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 .
Applicant's election with traverse of Group I, claims 1-10 and 16-20 in the reply filed on July 09, 2026, is acknowledged. The traversal is on the ground(s) that the groups of claims are therefore connected at least by the aliphatic poly product. This is not found persuasive because the polyol product such as, propane-1,2,3-trimethanol is known in the art (see Example 7 of US 5,391,771).
The requirement is still deemed proper and is therefore made FINAL.
Claims 11-15 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected inventions, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on July 09, 2026.
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.
Claims 1-10 and 16-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Weyer et al (US 5,391,771) in view of Mitsubishi (JP H1087533A machine translation).
Applicants’ claimed invention is directed to a method of preparing a product comprising (a) one, two, or more product compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms in the range of from 5 to 6 or (b) one or more reaction products of said one, two, or more compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms in the range of from 5 to 6,comprising:(i) providing or preparing a starting material comprising a starting compound selected from the group consisting of aliphatic tricarboxylic acids having a total number of 6 carbon atoms, esters thereof, anhydrides thereof, and salts thereof,(ii) providing or preparing a solvent having a dielectric constant above the dielectric constant of n-butanol, and (iii) chemically converting said starting compound provided or prepared in step (i) - at a temperature in the range of from 80 0C to 155 - at a partial pressure of hydrogen in the range of from 15 MPa to 30 MPa,- in said solvent provided or prepared in step (ii), and- in the presence of a heterogeneous hydrogenation catalyst comprising one or more metals selected from the group consisting of Mn, Re, Fe, Ru, and Os, so that carboxyl groups, carboalkoxy groups, anhydride groups, and/or carboxylate groups as present in the starting compound are selectively hydrogenated to the corresponding hydroxy groups so that a product results comprising one, two, or more product compounds selected from the group consisting of aliphatic polyols having three or more hydroxy groups and a total number of carbon atoms in the range of from 5 to 6.
Weyer teaches the liquid-phase catalytic hydrogenation of a 6 carbon atoms aliphatic tricarboxylic acid (specially, citric acid or its C1 to C2, alkyl ester) using a heterogeneous Ru catalyst under high hydrogen pressure (1 to 400 bar) and temperature (50 to 400 C) to yield the 3-hydroxy polyol target, propane-1,2,3-trimethanol. Weyer teaches that this reduction occurs within a nonaqueous solvent system consisting of organic ethers or alkanols. See Example 7 and claims 1-4.
However, Mitsubishi teaches a method for hydrogenating a C6 tricarboxylic ester derivative (trialkyl 1,2,4-butanetricarboxylate) in a liquid phase to obtain a highly selective tri-alcohol layout (3-hydroxymethyl-1,6-hexanediol). Critically, Mitsubishi teaches that utilizing lower saturated alcohols, specially methanol or ethanol as the liquid reaction solvent significantly improves overall reaction rates and target polyol selectivity. See page 3, 3rd paragraph.
It would have been obvious to a person of the ordinary skill in the art, prior to the effective filing date of the claimed invention would recognize that methanol and ethanol inherently posses dielectric constants of
∈
=33 and 24.5, respectively that sit squarely above the baseline of n-butanol (
∈
=17.8). therefore, by simply following Mistsubishi’s instructions to use methanol or ethanol in a liquid phase tricarboxylic reduction, a PHOSITA would inherently and inevitably fulfill the step (ii) high dielectric solvent requirement of claim 1.
It would have been obvious to a PHOSITA, prior to the filing date of the claimed invention to modify the nonaqueous ether solvent of Weyer by substituting it with the lower saturated alcohol solvents taught by Mitsubishi. The motivation to make this modification is explicitly provided by Mitsubishi to maximize reaction rates and improve the handling/selectivity of multi-hydroxyl structure.
Regarding claim 2, this claim specifies starting materials selected from alpha-functionalized aliphatic tricarboxylic acids, alpha-beta unsaturated aliphatic tricarboxylic acids, or tricarballylic acid. Weyer explicitly teaches using citric acid. Citric acid is inherently an alpha-functionalized aliphatic tricarboxylic acid because it contains a hydroxyl group on the alpha carbon relative to its central carboxylic acid. Specifying the structure category of an identical starting material lacks patentable weight. See Examples 10 to 16.
Regarding claim 3, this claims limits the target to aliphatic polyol with 3 or 4 hydroxy groups and 5 to 6 carbon atoms. Weyer explicitly teaches producing propane-1,2,3-trimethanol, which contains exactly 3 hydroxyl groups and 6 carbon atoms. Targeting a specific compound explicitly named in the primary reference is a predictable result. See Example 7.
Regarding claim 4, this claim defines the high dielectric-solvent as comprising water, methanol, ethanol, n-propanol, iso-propanol, ethylene glycol, propylene glycols, or cyclic ethers. Because the claim is written in the broad, inclusive comprises or selected from format, the examiner will point out the Mitsubishi explicitly names methanol and ethanol as its preferred solvents. Because the prior art explicitly discloses elements of your listed group, the claim is obvious. See page 3, the 3rd paragraph.
Regarding claim 5, this claim defines the temperature range of 120 to 155 C. Weyer teaches the hydrogenation is conducted at 150 C, which is within the temperature range recited in claim 5. See Example 7.
Regarding claim 6, this claim specifies that the heterogeneous hydrogenation catalyst must contains 90 wt% or more of Group 7/8 metals (Mn, Re, Ru, Os) or 10 wt% or more of those metals combined with other transition metals (Co, Rh, Ni, Pd, Pt, Cu, etc.) to equal 98 wt% or more. Both Weyer(Table 1) and Mitsubishi describe pure or bimetallic catalyst on standard framework. Adjusting active metal loading ratios to maximizes active catalytic surfaces is a standard optimization process for chemical engineers.
Regarding claim 7, this claim requires the heterogenous catalyst to be supported by a support material. Weyer describes heterogenous catalysts and placing transition metals like Ruthenium onto industrial supports like carbon black, silica, alumina, or titania to prevent leaching is a textbook requirement in industrial chemistry. Table 1 and claim 4.
Regarding claim 8, this claim introduces subsequent processing steps: removing the solvent via evaporation, chemically converting the polyols to a secondary reaction product (part b), or adding additional chemical substances. Removing a volatile reaction solvent like methanol or ethanol via distillation or evaporation is an inherent post processing step required to isolate any organic product. Additionally, Weyer explicitly targets downstream derivatives (like lactones or cyclic ethers) made by secondary conversion of the initial reduction intermediates. See example 7, col. 1 lines 36-55.
Regarding claim 9, this claim states that the starting materials is prepared or isolated from plant material. Citric acid is universally known as a biomass-derived acid traditionally harvested from citrus fruits or manufactured via agricultural fermentation (e.g., via Aspergillus niger) Sourcing a well-known chemical starting material from its most common, commercially available bio-renewable origin does not lend patentable novelty to a chemical process.
Regarding claim 10, this claim covers formulations or reaction mixtures (for polyalkoxylates or polymers) using the generated polyols. Multi-hydroxy aliphatic polyols are well -documented humectants, cross linkers, and plasticizers. Incorporating a polyol generated by a known process into standard consumer formulations or polymer blends yields completely predictable physical property improvements based entirely on the inherent, known behavior of tri-alcohols. See Weyer, col. 4, lines 20-30.
Regarding claims 16-20, these claims expand on routine process additions or compound fractions generated during the execution of steps (i) through (iii). Just as with claims 6, 7 and 8, adjustment to flow dynamics, fractional distillation cutting, or straightforward additive blending are within the day-to-day technical expertise of a routine chemical facility and produce entirely predictable outcomes.
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/JAFAR F PARSA/Primary Examiner, Art Unit 1692
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