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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 03/17/2026 has been entered.
Claims 1-10, 12, 14, and 16 are currently pending and have been fully considered.
Claims 11, 13, 15 and 17-21 have been cancelled.
Claims 1, 12, and 14 have been amended.
Claim Interpretation
Claim 1 has been amended to state “wherein said components forming-form an in situ catalytic composition once all five of said components are combined and wherein the components of the catalytic composition all five of said components are not mixed all together prior to contacting ethylene”
The claims have been interpreted to state that the catalyst composition is formed only after all five of said components are formed.
The claim has also been interpreted to state that some of the 5 components can be mixed together prior to contacting ethylene as long as all 5 of said components are not mixed all together prior to contacting ethylene.
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.
Claim(s) 1-10, 12, 14, and 16 is/are rejected under 35 U.S.C. 103 as being unpatentable over KNUDSEN (USPGPUB 2001/0053742) in view of MORGAN et al. (The Effect of Aromatic Ethers on the Trimerisation of Ethylene using a Chromium Catalyst and Aryloxy Ligands).
KNUDSEN teaches olefin production catalyst systems.
Regarding claim 1, KNUDSEN teaches in paragraph 31 that when the reactant is predominately ethylene, a temperature in the range of about 0 to about 300°C. generally can be used.
A prima facie case of obviousness exists wherein the claimed ranges overlap. (90°C and 190°C)
The olefin production catalyst system is taught in paragraph 12 to comprises a chromium source, a pyrrole-containing compound and a metal alkyl, all of which have been contacted and/or reacted in the presence of an unsaturated hydrocarbon.
The chromium source is taught in paragraph 13 to include chromium halides. (a metal precursor of chromium)
The pyrrole containing compound is taught in paragraph 16 to include any pyrrole-containing compound, or pyrrollide, that will react with a chromium source to form a chromium pyrrollide complex. (a pyrrole derivative)
The metal alkyl is taught in paragraphs 19-20 to include alkylaluminum compounds, derivatives of alkylaluminum compounds, halogenated alkylaluminum compounds, and mixtures thereof.
The formulas include AlR3, AIR2X, AlRX2, AlR2(OR), and/or AlRX(OR), wherein R is an alkyl group and X is a halogen.
Examples include triethylaluminum, tripropylaluminum, tributylaluminum, diethylaluminum chloride, diethylaluminum bromide, diethylaluminum ethoxide, diethylaluminum phenoxide, ethylaluminum dichloride atom, and mixtures thereof.
Triethylaluminum is an aluminum-based compound of general formula AIR2R3R4 wherein the R2, R3, R4, are identical as C2 alkyl groups. (C1-C20 alkyl, C1-C20 alkoxy and C5-C30 aryloxy groups)
Diethylaluminum chloride is a halogenated aluminum-based compound of general formula AInR5oYp wherein the R5 is C2 alkyl groups with n being 2. (C1-C20 alkyl groups) O is 2. (integer from 1-3) Y is chlorine. (halogen) P is 1. (integer from 1-3)
The unsaturated hydrocarbon is taught in paragraph 23 to include any aromatic hydrocarbon.
KNUDSEN teaches in paragraph 8 that an improved process wherein the heat generated by the preparation reaction can be controlled by preparing said catalyst system in-situ in the presence of the trimerization reactants. Trimerization reactants are taught in paragraph 24 to include ethylene.
KNUDSEN further teaches in paragraphs 7 and 10 that the olefin production catalyst system comprising already contacting the chromium compound, the pyrrole-containing compound, and the non-hydrolyzed aluminum alkyl compound in the presence of an unsaturated hydrocarbon compound prior to contacting an olefin reactant. (simultaneously bringing ethylene into contact with the said components forming in situ a catalytic composition)
KNUDSEN further teaches in paragraph 27 that contacting of monomer or monomers with a catalyst system can be effected by any manner known in the art. Other known contacting methods may also be employed. KNUDSEN further teaches in paragraph 87 that all changes and modifications within the spirit and scope may be considered.
KNUDSEN explicitly teaches in paragraph 3 that stirring during catalyst preparation can cause particulates in a catalyst system product which can result in low activity and productivity of the resultant catalyst system. KNUDSEN teaches in paragraph 11 and paragraphs 37-44 examples and embodiments in which some components of the catalyst system are mixed prior to some components are added.
KNUDSEN further teaches in paragraphs 59 and 84 examples that did not comprise any stirring (mixing) in preparing the catalyst system.
KNUDSEN also teaches in paragraph 8 that an improved process wherein the heat generated by the preparation reaction can be controlled by preparing said catalyst system in-situ in the presence of the trimerization reactants.
It would be obvious to one of ordinary skill in the art to preparing the catalyst system that KNUDSEN teaches in situ where some or none of the catalytic components are mixed together prior to addition into a reactor where some or all of the catalytic components are introduced simultaneously with a different feed of ethylene. (wherein all five of said components are not mixed all together prior to contacting ethylene)
KNUDSEN teaches run 203 in paragraphs 58-59 and run 205 in paragraph 63 are performed wherein the reactor contents are explicitly not stirred during the reaction.
It is noted that (Selection of any order of mixing ingredients is prima facie obvious.) See Ex parte Rubin, 128 USPQ 440 (Bd. App. 1959) (Prior art reference disclosing a process of making a laminated sheet wherein a base sheet is first coated with a metallic film and thereafter impregnated with a thermosetting material was held to render prima facie obvious claims directed to a process of making a laminated sheet by reversing the order of the prior art process steps.). See also In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) (selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results); In re Gibson, 39 F.2d 975, 5 USPQ 230 (CCPA 1930).
KNUDSEN teaches in reference claims 11 and 23 that the contacting the olefin production catalyst system with ethylene may occur in the presence of an aromatic compound.
KNUDSEN further teaches in paragraph 23 exemplary unsaturated, aromatic hydrocarbons include, but are not limited to, toluene, benzene, ethylbenzene, xylene, mesitylene, hexamethylbenzene, and mixtures thereof. Unsaturated, aromatic hydrocarbons are preferred in order to improve catalyst system stability, as well as produce a highly active catalyst system in terms of activity and selectivity. Preferred unsaturated aromatic hydrocarbons are selected from the group consisting of toluene, ethylbenzene and mixtures thereof for best resultant catalyst system stability and activity.
It is noted that the present claims teach that the aromatic additive comprises aromatic ether and/or aromatic hydrocarbon. It is claimed to include alternatives.
KNUDSEN teaches in paragraph 54 an example with 201.7 grams of chromium(III) 2-ethylhexanoate and 1000 ml of toluene and 13.7 lbs of toluene. Chromium(III) 2-ethylhexanoate has a molar mass of 481.6 g/mol. 201.7 grams of chromium(III) 2-ethylhexanoate is about 0.41 mol. 1000 ml of toluene is about 9.4 mols of toluene. 13.7 lbs of toluene is about 67 mols.
It would be obvious to one of ordinary skill in the art to use similar molar ratios of chromium compound to toluene with toluene as the aromatic hydrocarbon.
76 mol of aromatic solvent to 0.41 mol of chromium compound would be equivalent to 185 mol of toluene to 1 mol of chromium compound.
In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990) Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art at the time of the invention.
Regarding claim 12, the claim is dependent on claim 1 and the aromatic additive may comprise an aromatic hydrocarbon and not an aromatic ether.
Regarding claim 2, KNUDSEN teaches in paragraphs 53-54 and 58-59 a run 203 in which triethylaluminum (TEA) and diethylaluminum chloride (DEAC) are combined in a mix tank to form an aluminum alkyl mixture. The aluminum alkyl mixture is then fed into the reactor.
Regarding claim 3, KNUDSEN teaches in paragraph 51 first combining the aluminum alkyl compounds and then contacting the pyrrole-containing compound.
It would be well within one of ordinary skill in the art to modifying run 203 by combine and mixing the 2,5-dimethylpyrrole (2,5 DMP) with the aluminum alkyl mixture prior to adding to the reactor with a reasonable expectation of success.
KNUDSEN teaches in paragraph 51 that the order of addition either first combining the aluminum alkyl compounds and then contacting the pyrrole-containing compound or first adding the pyrrole-containing compound to one of the aluminum alkyl compounds and then adding another aluminum alkyl compound does not effect catalyst system activity or productivity.
Regarding claim 4, KNUDSEN teaches in paragraph 12 a pyrrole-containing compound and a metal alkyl, all of which have been contacted in the presence of an unsaturated hydrocarbon to act as the catalyst system. KNUDSEN further teaches in paragraph 51 preparing the catalyst System prior to contacting ethylene.
Regarding claim 5, KNUDSEN teaches in paragraphs 53-54 and 58-59, a run 203 in which chromium tris(2-ethylhexanoate) (Cr(EH))chromium is first dissolved in toluene and stirred in the reactor.
Regarding claim 6, KNUDSEN teaches in paragraph 35 a continuous reactor.
Mixing the olefin production catalyst system as it comes into contact with ethylene in a continuous reactor would be well within one of ordinary skill in the art as mixing in reactors is well known.
KNUDSEN, for example, teaches in paragraph 85 that stirring results in polymer production and formation significantly higher than without stirring.
Regarding claim 7, KNUDSEN teaches in paragraph 31 that when the reactant is predominately ethylene, a temperature in the range of about 0 to about 300°C. generally can be used.
A prima facie case of obviousness exists wherein the claimed ranges overlap. (95°C and 185°C)
Regarding claim 8, KNUDSEN teaches in paragraph 30 that hydrogen can be added to the reactor to accelerate the reaction and/or increase catalyst system activity.
Regarding claim 9, KNUDSEN teaches in paragraph 18 that the pyrroles include pyrrole (CHN), and 2,5-dimethylpyrrole.
2,5-dimethylpyrrole meets the present limitations with R1 as a C1, (methyl group), m is 2 and X is hydrogen.
Regarding claim 10, KNUDSEN teaches in paragraph 37 a catalyst system that comprises 2.8 ml triethylaluminum (TEA) and 3.2 ml diethylaluminum chloride (DEAC). KNUDSEN further teaches in paragraph 38 examples with molar ratios of TEA/DEAC as 50/63. The molar ratio of DEAC to the combination of TEA and DEAC would be 63/113.
A prima facie case of obviousness exists wherein the claimed ranges overlap.
Regarding claim 14, KNUDSEN teaches in paragraph 23 that the aromatic hydrocarbons include toluene which meets the present limitations with R9 as a C1, (methyl group), and s is 1.
Regarding claim 16, KNUDSEN teaches in paragraph 31 that when the reactant is predominately ethylene, a temperature in the range of about 0 to about 300°C. generally can be used.
A prima facie case of obviousness exists wherein the claimed ranges overlap. (100°C and 160°C)
Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art at the time of the invention.
Claim(s) 12 is alternatively rejected under 35 U.S.C. 103 as being unpatentable over KNUDSEN (USPGPUB 2001/0053742) as applied to claims 1-10, 12, 14, and 16 above, and further in view of MORGAN et al. (The Effect of Aromatic Ethers on the Trimerisation of Ethylene using a Chromium Catalyst and Aryloxy Ligands).
The above discussion of KNUDSEN is incorporated herein by reference.
KNUDSEN teaches in reference claims 11 and 23 that the contacting the olefin production catalyst system with ethylene may occur in the presence of an aromatic compound.
MORGAN et al. teach on page 939 adding an aromatic ether such as anisole for the selective trimerization of ethylene with a chromium source and an alkylammonium activator.
It would be obvious to one of ordinary skill in the art to add anisole as the aromatic compound in KNUDSEN.
MORGAN et al. teach on page 939 that an aromatic ether such as anisole substantially increase the activity and selectivity of a system.
Anisole would meet the present limitations with q and r being 0, and R6 being CH3, a C1 alkyl group.
KNUDSEN teaches in paragraph 54 an example with 201.7 grams of chromium(III) 2-ethylhexanoate and 1000 ml of toluene and 13.7 lbs of toluene. Chromium(III) 2-ethylhexanoate has a molar mass of 481.6 g/mol. 201.7 grams of chromium(III) 2-ethylhexanoate is about 0.41 mol. 1000 ml of toluene is about 9.4 mols of toluene. 13.7 lbs of toluene is about 67 mols.
It would be obvious to one of ordinary skill in the art to use similar molar ratios of chromium compound to anisole with anisole as the aromatic compound that serves as solvent.
76 mol of aromatic solvent to 0.41 mol of chromium compound would be equivalent to 185 mol of aromatic solvent to 1 mol of chromium compound.
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." In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955)
Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art at the time of the invention.
Response to Arguments
Applicant's arguments filed 04/22/2026 have been fully considered but they are not persuasive.
Applicant argues that the claims have been amended to state the molar ratio between the aromatic ether and the chromium-based metal precursor and that the previous rejections should be withdrawn.
The 112 rejections have been withdrawn and the 103 rejections have been withdrawn. New grounds of rejections based on the same references have been made.
The declaration under 37 CFR 1.132 filed 03/17/2026 is insufficient to overcome the rejection of claims based upon KNUDSEN (USPGPUB 2001/0053742) as set forth in the last Office action because: the facts presented are not germane to the rejection at issue.
KNUDSEN teaches an example ratio between a chromium compound and the toluene with a specific ratio that falls within the claimed range.
Applicant has also appeared to state that the ratios of aromatic hydrocarbon or aromatic ether to the chromium compounds are a matter of optimization.
Furthermore, it has been established that (selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results); In re Gibson, 39 F.2d 975, 5 USPQ 230 (CCPA 1930) (Selection of any order of mixing ingredients is prima facie obvious.)
Given that KNUDSEN also further teaches in paragraph 51 that the order of addition either first combining the aluminum alkyl compounds and then contacting the pyrrole-containing compound or first adding the pyrrole-containing compound to one of the aluminum alkyl compounds and then adding another aluminum alkyl compound does not effect catalyst system activity or productivity, one of ordinary skill in the art would change the order of addition and mixing of select compounds together and expect a reasonable expectation of success.
Applicant has not provided evidence of new or unexpected results based on the selection of order of mixing the ingredients.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
LASHIER (EP0780353B1) teaches a process for the oligomerization of olefins.
LASHIER teaches that the olefin may be ethylene. (Para 12)
In the case of trimerization, the reaction temperature and pressures are taught to be those that can trimerize the olefin reactants. Generally, the range for temperatures is from 0 to 250°C. (Para 29 and 30)
The oligomerization of olefins is performed with catalyst systems. The catalyst system comprises a chromium source, a pyrrole-containing compound and a metal alkyl, all of which have been contacted and/or reacted in the presence of an unsaturated hydrocarbon. (Para 12)
WANG (USPGPUB US-2012/0310025-A1) teaches synthesizing 1-Hexene from ethylene trimerization with 5 components: a compound containing P and N, an electron donor, a chromium compound, a carrier and an accelerator. The accelerator is taught in paragraph 13 to include aluminum compounds.
WANG teaches in paragraph 16 that all 5 components can be mixed prior to adding to the reactor or all 5 components may be directly added to the reactor with ethylene introduced to undergo trimerization.
REAGAN (EP-608447-B1) teaches a process for the preparation of a catalyst for olefin polymerization. REAGAN teaches a mixture of a chromium salt, a metal amide, particularly a pyrrolide, and an electron pair donor solvent, such as, for example, an ether, and reaction with an unsaturated hydrocarbon are disclosed, including use of pyrrole or derivatives thereof as the pyrrolide and an aliphatic as the unsaturated hydrocarbon.
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/MING CHEUNG PO/ Examiner, Art Unit 1771
/ELLEN M MCAVOY/ Primary Examiner, Art Unit 1771
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