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 and 14-20 of H. Ito, et al., US 17/996,070 (10/12/2022) are pending, are under examination on merits and are rejected
Election/Restrictions
Pursuant to the restriction requirement, Applicant elected Group I (claim 1), without traverse, in the reply filed on 10/31/2025. Applicant added new claims 14-18 in the reply filed on 04/06/2026. Applicant added new claims 19-20 and cancelled claims 2-13 in the reply filed on 08/18/2026, now the elected Group I comprises claims 1, 14-20. The Restriction requirement is maintained as FINAL.
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 of “a mill, grinder, kneader, or vibratory fixed- vessel mixing device”
Claim 1 recites the term “a mill, grinder, kneader, or vibratory fixed- vessel mixing device” in the follows context:
1. A method for producing an organometallic nucleophile, comprising:
. . . .
wherein the mechanochemical process uses a mill, grinder, kneader, or vibratory fixed-vessel mixing device, for applying mechanical energy, . . .
. . . .
The specification does not provide definition for the claimed “a mill, grinder, kneader, or vibratory fixed-vessel mixing device”. The specification has an opening side discussion of the claimed “a mill, grinder, kneader, or vibratory fixed-vessel mixing device” as indicated below:
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.
Examples of such devices include one or more selected from the group consisting of:
mills such as ball mills, rod mills, jet mills, and SAG mills;
grinders such as rotary millstones and grinding machines;
(vibratory) fixed vessel type mixing devices of vibratory mill type, sieve type, etc.;
kneaders such as twin-screw kneaders, single-screw kneaders, mixers, and roll mills;
Specification at page 32, line 13-20 and page 33, 17-18, 24-25, emphasis added.
According to the information provided by the specification and the plain meaning of the words in the claim, the claimed mill device is broadly and reasonably interpreted as any device that can conduct cut, shaping, grinding, or crushing any materials; the claimed grinder device is broadly and reasonably interpreted as any device that can reduce a material into smaller fragments; the claimed kneader device is broadly and reasonably interpreted as any device that can conduct compression or mixing of a material; and the claimed vibratory fixed-vessel mixing device is broadly and reasonably interpreted as an device that can conduct vibration and mixing of a material.
Claim Rejections - 35 USC § 102
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.
Maintained 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 discussed in the previous Office action because there is physical force from the stirrer that is applied onto the reaction mixture.
(iv). the stirrer is a mixer that is a kneader device per the claim interpretation above and the information disclosed in the specification above.
Thus, Atau meets each and every limitation of claims 1, 14, 17-18, therefore, claims 1, 14, 17-18, are anticipated.
Maintained 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 co-condensation 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 discussed in the previous Office action because there is physical force from the stirrer that is applied onto the reaction mixture;
(iv). the stirrer is a mixer that is a kneader device per the claim interpretation above and the information disclosed in the specification above.
Thus, Mochida meets each and every limitation of claims 1, 15 and 18, therefore, claims 1, 15 and 18 are anticipated.
Maintained 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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:
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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 discussed in the previous Office action because there is physical force from the stirrer is applied onto the reaction mixture;
(iv). the stirrer is a mixer that is a kneader device per the claim interpretation above and the information disclosed in the specification above.
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.
Applicant’s argument
Applicant argues on the ground that the instant claim 1 has been amended with additional limitation of "the mechanochemical process uses a mill, grinder, kneader, or vibratory fixed vessel type mixing device, for applying mechanical energy", none of Atau, Mochida or Peng teaches this limitation and the rejection(s) is overcame. Response to the 102 rejections at page 5-6 in the Remarks filed on 08/18/2026. This argument is not persuasive because the specification teaches that a kneader device can be a mixer. Specification at page 33, line 24-25. A stirrer is one of mixer devices, therefore, it is a kneader device as claimed.
It needs to be noted that during the interview on 08/04/2026, Examiner said that the 102 rejections made in the Office action mailed on 04/14/2026 would be overcame by the proposed claim amendment. However, after reconsideration of the teachings from the specification, Examiner found that Examiner did not give a broadly and reasonable interpretation of the claimed devices recited by the proposed claim amendment during the interview.
New 35 USC § 102 Rejection over Howard
Claims 16 and 20 are rejected under 35 U.S.C. 102 (a)(1)as being anticipated by J. Howard, Exploring mechanochemistry for organic synthesis. Diss. Cardiff University, (2018)(“Howard”).
Howard teaches a method for synthesis organomanganese as indicated below. Howard at page 125, Table 5.1.
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The entry 15 method is conducted by:
(i). loading an organohalide that is ethyl-4-bromobutyrate, a metal that is Mn piece, and an ether compound that is THF, in a reaction vessel
wherein, the THF is 1.0 equivalents relative to 1 equivalent of ethyl-4-bromobutyrate; (ii). reacting of ethyl-4-bromobutyrate with Mn in a batch process to form compound 147 by a mechanochemical process in which mechanical energy;
(iii). the mechanical energy applied to the reaction mixture is produced by a mill device.
(iv). Howard also teaches that the mill device is a ball mill and the reaction is a batch process. See Howard at page 180, 6.5.1. line 1-4.
Thus, the Howard method meets each and every limitation of claims 16 and 20, therefore, claims 16 and 20 are anticipated.
New 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.
Claims 1, 14, 17-18 are rejected under 35 USC § 103 Rejection as being unpatentable over I. Atau, et al, EP1705719 A1 (2006)(“Atau”) in view of U. Hoffmann, et al, 68 Chemie lngenieur Technik (1996)(“Hoffmann”). Claim 19 is rejected as applied above for the rejection of claim 1, further in view of A. Stolle, et al, 40 Chem. Soc. Rev. 2317–2329 (2011)(“’Stolle”).
I. Atau, et al, EP1705719 A1 (2006)(“Atau”)
Atau teaches that trialkyl gallium ca be used as an ingredient for forming a compound semiconductor thin film. Atau at page 2. [0001].
Per Example 5-1, Atau teaches a method for production of trimethyl gallium by reacting of Ga2Me3I3 with methyl magnesium iodide. Atau at page 31, Example 5-1.
Atau teaches that methyl magnesium iodide is prepared as indicated below:
[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].
As detail discussed in the 102 rejection above that the Atau method of preparing of methyl magnesium iodide meets each and every limitation of claim 1.
Difference between Atau and Claim 19
The Atau method differs from claim 19 in that the mechanical energy applied to the reaction mixture is produced by a stirrer rather than a ball mill device.
U. Hoffmann, et al, 68 Chemie lngenieur Technik (1996)(“Hoffmann”)
Hoffmann is published in Germany and a copy of machine translation is attached as the second part, which results in the total page of the full reference is 8 and the format for citation of Hoffmann is x/8.
Hoffmann teaches that reaction for preparation of Grignard compound between sold and liquid is slow, so that sometimes long reaction time or increased temperature is required. Hoffmann at page 5/8, left col. the second paragraph under reaction equation (2). Hoffmann teaches that oxide layers on the magnesium chips against halide attack on magnesium and prevents the reaction from starting; solid by-products can also lead to a coating of the magnesium, which prevents complete conversion. Hoffmann at page 5/8, left col. the third paragraph under reaction equation (2).
Hoffmann teaches that those mentioned problems can be solved by using a reaction mill for the heterogeneous liquid/solid reaction because a reaction mill can:
permanent removal of inert surface layers,
generation of new surface, and
mechanical activation of the solid surface.
Hoffmann at page 5/8, right col. the second paragraph.
A. Stolle, et al, 40 Chem. Soc. Rev. 2317–2329 (2011)(“’Stolle”)
Stolle teaches that:
For bench-scale applications, ball mills are the reactors of choice used for the synthesis of various organic chemicals by mechanical activation of solid or solidified reactants (Scheme 1). The generic reaction scheme reflected the major influences which have to be considered when working with ball mills. Besides the type of ball mill, the material of milling ball(s) and beaker(s) influences the chemical reaction just like reaction time and milling frequency [Hz].
Stolle at page 2318, left col. under scheme 1, line 12-19, emphasis added. Scheme 1.
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Obviousness Rationales of claim 1, 14, 17-19
One of ordinary skill would have arrive at the claimed invention before the effective filling date of the instant application based on the teachings from Atau, Hoffmann and Stolle.
Claim 1, 14 and 17-18 are obvious because one of ordinary skill seeking methyl magnesium iodide for trimethyl gallium preparation is motivated to modify the Atau method by conducting the reaction under milling of the reaction mixture by a reaction mill, thus arrive at a method meeting each and every limitation of claims 1, 14, 17-18, therefore, claims 1, 14 and 17-18 also obvious.
One of ordinary skill has a motivation to do so with a reasonable expectation of success because Hoffmann teaches that a reaction mill for the heterogeneous liquid/solid reaction can permanent removal of inert surface layers, generation of new surface, and mechanical activation of the solid surface; so that can speed up the reaction.
Claim 19 is also obvious because one of ordinary skill is also motivated to use a ball mill as the reaction mill with a reasonable expectation of success because Stolle teaches that ball mill has been used as a reactor for synthesis of various organic chemicals by mechanical activation of solid or solidified reactants.
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to FRANK S. HOU whose telephone number is (571)272-1802. The examiner can normally be reached 6:30 am-2:30 pm Eastern on Monday to Friday.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached on (571)2705241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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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.
