Prosecution Insights
Last updated: July 17, 2026
Application No. 18/569,645

SHUTDOWN METHOD FOR A PROCESS FOR PREPARING AN OLEFIN OXIDE

Non-Final OA §102§103§112
Filed
Dec 13, 2023
Priority
Jun 15, 2021 — EU 21179509.1 +1 more
Examiner
YOON, TAE H
Art Unit
Tech Center
Assignee
Dow Global Technologies LLC
OA Round
1 (Non-Final)
66%
Grant Probability
Favorable
1-2
OA Rounds
3m
Est. Remaining
91%
With Interview

Examiner Intelligence

Grants 66% — above average
66%
Career Allowance Rate
971 granted / 1462 resolved
+6.4% vs TC avg
Strong +25% interview lift
Without
With
+24.9%
Interview Lift
resolved cases with interview
Typical timeline
2y 10m
Avg Prosecution
35 currently pending
Career history
1485
Total Applications
across all art units

Statute-Specific Performance

§101
0.2%
-39.8% vs TC avg
§103
73.8%
+33.8% vs TC avg
§102
1.5%
-38.5% vs TC avg
§112
9.8%
-30.2% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1462 resolved cases

Office Action

§102 §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 A third party has submitted IDS listing WO 2016/128538 A1 (Aug. 25, 2016) which is in the file and thus. Thus, an initialed IDS and a copy of WO are enclosed. 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 applicant regards as his invention. Claims 16, 17 and 21-27 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. Claim 16 recites t1 for steps (a), (b) and (c) and it is unclear the t1 is same duration or not for the steps (a), (b) and (c). Further, it is unclear whether the recited steps (a), (b) and (c) occur simultaneously or separately. If the recited steps (a), (b) and (c) occur simultaneously, the recited over t1 in step (b) of claim 16 should be “over the t1” for a proper antecedent basis. The same reason would apply to the steps (a), (b) and (c) of claim 28. Claim 17 recites t2 for steps (e) and (f) and it is unclear the t2 is same duration or not for the steps (e) and (f). If the recited steps (d), (e) and (f) occur simultaneously, the recited “over t2” in step (e) of claim 16 should be “over the t2” for a proper antecedent basis. The same reason would apply to the steps (d), (e) and (f) of claim 29. Claims 18-19 depend from the indefinite claim 16 would be also indefinite. Further claim 18 is dependent on claim 16 in which steps (a), (b) and (c) are recited. Thus, the recited step (g) of claim 19 would lack an antecedent basis. Ex parte Miyazaki, No. 2007-3300, 2008 WL 5105055, at 5 (BPAI Nov. 19, 2008) 89 USPQ2d 1207: [I]f a claim is amendable to two or more plausible claim constructions, the USPTO is justified in requiring the applicant to more precisely define the metes and bounds of the claimed invention by holding the claim unpatentable under 35. USC 112, 2nd paragraph, as indefinite. MPEP 2175 and 2143.03. Claim 21 is dependent on claim 16 in which steps (a), (b) and (c) are recited. Thus, the recited step (d) and step (g) would lack an antecedent basis. Claim 22 depends from the indefinite claim 21 would be also indefinite. Claim 24 is dependent on claims 16 and 23 and thus the recited steps (d) and (g) would lack an antecedent basis. Claims 25-27 depend from the indefinite claim 16 would be also indefinite. The recited “subjecting the reaction mixture from (I)” in line 6 of claim 28 is indefinite since the “(I)” would lack an antecedent basis. Claim 30 depends from the indefinite claim 28 would be also indefinite. Claim 30 recites t3 for a step (g) and it is unclear the t3 is same duration or not for the steps (e) and (f) of claim 29. Further, it is unclear whether the recited steps (a), (b) and (c) of claim 29 and steps (d), (e), (f) and (g) of claims 29 and 30 occur simultaneously or separately Claim Rejections - 35 USC § 102 and 35 USC § 103 The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action: A person shall be entitled to a patent unless – (a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention. 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. Claims 16-23 and 25-30 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by WO 2016/128538 A1 (Aug. 25, 2016). WO teaches a method of obtaining propylene oxide continuously in presence of a catalyst comprising a titanium containing zeolite (i.e., heterogeneous epoxidation catalyst) in lines 1-13 of page 2 meeting the instantly recited normal run stage of claim 1. WO teaches a shutdown stage by stopping introducing the feed stream comprising the hydrogen peroxide) into the reactor while continuously introducing propene and organic solvent (i.e., acetonitrile) in lines 4-15 of page 48 and lines 5- 10 of page 62 which would exhaust the hydrogen peroxide due to flushing H2O2, propylene and propylene oxide. WO further teaches a concentration of hydrogen peroxide is 0.0001% by weight based on an aqueous mixture in lines 21-23 of page 48. Thus, the concentration of hydrogen peroxide would be less than 0.0001% by weight based on a total mixture further comprising the olefin and organic solvent which would meet the instantly recited less than 0.2 wt.% of the hydrogen peroxide during a shutdown stage. Further, WO teaches removing the propene followed by draining the acetonitrile and water in lines 16-20 of page 61 which would meet the recited step (c) of claim 16 since the recited step (c) would encompass two-step removals taught by WO. Thus, the instant invention lacks novelty. Regarding claim 17, WO teaches that the reactor was flushed free of H2O2, propylene and propylene oxide by passing a mixture of acetonitrile (80 wt.%) and water (20 wt.%) through the reactor wherein the temperature of this mixture was 50oC, followed by draining the major portion of the acetonitrile and water from the reactor in lines 16-20 of page 61 meeting the recited step (d). Regarding the recited step (e), WO teaches contacting the organic solvent from (d) under epoxidation conditions since WO teaches the acetonitrile and propene are provided until the epoxidation in the tubes was completed. Regarding the recited step (f), WO teaches draining the major portion of the acetonitrile and water from the reactor. Regarding claim 18, WO teaches providing a gaseous stream (i.e., nitrogen) into the epoxidation zone in lines 14-15 of page 52. Regarding claim 19, WO teaches providing the nitrogen in lines 14-15 of page 52 which would be expected to comprise near 100% of the nitrogen inherently. Regarding claim 20, WO teaches “the acetonitrile and propene flows were continued until the epoxidation in the tubes was completed in lines 14-16 of page 16 meeting claim 20. Regarding claims 21-22, WO teaches “At that point in time, the epoxidation reaction was stopped by stopping the flow of hydrogen peroxide; the acetonitrile and propene flows were continued until the epoxidation in the tubes was completed in lines 14-16 of page 61. WO further teaches the pressure at the reactor exit is kept constant at 20 bar (i.e. 2 MPa) in lines 30-31 of page 53. WO teaches that output stream 6 is sent to light boiler separation column that is operated at 1.1 bar (i.e., 0.11 MPa). Thus, WO teaches reducing the pressure from 2 MPa to 0.11 MPa meeting claims 21 and 22. Regarding claim 23, WO teaches that Stream (3a) was an aqueous stream comprising dissolved potassium formate in line 1 of page 54 and the potassium formate would meet the recited additive. Regarding claim 25, WO teaches the catalyst comprising a titanium containing zeolite (i.e., heterogeneous epoxidation catalyst) in lines 1-13 of page 2 Regarding claim 26, WO teaches “organic solvents to be employed in (a1) are in principle all solvents known for this purpose” in lines 3-6 of page 4 and the instant invention teaches the same solvent in lines 36-49 at page 9 of the specification. Regarding claim 27, WO teaches a shutdown stage by stopping introducing the feed stream comprising the hydrogen peroxide) into the reactor while continuously introducing propene and organic solvent (i.e., acetonitrile) in lines 4-15 of page 48 and the propene is C3 alkene. Regarding claim 28, the normal run stage and shutdown stage discussed above would meet the claim 28. See Example 2.1 and Reference Example 2. Regarding claim 29, see Example 2.1. WO teaches that the reactor was flushed free of H2O2, propylene and propylene oxide by passing a mixture of acetonitrile (80 wt.%) and water (20 wt.%) through the reactor wherein the temperature of this mixture was 50oC, followed by draining the major portion of the acetonitrile and water from the reactor in lines 16-20 of page 61 meeting the recited step (d). Regarding the recited step (e), WO teaches contacting the organic solvent from (d) under epoxidation conditions since WO teaches the acetonitrile and propene are provided until the epoxidation in the tubes was completed. Regarding the recited step (f), WO teaches draining the major portion of the acetonitrile and water from the reactor. Regarding claim 30, WO teaches providing a gaseous stream (i.e., nitrogen) into the epoxidation zone in lines 14-15 of page 52. Claims 16-23 and 25-30 are rejected under 35 U.S.C. 103 as being unpatentable over WO 2016/128538 A1 (Aug. 25, 2016) in view of Qin et al. (US 7,057,056). Regarding the recited olefin other than the propene taught by WO, Qin et al. teach an epoxidation process comprising reacting an olefin with hydrogen peroxide in the presence of a titanium or vanadium zeolite (i.e., catalysts, see example 1) in claim 1 and lines 47-62 of col. 4. The olefin taught by Qin et al. would encompass the instant olefin such as C2-C10 alkene of claim 27. Thus, it would have been obvious to one skilled in the art before the effective filing date of invention to utilize other olefins taught by Qin et al. in WO since the epoxidation process utilizing the olefin which would encompass the C2-C10 alkene is known as taught by Qin et al. absent showing otherwise. Selection of a known material based on its suitability for its intended use is prima facie obvious, see Sinclair & Carroll Co. v. Interchemical Corp., 325 US 327, 65 USPQ 297 (1945). MPEP 2144.07. The combination of familiar elements according to known methods is likely to be obvious when it does no more than yield predictable results. KSR Co. v. Teleflex Inc., 550 U.S. 398, 416 (2007). MPEP 2141. EXAMINER’S COMMENT The following prior art and not relied upon is considered pertinent to applicant's disclosure. WO 2016/131652 A1 (Aug. 25, 2016) teaches a method for the epoxidation of an olefin with hydrogen peroxide continuously in lines 5 of page 2. Although WO teaches a concentration of hydrogen peroxide is 0.1 to 1.0% by weight in lines 21-29 of page 5 overlapping the instantly recited less than 0.2 wt.%, the concentration is based on an aqueous mixture, not on the instant total mixture. Any inquiry concerning this communication or earlier communications from the examiner should be directed to TAE H YOON whose telephone number is (571)272-1128. The examiner can normally be reached Mon-Fri. 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, Robert Jones can be reached at (571)270-7733. 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. /TAE H YOON/Primary Examiner, Art Unit 1762
Read full office action

Prosecution Timeline

Dec 13, 2023
Application Filed
Jun 22, 2026
Non-Final Rejection mailed — §102, §103, §112 (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

1-2
Expected OA Rounds
66%
Grant Probability
91%
With Interview (+24.9%)
2y 10m (~3m remaining)
Median Time to Grant
Low
PTA Risk
Based on 1462 resolved cases by this examiner. Grant probability derived from career allowance rate.

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