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 .
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 Claims 15-17, 20-23, and 25-27 are withdrawn from consideration.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; L2 is C1 alkanediyl; EDG is -C(O)NRyRz, wherein Ry and Rz are isobutyl (reading on alkyl), and LG is Cl.
Example 1
PNG
media_image1.png
197
441
media_image1.png
Greyscale
PNG
media_image2.png
446
1356
media_image2.png
Greyscale
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 liquid precursors 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 precursors 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
PNG
media_image3.png
82
167
media_image3.png
Greyscale
.
PNG
media_image4.png
143
107
media_image4.png
Greyscale
(I)
PNG
media_image5.png
197
147
media_image5.png
Greyscale
(II)
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
PNG
media_image3.png
82
167
media_image3.png
Greyscale
.
PNG
media_image4.png
143
107
media_image4.png
Greyscale
(I)
PNG
media_image5.png
197
147
media_image5.png
Greyscale
(II)
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.
PNG
media_image4.png
143
107
media_image4.png
Greyscale
(I)
PNG
media_image5.png
197
147
media_image5.png
Greyscale
(II)
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.
PNG
media_image4.png
143
107
media_image4.png
Greyscale
(I)
PNG
media_image5.png
197
147
media_image5.png
Greyscale
(II)
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.
PNG
media_image4.png
143
107
media_image4.png
Greyscale
(I)
PNG
media_image5.png
197
147
media_image5.png
Greyscale
(II)
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
Claim Rejections - 35 USC § 103
Applicant's arguments filed 09/08/2026 have been fully considered but they are not persuasive.
As an initial matter, Applicant is advised that MPEP 716.01(c) makes clear that “[t]he arguments of counsel cannot take the place of evidence in the record” (In re Schulze, 346 F.2d 600, 602, 145 USPQ 716, 718 (CCPA 1965)).
Applicant alleges that Examiner conflates the terms “ionic liquid” and “ionic liquid precursor” and that Rebeiro does not seem to report “their methods for making ionic liquids” and states the reactions claimed are not the same as those in Rebeiro. Applicant asserts one of ordinary skill would not have been motivated to disregard reaction parameters of claim 1 and replace the with Rebeiro’s conditions. Applicant asserts temperature ranges of 100-180 °C is not obvious in view of Rebeiro’s 85-230 °C temperature range. Applicant asserts Examiner “picks and chooses” certain portions of Rebeiro to locate limitations of the instant claims and that such reliance of broad, generic disclosure is allegedly not permitted. Applicant asserts examiner uses hindsight reasoning to arrive at rejections. Applicant asserts there is no reasonable motivation or expectation of success to combine the art.
In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971).
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 Example 1 below, which reads on the instant claims when: Z is imidazole; L1 is C3 alkanediyl; L2 is C1 alkanediyl; EDG is -C(O)NRyRz, wherein Ry and Rz are isobutyl (reading on alkyl), and LG is Cl.
Example 1
PNG
media_image1.png
197
441
media_image1.png
Greyscale
PNG
media_image2.png
446
1356
media_image2.png
Greyscale
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 liquid precursors, 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 precursors 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.
In response to Applicant’s argument that Examiner picks and chooses teachings from a broad or generic disclosures, per MPEP 2123 (I): “A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill in the art, including nonpreferred embodiments. Merck & Co. v. Biocraft Labs., Inc. 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir. 1989), cert. denied, 493 U.S. 975 (1989).”
In response to Applicant’s assertion that there’s no expectation of success that Rebeiro’s conditions will work to make Nockmann’s ionic liquids, per MPEP 2143.02 (I): “Conclusive proof of efficacy is not required to show a reasonable expectation of success. OSI Pharm., LLC v. Apotex Inc., 939 F.3d 1375, 1385, 2019 USPQ2d 379681 (Fed. Cir. 2019) ("To be clear, we do not hold today that efficacy data is always required for a reasonable expectation of success. Nor are we requiring ‘absolute predictability of success.’"); Acorda Therapeutics, Inc. v. Roxane Lab., Inc., 903 F.3d 1310, 1333, 128 USPQ2d 1001, 1018 (Fed. Cir. 2018) ("This court has long rejected a requirement of ‘[c]onclusive proof of efficacy’ for obviousness." (citing to Hoffmann-La Roche Inc. v. Apotex Inc., 748 F.3d 1326, 1331 (Fed. Cir. 2014); PharmaStem Therapeutics, Inc. v. ViaCell, Inc., 491 F.3d 1342, 1364 (Fed. Cir. 2007); Pfizer, Inc. v. Apotex, Inc., 480 F.3d 1348, 1364, 1367–68 (Fed. Cir. 2007) (reasoning that "the expectation of success need only be reasonable, not absolute")).”
Applicant's arguments fail to comply with 37 CFR 1.111(b) because they amount to a general allegation that the claims define a patentable invention without specifically pointing out how the language of the claims patentably distinguishes them from the references.
Applicant's arguments do not comply with 37 CFR 1.111(c) because they do not clearly point out the patentable novelty which he or she thinks the claims present in view of the state of the art disclosed by the references cited or the objections made. Further, they do not show how the amendments avoid such references or objections.
Rejections of record are maintained.
Double Patenting
Applicant states they’ll submit a terminal disclaimer, if warranted, in the future. Therefore, NSDP rejections are maintained.
Conclusion
THIS ACTION IS MADE FINAL. 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 JACKSON J HERNANDEZ whose telephone number is (571)272-5382. The examiner can normally be reached Mon - Thurs 7:30 to 5.
Examiner interviews are available via telephone and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Kortney L. Klinkel can be reached at (571) 270-5239. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/JACKSON J HERNANDEZ/Examiner, Art Unit 1627
/SARAH PIHONAK/Primary Examiner, Art Unit 1627
