Patent Application 18220704 - MONOALKYLATION OF CYCLOPENTADIENE - Rejection

Patent Application 18220704 - MONOALKYLATION OF CYCLOPENTADIENE

Title: MONOALKYLATION OF CYCLOPENTADIENE

Application Information

• Invention Title: MONOALKYLATION OF CYCLOPENTADIENE
• Application Number: 18220704
• Submission Date: 2025-05-12T00:00:00.000Z
• Effective Filing Date: 2023-07-11T00:00:00.000Z
• Filing Date: 2023-07-11T00:00:00.000Z
• National Class: 585
• National Sub-Class: 353000
• Examiner Employee Number: 73604
• Art Unit: 1772
• Tech Center: 1700

Rejection Summary

• 102 Rejections: 0
• 103 Rejections: 1

Cited Patents

The following patents were cited in the rejection:

• US 0085289🔗

Office Action Text

    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 .

Election/Restrictions
Applicant’s election without traverse of Formula A (claims 1-12) in the reply filed on 02/10/2025 is acknowledged. 
The remarks “Applicants make this election with the understanding that upon allowance of a generic claim, applicant will be entitled to additional species which depend from or otherwise require all of the limitations of an allowable generic claim as provided by 37 CFR 1.141” is noted. However, Formula A and formula B are different compounds and there is no generic claim.

Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.

The following is a quotation of the first paragraph of pre-AIA  35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.

Claims 1-12 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for specific agents such as as recited in claim 4, does not reasonably provide enablement for unspecified agents.  The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to use the invention commensurate in scope with these claims.

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.
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.
Claim(s) 1-12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Harlan et al (2013/0085289 A1) in view of Shimizu (the English translation of JP 2003-055272 A).
Harlan discloses a process of synthesis of an alkyl cyclopentadiene such as CpC5H11 by contacting at least cyclopentadienyl anion source such as Cp2Mg (magnesocene) (A) with an alkyl halides RX to form alkyl cyclopentadiene (the abstract; 0012, 0017-0019).
Harlan discloses the components of the reaction can be present in a suitable solvent such as THF (0020).
Harlan discloses in examples, a solution of a THF and cyclopentadienyl anion source is prepared before the alkylating agent RX is added for the reaction (0048).
Harlan does not add an modifying agent such as DMSO into the solution of dicyclopentadiene and THF as recited in claims 4 and claim 5. However, Shimizu discloses a process of making alkyl cyclopentadiene by generating an cyclopentadienyl anion in the presence of electrophile such as an alkyl halide. The anion is generated by adding a base such as Grignard agent into an solution such as THF and dimethyl sulfoxide (claims; 0003; 0018-0024).
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the Harlan process by using a solution containing both THF and DMSO as disclosed by Shimizu for reaction since as disclosed by Shimizu that the substituted cyclopentadiene can be produced on industrial scale with high selectivity and convenience (see the Summary of The Invention).
Regarding claims 2 and 3, the contents of dialkylated compounds and the conversion of dicyclopentadiene magnesium are inherent results of the process of Harlan modified by Shimizu.
The limitation of claims 6-8 can be found in 0017 of Harlan.
 The limitation of claim 9 can be found in 0019 of Harlan.
Regarding claims 10-12, the content of the modifying agent namely DMSO in the reaction mixture must be selected to operate the process.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to have modified the Harlan process modified by Shimizu by selecting appropriate amount of DMSO to arrive at the applicants’ claimed process since the amounts of the components are reaction parameters which one having ordinary skill in the art know to select to operate the process.

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/THUAN D DANG/Primary Examiner, Art Unit 1772