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 .
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.
Claim Amendments
Applicant’s amendments to the claims filed 20 May 2026 have been entered and considered for this action. The prior rejections under 35 USC § 112(a) are withdrawn.
Claim Rejections - 35 USC § 103
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 and 3-5 are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (US 2004/0133056 A1) in view of Zhang et al. (US 2016/0199825 A1) and Wu et al. (CN 103801402 A). The previously provided English machine translation of Wu (CN 103801402 A) is used in the analysis below.
Regarding claim 1, Liu teaches a method of preparing a composite ionic liquid the method comprising (paragraphs 69-70):
adding an ammonium salt (triethylamine hydrochloride) into a reaction kettle under an inert gas atmosphere (under the protection of nitrogen; having the salt in the vessel means that it was added), adding a first metal salt (AlCl3 was slowly added), then raising the temperature to 80 °C and performing a reaction for 2 hours (followed by 2 h of stirring) to obtain a first mixture, wherein the ammonium salt is a hydrohalide of alkyl-containing amine (triethylamine hydrochloride) and the first metal salt is aluminum halide (AlCl3);
adding a second metal salt into the first mixture (CuCl was added) and obtaining a second mixture after the second metal salt dissolves completely in a reaction system (until the solids disappeared completely), wherein the second metal salt is a halide and the second metal is copper (CuCl).
The temperature and time of reaction taught by Liu for the first step both fall within the instantly claimed ranges of 80°-120°C and at least 2 hours, respectively.
Liu also teaches that composite ionic liquids which contain a third metal salt, wherein the third metal is a metal halide (two or more metal compounds…other metal compounds are halides, paragraph 21; and addition of CuCl and NiCl2, paragraph 72) can be produced with their method.
Liu further teaches the molar ratio of ammonium salt to the first metal salt being 1:2.0 (0.282 mol : 0.56 mol, paragraph 72), the molar ratio of the ammonium salt to the second metal salt being 1: 0.2 (0.282 mol: 0.056 mol CuCl, paragraph 72) and the molar ratio of ammonium chloride to the third metal salt being 1: 0.2 (0.282 mol: 0.056 mol NiCl2, paragraph 72).
Liu does not teach adding the first metal salt at a controlled temperature of 50°C-80°C, adding the second metal salt at a controlled temperature of 120°C-170°C, or adding a third metal salt into the second mixture at a controlled temperature of 120-1700C, wherein the third metal is a rare earth metal comprising one or more of lanthanum, cerium, neodymium, samarium and gadolinium.
However, Zhang teaches a nearly identical process for preparing composite ionic liquids (abstract and paragraphs 35 and 37), and that during the addition of metal salts the temperature should be controlled (reaction of the metal salts with the ammonium salt is fast and exothermic. The size of the portions of the metal salts is selected such that the temperature raise is controlled; paragraph 12), and that preferably the reaction temperature should be kept below 160 °C to avoid loss of aluminum chloride (paragraph 12). In one embodiment, Zhang teaches the reaction temperature during the addition of aluminum chloride being controlled in the range of 60°C-100°C (paragraph 35), while in another they teach the temperature being controlled to below 80 °C with no mention of a lower bound (paragraph 37).
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to add the first metal salt in the method of Liu at a controlled temperature below 80°C and above 60°C, as taught by Zhang. One of ordinary skill in the art would find this modification obvious as it represents the substitution of one known set of thermal conditions for another to yield predictable results. MPEP 2143(I)(B). Liu, as modified by Zhang, thus teaches adding a first metal salt at a controlled temperature of 60°C-80°C, which lies inside the instantly claimed range of 50°C-80°C.
Regarding the temperature at which addition of the second metal salt is performed, Zhang teaches that CuCl is added at 120 °C. Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention to add the second metal salt in the method of Liu at a controlled temperature 120°C, as taught by Zhang. Liu, as modified by Zhang, thus teaches adding a second metal salt at a controlled temperature of 120°C, which lies inside the instantly claimed range of 120°C-170°C.
Regarding adding a third metal salt to the second mixture at a controlled temperature of 120-170°C, while Liu teaches the addition of a third metal salt (NiCl2), they do so at the same time as adding the second metal salt and at 80°C (paragraph 72). However, Zhang teaches the addition of a third metal salt to the second mixture at a controlled temperature of 120 °C -150 °C (CuCl was added to the IL mixture…and [it was] kept at 120 °C …then, a third portion of AlCl3 was added [and] the temperature rose to 150°C; paragraph 35).
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention to add the third metal salt in the method of Liu to the second mixture at a controlled temperature of 120°C-150°C, as taught by Zhang. One of ordinary skill in the art would find this modification obvious as it represents the substitution of one known method to add a third metal for another to yield predictable results. MPEP 2143(I)(B). Liu, as modified by Zhang, thus teaches adding a third metal salt to the second mixture at a controlled temperature of 120°C-150°C, which lies inside the instantly claimed range of 120°C-170°C.
Regarding the limitation wherein the third metal is a rare earth metal, neither Liu nor Zhang teach this limitation. However, Wu teaches an ionic liquid composite catalyst that contains multiple metal halides, one of which is lanthanum (abstract and paragraph 26; lanthanum is a rare earth metal). Wu also teaches that adding lanthanum chloride to a composite ionic liquid catalyst significantly improves catalytic performance in an alkylation reaction (after adding lanthanum chloride during the preparation of the quaternary phosphonium salt ionic liquid composite catalyst, the yield of monobenzyltoluene and dibenzyltoluene can be significantly improved; [0118], lines 936-938).
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the invention, to replace one of the metal salts in the composite ionic liquids of Liu with lanthanum chloride, as taught by Wu. One of ordinary skill would have been motivated to do in order to increase catalytic performance.
Regarding claims 3-5, modified Liu teaches claim 1, as analyzed above, where Liu teaches the ammonium salt is triethylammonium chloride (paragraph 72), the first metal salt is aluminum chloride (paragraph 72), and the second metal salt is copper chloride (paragraph 72), which is a halide of copper, thereby meeting the limitations of claims 3-5.
Claim 7 is rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (US 2004/0133056 A1) in view of Zhang et al. (US 2016/0199825 A1), and Wu et al. (CN 103801402 A), as applied to claim 1 above, and further in view of van Broekhoven et al. (US 2020/0002624 A1). The previously provided English machine translation of Wu (CN 103801402 A) is used in the analysis below.
Regarding claim 7, modified Liu teaches the method of claim 1, as analyzed above, but none of Liu, Zhang, nor Wu teach the third metal salt comprising at least two rare earth metals.
However, Broekhoven teaches an alkylation process that comprises rare earth-element acid catalysts (paragraphs 1 and 27), like that of the instant application and of modified Liu. This work is therefore in a related field of endeavor, as further evidenced by Broekhoven describing ionic liquid catalysts in their specification (paragraph 8).
Broekhoven also teaches that preferred embodiments of their invention include those in which cerium comprises at least 10% of the rare earth elements present (paragraph 28), which corresponds to a molar ratio of greater than 0.1:1, and implies the presence of multiple rare earth metals, thereby meeting the claim limitation wherein the molar ratio of one rare earth element to the remaining rare-earth elements is in the range (0.05-50):1.
Therefore, it would have been obvious to one of ordinary in the skill in the art, before the effective filing date of the claimed invention, to use in the method of modified Liu a third metal comprising at least two rare earth metals, a molar ratio of any one rare earth metal to the remaining rare earth metals being greater than 0.1:1, as taught by Broekhoven. One of ordinary skill in the art would have been motivated to do so because they would be substituting the multiple rare earth system and ratios used Broekhoven for the single rare earth system taught by Wu to obtain predictable results. MPEP 2143(I)(B). Alternatively, one would have been motivated to use the mixture of Broekhoven because Broekhoven teaches that their catalysts give products with improved octane numbers and value (title and abstract).
It is noted that the courts have stated where the claimed ranges “overlap or lie inside the ranges disclosed by the prior art” a prima facie case of obviousness exists (see 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); Titanium Metals Corp. of America v. Banner, 778 F2d 775. 227 USPQ 773 (Fed. Cir. 1985) (see MPEP 2144.05.01). Therefore, because the ratio of ranges taught by modified Liu overlaps with the instantly claimed range of 0.05-50:1, the limitations of claim 7 are obvious.
Response to Arguments
Applicant's arguments filed 20 May 2026 have been fully considered but they are not persuasive.
Applicants arguments, page 5, try to distinguish between the multi-coordinated metal center anion formed by the instant method and the system described by Zhang. However, it is noted that Zhang describes the formation of the same multi-coordinated metal center anions: “Due to the high acidity of the aluminium Lewis acid the aluminium chloride… is combined with a second or more metal halide … to form a coordinate anion, in particular a coordinate anion derived from two or more metal halides, wherein at least one metal halide is an aluminium halide ([0008], emphasis added).
Applicant’s further arguments regarding the finding of Liu that the third metal provide no significant difference in yield and conversion using the ionic liquid catalysts is noted, but the conclusion that one of ordinary skill would not consider modifying the third metal in order to optimize yield or conversion based upon this one experiment is not justified. In particular, combined with Wu’s teaching on the effects of introducing rare-earth metals, one of ordinary skill would have motivation to vary the metals in the systems of Liu and Zhang, including varying of the third metal to be a rare earth metal.
Applicant’s arguments regarding the incorporation of teachings from Wu and Broekhoven into the method of modified Liu, page 7, have also been considered but are not persuasive. In particular, while the systems of Wu and Broekhoven are not the same as that of Liu and Zhang, they are all dealing with the same problem of improving activity of Lewis acid catalysts in alkylation reactions.
Wu is used only to teach that lanthanum can improve activity of ionic liquid alkylation catalysts and others working in the field of chloroaluminate ionic liquid alkylation catalysts have cited the work of Wu as relevant to their endeavors (e.g., see CN 109721462 A).
Broekhoven is used only to teach that multiple rare earth metals can be used in place of single rare earth metal with positive effect on acid alkylation catalysts, these compositions being designated as “more preferable” ([0027]-[0028]). While the system of Broekhoven also includes hydrogenation metals, the Lewis acids of the zeolite are integral to the alkylation catalysts and are not merely structural, as implied by the arguments on p. 7 (¶ 3).
Through Broekhoven and Wu are used in the rejections set forth above for teaching the inclusion of rare earth elements in the composite ionic liquid, it is noted that such a teaching is also provided by Buchbinder et al. (WO 2016/161202 A1), where it is taught that the halometallate anions of ionic liquid catalysts may include composite halometallate anions where the metals are selected from a group that includes aluminum, lanthanum and cerium (p. 18, lines 1-5).
It is further noted that Liu teaches molar ratios for the components of the composite ionic liquid that fall within the claimed ranges, as analyzed above, so any argument relying on molar ratios being missing from the prior art are also not persuasive.
The arguments with respect to Xing are considered moot because Xing is not relied upon in the rejections of the amended claims.
Therefore, the rejections of all claims are maintained.
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.
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/NICHOLAS A. PIRO/Assistant Examiner, Art Unit 1738
/PAUL A WARTALOWICZ/Primary Examiner, Art Unit 1735
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