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 without traverse of Group I, claims 6-14 in the reply filed on 03/19/2026 is acknowledged.
Claims 1-5 have been withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.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 Objections
Claim 7 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
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 6 and 8-14 are rejected under 35 U.S.C. 103 as being unpatentable over Samant (Samant, K. D. et al. Patent application publication number US2019/0062251A1; cited in IDS 06/30/2025).
Regarding claims 6 and 8-9, Samant teaches a method for purifying a 1,4-cyclohexanedimethanol composition comprising water, CHDM (1,4-cyclohexanedimethanol), CHDA (1,4-cyclohexanedicarboxylic acid) and byproducts (Table 3, stream S13) via a four distillation system to obtain pure CHDM at a purity of 99.993 wt% ([0097]-[0099], Table 3, stream S15).
The reference further teaches that the byproduct is formed from CHDA by decarbonylation and by reduction of -COOH side-chains to -CH3 side-chains ([0076]), thus it is understood that the byproduct is 1,4-dimethylcyclohexane. It is noted that the unreacted CHDA present in the composition is also interpreted as another byproduct in addition to 1,4-dimethylcyclohexane.
Samant fails to teach the instantly claimed steps of:
a water removal step of removing water from a 1,4-cyclohexanedimethanol (CHDM) crude composition;
a first by-product removal step of removing a by-product having a lower boiling point than 1,4-cyclohexanedimethanol from the 1,4-cyclohexanedimethanol composition that has undergone the water removal step; and
a second by-product removal step of recovering a purified 1,4-cyclohexanedimethanol composition by removing a by-product having a higher boiling point than 1,4-cyclohexanedimethanol from the 1,4-cyclohexanedimethanol composition that has undergone the first by-product removal step.
However, these steps are obvious in view of the teachings of the reference. The boiling points of CHDM, CHDA, and 1,4-dimethylcyclohexane are 283-288 °C, 384.1 °C, and 120-126 °C, respectively. Since the composition is purified via a four column distillation step, it is obvious to the skilled artisan that the components are removed in the order of the compound with the lowest to the compound with the highest boiling point. As shown in Fig. 1, the first column would first remove the off gas as stream S14, followed by the second column to remove water (b.pt. 100 °C), the third column to remove 1,4-dimethylcyclohexane byproduct (b.pt. 120-126 °C, light byproduct) and the fourth column that separates CHDM (b.pt. 283-288 °C) and CHDA byproduct (b.pt. 384.1 °C).
Regarding claim 10, the purified CHDM composition S15 comprises 0 wt% of water (Table 3).
Regarding claim 11, the purified CHDM composition S15 as shown in Table 3 comprises 0.007 wt% byproduct, which is indicated above as being 1,4-dimethylcyclohexane (mol. wt. 112.21 g/mol)
Regarding claim 12, the purified CHDM has 0 wt% of CHDA (mol. wt. 172.18 g/mol).
Regarding claim 13, Samant is silent that the purified 1,4-cyclohexanedimethanol has an APHA value measured according to ASTM D1209 is 10 or less. However, since the purified 1,4-cyclohexanedimethanol in the claim and Samant are produced by identical or substantially identical processes, there is a prima facie case of either anticipation or obviousness for the purified 1,4-cyclohexanedimethanol in the reference to have an APHA value measured according to ASTM D1209 is 10 or less. See MPEP § 2112.01.
Regarding claim 14, the CHDM composition in Samant contains 70% of the trans isomer.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a method for purifying a 1,4-cyclohexanedimethanol composition, comprising the steps of: a water removal step of removing water from a 1,4-cyclohexanedimethanol (CHDM) crude composition; a first by-product removal step of removing a by-product having a lower boiling point than 1,4-cyclohexanedimethanol from the 1,4-cyclohexanedimethanol composition that has undergone the water removal step; and a second by-product removal step of recovering a purified 1,4-cyclohexanedimethanol composition by removing a by-product having a higher boiling point than 1,4-cyclohexanedimethanol from the 1,4-cyclohexanedimethanol composition that has undergone the first by-product removal step in view of the teachings of Samant.
Allowable Subject Matter
The subject matter of claim 7 is free of prior art. The closest prior art reference, Samant (Samant, K. D. et al. Patent application publication number US2019/0062251A1; cited in IDS 06/30/2025), and its teachings have been set forth above. However, the reference fails to teach or suggest the water removal step is performed at a temperature of 50 to 110° C. and a pressure of −0.1 to 0.1 barg as recited in claim 7.
Furthermore, Patent number CN108905256A (CN’256) teaches a multi-tower distillation dehydration energy-saving method, specifically for materials such as 1,4-cyclohexanediethanol (CHDM) ([0036]). In Example 1 ([0062]) and according to Fig. 4, the feed composition comprises water, CHDM and others. First a portion of water is removed from the first distillation column 11, and then the remaining portion of water is removed from the second distillation column 21, which is the same as the design specifications in Figure 3. The top temperature of the first distillation column 11 is 124.8 °C; the top pressure and bottom pressure of the second distillation column 21 are 1.0 bar and 1.1 bar, respectively; and the top temperature and the bottom temperature of the second distillation column 21 are 99.6 °C and 181.1 °C, respectively.
However, CN’256 does not teach or suggest operating the first and/or second distillation column at a temperature of 50 to 110° C. and a pressure of −0.1 to 0.1 barg as recited in claim 7. Accordingly, a skilled artisan would not have been motivated in modifying the water distillation step of Samant with that of CN’256 to arrive at the instantly claimed temperature of 50 to 110° C. and a pressure of −0.1 to 0.1 barg.
In view of the foregoing, the limitation recited in claim 7 is deemed novel and unobvious over the closest prior art.
Conclusion
Claims 6 and 8-14 are rejected and no claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692
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