CTNF 18/944,112 CTNF 91718 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. Information Disclosure Statement The information disclosure statement (IDS) submitted on 01/30/2025 has been considered by the Examiner. 12-151 AIA 26-51 12-51 Status of Claims Claims 1-20, filed on 11/12/2024, are under consideration. Claim Rejections - 35 USC § 102 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. 07-07-aia AIA 07-07 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 – 07-08-aia AIA (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. 07-15 AIA Claims 1, 3-5, 7-8, 11-12 and 19 are r ejected under 35 U.S.C. 102(a )(1) as being a nticipated b y S ydora (US 2010/0274065). F or claim 1 , Sydora teaches process to oligomerize olefins such as ethylene by contacting with a catalyst composition comprising pyrrole ligands [0006]-[0010], chromium [0012], alkyl/organo aluminum [0091], and an unsaturated compound such as xylene [0114]-[0115], [0117] and [0121]. This unsaturated compound is considered the same as the claimed “aromatic hydrocarbon solvent comprising xylenes. The formed oligomers include hexenes and higher oligomers [0112]. The effluent product includes residual reactants (unreacted ethylene) and the oligomer product [0130] and [0134]. For claims 3-4 , Sydora does not require benzene in the aromatic hydrocarbons. For claim 5 , Sydora teaches Cr:Al ratio of 1:1 to 1:150 [0107], and pyrrole to Cr ratio of 1:1 to 4:1 [0108], and chromium to aromatic ratio of 10-3000 [0117]. These ratios anticipate the molar ratio of chromium:aluminum from 1:1 to 1:150, a molar ratio of pyrrole nitrogen:chromium from 1:1 to 4:1; and a molar ratio of chromium:solvent from 1:10 to 1:10,000. The range disclosed by the reference overlaps/touches the instantly claimed range and therefore; the instantly claimed range is anticipated by the reference as sufficiently supported by specific example(s)—see MPEP 2131.03. For claim 7 , Sydora teaches [0113] one composite catalyst system which may be used in the invention is the combination of chromium (III) ethyl hexanoate, 2,5-diethylpyrrole, triethylaluminum, and diethylaluminum chloride. This composite catalyst system can be used, for example, to trimerize ethylene to form 1-hexene. Other catalyst applicable catalyst systems may be readily discerned from the present disclosure. For claim 8 , Sydora teaches wherein hydrogen is present in step (i) [0126]-[0127]. For claim 11 , Sydora teaches the step of contacting the effluent stream with a catalyst system deactivating agent [0131]. For claim 12 , Sydora teaches the step of separating at least a portion of the unreacted ethylene from the effluent stream ([0130] and [0134]). For claim 19 , Sydora teaches [0155] (catalyst preparation): Anhydrous, degassed ethylbenzene was added to a dry vial in a drybox. To this vial was added neat triethylaluminum (TEA) and neat diethylaluminum chloride (DEAC) . The contents were mixed and allowed to stand for 15 minutes. The selected pyrrole was then slowly added , as gas evolution was observed in most cases. Chromium(III) 2-ethylhexanoate (7.25 wt % Cr in ethylbenzene) was used as the transition metal compound and was added slowly to the alkylaluminum/pyrrole Solution with stirring. The order of catalyst component addition of this claim reciting: (I) combining an aromatic hydrocarbon solvent and an organoaluminum compound, then combining a pyrrole compound, and then a chromium compound, to form a catalyst composition; Sydora also teaches contacting ethylene, an organic reaction medium (cyclohexane), and the catalyst composition in an oligomerization reactor ([0156]) and forming an oligomer product in the oligomerization reactor, the oligomer product comprising hexenes and higher oligomers. The product is discharged from the oligomerization reactor (results and tables), the effluent stream comprising unreacted ethylene and the oligomer product . Claim Rejections - 35 USC § 103 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. 07-21-aia AIA Claims 2, 6, 9-10, 13-16 and 17-18 are rej ected under 35 U.S.C. 103 as being unpatentable over Syd ora (US 2010/0274065). For claim 2 , Sydora suggests the unsaturated compound is aromatic and includes xylene and ethylbenzene [0115] and [0121] “Non-limiting examples of suitable aromatic hydrocarbons that may be utilized singly or in any combination include benzene, toluene, xylene (including ortho-xylene, meta-xylene, para-xylene, or mixtures thereof), and ethylbenzene, or combinations thereof; alternatively, benzene: alternatively, toluene; alternatively, xylene (including ortho-xylene, meta-xylene, para-xylene or mixtures thereof); or alternatively, ethylbenzene”. The combinations of the prior art can reasonably include the claimed amounts of at least 75 wt. % xylenes; and/or from 5 to 25 wt. % ethylbenzene. This overlap establishes a prima facie case of obviousness since the claimed range(s) “overlap or lie inside ranges disclosed by the prior art”—see MPEP 2144.05.I. It would have been obvious to one of ordinary skill in the art to select the claimed range from the broader/overlapping prior art range because the prior art teaches the same utility over the disclosed range. For claim 6 , Sydora teaches Cr:Al ratio of 1:1 to 1:150 [0107], and pyrrole to Cr ratio of 1:1 to 4:1 [0108], and chromium to aromatic ratio of 10-3000 [0117]. These ratios overlap the claimed molar ratio of chromium:aluminum from 1:9 to 1:21; a molar ratio of pyrrole nitrogen:chromium from 2.5:1 to 3.5:1; and a molar ratio of chromium:solvent from 1:300 to 1:1,000; these overlaps establish a prima facie case of obviousness since the claimed range(s) “overlap or lie inside ranges disclosed by the prior art”—see MPEP 2144.05.I. For claim 17 , Sydora suggests making catalyst solution [0155] and then running the oligomerization reaction under ethylene pressure of 850 psig [0156]. Therefore, there is reasonable suggestion that the ethylene is introduced separate from the catalyst since the catalyst solution is added first to the reactor and then ethylene is pressurized. Therefore, and before the effective filing date of the instant invention, it would have been obvious to one of ordinary skill in the art to have introduced ethylene into the oligomerization reactor separately from the catalyst composition because this allows independent flow control for the different reaction components. For claim 18 , Sydora teaches the oligomerization reactor comprises a continuous stirred tank reactor [0128], and the oligomer product is formed at an oligomerization temperature of from 60-200 °C [0124] (which overlaps the claimed 50 to 130 ℃) and an oligomerization pressure of from 300-900 psig [0124] (which overlaps the claimed 250-1,500 psig). For the claimed product composition of claim 9 , ethylene conversion of claim 10 , and selectivity to hexenes/1-hexene in the product composition of claims 13 and 15 , these limitations are viewed as results of the prior art method: "The fact that appellant has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious." —see MPEP 2145 II. It is expected the prior art process provides the claimed limitations because of the similarity in catalyst and reaction conditions discussed above. For claims 14 and 16 , Sydora does not require benzene in the aromatic hydrocarbons or in the process and thus, it is expected that no benzene is present the oligomer product/1-hexene (less than or equal to 5 ppmw benzene or less than or equal to 0.1 ppmw benzene) . Allowable Subject Matter 13-03-01 AIA The following is a statement of reasons for the indication of allowable subject matter: For claim 20 , Sydora teaches catalyst composition comprising: (A) a pyrrole compound; (B) a chromium compound; (C) an organoaluminum compound; and (D) an aromatic hydrocarbon as discussed above in claim 1 rejection. However, Sydora does not explicitly teach the claimed solvent comprising C 9 substituted benzenes; wherein: the aromatic hydrocarbon solvent comprises at least 75 wt. % C 9 substituted benzenes and/or from 5 to 25 wt. % C 10 + substituted benzenes; and the C 9 substituted benzenes comprise a trimethyl benzene, a methyl ethyl benzene, or any combination thereof. No prior art was located to suggest using these types of aromatic solvent in Cr-pyrrole oligomerization. For example, US 4,686,315 discloses using trimethyl benzene solvent in oligomerization using nickel and aluminum, and US 4,410,750 discloses using trimethylbenzene in Zr catalyzed oligomerization (Col 3 line 61) . Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALI Z FADHEL whose telephone number is (571)270-0267. The examiner can normally be reached M-F 9am-6pm PST. 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, In Suk Bullock can be reached at 571-272-5954. 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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. /ALI Z FADHEL/Primary Examiner, Art Unit 1772 Application/Control Number: 18/944,112 Page 2 Art Unit: 1772 Application/Control Number: 18/944,112 Page 3 Art Unit: 1772 Application/Control Number: 18/944,112 Page 4 Art Unit: 1772 Application/Control Number: 18/944,112 Page 5 Art Unit: 1772 Application/Control Number: 18/944,112 Page 6 Art Unit: 1772 Application/Control Number: 18/944,112 Page 7 Art Unit: 1772 Application/Control Number: 18/944,112 Page 8 Art Unit: 1772
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