Prosecution Insights
Last updated: July 17, 2026
Application No. 19/094,226

PROCESS FOR THE MANUFACTURE OF NONAFLUORO-TERT-BUTYL ALCOHOL BY ELECTROFLUORINATION (ECF)

Non-Final OA §112
Filed
Mar 28, 2025
Priority
Oct 05, 2022 — DE 10 2022 125 687.1 +1 more
Examiner
WONG, EDNA
Art Unit
1795
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Fluorinnovation L L C-Fz
OA Round
1 (Non-Final)
58%
Grant Probability
Moderate
1-2
OA Rounds
1y 9m
Est. Remaining
40%
With Interview

Examiner Intelligence

Grants 58% of resolved cases
58%
Career Allowance Rate
615 granted / 1051 resolved
-6.5% vs TC avg
Minimal -19% lift
Without
With
+-18.9%
Interview Lift
resolved cases with interview
Typical timeline
3y 1m
Avg Prosecution
44 currently pending
Career history
1087
Total Applications
across all art units

Statute-Specific Performance

§103
78.9%
+38.9% vs TC avg
§102
0.5%
-39.5% vs TC avg
§112
19.4%
-20.6% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1051 resolved cases

Office Action

§112
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 with traverse of Group I, claims 1-10 and 15-18, in the reply filed on April 27, 2026 is acknowledged. The traversal is on the ground(s) that the features of R denotes a substituent selected from the group consisting of CF3CO-, CF2HCO-, CFH2CO-, CF2ClCO-, CFCl2CO-, CCl3CO-, CClH2CO-, CCl2HCO-, CF2ClSO2-, CFCl2SO2-, CCl3SO2-, CF2HSO2-, CFH2SO2-, CH3SO2-, and PfSO2- and electrofluorination are common to all the claims. This is not found persuasive because neither the process of claim 1 nor the process of claim 20 is required to use the reaction mixture of claim 19. The requirement is still deemed proper and is therefore made FINAL. Accordingly, claim 11-14 (species), 19 (composition) and 20 (process) are withdrawn from consideration as being directed to a non-elected invention. Drawings The drawings were received on March 28, 2025. These drawings are acceptable. Claim Objections Claims 1, 6, and 15-17 are objected to because of the following informalities: Claim 1 line 8, please maned the word “method” to the word -- process --. This is an instance where the article should be changed to ensure proper antecedent basis for the claim terminology. line 12, please amend the word “a” to the word -- the --. Claim 6 line 2, please amend the word “a” to the word -- the --. Claim 14 (withdrawn)1 line 1, please insert the word -- step -- after the word “electrofluorination”. Claim 15 line 2, please insert the word -- step -- after the word “electrofluorination”. Claim 16 line 2, please insert the word -- step -- after the word “electrofluorination”. Claim 17 line 1, please insert the word -- step -- after the word “electrofluorination”. Claim 20 (withdrawn) line 7, please amend “a hydroxyl group protecting agent R-X of formula (IV)” to -- “a hydroxyl group protecting agent of formula (IV), R-X (IV) --. line 17, please insert the phrase -- wherein R has a same meaning as above -- after “ PNG media_image1.png 128 206 media_image1.png Greyscale ”. Formula (II) is missing the definition of R. line 21, please insert the phrase -- wherein R has a same meaning as above -- after “ PNG media_image2.png 129 196 media_image2.png Greyscale ”, Formula (I) is missing the definition of R. line 18, please amend the word “a” to the word -- the --. Appropriate correction is required. Claim Rejections - 35 USC § 112 Claims 2-5, 10 and 18 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. Claim 2 lines 3-4, “the isolated and/or purified hydroxyl group protected nonafluoro-tert-butyl alcohol ester compound of formula (I)” lacks antecedent basis. Antecedent basis must be laid for each recited element in a claim, typically, by introducing each element with the indefinite article (“a” or “an”). See Slimfold Mfg. Co. v. Kincaid Properties, Inc., 626 F. Supp 493, 495 (N.D. Ga. 1985), aff'd, 810 F.2d 1113 (Fed. Cir. 1987) (citing P. Rosenberg, 2 Patent Law Fundamentals § 14.06 (2d. Ed. 1984)). Subsequent mention of an element is to be modified by the definite article “the”, “said” or “the said,” thereby making the latter mention(s) of the element unequivocally referable to its earlier recitation. Claim 3 lines 9-13, recite “wherein the hydroxyl group protected nonafluoro-tert-butyl alcohol ester compound of formula (I) is prepared in a protecting reaction step by reacting a tert-butyl alcohol compound of formula (III), PNG media_image3.png 129 202 media_image3.png Greyscale with a hydroxyl group protecting agent of formula R-X (IV), wherein R has a same meaning as above, and X denotes a hydrogen atom, a halogen atom, or an -O-R group, each respective R being selected independently, to obtain the hydroxyl group protected tert-butyl alcohol compound of formula (II)”. It is unclear from the claim language how the reacting of formula (III) prepares formula (I) and obtains formula (II). Claim 5 line 3, “the hydroxyl group protecting group R” lacks antecedent basis. Antecedent basis must be laid for each recited element in a claim, typically, by introducing each element with the indefinite article (“a” or “an”). See Slimfold Mfg. Co. v. Kincaid Properties, Inc., 626 F. Supp 493, 495 (N.D. Ga. 1985), aff'd, 810 F.2d 1113 (Fed. Cir. 1987) (citing P. Rosenberg, 2 Patent Law Fundamentals § 14.06 (2d. Ed. 1984)). Subsequent mention of an element is to be modified by the definite article “the”, “said” or “the said,” thereby making the latter mention(s) of the element unequivocally referable to its earlier recitation. Claim 10 line 4, the “starting material” lacks antecedent basis. Claim 12 (withdrawn) line 2, “the anode/cathode mix” lacks antecedent basis. Antecedent basis must be laid for each recited element in a claim, typically, by introducing each element with the indefinite article (“a” or “an”). See Slimfold Mfg. Co. v. Kincaid Properties, Inc., 626 F. Supp 493, 495 (N.D. Ga. 1985), aff'd, 810 F.2d 1113 (Fed. Cir. 1987) (citing P. Rosenberg, 2 Patent Law Fundamentals § 14.06 (2d. Ed. 1984)). Subsequent mention of an element is to be modified by the definite article “the”, “said” or “the said,” thereby making the latter mention(s) of the element unequivocally referable to its earlier recitation. See also claim 13, lines 1-2. line 4, “the continuous one time pass-by electrofluorination” lacks antecedent basis. Antecedent basis must be laid for each recited element in a claim, typically, by introducing each element with the indefinite article (“a” or “an”). See Slimfold Mfg. Co. v. Kincaid Properties, Inc., 626 F. Supp 493, 495 (N.D. Ga. 1985), aff'd, 810 F.2d 1113 (Fed. Cir. 1987) (citing P. Rosenberg, 2 Patent Law Fundamentals § 14.06 (2d. Ed. 1984)). Subsequent mention of an element is to be modified by the definite article “the”, “said” or “the said,” thereby making the latter mention(s) of the element unequivocally referable to its earlier recitation. line 4, the “starting material” lacks antecedent basis. line 5, “the anode/cathode mix of electrodes” lacks antecedent basis. Antecedent basis must be laid for each recited element in a claim, typically, by introducing each element with the indefinite article (“a” or “an”). See Slimfold Mfg. Co. v. Kincaid Properties, Inc., 626 F. Supp 493, 495 (N.D. Ga. 1985), aff'd, 810 F.2d 1113 (Fed. Cir. 1987) (citing P. Rosenberg, 2 Patent Law Fundamentals § 14.06 (2d. Ed. 1984)). Subsequent mention of an element is to be modified by the definite article “the”, “said” or “the said,” thereby making the latter mention(s) of the element unequivocally referable to its earlier recitation. Claim 18 lines 1-2, recite “wherein deprotecting is performed by saponification with an aqueous inorganic base”. It is unclear from the claim language how this limitation is further limiting the process. This step is floating in the process with no connection with any of the elements recited in claim 1. Claim 20 (withdrawn) line 16, recites “a nonafluoro-tert-butyl alcohol ester compound of formula (II)”. Formula (II) does not have any “nonafluoro” in the tert-butyl. line 18, “the hydroxyl group protected tert-butyl alcohol compound of formula (II)” lacks antecedent basis. Antecedent basis must be laid for each recited element in a claim, typically, by introducing each element with the indefinite article (“a” or “an”). See Slimfold Mfg. Co. v. Kincaid Properties, Inc., 626 F. Supp 493, 495 (N.D. Ga. 1985), aff'd, 810 F.2d 1113 (Fed. Cir. 1987) (citing P. Rosenberg, 2 Patent Law Fundamentals § 14.06 (2d. Ed. 1984)). Subsequent mention of an element is to be modified by the definite article “the”, “said” or “the said,” thereby making the latter mention(s) of the element unequivocally referable to its earlier recitation. line 23, “the hydroxyl group protecting group R” lacks antecedent basis. Antecedent basis must be laid for each recited element in a claim, typically, by introducing each element with the indefinite article (“a” or “an”). See Slimfold Mfg. Co. v. Kincaid Properties, Inc., 626 F. Supp 493, 495 (N.D. Ga. 1985), aff'd, 810 F.2d 1113 (Fed. Cir. 1987) (citing P. Rosenberg, 2 Patent Law Fundamentals § 14.06 (2d. Ed. 1984)). Subsequent mention of an element is to be modified by the definite article “the”, “said” or “the said,” thereby making the latter mention(s) of the element unequivocally referable to its earlier recitation. Allowable Subject Matter The following is a statement of reasons for the indication of allowable subject matter: Claims 1-10 and 15-18 define over the prior art of record because the prior art does not contain any language that teaches or suggests a process for the manufacture of a hydroxyl group protected nonafluoro-tert-butyl alcohol ester compound of formula (I), PNG media_image4.png 129 202 media_image4.png Greyscale wherein R denotes a substituent selected from the group consisting of CF3CO-, CF2HCO-, CFH2CO-, CF2ClCO-, CFCl2CO-, CCl3CO-, CClH2CO-, CCl2HCO-, CF2ClSO2-, CFCl2SO2-, CCl3SO2-, CFH2SO2-, CF2HSO2-, CFH2SO2-, CH3SO2-, and PfSO2-, and wherein Pf denotes a partially or perfluorinated C2-C4 residue comprising the step of reacting as presently claimed. Therefore, a person skilled in the art would not have been motivated to adopt the above conditions, and a prima facie case of obviousness cannot be established. Childs et al. (US Patent No. 3,900,372) teaches primary or secondary alkanols (col. 1, lines 56-57). Aust et al. (US Patent Application Publication No. 2012/0152757 A1) does not teach reacting a hydroxyl group protected tert-butyl alcohol compound of formula (II), PNG media_image5.png 135 202 media_image5.png Greyscale wherein R has a same meaning as above, in an electrofluorination step in a presence of anhydrous hydrogen fluoride to obtain the hydroxyl group protected nonafluoro-tert-butyl alcohol ester compound of formula (I). Claims 1, 6, and 15-17 would be allowable if rewritten or amended to overcome the claim objection(s) set forth in this Office action. Claims 2-5, 10 and 18 would be allowable if rewritten or amended to overcome the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), 2nd paragraph, set forth in this Office action. Citations The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Kisukuri et al. (“Electrochemical Installation of CFH2−, CF2H−, CF3−, and Perfluoroalkyl Groups into Small Organic Molecules,” The Chemical Record (2021 Sep), Vol. 21, No. 9, pp. 2502-2525) is cited to teach flow setups (page 2522, Schemes 46 and 47). Any inquiry concerning this communication or earlier communications from the examiner should be directed to EDNA WONG whose telephone number is (571) 272-1349. The examiner can normally be reached Monday-Friday, 7:00 AM- 3:30 PM. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Luan Van can be reached at (571) 272-8521. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /EDNA WONG/Primary Examiner, Art Unit 1795 1 Claims 11-14 (species) and 20 (process) would be subjected to rejoinder.
Read full office action

Prosecution Timeline

Mar 28, 2025
Application Filed
May 21, 2026
Non-Final Rejection mailed — §112
Jul 09, 2026
Response Filed

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Prosecution Projections

1-2
Expected OA Rounds
58%
Grant Probability
40%
With Interview (-18.9%)
3y 1m (~1y 9m remaining)
Median Time to Grant
Low
PTA Risk
Based on 1051 resolved cases by this examiner. Grant probability derived from career allowance rate.

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