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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 December 01, 2025 has been entered.
Status of the Claims
Claims 1, 5-10, 12, 14-17, 20-23, and 25-27 are pending in this application. Claims 2-4, 11, 13, 18-19, 24, and 28 have been cancelled by Applicant. Claims 15-17, 20-23, and 25-27 are withdrawn from consideration. Claims 1, 5-10, 12, and 14 are under examination herein.
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.
Claims 1, 5-10, 12, and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Nockemann et al. (WO 2018/109483 A1 – cited in IDS - previously cited) (“Nockemann”); in view of Rebeiro et al. (Org. Process Res. Dev. 2002, 6, 826-828 – previously cited) (“Rebeiro”).
Regarding claim 1, Nockemann discloses Example 1 below, which reads on the instant claims when: Z is imidazole; L1 is C3 alkanediyl; L1 is C1 alkanediyl; EDG is -C(O)NRyRz, wherein Ry and Rz are isobutyl (reading on alkyl), and LG is Cl.
Example 1
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While Nockemann’s discloses their process of reactant (1) + reactant (2) in NEt3 and CHCl3 at 60-70 °C for 7 days a three-necked round bottom flask (as opposed to a sealed reactor at 100-180 °C, as claimed); the teachings of Rebeiro are relied upon for these disclosures.
Rebeiro discloses a related reaction with a chloride leaving group (see Scheme 1) to afford alkyl pyridinium salt. Rebeiro teaches “drawbacks” to using an “open vessel” and benefits of using a sealed reactor under microwave for synthesizing ionic liquids such as alkyl imidazolium salts. Some drawbacks include long reaction times, increased exposure to hazardous conditions and wasted reactants through evaporation (col. 1 and 2 page 826). Rebeiro teaches that reactions which would normally not proceed in an open container resulted in excellent yields under their reaction conditions (para. Linking pages 826-827; and Table 1).
Therefore, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the instant application to prepare an ionic liquid (IL) composition comprising the compound [cat]+[LG]- in view of Nockemann and Rebeiro by reacting a compound (1) with a compound (2) in a sealed reactor at a temperature ranging from 100-180 °C. One of ordinary skill would have been motivated to do so because Nockemann discloses their method of Example 1 above, for the preparation of compound [MAIL]+Cl-, which had extremely long reaction times of 7 days; further because Rebeiro teaches their method of making an ionic liquid in a sealed container at temperatures ranging from 85-230 °C (see Table 1), to give excellent yields of their ionic compounds. One of ordinary skill would have had a reasonable expectation of success in view of Nockemann’s disclosure of their compounds; and Rebeiro’s guidance that their sealed reaction conditions gave “excellent yield of the product” and “drastically” reduced reaction times “from 72 to 1 h and from 22 h to 24 min in case of 1-butylpyridinium and 1-butyl-3-methylimidazolium chlorides, respectively”. See p. 827 left column.
Regarding the claimed temperature range of 100-180 °C; Rebeiro’s disclosure of their 85-230 °C range reads on the instant claim. Applicant is advised that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, 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). The courts have also found that where 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. See In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). See MPEP 2144.05-II. Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Regarding claim 5, Rebeiro teaches that reactions in open vessels that ordinarily take several hours to several days can be “drastically” reduced. Since Nockemann teaches the elected process takes 7 days at 60-70 °C, a PHOSITA would have reasonably expected that by employing Rebeiro’s microwave conditions the reaction time for the elected process would be “drastically” reduced. Since Rebeiro teaches 1-butyl-3-methylimidazolium chloride is produced in 24 min at 85-150 °C (Table 1), a PHOSITA would have been motivated to optimize the reaction time to fall within the claimed range of 0.5-24 hours.
Regarding claims 6-7, Nockemann uses 3.0 equivalents (0.15 mol) of N,N-diisobutyl-2-chloroacetamide (instant Reactant (2)) relative to the imidazole (0.05 mol, Reactant (1)) in example 1 (3.0 equivalents), which falls within the claimed range.
Regarding claims 8-10, Nockemann adds 0.11 moles of triethylamine (a nitrogen containing base) prior to heating the reaction (2.2 molar equivalents (0.11 mol /0.05 mol) of base).
Regarding claims 12 and 14, Nockemann adding chloroform prior to heating the reaction meets the claimed requirement of adding an organic solvent (claim 12), such as chloroform (claim 14).
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.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1, 5-10, 12, and 14 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 69, 83 and 88 of copending Application No. 17/872,533 (Copending ‘533); and Nockemann et al. (WO 2018/109483 A1 – cited in IDS - previously cited) (“Nockemann”); in view of Rebeiro et al. (Org. Process Res. Dev. 2002, 6, 826-828 – previously cited) (“Rebeiro”).
Regarding instant claim 1, 5-10, 12, and 14, Copending ‘533 claims a method for preparing an ionic liquid of the formula (I) below, wherein [Y]+ can be [Z]+-L2-EDG to make an IL of Formula (II) below (Copending ‘533’s claims 69, 83, and 88) – same IL as the instant invention – their method comprising reacting
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While Copending ‘533 doesn’t specifically claim their method wherein the reaction is done in a sealed vessel, with an organic solvent, at a temperature of 100-180 °C; the teachings of Nockemann and Rebeiro are relied upon for these disclosures.
Nockemann discloses their related reaction of Example 1 shown above, performed at 60-70 °C in an open flask, and allowed to stir for 7 days.
Rebeiro discloses a related reaction with a chloride leaving group (see Scheme 1) to afford alkyl pyridinium salt. Rebeiro teaches “drawbacks” to using an “open vessel” and benefits of using a sealed reactor under microwave for synthesizing ionic liquids such as alkyl imidazolium salts. Some drawbacks include long reaction times, increased exposure to hazardous conditions and wasted reactants through evaporation (col. 1 and 2 page 826). Rebeiro teaches that reactions which would normally not proceed in an open container resulted in excellent yields under their reaction conditions (para. Linking pages 826-827; and Table 1).
Therefore, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the instant application to prepare the instant ionic liquid (IL) composition comprising the compound [cat]+[LG]- in view of Copending ‘533’s and Nockemann’s related reactions, in view of Rebeiro, by reacting a compound (1) with a compound (2) in a sealed reactor at a temperature ranging from 100-180 °C. One of ordinary skill would have been motivated to do so because Copending ‘533 discloses their related method of making the instant IL compounds; Nockemann discloses their method of Example 1 above, for the preparation of compound [MAIL]+Cl-, which had extremely long reaction times of 7 days; further because Rebeiro teaches their method of making an ionic liquid in a sealed container at temperatures ranging from 85-230 °C (see Table 1), to give excellent yields of their ionic compounds. One of ordinary skill would have had a reasonable expectation of success in view of Nockemann’s disclosure of their compounds; and Rebeiro’s guidance that their sealed reaction conditions gave “excellent yield of the product” and “drastically” reduced reaction times “from 72 to 1 h and from 22 h to 24 min in case of 1-butylpyridinium and 1-butyl-3-methylimidazolium chlorides, respectively”. See p. 827 left column.
Regarding the claimed temperature range of 100-180 °C; Rebeiro’s disclosure of their 85-230 °C range reads on the instant claim. Applicant is reminded that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. The courts have also found that where 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. Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Regarding claim 5, Rebeiro teaches that reactions in open vessels that ordinarily take several hours to several days can be “drastically” reduced. Since Nockemann teaches the elected process takes 7 days at 60-70 °C, a PHOSITA would have reasonably expected that by employing Rebeiro’s microwave conditions the reaction time for the elected process would be “drastically” reduced. Since Rebeiro teaches 1-butyl-3-methylimidazolium chloride is produced in 24 min at 85-150 °C (Table 1), a PHOSITA would have been motivated to optimize the reaction time to fall within the claimed range of 0.5-24 hours.
Regarding claims 6-7, Nockemann uses 3.0 equivalents (0.15 mol) of N,N-diisobutyl-2-chloroacetamide (instant Reactant (2)) relative to the imidazole (0.05 mol, Reactant (1)) in example 1 (3.0 equivalents), which falls within the claimed range.
Regarding claims 8-10, Nockemann adds 0.11 moles of triethylamine (a nitrogen containing base) prior to heating the reaction (2.2 molar equivalents (0.11 mol /0.05 mol) of base).
Regarding claims 12 and 14, Nockemann adding chloroform prior to heating the reaction meets the claimed requirement of adding an organic solvent (claim 12), such as chloroform (claim 14).
This is a provisional nonstatutory double patenting rejection.
Claims 1, 5-10, 12, and 14 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1, 14, and 20 of U.S. Patent No. 11,958,754 B2 (US ‘754); and Nockemann et al. (WO 2018/109483 A1 – cited in IDS - previously cited) (“Nockemann”); in view of Rebeiro et al. (Org. Process Res. Dev. 2002, 6, 826-828 – previously cited) (“Rebeiro”).
Regarding instant claim 1, 5-10, 12, and 14, US ‘754 claims a method for preparing an ionic liquid of the formula (I) below, wherein [Y]+ can be [Z]+-L2-EDG to make an IL of Formula (II) below (US ‘754’s claims 1, 14, and 20) – same IL as the instant invention – their method comprising reacting
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While US ‘754 doesn’t specifically claim their method wherein the reaction is done in a sealed vessel, with an organic solvent, at a temperature of 100-180 °C; the teachings of Nockemann and Rebeiro are relied upon for these disclosures.
Nockemann discloses their related reaction of Example 1 shown above, performed at 60-70 °C in an open flask, and allowed to stir for 7 days.
Rebeiro discloses a related reaction with a chloride leaving group (see Scheme 1) to afford alkyl pyridinium salt. Rebeiro teaches “drawbacks” to using an “open vessel” and benefits of using a sealed reactor under microwave for synthesizing ionic liquids such as alkyl imidazolium salts. Some drawbacks include long reaction times, increased exposure to hazardous conditions and wasted reactants through evaporation (col. 1 and 2 page 826). Rebeiro teaches that reactions which would normally not proceed in an open container resulted in excellent yields under their reaction conditions (para. Linking pages 826-827; and Table 1).
Therefore, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the instant application to prepare the instant ionic liquid (IL) composition comprising the compound [cat]+[LG]- in view of US ‘754’s and Nockemann’s related reactions, in view of Rebeiro, by reacting a compound (1) with a compound (2) in a sealed reactor at a temperature ranging from 100-180 °C. One of ordinary skill would have been motivated to do so because US ‘754 discloses their related method of making the instant IL compounds; Nockemann discloses their method of Example 1 above, for the preparation of compound [MAIL]+Cl-, which had extremely long reaction times of 7 days; further because Rebeiro teaches their method of making an ionic liquid in a sealed container at temperatures ranging from 85-230 °C (see Table 1), to give excellent yields of their ionic compounds. One of ordinary skill would have had a reasonable expectation of success in view of Nockemann’s disclosure of their compounds; and Rebeiro’s guidance that their sealed reaction conditions gave “excellent yield of the product” and “drastically” reduced reaction times “from 72 to 1 h and from 22 h to 24 min in case of 1-butylpyridinium and 1-butyl-3-methylimidazolium chlorides, respectively”. See p. 827 left column.
Regarding the claimed temperature range of 100-180 °C; Rebeiro’s disclosure of their 85-230 °C range reads on the instant claim. Applicant is reminded that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. The courts have also found that where 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. Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Regarding claim 5, Rebeiro teaches that reactions in open vessels that ordinarily take several hours to several days can be “drastically” reduced. Since Nockemann teaches the elected process takes 7 days at 60-70 °C, a PHOSITA would have reasonably expected that by employing Rebeiro’s microwave conditions the reaction time for the elected process would be “drastically” reduced. Since Rebeiro teaches 1-butyl-3-methylimidazolium chloride is produced in 24 min at 85-150 °C (Table 1), a PHOSITA would have been motivated to optimize the reaction time to fall within the claimed range of 0.5-24 hours.
Regarding claims 6-7, Nockemann uses 3.0 equivalents (0.15 mol) of N,N-diisobutyl-2-chloroacetamide (instant Reactant (2)) relative to the imidazole (0.05 mol, Reactant (1)) in example 1 (3.0 equivalents), which falls within the claimed range.
Regarding claims 8-10, Nockemann adds 0.11 moles of triethylamine (a nitrogen containing base) prior to heating the reaction (2.2 molar equivalents (0.11 mol /0.05 mol) of base).
Regarding claims 12 and 14, Nockemann adding chloroform prior to heating the reaction meets the claimed requirement of adding an organic solvent (claim 12), such as chloroform (claim 14).
Claims 1, 5-10, 12, and 14 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 19 of U.S. Patent No. 11,396,684 B2 (US ‘684); and Nockemann et al. (WO 2018/109483 A1 – cited in IDS - previously cited) (“Nockemann”); in view of Rebeiro et al. (Org. Process Res. Dev. 2002, 6, 826-828 – previously cited) (“Rebeiro”).
Regarding instant claim 1, 5-10, 12, and 14, US ‘684 claims a method for extracting rare earth metals comprising ionic liquids of formula (I) below, wherein [Y]+ can be [Z]+-L2-EDG to make an IL of Formula (II) below (US ‘684’s claims 1 and 19) – same IL as the instant invention.
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While US ‘684 doesn’t specifically claim a method for making these ILs, wherein the reaction is done in a sealed vessel, with an organic solvent, at a temperature of 100-180 °C; the teachings of Nockemann and Rebeiro are relied upon for these disclosures.
Nockemann discloses their related reaction of Example 1 shown above, performed at 60-70 °C in an open flask, and allowed to stir for 7 days.
Rebeiro discloses a related reaction with a chloride leaving group (see Scheme 1) to afford alkyl pyridinium salt. Rebeiro teaches “drawbacks” to using an “open vessel” and benefits of using a sealed reactor under microwave for synthesizing ionic liquids such as alkyl imidazolium salts. Some drawbacks include long reaction times, increased exposure to hazardous conditions and wasted reactants through evaporation (col. 1 and 2 page 826). Rebeiro teaches that reactions which would normally not proceed in an open container resulted in excellent yields under their reaction conditions (para. Linking pages 826-827; and Table 1).
Therefore, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the instant application to prepare the instant ionic liquid (IL) composition comprising the compound [cat]+[LG]- in view of US ‘684’s disclosure of the instant ILs, Nockemann’s reaction for making the instant ILs, and Rebeiro teachings for improving the reaction. One of ordinary skill would have been motivated to do so because US ‘684 discloses the instant ILs as useful in methods for extracting rare earth metals; Nockemann discloses their method of Example 1 above, for the preparation of IL compound [MAIL]+Cl-, which had extremely long reaction times of 7 days; further because Rebeiro teaches their improved method of making an ionic liquid in a sealed container at temperatures ranging from 85-230 °C (see Table 1), to give excellent yields of their ionic compounds. One of ordinary skill would have had a reasonable expectation of success in view of Nockemann’s disclosure of their compounds; and Rebeiro’s guidance that their sealed reaction conditions gave “excellent yield of the product” and “drastically” reduced reaction times “from 72 to 1 h and from 22 h to 24 min in case of 1-butylpyridinium and 1-butyl-3-methylimidazolium chlorides, respectively”. See p. 827 left column.
Regarding the claimed temperature range of 100-180 °C; Rebeiro’s disclosure of their 85-230 °C range reads on the instant claim. Applicant is reminded that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. The courts have also found that where 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. Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Regarding claim 5, Rebeiro teaches that reactions in open vessels that ordinarily take several hours to several days can be “drastically” reduced. Since Nockemann teaches the elected process takes 7 days at 60-70 °C, a PHOSITA would have reasonably expected that by employing Rebeiro’s microwave conditions the reaction time for the elected process would be “drastically” reduced. Since Rebeiro teaches 1-butyl-3-methylimidazolium chloride is produced in 24 min at 85-150 °C (Table 1), a PHOSITA would have been motivated to optimize the reaction time to fall within the claimed range of 0.5-24 hours.
Regarding claims 6-7, Nockemann uses 3.0 equivalents (0.15 mol) of N,N-diisobutyl-2-chloroacetamide (instant Reactant (2)) relative to the imidazole (0.05 mol, Reactant (1)) in example 1 (3.0 equivalents), which falls within the claimed range.
Regarding claims 8-10, Nockemann adds 0.11 moles of triethylamine (a nitrogen containing base) prior to heating the reaction (2.2 molar equivalents (0.11 mol /0.05 mol) of base).
Regarding claims 12 and 14, Nockemann adding chloroform prior to heating the reaction meets the claimed requirement of adding an organic solvent (claim 12), such as chloroform (claim 14).
Claims 1, 5-10, 12, and 14 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 16 of U.S. Patent No. 11,401,579 B2 (US ‘579); and Nockemann et al. (WO 2018/109483 A1 – cited in IDS - previously cited) (“Nockemann”); in view of Rebeiro et al. (Org. Process Res. Dev. 2002, 6, 826-828 – previously cited) (“Rebeiro”).
Regarding instant claim 1, 5-10, 12, and 14, US ‘579 claims a method for preparing a rare earth metal oxide comprising ionic liquids of formula (I) below, wherein [Y]+ can be [Z]+-L2-EDG to make an IL of Formula (II) below (US ‘579’s claims 1 and 16) – same IL as the instant invention.
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While US ‘579 doesn’t specifically claim a method for making these ILs, wherein the reaction is done in a sealed vessel, with an organic solvent, at a temperature of 100-180 °C; the teachings of Nockemann and Rebeiro are relied upon for these disclosures.
Nockemann discloses their related reaction of Example 1 shown above, performed at 60-70 °C in an open flask, and allowed to stir for 7 days.
Rebeiro discloses a related reaction with a chloride leaving group (see Scheme 1) to afford alkyl pyridinium salt. Rebeiro teaches “drawbacks” to using an “open vessel” and benefits of using a sealed reactor under microwave for synthesizing ionic liquids such as alkyl imidazolium salts. Some drawbacks include long reaction times, increased exposure to hazardous conditions and wasted reactants through evaporation (col. 1 and 2 page 826). Rebeiro teaches that reactions which would normally not proceed in an open container resulted in excellent yields under their reaction conditions (para. Linking pages 826-827; and Table 1).
Therefore, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the instant application to prepare the instant ionic liquid (IL) composition comprising the compound [cat]+[LG]- in view of US ‘579’s disclosure of the instant ILs, Nockemann’s reaction for making the instant ILs, and Rebeiro teachings for improving the reaction. One of ordinary skill would have been motivated to do so because US ‘579 discloses the instant ILs as useful in methods for extracting rare earth metals; Nockemann discloses their method of Example 1 above, for the preparation of IL compound [MAIL]+Cl-, which had extremely long reaction times of 7 days; further because Rebeiro teaches their improved method of making an ionic liquid in a sealed container at temperatures ranging from 85-230 °C (see Table 1), to give excellent yields of their ionic compounds. One of ordinary skill would have had a reasonable expectation of success in view of Nockemann’s disclosure of their compounds; and Rebeiro’s guidance that their sealed reaction conditions gave “excellent yield of the product” and “drastically” reduced reaction times “from 72 to 1 h and from 22 h to 24 min in case of 1-butylpyridinium and 1-butyl-3-methylimidazolium chlorides, respectively”. See p. 827 left column.
Regarding the claimed temperature range of 100-180 °C; Rebeiro’s disclosure of their 85-230 °C range reads on the instant claim. Applicant is reminded that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. The courts have also found that where 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. Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Regarding claim 5, Rebeiro teaches that reactions in open vessels that ordinarily take several hours to several days can be “drastically” reduced. Since Nockemann teaches the elected process takes 7 days at 60-70 °C, a PHOSITA would have reasonably expected that by employing Rebeiro’s microwave conditions the reaction time for the elected process would be “drastically” reduced. Since Rebeiro teaches 1-butyl-3-methylimidazolium chloride is produced in 24 min at 85-150 °C (Table 1), a PHOSITA would have been motivated to optimize the reaction time to fall within the claimed range of 0.5-24 hours.
Regarding claims 6-7, Nockemann uses 3.0 equivalents (0.15 mol) of N,N-diisobutyl-2-chloroacetamide (instant Reactant (2)) relative to the imidazole (0.05 mol, Reactant (1)) in example 1 (3.0 equivalents), which falls within the claimed range.
Regarding claims 8-10, Nockemann adds 0.11 moles of triethylamine (a nitrogen containing base) prior to heating the reaction (2.2 molar equivalents (0.11 mol /0.05 mol) of base).
Regarding claims 12 and 14, Nockemann adding chloroform prior to heating the reaction meets the claimed requirement of adding an organic solvent (claim 12), such as chloroform (claim 14).
Claims 1, 5-10, 12, and 14 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 20 of U.S. Patent No. 12,024,756 B2 (US ‘756); and Nockemann et al. (WO 2018/109483 A1 – cited in IDS - previously cited) (“Nockemann”); in view of Rebeiro et al. (Org. Process Res. Dev. 2002, 6, 826-828 – previously cited) (“Rebeiro”).
Regarding instant claim 1, 5-10, 12, and 14, US ‘756 claims a method for extracting rare earth metals comprising ionic liquids of formula (I) below, wherein [Y]+ can be [Z]+-L2-EDG to make an IL of Formula (II) below (US ‘756’s claims 1 and 20) – same IL as the instant invention.
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While US ‘756 doesn’t specifically claim a method for making these ILs, wherein the reaction is done in a sealed vessel, with an organic solvent, at a temperature of 100-180 °C; the teachings of Nockemann and Rebeiro are relied upon for these disclosures.
Nockemann discloses their related reaction of Example 1 shown above, performed at 60-70 °C in an open flask, and allowed to stir for 7 days.
Rebeiro discloses a related reaction with a chloride leaving group (see Scheme 1) to afford alkyl pyridinium salt. Rebeiro teaches “drawbacks” to using an “open vessel” and benefits of using a sealed reactor under microwave for synthesizing ionic liquids such as alkyl imidazolium salts. Some drawbacks include long reaction times, increased exposure to hazardous conditions and wasted reactants through evaporation (col. 1 and 2 page 826). Rebeiro teaches that reactions which would normally not proceed in an open container resulted in excellent yields under their reaction conditions (para. Linking pages 826-827; and Table 1).
Therefore, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the instant application to prepare the instant ionic liquid (IL) composition comprising the compound [cat]+[LG]- in view of US ‘756’s disclosure of the instant ILs, Nockemann’s reaction for making the instant ILs, and Rebeiro teachings for improving the reaction. One of ordinary skill would have been motivated to do so because US ‘756 discloses the instant ILs as useful in methods for extracting rare earth metals; Nockemann discloses their method of Example 1 above, for the preparation of IL compound [MAIL]+Cl-, which had extremely long reaction times of 7 days; further because Rebeiro teaches their improved method of making an ionic liquid in a sealed container at temperatures ranging from 85-230 °C (see Table 1), to give excellent yields of their ionic compounds. One of ordinary skill would have had a reasonable expectation of success in view of Nockemann’s disclosure of their compounds; and Rebeiro’s guidance that their sealed reaction conditions gave “excellent yield of the product” and “drastically” reduced reaction times “from 72 to 1 h and from 22 h to 24 min in case of 1-butylpyridinium and 1-butyl-3-methylimidazolium chlorides, respectively”. See p. 827 left column.
Regarding the claimed temperature range of 100-180 °C; Rebeiro’s disclosure of their 85-230 °C range reads on the instant claim. Applicant is reminded that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. The courts have also found that where 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. Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
Regarding claim 5, Rebeiro teaches that reactions in open vessels that ordinarily take several hours to several days can be “drastically” reduced. Since Nockemann teaches the elected process takes 7 days at 60-70 °C, a PHOSITA would have reasonably expected that by employing Rebeiro’s microwave conditions the reaction time for the elected process would be “drastically” reduced. Since Rebeiro teaches 1-butyl-3-methylimidazolium chloride is produced in 24 min at 85-150 °C (Table 1), a PHOSITA would have been motivated to optimize the reaction time to fall within the claimed range of 0.5-24 hours.
Regarding claims 6-7, Nockemann uses 3.0 equivalents (0.15 mol) of N,N-diisobutyl-2-chloroacetamide (instant Reactant (2)) relative to the imidazole (0.05 mol, Reactant (1)) in example 1 (3.0 equivalents), which falls within the claimed range.
Regarding claims 8-10, Nockemann adds 0.11 moles of triethylamine (a nitrogen containing base) prior to heating the reaction (2.2 molar equivalents (0.11 mol /0.05 mol) of base).
Regarding claims 12 and 14, Nockemann adding chloroform prior to heating the reaction meets the claimed requirement of adding an organic solvent (claim 12), such as chloroform (claim 14).
Response to Arguments
Claims
Claim amendments are acknowledged and have been entered. No new matter has been introduced.
Improper Markush Grouping Rejection
In view of claim amendments, this Improper Markush Grouping Rejection has been withdrawn.
Claim Rejections - 35 USC § 103
Applicant's arguments filed 12/01/2025 have been fully considered but they are not persuasive.
Applicant argues that Rebeiro fails to teach the features not disclosed by Nockemann, and that there is no reasonable expectation of success. Applicant argues Rebeiro is directed toward the synthesis of an IL precursor with lower molecular weight and different physical properties compared to the instant bulky ILs, and that the mechanisms are significantly different. Applicant argues Rebeiro does not teach or suggest formation of tertiary amines, nor a mechanism for their formation.
In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
In response to applicant’s argument that there is no teaching, suggestion, or motivation to combine the references, the examiner recognizes that obviousness may be established by combining or modifying the teachings of the prior art to produce the claimed invention where there is some teaching, suggestion, or motivation to do so found either in the references themselves or in the knowledge generally available to one of ordinary skill in the art. See In re Fine, 837 F.2d 1071, 5 USPQ2d 1596 (Fed. Cir. 1988), In re Jones, 958 F.2d 347, 21 USPQ2d 1941 (Fed. Cir. 1992), and KSR International Co. v. Teleflex, Inc., 550 U.S. 398, 82 USPQ2d 1385 (2007).
In this case, Nockemann discloses their related reaction of Example 1 shown above, performed at 60-70 °C in an open flask, and allowed to stir for 7 days.
Rebeiro discloses a related reaction with a chloride leaving group (see Scheme 1) to afford alkyl pyridinium salt. Rebeiro teaches “drawbacks” to using an “open vessel” and benefits of using a sealed reactor under microwave for synthesizing ionic liquids such as alkyl imidazolium salts. Some drawbacks include long reaction times, increased exposure to hazardous conditions and wasted reactants through evaporation (col. 1 and 2 page 826). Rebeiro teaches that reactions which would normally not proceed in an open container resulted in excellent yields under their reaction conditions (para. Linking pages 826-827; and Table 1).
Therefore, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the instant application to prepare an ionic liquid (IL) composition comprising the compound [cat]+[LG]- in view of Nockemann and Rebeiro by reacting a compound (1) with a compound (2) in a sealed reactor at a temperature ranging from 100-180 °C. One of ordinary skill would have been motivated to do so because Nockemann discloses their method of Example 1 above, for the preparation of compound [MAIL]+Cl-, which had extremely long reaction times of 7 days; further because Rebeiro teaches their method of making an ionic liquid in a sealed container at temperatures ranging from 85-230 °C (see Table 1), to give excellent yields of their ionic compounds. One of ordinary skill would have had a reasonable expectation of success in view of Nockemann’s disclosure of their compounds; and Rebeiro’s guidance that their sealed reaction conditions gave “excellent yield of the product” and “drastically” reduced reaction times “from 72 to 1 h and from 22 h to 24 min in case of 1-butylpyridinium and 1-butyl-3-methylimidazolium chlorides, respectively”. See p. 827 left column.
In response to Applciant’s arguments that Rebeiro is directed toward the synthesis of an IL precursor with lower molecular weight and different physical properties compared to the instant bulky ILs, and that the mechanisms are significantly different; or that Rebeiro does not teach or suggest formation of tertiary amines, nor a mechanism for their formation. Applicant is advised that, per MPEP 2141.03 (I): "A person of ordinary skill in the art is also a person of ordinary creativity, not an automaton." KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 421, 82 USPQ2d 1385, 1397 (2007). "[I]n many cases a person of ordinary skill will be able to fit the teachings of multiple patents together like pieces of a puzzle." Id. at 420, 82 USPQ2d 1397. Office personnel may also take into account "the inferences and creative steps that a person of ordinary skill in the art would employ." Id. at 418, 82 USPQ2d at 1396. Thus, one of ordinary skill would have been motivated to prepare Nockemann’s compounds using Rebeiro’s conditions, as outlined above, with a reasonable expectation of success. A person of ordinary skill has good reason to pursue known options within his or her technical grasp. Note: MPEP 2143(E) KSR,550 U.S. at 421, 82 USPQ2d at 1397.
Conclusion
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/JACKSON J HERNANDEZ/Examiner, Art Unit 1627
/SARAH PIHONAK/Primary Examiner, Art Unit 1627
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