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 17-30 are pending.
Claim 23 and 28 are amended.
Claims 1-16 are cancelled.
Response to Amendments
Applicant’s amendments filed 01 August 2025 are acknowledged.
Claim Objections
Applicant’s amendment to claim 23 is sufficient to overcome the
objection of the claim. The claim dependency has been corrected. The objection is withdrawn.
Claim Rejections - 35 USC § 112
Applicant’s amendment to claim 28 is sufficient to overcome the rejection of claim 28 under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Claim 28 has been amended to remove the indefinite limitation. The rejection is withdrawn.
Response to Arguments
Applicant’s arguments filed 01 August 2025 have been fully considered but they are not persuasive.
Applicant argues that Schaub, aka Schaub ‘282 in the rejections, Limbach, and Schubert do not disclose the limitations as recited in the instantly pending claims. These arguments have been considered but are not persuasive for the reasons set forth in the response to arguments below.
In response to applicant’s arguments on pages 5-7 of the remarks filed on 01 August 2025 that Schaub specifically teaches organic solvents that are “incompletely miscible with water”, that the instantly claimed DMF is miscible with water, a person of ordinary skill in the art would not be motivated by the teachings of Schaub to use the water miscible DMF solvent in the synthesis of α,β-ethylenically unsaturated carboxylic acid salt, and “[t]here would have been no reasonable expectation of success in incorporating DMF into the process of Schaub”. The examiner recognizes that obviousness may be established by 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).
Base claim 17 of the instant application states “comprising …”. MPEP 2111.03 I. states “[t]he transitional term “comprising”, which is synonymous with “including,” “containing,” or “characterized by,” is inclusive or open-ended and does not exclude additional, unrecited elements or method steps” and MPEP 2144.04 IV.C. states “selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results”. Therefore, the instantly claimed steps do not “exclude additional, unrecited elements or method steps” and the instant claims also do not exclude “selection of any order of performing [the] process steps”. For example, base claim 17 may include one or more solvents in addition to DMF.
During patent examination, the pending claims must be “given their broadest reasonable interpretation consistent with the specification”, see MPEP 2111. In this case, the instant specification states the choice of organic solvent is based on the solubility of reactants in the solvent, “[t]he organic solvent of the process of the invention may be an amide or a urea or contain at least one amide and at least one urea substructure”, see Pg. 4, Ln. 15-Pg. 5, Ln. 4, mixtures of solvent, and “N,N-dimethylformamide, N,N-dibutylformamide and N-formylmorpholine are particularly preferred organic solvents”, see Pg. 5, Ln. 25-Pg. 6, Ln. 33.
Schaub teaches the use of organic solvents that are “incompletely miscible with water at a pressure of 1 bar at at least one temperature T and selected from amides and ureas”, such as the solvent may also “be an amide or a urea or contain at least one amide and at least one one urea substructure”, see Pg. 6, Ln. 25-Pg. 7, Ln. 2, mixtures of organic solvents, see Pg. 34, Lns. 1-5, and the amide solvent is “an Ν,Ν-disubstituted formamide … The substituents are preferably independently selected from linear or branched C1-C16-alkyl”, where “[t]he most preferred organic solvent is N,N-Dibutylformamide” (DBF), see Pg. 7, Ln. 29-Pg. 8, Ln. 4, i.e. N,N-dimethylformamide is a C1 alkyl substitute, and the urea solvent is preferably a carbamide, see Pg. 7, Lns. 1-2 and 23-27. Schaub also teaches “[o]ne or more immiscible or only partly miscible liquid phases can be used”, see Pg. 30, Ln. 24, and “[t]he organic solvent can, for example, be selected from amides and ureas of which at most 10 % by weight, preferably at most 8 % by weight, more preferably at most 6 % by weight, most preferably at most 4 % by weight, in particular at most 2 % by weight are soluble in water at a pressure of 1 bar at at least one temperature T, based on the total weight of water and solvent.”, see Pg. 7, Lns. 4-14.
““The use of patents as references is not limited to what the patentees describe as their own inventions or to the problems with which they are concerned. They are part of the literature of the art, relevant for all they contain.” In re Heck, 699 F.2d 1331, 1332-33, 216 USPQ 1038, 1039 (Fed. Cir. 1983) (quoting In re Lemelson, 397 F.2d 1006, 1009, 158 USPQ 275, 277 (CCPA 1968)). 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).” ““Furthermore, “[t]he prior art’s mere disclosure of more than one alternative does not constitute a teaching away from any of these alternatives because such disclosure does not criticize, discredit, or otherwise discourage the solution claimed….”. In re Fulton, 391 F.3d 1195, 1201, 73 USPQ2d 1141, 1146 (Fed. Cir. 2004).”, see MPEP 2123. Since Schaub teaches a variety of preferred embodiments and one embodiment is a mixture of solvents with differing water miscibility are used in the reaction process, a person of ordinary skill in the art has good reason to use a mixture of water miscible DMF up to 10 % by weight and at least 90 % by weight of water immiscible phencarbamide and/or DBF, by pursuing the known options within their technical grasp for the benefit of controlling and desirably tailoring “[t]he loss of solvent via the aqueous phase” to facilitate the desired “recycling of the solvent into the carboxylation reaction and the further purification of the α,β-ethylenically unsaturated carboxylic acid salt from” the aqueous phase, see Schaub, Pg. 7, Lns. 4-14, MPEP 2141 and for solubility, see Haynes, “CRC Handbook of Chemistry and Physics”, 2017, 97th Edition, CRC Press, Pgs. 3-1, 3-154, 3-210, 3-444.
For the reasons stated above, applicant’s arguments regarding the above are not persuasive.
In response to applicant’s arguments on pages 5-7 of the remarks filed on 01 August 2025 that Schaub only teaches liquid-liquid separation and does not teach mechanical separation, a person of ordinary skill in the art would not be motivated by the teachings of Schaub to use mechanical separation, and “Limbach provides no incentive for the skilled person to use specifically DMF in the process of claim 1, and to perform a mechanical separation instead of a liquid-liquid separation step”, the test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981), and the fact that the inventor has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious, see Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985).
In this case, Schaub does teach separation by mechanical means, such as centrifugation and vacuum evaporation, see Schaub, Pg. 42, Lns. 9-13. Limbach is applied to teach the specifics of the mechanical separation of an α,β-ethylenically unsaturated carboxylic acid from a reaction solution containing mixtures of solvents, such as water miscible dimethylformamide and water immiscible chlorobenzene, see Limbach, Pg. 12, Lns. 21-29; Pg. 17, Lns. 7-13 and Haynes, “CRC Handbook of Chemistry and Physics”, 2017, 97th Edition, CRC Press, Pgs. 3-1, 3-98, 3-210. As stated by applicant’s on page 7 of the remarks filed on 01 August 2025, Limbach teaches solid-liquid separation, liquid-liquid separation, and an “example in Limbach exemplifying the complete catalytic formation of sodium acrylate, example 7, employs chlorobenzene”, see Limbach, Pg. 17, Lns. 8-33; Pg. 22, Ln. 16-Pg. 23, Ln. 4. Since both Schaub and Limbach teach separation of α,β-ethylenically unsaturated carboxylic acid from a mixture of organic solvents that are water miscible and water immiscible, a person of ordinary skill in the art has good reason to separate unsaturated carboxylic acids from a mixture of organic solvents by pursuing the known options within their technical grasp, such as the mechanical techniques as taught by Limbach, for the benefit of efficiently separating the acid at high yield while also efficiently recycling and capturing valuable reactants and by-products, see Limbach, Pg. 17, Ln. 8-Pg. 18, Ln. 2 and MPEP 2141.
For the reasons stated above, applicant’s arguments regarding the above are not persuasive.
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 17-23 and 27-30 are rejected under 35 U.S.C. 103 as being unpatentable over Schaub et al. (WO2017178282, cited by applicant 03 October 2022, hereinafter Schaub ‘282) in view of Limbach et al. (WO2013098772, hereinafter Limbach ‘772).
Claim 17 Schaub ‘282 discloses a catalytic process for preparing an α,β-ethylenically unsaturated carboxylic acid salt (Pg. 4, Lns. 9-24, “a catalytic process for preparing an α,β-ethylenically unsaturated carboxylic acid salt”; Pg. 41, Ln. 31-Pg. 42, Ln. 17, Examples 1-13, Table 1), comprising
a) contacting an alkene and carbon dioxide with a carboxylation catalyst, N,N-dimethylformamide, and an alkoxide having a secondary or tertiary carbon atom directly bound to an [O-] group (Pg. 4, Lns. 9-24, “contacting an alkene and carbon dioxide with a carboxylation catalyst being a transition metal complex, an alkoxide, and an organic solvent”; Pg. 7, Lns. 29-32, “The organic solvent is, for example, an Ν,Ν-disubstituted formamide … The substituents are preferably independently selected from linear or branched C1-C16-alkyl”; Pg. 8, Lns. 25-35, “Preferably, the alkoxide has a secondary or tertiary carbon atom directly bound to a [O-] group.”; Pg. 41, Ln. 31-Pg. 42, Ln. 17, Examples 1-13, Table 1), to obtain a crude reaction product comprising the α,β-ethylenically unsaturated carboxylic acid salt and an alcohol by-product which is the conjugate acid of the alkoxide (Pg. 4, Lns. 9-24, “to obtain an α,β-ethylenically unsaturated carboxylic acid salt”; Pg. 26, Ln. 32-Pg. 27, 3, “The alkoxide, e.g., secondary or tertiary alkoxide, is consumed stoichiometrically when the alkene and carbon dioxide are reacted to obtain the α,β-ethylenically unsaturated carboxylic acid salt. The alkoxide is protonated such that its conjugated acid, an alcohol, is obtained as a byproduct.”; Pg. 41, Ln. 31-Pg. 42, Ln. 17, Examples 1-13, Table 1); and
c) subjecting at least part of the crude reaction product to a mechanical separation step while maintaining the alcohol by-product in liquid form to obtain a solid phase comprising the α,β-ethylenically unsaturated carboxylic acid salt and a liquid phase comprising the carboxylation catalyst, the N,N-dimethylformamide and the alcohol by- product (Pg. 6, Lns. 19-24, “The crude reaction product can thus, for example, be processed further in a separation process that comprises a phase separation step (which may, for example be carried out after a polar solvent has been added), and a partial evaporation step, e.g., distilling off at least part of the alcohol (byproduct).”; Pg. 35, Lns. 4-10, “Preferably, the phase separation of the first and the second liquid phase is facilitated by changing temperature and/or pressure. Liquid-liquid extraction can be effected in all apparatus suitable for this purpose, such as stirred vessels, extractors or percolators.”; Pg. 32, Lns. 17-35, “a first liquid phase in which the α,β-ethylenically unsaturated carboxylic acid salt is enriched, and a second liquid phase in which the carboxylation catalyst is enriched”; Pg. 35, Lns. 20-30, “The alcohol byproduct can be enriched either in the first or in the second liquid phase.”; Pg. 33, Ln. 17, “Preferably, the main constituent of the second liquid phase is the organic solvent.”; Pg. 41, Ln. 31-Pg. 42, Ln. 17, Examples 1-13, Table 1, “All volatiles were removed in vacuo from the aqueous phase to obtain the desired sodium acrylate as the residue.”).
Schaub ‘282 fails to disclose b) allowing the α,β-ethylenically unsaturated carboxylic acid salt to precipitate out from the crude reaction product.
Limbach ‘772 in the field of “a process for preparing an alkali metal or alkaline earth metal salt of an α,β-ethylenically unsaturated carboxylic acid” (Pg. 3, Ln. 37-Pg. 4, Ln. 8) and as stated in Schaub ‘282 (Schaub ‘282, Pg. 2, Ln. 23-Pg. 3, Ln. 14, “Limbach ‘772 et al. (WO 2013/098772, Chem. Eur. J. 2012, 18, 14017-14025) described a catalytic process for preparing an alkali metal or alkaline earth metal salt of an α,β-ethylenically unsaturated carboxylic acid”) teaches N,N-dimethylformamide (Pg. 12, Lns. 21-27, “The solvent selected is one in which the transition metal complex has good solubility.
Examples include … alcohols such as … dimethylformamide”); b) allowing the α,β-ethylenically unsaturated carboxylic acid salt to precipitate out from the crude reaction product (Pg. 17, Lns. 7-13, “the alkali metal or alkaline earth metal salt of the α,β-ethylenically unsaturated carboxylic acid may be sparingly soluble in the reaction medium and precipitate, such that it can be separated by solid-liquid phase separation, such as removal by filtration, decantation or centrifugation”).
Claim 18 Modified Schaub ‘282 discloses the catalytic process according to claim 17.
Schaub ‘282 fails to disclose wherein the mechanical separation step c) comprises a filtration step.
Limbach ‘772 teaches wherein the mechanical separation step c) comprises a filtration step (Pg. 17, Lns. 7-13, “the alkali metal or alkaline earth metal salt of the α,β-ethylenically unsaturated carboxylic acid may be sparingly soluble in the reaction medium and precipitate, such that it can be separated by solid-liquid phase separation, such as removal by filtration, decantation or centrifugation”).
Claim 19 Modified Schaub ‘282 discloses the catalytic process according to claim 17. Schaub ‘282 further discloses additionally comprising d) distilling the alcohol by-product (Pg. 6, Lns. 19-23, “The crude reaction product can thus, for example, be processed further in a separation process that comprises a phase separation step (which may, for example be carried out after a polar solvent has been added), and a partial evaporation step, e.g., distilling off at least part of the alcohol (byproduct). The phase separation and the partial evaporation steps may be carried out in any order.”) and optionally the N,N-dimethylformamide off from the liquid phase to obtain an alcohol by-product distillate fraction and optionally a N,N-dimethylformamide distillate fraction, and a residue fraction (Pg. 36, Ln. 1-Pg. 37, Ln. 34, “at least part of the second liquid phase, e.g., of the second liquid phase obtained in step b), is recycled into the carboxylation reaction, e.g., to step a). The second liquid phase may be recycled into the carboxylation reaction with or without further workup steps. Traces of water comprised by the second liquid phase can be removed by distillation or by contacting the second liquid phase with a drying agent. … the remaining alcohol byproduct can be recycled into the process, for example into the carboxylation reaction, e.g., to step a) … Alcohol byproduct can then be directly recycled into the carboxylation reaction”; Pg. 33, Ln. 17, “Preferably, the main constituent of the second liquid phase is the organic solvent.”).
Claim 20 Modified Schaub ‘282 discloses the catalytic process according to claim 19. Schaub ‘282 further discloses additionally comprising recycling at least part of the residue fraction to step a) (Pg. 36, Ln. 1-Pg. 37, Ln. 34, “at least part of the second liquid phase, e.g., of the second liquid phase obtained in step b), is recycled into the carboxylation reaction, e.g., to step a). The second liquid phase may be recycled into the carboxylation reaction with or without further workup steps. Traces of water comprised by the second liquid phase can be removed by distillation or by contacting the second liquid phase with a drying agent.”, i.e., if water is removed the remainder of the second liquid phase is a residue. “sufficient to regenerate the alkoxide from the alcohol byproduct comprised by the condensate … the remaining alcohol byproduct can be recycled into the process, for example into the carboxylation reaction, e.g., to step a)”).
Claim 21 Modified Schaub ‘282 discloses the catalytic process according to claim 19. Schaub ‘282 further discloses additionally comprising e) contacting at least part of the alcohol by-product distillate fraction obtained in step d) with an alkaline material to regenerate an alkoxide (Pg. 36, Ln. 1-Pg. 37, Ln. 34, “at least some of the alcohol byproduct formed in the carboxylation reaction is contacted with the alkaline material in order to regenerate the alkoxide and the regenerated alkoxide is recycled into the carboxylation reaction, e.g., to step a). It may, for example, be sufficient to regenerate the alkoxide from the alcohol byproduct comprised by the condensate, to regenerate the alkoxide from the alcohol byproduct comprised by the first liquid phase, or to regenerate the alkoxide from the alcohol byproduct comprised by the second liquid phase and to recycle only this regenerated alkoxide into the carboxylation reaction. If alkoxide is regenerated only from part of the alcohol byproduct that is comprised by the crude reaction product, the remaining alcohol byproduct can be recycled into the process, for example into the carboxylation reaction, e.g., to step a)”).
Claim 22 Modified Schaub ‘282 discloses the catalytic process according to claim 21. Schaub ‘282 further discloses additionally comprising recycling at least part of the regenerated alkoxide to step a) (Pg. 36, Ln. 1-Pg. 37, Ln. 34).
Claim 23 Modified Schaub ‘282 discloses the catalytic process according to claim 21.
Schaub ‘282 does not disclose additionally comprising f) contacting the solid phase obtained in step c) with a wash liquid to obtain a spent wash liquid and a purified solid phase in which the carboxylic acid salt is enriched.
Limbach ‘772 teaches additionally comprising f) contacting the solid phase obtained in step c) with a wash liquid to obtain a spent wash liquid and a purified solid phase in which the carboxylic acid salt is enriched (Pg. 21, Lns. 23-29, “The yellow precipitate formed was filtered. Washing with THF gave the (dtbpe)Ni( 2-sodium acrylate) complex ( 197 mg, 37%).”).
Claim 27 Modified Schaub ‘282 discloses the catalytic process according to claim 17. Schaub ‘282 further discloses wherein step c) is performed at a temperature in the range of 0 to 150 0C (Pg. 39, Lns. 11-17, “The temperature in the bottom of the distillation column is, for example, in the range from 60 to 200°C, preferably in the range from 80 to 180°C.”).
Claim 28 Modified Schaub ‘282 discloses the catalytic process according to claim 17. Schaub ‘282 further discloses wherein the alkoxide is a sodium alkoxide (Pg. 8, Lns. 25-35, “Preferably, the alkoxide has a secondary or tertiary carbon atom directly bound to a [O-] group.”; Pg. 10, Lns. 29-34, “Alkali metal and in particular sodium alkoxides are preferred. Preferred alkoxides are sodium iso-propoxide and sodium tert-butoxide.”).
Claim 29 Modified Schaub ‘282 discloses the catalytic process according to claim 17. Schaub ‘282 further discloses wherein the alkene is ethene (Pg. 25, Lns. 1-8, “A preferred alkene is ethene.”) and the α,β-ethylenically unsaturated carboxylic acid salt is sodium acrylate (Pg. 41, Ln. 31-Pg. 42, Ln. 17, Examples 1-13, Table 1, “to obtain the desired sodium acrylate”).
Claim 30 Modified Schaub ‘282 discloses the catalytic process according to claim 17. Schaub ‘282 further discloses wherein the carboxylation catalyst is a nickel or palladium complex which comprises a bidentate P,X ligand in which X is selected from the group consisting of P, N, O, and carbene, and the P and X atoms are separated by a bivalent linker that comprises 2 to 4 bridging atoms (Pg. 13, Lns. 1-2, “Ligands that coordinate to the transition metal, e.g., nickel or palladium, to form a five-, six-, or seven-membered ring are preferred.”; Pg. 14, Lns. 16-20, “The ligand is preferably a bidentate P,X ligand in which X is selected from the group consisting of P, N, O, and carbene, in particular a bidentate P,P ligand. The P and X atoms are, for example, separated by a bivalent linker that comprises 2 to 4 bridging atoms. The linker is preferably linked to the P atom by a single bond and linked to the X atom by a single bond and comprises 2 to 4 bridging atoms linked by single bonds.”; Pg. 23, Lns. 11-17, “The transition metal complex, e.g., palladium or nickel complex, may for example be obtained from the ligand and the transition metal, e.g., palladium or nickel, or from the ligand and a transition metal source, e.g., palladium or nickel source, comprising the transition metal, e.g., palladium or nickel, at oxidation state 0.”).
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified
the separation and the washing technique of Schaub ‘282 with the solid liquid separation and the washing technique teachings of Limbach ‘772 with a reasonable predictability of success. By applying “routine optimization” and “predictable results” to select the optimal separation and solvent washing techniques, as taught by Limbach ‘772, one of ordinary skill in the art would have been motivated to make these modifications because Limbach ‘772 provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to efficiently produce, separate, and purify an acrylate with minimal steps and environmental solvent system impact by pursuing the known options within their technical grasp, such as the use of a cheap and minimally hazardous solvent systems and separation techniques, for the benefit of producing an acrylate with minimal cost and process steps (Limbach ‘772, Pg. 3, Lns. 15-31, “This two-stage reaction regime is complex. Moreover, the cleavage of the lactone is slow and thus reduces the spacetime yield of such a process considerably.”; Schaub ‘282, Pg. 4, Lns. 4-7, “Carrying out these prior art transition metal-catalyzed carboxylation processes on an industrial scale would thus require substantial effort for avoiding any emission of base or for the separation of the α,β-ethylenically unsaturated carboxylic acid salt from the crude reaction product.”). See MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied, 426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design incentives and other market forces can prompt variations of it, either in the same field or a different one. If a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability. For the same reason, if a technique has been used to improve one device, and a person of ordinary skill in the art would recognize that it would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”. See MPEP 2141.
Further, In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929) states “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions”.
In addition, selection of a known material, such as an alcohol solvent system and wash, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). See MPEP 2144.07.
Claims 24-26 are rejected under 35 U.S.C. 103 as being unpatentable over Schaub et al. (WO2017178282, cited by applicant 03 October 2022, hereinafter Schaub ‘282) in view of Limbach et al. (WO2013098772, hereinafter Limbach ‘772) and Schubert et al. (US20100166644, hereinafter Shubert).
Claim 24 Modified Schaub ‘282 discloses the catalytic process according to claim 23, as detailed in the 35 USC 103 rejection above.
Schaub ‘282 does not disclose wherein the wash liquid is selected from alkanes and alcohols.
Shubert is in the field of precipitation synthesis of carboxylate compounds (Para. [0140], “Example 24 Preparation of an Al-1,2,4,5-benzenetetracarboxylic acid MOF … The precipitated product is filtered off, washed with 2×100 ml of DMF and 4×100 ml of methanol and dried at 200° C. in a vacuum drying oven for 16 hours.”) teaches wherein the wash liquid is selected from alkanes and alcohols (Para. [0140]).
Claim 25 Modified Schaub ‘282 discloses the catalytic process according to claim 24, as detailed in the 35 USC 103 rejection above.
Schaub ‘282 does not disclose wherein the wash liquid is the alcohol by-product.
Schaub ‘282 teaches “the remaining alcohol byproduct can be recycled into the process” (Pg. 36, Lns. 14-24).
Shubert teaches wherein the wash liquid is the alcohol (Para. [0140]).
Claim 26 Modified Schaub ‘282 discloses the catalytic process according to claim 24, as detailed in the 35 USC 103 rejection above.
Schaub ‘282 does not disclose wherein the wash liquid is the N,N-dimethylformamide.
Shubert teaches wherein the wash liquid is the N,N-dimethylformamide (Para. [0140]; Para. [0048], “The nonaqueous organic solvent is preferably … N,N-dimethylformamide (DMF)”).
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified
the washing liquid of Schaub ‘282 with the washing liquid teachings of Shubert with a reasonable predictability of success. By applying “routine optimization” and “predictable results” to select the optimal solvent washing techniques, as taught by Shubert, one of ordinary skill in the art would have been motivated to make these modifications because Shubert provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to efficiently produce, separate, and purify an acrylate with minimal steps and environmental solvent system impact by pursuing the known options within their technical grasp, such as the use of a cheap and minimally hazardous solvent systems and separation techniques, for the benefit of producing an acrylate with minimal cost and process steps (Limbach ‘772, Pg. 3, Lns. 15-31, “This two-stage reaction regime is complex. Moreover, the cleavage of the lactone is slow and thus reduces the spacetime yield of such a process considerably.”; Schaub ‘282, Pg. 4, Lns. 4-7, “Carrying out these prior art transition metal-catalyzed carboxylation processes on an industrial scale would thus require substantial effort for avoiding any emission of base or for the separation of the α,β-ethylenically unsaturated carboxylic acid salt from the crude reaction product.”). See MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied, 426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design incentives and other market forces can prompt variations of it, either in the same field or a different one. If a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability. For the same reason, if a technique has been used to improve one device, and a person of ordinary skill in the art would recognize that it would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond his or her skill”. See MPEP 2141.
Further, In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929) states “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions”.
In addition, selection of a known material, such as the wash solution, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). See MPEP 2144.07.
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).
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Claims 17-30 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-14 of U.S. Patent No. 8697909 to Limbach et al. (hereinafter Limbach ‘909) in view of Schaub et al. (WO2017178282, cited by applicant 03 October 2022, hereinafter Schaub ‘282), Limbach et al. (WO2013098772, hereinafter Limbach ‘772), and Schubert et al. (US20100166644, hereinafter Shubert).
Regarding claim 17, the claims of Limbach ‘909 recite a catalytic process for preparing an α,β-ethylenically unsaturated carboxylic acid salt (Claim 1), comprising
a) contacting an alkene and carbon dioxide with a carboxylation catalyst, N,N-dimethylformamide, and an alkoxide (Claims 1, 2 & 11), to obtain a crude reaction product comprising the α,β-ethylenically unsaturated carboxylic acid salt (Claims 1 & 12-14); and
c) subjecting at least part of the crude reaction product to a separation step to obtain a solid phase comprising the α,β-ethylenically unsaturated carboxylic acid salt and a liquid phase comprising the carboxylation catalyst, the N,N-dimethylformamide (Claims 1 & 11-14).
The claims of Limbach ‘909 do not recite an alkoxide having a secondary or tertiary carbon atom directly bound to an [O-] group, an alcohol by-product which is the conjugate acid of the alkoxide;
b) allowing the α,β-ethylenically unsaturated carboxylic acid salt to precipitate out from the crude reaction product;
a mechanical separation step while maintaining the alcohol by-product in liquid form, and a liquid phase comprising the carboxylation catalyst, the N,N-dimethylformamide and the alcohol by- product.
Schaub ‘282 teaches a catalytic process for preparing an α,β-ethylenically unsaturated carboxylic acid salt (Pg. 4, Lns. 9-24, “a catalytic process for preparing an α,β-ethylenically unsaturated carboxylic acid salt”; Pg. 41, Ln. 31-Pg. 42, Ln. 17, Examples 1-13, Table 1), comprising
a) contacting an alkene and carbon dioxide with a carboxylation catalyst, N,N-dimethylformamide, and an alkoxide having a secondary or tertiary carbon atom directly bound to an [O-] group (Pg. 4, Lns. 9-24, “contacting an alkene and carbon dioxide with a carboxylation catalyst being a transition metal complex, an alkoxide, and an organic solvent”; Pg. 7, Lns. 29-32, “The organic solvent is, for example, an Ν,Ν-disubstituted formamide … The substituents are preferably independently selected from linear or branched C1-C16-alkyl”; Pg. 8, Lns. 25-35, “Preferably, the alkoxide has a secondary or tertiary carbon atom directly bound to a [O-] group.”; Pg. 41, Ln. 31-Pg. 42, Ln. 17, Examples 1-13, Table 1), to obtain a crude reaction product comprising the α,β-ethylenically unsaturated carboxylic acid salt and an alcohol by-product which is the conjugate acid of the alkoxide (Pg. 4, Lns. 9-24, “to obtain an α,β-ethylenically unsaturated carboxylic acid salt”; Pg. 26, Ln. 32-Pg. 27, 3, “The alkoxide, e.g., secondary or tertiary alkoxide, is consumed stoichiometrically when the alkene and carbon dioxide are reacted to obtain the α,β-ethylenically unsaturated carboxylic acid salt. The alkoxide is protonated such that its conjugated acid, an alcohol, is obtained as a byproduct.”; Pg. 41, Ln. 31-Pg. 42, Ln. 17, Examples 1-13, Table 1); and
c) subjecting at least part of the crude reaction product to a mechanical separation step while maintaining the alcohol by-product in liquid form to obtain a solid phase comprising the α,β-ethylenically unsaturated carboxylic acid salt and a liquid phase comprising the carboxylation catalyst, the N,N-dimethylformamide and the alcohol by- product (Pg. 6, Lns. 19-24, “The crude reaction product can thus, for example, be processed further in a separation process that comprises a phase separation step (which may, for example be carried out after a polar solvent has been added), and a partial evaporation step, e.g., distilling off at least part of the alcohol (byproduct).”; Pg. 35, Lns. 4-10, “Preferably, the phase separation of the first and the second liquid phase is facilitated by changing temperature and/or pressure. Liquid-liquid extraction can be effected in all apparatus suitable for this purpose, such as stirred vessels, extractors or percolators.”; Pg. 32, Lns. 17-35, “a first liquid phase in which the α,β-ethylenically unsaturated carboxylic acid salt is enriched, and a second liquid phase in which the carboxylation catalyst is enriched”; Pg. 35, Lns. 20-30, “The alcohol byproduct can be enriched either in the first or in the second liquid phase.”; Pg. 33, Ln. 17, “Preferably, the main constituent of the second liquid phase is the organic solvent.”; Pg. 41, Ln. 31-Pg. 42, Ln. 17, Examples 1-13, Table 1, “All volatiles were removed in vacuo from the aqueous phase to obtain the desired sodium acrylate as the residue.”).
Limbach ‘772 teaches N,N-dimethylformamide (Pg. 12, Lns. 21-27, “The solvent selected is one in which the transition metal complex has good solubility.
Examples include … alcohols such as … dimethylformamide”); b) allowing the α,β-ethylenically unsaturated carboxylic acid salt to precipitate out from the crude reaction product (Pg. 17, Lns. 7-13, “the alkali metal or alkaline earth metal salt of the α,β-ethylenically unsaturated carboxylic acid may be sparingly soluble in the reaction medium and precipitate, such that it can be separated by solid-liquid phase separation, such as removal by filtration, decantation or centrifugation”); b) allowing the α,β-ethylenically unsaturated carboxylic acid salt to precipitate out from the crude reaction product (Pg. 17, Lns. 7-13, “the alkali metal or alkaline earth metal salt of the α,β-ethylenically unsaturated carboxylic acid may be sparingly soluble in the reaction medium and precipitate, such that it can be separated by solid-liquid phase separation, such as removal by filtration, decantation or centrifugation”).
Regarding claim 18, the claims of Limbach ‘909 do not recite wherein the mechanical separation step c) comprises a filtration step.
Limbach ‘772 teaches wherein the mechanical separation step c) comprises a filtration step (Pg. 17, Lns. 7-13, “the alkali metal or alkaline earth metal salt of the α,β-ethylenically unsaturated carboxylic acid may be sparingly soluble in the reaction medium and precipitate, such that it can be separated by solid-liquid phase separation, such as removal by filtration, decantation or centrifugation”).
Regarding claim 19, the claims of Limbach ‘909 do not recite additionally comprising d) distilling the alcohol by-product and optionally the N,N-dimethylformamide off from the liquid phase to obtain an alcohol by-product distillate fraction and optionally a N,N-dimethylformamide distillate fraction, and a residue fraction.
Schaub ‘282 teaches additionally comprising d) distilling the alcohol by-product (Pg. 6, Lns. 19-23, “The crude reaction product can thus, for example, be processed further in a separation process that comprises a phase separation step (which may, for example be carried out after a polar solvent has been added), and a partial evaporation step, e.g., distilling off at least part of the alcohol (byproduct). The phase separation and the partial evaporation steps may be carried out in any order.”) and optionally the N,N-dimethylformamide off from the liquid phase to obtain an alcohol by-product distillate fraction and optionally a N,N-dimethylformamide distillate fraction, and a residue fraction (Pg. 36, Ln. 1-Pg. 37, Ln. 34, “at least part of the second liquid phase, e.g., of the second liquid phase obtained in step b), is recycled into the carboxylation reaction, e.g., to step a). The second liquid phase may be recycled into the carboxylation reaction with or without further workup steps. Traces of water comprised by the second liquid phase can be removed by distillation or by contacting the second liquid phase with a drying agent. … the remaining alcohol byproduct can be recycled into the process, for example into the carboxylation reaction, e.g., to step a) … Alcohol byproduct can then be directly recycled into the carboxylation reaction”; Pg. 33, Ln. 17, “Preferably, the main constituent of the second liquid phase is the organic solvent.”).
Regarding claim 20, the claims of Limbach ‘909 do not recite additionally comprising recycling at least part of the residue fraction to step a).
Schaub ‘282 teaches additionally comprising recycling at least part of the residue fraction to step a) (Pg. 36, Ln. 1-Pg. 37, Ln. 34, “at least part of the second liquid phase, e.g., of the second liquid phase obtained in step b), is recycled into the carboxylation reaction, e.g., to step a). The second liquid phase may be recycled into the carboxylation reaction with or without further workup steps. Traces of water comprised by the second liquid phase can be removed by distillation or by contacting the second liquid phase with a drying agent.”, i.e., if water is removed the remainder of the second liquid phase is a residue. “sufficient to regenerate the alkoxide from the alcohol byproduct comprised by the condensate … the remaining alcohol byproduct can be recycled into the process, for example into the carboxylation reaction, e.g., to step a)”).
Regarding claim 21, the claims of Limbach ‘909 do not recite additionally comprising e) contacting at least part of the alcohol by-product distillate fraction obtained in step d) with an alkaline material to regenerate an alkoxide.
Schaub ‘282 teaches additionally comprising e) contacting at least part of the alcohol by-product distillate fraction obtained in step d) with an alkaline material to regenerate an alkoxide (Pg. 36, Ln. 1-Pg. 37, Ln. 34, “at least some of the alcohol byproduct formed in the carboxylation reaction is contacted with the alkaline material in order to regenerate the alkoxide and the regenerated alkoxide is recycled into the carboxylation reaction, e.g., to step a). It may, for example, be sufficient to regenerate the alkoxide from the alcohol byproduct comprised by the condensate, to regenerate the alkoxide from the alcohol byproduct comprised by the first liquid phase, or to regenerate the alkoxide from the alcohol byproduct comprised by the second liquid phase and to recycle only this regenerated alkoxide into the carboxylation reaction. If alkoxide is regenerated only from part of the alcohol byproduct that is comprised by the crude reaction product, the remaining alcohol byproduct can be recycled into the process, for example into the carboxylation reaction, e.g., to step a)”).
Regarding claim 22, the claims of Limbach ‘909 do not recite additionally comprising recycling at least part of the regenerated alkoxide to step a).
Schaub ‘282 teaches additionally comprising recycling at least part of the regenerated alkoxide to step a) (Pg. 36, Ln. 1-Pg. 37, Ln. 34).
Regarding claim 23, the claims of Limbach ‘909 do not recite additionally comprising f) contacting the solid phase obtained in step c) with a wash liquid to obtain a spent wash liquid and a purified solid phase in which the carboxylic acid salt is enriched.
Limbach ‘772 teaches additionally comprising f) contacting the solid phase obtained in step c) with a wash liquid to obtain a spent wash liquid and a purified solid phase in which the carboxylic acid salt is enriched (Pg. 21, Lns. 23-29, “The yellow precipitate formed was filtered. Washing with THF gave the (dtbpe)Ni( 2-sodium acrylate) complex ( 197 mg, 37%).”).
Regarding claim 24, the claims of Limbach ‘909 do not recite wherein the wash liquid is selected from alkanes and alcohols.
Shubert teaches wherein the wash liquid is selected from alkanes and alcohols (Para. [0140], “Example 24 Preparation of an Al-1,2,4,5-benzenetetracarboxylic acid MOF … The precipitated product is filtered off, washed with 2×100 ml of DMF and 4×100 ml of methanol and dried at 200° C. in a vacuum drying oven for 16 hours.”).
Regarding claim 25, the claims of Limbach ‘909 do not recite wherein the wash liquid is the alcohol by-product.
Schaub ‘282 teaches “the remaining alcohol byproduct can be recycled into the process” (Pg. 36, Lns. 14-24).
Shubert teaches wherein the wash liquid is the alcohol (Para. [0140]).
Regarding claim 26, the claims of Limbach ‘909 do not recite wherein the wash liquid is the N,N-dimethylformamide.
Shubert teaches wherein the wash liquid is the N,N-dimethylformamide (Para. [0140]; Para. [0048], “The nonaqueous organic solvent is preferably … N,N-dimethylformamide (DMF)”).
Regarding claim 27, the claims of Limbach ‘909 do not recite wherein step c) is performed at a temperature in the range of 0 to 150 0C.
Schaub ‘282 teaches wherein step c) is performed at a temperature in the range of 0 to 150 0C (Pg. 39, Lns. 11-17, “The temperature in the bottom of the distillation column is, for example, in the range from 60 to 200°C, preferably in the range from 80 to 180°C.”).
Regarding claim 28, the claims of Limbach ‘909 do not recite wherein the alkoxide is a sodium alkoxide, preferably a sodium alkoxide having a tertiary carbon atom directly bound to an [O-] group.
Schaub ‘282 teaches wherein the alkoxide is a sodium alkoxide, preferably a sodium alkoxide having a tertiary carbon atom directly bound to an [O-] group (Pg. 8, Lns. 25-35, “Preferably, the alkoxide has a secondary or tertiary carbon atom directly bound to a [O-] group.”; Pg. 10, Lns. 29-34, “Alkali metal and in particular sodium alkoxides are preferred. Preferred alkoxides are sodium iso-propoxide and sodium tert-butoxide.”).
Regarding claim 29, the claims of Limbach ‘909 recite wherein the alkene is ethene (Claim 10).
The claims of Limbach ‘909 do not recite the α,β-ethylenically unsaturated carboxylic acid salt is sodium acrylate.
Schaub ‘282 teaches wherein the alkene is ethene (Pg. 25, Lns. 1-8, “A preferred alkene is ethene.”) and the α,β-ethylenically unsaturated carboxylic acid salt is sodium acrylate (Pg. 41, Ln. 31-Pg. 42, Ln. 17, Examples 1-13, Table 1, “to obtain the desired sodium acrylate”).
Regarding claim 30, the claims of Limbach ‘909 recite wherein the carboxylation catalyst is a nickel or palladium complex which comprises a bidentate P,X ligand in which X is selected from the group consisting of P, N, O, and carbene, and the P and X atoms are separated by a bivalent linker that comprises 2 to 4 bridging atoms (Claims 3-9).
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified
the claims of Limbach ‘909 with the process of Schaub ‘282, the solid liquid separation and the washing technique teachings of Limbach ‘772, and the wash solvent of Shubert with a reasonable predictability of success. By applying “routine optimization” and “predictable results” to select the optimal process, separation, and solvent washing techniques, as taught by Schaub ‘282, Limbach ‘772, and Shubert, one of ordinary skill in the art would have been motivated to make these modifications because Schaub ‘282,