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 .
Status of the Claims
Claims 1-6, 8-10, and 12-21 are pending.
Claims 1, 8, and 15 are amended.
Claims 18-21 are new.
Claims 7 and 11 are cancelled.
Response to Amendments
Applicant’s amendments filed 10 October 2025 are acknowledged.
Claim Rejections - 35 USC § 103
Applicant’s amendment to claims 1 and 15 and cancellation of claim 7 are sufficient to overcome the rejection of claims 1-10 and 12-17 under 35 U.S.C. 103 as being unpatentable over Van Hal et al. (WO2014137212, hereinafter Van Hal) in view of Miller et al. (WO1991004242, hereinafter Miller). Due to the amendment to claims 1 and 15 and the cancellation of claim 7 the rejection is withdrawn and a new ground(s) of rejection is/are provided below.
Response to Arguments
Applicant’s arguments filed 10 October 2025 have been fully considered but they are not persuasive.
Applicant’s argue that Van Hal and Miller do not disclose the limitations as recited in amended claims 1 and 15. These arguments have been considered but are not persuasive for the reasons set forth in the new grounds of rejection below and the response to arguments below.
In response to applicant’s arguments throughout the remarks filed on 10 October 2025 that the references fail to show certain features of the invention, it is noted that the features upon which applicant relies (i.e., a “liquid-phase reaction” or “a gas-phase reaction”) are not currently claimed. The current claims make no mention of a solvent for a liquid-phase reaction or a gas for a gas-phase reaction. Since the temperature of the reaction is not currently claimed, a person of ordinary skill in the art would interpret the raw material alcohol having 8 or more and 22 or less carbon atoms may be in a liquid or a gas form depending upon the temperature of the reaction.
In response to applicant’s arguments on page 7 of the remarks filed on 10 October 2025 that “a skilled artisan would have had absolutely no motivation to combine Van Hal's gas phase reaction with Miller's liquid phase reaction base and/or to modify Van Hal's gas phase reaction by employing Miller's liquid phase reaction base” and “the skilled artisan would not have expected that combining Van Hal's gas phase with Miller's liquid phase Guerbet base would yield a suitable catalyst”, the test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981).
As stated above, the current claims make no mention of a liquid-phase reaction or a gas-phase reaction.
Val Hal teaches it is known in the prior art to perform Guerbet reactions in the liquid phase and the gas phase, see Para. [0031].
Miller teaches it is known in the prior art to perform Guerbet reactions in the presence of a co-catalyst including a metal catalyst and a base, see Abstract and Pg. 9, Ln. 6-Pg. 10, Ln. 5. The Miller conversion takes place at temperatures of above 180°C to about 260°C and the starting alcohols of Miller are the aliphatic, cycloaliphatic and araliphatic alcohols containing from 4 to 22 carbon atoms, see Pg. 7, Lns. 2-30. The boiling point of a C8 alcohol 1-octanol is 195° C, the boiling point of a C20 alcohol 1-eicosanol is 356° C, and the boiling point of a C22 alcohol 1-docosanol is 180° C, as evidenced by Haynes, (“CRC Handbook of Chemistry and Physics”, 2017, 97th Edition, CRC Press, Pgs. 3-236, 3-240, and 3-426). Therefore, a person of ordinary skill in the art would interpret the reaction of Miller within the preferred temperature range to be in the gas-phase or the liquid-phase depending upon the boiling point of the starting alcohol.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and both Van Hal and Miller teach it is known within the art to perform catalytic Guerbet reactions in the gas or liquid phase, a person of ordinary skill in the art has good reason to modify Van Hal in order to produce a higher alcohol from a lower alcohol by pursuing the known options within their technical grasp before the effective filing date of the claimed invention, such as adding a basic co-catalysts, as taught by Miller, for the benefit of converting an alcohol to a Guerbet alcohol with increased rates of reaction and increased yields, see Miller, Pg. 6, Lns. 3-8, Pg. 9, Ln. 30-Pg. 10, Ln. 5.
For the reasons indicated above, applications above arguments are not persuasive.
In response to applicant’s arguments on page 7 of the remarks filed on 10 October 2025 that “[a]s is evident from the above claim language, the base catalyst for the present liquid-phase reaction cannot be used directly for a gas-phase reaction.” Arguments presented by applicant cannot take the place of evidence in the record, see MPEP 2145 I.
In this case, as stated above, Miller teaches it is known within the prior art to use a base catalyst along with a metal catalyst in a gas-phase or liquid-phase reaction.
Further, Gadewar et al. (US20140235901, published 21 August 2014, hereinafter Gadewar) teaches it is known in the prior art for the production of higher alcohols from any C2-C5 alpha hydrogen alcohols to use one or more catalysts, such as a hydroxyapatite Guerbet reaction catalyst, a solid base Guerbet reaction catalyst, or a combination thereof, see Abstract; Paras. [0011];[0044]-[0047];[0163], containing carbonates, such as sodium carbonate, copper, nickel, and titanium, see Paras. [0126];[0213]-[0219], in a combined gas-phase and liquid-phase reaction, see Paras. [0011];[0046];[0053];[0057];[0131];[0184]; Fig. 10. Therefore, it is known within the prior art to operate the reaction in both liquid and gas phases with a basic Guerbet reaction catalyst; as a result, a person of ordinary skill in the art would interpret the reactions of Miller and Gadewar to contain a base catalyst in the gas-phase or the liquid-phase depending upon the boiling point of the starting alcohol.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Van Hal, Miller, and Gadewar teach it is known within the art to perform catalytic Guerbet reactions in the gas and/or liquid phase, a person of ordinary skill in the art has good reason to modify Van Hal in order to produce a higher alcohol from a lower alcohol by pursuing the known options within their technical grasp before the effective filing date of the claimed invention, such as adding a basic co-catalysts, as taught by Miller and Gadewar, for the benefit of converting an alcohol to a Guerbet alcohol with increased rates of reaction, increased yields, see Miller, Pg. 6, Lns. 3-8, Pg. 9, Ln. 30-Pg. 10, Ln. 5, lower manufacturing cost, and decreased by-products production, see Gadewar, Paras. [0034];[0126];[0160].
For the reasons indicated above, applications above arguments are not persuasive.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claims 18-21 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Regarding claims 18-21, the parenthetical renders the claims indefinite because it is unclear whether the limitations within the parenthetical are part of the claimed invention, see MPEP § 2173.05(d). The claims have been interpreted with commas instead of the parenthetical, for example in regard to claim 18, “wherein the mass ratio of the third component to the first component, ,
Claim Rejections - 35 USC § 103
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 1-6, 8-10, and 12-21 are rejected under 35 U.S.C. 103 as being unpatentable over Van Hal et al. (WO2014137212, published 12 September 2014, hereinafter Van Hal) in view of Miller et al. (WO1991004242, published 04 April 1991, hereinafter Miller) and Gadewar et al. (US20140235901, published 21 August 2014, hereinafter Gadewar).
Van Hal teaches the claims 1-6, 10, and 12-17 limitations of a catalyst for the gas phase Guerbet reaction, in particular for the Guerbet reaction of alkanol, wherein the catalyst comprises at least 20 atom% copper, based on total metal content, see Abstract, where the reaction involves contacting at least one non-tertiary alkanol containing a non-tertiary hydroxyl moiety having at least two β-hydrogen atoms with the catalyst, the non-tertiary alkanol may be represented as R1-CH2-CH(OH)-R2, wherein each of R1 and R2 are individually selected from hydrogen and alkyl, preferably C1-C20 alkyl, more preferably C1-C6 alkyl, see Para. [0029], meeting the producing and reacting raw material alcohol in claim 1, the primary aliphatic alcohol in claim 6, and the method of producing in claim 15;
The catalyst is described as having a metal oxide composition on an alumina or zeolite carrier, where the weight ratio of the metal oxide composition to carrier is preferably between 9:1 and 1:9, more preferably between 2:1 and 1:2, the metal oxide composition comprises at least 20 wt% copper oxide, more preferably between 25 wt% and 75 wt% copper oxide, even more preferably between 30 and 60, most preferably between 35 wt% and 55 wt% copper oxide, calculated as CuO, and based on total weight of the catalyst, and in a list of promoter catalytic metals applied to enhance the catalytic activity of the catalyst, the catalysts has 2.5 wt% of NiO at most based on total weight of the catalyst and 2.5 wt% TiO2 at most based on total weight of the catalyst, see Paras. [0022]-[0024], where the catalysts is preferably present in the solid phase, preferably in a catalyst bed, through which a stream comprising the reactant(s), i.e. the non-tertiary alkanols as described above flow through the catalysts bed; therefore, the catalysts bed is suspended within the reactant flow, see Para. [0032], meeting:
The catalyst metals supported on a specific carrier in claim 4 and in claim 5;
The catalysts first component is copper, second component is nickel, and third component is titanium in claim 1, in claim 2, in claim 3, in claim 15, in claim 16, and in claim 17;
Within the specific ranges of the mass of the first component, second component, and third component in claim 12, in claim 13, and in claim 14;
The suspended bed reaction in claim 9;
The copper oxide, CuO, is in the catalyst at a weight of at least 20 wt% to 75 wt%, the NiO is in the catalyst at a weight of at most 2.5 wt%, and the TiO2 is in the catalyst at a weight of at most 2.5 wt%, see Paras. [0022]-[0023], as calculated by the examiner the mass ratio of third component Ti to Cu is 0.0250 to 0.0938 and the mass ratio of second component Ni to Cu is 0.0307 to 0.1151, meeting:
Within the range of the mass ratio of the third component to the first component in claim 1 and in claim 15; and,
Within the range of the mass ratio of the second component to the first component in claim 10.
Regarding instant application claims 18-21, Van Hal teaches the oxides of copper, magnesium, aluminum, silicon and zinc together make up for at least 90 wt.% of the catalyst, and the copper oxide, CuO, is in the catalyst at a weight of at least 20 wt%, see Para. [0022]. When nickel is added as the second metal, the NiO is in the catalyst at a weight of at most 5 wt%, and the third metal may be zirconium added as ZrO2 at a weight % of the remainder of the catalysts, i.e., 5 wt%, see Paras. [0020]-[0023], as calculated by the examiner the mass ratio of 5 wt% of ZrO2/20wt% CuO yields (third component Zr 3.702/first component Cu 15.978) equals a 0.232 mass ratio and the mass ratio of second component 5 wt% of NiO/20wt% CuO yields (second component Ni 3.929/ first component to Cu 15.978) equals a 0.246 mass ratio, meeting:
Within the range of mass ratio in instant application claims 18-21.
Van Hal teaches Cu-Ni-Ti catalysts in a list of a variety of possible catalytic metals, see Paras. [0022]-[0023], the Guerbet reaction is performed in the presence of a strong base, e.g. alkali metal hydroxides or alkoxides, hydrogenation catalyst, see Para. [0002], and metal hydroxides may be used as catalysts, see Paras. [0020];[0022];[0025].
Van Hal does not teach:
The specific use of a Cu-Ni-Ti or Cu-Ni-Zr catalyst selected from within the list of possible choices;
The claim 8 limitation of wherein an amount of the base catalyst (B) based on the total amount of the raw material alcohol is 0.1% by mol or more and 7% by mol or less; and,
The claim 9 limitation of wherein an amount of the catalyst (A) based on the total amount of the raw material alcohol is 0.01% by mass or more and 10% by mass or less.
Miller relates to a Guerbet alcohol process in which a starting alcohol is condensed in the presence of a cocatalyst base to provide a Guerbet alcohol having more carbon atoms than the starting alcohol, see Abstract and Pg. 9, Lns. 6-21, where the catalyst is a cocatalyst of a base, such as potassium hydroxide, and metal complex containing metals such as Al, Ni, B, Mg, Cu, Zn, Sn, Ti, Zr, see Pg. 9, Lns. 6-21, where the selection of a Cu-Ni-Ti catalysts is limited to among eight metals, meeting the catalysts (A) in claim 1 and the catalyst in claim 15, and the amount of base, such as potassium hydroxide, is added in amounts up to 10 mole %, typically at about 5 mole % in the reaction, see Pg. 9, Ln. 22-Pg. 10, Ln. 5, meeting and within the range in claim 8, and the amount of catalysts may be employed at levels on the order of about 10-5 to 10 weight %, and preferably on the order of about 10-3 to 10-1 weight %, meeting and within the range in claim 9.
Gadewar teaches it is known in the prior art for the production of higher alcohols from any C2-C5 alpha hydrogen alcohols to use one or more catalysts, such as a hydroxyapatite Guerbet reaction catalyst, a solid base Guerbet reaction catalyst, or a combination thereof, see Abstract; Paras. [0011];[0044]-[0047];[0163], containing carbonates, such as sodium carbonate, copper, nickel, titanium, and zirconium, see Paras. [0126];[0213]-[0219], in a combined gas-phase and liquid-phase reaction, see Paras. [0011];[0046];[0053];[0057];[0131];[0184]; Fig. 10, also meeting reacting a raw material alcohol having 8 or more and 22 or less carbon atoms, in the presence of a base catalyst (B) and a catalyst (A), the catalyst (A) containing copper, nickel, and titanium in instant application claim 1 and in instant application claim 15.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified Van Hal to select a cocatalyst of a hydroxide base catalyst and a Cu-Ni-Ti or a Cu-Ni-Zr catalyst of the appropriate concentrations, as taught by Miller and Gadewar, with a reasonable predictability of success for the purpose of converting an alcohol to a Guerbet alcohol with increased rates of reaction and increased yields, see Miller, Pg. 6, Lns. 3-8 and Pg. 9, Ln. 30-Pg. 10, Ln. 5, lower manufacturing cost, and decreased by-products production, see Gadewar, Paras. [0034];[0126];[0160].
By applying “routine optimization” and “predictable results” to select the optimal catalysts and concentrations, one of ordinary skill in the art would have been motivated to make these modifications because Miller and Gadewar provide a finite number of identified, predictable solutions. A person of ordinary skill in the art has good reason to produce a Guerbet alcohol by pursuing the known options within their technical grasp for the benefit of converting an alcohol to a Guerbet alcohol with increased rates of reaction and increased yields, see Miller, Pg. 6, Lns. 3-8, Pg. 9, Ln. 30-Pg. 10, Ln. 5, lower manufacturing cost, and decreased by-products production, see Gadewar, Paras. [0034];[0126];[0160] and MPEP 2141.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Van Hal, Miller, and Gadewar teach it is known within the art to perform catalytic Guerbet reactions in the gas and/or liquid phase, a person of ordinary skill in the art has good reason to modify Van Hal in order to produce a higher alcohol from a lower alcohol by pursuing the known options within their technical grasp before the effective filing date of the claimed invention, such as adding a basic co-catalysts, as taught by Miller and Gadewar, for the benefit of converting an alcohol to a Guerbet alcohol with increased rates of reaction, increased yields, see Miller, Pg. 6, Lns. 3-8, Pg. 9, Ln. 30-Pg. 10, Ln. 5, lower manufacturing cost, and decreased by-products production, see Gadewar, Paras. [0034];[0126];[0160] and MPEP 2141.
Selection of a known material, such as a suitable combination of bases and metals for a Guerbet reaction catalyst, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945). See MPEP 2144.07.
In addition, “[t]he normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as the concentration of catalyst components and reactants, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969). See MPEP 2144.05.
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699