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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 12/19/2025 has been entered.
Claim 24 has been added.
Claim 12 has been cancelled.
Claims 1-11 ,13-24 are currently pending and have been fully considered.
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 17 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding claim 17, the phrase "for example" renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
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.
Claim(s) 1-11 and 13-24 is/are rejected under 35 U.S.C. 103 as being unpatentable over GARCIA-MARTINEZ (WO 2006 031259 A2) in view of CLARK (US 7795487B).
GARCIA-MARTINEZ teaches mesostructured zeolitic materials and their applications.
Regarding claims 1 and 16, one application is taught to contacting a petrochemical feed with mesostructured zeolitic materials for alkylating and transalkylating aromatic hydrocarbons such as benzene and alkylbenzenes. (ln 7-21 of page 86 of GARCIA-MARTINEZ)
The mesostructured zeolitic materials is prepared by adding. (ln 4-13 of page 5 of GARCIA-MARTINEZ)
The method taught in GARCIA-MARTINEZ produces nanostructured zeolites with high surface area. (ln 23-30 of page 48 of GARCIA-MARTINEZ) A surfactant is taught to be used to penetrate the zeolite, creating mesopores. The size of the mesopore depends on the type of surfactant. (ln 30-33 of page 44 of GARCIA-MARTINEZ) Much of the surface area is the surface area of mesoporous surfaces and is controlled at least in part by the pore volume. (page 66 of GARCIA-MARTINEZ)
The treatment of the zeolite with the surfactant results in a plurality of mesopores and would be expected to have a higher mesoporus surface area. (ln 1 - 11 of page 9 of GARCIA-MARTINEZ)
GARCIA-MARTINEZ teaches that one aspect comprises an inorganic material having fully crystalline mesostructured zeolites. (ln 12 - 13 of page 7 of GARCIA-MARTINEZ)
GARCIA-MARTINEZ teaches that fully crystalline mesostructured zeolites and/or crystalline nanostructured zeolites are unique molecular sieves with both microporosity and mesoporosity. (ln 32-33 of page 87 of GARCIA-MARTINEZ)
GARCIA-MARTINEZ teach that H-Y [MCM-41] is a hybrid structure and recognized as such in lines 12-23 of page 54. GARCIA-MARTINEZ further teaches how H-Y [MCM-41] is produced in example 1 on pages 89-90.
H-Y is a microporous zeolite and known in the art.
The treatment of H-Y zeolite in example 1 on pages 89-90 imparts mesoporosity to the hybrid structure of a produced H-Y [MCM-41]. H-Y [MCM-41] is taught on Table 1 of GARCIA-MARTINEZ to comprise pore diameters of 2.6 nms which are mesopores.
GARCIA-MARTINEZ teaches an example of H-Y [MCM-41] in which the presence of mesopores is at least double the surface area of H-Y. H-Y is a zeolite comprising microporosity. The additional surface area would be attributed to the process of imparting mesoporosity and would be expected to result in a ratio of mesoporous surface area of at least 1:1 with the microporous surface area. (a ratio of mesoporous surface area to microporous surface area greater than 0.9) (ln 20-25 of page 61)
Although GARCIA-MARTINEZ teaches that generally, suitable conditions for transalkylation include for example, is from about 340 to about 500 C, GARCIA-MARTINEZ also teaches that suitable conditions for contacting the petrochemical feed with mesostructured zeolites is from about 100°C to about 700°C. (ln 7-26 of page 86 of GARCIA-MARTINEZ)
GARCIA-MARTINEZ teaches an example range for temperature and one of ordinary skill in the art, given what is also taught in regards to general conditions for contacting, would not limit the transalkylation temperature range to only about 340 to about 500 C.
In non-general cases, the transalkylation temperature may be expected to be outside the range of about 340 to about 500°C.
CLARK teaches a temperature range of 100 to 260°C for transalkylation in lines 52-60 of column 6.
One of ordinary skill in the art would apply known transalkylation temperatures, along with the general teachings for contacting taught in GARCIA-MARTINEZ, such as a temperature range of between about 100°C to about 250°C with a reasonable expectation of success.
In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Furthermore, regarding claim 16, the method of alkylating is taught to be performed with the mesostructured zeolite along with an alkylating agent. The mesostructured zeolites may be used for alkylation and transalkylation. (ln 7-26 of page 86 of GARCIA-MARTINEZ)
If the preferred product is mono-alkylated benzene, it would be obvious to one of ordinary skill in the art to apply an alkylation reaction to produce a product and separating the mono-alkylated benzene from an alkylation effluent.
The alkylation effluent may be treated again in a transalkylation reaction to further produce further mono-alkylated benzene.
Treating an effluent with unconverted compounds to further produce a desired product is a well-known technique to one of ordinary skill in the art.
For example, CLARK teaches cumene is valuable as a commodity chemical.
CLARK further teaches alkylation processes in commercial uses for production of ethylbenzene and cumene is known in the art. It is well known in the art to transalkylate the polyalkylated by products with benzene or other alkylatable aromatic to produce additional ethylbenzene or cumene. (ln 15-59 of column 1 of CLARK)
Regarding claims 21-22, CLARK teaches cumene is valuable as a commodity chemical.
It is well known in the art to transalkylate the polyalkylated by products with benzene or other alkylatable aromatic to produce additional ethylbenzene or cumene.
Recycling an effluent to further produce more desired product would be well obvious to one of ordinary skill in the art.
When the desired product is a mono-alkylated benzene, and the reaction is alkylation or transalkylation, separation of benzene from the effluent and recycling the benzene would be obvious to one of ordinary skill in the art.
Regarding claim 2, GARCIA-MARTINEZ is directed toward the formation and application of a mesostructured zeolite.
Regarding claims 3-4, the zeolite includes those of faujasite type (FAU). (ln 20-21 of page 4 of GARCIA-MARTINEZ)
Regarding claim 18, the mesoporous zeolite is taught to include all crystalline mesoporous materials such as zeolites such as MSI-S (BEA). (ln 1-2 of page 40 of GARCIA-MARTINEZ)
Regarding claims 5 and 17, a surfactant is taught to be used to penetrate the zeolite, creating mesopores. The size of the mesopore depends on the type of surfactant. (ln 30-33 of page 44 of GARCIA-MARTINEZ)
Much of the surface area is the surface area of mesoporous surfaces and is controlled at least in part by the pore volume. (page 66 of GARCIA-MARTINEZ)
The treatment of the zeolite with the surfactant would be expected to result in a higher mesoporus surface area.
Improving the mesoporous surface area appear well within one of ordinary skill in the art based on the sizes of the mesopores formed.
Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Regarding claim 6, a surfactant is used to achieve desired mesopore structure of the mesoporous zeolite. (ln 5-10 of page 42 of GARCIA-MARTINEZ)
Regarding claim 7, the surfactant may be cetyltrimethylammonium bromide. (ln 26-27 of page 4 of GARCIA-MARTINEZ)
Regarding claims 8 and 10, the process to prepare the mesostructured zeolite include adding an acid or a base. (ln 20-21 of page 4 of GARCIA-MARTINEZ)
Regarding claim 9, a metal altering medium may be added such as EDTA. (ln 20-24 of page 4 of GARCIA-MARTINEZ)
Regarding claim 11, the base may be NaOH. (ln 20-24 of page 4 of GARCIA-MARTINEZ)
Regarding claim 13, although GARCIA-MARTINEZ teaches that generally, suitable conditions for transalkylation include for example, is from about 340 to about 500 C, GARCIA-MARTINEZ also teaches that suitable conditions for contacting the petrochemical feed with mesostructured zeolites is from about 100°C to about 700°C. (ln 7-26 of page 86 of GARCIA-MARTINEZ)
GARCIA-MARTINEZ teaches an example range for temperature and one of ordinary skill in the art, given what is also taught in regards to general conditions for contacting, would not limit the transalkylation temperature range to only about 340 to about 500 C.
In non general cases, the transalkylation temperature may be expected to be outside the range of about 340 to about 500°C.
CLARK teaches a temperature range of 100 to 260°C for transalkylation in lines 52-60 of column 6.
One of ordinary skill in the art would apply known transalkylation temperatures, along with the general teachings for contacting taught in GARCIA-MARTINEZ, such as a range of about 150°C to 220°C with a reasonable expectation of success.
In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Regarding claim 14 and 19, one application of the mesostructured zeolitic material is in the catalytic cracking of 1,3,5-triisopropyl benzene to diisopropyl benzene and cumene. (ln 1-6 of page 37 of GARCIA-MARTINEZ)
Regarding claim 15 and 20, a binder may be added. (ln 9-14 of page 76 of GARCIA-MARTINEZ)
Regarding claim 23, impurities may be removed from a feedstock through catalyst beds. (ln 25-34 of page 82 of GARCIA-MARTINEZ) Adsorbents can be used to remove impurities. (ln 1-8 of page 21 of GARCIA-MARTINEZ)
Regarding claim 24, although GARCIA-MARTINEZ teaches that generally, suitable conditions for transalkylation include for example, is from about 340 to about 500 C, GARCIA-MARTINEZ also teaches that suitable conditions for contacting the petrochemical feed with mesostructured zeolites is from about 100°C to about 700°C. (ln 7-26 of page 86 of GARCIA-MARTINEZ)
GARCIA-MARTINEZ teaches an example range for temperature and one of ordinary skill in the art, given what is also taught in regards to general conditions for contacting, would not limit the transalkylation temperature range to only about 340 to about 500°C.
In non-general cases, the transalkylation temperature may be expected to be outside the range of about 340 to about 500°C.
CLARK teaches a temperature range of 100 to 260°C for transalkylation in lines 52-60 of column 6.
One of ordinary skill in the art would apply known transalkylation temperatures, along with the general teachings for contacting taught in GARCIA-MARTINEZ, such as a range of about 150 to 220°C, with a reasonable expectation of success.
In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990).
Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art at the time of the invention.
Response to Arguments
Applicant's arguments and amendments filed 12/19/2025 have been fully considered and have necessitated new grounds of rejection in view of the same prior art, GARCIA-MARTINEZ (WO2006031259A2) in view of CLARK (US 7795487B).
Applicant argues that GARCIA-MARTINEZ and CLARK, does not teach the limitation of “a ratio of mesoporus surface area to microporous surface area greater than 0.9.” Applicant argues that the teaching in GARCIA-MARTINEZ in which H-Y [MCM-41] in which the presence of mesopores is at least double the surface of H-Y. H-Y is a zeolite comprising microporosity could not lead one to expect a ratio of mesoporous surface area to microporous surface area greater than 0.9.
Applicant argues that H-Y[MCM-41] is a different catalyst than H-Y. Applicant further argues that GARCIA-MARTINEZ does not teach the surface area of H-Y [MCM-41] consists of 50%, 90% or 100% mesoporous surface area.
GARCIA-MARTINEZ teaches that H-Y [MCM-41] is a hybrid structure and recognized as such in lines 12-23 of page 54. GARCIA-MARTINEZ further teaches how H-Y [MCM-41] is produced in example 1 on pages 89-90.
H-Y is a microporous zeolite and known in the art.
The treatment of H-Y zeolite in example 1 on pages 89-90 imparts mesoporosity to the hybrid structure of a produced H-Y [MCM-41]. H-Y [MCM-41] is taught on Table 1 of GARCIA-MARTINEZ to comprise pore diameters of 2.6 nms which are mesopores.
GARCIA-MARTINEZ further teaches an example of H-Y [MCM-41] in which the presence of mesopores in the H-Y [MCM-41] is at least double the surface area of H-Y. H-Y is a zeolite comprising microporosity. The additional surface area would be attributed to the process of imparting mesoporosity and would be expected to result in a ratio of mesoporous surface area of at least 1:1 with the microporous surface area. (a ratio of mesoporous surface area to microporous surface area greater than 0.9) (ln 20-25 of page 61)
Applicant argues that assuming, arguendo, that GARCIA-MARTINEZ teaches a catalyst having a ratio of mesoporous surface area to microporous surface area greater than 0.9, such a ratio would not be a result effective variable that motivates one of ordinary skill in the art to utilize the catalyst under transalkylation conditions at a temperature of 100 to 250°C.
Applicant notes that the conditions for alkylation taught in GARCIA-MARTINEZ is from about 250 to 500°C. Applicant argues that GARCIA-MARTINEZ does not teach a general range of 100 – 700°C for transalkylation but that the range of 100 – 700°C are for different reactions other than transalkylation. Applicant bases this on the fact that GARCIA-MARTINEZ teaches the conditions for transalkylation includes a temperature from about 340 to about 500°C and after the excerpt, does GARCIA-MARTINEZ teach generally suitable reaction conditions.
This is not persuasive as GARCIA-MARTINEZ teaches general suitable conditions for multiple different reactions prior to stating the general suitable conditions for contacting a petrochemical or hydrocarbon feed with the fully crystalline mesostructured zeolites and/or crystalline nanostructure zeolite is from 100 to 700°C.
Although GARCIA-MARTINEZ teaches that generally, suitable conditions for transalkylation include for example, is from about 340 to about 500°C, GARCIA-MARTINEZ also teaches that suitable conditions for contacting the petrochemical feed with mesostructured zeolites is from about 100°C to about 700°C. (ln 7-26 of page 86 of GARCIA-MARTINEZ)
GARCIA-MARTINEZ teaches an example range for temperature for transalkylation and one of ordinary skill in the art, given what is also taught in regards to general conditions for contacting, would not limit the transalkylation temperature range to only about 340 to about 500°C.
In non-general cases, the transalkylation temperature may be expected to be outside the range of about 340 to about 500°C, CLARK teaches a temperature range of 100 to 260°C for transalkylation in lines 52-60 of column 6. A range of 100 to 250°C is known in the art.
One of ordinary skill in the art would apply known transalkylation temperatures along with the general teachings for contacting taught in GARCIA-MARTINEZ with a reasonable expectation of success.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
YING et al. (USPGPUB 2009/0326177) teach that H-Y [MCM-41] is a hybrid structure and recognized as such in paragraph 77. YING et al. further teaches how H-Y [MCM-41] is produced in paragraph 103.
The treatment of H-Y zeolite in paragraph 77 imparts mesoporosity to the hybrid structure of a produced H-Y [MCM-41]. H-Y [MCM-41] is taught on Table 1 of YING et al. to comprise pore diameters of 2.6 nms which are mesopores.
VINCENT (US 8993820) teaches an alkylation process of at least partially untreated alkylatable aromatic compound with zeolites.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MING CHEUNG PO whose telephone number is (571)270-5552. The examiner can normally be reached M-F 10-6.
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, PREM SINGH can be reached at 5712726381. 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.
/MING CHEUNG PO/ Examiner, Art Unit 1771
/ELLEN M MCAVOY/ Primary Examiner, Art Unit 1771