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 1-20 were filed on 07/20/2023. No preliminary amendments of the claims were submitted.
Claims 1-20 are currently pending and under examination.
Priority
The instant application claims domestic benefit to U.S. provisional application no. 63/390,753 filed on 07/20/2022. Applicant’s claim for benefit of a prior-filed application under 35 U.S.C 119(e) is acknowledged.
Claim Objections
Claim 18 is objected to because of the following informalities: Claim 18 does not contain a period at the end of the sentence. Each claim begins with a capital letter and ends with a period. (see MPEP 608.01(m)) Appropriate correction is required.
Claim Rejections - 35 USC § 112
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 12 and 15 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.
The term “a conventional alkali powder” in claims 12 and 15 is a subjective term which renders the claim indefinite. The term “a conventional alkali powder” is not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. Claims 12 and 15 compare the chemical properties of the alkali dendrites formed to the properties of “a conventional alkali powder.” The chemical properties of alkali powders are relative to the process in which they were produced and there is not one conventional method to make alkali powders which renders the comparison between the alkali dendrites and conventional alkali powders indefinite.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1-3, 5-6, 9, 11, 19, and 20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Brandsma et al. (Preparative Polar Organometallic Chemistry 1987, found in PTO-892).
Instant claims 19 and 20 are being interpreted by the examiner as product-by-process claims. "[Even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process." (See MPEP 2113(I))
Brandsma et al. teaches regarding solvents used in most syntheses with organolithiums hexamethylphosphoric triamide (Me2N)3P=O (HMPT, in English often abbreviated as HMPA) is a rather expensive solvent. However, in most cases a small amount as co-solvent is sufficient to obtain the desired acceleration of the reaction (see section 2, paragraph 5). Brandsma teaches although lithium and sodium amide are commercially available, the suspensions prepared in liquid ammonia are much more reactive, and most reactions with these bases are carried out in this solvent. Lithium and sodium amide can be obtained in a "dry" state by completely evaporating the ammonia, the last traces in a water-pump vacuum. The powders obtained are very reactive and must be stored under nitrogen (or argon) in well-closed bottles with rubber stoppers (see section 4.4, first paragraph). The experimental procedures for the preparation of lithium amide in liquid ammonia include the flask is charged with about 1 litre of liquid ammonia. This is done by placing the end of a plastic tube (about 10 mm internal diameter), connected to the ammonia cylinder, in the flask and cautiously turning on the tap of the cylinder (Note 1 and page 7). This operation takes 2 to 3 min. Stirring is started and ferric nitrate (ca. 400 mg, note 2) is added. One gram of lithium is directly cut into the flask in 4 to 6 pieces (Note 3) causing vigorous evolution of ammonia vapour (due to the exothermic dissolution of the metal and its conversion into the amide). The stopper is therefore not yet placed on the flask. As soon as the blue color of the dissolved metal has disappeared and a white to greyish (Note 4) suspension has formed, an additional 2 g of lithium is cut in (Note 5). The remainder of the 1.0 mol of metal is introduced in the same way. In order to prevent penetration of moisture during the conversion of the lithium, a loose plug of cotton wool is placed on the third neck. The conversion of the total amount of lithium requires about 30 min. When it is completed, the cotton wool is replaced by the stopper (or dropping funnel if a further conversion is to be carried out). The amide prepared in this way is a white, (or light-grey) rather thick suspension, which settles out (after stopping the stirrer) very slowly. If desired the amount of ammonia for 1 mol ofLiNH2 can be reduced to about 600 ml. In that case, however, the conversion of the last portion of metal may take longer and careful observation is necessary to ensure that no small pieces of unconverted metal are present in the thick suspension. The experimental procedures for the preparation of sodamide in liquid ammonia include about 1 L of liquid ammonia (see Exp. 6) is placed in the flask and ca. 400 mg of ferric nitrate is added with stirring. After a few seconds 3 g of the 1 mol of sodium are added in 0.5 g pieces (Note 1). Normally the blue color disappears after 10 min and a grey to black solution is formed. The remainder of the sodium is then introduced and in most cases the conversion is complete after 30 min. The greyish suspension which has formed, settles out soon after stirring has stopped leaving a supernatant solution which is grey to black. Some unconverted sodium in the upper part of the flask may be washed down by vigorous stirring for a short time. For some reactions "dry" sodamide is required. This can be prepared by placing the flask in a water bath at 35-40 °C after the conversion has completed. During this operation the outer necks are open. When the stream of ammonia has become faint, the stirrer is replaced with a stopper. A stopper and an outlet are placed on the other necks and the flask is evacuated by means of water aspirator, first without external heating. When the pressure has dropped below 100 mm Hg, the flask is warmed for an additional 15 min at ca. 35°C. Nitrogen is then admitted and the solid is scratched from the glass using a curved spatula. Then the flask is evacuated again, and warmed at 40°C for 30 min. The grey powder (partly small lumps) is transferred into a storage flask and the lumps broken by pressing with a glass rod. The flask is filled with nitrogen or (preferably) argon and closed with a well-greased glass stopper or rubber stopper.
As previously discussed, claim 19 is being interpretated as a product-by-process claim and as such, determination of patentability is based on the product itself. As required by claim 19, Brandsma et al. teaches the basic reagent for most reactions proceeding via (polar) organometallic intermediates is n-butyllithium (see section 1, paragraph 4).
As previously discussed, claim 20 is being interpretated as a product-by-process claim and as such, determination of patentability is based on the product itself. As required by claim 20, Brandsma et al. teaches for most syntheses’ sec- or tert-butyllithium can be replaced by the very reactive combination of n-butyllithium and potassium t-butoxide in THF [236, 239]. This is a clear solution which can be prepared by mixing solutions of t-BuOK in THF and n-BuLi in hexane at < -90°C. The specific advantage of the BuLi and t-BuOK-THF combination is the possibility of carrying out deprotonations that give thermolabile metallic intermediates (see section 1, paragraph 6).
Claims 1-3, 5, 8-9, and 11 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Elias Experiments (Screen captures from YouTube video clip entitled “Making Lithium Powder”, 5 pages, uploaded on 10/31/2020 by user “Elias Experiments”. Retrieved from Internet: <https://www.youtube.com/watch?v=6Wl7D7eNLaw>).
Elias Experiments teaches the reactivity of a chunk of lithium metal in water. The gas evolving from the metal was also shown to be flammable. (see Fig. 1) 58 g of lithium metal freshly cut from a large chuck of lithium metal in mineral oil was obtained and placed in a 400 mL beaker with mineral oil solvent (a little bit less than 200 mL of mineral oil was used). (see Fig. 2 and 3) Around 0.4 g of sodium metal was added to the beaker. (see Fig. 4) The beaker was transferred to an IKA-COMBIMAG RCT magnetic hotplate stirrer. The heating was set to “full blast” until the lithium metal became molten. The sodium was observed to melt prior to the lithium. Once most of the lithium was molten, the solution was transferred to a flask with a smaller opening to avoid oxidation and continued to be heated and vigorously stirred. (see Fig. 5) 0.22 mL of oleic acid was added to the solution. After stirring this solution for around 10 minutes, dry ice was added in batches to the mixture. After the mixture was cooled, the remaining oil (evaporation occurred while stirring the mixture) was filtered using vacuum filtration. (see Fig. 6) The vacuum filtration worked poorly at removing the mineral oil from the mixture. After filtering for a moment, the mixture in the funnel was diluted with petroleum ether and gravitationally filtered overnight. (see Fig. 7) The resulting powder, with a similar sound and texture to wet sand, was bottled up and the reactivity was tested by dropping an unknown amount into 500 mL of water in a 600 mL beaker. (see Fig. 8 and 9) The powder reacted with water much quicker than the chunk of metal used in the beginning of the video. The combustion of the gas evolved from the powder was also much larger than that of the metal at the beginning of the video. (see timestamps 0:00-7:33)
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
Claims 1, 6, and 12-16 are rejected under 35 U.S.C. 103 as being unpatentable over Elias Experiments (Screen captures from YouTube video clip entitled “Making Lithium Powder”, 5 pages, uploaded on 10/31/2020 by user “Elias Experiments”. Retrieved from Internet: <https://www.youtube.com/watch?v=6Wl7D7eNLaw>) in view of NileRed (Screen captures from YouTube video clip entitled “Making Liquid Ammonia to Dissolve Sodium and Lithium metal”, 3 pages, uploaded on 01/01/2016 by user “NileRed”. Retrieved from Internet: <https://www.youtube.com/watch?v=gHokrNS1ask>, found in PTO-892).
The teachings of Elias Experiments were discussed above.
Elias Experiments differs from that of the instant invention in that Elias Experiments does not teach wherein the solvent comprises liquid ammonia as required by instant claim 6, wherein a surface area of the alkali dendrite is about 100 times greater than a surface area of a conventional alkali powder as required by instant claim 12, wherein a surface area of the alkali dendrite is about 2,950 times greater than a surface area of the alkali metal as required by instant claim 13, wherein a bulk morphology of the alkali dendrite is agglomerated in a dendritic form as required by instant claim 14, wherein a reactivity of the alkali dendrite is about 19 times greater than a reactivity of a conventional alkali powder, and wherein a reactivity of the alkali dendrite is about 199 times greater than a reactivity of the alkali metal.
NileRed teaches adding a little bit of liquid ammonia to a test tube that is cooled with dry ice. The ammonia is taken out of the dry ice bath and a little bit of lithium is added to the liquid (see Fig. 1). As the lithium dissolves in the ammonia, it produces a very nice blue color (see Fig. 2). The blue color is free electrons dissolved in the ammonia. When more lithium is added and the ammonia evaporates, the lithium will coat the side of the flask with some areas appearing copper-colored instead of blue (see Fig. 3). This is because at higher concentrations of the solvated electrons, the lithium takes on a copper color instead of blue. A second run is done using liquid ammonia as a solvent with sodium metal. After the sodium metal dissolved, the solution has a blue color (see Fig. 4). After adding more sodium, the solution took up a bronze color (see Fig. 5). After letting the liquid ammonia evaporate by leaving the test tube to warm up to room temperature, a white powder was let in the test tube (see Fig. 6). (see timestamps 9:12-12:46)
It would have been obvious before the effective filing date of the claimed invention to combine the method steps as taught by Elias Experiments while substituting liquid ammonia for mineral oil as a solvent for lithium and sodium as taught by NileRed to arrive at the claimed method. Furthermore, as the active method steps are made obvious by Elias Experiments and NileRed, the properties of the alkali dendrites such as surface area, bulk morphology, and reactivity that naturally flow from the method are also made obvious. It would have been prima facie obvious to combine the method steps for making lithium powder with using liquid ammonia as a solvent because, as taught by Elias Experiments, solvents such as mineral oil are difficult to remove from the metal but liquid ammonia will evaporate at room temperature from the metal. One of ordinary skill in the art would have a reasonable expectation of success because both references are in the field of organometallics.
Claims 1 and 7 are rejected under 35 U.S.C. 103 as being unpatentable over Brandsma et al. (Preparative Polar Organometallic Chemistry 1987, found in PTO-892).
The teachings of Brandsma et al. were discussed above.
The teachings of Brandsma et al. differ from that of the instant invention in that Brandsma et al. does not teach explicitly wherein the solvent comprises one or more of HMPA and different degrees of amines in the method of forming an alkali dendrite.
It would have been obvious to combine the teachings of Brandsma et al. before the effective filing date of the claimed invention by utilizing the method as taught by Brandsma et al. of forming sodium amide with a solvent comprising one or more of HMPA and different degrees of amines as taught by Brandsma et al. to arrive at the claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to modify the solvent choice in the method to form an alkali dendrite because, as taught by Brandsma et al., in most cases a small amount as co-solvent is sufficient to obtain the desired acceleration of the reaction. One of ordinary skill in the art would have a reasonable expectation of success because changing the solvent is a part of routine optimization of synthetic methods.
Claims 3, 4 and 8 are rejected under 35 U.S.C. 103 as being unpatentable over Brandsma et al. (Preparative Polar Organometallic Chemistry 1987, found in PTO-892) as applied to claim 1 above, and further in view of U.S. patent no. 4,206,191 (‘191, published 06/03/1980, found in PTO-892).
The teachings of Brandsma et al. were discussed above.
The teachings of Brandsma et al. differ from that of the instantly claimed invention in that Brandsma et al. does not teach wherein the lithium used in the method is a lithium rod and the method further comprising keeping a temperature of the alloy substantially constant during the combining step.
'191 teaches a low temperature method of preparing finely divided lithium amide (see Abstract).
Certain prior suggested procedures for the preparation of lithium amide have involved reacting neat lithium metal and ammonia at high temperatures, of the order, for instance, of about 400 C, or above. Such procedures were unsatisfactory because, among other disadvantages, of the difficulty of controlling the highly exothermic reaction (see Description of Prior Art References, second paragraph). In example 1(b), '191 teaches into the 5-Liter 3-neck flask equipment described above, there is added the catalyst slurry prepared as described in part (a) of this Example, followed by the addition of 63 g of ' diameter x 6' lithium metal rod previously precut into approximately '' to 1' long pieces. The reaction vessel and contents are then cooled to about - 40 by means of the dry ice-hexane cooling bath. Then 40 moles (680 g) of anhydrous liquid ammonia are added over a period of 30 minutes. This mixture is stirred at about - 40 for about 2 hours or until all of the lithium dissolves to form a bronze solution. '191 teaches an alternate method of preparing the cobalt catalyst is to interact the cobalt compound with an alkyllithium, for instance, butyllithium, solution in situ prior to the addition of the reactants and solvents. This avoids the use of dispersed lithium metal so that all of the lithium metal used in the method of the invention can be in bulk form. This alternate method is, generally speaking, preferred since it is more conveniently carried out.
It would have been obvious to combine the teachings of Brandsma et al. with the teachings of '191 before the effective filing date of the claimed invention by, as taught by '191, using a lithium rod as the lithium source in the method and further comprising keeping a temperature of the alloy substantially constant during the combining step to arrive at the claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to combine the method as taught by Brandsma et al. with the steps of using a lithium rod as the lithium source, as taught by '191, and carrying the combining step of the method out at a constant temperature, as taught by '191, because, as taught by '191, the use of a lithium rod allows the synthesis to be carried out more conveniently and helps to control the highly exothermic reaction. One of ordinary skill in the art would have a reasonable expectation of success because the form of the reagent and temperature are both routine reaction parameters in the process of method optimization.
Claims 9-10 are rejected under 35 U.S.C. 103 as being unpatentable over Brandsma et al. (Preparative Polar Organometallic Chemistry 1987, found in PTO-892) in view of U.S. patent no. 4,206,191 (‘191, published 06/03/1980, found in PTO-892) as applied to claim 8 above, and further in view of U.S. patent 3,542,512 ('512, published on 11/24/1970, found in PTO-892).
The teachings of Brandsma et al. were discussed above.
The teachings of Brandsma et al. differ from that of the instantly claimed invention in that Brandsma et al. does not teach wherein an amount of the solvent removed from the alloy can be in approximately a range of about 99% to about 100% with respect to a total amount of the solvent in the alloy.
'512 teaches a preparation of lithium amide. Various methods of preparing lithium amide are known. These methods, and other known methods as well, suffer a number of disadvantages. Significant among these disadvantages are the facts that the lithium amide produced is generally relatively impure, and is commonly obtained in the form of agglomerates or cakes which must be ground before use. The necessity for grinding the cakes of lithium amide to place the amide in a free-flowing form not only adds to the production costs of the amide, but, also, has an adverse effect on its purity in that it is exposed to atmospheric moisture during grinding. The lithium amide, when recovered, after washing and drying, is in the form of a white, free-flowing powder having a particle size commonly in the range of about 1 to about 10 microns. Yields of lithium amide obtained by the method of this invention are, as stated, essentially quantitative, ranging in excess of 95%, usually 96% to 98%, based on the quantity of lithium metal used. The purity of the final product is uniformly high, ranging from 95% to 99%, usually 96% to 98% (see paragraphs 1 and 3).
It would have been obvious to combine the teachings of Brandsma et al. with the teachings of '512 before the effective filing date of the claimed invention by drying the lithium product to a yield of 99% to arrive at the claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to combine the drying of the product to 99% yield with the other steps of the method because, as taught by '512, lithium amide produced is generally relatively impure, and is commonly obtained in the form of agglomerates or cakes which must be ground before use which adds to the production costs of the amide and has an adverse effect on its purity in that it is exposed to atmospheric moisture during grinding. One of ordinary skill in the art would have a reasonable expectation of success because both references are aimed at methodologies of making organolithium reagents.
Claims 17 and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Brandsma et al. (Preparative Polar Organometallic Chemistry 1987, found in PTO-892) as applied to claim 1 above, and further in view of Screttas et al. (Org. Lett. 2012, 14, 22, 5680–5683, found in PTO-892).
The teachings of Brandsma et al. were discussed above.
The teachings of Brandsma et al. differ from that of the instantly claimed invention in that Brandsma et al. does not teach further comprising reacting the alkali metal product with an organic halide to form an organometallic reagent and further synthetically transforming the organometallic reagent by alkylation to generate a yield of about 90% or more.
Screttas et al. teaches the following synthetic route: the formation of lithium spherules and further formation of o-tolyllithium using the lithium spherules previously formed. The o-tolyllithium is further reacted with ethyl 2-chlorooxoacetate to afford synthetically transformed products in yields ranging from 90-100% (see General Procedure for the Preparation of ethyl tolyl-2-oxoacetate in Supporting Information).
It would have been obvious to combine the teachings of Brandsma et al. with the teachings of Screttas et al. before the effective filing date of the claimed invention by forming the alkali metal product with the method as described by Brandsma et al. and the steps of further reacting the alkali metal product as taught by Screttas et al. to arrive at the claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to combine method of forming an alkali metal product with further synthetic steps because, as taught by Screttas et al., organolithiums are used in possible synthetic routes to desired compounds. One of ordinary skill in the art would have a reasonable expectation of success because both references are aimed at the study of alkali metal compound formation.
Conclusion
No claim is found allowable.
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/KRISTEN W BRADY/ Examiner, Art Unit 1692
/SCARLETT Y GOON/ Supervisory Patent Examiner, Art Unit 1693