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 .
Claim Status
Claims 1-7 were filed 2/1/2023. In a preliminary amendment filed on the same day, claims 1-7 were amended. Claims 1-7 are pending.
Priority
The instant application was filed 2/1/2023 and claims the benefit of the following priority applications:
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See filing receipt dated 7/31/2023. Acknowledgment is made of applicant's claim for foreign priority based on an application filed in INDIA on 5/4/2020. It is noted, however, that applicant has not filed a certified copy of the INDIA 202021018881 application as required by 37 CFR 1.55.
Specification/Drawings
The disclosure is objected to because of the following informalities: the following Schemes are blurry and illegible and should be redrawn:
Scheme I on p. 1;
Scheme II on p. 5; and
Scheme IIA on p. 5-6.
Additionally, in lines 14-7 of p. 1 of the specification, the following words should not be capitalized: “Propionic”, “Calcium”, “Sodium”, and “Propionate”.
Appropriate correction is required.
The drawings are objected to because it is blurry and illegible.
Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Claim Objections
Claims 1-3, 6, and 7 are objected to because of the following informalities:
In line 2 of claim 1, the limitation “N-Tert-butyl acrylamide” should be rewritten as –N-tert-butyl acrylamide--.
In claim 1, steps c) and f) recite pressure using the following unit “kg-g/cm2”. This is not standard nomenclature for a pressure. Based on the specification, this is a gauge (g) pressure in kg/cm2, therefore the pressure should be expressed as follows: “kg/cm2g”.
In the final line of step c) of claim 1, the definite article –the—should be inserted before the word “vinylic”.
In line 3 of step f) of claim 1, the definite article –the—should be inserted before the word “vent”.
In line 5 of step f) of claim 1, the word “remained” should be deleted and replaced by –remaining--.
In line 2 of step g) of claim 1, the word “till” should be deleted and replaced by –until--.
In line 2 of step g) of claim 1, the word “till” should be deleted and replaced by –until--.
In line 2 of step g) of claim 1, the word “to” in front of the word “temperature” should be deleted and replaced by the indefinite article –a--.
Claim 2 is objected to for missing a period at the end of the claim. See MPEP 608.01(m).
Line 2 of claim 3 is objected to because the word “Nickel” is not a proper noun and should be rewritten as –nickel--.
Line 3 of claim 3 is objected to because the word “Sodium” is not a proper noun and should be rewritten as –sodium--.
In the final line of claim 6, the phrase “is having” should be deleted and replaced by –has--.
In the final line of claim 7, the phrase “is having” should be deleted and replaced by –have--.
Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-7 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Step (a) of claim 1 recites the following in lines 1-2:
“charging N-tert-butyl acrylamide (30% to 36% w/v); and organic solvent (69% to 63% v/v); and a hydrogenation catalyst (1 % w/v) into a first reactor…”. It is not clear if the ranges within the parenthetical limitations are required or optional. Therefore, the limitation is indefinite.
Claims 2-7 do not cure the deficiencies and are rejected for depending from indefinite claim 1.
Claim 3 additionally contains the trademark/trade name “Raney”. Where a trademark or trade name is used in a claim as a limitation to identify or describe a particular material or product, the claim does not comply with the requirements of 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph. See Ex parte Simpson, 218 USPQ 1020 (Bd. App. 1982). The claim scope is uncertain since the trademark or trade name cannot be used properly to identify any particular material or product. A trademark or trade name is used to identify a source of goods, and not the goods themselves. Thus, a trademark or trade name does not identify or describe the goods associated with the trademark or trade name. In the present case, the trademark/trade name is used to identify/describe a hydrogenation catalyst and, accordingly, the identification/description is indefinite.
Claim Rejections - 35 USC § 112(d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 5 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Step e) of claim 1, from which claim 5 depends, requires “transferring the N-tert-butyl propanamide solution obtained in step (d) into a second reactor” and charging the second reactor with an aqueous solution of an alkali. Therefore, there is no embodiment of claim 1 which would include the step of claim 5 of drying the N-tertiary butyl propanamide to produce a solid form, because step (e) of claim 1 requires the (emphasis added) solution obtained in step (d) (as opposed to “a solution of the N-tert-butyl propanamide obtained in step (d)” or “the N-tert-butyl propanamide obtained in step (d)”). Nor does claim 5 recite that the steps only apply to a portion of the N-tertiary butyl amide from the solution at the end of step (d).
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
The Examiner notes that Examples C-1 to C-2 on p. 14 of the specification as filed describe the separation of N-tertiary butyl propanamide from filtrates as described in claim 5. However, as discussed above, the language used in present claim 1 appears to preclude this embodiment. The Examiner reminds the Applicant that any amendments to the claims should not contain new matter that is not fully supported by the specification as filed.
Subject Matter free from the Prior Art
Claims 1-7 appear to be free from the prior art.
The following is a statement of reasons for the indication of subject matter free from the prior art: the closest prior art to the claimed invention appears to be the teachings of Takata (US 3806543, published on 4/23/1974), Bonse (US 4496736, published 1/29/1985), Ueno (“Size Selective Olefin Hydrogenation by a Pd Nanocluster Provided in an Apo-Ferritin Cage” Angew. Chem. Int. Ed. 2004, 43, p. 2527-2530), and Verdolino (“On the mechanism of the rhodium catalyzed acrylamide hydrogenation” Journal of Molecular Catalysis A: Chemical, 324, 2010, p. 9-14).
Takata is directed toward a method for alkali-cleavage of N-tertiary-alkylamides (N-TAD) of formula R1-CONH-R2 (wherein R1 is a saturated or unsaturated hydrocarbon group having 2-3 carbon atoms of the methoxy derivative thereof, and R2 is a tert-alkyl group) in the presence of an alkali reagent and methanol (organic solvent) to produce a tert-alkylamine and carboxylic acid in very high yield. See abstract. When R1 is a saturated C2 hydrocarbon group, the amide of Takata corresponds to N-tertiary-butyl propanamide, the product of instant step d). When R1 is an unsaturated C2 hydrocarbon group, the amide of Takata corresponds to N-tert-butyl acrylamide, the starting material of instant step a) (expressly taught in col. 1, lines 34-40). Thus, Takata teaches that the starting material of step a) (acrylamide, C2 unsaturated compound) and the product of step d) (propanamide, C2 saturated compound) can both be used to produce tert-butyl amine under the disclosed conditions (which correspond to instant steps e-f). Takata teaches that alkali cleavage reaction temperature is above 140°C, preferably between 150-250°C and that the alkali is preferably caustic soda (NaOH/lye) or caustic potash (KOH). See claims.
Examples 1-4 and 9 of Takata subject N-tert-butyl acrylamide to the alkali cleavage reaction in the presence of methanol, caustic soda, and a polymerization inhibitor (hydroquinone monomethylether) to produce N-tert-butylamine in 60-84% yield (all examples), methyl acrylate (example 2), and acrylic acid (example 9). The other examples further teach the same reaction as applied to N-tert-butylmethoxypropionamide (containing a saturated C2 hydrocarbon substituted by a methoxy group at R1 of the amides of Takata) to produce N-tert-butylamine in 78-88% yield. The examples also teach that carboxylic acids, salts thereof, and esters thereof can also be recovered from the reaction as the other cleavage product (which would correspond to the claimed alkali metal propionates and instant step h).
Takata does not explicitly teach hydrogenating N-tert-butyl acrylamide to produce N-tert-butyl propanamide and then subjecting N-tertbutyl propanamide to the alkali cleavage reaction to produce N-tertbutylamine. Nor do the conditions of the alkali cleavage of Takata match those of instant steps e-f (different temperature ranges and concentrations and silent regarding pressure). Takata is also silent regarding the isolation of instant step g. Takata teaches obtaining a distillation condensate comprising tert-butylamine, water, and methanol, but does appear to separate tert-butylamine from said mixture via distillation. Takata instead reports the melting points of N-tert-butylamine picrate, which indicates that N-tert-butylamine is isolated as a picrate salt.
Bonse teaches an analogous process to that of Takata, wherein carboxylic acids and N-alkylamines are prepared simultaneously by the alkaline pressure hydrolysis of N-tert-alkyl carboxylic acid amides. A 5 to 50 wt% aqueous solution of an alkali metal hydroxide is employed in an amount of 1.0 to 1.3 moles per mol of amide and is carried out at a temperature of 200-350°C. See abstract and claims. The concentration range of the hydroxide and the temperature range of Bonse overlap with those of instant steps e-f. Bonse also teaches that the reaction takes place under elevated pressure within the range of 10-200 bar, which overlaps with the claimed range (1 kg/cm2g = about 1 bar). See col. 4, line 60-col. 5, line 29. Bonse teaches that when the reaction is complete, the reaction mixture is cooled and pressure is released. The t.-alkylamine is then removed from the reaction mixture by distillation. The distillation can also be effected by controlled release of the pressure of the reaction mixture while the latter is still hot (to produce the condensate of instant step f). This gives, if appropriate after a further distillation to remove water, a t.-alkylamine which has a purity higher than 97% in more than 95% theoretical yield. See col. 5, lines 30-40. The water removal distillation of Bonse corresponds to the first distillation of instant step g. Bonse further teaches isolating the carboxylic acid salts from the distillation bottoms (in the reactor) by customary methods. See col. 5, lines 48-64. Bonse also provides a review of the literature for forming tert-butylamine in col. 1, line 1-col. 2, line 30.
Bonse does not teach subjecting N-tert-butyl propanamide to the cleavage reaction. The amide precursors of Bonse correspond to compounds of formula (II) and are limited to those wherein A1 is an aromatic group, which does not include the claimed propanamides:
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. Nor does Bonse teach the second distillation of instant step g) or the hydrogenation process of instant steps a-d).
Ueno is directed toward size-selective olefin hydrogenation by a Pd Nanocluster Provided in an Apo-Ferritin Cage. See title and conclusion paragraph on p. 2529. Ueno teaches the hydrogenation of N-tert-butyl acrylamide (4) in the presence of a Pd-apo-ferritin catalyst (inventive example of Ueno) vs. a Pd particle catalyst (comparative). See the following Table 1 and discussion thereof on p. 2529:
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The TOF is defined as TOF = [product (mol)] per atom of Pd per hour in col. 1 on p. 2529. Therefore, a higher TOF corresponds to a more efficient catalyst. Ueno teaches that N-tert-butyl acrylamide (4) can be hydrogenated with both catalysts, but neither is very effective, especially as compared to the hydrogenation of acrylamide (1). Nor does Ueno provide yields.
Verdolino is directed toward the mechanism of rhodium catalyzed acrylamide hydrogenation. See abstract. Verdolino discusses prior art regarding the hydrogenation of alpha, beta-unsaturated amides (which includes acrylamides) in the introduction section I on p. 9-10. Verdolino indicates that though hydrogenations are known in the art, the mechanisms are not well-understood.
In summary, though Takata and Bonse teach analogous processes to instant steps e-h, they do not teach or suggest instant steps a-d. Ueno explicitly teaches the hydrogenation of N-tert-butylacrylamide, but no yield is given and the TOF data that is provided indicates that the reaction may not be particularly effective. Verdolino generally teaches that the understanding of the hydrogenation of acrylamides is limited and a search of the prior art has not provided any other conditions for hydrogenating N-tert-butyl amide. The experiments (B) on p. 11-13 of the specification as filed teach that the claimed hydrogenation can proceed in high yield (<99%) under the claimed conditions, including when palladium particle catalysts (Pd/C, the comparative and worse performing catalysts in Ueno) are employed. These results would not be predictable based on the prior art. Nor would it be obvious to modify the processes of Takata and Bonse to arrive at that claimed because they teach that N-tert-butylacrylamide can be directly cleaved to form tert-butylamine. Therefore, the instantly claimed process appears to be free from the prior art.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/AMY C BONAPARTE/Primary Examiner, Art Unit 1692