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 .
The examiner has considered the amendment and response filed by applicants on February 11, 2026. The amendment was effective in overcoming the rejection of record under 35 U.S.C. 102; however, the following rejection is being maintained.
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. 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 by 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. 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). 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.
Response to Arguments
Applicant's arguments filed February 11, 2026 have been fully considered but they are not persuasive. Applicants argue that Kolomeyer et al. teach cobalt naphthenate and zinc stearate, as well as aminophenols, for a catalyst system, but not as a specific combination as recited in the claims. According to applicants, a person of skill in the art would have no reason or motivation to make the substitutions necessary to arrive at the claimed invention.
The examiner respectfully disagrees with applicant’s argument. As applicant acknowledges, the reference teaches cobalt naphthenate and zinc stearate, as well as aminophenols, for a catalyst system. As stated by the examiner in the rejection above, the reference teaches that by choosing an appropriate combination of primary catalyst and activator/modifier, high regioselectivity can be achieved. A person having ordinary skill would therefore be motived to experiment 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.
Moreover, the examples taught by Kolomeyer et al. include zinc and cobalt cations with a 2-aminophenol activator/modifier. It would be obvious to substitute one anion for another to observe how the regioselectivity of the product is modified.
The examiner therefore finds that the rejection is proper.
THIS ACTION IS MADE FINAL. 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 SIKARL A WITHERSPOON whose telephone number is (571)272-0649. The examiner can normally be reached M-F 9am-9pm IFP.
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/SIKARL A WITHERSPOON/Primary Examiner, Art Unit 1692