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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 05/08/2026 has been entered.
Status of the Claims
The amendment filed on 05/08/2026 has been entered. Claim 1 has been amended. Thus claims 1-13 are currently pending, claims 10-13 are withdrawn from further consideration, and claims 1-9 are under examination.
Withdrawn Rejection
The indefinite language of claim 1 has been obviated and thus the 112(b) rejection of the record has been withdrawn.
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 1-9 are rejected under 35 U.S.C. 103 as being unpatentable over Patent number US5,628,880 (US’880; cited in IDS 12/01/2022) as evidenced by Patent number GB1535158A (GB’158) in view of Patent number US6,262,314 (US’314; cited in IDS 12/01/2022). The underlined section addresses the newly added limitations of claim 1.
Regarding claims 1 and 9, US’880 teaches in Fig.1 and Table (columns 6-7) a process for the production of alkyl ethers, the process comprising:
feeding a hydrocarbon feedstock from a comprising C4’s that include n-butane, iso-butane, 1-butene, 2-butene, iso-butene, and diolefins (FCC also produces diolefin, col. 1, lines 28-29) and a first alcohol feedstock to a fixed bed reactor 10 containing an etherification catalyst (col. 4, lines 61-62); contacting the hydrocarbon feedstock 102 and methanol 101 feedstock to react the isoolefins with the alcohol in the presence of the etherification catalyst to produce a first product stream 103 comprising n-butane, iso-butane, 1-butene, 2-butene, diolefins, unreacted iso-butene, and unreacted methanol and one or more ethers;
feeding the first product stream 103, a hydrogen feedstock 105, and a second methanol feedstock (col. 6, lines 34-35) to a catalytic distillation reaction system 20 containing a catalyst to concurrently:
hydrogenate at least a portion of the butadiene (col. 5, lines 17-18), forming additional cis-butene, trans-butene and n-butane (see Table in which the amount of each cis-butene, trans-butene and n-butane increases from line 103 to line108),
etherify at least a portion of the isoolefins and alcohol, forming one or more ethers; and
produce a bottoms product 107 comprising the one or more ethers (col. 6, lines 37-40); and
produce an overhead product 108 (also see the Table) comprising n-butane, isobutane, 1-butene, cis and trans butenes, unreacted isobutene, unreacted methanol and excess hydrogen (separated as uncondensed from 108 via 111).
US’880 teaches that the catalyst in catalytic distillation column 20 comprises hydrogenation catalyst to convert butadiene to internal butenes and etherification catalyst to convert the isoalkenes to ethers. The reference further teaches the use of different hydrogenation catalysts, and exemplifies palladium on alumina catalyst (claim 16 and col. 6, line 17). US’880 is silent that the catalyst system isomerizes at least a portion of the alpha-olefins, in this instance 1-butene forming 2-butenes. However, as shown in the Table, the amount of 1-butene decreases from feedstock 103 to overhead 108 and the amount of the 2-butenes (both cis- and trans-) increases from feedstock 103 to overhead 108. This proves there is a conversion of 1-butene and formation of 2-butene isomers. Furthermore, as evidenced by GB’158, the palladium on alumina catalyst, the same catalyst exemplified in US’880, not only hydrogenates butadiene to 2-butene, it also isomerizes 1-butene to 2-butene. In view of this evidence, the hydrogenation catalyst of US’880 inherently also isomerizes 1-butene in the feedstock 103 to 2-butenes.
Regarding claim 2, the process of US’880 further comprising separating the overhead stream 108, producing C4’s stream 110.
Regarding claim 3, US’880 teaches recycling C4’s to the catalytic distillation reaction system 20 via line 109.
Regarding claim 4, “residual alcohol stream” is formed as an alternate stream in claim 2 and thus any limitation that further limits “residual alcohol stream”, in this case, recycling the residual alcohol stream is not given patentable weight.
Regarding claim 5, the reference further teaches that the temperature in each reaction distillation zone is dependent upon the pressure within the vessel. An overhead pressure of between 100 and 110 psig (~6.9-7.6 barg) is preferred and provides a reaction temperature in the etherification zone of between 90 and 175° F (~32-79° C) and a temperature within the hydrogenation zone of between 85° and 170° F (~29-76.7° C) (lines bridging columns 5-6).
Regarding claims 6-8, in view of the Table, the composition of the feed in line 103 is obtained from etherification reactor 10. There is no conversion of the components in reactor 10 other than the partial etherification of isoolefins and thus, the presence of the other components in line 103 – other than the obtained ethers by the partial etherification – remains unchanged from line 102 to line 103. In other words, the olefins in line 103 would be the same as in line 102, the latter being equivalent to the hydrocarbon feedstock. The hydrocarbon feedstock in US’880 comprises isobutene, 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), and 2-methyl-2-butene (isoamylene).
Note, even though the components of line 103 is the same as the hydrocarbon feedstock 102, the weight percent of each presented in the Table is not the same as in 102, as the amounts in line 103 is based upon the total weight percent that also takes in account the ethers formed in reactor 10. It has been discussed already that the ethers are not present in line 102 other than the olefins and as such, the weight percent of each in line 103 would not read on the claimed weight percent of each in the hydrocarbon feedstock, specifically on the weight percent of isobutene, 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene) and 2-methyl-2-butene as instantly claimed. However, subjecting the hydrocarbon feedstock 102 comprising any amount of each of isobutene, 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), and 2-methyl-2-butene (isoamylene), including the weight percent as claimed, to the etherification reactor 10 of US’880, a skilled artisan would still have a reasonable expectation of success in partially converting the isoolefins to their corresponding ethers. The claimed weight percent of each components are thus prima facie obvious over US’880 unless there is evidence indicating such weight percent as claimed is critical.
Regarding claim 1, US’880 teaches in Fig. 1 etherification catalyst 22 containing the acid cation exchange resin and hydrogenation-isomerization catalyst 24 in the catalytic distillation reaction system 20. Furthermore, the first product stream 103 inlet is located beneath the catalytic zones 22 and 24, the hydrogen feedstock 105 inlet is located below the catalytic zones and above the inlet of the first product stream 103.
US’880 fails to teach that the hydrogen feedstock 105 inlet is at the height of the catalytic zones. In view of MPEP § 2144.04, rearrangement of parts is one of the examples directed to various common practices which the court has held normally require only ordinary skill in the art and hence are considered routine expedients. In this instance, rearranging the location of the hydrogen feedstock 105 inlet from below the catalytic zones to the height of the catalytic zones is not patentable because shifting the position of the hydrogen feedstock 105 inlet would not have modified the operation of the column reactor of US’880.
The reference also fails to teach that the second methanol feedstock inlet is located proximate a top of the catalytic zones. However, locating the second methanol feedstock inlet at any position of the column reactor as long as it passes through the catalytic zones for etherification to take place, a skilled artisan would still have a reasonable expectation of success in yielding nothing more than the predictable alkyl ether product.
US’880 fails to teach the catalysts in a single bed as instantly claimed.
The deficiency is cured by US’314.
US’314 teaches a process for preparing an ether such as tert-amyl-methyl-ether (TAME) and methyl-tert hexyl-ether (MTHE) from C5 and C6 iso-olefins and alcohol by using etherification reactors and catalytic distillation system. As shown in the figure, the reference first teaches that the alcohol and the feedstock comprising C5 and C6 iso-olefins are reacted in the presence of a catalyst in the reactor zone 10 followed by etherification in the catalytic distillation column zone 12 by feeding additional alcohol via lines 34. US’314 teaches that that in the catalytic distillation column zone 12 comprises a single bed catalyst zone 30 containing ion exchange resins for etherification doped with a noble metal such as palladium to promote hydrogenation of diolefin fractions to olefins and isomerization of olefins. The catalytic distillation column zone 12 produces a bottom stream 26 comprising ether and an overhead stream 28 that comprises unreacted alcohol and isoolefins.
Thus, using the catalytic distillation column zone 12 of US’314 that comprises a single bed catalyst zone 30 in place of the catalytic distillation system 20 of US’880, a skilled artisan would have a reasonable expectation of success in conducting nothing more than isomerizing 1-butene to 2-butene isomers, hydrogenating at least a portion of the butadiene to additional cis-butene, trans-butene and n-butane and etherifying the isoolefins to ethers.
In accordance with MPEP § 2143, the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. In this case, at least prong (B) simple substitution of one known element for another to obtain predictable results applies.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a process for the production of alkyl ethers, the process comprising:feeding a hydrocarbon feedstock comprising n-alkanes, isoalkanes, alpha-olefins, internal- olefins, isoolefins, and diolefins and a first alcohol feedstock to a fixed bed reactor containing an etherification catalyst; contacting the hydrocarbon feedstock and the first alcohol feedstock to react the isoolefins with the alcohol in the presence of the etherification catalyst to produce a first product stream comprising n-alkanes, isoalkanes, alpha-olefins, internal-olefins, unreacted isoolefins, diolefins, and unreacted alcohol and one or more ethers; feeding the first product stream, a hydrogen feedstock, and a second alcohol feedstock to a catalytic distillation reaction system containing a single bed of trifunctional catalyst to concurrently: isomerize at least a portion of the alpha-olefins, forming additional internal-olefins, hydrogenate at least a portion of the diolefins, forming additional internal-olefins and alkanes; etherify at least a portion of the isoolefins and alcohol, forming one or more ethers; and produce a bottoms product comprising the one or more ethers; and produce an overhead product comprising n-alkanes, isoalkanes, unreacted alpha- olefins, internal-olefins, unreacted isoolefins, excess hydrogen, and unreacted alcohol; wherein a first product stream inlet is located beneath the single bed of trifunctional catalyst, a hydrogen feedstock inlet is located at a height within the catalytic distillation reaction system above the first product stream inlet proximate a bottom of the single bed of trifunctional catalyst, and a second alcohol feedstock inlet is located proximate a top of the single bed of trifunctional catalyst in view of the combination of US’880 and US’314.
Response to Arguments
Applicant’s arguments are with respect to the newly added limitations of claim 1 and the limitations have been addressed in the rejection above (see the underlined).
Conclusion
Claims 1-9 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.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692
Prosecution Insights