DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Status
Claims 1 and 11 are amended. Claims 2, 7, and 9 are cancelled.
Claims 1, 3-6, 8, and 10-16 are pending for examination below.
Response to Arguments
Applicant’s arguments and amendments filed 22 May 2026 have been fully considered. Some are persuasive and some are not, as explained below.
The amendment to claim 1 to incorporate the subject matter of claim 2 reciting that the product stream comprising 60 to 80 mol% TMP1 overcomes the Double Patenting rejections because the Double Patenting references do not recite the amount of TMP in the isomerization product, only reciting that the proportion of TMP2 is lower than the feed to isomerization and the proportion of TMP1 is higher than in the feed to isomerization. As such, the Double Patenting rejections are withdrawn.
Applicant argues on page 7 of the Remarks that Ren does not teach the specific zeolite catalyst or specific ion exchange resin claimed in amended claim 1, which is true. Therefore, the rejection over USC 102 has been withdrawn. However, the specific zeolite catalyst and specific ion exchange resin were previously claimed in dependent claims 7 and 9 and rejected under USC 103. The combination of references used for claims 7 and 9 will continue to be used to reject amended claim 1 under USC 103, because the remaining arguments against Ren are not persuasive, as detailed below.
Applicant argues on page 6 of the Remarks that the only disclosure is in Example 5 of the CN reference, which uses a feed comprising 24 wt% TMP2, which is outside the range of at least 25 mol% of instant claim 1.
In response, the Examiner respectfully disagrees. The feed stream cited by Applicant comprising 24 wt% TMP2 is fed to the distillation, not to the isomerization. The bottoms stream from the distillation is the feed to the isomerization as claimed, as cited by the Examiner in the Non-Final Action (see paragraphs [0061]-[0063] and Figure). The bottoms stream contains 55.1 wt% TMP2 (Table 2), which is within the claimed range of at least 25 mol% of instant claim 1. As such, Ren continues to teach the claimed feed to isomerization comprising at least 25 mol% TMP2.
Applicant argues on pages 6-7 of the Remarks that the top product stream of the process comprises 98.5 wt% TMP1, which is very high purity and outside the claimed range of 60 to 80 mol%.
In response, the Examiner respectfully notes that the stream comprising 98.5 wt% TMP1 is not equivalent to the claimed product stream. The very pure stream of Ren is obtained after distillation of the isomerized stream (see Figure and Table 2). The product stream of the isomerization, which is what is passed to the distillation to obtain the pure stream, instead comprises 68 wt% (68 mol%) 2,4,4-trimethyl-1-pentene and 24 wt% (24 mol%) 2,4,4-trimethyl-2-pentene (paragraph [0063], Table 2). This continues to be within the range of 60 to 80 mol% previously recited in claim 2 and now presented in claim 1, and Ren continues to teach the claimed amounts.
Applicant argues on pages 7-10 of the Remarks that none of the previously cited secondary references overcome the deficiencies of Ren discussed above.
In response, the Examiner notes that none of the secondary references were intended to teach the amounts of TMP2 in the feed and TMP1 in the product, which are disclosed by Ren. Thus, the argument that the secondary references don’t overcome this issue is moot.
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.
Claims 1, 3-5, and 13-16 are rejected under 35 U.S.C. 103 as being unpatentable over Ren et al. (CN 113198519, machine translation provided 2/26/2026) in view of Powers (US 2004/0122278) and Brownscombe (US 4,992,613).
With regard to claims 1, 3, 14, and 15, Ren teaches a process for isomerization (Abstract) comprising the following:
a) providing a stream comprising 55.1 wt% 2,4,4-trimethyl-2-pentene from the bottom of a distillation column (input stream) to an isomerization reactor (paragraphs [0061]-[0063], Table 2, and Figure). As mol% and wt% are equivalent when talking about isomers, the amount is equivalent to 55.2 mol%, which is within the range of at least 25 mol% of instant claim 1.
b) isomerizing the bottoms stream using a heterogeneous zeolite catalyst to produce a product stream (paragraph [0061]).
Ren further teaches that the product of the isomerization is the feed to the distillation column (Figure), and that the feed to the distillation column includes 68 wt% (68 mol%) 2,4,4-trimethyl-1-pentene and 24 wt% (24 mol%) 2,4,4-trimethyl-2-pentene (paragraph [0063], Table). The amount of 2,4,4-trimethyl-1-pentene is within the range of 60 to 80 mol% of instant claim 1 and the range of 65-80 mol% of instant claim 14. The amount of 2,4,4-trimethyl-2-pentene is within the range of 20-40 mol% of instant claim 3 and the range of 20-35 mol% of instant claim 15.
Ren fails to teach the zeolite is a zeolite beta catalyst
Powers teaches a process for producing alpha-olefins from internal olefins (Abstract). Powers teaches that the process comprises reacting the internal olefin with any isomerization catalyst which promotes double bond shifts, such as the zeolite catalyst in US Pat 4,922,613 (to Brownscombe) (paragraph [0024]).
Brownscombe teaches double bond isomerization over zeolite catalysts, which can be any zeolite including zeolite beta. Brownscombe further teaches that basic zeolites provide more selectivity for double bond isomerization (column 1, lines 11-12) and Powers further teaches that the zeolites of Brownscombe are suitable for the isomerization of internal olefins to alpha-olefins (paragraph [0024]), which is the reaction taking place in Ren.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the zeolite catalyst of Powers and Brownscombe in the process of Ren, because each of Ren, Powers, and Brownscombe teaches isomerization with a zeolite catalyst, Powers teaches the zeolite catalyst of Brownscombe is useful to isomerize internal olefins to desired alpha olefins as in Ren, and Brownscombe teaches that the basic zeolite beta catalyst is selective for the double bond isomerization.
With regard to claim 4, Ren is silent regarding the isomerization pressure. Thus, one of ordinary skill in the art would look to related art to determine a suitable pressure.
Powers teaches a process for isomerization of internal olefins to alpha olefins (Abstract) in the presence of a zeolite catalyst (paragraph [0024]). Powers further teaches the pressure for the isomerization is a wide range due to the different feeds and catalysts which can be used, but will generally be from about 0 to about 250 psig (0 to 17 bar) (paragraph [0025]), which is within the range of less than 40 bar of instant claim 4.
Therefore it would have been obvious to one of ordinary skill in the art at the time of the invention to use the pressure range of Powers in the process of Ren, because each of Ren and Powers teaches isomerization of internal olefins to alpha olefins with a zeolite catalyst, Ren is silent regarding the pressure, and Powers teaches that a pressure within the claimed range is known and that one of ordinary skill in the art can determine suitable pressure based on the feed and catalyst as well (paragraph [0025]).
With regard to claim 5, Ren teaches the isomerization is at a temperature of 80°C (paragraph [0061]), which is within the range of 25-90°C of instant claim 5.
With regard to claim 13, Ren teaches the method above.
Ren is silent regarding the reaction being in liquid phase. Thus, one of ordinary skill in the art would look to related art to determine the phase of the reaction.
Powers teaches a process for isomerization of internal olefins to alpha olefins (Abstract) in the presence of a zeolite catalyst (paragraph [0024]). Powers further teaches the isomerization can be in liquid phase (paragraph [0013]). Therefore, Powers teaches that it is known to perform a similar isomerization in liquid phase.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to perform the isomerization of Ren in liquid phase, as claimed, because each of Ren and Powers teaches isomerization of internal olefins to alpha olefins with a zeolite catalyst, Ren is silent regarding the phase, and Powers teaches that it is known to perform the reaction in liquid phase.
With regard to claim 16, Ren teaches the temperature for the isomerization is 70-120°C (paragraph [0025]), which overlaps the range of 35-70°C of instant claim 16 at the endpoint, rendering the range prima facie obvious.
Claims 6 and 8 are rejected under 35 U.S.C. 103 as being unpatentable over Ren et al. (CN 113198519, machine translation provided 2/26/2026) in view of Powers (US 2004/0122278) and Brownscombe (US 4,992,613) as applied to instant claim 1, and further in view of Wadlinger et al. (US 3,308,069).
With regard to claims 6 and 8, Ren in view of Powers and Brownscombe teaches the method of isomerization with a zeolite beta catalyst above. Brownscombe teaches that the zeolite beta catalyst can be the zeolite beta as in 3,308,069 (to Wadlinger), which is incorporated by reference (column 2, lines 48-52). Wadlinger teaches that zeolite beta can have a silica to alumina ratio of 10 to 150. This is equivalent to a Si:Al ratio of 20 to 300, which overlaps the range of 40 to 200 of instant claim 6, rendering the range prima facie obvious. Wadlinger further teaches replacing the sodium ions from the synthesis of the beta zeolite with hydrogen ions (column 5, lines 54-55). Thus, the catalyst of Powers in view of Brownscombe and Wadlinger in a H beta zeolite (Z-beta-H) of instant claim 8.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the zeolite beta being H beta and having the claimed silica alumina ratio in the process of Ren in view of Powers and Brownscombe, because Ren in view of Powers and Brownscombe teaches the isomerization with a zeolite beta catalyst, and Brownscombe further incorporates by reference the zeolite beta of Wadlinger which comprises the claimed silica alumina ratio and H beta zeolite.
Claims 1, 3, 4, and 10-16 are rejected under 35 U.S.C. 103 as being unpatentable over Ren et al. (CN 113198519, machine translation provided 2/26/2026) in view of Powers (US 2004/0122278) and Haag (US 3,326,866).
With regard to claims 1, 3, 10-12, 14, and 15, Ren teaches a process for isomerization (Abstract) comprising the following:
a) providing a stream comprising 55.1 wt% 2,4,4-trimethyl-2-pentene from the bottom of a distillation column (input stream) to an isomerization reactor (paragraphs [0061]-[0063], Table 2, and Figure). As mol% and wt% are equivalent when talking about isomers, the amount is equivalent to 55.2 mol%, which is within the range of at least 25 mol% of instant claim 1.
b) isomerizing the bottoms stream using a heterogeneous zeolite catalyst to produce a product stream (paragraph [0061]).
Ren further teaches that the product of the isomerization is the feed to the distillation column (Figure), and that the feed to the distillation column includes 68 wt% (68 mol%) 2,4,4-trimethyl-1-pentene and 24 wt% (24 mol%) 2,4,4-trimethyl-2-pentene (paragraph [0063], Table). The amount of 2,4,4-trimethyl-1-pentene is within the range of 60 to 80 mol% of instant claim 1 and the range of 65-80 mol% of instant claim 14. The amount of 2,4,4-trimethyl-2-pentene is within the range of 20-40 mol% of instant claim 3 and the range of 20-35 mol% of instant claim 15.
Ren fails to teach the use of an ion exchange resin as the catalyst.
Powers teaches a process for producing alpha-olefins from internal olefins (Abstract) comprising reacting the internal olefin with any isomerization catalyst which promotes double bond shifts, such as zeolites or sulfonated resins. Powers further teaches the sulfonated resins are those as in US Pat 3,326,866 (to Haag) (paragraph [0024]) thus incorporating by reference Haag. Haag teaches the sulfonated resins comprise styrene monomers co-polymerized with divinylbenzene (co-oligomers of aromatic vinyl compounds which are styrene and divinylbenzene of instant claims 1, 10, and 11) (column 2, lines 9-11 and 23-26). Haag further teaches that the acid groups can be at least partially replaced with non-polar groups (partially neutralized instant claim 12) to enhance the catalytic activity (column 4, lines 35-38).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the sulfonated ion-exchange resin of Powers in view of Haag in the process of Ren, because each of Ren and Powers teach isomerization of internal olefins to alpha olefins with a catalyst, Powers teaches that sulfonated resins and zeolites are each useful catalysts for the process, thus teaching the idea of using sulfonate resins, and Haag teaches that the claimed sulfonated styrene resins formed from the claimed styrene and divinylbenzene aromatic monomers have enhanced catalytic activity.
With regard to claim 4, Ren teaches the method above.
Ren is silent regarding the isomerization pressure. Thus, one of ordinary skill in the art would look to related art to determine a suitable pressure.
Powers teaches a process for isomerization of internal olefins to alpha olefins (Abstract) in the presence of a zeolite catalyst (paragraph [0024]). Powers further teaches the pressure for the isomerization is a wide range due to the different feeds and catalysts which can be used, but will generally be from about 0 to about 250 psig (0 to 17 bar) (paragraph [0025]), which is within the range of less than 40 bar of instant claim 4.
Therefore it would have been obvious to one of ordinary skill in the art at the time of the invention to use the pressure range of Powers in the process of Ren, because each of Ren and Powers teaches isomerization of internal olefins to alpha olefins with a zeolite catalyst, Ren is silent regarding the pressure, and Powers teaches that a pressure within the claimed range is known and that one of ordinary skill in the art can determine suitable pressure based on the feed and catalyst as well (paragraph [0025]).
With regard to claim 5, Ren teaches the isomerization is at a temperature of 80°C (paragraph [0061]), which is within the range of 25-90°C of instant claim 5.
With regard to claim 13, Ren teaches the method above.
Ren is silent regarding the reaction being in liquid phase. Thus, one of ordinary skill in the art would look to related art to determine the phase of the reaction.
Powers teaches a process for isomerization of internal olefins to alpha olefins (Abstract) in the presence of a zeolite catalyst (paragraph [0024]). Powers further teaches the isomerization can be in liquid phase (paragraph [0013]). Therefore, Powers teaches that it is known to perform a similar isomerization in liquid phase.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to perform the isomerization of Ren in liquid phase, as claimed, because each of Ren and Powers teaches isomerization of internal olefins to alpha olefins with a zeolite catalyst, Ren is silent regarding the phase, and Powers teaches that it is known to perform the reaction in liquid phase.
With regard to claim 16, Ren teaches the temperature for the isomerization is 70-120°C (paragraph [0025]), which overlaps the range of 35-70°C of instant claim 16 at the endpoint, rendering the range prima facie obvious.
Conclusion
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALYSSA L CEPLUCH whose telephone number is (571)270-5752. The examiner can normally be reached M-F, 8:30 am-5 pm, EST.
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/Alyssa L Cepluch/Examiner, Art Unit 1772
/Renee Robinson/Primary Examiner, Art Unit 1772
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