Prosecution Insights
Last updated: April 19, 2026
Application No. 18/489,132

PROCESS TO EXTRACT AND DETERMINE NITROGEN COMPOUNDS AND ACIDS PRESENT IN PETROLEUM, DERIVATIVES AND PROCESSING WATERS BEFORE THE REFINING STEP

Non-Final OA §103§112
Filed
Oct 18, 2023
Examiner
FRITCHMAN, REBECCA M
Art Unit
1758
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Serviço Nacional De Aprendizagem Industrial Senai
OA Round
1 (Non-Final)
46%
Grant Probability
Moderate
1-2
OA Rounds
4y 6m
To Grant
82%
With Interview

Examiner Intelligence

Grants 46% of resolved cases
46%
Career Allow Rate
294 granted / 642 resolved
-19.2% vs TC avg
Strong +36% interview lift
Without
With
+35.9%
Interview Lift
resolved cases with interview
Typical timeline
4y 6m
Avg Prosecution
94 currently pending
Career history
736
Total Applications
across all art units

Statute-Specific Performance

§101
10.9%
-29.1% vs TC avg
§103
50.4%
+10.4% vs TC avg
§102
8.4%
-31.6% vs TC avg
§112
23.7%
-16.3% vs TC avg
Black line = Tech Center average estimate • Based on career data from 642 resolved cases

Office Action

§103 §112
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 is the Non-Final Action for application 18/ 489132 filed 10/18/2023 . This application has been examined as part of the Pendency Balance program. Claims 1-12 are pending and have been fully considered. Claim Rejections - 35 USC § 112 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 appl icant regards as his invention. Claims 1-12 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. With respect to Claim 1, the preamble is drawn towards determining nitrogen and acids present in petroleum, derivatives and processing waters and includes steps a-d, however none of steps a-d refer to “petroleum, derivatives and processing waters,” so therefore as preambles are not always limiting in the claim and nothing in steps a-d refer back, it is unclear if the instant method really requires one of the fluids referred to in the preamble or not. Further- it is noted that any method that teaches any extraction, separation, preconcentration, and or analysis would read of the broad claim currently due to this. Further for Claim 1, in the “petroleum, derivatives and processing waters,” it is not clear what the “derivatives,” are of, or what the processing waters are of. Can these be any and every derivative or processing waters for things like water a coffee maker? With respect to Claim 2, “the thermal degradation products,” fail to have proper antecedent basis as “thermal degradation products,” were not mentioned prior to this in the claim. With respect to Claim 3, it is unclear if the thing in brackets, “(oil/water),” is required or not. Correction is required. With respect to Claim 4, “the pH,” and “the medium,” fail to have proper antecedent basis as they were not mentioned prior to this in the claim s so it is unclear what applicant is referring back to. With respect to Claim 7, “the oily fraction ,” and “the aqueous fraction ,” in lines 1 & 2 of the claim fail to have proper antecedent basis as they were not mentioned prior to this in the claims so it is unclear what applicant is referring back to. With respect to Claim 8, “the aqueous fraction,” fails to have proper antecedent basis as they were not mentioned prior to this in the claims so it is unclear what applicant is referring back to. With respect to Claim 10, it says, “can pass,” and in Claim 8, it is required that it passes through 3 preconditioned solid phases. This seems to be broadening the Claim from a claim which it depends from and this is not permitted. Correction is required. Further for Claim 10, “depending on the intended purposes,” is unclear in the claim as different people would read this differently. It is a relative term/phrase, therefore making the scope claimed unclear and confusing. With respect to Claim 11, “ the method depends on the analyte to be analyzed ,” is unclear in the claim as different people would read this differently. It is a relative term/phrase, therefore making the scope claimed unclear and confusing. With respect to Claim 12, the detection techniques claimed were all referred to in Claim 11 which Claim 12 depends on, but applicant did not refer back to these terms using “the,” so it is unclear if they are the same or not. Therefore, the claim is unclear. Claims 5-6, 9 are rejected due to their dependency on an unclear claim. Claim Rejections - 35 USC §103 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 non - obviousness. 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 1 is rejected under 35 U.S.C. 103 as being obvious over WEISS/ BL Technologies in WO 2019/099231 (as cited on IDS dated 02/21/2025) in view o f CHIA in US 20110259798 . With respect to Claim 1, WEISS teaches of method comprising: (a) providing a crude petroleum oil sample; (b) spiking the crude petroleum oil sample with a recovery standard to provide a spiked oil sample; (c) loading the spiked oil sample onto a solid phase extraction (SPE) cartridge; (d) washing the SPE cartridge with an organic solvent to obtain a washed amine sample; and (e) eluting the washed amine sample with an acidified solution to achieve an aqueous elution for analysis (abstract , paragraph 0048 ). WEISS more specifically teaches that the method is for removal/extraction of amines, which are nitrogen containing compounds (paragraph 0003, 0014) which are present in petroleum and crude oils pre-refinery (abstract, paragraph 0008, 0010) . WEISS further teaches that the process includes the steps of extraction (where the sample is loaded onto a SPE cartridge and washed with solvent (steps 104 & 106), and a step of separation (where the analyte is then separated from the extraction medium, step 108) (on Figure 1). WEISS teaches that the SPE cartridge can be pre-conditioned /preconcentration to promote a higher retention/retention concentration of target analytes (paragraph 0038). WEISS then teaches of an analysis step by mass spectrometry or similar analytical methods (paragraph 0030 , 0056). WEISS does not teach of the method extracting acids present in petroleum--- though it is noted that this is only in the preamble of the claim and not the claim body, so is not limiting for the claimed method steps (which neither is the nitrogen). CHIA is used to remedy this and teaches of a method of detecting a reducing the concentration of acids in hydrocarbonaceous mixtures in crude oils (abstract, paragraph 0004-0005). The method uses solid phase extraction to elute out the acids (paragraph 0014). CHIA further teaches that the acids can be quantified/analyzed by ion exclusion chromatography (paragraphs 0017-0018). It would have been obvious to one of ordinary skill in the art before the effective filing date of the instant invention to extract and measure and reduce acidic compounds in petroleum or crude oil compounds as is done in CHIA in the method of WEISS due to the negative effect their corrosivity has on conduits and storage tanks in which the oil or petroleum product is held and the need in the art to reduce these compounds and their affects (CHIA, paragraph 0002, 0005-0006). Claims 2- 6 a re rejected under 35 U.S.C. 103 as being obvious over WEISS/ BL Technologies in WO 2019/099231 (as cited on IDS dated 02/21/2025 ) in view of CHIA in US 20110259798 and further into KOCZO in US 20070299143 . With respect to Claim 2, WEISS and CHIA teach of the above for Claim 1, but does not teach of heating the petroleum. KOCZO is used to remedy this. KOCZO teaches using petroleum or gasoline oils (paragraph 0018), and of separating/extracting components in oil compounds (paragraph 0002, abstract), and specifically of heating to 75 degrees Celsius (paragraph 0063 , 0058 ), which falls in the claimed range of 65 degrees Celsius plus or minus 10 degrees. It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the invention to heat the mixture as is done in KOCZO in the methods of WEISS a nd CHIA due to the advantage that heat has for causing an exotherm/a release/change in energy/separation of products including oil in water separation (KOCZO, paragraph 0099, 0069). With respect to Claim 3, WEISS teaches of the above for Claim 1, but does not teach of heating the petroleum or of constant stirring with the claimed rpm and oil/water ratio. WEISS and CHIA teach of the above for Claim 1, but does not teach of heating the petroleum. KOCZO is used to remedy this. KOCZO teaches using petroleum or gasoline oils (paragraph 0018), and of separating/extracting components in oil compounds (paragraph 0002, abstract), and specifically of heating to 75 degrees Celsius (paragraph 0063 , 0058 ), which falls in the claimed range of 65 degrees Celsius plus or minus 10 degrees. KOCZO further teaches of stirring under a constant 500 rpm (paragraph 0069, 0065) , and of the water oil being 70 % /30% oil to water (paragraph 0131-0132). It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the invention to heat and process the sample/ mixture as is done in KOCZO in the methods of WEISS and CHIA due to the advantage that heat and these processing methods ha ve for causing an exotherm/a release/change in energy/separation of products including oil in water separation (KOCZO, paragraph 0099, 0069). Further—the examiner notes that adjusting the temperature, oil/water concentration and rpm and stirring time, would be obvious to one of ordinary skill through routine experimentation. See MPEP 2144.05 and In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). “ Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." See MPEP 2144.05 and In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). ” With respect to Claim 4, WEISS teaches of the acidified solution being at a pH of 1-6 (paragraph 0043) for extraction of the amine/nitrogenous compounds. This reads on “the pH of the medium is below 5.0 for extraction of nitrogenous compounds or above 11.0 for extraction of acidic compounds,” as claimed through broadest reasonable interpretation. CHIA teaches of the pH needing to be above pH of 9 for acidic com pounds, which also reads on the claimed pH of “above 11,” (paragraph 0016, 0021). With respect to Claim 5, WEISS teaches of the above for Claim 1, but does not teach of centrifuging at 9,500 rpm for 180 min with 2mg of demulsifier per 100 ml. KOCZO is used to remedy this. KOCZO teaches using petroleum or gasoline oils (paragraph 0018), and of separating/extracting components in oil compounds (paragraph 0002, abstract), and further KOCZO further teaches of stirring under a c entrifuging at 4000 rpm and of using demulsifiers while doing this (paragraph 0114-0115 ), and of the water oil being 70 % /30% oil to water (paragraph 0131-0132). It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the invention to process the sample/ mixture as is done in KOCZO in the methods of WEISS and CHIA due to the advantage that heat and these processing methods have for causing an exotherm/a release/change in energy/separation of products including oil in water separation and due to the advantage this would offer for studying phase separation (KOCZO, paragraph 0099, 0069 , 0112-0115 ). Further—the examiner notes that adjusting the concentration of components used and rpm for centrifugation and time, would be obvious to one of ordinary skill through routine experimentation. See MPEP 2144.05 and In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). With respect to Claim 6, WEISS teaches of the above for Claim, but does not teach of the demulsifier . CHIA teaches of adding demulsifiers to the sample to improve separation and using ones which are commercially available (paragraph 0016, 0021, 0021). CHIA and WEISS teaches of the above, but does not teach of the demulsifier being “based on,” ethylene/propylene oxide copolymers. KOCZO teaches of using a demulsifier and specifically of using propylene based demulsifiers (paragraph 0056). It would have been obvious to one of ordinary skill in the art to use the demulsifiers which are used in KOCZO in the methods of WEISS and CHIA since there is a need in the art for demulsifiers capable or breaking emulsions effectively (KOCZO, paragraph 0007). Claim 7 is rejected under 35 U.S.C. 103 as being obvious over WEISS/ BL Technologies in WO 2019/099231 (as cited on IDS dated 02/21/2025 ) in view of CHIA in US 20110259798 and further into KOCZO in US 20070299143 and further in view of LUONG in US 20160299118. With respect to Claim 7, WEISS and CHIA teach of the samples being separated as shown above, but do not teach of collection in a separation funnel. LUONG is used to remedy this and teaches that field sample can have a distinct water an oil phase and that they can be separated by a separation funnel (paragraph 0031). It would have been obvious to one of ordinary skill in the art to separate the phases as is done in LUONG in the methods of WEISS and CHIA due to the advantage this has in providing liquid-liquid extraction (LUONG, paragraph 0031). Claim s 8-10 are rejected under 35 U.S.C. 103 as being obvious over WEISS/ BL Technologies in WO 2019/099231 (as cited on IDS dated 02/21/2025) in view of CHIA in US 20110259798 and further in view of GRAHAM in US 20140296566 . With respect to Claim 8 , WEISS teaches of method comprising: (a) providing a crude petroleum oil sample; (b) spiking the crude petroleum oil sample with a recovery standard to provide a spiked oil sample; (c) loading the spiked oil sample onto a solid phase extraction (SPE) cartridge; (d) washing the SPE cartridge with an organic solvent to obtain a washed amine sample; and (e) eluting the washed amine sample with an acidified solution to achieve an aqueous elution for analysis (abstract, paragraph 0048). WEISS more specifically teaches that the method is for removal/extraction of amines, which are nitrogen containing compounds (paragraph 0003, 0014) which are present in petroleum and crude oils pre-refinery (abstract, paragraph 0008, 0010). WEISS further teaches that the process includes the steps of extraction (where the sample is loaded onto a SPE cartridge and washed with solvent (steps 104 & 106), and a step of separation (where the analyte is then separated from the extraction medium, step 108) (on Figure 1). WEISS teaches that the SPE cartridge can be pre-conditioned/preconcentration to promote a higher retention/retention concentration of target analytes (paragraph 0038). WEISS then teaches of an analysis step by mass spectrometry or similar analytical methods (paragraph 0030, 0056). WEISS does not teach of the method extracting acids present in petroleum--- though it is noted that this is only in the preamble of the claim and not the claim body, so is not limiting for the claimed method steps (which neither is the nitrogen). CHIA is used to remedy this and teaches of a method of detecting a reducing the concentration of acids in hydrocarbonaceous mixtures in crude oils (abstract, paragraph 0004-0005). The method uses solid phase extraction to elute out the acids (paragraph 0014). CHIA further teaches that the acids can be quantified/analyzed by ion exclusion chromatography (paragraphs 0017-0018). It would have been obvious to one of ordinary skill in the art before the effective filing date of the instant invention to extract and measure and reduce acidic compounds in petroleum or crude oil compounds as is done in CHIA in the method of WEISS due to the negative effect their corrosivity has on conduits and storage tanks in which the oil or petroleum product is held and the need in the art to reduce these compounds and their affects (CHIA, paragraph 0002, 0005-0006). WEISS and CHIA teach of the above, and WEIS further teaches that the SPE cartridge can be pre-conditioned to promote a higher retention/retention concentration of target analytes which includes rinsing the SPE cart r idge with 2 cartridge volumes of toluene( paragraph 0038). CHIA also teaches of pre-conditioning (paragraph 0014). WEISS and CHIA do not teach of 3 pre-conditioning cartridges or rinses as instantly claimed. GRAHAM is used to remedy this and teaches of using solid phase extraction to isolate analytes or products of (paragraph 0170). GRAHAM further teaches that the SPE cartridges can be weak anion exchange, cation exchange, C18, or polymer variants thereof (paragraph 0170). GRAHAM further teaches of using 4 cartridges which reads on the instantly claimed 3 (paragraph 0075-0094, 0199, 0028). It would have been obvious to one of ordinary skill in the art to use multiple SPE cartridges as is done in GRAHAM in the methods of WEISS and CHIA due to the advantage that using different and multiple types of SPE offer in giving necessary separation of desired components (GRAHAM, paragraph 0009). With respect to Claim 9, WEISS teaches that the SPE cartridge can be pre-conditioned to promote a higher retention/retention concentration of target analytes which includes rinsing the SPE cartidge with 2 cartridge volumes of toluene( paragraph 0038). WEISS further teaches that the cartridge can be a cation exchange cartridge (paragraph 0017 , 0039 ). CHIA also teaches of pre-conditioning (paragraph 0014). WEISS and CHIA do not teach of 3 pre-conditioning cartridges or rinses as instantly claimed where there is a polymeric cation exchanger, a weak anion exchanger, and a C18 resin column. GRAHAM is used to remedy this and teaches of using solid phase extraction to isolate analytes or products of (paragraph 0170). GRAHAM further teaches that the SPE cartridges can be weak anion exchange, cation exchange, C18, or polymer variants thereof (paragraph 0170). GRAHAM further teaches of using 4 cartridges which reads on the instantly claimed 3 (paragraph 0075-0094, 0199, 0028). It would have been obvious to one of ordinary skill in the art to use multiple SPE cartridges as is done in GRAHAM in the methods of WEISS and CHIA due to the advantage that using different and multiple types of SPE offer in giving necessary separation of desired components (GRAHAM, paragraph 0009). With respect to Claim 10, WEISS teaches that the SPE cartridge can be pre-conditioned to promote a higher retention/retention concentration of target analytes which includes rinsing the SPE cartidge with 2 cartridge volumes of toluene(paragraph 0038). WEISS further teaches that the cartridge can be a cation exchange cartridge (paragraph 0017, 0039). CHIA also teaches of pre-conditioning (paragraph 0014). WEISS and CHIA do not teach of 3 pre-conditioning cartridges or rinses as instantly claimed where there is a polymeric cation exchanger, a weak anion exchanger, and a C18 resin column. WEISS and CHIA teach of the above, and WEIS further teaches that the SPE cartridge can be pre-conditioned to promote a higher retention/retention concentration of target analytes which includes rinsing the SPE cartridge with 2 cartridge volumes of toluene( paragraph 0038). CHIA also teaches of pre-conditioning (paragraph 0014). WEISS and CHIA do not teach of 3 pre-conditioning cartridges or rinses as instantly claimed. GRAHAM is used to remedy this and teaches of using solid phase extraction to isolate analytes or products of (paragraph 0170). GRAHAM further teaches that the SPE cartridges can be weak anion exchange, cation exchange, C18, or polymer variants thereof (paragraph 0170). GRAHAM further teaches of using 4 cartridges which reads on the instantly claimed 3 (paragraph 0075-0094, 0199, 0028). Further--- the instant claim requires that the fraction can pass through the cartridges together or individually. This encompasses all options possible in which a sample can pass through a cartridge. Therefore, GRAHAM is considered to teach this as shown above. It would have been obvious to one of ordinary skill in the art to use multiple SPE cartridges as is done in GRAHAM in the methods of WEISS and CHIA due to the advantage that using different and multiple types of SPE offer in giving necessary separation of desired components (GRAHAM, paragraph 0009). Claims 1 1-12 are rejected under 35 U.S.C. 103 as being obvious over WEISS/ BL Technologies in WO 2019/099231 (as cited on IDS dated 02/21/2025) in view of CHIA in US 20110259798 further in view of GRAHAM in US 20140296566 and further in view of XU in US 20160145511. With respect to Claim 11, WEISS teaches of quantifying the eluates by ion chromatography, mass spectrometry, nuclear magnetic resonance, surface enhanced Raman scattering, ultra-violet spectrophotometry, fluorescence, conductivity, and combinations thereof (paragraph 0043). CHIA teaches of using ion exclusion chromatography (paragraphs 0017-0018). GRAHAM teaches of multiple SPE extractions. Neither WEISS or CHIA or GRAHAM teach of GC-MS, ion exchange chromatography couple with conductivity detection, or spectroscopy in the infrared region (FTIR) by attenuated reflectance for analysis/detection. XU is used to remedy this and teach of methods for hydroprocessing a feed and for removing things such as nitrogen from it (abstract). XU teaches further of extracting the nitrogen compounds (paragraph 0084) and of analyzing the composition of the feed or extracts by GC-MS (paragraph 0133), or by FTIR (paragraph 0094). It would have been obvious to one of ordinary skill in the art before the effective filing date of the instant invention to analyze the compounds separated as is done in XU in the methods of WEISS and CHIA and GRAHAM due to the fact that different methods such as FTIR and nuclear magnetic resona nce provide different advantages for compounds of different compositions ( XU, paragraph 0094 ). With respect to Claim 11, WEISS teaches of quantifying the eluates by ion chromatography /by cation exchange (paragraph 0053) , mass spectrometry, nuclear magnetic resonance, surface enhanced Raman scattering, ultra-violet spectrophotometry, fluorescence, conductivity, and combinations thereof (paragraph 0043). CHIA teaches of using ion exclusion chromatography (paragraphs 0017-0018). Neither WEISS or CHIA or GRAHAM teach of GC-MS, ion exchange chromatography couple with conductivity detection, or spectroscopy in the infrared region (FTIR) by attenuated reflectance. XU is used to remedy this and teach of methods for hydroprocessing a feed and for removing things such as nitrogen from it (abstract). XU teaches further of extracting the nitrogen compounds (paragraph 0084) and of analyzing the composition of the feed or extracts by GC-MS (paragraph 0133), or by FTIR (paragraph 0094). It would have been obvious to one of ordinary skill in the art before the effective filing date of the instant invention to analyze the compounds separated as is done in XU in the methods of WEISS a nd CHIA and GRAHAM due to the fact that different methods such as FTIR and nuclear magnetic resonance provide different advantages for compounds of different compositions (XU, paragraph 0094). Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to FILLIN "Enter examiner's name" \* MERGEFORMAT REBECCA M FRITCHMAN whose telephone number is FILLIN "Phone number" \* MERGEFORMAT (303)297-4344 . The examiner can normally be reached FILLIN "Work schedule?" \* MERGEFORMAT 9:30-4:30 MT Monday-Friday . 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, Maris Kessel, can be reached on 571- 270-7698 . 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. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /REBECCA M FRITCHMAN/ Primary Examiner, Art Unit 1758
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Prosecution Timeline

Oct 18, 2023
Application Filed
Mar 25, 2026
Non-Final Rejection — §103, §112 (current)

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Expected OA Rounds
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4y 6m
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