CTNF 18/249,021 CTNF 90074 DETAILED ACTION Notice of Pre-AIA or AIA Status 07-03-aia AIA 15-10-aia The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Status of the Claims A preliminary amendment filed on 04/13/2023 has been entered. Claims 6, 8, 10-13, 15-17 and 20 have been amended. Thus claims 1-20 are currently pending and are under examination. Claim Objections 12-151-08 AIA 07-43 12-51-08 Claim s 3-7, 13-14, 17 and 20 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. Claim 18 is objected to because of the following informalities: replace the colon “:” at the end of line 2 with a semicolon “;”. Claim Rejections - 35 USC § 112 07-30-02 AIA 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. 07-34-01 Claims 8-12 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. Regarding claim 8-12, the limitation “reaction and separation, in the reactive distillation column , the effluent of the first reactor unit into a first stream comprising primarily unreacted water and unreacted ethylene oxide, collectively, and a second stream comprising primarily unreacted water, and mono ethylene glycol, unreacted ethylene oxide, collectively; flowing the second stream into the second reactor unit ” renders the claim vague and indefinite. Based on claim 1, the reactive distillation is the second reactor that produces additional alkylene glycol by subjecting the unreacted alkylene oxide and unreacted water from the first reactor to the reactive distillation. However, according to the limitation of claim 8, it appears that the reactive distillation has a different function than that of claim 1 because: It is used in separating the effluent of the first reactor into a first stream and second stream, and The second stream from the reactive distillation flows to the second reactor unit, which makes the reactive distillation a distinct unit from the second reactor. Thus, it is unclear how a reactive distillation that is used as a second reactor unit in claim 1 can also separate effluents from the first reactor and can be a separate unit from the second reactor. Claims 9-12 are also rendered indefinite for their dependency on claim 8. Note: The specification describes a different setting when the process comprises separation of the effluent of the first reactor unit. As shown in Fig. 2, the first reactor 201 produces an effluent 202 that is separated to first stream 204 and second stream 205 using separation unit 203 , and flowing second stream 205 to a second reactor 206 ([0038]-[0040]). The separation unit 203 is described as including a distillation unit, flash vessel, or combinations thereof ([0038]). In this setting, neither the separation unit 203 nor the second reactor 206 is described as being a reactive distillation . Whereas, Fig. 1, which is according to claim 1, uses a first reactor 101 and a reactive distillation unit 103 (a second reactor). However, the reactive distillation unit 103 does not appear to be used in separating the effluent 102 of the first reactor 101 as recited in claim 8. Hence, Applicant is advised to amend claim 8 in view of the embodiments described in the specification. For purpose of applying art, the limitation “reactive distillation” in line 2 will not be given patentable weight. Claim Rejections - 35 USC § 103 07-06 AIA 15-10-15 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. 07-20-aia AIA 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. 07-23-aia AIA 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. 07-20-02-aia AIA 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. 07-21-aia AIA Claim s 1-2, 8-10, 12, 15-16 and 18-19 are rejected under 35 U.S.C. 103 as being unpatentable over International publication WO1998/014419A1 (WO’419; equivalent to Patent number EP0929503B1 cited in IDS 04/27/2023 ) . Regarding claims 1-2 and 13, WO’419 teaches (pages 3-6 and Fig. 2) a method of producing alkylene glycol, the method comprising: flowing a feed stream comprising alkylene oxide via line 2 and water via line 1 into a first reactor unit 5 ; subjecting the alkylene oxide and water, in the first reactor unit, to first reaction conditions such that an effluent of the first reactor unit comprises an alkylene glycol (bottoms stream 7 ), unreacted alkylene oxide (pg. 4, ln. 16), and unreacted water (distillate stream 3 and bottoms stream 7 ); flowing alkylene oxide vial line 2 and unreacted water via lines 3 and 7 to a second reactor unit 5 ; and subjecting the unreacted alkylene oxide and unreacted water in the second reactor unit to second reaction conditions sufficient to produce additional alkylene glycol; wherein the second reactor unit is an evaporation column reactor, which is equivalent to reactive distillation column because it integrates a chemical reaction in the reaction in the catalyst bed 13 of the reaction unit and separation in separation units 4 and 6 that results into distillate 3 and fractionation and distillation of epoxide (pg. 4; ln. 14) and an enhanced yield of mono alkylene to di alkylene glycol ratio is produced at a ratio of water to alkylene oxide of lower limit 1.05:1 (pg. 3, lines 7-20). Regarding claims 8 and 13, the second reactor of WO’419 comprises reaction and separation of the effluent of the first reactor unit into a first stream comprising primarily unreacted water and unreacted ethylene oxide (prior to the enriching section 4 , comprising water and unreacted epoxide, pg. 4, ln. 15-18) and a second stream that comprises glycol, water and unreacted epoxide (before the reboiler 8 ) (pg. 4, ln.10-14), flowing the second stream into the second reactor unit. Regarding claims 1 and 18, while WO’419 teaches subjecting alkylene oxide to the second reactor via lines 2 in view of Fig. 2, the reference fails to teach that the alkylene oxide is at least a portion of the unreacted alkylene oxide. However, the reference teaches that after the reaction in the first reactor, a step of stripping unreacted epoxide (alkylene oxide) (claim 3) is conducted in the stripping zone 6 (Fig. 2) by providing for fractionation and distillation of the epoxide out of the liquid phase (pg. 4, lines 10-14). Thus, one of ordinary skilled in the art would have been motivated to use the unreacted epoxide (alkylene oxide) that is separated out from the first reactor as a feed to the second reactor via lines 2 . Regarding claims 9 and 15, the process of WO’419 produces di- and tri- glycols (pg. 2, ln. 4-6). Regarding claims 10 and 16, the use of catalysts in the reaction units 5 are optional (pg. 5, ln. 37-38 to pg. 6, ln. 2; the first column's Reaction Zone 5 might have no catalytic material present in the Reaction Zone 5 , but the second column might have a catalyst bed ). Regarding claim 12, the reference teaches recovering at least a portion of ethylene oxide from the first stream for pure ethylene oxide production (pg. 4, ln. 12-14, and claim 3). Regarding claim 19, WO’419 teaches recycling the first stream 3 via line 9 to the first reaction unit 5 . It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct method of producing alkylene glycol, the method comprising: flowing a feed stream comprising alkylene oxide and water into a first reactor unit; subjecting the alkylene oxide and water, in the first reactor unit, to first reaction conditions such that an effluent of the first reactor unit comprises an alkylene glycol, unreacted alkylene oxide, and unreacted water; flowing at least a portion of the unreacted alkylene oxide and unreacted water to a second reactor unit; and subjecting the unreacted alkylene oxide and unreacted water in the second reactor unit to second reaction conditions sufficient to produce additional alkylene glycol; wherein the second reactor unit is a reactive distillation column and higher mono alkylene to di alkylene glycol ratio is produced even at lower water to alkylene oxide ratio; or flowing ethylene oxide and water into a first reactor; subjecting the ethylene oxide and water in the first reactor to reaction conditions sufficient to produce ethylene glycol such that a first effluent stream of the first reactor comprises mono ethylene glycol, unreacted ethylene oxide, and unreacted water; separating, in a separation unit, the first effluent stream into a first stream comprising primarily unreacted water and unreacted ethylene oxide, collectively and a second stream comprising primarily unreacted ethylene oxide, unreacted water, and mono ethylene glycol, collectively; flowing the second stream into a second reactor; and subjecting the second stream in the second reactor to reaction conditions sufficient to produce additional mono ethylene glycol; wherein the second reactor unit is a reactive distillation unit; in view of the teachings of WO’419 . Allowable Subject Matter The subject matter of claims 3-7, 11, 13-14, 17 and 20 are free of prior art references. The teachings of the closest prior art reference International publication WO1998/014419A1 (WO’419; equivalent to Patent number EP0929503B1 cited in IDS 04/27/2023 ) have been set forth above. Regarding claims 3-7, WO’419 further teaches that the first reactor is evaporation column reactor, but fails to teach that the first reactor is a plug flow reactor. Moreover, Patent number US6,160,187A (US’187) teaches a method for making glycol in an adiabatic reactor system including feeding water and an epoxide, wherein the adiabatic reactor is operated in plug flow manner. However, the reference fails to teach or suggest that the adiabatic reactor can be used in combination with a second reactor as instantly claimed, wherein the second reactor is a reactive distillation. As such, a skilled artisan would not have been motivated in replacing the evaporation column reactor (first reactor) of WO’419 with the plug flow operated adiabatic reactor of US’187 to arrive at the instantly claimed invention. Regarding claims 11, 13-14, 17 and 20, nowhere in WO’419 teaches or suggests that: the second reaction conditions in the second reactor unit comprise a reactor inlet temperature in a range of 160 to 220° C. and a reaction pressure of 10 to 20 bar; the first reactor has a reaction residence time of 0.5 to 8 minutes; the reaction conditions in the first reactor unit comprise: a reactor inlet temperature in a range of 120 to 160° C., a reaction pressure of 18 to 25 bar, and a residence time of 0.5 to 8.0 minutes; and the separating of first effluent stream to produce first stream and second stream is performed at an overhead boiling temperature range of 150 to 180° C. and a pressure range of 6 to 20 bar. Conclusion 12-151-07 AIA 07-97 12-51-07 Claim s 1-2,8-10,12,15-16 and 18-19 are rejected and no claims are allowed. Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm. 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, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. 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If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692 Application/Control Number: 18/249,021 Page 2 Art Unit: 1692 Application/Control Number: 18/249,021 Page 3 Art Unit: 1692 Application/Control Number: 18/249,021 Page 4 Art Unit: 1692 Application/Control Number: 18/249,021 Page 5 Art Unit: 1692 Application/Control Number: 18/249,021 Page 6 Art Unit: 1692 Application/Control Number: 18/249,021 Page 7 Art Unit: 1692 Application/Control Number: 18/249,021 Page 8 Art Unit: 1692 Application/Control Number: 18/249,021 Page 9 Art Unit: 1692 Application/Control Number: 18/249,021 Page 10 Art Unit: 1692 Application/Control Number: 18/249,021 Page 11 Art Unit: 1692