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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination 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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 June 16, 2026 has been entered.
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.
Claim(s) 1-15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kolomeyer et al. (US 2003/0065230).
The claims are drawn to a catalyst system comprising (a), a salt of formula XY, wherein X is Zn and/or Co, and Y is an anion selected from laurate, palmitate, stearate, picolinate, glycinate, gluconate, naphthenate, 2-hexyldecanoate, 2- octyldodecanoate, cyclohexane butyrate, and mixtures thereof, and (b), at least one aminophenol, wherein the catalyst system includes components (a) and (b) in a weight ratio of from about 10,000:1 to about 10:1. The claims are also drawn to a method for rearrangement of epoxides into allyl alcohols, and subsequent Oppenauer oxidation to produce an alpha, beta-unsaturated ketone.
Kolomeyer et al. teach a catalyst system and process for rearrangement of epoxides to allylic alcohols. Suitable homogeneous organic and complex catalysts include, inter alia, zinc stearate, and cobalt naphthenate (0035). An activator/modifier may also be used along with the catalyst, and includes, inter alia, aminophenols (0029,0040). For certain epoxide rearrangements, the preferred concentration of catalyst and activator/modifier is 0.05-10% and 0.025-10% by weight, based on the amount of epoxide (0044). The components of the catalyst system can be added to the epoxide separately, in any sequence, or the catalyst system can be pre-blended prior to introduction into the reaction mixture (0042).
According to Kolomeyer et al., a wide variety of epoxides can be converted to allylic alcohols. For example, 1,2-limonene oxide may be converted into carveol (allylic alcohol), and further, carvone (alpha, beta-unsaturated ketone) by Oppenauer oxidation of the allylic alcohol. If desired, the catalyst can be removed, e.g., by filtration, washing, extraction, distillation, etc., and the product, allylic alcohol may be isolated and purified, e.g., by distillation, crystallization, etc., prior to any subsequent reaction of the allylic alcohol (0047, 0051, 0054).
When the process includes the Oppenauer oxidation, the presence of a hydrogen acceptor (consumption agent) may be needed. This hydrogen acceptor is an auxiliary carbonyl compound, e.g., cyclohexanone, 2-ethylhexanal, dihydrocarvone, benzaldehyde, furfural, and the like (0055-0056).
As an example, 1,2-limonene oxide, the catalyst, and activator/modifier are heated to reflux (200 to 230°C); water is removed, and carveol is produced. For producing the unsaturated ketone, i.e., carvone, a hydrogen acceptor, e.g., cyclohexanone, is added and the reaction mixture is held at reflux (195 to 200°C) for about 2 hours, then cooled to 120°C. A mixture of cyclohexanone and cyclohexanol that is produced is removed under vacuum. After the oxidation step is completed the conversion of carveol to carvone was above 95% yield (examples 1-47; example 57).
The reference does not expressly teach an example, wherein a catalyst comprising zinc and/or cobalt, and the anions recited in the instant claims, and an aminophenol are used in a process for rearranging an epoxide. Also, the reference does not expressly teach that the catalyst system includes components (a) and (b) in a weight ratio from about 10,000: 1 to about 10:1, as recited by the amended claims. However, as stated above, zinc stearate and cobalt naphthenate are examples of catalysts that are suitable for the rearrangement reaction taught by Kolomeyer et al., as well as an aminophenol, specifically, 2-aminophenol as activator/modifier. Kolomeyer et al. further teach that by choosing an appropriate combination of primary catalyst and activator/modifier, high regioselectivity can be achieved (0053). Moreover, the reference teaches that the preferred concentration of catalyst and activator/modifier is 0.05-10% and 0.025-10% by weight, based on the amount of epoxide reference, and teaches that the amount of phenol activator/modifier employed is selected to provide the desired activation/selectivity function.
The instant claims are therefore obvious in view of Kolomeyer et al., since the catalyst system recited by the instant claims can be afforded by Kolomeyer et al., by a person having ordinary skill in the art experimenting with different combinations of primary catalyst and activator/modifier, in an effort to finding a combination that affords optimal results, in this case, high regioselectivity of the allylic alcohol produced, and improved activity and/or selectivity of the primary catalyst in the rearrangement of the desired starting material.
Allowable Subject Matter
The following is a statement of reasons for the indication of allowable subject matter: claim 16 is drawn to zinc complexes not taught by prior art.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SIKARL A WITHERSPOON whose telephone number is (571)272-0649. The examiner can normally be reached M-F 9am-9pm IFP.
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, Scarlett Goon can be reached at 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.
/SIKARL A WITHERSPOON/ Primary Examiner, Art Unit 1692
Prosecution Insights