/butane dehydrogenation complex are combined in appropriate collection vessels, including an off-gas knockout drum, a hydrocarbon buffer vessel, a fuel gas knockout drum, a spent caustic buffer vessel, and a waste water buffer vessel. Streams from these vessels are sent to a thermal oxidation system. This allows the elimination of a number of components from the conventional process, including one or more of the spent sulfidic caustic treatment section, regeneration vent gas treatment section, butane isomerization off gas scrubber, CN destruction system and dedicated thermal oxidizing system, as well as the associated piping, instrumentation, controls, and mechanical and structural components, reducing both capital costs and operating costs. In addition, the process reduces the cost of treatment chemicals, and the size of certain streams may also be reduced.
de Menezes discloses in paragraph 0024, thermally oxidizing at least one of the spent caustic stream, the liquid hydrocarbon stream, the off-gas stream, and the fuel gas stream comprises: thermally oxidizing the at least one of the spent caustic stream, the liquid hydrocarbon stream, the off-gas stream, and the fuel gas stream in a thermal oxidizing section to form a flue gas consisting essentially of at least one of H2O, Na2CO3, Na2SO3, Na2SO4, CO2, N2, O2, SOx, NOx, NaCl, HCl, Cl2, dioxins, and furans; optionally recovering waste heat from the flue gas in a waste heat recovery section; removing at least one of SOx, HCl, and Cl2 from the flue gas in a SOx removal section to form a de-SOx outlet flue gas consisting essentially of at least one of H2O, CO2, N2, O2, NOx, dioxins, and furans.
de Menezes further discloses in paragraph 0129, the inlet temperature of the thermal oxidizing section 1600 is typically in the range of −30-500° C with a pressure of −1 kPa(g) to 3000 kPa(g). The outlet temperature is typically in the range of 650-1300° C with a pressure of −1 kPa(g) to 50 kPa(g). The hydrocarbons are converted to H2O and CO2. The sulfides from the sulfur species (e.g. H2S) present in feed are converted to oxidized sulfur particulate SOx including, but not limited to, SO2 and SO3, and H2O. The nitrogen from the nitrogen bound molecules (e.g. NH3, di-ethanol urea (DEU), di-ethanol amine (DEA), and mono-ethanol amine (MEA)) present in the feed are converted to nitrogen (N2) and NOx, including but not limited to NO, NO2. The HCl and Cl2 remain.
de Menezes discloses in paragraph 0058, regeneration net gas stream 220 is sent to the adsorbent bed 195 to regenerate the adsorbent by removing acid gas. The regenerant gas stream 230 from the adsorbent bed 195 is sent to the regenerant gas scrubbing zone 235. A NaOH stream 240 is introduced into the regenerant gas scrubbing zone 235 to remove sulfur from the regenerant gas stream 230 forming a sulfidic spent caustic stream 245 and a scrubbed regenerant gas stream 250.
Therefore, it would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to add the thermal oxidizing system of de Menezes to the removing oxygenates from hydrocarbons of Senetar. The motivation to do so is to add a thermal oxidizing system to aid in the removal of oxygenates, nitriles and various gas streams.
Response to Arguments
Applicant’s arguments directed to the newly submitted claimed amendments, filed June 08, 2026, with respect to the rejection(s) of claim(s) 1, 3-14, 20 and 21 under Senetar (US 2007/0203382) 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 Senetar (US 2007/0203382) in view of Senetar et al. (WO 2008/039552 A1) hereinafter “Senetar ‘552”.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Banerjee et al. (US 2018/0119029) discloses in the abstract, a process is presented for the removal of contaminants like oxygenates from hydrocarbons. The contaminant oxygenates are removed from hydrocarbons that may be feed to cracking units. A crude feed stream is fed to a water wash column along with water to remove oxygenates and is subsequently treated with an adsorbent to effectively remove all the oxygenates from the crude hydrocarbon. A regenerant medium from a naphtha hydrotreating unit is used to regenerate the adsorbent.
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.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
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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