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 .
DETAILED ACTION
Claims 1-3,10-11 and 13-18 of H. Ito, et al., US 17/996,070 (10/12/2022) are pending. Claims 2-3,10-11 and 13 are withdrawn as directed to nonelected Groups; claims 1, 14-18 are under examination on merits and rejected.
Withdrawal of Office Action Finality
A request for continued examination of US 17/996,070 under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 04/06/2026 has been entered.
Election/Restrictions
Pursuant to the restriction requirement, Applicant confirmed the election of Group I (claim 1) made on 04/18/2025 over the phone without traverse in the reply filed on 10/31/2025.
Applicant added new claims 14-18 in the reply filed on 04/06/2026, thus now the elected Group I comprises claims 1, 14-18. Claims 2-3,10-11 and 13 drawn to non-elected Groups (I)-(IV) are withdrawn from consideration pursuant to 37 CFR 1.142(b). The Restriction requirement is maintained as FINAL.
Withdrawal Claim Rejections - 35 USC § 112(a) (Scope of Enablement)
Rejection of claim 1 under 35 U.S.C. 112(a)(scope of enablement) is withdrawn in view of claim 1 has been amended by limiting of the metal as Mg, Ca or Li, or metal compound comprising as Mg, Ca or Li.
Withdrawal Claim Rejections - 35 USC § 103
Rejection of Claim 1 under 35 U.S.C. 103 as being unpatentable over C. Hofmann, et al, US20190161505A1(2019)(“Hofmann”) is withdrawn in view of claim 1 has been amended with additional limitation of “in a batch process”, which cannot met by Hofmann because Hofmann is a continuous process.
Claim Objections
Claims 1 and 16 are objected to on the grounds of improper parentheticals, for example “(Mg)” in claim 1. While Applicant may intend that the parenthetical phrase adds clarification, it is at best superfluous and better practice is to amend so as to remove the parentheticals to avoid confusion as to whether Applicant improperly intends preferences within the claim. See MPEP § 2173.05(d). Correction of all such parentheticals throughout the claims is required.
Claim 16 is further objected to and is required to amend the language of “the metal the metal constituting the metal compound are manganese” as “the metal and the metal constituting the metal compound are manganese” to clarify the claimed metal.
Claim Interpretation
Examination requires claim terms first be construed in terms in the broadest reasonable manner during prosecution as is reasonably allowed in an effort to establish a clear record of what applicant intends to claim. See, MPEP § 2111. Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. See MPEP § 2111.01. It is also appropriate to look to how the claim term is used in the prior art, which includes prior art patents, published applications, trade publications, and dictionaries. MPEP § 2111.01 (III).
Interpretation of the term “mechanochemical process”
Claim 1 recites the term “mechanochemical process” in the follows context:
1. A method for producing an organometallic nucleophile, comprising . . . with each other by a mechanochemical process in which mechanical energy is applied to the organohalide and the metal or metal compound in the reaction vessel . . . .
The specification provides the following discussion with respect to the claimed “mechanochemical process”:
<Mechanochemical process>
The mechanochemical process is a processing method in which mechanical energy is applied to a reactant (particularly, a solid reactant) by means of, for example, shearing, compression, stretching, grinding, rubbing, kneading, mixing, dispersion, disintegration, or shaking to thereby activate the reactant and provide structural change, phase transition, reactivity, adsorbability, catalytic activity, etc. This is expected to lead to surface activation, an increase in surface area, an increase in lattice defect, a decrease in crystal grain size, amorphization, etc.
The device for the mechanochemical process is not particularly limited as long as it is a device capable of applying mechanical energy by the above means.
Specification at page 32, [0031] (emphasis added).
In working Examples 1-60, the specification teaches reactions of various organic halides with magnesium according to the following general equation.
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Specification at pages 77-84.
According to the information disclosed in the specification, the term “mechanochemical process” is broadly and reasonably interpreted as any physical force applied to a reaction mixture comprising the claimed organohalide, the claimed metal or metal compound, and the claimed ether compound.
Interpretation of “metal compound”, “ether compound”, and “organohalide”
Independent claim 1 recites the term “mechanochemical process” in the following context.
A method for producing an organometallic nucleophile, comprising
loading an organohalide, a metal or metal compound , and an ether compound. . . .
The specification provides the following definition with respect to the claimed “organohalide”:
The organohalide used in the method for producing an organometallic nucleophile according to the present invention is a compound (I) represented by formula (I) below.
A1-Xm (I)
In the formula,
A1 represents an optionally substituted m-valent aromatic hydrocarbon group, an optionally substituted m-valent aromatic heterocyclic group, an optionally substituted m-valent aliphatic hydrocarbon group, or an optionally substituted m-valent unsaturated aliphatic hydrocarbon group.
Each occurrence of X represents F (fluorine), Cl (chlorine), Br (bromine), or I (iodine).
m is the number of X and represents an integer of 1 or greater.
Specification at page 17, [0017].
Therefore, “organohalide” is interpreted as the definition provided by the specification.
The specification provides the following discussion with respect to the claimed “metal compound”:
The metal or metal compound is not particularly limited as long as it can react with the organohalide to form an organometallic nucleophile. Examples of the metal include one or more selected from the group consisting of alkaline-earth metals, alkali metals, transition metals, zinc, aluminum, indium, tin, bismuth, boron, silicon, gallium, germanium, antimony, lead, and rare-earth metals. Examples of the metal compound include one or more selected from the group consisting of salts of these metals (e.g., chlorides, bromides, iodides, nitrates, sulfates, and carbonates), oxides of these metals, and the like.
Specification at page 29,[0026].
Based on its plain meaning and consistent with the specification, the term “metal compound” is broadly and reasonably interpreted as any compound comprising a metal.
The specification provides the following discussion with respect to the claimed “ether compound”:
The ether compound is a compound having one or more ether bonds (-O-) in a molecule, and is not particularly limited as long as it is a compound inactive in the reaction between the organohalide and the metal or metal compound.
Specification at page 30,[0028]. Therefore, consistent with the specification, the term “ether compound” is broadly and reasonably interpreted as any compound comprising a one or more “C-O-C“.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
35 USC § 102 Rejection over Atau
Claims 1 and 14, 17-18 are rejected under 35 U.S.C. 102 (a)(1)as being anticipated by I. Atau, et al, EP1705719 A1 (2006)(“Atau”).
Atau teaches a method for production of methyl magnesium iodide
[0341] Into a nitrogen-purged, 300-ml four-neck flask are introduced at room temperature 4.01 g (167 mmol) of magnesium shavings having a purity of 3 N and 68 ml of diisoamyl ether which had been fully dehydrated using molecular sieves. After the flask is equipped with a dry-ice condenser and the inner temperature is adjusted to 20°C, 27.89 g (197 mmol) of methyl iodide is added dropwise to the solution in the flask over about 2 hours. During this procedure, the temperature in the flask is controlled so as not to exceed 40°C. Following the dropwise addition, stirring is carried out at room temperature for 12 hours.
[0342] The resulting reaction mixture is filtered. Methyl magnesium iodide is generated in a yield of 97.0% (162 mmol), as measured according to the Gilman double titration method (described in H. Gilman, F.K. Cantledge, J. Organomet. Chem., 2, 447 (1964)).
Atau at page 31, [0341]-[0342], emphasis added.
The Atau process comprises:
(i). loading 167 mmol of magnesium, 197 mmol of methyl iodide, and 334 mmol of diisoamyl ether[ (68 ml ×0.778 g/ml1)÷158.28 g/mol2 = 334 mmol] in a reaction vessel; wherein, the molar ration between diisoamyl ether and methyl iodide is 1.70:1 (334/197);
(ii). the reaction mixture is stirred for 12 h, therefore, an mechanical energy is applied to both methyl iodide and magnesium; during which methyl iodide reacts with magnesium and methyl magnesium iodide is formed in the presence of diisoamyl ether;
(iii). The reaction process is a mechanochemical process per claim interpretation above because there is physical force from the stirrer is applied onto the reaction mixture.
Thus, Atau meets each and every limitation of claims 1, 14, 17-18, therefore, claims 1, 14, 17-18, are anticipated.
35 USC § 102 Rejection over Mochida
Claims 1, 15, 18 are rejected under 35 U.S.C. 102 (a)(1)as being anticipated by K. Mochida, et al, 332(3), Journal of organometallic chemistry, 247-252 (1987)(“Mochida”).
Mochida teaches a method for preparation of organocalcium halides by cocondensation of calcium vapor with solvents. Mochida at title.
Mochida teaches that the formation of organocalcium halides was identified by hydrolysis or deuterolysis of the products, yielding RH or RD as indicated below:
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Mochida at page 248, paragraph 2 under Table 1.
Per Experimental section, Mochida teaches that calcium atom-solvent slurries was prepared as below:
Preparation of calcium atom-solvent slurries
Calcium atom-solvent slurries were produced using essentially the same apparatus and conditions described previously. A typical procedure is described below. Calcium metal (0.5 g, 12.5 mmol) was vaporized at a rate of ca. 20 mg min-1, at a temperature of 900-1000°C using a resistance-heated, alumina-coated tungsten spiral crucible (4.0-5.0 V, 15 A) connected to copper electrodes, in vacuo (ca. 5 x 10-3 Torr). During the vaporization of calcium metal, a large excess of THF (20 cm3) was introduced as a vapor through a perforated inlet tube. The THF was cocondensed onto the walls of a quartz reaction flask containing the tungsten crucible (crucible was kept at 900-1000°C). The reaction flask was immersed in liquid nitrogen during the entire operation. Then the reaction flask was allowed to warm to room temperature and left to stand for 1 h. The reaction flask was evacuated and then filled with argon.
Mochida at page 251, Preparation of calcium atom-solvent slurries, emphasis added.
Thus, calcium atom-solvent slurries is consisted of 12.5 mmol of calcium metal and 247 mmol of THF [(20 ml × 0.889 g/ml3) ÷ 72.11 g/mol4 = 0.247 mole], therefore, THF is 19.76 times molar amounts of calcium metal.
Per Experimental section, Mochida also teaches the process for Reactions of calcium atom-THF slurry with organic halides as follows:
The reaction with octyl bromide is described as a typical example. The calcium atom-THF slurry was shaken vigorously and a given volume of calcium atom-THF slurry was placed quickly in a two-necked 50 cm3 flask equipped with a serum cap and reflux condenser in an argon-filled glove box. Ten times5 molar amounts of octyl bromide were then syringed in. The reaction mixture was stirred at 50 ° C for 2 h under argon. After the reaction mixture had been hydrolysed with dilute HCl, the organic layer was extracted with ether. The products were identified by comparing their GC-MS and their retention times on GLC with those of authentic samples.
Mochida at page 251, Reactions of calcium atom-THF slurry with organic halides, emphasis added.
The Mochida process for Reactions of calcium atom-THF slurry with organic halides comprises:
(i). loading 1.0 equivalent of a metal that is calcium, 19.6 equivalents of THF that is an ether compound, and 10.0 equivalents of organohalide that is octyl bromide in a reaction vessel; wherein, the molar ration between THF and octyl bromide is 1.96:1;
(ii). the reaction mixture is stirred for 2 h, therefore, an mechanical energy is applied to both octyl bromide and calcium metal; during which octyl bromide reacts with calcium metal and octylcalcium bromide is formed in the presence of THF.
(iii). The reaction process is a mechanochemical process per claim interpretation above because there is physical force from the stirrer is applied onto the reaction mixture.
Thus, Mochida meets each and every limitation of claims 1, 15 and 18, therefore, claims 1, 15 and 18 are anticipated.
35 USC § 102 Rejection over Peng
Claim 16 is rejected under 35 U.S.C. 102 (a)(1)as being anticipated by Z. Peng, et al, 12.39 Organic & Biomolecular Chemistry 7800-7809 (2014)(“Peng”).
Peng teaches a method of preparation of the compound (2-Bromophenyl)(phenyl)methanol (4a) as follow:
2-Bromobenzaldehyde (3a, 333 mg, 1.8 mmol) and THF (1 mL) were placed in an argon-flushed flask. To this mixture was added phenylmanganese(II) chloride (2a, 10 mL) dropwise at 10 °C. The reaction mixture was continuously stirred for 12 h followed by quenching with ammonium chloride (5 mL). The aqueous layer was extracted with ethyl acetate (3 × 20 mL). The combined organic phases were dried over MgSO4, the solvent was removed in vacuo. Purification by flash column chromatography (SiO2, petroleum ether–ethyl acetate = 20
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1) afforded 4a (347 mg, 73%) as a colorless liquid.
Peng at page 7804, left col. (2-Bromophenyl)(phenyl)methanol (4a), emphasis added.
The peng method comprises:
(i). loading 10 ml of phenylmanganese(II) chloride that is a metal compound comprising manganese, 12.3 mmol [(1 ml × 0.889 g/ml) ÷ 72.11 g/mol = 0.0123 mole] of THF that is an ether compound, and 1.8 mmol of 2-bromobenzaldehyde that is an organobromine comprising bromide bonded to a benzene ring in a reaction vessel; wherein, the molar ration between THF and 2-bromobenzaldehyde is 6.8 (12.3/1.8);
(ii). the reaction mixture is stirred for 12 h, therefore, an mechanical energy is applied to both 2-bromobenzaldehyde and phenylmanganese(II) chloride; during which 2-bromobenzaldehyde reacts with phenylmanganese(II) chloride and product is formed in the presence of THF;
(iii). The reaction process is a mechanochemical process per claim interpretation above because there is physical force from the stirrer is applied onto the reaction mixture.
The peng method meets each and every limitation of the cited active steps in claim 16, therefore, claim 16 is anticipated. The preamble language of “for producing an organometallic nucleophile” is interpreted as intended use. MPEP 2111.02. II.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Kruijs teaches a method of synthesis of Grignard reagents with microwave assistance in the presence of THF. See van de Kruijs, et al, 8(7), Organic & Biomolecular Chemistry, 1688-1694 (2010)(“Kruijs”).
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/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 Density of diisoamyl ether
2 Molecular weight of diisoamyl ether
3 Density of THF
4 Molecular weight of THF
5 It should be based on the amount of metal Ca.
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