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 .
The amendments filed 6/22/26 overcome the rejections set forth under 35 USC 112(b) and 35 USC 101 in the office action mailed 3/27/26. A new ground of rejection under 35 USC 112(b), necessitated by the amendments, is set forth below. The amendments do not overcome the rejections set forth under 35 USC 102 over Zhou, which is maintained below. The rejection set forth under 35 USC 103 over Zhou is also maintained below, and the discussion of the rejection has been updated as necessitated by the amendments.
Claim Rejections - 35 USC § 112
Claims 16-18 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.
Lines 5-6 of claim 16 recite “the unsupported bimetallic hydrogenation catalyst”. There is no antecedent basis for this, since claim 16 has been rewritten as an independent claim. The examiner recommends that “the unsupported bimetallic hydrogenation catalyst” be amended to “an unsupported bimetallic hydrogenation catalyst”.
Claim Rejections - 35 USC § 102
Claims 1-6, 12-15, and 20-21 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Zhou (U.S. PG Pub. No. 2007/0158236).
In paragraph 25 Zhou discloses bimetallic catalyst precursors including a plurality of molybdenum atoms and a plurality of atoms of a secondary transition metal such as cobalt. Molybdenum is a Group VIB metal, meeting the limitations of M1 and M2 metals of claim 1 and 4, and cobalt is a Group VIII metal, also meeting the limitations of M1 and M2 of claims 1 and 4. In paragraph 33 Zhou discloses that the secondary transition metal can be other metals meeting the limitations of the M1 and M2 metals of claims 1 and 4. In paragraph 30 Zhou discloses that the catalyst precursors are manufactured by reacting the metals with a plurality of organic agent molecules, and in paragraphs 36-37 Zhou discloses that the organic agent molecules can be various carboxylic acids, leading to the formation of organic ligands meeting the limitations of the R(COO)x ligands of claim 1 where x is 1, as well as meeting the limitations of the organic carboxylic acids of claim 5. In paragraph 34 Zhou discloses that the secondary transition metal can be divalent, and in paragraphs 41 and 57-58 teaches that the molybdenum can be reduced to an average oxidation of between 3 and 4, leading to bimetallic catalyst precursors where the value of b is between 2 and 4 depending on the ratio of molybdenum to secondary transition metal, within the range recited in claim 1. Zhou teaches that the reduction of the molybdenum also reduced the number of molybdenum oxides present in the product, indicating that the value of a falls within the range recited in claim 1. The bimetallic catalyst precursor of Zhou therefore meets the compositional limitations of claims 1 and 4-5 and will therefore possess the IR peaks recited in claims 1 and 3. While Zhou refers to the compound as a “catalyst precursor”, it meets the compositional and structural limitations of the claimed catalyst. Claims 1 and 3-5 are therefore anticipated by Zhou.
In examples 3-9 (paragraphs 79-98) Zhou discloses the preparation of catalyst precursors having metal contents within the range recited in claim 6. Zhou discloses in these examples and in paragraphs 43-47 that the catalyst precursors can be prepared by first reacting a molybdenum source with a carboxylic acid, and then adding the secondary transition metal to the reaction mixture along with additional acid, which will result in at least some of a bimetallic catalyst precursor product having the structure recited in claim 2, rather than just a mixture of metal salts.
In paragraphs 61-65 Zhou discloses that the bimetallic catalyst precursor can be mixed with a hydrocarbon diluent. Hydrocarbons must be aliphatic or aromatic and therefore meet the limitations of either the aliphatic or aromatic hydrocarbons of the organic solvent of claim 12. Additionally, Zhou discloses in examples 3-9 methods of preparing the bimetallic catalyst precursor where a stoichiometric excess of 2-ethylhexanoic acid is reacted with a divalent metal oxide, which will lead to products where some free acid is still present, meeting the limitations of the organic ligand of claim 12 and having peaks in the ranges recited in claim 13 since the bimetallic catalyst precursor of Zhou meets the structural limitations of the claimed catalyst composition. In Example 3 (paragraphs 79-80), 0.91 g of cobalt(II) hydroxide (0.0098 mol) is reacted with 5.4 g of 2-ethylhexanoic acid (0.037 mol); if the formation of cobalt(II) 2-ethylhexanoic acid is assumed to proceed to completion, about 2.6 g of ethylhexanoic acid will be left over, out of a total of 21.31 g of materials charged in the reaction mixture of paragraph 80 (15.0 g molybdenum 2-ethylhexanoate is included in addition to the cobalt(II) hydroxide and 2-ethylhexanoic acid), for an organic ligand percentage of about 12%, within the range recited in claim 14 and leading to a catalyst precursor concentration of about 88%, also within the range recited in claim 14.
In paragraph 13 Zhou discloses that the bimetallic catalyst precursor can form a catalyst in situ for use in hydrocracking heavy oil, and in paragraph 29 indicates that the heavy oil can include various residual oils and bottoms which are mixtures that comprise unsaturated hydrocarbon compounds, as recited in claim 15. While Zhou refers to the bimetallic compound as a catalyst precursor, Zhou discloses in examples 10-12 (paragraphs 99-101) that the catalyst precursor is brought into contact with the heavy oil, meeting the method limitation of claim 15, as well as the hydro-upgrading of heavy oils recited in claim 20. Zhou discloses in the examples that the reaction takes place under heating conditions in the presence of hydrogen, as recited in claim 21.
Claim Rejections - 35 USC § 103
Claims 7-11 and 22 are rejected under 35 U.S.C. 103 as being unpatentable over Zhou.
The discussion of Zhou in paragraph 10 above is incorporated here by reference. Zhou discloses a bimetallic catalyst precursor meeting the limitations of claim 1. In paragraphs 43-47 Zhou discloses that the bimetallic catalyst precursor is prepared by reacting molybdenum with an organic agent at an elevated temperature to produce a molybdenum salt, meeting the limitations of steps (1) and (2) of claim 7, and reacting a secondary transition metal with an organic agent at a second temperature. In paragraph 46 Zhou discloses that the temperature of the reaction mixture comprising the molybdenum salt can be adjusted to a temperature suitable for the reaction with the secondary transition metal before the secondary transition metal is added, in which case the period prior to the addition of the secondary transition metal meets the limitations of step (3) of claim 7 and adding the secondary transition metal meets the limitations of step (4) of claim 7. Collecting the product, as in examples 3-9 (paragraphs 79-98) meets the limitations of step (5) of claim 7. As discussed regarding claim 1 above, the molybdenum and secondary transition metal of Zhou meet the limitations of the first and second metal sources of claim 7, and the carboxylic acids used as the organic agent of Zhou meet the limitations of the organic ligand of claim 7.
In paragraphs 44-45 Zhou discloses that the reaction of the molybdenum compound and organic agent preferably takes place at a temperature of 100 to 350° C, overlapping the range recited for T1 of amended claim 7, and the reaction of the secondary transition metal and organic agent preferably takes place at 50 to 200° C, overlapping or falling within the range recited for T2 of amended claim 7. In paragraph 53 Zhou discloses that the molar ratio of molybdenum to the organic agent overlaps the range recited in claim 7, and in the examples, Zhou discloses examples where the molar ratio of organic agent to metal falls within the range recited in claim 7. For example, in Example 4 (paragraphs 81-83), Zhou discloses a method using 10.0 g molybdic acid (0.062 mol), 3.0 g cobalt hydroxide (0.032 mol), and 45.3 g 2-ethylhexanoic acid (0.314 mol), which leads to a molar ratio of organic agent to metal of about 3.34 (0.314 / 0.094).
The mixture obtained from the first reaction does not require any components other than the molybdenum source and the carboxylic acid, meeting the limitations of claim 8 where the mixture consists of the metal source and the organic ligand compound. In paragraphs 32-34 and the examples, Zhou discloses that the metal sources can be various classes of metal compounds recited in claim 9, such as metal chlorides, oxides, hydroxides, nitrates, and sulfates. In paragraph 48 Zhou discloses that the molar ratio between the molybdenum and the secondary transition metal can be in ranges encompassing or overlapping the range recited in claim 11.
In Examples 10-12 (paragraphs 99-101) Zhou discloses hydrocracking reactions carried out at a temperature of about 440° C (about 825° F), and a pressure of about 15.17 MPa (2200 psig), within the ranges recited in claim 22.
The differences between Zhou and the currently presented claims are:
i) Some of the ranges of Zhou overlap or encompass the claimed ranges rather than falling within them.
ii) Zhou does not specifically disclose the times t1 and t2 in steps (2) and (3) of claim 7 and the liquid hourly space velocity (LHSV) or the hydrogen-to-oil volume ratio of claim 22.
With respect to i), see MPEP 2144.05(I): “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);” "[A] prior art reference that discloses a range encompassing a somewhat narrower claimed range is sufficient to establish a prima facie case of obviousness." In re Peterson, 315 F.3d 1325, 1330, 65 USPQ2d 1379, 1382-83 (Fed. Cir. 2003).
With respect to ii), "[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). Additionally, case law holds that “discovery of an optimum value of a result effective variable in a known process is ordinarily within the skill of the art.” See In re Boesch, 617 F.2d 272, 205 USPQ 215 (CCPA 1980). In this case, one of ordinary skill in the art would understand the time periods for the reaction of molybdenum with the organic ligand of steps (2) and (3) of claim 7, and the LHSV and hydrogen-to-oil ratio of claim 22 would affect the functioning and outcome of the process of Zhou, and optimizing those parameters would be within the scope of ordinary skill in the art.
Claims 7-9, 11, and 22 are therefore rendered obvious by Zhou. Additionally, since claim 10 only limits claim 7 or the case where a dispersion of the metal source is used, claim 10 is also rendered obvious for the case where the metal source is not used as a dispersion.
Allowable Subject Matter
Claims 16-18 would be allowable if rewritten to overcome the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), 2nd paragraph, set forth in this Office action and to include all of the limitations of the base claim and any intervening claims.
Claim 16 and its dependent claims recite a composition comprising a hydrogenation catalyst, a dispersion medium, and an activator, where the activator is a sulfur-containing compound. Zhou, however, discloses that the catalyst precursor is activated in situ by the sulfur present in the heavy oil being hydrotreated, and one of ordinary skill in the art therefore would have no motivation to include the catalyst precursor of Zhou in a composition comprising a dispersion medium and an activator. It is noted that the inclusion of the catalyst precursor and diluent in a heavy oil, in accordance with Zhou, would not meet the claim limitations, since Zhou discloses in paragraph 65 that the catalyst precursor is present in the diluent in an amount far less than the lower bound of the claimed range (noting that the catalyst precursors of Zhou have a metal content of about 12 to 18% by weight), and the catalyst precursor concentration will be even lower once added to the heavy oil. The prior art does not disclose or render obvious an unsupported catalyst composition comprising a catalyst (or catalyst precursor) meeting the limitations of the claimed catalyst, a dispersion medium, and a sulfur-containing activator in the concentrations recited in claims 16-18.
Response to Arguments
Applicant's arguments filed 6/22/26 have been fully considered but they are not persuasive. Applicant argues that Zhou teaches away from the formation of molybdenum complexes, citing paragraphs 53-54 of Zhou. However, Zhou teaches that the formation of undesired molybdenum complexes is avoided. This is not a blanket teaching away from the formation of all molybdenum-containing complexes. As discussed in the rejection, Zhou teaches a molybdenum-containing bimetallic catalyst comprising an organic ligand and meeting the limitations of the structure of the claimed bimetallic hydrogenation catalyst. Zhou teaches in paragraph 25 that the transition metal atoms, including the molybdenum atoms, are bonded to the organic ligand, which indicates that the catalyst precursors of Zhou are organometallic complexes. Applicant’s arguments are therefore not persuasive.
Regarding claims 7-11 and 22, applicant also argues that Zhou does not disclose or suggest that steps 2 and 3 of the claimed method are carried out in sequence at different temperatures. However, as discussed in the rejection, the reaction mixture of step (2) can be adjusted to a higher temperature prior to the addition of the secondary transition metal, which is sufficient to meet the limitations of step (3). Additionally, while the claim now specifically requires that T1 and T2 be non-overlapping temperatures, the time at which the reaction mixture is held at each temperature is a matter of routine optimization. It is also noted that Zhou explicitly states in paragraph 45 that those skilled in the art would be able to select optimal reaction temperatures, further indicating that reaction conditions are a matter of optimization within the scope of ordinary skill in the art.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 JAMES C GOLOBOY whose telephone number is (571)272-2476. The examiner can normally be reached M-F, usually about 10:00-6:30.
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/JAMES C GOLOBOY/Primary Examiner, Art Unit 1771
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