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 .
Response to Amendment
The rejection of claims 1-5, 7-8, 10, 17, and 18 under 35 USC § 102(b) anticipated by CN113198519A1 is withdrawn by the examiner in view of the amendment filed on 4/1/2026.
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.
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Claims 1-19 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-16 of copending Application No. 18/738,261 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because both sets of claims drawn to a process for isomerization of an input stream comprising trimethylpentene isomers.
The copending claimed set does not disclose a stream B containing 80–92 wt.% 2,4,4-trimethylpent-2-ene, the instant claims differ from the claims of the copending application only in the recitation of a particular concentration range for the TMP-2 enriched stream. Optimization of stream compositions in distillation systems through adjustment of reflux ratio, pressure, feed location, and number of theoretical stages constitutes routine optimization of result-effective variables within the level of ordinary skill in the art.
There are minor differences between the two sets of claims and such differences would have been obvious to one of skill in the art.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
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 1-19 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 1 recites: “an input stream with which the process is fed and which contains 2,4,4-trimethylpent-2-ene and 2,4,4-trimethylpent-1-ene is sent to the distillation unit in a) in addition to stream A and/or to the isomerization in b) in addition to stream B.” The phrase “an input stream with which the process is fed” renders the claim unclear because it is not clear whether this stream is distinct from stream A or stream B, or whether it may be identical to one of those streams.
Furthermore, the phrase “in addition to stream A and/or to the isomerization in b) in addition to stream B” renders the scope of the claim unclear because it is not clear which of the recited alternatives are required or whether multiple alternatives must occur simultaneously.
Claims 1–5, 7–8, 10, 17, and 18 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by CN113198519A.
Thus, the CN reference discloses a distillation-isomerization-recycle process for converting internal olefins to terminal olefins, which reads on the process of claims 1–5, 7–8, 10, 17, and 18.
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 1-5 and 7-19 are rejected under 35 U.S.C. 103 as being unpatentable over CN113198519A in view of Gartside et al. (US 6,875,901 B2) and further in view of Dakka et al. (US 2003/0100811 A1).
The CN reference discloses a method for producing high-purity alpha-olefins using a reaction-rectification system comprising a distillation column and an isomerization reactor.
The CN teaches:
feeding an olefin mixture comprising internal and terminal olefins including 2,4,4-trimethyl-1-pentene and 2,4,4-trimethyl-2-pentene to a rectification tower for separation;
withdrawing a top stream enriched in terminal olefin (alpha-olefin);
withdrawing a bottom stream enriched in internal olefin;
sending the internal olefin stream to an isomerization reactor containing a silicon-aluminum molecular sieve catalyst;
converting internal olefin to terminal olefin by isomerization; and
recycling the reaction product to the distillation column.
the rectification tower may comprise multiple theoretical plates and operates with reflux;
the internal olefin stream is withdrawn from the bottom of the column and fed to the reactor; and
the isomerization reactor employs a silicon-aluminum molecular sieve catalyst, which is a
zeolite-type catalyst.
The CN reference does not teach producing the claimed TMP-2 concentration range.
Gartside teaches an olefin isomerization process comprising:
contacting an olefin feed with an isomerization catalyst in a reactor,
sending the reactor effluent to a fractionation column, and
recycling unreacted olefin to the reactor.
For example:
internal olefins are converted to terminal olefins via catalytic isomerization (col. 2, lines 20–33);
the process includes an isomerization reactor, fractionation column, and recycle stream (col. 3, lines 40–67); and
suitable catalysts include solid catalysts such as metal oxides (col. 4, lines 38–45).
Dakka teaches zeolite catalysts used in hydrocarbon conversion processes, including beta zeolite catalysts having defined silica-to-alumina ratios suitable for olefin reactions (¶[0017]–[0028]).Claim 6 recites a concentration range of TMP-2-ene in stream B.
The CN reference to produce the claimed TMP-2 concentration range. However, the CN
reference expressly teaches:
separation of TMP-1 and TMP-2 via rectification ([0022]-[0023]);
recycling of the TMP-2 enriched stream to an isomerization reactor ([0022]); and
adjustment of reflux ratio, tower pressure, feed stage location, and operating conditions to obtain desired separation results ([0020], [0022]-[0023]).
Example 5 of the CN reference further teaches operation of the rectification tower at a reflux ratio of 6:1, a tower-top pressure of 101 kPaA, and defined tower temperatures for obtaining separation between TMP-1 and TMP-2 ([0061]).
The claimed concentration range of 80–92 wt.% TMP-2 in stream B represents a result-effective variable obtainable through routine optimization of distillation operating conditions including reflux ratio, pressure, feed stage location, and number of theoretical stages.
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 conditions of CN113198519A to obtain a stream B containing 80–92 wt.% 2,4,4-trimethylpent-2-ene because optimization of distillation stream compositions is a routine engineering consideration in hydrocarbon separation processes.
Claim 9 recites that stream B is withdrawn as a side stream from the distillation column.
Gartside teaches fractionation columns separating olefin isomers and producing multiple product and recycle streams (col. 3, lines 52–67).
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 distillation column of the CN reference to include a side-stream withdrawal as taught by Gartside, because withdrawing intermediate streams from distillation columns is a conventional configuration used to recover intermediate boiling components.
Claims 11–13
These claims recite zeolite catalysts including beta zeolite and specific Si:Al ratios.
Dakka teaches beta zeolite catalysts having defined silica-to-alumina ratios for hydrocarbon conversion processes (¶[0022]–[0028]).
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 isomerization catalyst of The CN reference to employ the beta zeolite catalysts taught by Dakka, because zeolite catalysts are widely used for hydrocarbon conversion and olefin isomerization reactions.
Claim 14 recites an ion-exchange resin catalyst.
Gartside teaches the use of solid catalysts for olefin isomerization reactions (col. 4, lines 38–45).
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 catalyst of the CN reference process to employ another known solid acid catalyst such as an ion-exchange resin, because substitution of known catalysts for similar reactions is a routine design choice.
Claim 15 recites heat integration between the condenser and reboiler of the distillation column.
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 distillation system of the CN reference to include heat integration between condenser and reboiler streams, because heat integration is a well-known technique used to improve energy efficiency in distillation systems.
Claim 16 recites that the distillation unit comprises two distillation columns.
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 the CN reference to employ multiple distillation columns, because multi-column fractionation systems are commonly used in hydrocarbon separation processes.
Claim 19 recites vapor compression or heat-pump assisted distillation.
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 distillation system of the CN reference to incorporate heat-pump or vapor-compression technology, because such systems are known methods for improving the energy efficiency of distillation processes.
Response to Arguments
Applicant’s arguments regarding the provisional nonstatutory obviousness-type double patenting rejection over claims 1–16 of co-pending Application No. 18/738,261 have been fully considered but are not persuasive. Although Applicant argues that the reference claims do not disclose a stream B containing 80–92 wt.% 2,4,4-trimethylpent-2-ene, the instant claims differ from the claims of the copending application only in the recitation of a particular concentration range for the TMP-2 enriched stream. Optimization of stream compositions in distillation systems through adjustment of reflux ratio, pressure, feed location, and number of theoretical stages constitutes routine optimization of result-effective variables within the level of ordinary skill in the art, as evidenced by CN113198519A teaching adjustment of reflux ratio, tower pressure, feed stage location, and separation conditions for obtaining desired olefin separations ([0020], [0022]-[0023]). Accordingly, the claims of the instant application are considered an obvious variation of the claims of Application No. 18/738,261 and the provisional nonstatutory obviousness-type double patenting rejection is maintained.
Applicant’s arguments regarding the rejection under 35 U.S.C. 112(b) have been fully considered but are not persuasive. Although Applicant asserts that the amended claim language clarifies that the input stream is distinct from stream A and stream B, the claim remains unclear regarding the required relationship between the recited alternatives.
Specifically, claim 1 recites:
“the input stream ... is sent to the distillation unit in a) in addition to stream A and/or to the
isomerization in b) in addition to stream B.”
It remains unclear whether:
the input stream must be sent to the distillation unit only,
to the isomerization only,
to both simultaneously,
or optionally to either location.
Additionally, the boundaries of the “and/or” relationship are unclear because the claim does not positively recite which process configuration is required. Accordingly, the metes and bounds of the claimed invention cannot be determined with reasonable certainty and the rejection under 35 U.S.C. 112(b) is maintained.
Applicant argues that the CN reference discloses only a bottoms stream containing 55.1 wt.%
TMP-2 and therefore fails to disclose the claimed 80–92 wt.% range. Applicant further argues
that the CN reference relates to streams containing significant amounts of other isomers.
However, the CN reference expressly teaches:
separation of TMP-1 and TMP-2 via rectification ([0022]-[0023]);
recycling of the TMP-2 enriched stream to an isomerization reactor ([0022]); and
adjustment of reflux ratio, tower pressure, feed stage location, and operating conditions to obtain desired separation results ([0020], [0022]-[0023]).
Example 5 of the CN reference further teaches operation of the rectification tower at a reflux ratio of 6:1, a tower-top pressure of 101 kPaA, and defined tower temperatures for obtaining separation between TMP-1 and TMP-2 ([0061]).
The claimed concentration range of 80–92 wt.% TMP-2 in stream B represents a result-effective variable obtainable through routine optimization of distillation operating conditions including reflux ratio, pressure, feed stage location, and number of theoretical stages.
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 conditions of the CN reference to obtain a stream B containing 80–92 wt.% 2,4,4-trimethylpent-2-ene because optimization of distillation stream compositions is a routine engineering consideration in hydrocarbon separation processes.
Applicant further argues that the CN reference employs reactive distillation while the present application separately performs distillation and isomerization. However, the CN reference expressly discloses a rectification tower and a separate backpack reactor connected through recycle streams ([0019], [0022], Fig. 1). The reference therefore teaches separate distillation and isomerization zones connected in a recycle loop.
Applicant additionally argues that Gartside does not disclose side-stream withdrawal or flexible feed introduction. However, Gartside teaches fractionation systems employing recycle streams and multiple process stream configurations (col. 3, lines 40–67), including recycle of unreacted olefin streams between a reactor and a fractionation system.
With respect to claim 19, Applicant argues that no supporting reference was cited. The Examiner notes that vapor-compression and heat-pump assisted distillation systems are notoriously well known in the chemical engineering arts for improving distillation energy efficiency. See, for example, Kiss et al., Heat Pumps in Distillation, AIChE Spring National Meeting Proceedings (2009), teaching vapor recompression and heat-pump integration in distillation columns.
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 distillation system of the CN reference to employ vapor-compression or heat-pump assisted distillation because such systems are known methods for improving distillation energy efficiency.
Conclusion
THIS ACTION IS MADE FINAL. 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 TAM M NGUYEN whose telephone number is (571)272-1452. The examiner can normally be reached Mon - Frid.
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 C Singh can be reached at 571-273-6381. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/TAM M NGUYEN/Primary Examiner, Art Unit 1771
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