Prosecution Insights
Last updated: April 19, 2026
Application No. 18/009,316

Process for the Efficient Preparation of (Bio)-Alkanediols

Non-Final OA §103
Filed
Dec 08, 2022
Examiner
BAHTA, MEDHANIT W
Art Unit
1692
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Symrise AG
OA Round
1 (Non-Final)
80%
Grant Probability
Favorable
1-2
OA Rounds
2y 2m
To Grant
99%
With Interview

Examiner Intelligence

Grants 80% — above average
80%
Career Allow Rate
613 granted / 763 resolved
+20.3% vs TC avg
Strong +29% interview lift
Without
With
+28.6%
Interview Lift
resolved cases with interview
Typical timeline
2y 2m
Avg Prosecution
55 currently pending
Career history
818
Total Applications
across all art units

Statute-Specific Performance

§101
0.5%
-39.5% vs TC avg
§103
35.8%
-4.2% vs TC avg
§102
18.2%
-21.8% vs TC avg
§112
30.3%
-9.7% vs TC avg
Black line = Tech Center average estimate • Based on career data from 763 resolved cases

Office Action

§103
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 of Group I, claims 1-11 and 21-22 in the reply filed on 10/09/2025 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)). Note: “Group IV” was inadvertently included on page 5 of the Restriction/Election requirement mailed on 06/09/2025 and should be disregarded . Claims 12-16, 18 and 20 are withdrawn by the examiner from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. 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. Claims 1 , 3- 11 and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2003/0065233A1 (US’233) in v iew of Patent number CA1177095A (CA’095) . Regarding claim s 1 (a)-(b) , 3 , 5 and 21(a)-(b) , US’233 teaches a production process for α-olefins and internal olefin isomers from a primary alcohol or an ether of formula (I) and a catalyst : Examples of the straight or branched alkyl group having 3 to 20 carbon atoms as represented by R 1 in the above formula include n-propyl, n-butyl, isobutyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, tetradecyl, hexadecyl and octadecyl. Examples of the straight or branched alkyl group having 1 to 20 carbons as represented by R 2 include methyl, ethyl, n-propyl, n-butyl, isobutyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, tetradecyl, hexadecyl and octadecyl and e xamples of the primary alcohol include n-butanol, n-pentanol, 3-methyl-1-butanol, n-hexanol, n-octanol, n-nonanol, n-decanol, n-undecanol, n-dodecanol, n-tetradecanol and n-hexadecanol. Of these, n-hexanol, n-octanol, n-nonanol and n-decanol are preferred. Examples of the ether include methyl pentyl ether, hexyl methyl ether, methyl octy ether, methyl nonyl ether, decyl methyl ether, ethyl pentyl ether, ethyl hexyl ether, ethyl octyl ether, methyl nonyl ether, decyl methyl ether, isopropyl pentyl ether, hexyl isopropyl ether, isopropyl octyl ether, isopropyl nonyl ether, decyl isopropyl ether, dihexyl ether, dioctyl ether and didecyl ether ([0024]-[0025]) . The reaction in US’233 is preferably carried out at a temperature of 150 to 350° C. and more preferably at 200 to 320° C ([0030]). The reference further teaches that unreacted primary alcohol or ether, is separated and collected from reaction products, and at least part of the collected ether intermediate, and unreacted primary alcohol or ether is returned to the reaction system and can serve as a starting material for the reaction ( [0014], [0017] and [0051] ) . Regarding claim 5, the catalyst comprises γ-alumina ([0026] and Examples 1-11). Regarding claim 6-7 and 9, US’233 teaches that t he rate at which the mixture is fed to the reactor is typically in the range of 0.1 to 50 hr −1 , and preferably in the range of 0.5 to 10 hr −1 as measured in the liquid hourly space velocity (LHSV) ([0031]) and that the reaction m ay be carried out by using any known technique, including batch reaction process and continuous reaction process , in which, continuous reaction process using a fixed bed reactor is preferred ([0029]). Regarding claim 8, while US’233 teaches that unreacted alcohol and ether can be returned and serve as a starting material, the reference fails to specifically teach that the dialkylether and/or 1-alcohol are combined with fresh 1-alcohol and/or fresh dialkylether, in a ratio of 95:5 to 5:95 weight. However, since the reference teaches that the α-olefins and internal olefin isomers can be obtained from fresh primary alcohol and ether and/or from unreacted primary alcohol and ether, any combination of the fresh primary alcohol and ether and unreacted primary alcohol and ether, including the claimed ratio, would yield nothing more than the predictable α-olefins and internal olefin isomers. Regarding claim 10, US’233 teaches the obtained reaction mixture is subjected to simple distillation process to separate the intended α-olefin and other olefins including internal olefins ([0033]). Regarding claims 1(c) and 21(c), US’233 fails to teach reacting the at least one alkene of step b) to obtain a product comprising at least one alkanediol having 5 to 15 carbon atoms. The deficiency is however cured by CA’095 . Regarding claims 1(c), 11 and 21(c), CA’095 teaches a process for producing vicinal diols by the reaction of olefinically unsaturated compounds containing 4 to 36 carbon atoms with hydrogen peroxide and formic acid followed by hydrolysis with a solution of caustic soda. The reference further teaches that the process may be applied with approximately equal results to linear olefins having terminal (also known as α-olefins ) or internal double bonds and to cyclic olefins (pg.1,ln.31-pg.2,ln.1). It is known to a skilled artisan that vicinal diols have various applications in the chemical industry, and thus a skilled artisan would have been motivated in subjecting the α-olefins and the internal olefin isomers of US’233 to the reaction methods of CA’095 with a reasonable expectation of success in obtaining vicinal alkanediols. It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to a process for the preparation of alkanediols having 5 to 15 carbon atoms comprising the following steps: a) providing a 1-alcohol having 5 to 15 carbon atoms and/or a dialkylether having 10 to 30 carbon atoms and a catalyst; b) dehydrating the 1-alcohol and/or cleaving the dialkylether in a reaction chamber to obtain at least one alkene having 5 to 15 carbon atoms, wherein the at least one alkene having 5 to 15 carbon atoms is at least one olefin selected from the group consisting of: α-, β- and/or γ-olefins; wherein the dehydration and/or cleavage is performed with recirculation of dialkylether and/or 1-alcohol; and wherein the dehydration and/or cleavage is performed at a temperature ranging from 255° C. to 290° C.; and c) reacting the at least one alkene of step b) to obtain a product comprising at least one alkanediol having 5 to 15 carbon atoms in view of the combination of US’233 and CA’095. Claim 2 is rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2003/0065233A1 (US’233) in view of Patent number CA1177095A (CA’095) as applied to claims 1, 3-11 and 21 above, and further in view of Patent number US11 , 4143 , 65 (US 365 ). The teachings of US’233 and CA’095 has been set forth above. Regarding claim 2, CA’095 fails to specifically teach that the product comprises at least two alkanediols selected from the group consisting of: a 1,2-alkanediol, a 2,3-alkanediol and a 3,4-alkanediol, each independently having 5 to 15 carbon atoms; wherein in the product, the ratio of the 1,2-alkanediol to the 2,3-alkanediol is in the range of 90:10 to 99.9:0.1 and/or the ratio of the 1,2-alkanediol to the 3,4-alkanediol is in the range of 90:10 to 99.99:0.01 by weight. However, since the reference teaches that the reaction process can be applicable to either the terminal olefins or internal olefins, subjecting any combination of the terminal olefins and internal olefins, such as 2,3-olefins or 3,4-olefins, would yield nothing more than the predictable product comprising at least two alkanediols selected from the group consisting of: a 1,2-alkanediol, a 2,3-alkanediol and a 3,4-alkanediol. CA’095 teaches the desired diols can usually be obtained in reaction times of less than seven hours and in yields of approximately 90%. Furthermore, US’365 teaches a composition comprising about 60% to about 99% of a bio-1,2-alkanediol having a carbon chain length of 7 to 20 carbon atoms and less than 20% of a corresponding bio-2,3-alkanediol having the same carbon chain length as the bio-1,2-alkanediol , which is equivalent to a ratio of bio-1,2-alkanediol to bio-2,3-alkanediol of 3:1 to 4.95:1. The reference teaches that the composition is used as a preservative composition . Thus based on th e general yield of diols taught by CA’095 , it would be within the purview of a skilled artisan to determine, through routine experimentation, the amount needed for terminal olefins and 2,3-olefins to give a product composition of US’365 that comprises about 60% to about 99% of a bio-1,2-alkanediol having a carbon chain length of 7 to 20 carbon atoms and less than 20% of a corresponding bio-2,3-alkanediol having the same carbon chain length as the bio-1,2-alkanediol . It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to a process for the preparation of alkanediols having 5 to 15 carbon atoms comprising the following steps: a) providing a 1-alcohol having 5 to 15 carbon atoms and/or a dialkylether having 10 to 30 carbon atoms and a catalyst; b) dehydrating the 1-alcohol and/or cleaving the dialkylether in a reaction chamber to obtain at least one alkene having 5 to 15 carbon atoms, wherein the at least one alkene having 5 to 15 carbon atoms is at least one olefin selected from the group consisting of: α-, β- and/or γ-olefins; wherein the dehydration and/or cleavage is performed with recirculation of dialkylether and/or 1-alcohol; and wherein the dehydration and/or cleavage is performed at a temperature ranging from 255° C. to 290° C.; and c) reacting the at least one alkene of step b) to obtain a product comprising at least one alkanediol having 5 to 15 carbon atoms , wherein in step c) a product is obtained comprising at least two alkanediols selected from the group consisting of: a 1,2-alkanediol, a 2,3-alkanediol and a 3,4-alkanediol, each independently having 5 to 15 carbon atoms; wherein in the product, the ratio of the 1,2-alkanediol to the 2,3-alkanediol is in the range of 90:10 to 99.9:0.1 and/or the ratio of the 1,2-alkanediol to the 3,4-alkanediol is in the range of 90:10 to 99.99:0.01 by weight in view of the combination of US’233 , CA’095 and US’365 . Claim 22 is rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2003/0065233A1 (US’233) in view of Patent number CA1177095A (CA’095) as applied to claim s 1, 3-11 and 21 above, and further in view of Patent application publication number US2016/0206571A1 (US’571) . The teachings of US’233 and CA’095 has been set forth above. Regarding claim 22, CA’095 does not specifically teach that the product obtained comprises at least two 1,2-alkanediols differing in their chain length. However, the reference teaches the process is particularly suitable for the hydroxylation of long-chain linear olefins containing 4 to 36 carbon atoms and a terminal or internal double bond. Furthermore, US’571 teaches a composition comprising 1,2-alkanediols differing in their chain length , i.e. a mixture of 1,2-hexanediol and 1,2-octanediol, wherein the composition is used as active mixture in cosmetic, pharmaceutical or dermatological emulsions . Thus, a skilled artisan would have been motivated to combine two terminal alkenes with 6 and 8 carbon numbers and subject the mixture to the reaction process of CA’095 with a reasonable expectation of success in obtaining a combination of 1,2-hexanediol and 1,2-octanediol that can be used as active mixture in cosmetic, pharmaceutical or dermatological emulsions . It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to a process for the preparation of alkanediols having 5 to 15 carbon atoms comprising the following steps: a) providing at least one 1-alcohol having 5 to 15 carbon atoms, and/or at least one dialkylether having 10 to 30 carbon atoms and a catalyst; b) dehydrating the at least one 1-alcohol and/or cleaving the at least one dialkylether to obtain at least one alkene having 5 to 15 carbon atoms, wherein the at least one alkene having 5 to 15 carbon atoms is at least one olefin selected from the group consisting of: α-, β- and/or γ-olefins, each independently having 5 to 15 carbon atoms; wherein the dehydration and/or cleavage is performed with recirculation of dialkylether and/or 1-alcohol; and wherein the dehydration and/or cleavage is performed at a temperature ranging from 255° C. to 290° C.; and c) reacting the at least one alkene of step b) to obtain a product comprising at least one alkanediol having 5 to 15 carbon atoms ; and wherein in step c) the product obtained comprises at least two 1,2-alkanediols differing in their chain length and/or wherein the product comprises at least two 2,3-alkanediols differing in their chain length, and wherein said alkanediols each independently have from 5 to 15 carbon atoms in view of the combination of US’233 , CA’095 and US’571 . Citation of Relevant Prior Art The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Patent number GB2145076A (GB’076) teaches Thus, the process of the instant claims 1 and 21 are obvious over the combination of US’233 (cited above) and GB’076. Conclusion Claims 1-11 and 21-22 are rejected and no claims are allowed. Any inquiry concerning this communication or earlier communications from the examiner should be directed to FILLIN "Examiner name" \* MERGEFORMAT MEDHANIT W BAHTA whose telephone number is FILLIN "Phone number" \* MERGEFORMAT (571)270-7658 . The examiner can normally be reached FILLIN "Work Schedule?" \* MERGEFORMAT Monday-Friday 8am-5pm . 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, FILLIN "SPE Name?" \* MERGEFORMAT Scarlett Goon can be reached at FILLIN "SPE Phone?" \* MERGEFORMAT 571-270-5241 . 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. /MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692
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Prosecution Timeline

Dec 08, 2022
Application Filed
Dec 17, 2025
Non-Final Rejection — §103 (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

1-2
Expected OA Rounds
80%
Grant Probability
99%
With Interview (+28.6%)
2y 2m
Median Time to Grant
Low
PTA Risk
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