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 1-5, 8, 10, 28, 67, and 77 are amended. Claims 88 and 89 are new. Claims 6, 9, 11-21, 23, 25, 26, 29, 31-49, 51-63, 65, 66, 68-71, 73-75, and 78-86 are cancelled.
The amendments to claims 1-5, 8, 10, 28, 67, and 77 overcome the previous objections and 112 rejections.
Claims 1-5,7-8,10,22,24,27-28,30,50,64,67,72,76-77 and 87-89 are pending for examination below.
Response to Arguments
Applicant’s arguments, see Remarks, filed 10 March 2026, with respect to the rejection(s) of claim(s) 1-5,7-8,10,22,24,27-28,30,50,64,67,72,76-77 and 87 under USC 102 and 103 have been fully considered and are persuasive. Buchold does not teach that the feed stream does not comprise methanol, as in independent claim 1, or that the ethanol is present as the predominant oxygenate, as in independent claims 67 and 77. Therefore, the rejections have been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of newly cited prior art in view of the amendments.
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.
Claims 67, 72, and 88 are 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.
With regard to claim 67, the claim recites in lines 4-5 “the first input feed comprising one or more first oxygenates, the one or more first oxygenates comprising ethanol and at least one of methanol or dimethylether…” This wording makes it unclear how many oxygenates are required in the first input feed, because the first recitation is “one or more” but then the second recitation requires at least two oxygenates (ethanol and at least one of methanol or dimethyl ether). Thus, the claim is indefinite.
For purposes of examination, the Examiner will consider that the claim is intended to require the at least two oxygenates including ethanol and at least one of methanol or dimethylether.
With regard to claims 72 and 88, the claims are rejected as being dependent on a rejected base claim.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1-5, 7, 8, 22, 50, 64, 76, 87, and 89 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Rothaemel et al. (US 2010/0234655).
With regard to claims 1, 2, 22, 64, and 87, Rothaemel teaches a process for conversion of oxygenates to olefins (paragraph [0001]) comprising the following steps (see Figure 3 and corresponding paragraph [0022]):
a) mixing a feed substream 28 comprising oxygenates (first oxygenate) and a recycle stream 39 comprising C2 and C4+ olefins (recycled ethylene, butenes, and pentenes instant claim 87) and passing them through line 28 to a first bed 24 of a multistage reactor comprising a first, second, and third bed, where the first bed is upstream the second bed, and reacting the oxygenates to form a first reaction mixture (paragraph [0022]). Rothaemel further teaches the reactor is adiabatic (paragraph [0008]) and that the reactor including the first bed has a temperature which is regulated to be 440-520°C (paragraph [0007]), which is within the range of 300-550°C of the first temperature range of instant claim 1.
b) combining the first reaction mixture and a feed substream 29 comprising oxygenates (second oxygenate) and sending the combined stream to the second bed 25 of the reactor, and reacting the stream to form a second reaction mixture (paragraph [0022]). Rothaemel teaches that the entire reactor has a temperature which is regulated to be 440-520°C (paragraph [0007]), and thus the temperature of the second bed is within the range of 300-550°C of the second temperature range of instant claim 1.
c) combining the second reaction mixture and a feed substream 30 comprising oxygenates (third oxygenate) and sending the combined stream to the third bed 26 of the reactor, and reacting the stream to form a third reaction mixture (paragraph [0022]). Rothaemel teaches that the entire reactor has a temperature which is regulated to be 440-520°C (paragraph [0007]), and thus the temperature of the third bed is within the range of 300-550°C of the third temperature range of instant claim 2.
Rothaemel further teaches that the oxygenates in the feed (first and second oxygenate) can be methanol and/or dimethyl ether (paragraph [0001]). When the oxygenates only include dimethyl ether, as explicitly taught by Rothaemel, methanol is not introduced into the reactor upstream of the first reaction stage, as claimed in instant claim 1, the first and second oxygenate are the same, as in instant claim 22, and the at first and second oxygenates do not comprise methanol, as in instant claim 64.
With regard to claims 3, 4, 7, 8, and 89, Rothaemel does not show any heating or cooling means inside or outside the multistage reactor of Figure 3, other than a cooler for the third reaction mixture effluent after exiting the reactor. Thus, Rothaemel teaches that external heat is not added to the multistage reactor during or between reaction stages as claimed in instant claim 3, heat is not removed from the multistage reactor during or between reaction stages as claimed in instant claim 4, heat is not removed from the first reaction mixture as in instant claim 7, and heat is not removed from the second reaction mixture prior to being mixed with the third input feed as in instant claims 8 and 89.
With regard to claim 5, Rothaemel teaches passing the first reaction mixture and second reaction mixture directly to the next bed in sequence (Figure 3). Thus, Rothaemel teaches that the first and second reaction mixtures are not removed from the adiabatic multistage reactor, as claimed.
With regard to claim 50, Rothaemel teaches heating the feed stream comprising the oxygenates before splitting and introducing the substreams into the reactor (paragraph [0022])
With regard to claim 76, Rothaemel teaches a system comprising the reactor of Figure 3 (paragraph [0022] and Figure 3), which is a system comprising the multistage adiabatic reactor of claim 1 as claimed.
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, 2, 10, 22, 24, 27, 28, 50, 64, 76, 77, and 87 are rejected under 35 U.S.C. 103 as being unpatentable over Taheri et al. (US 2013/0178674) in view of Graziani et al. (US 4,542,252).
With regard to claims 1, 2, 22, 24, 27, 28, 64, 77, and 87, Taheri teaches a process for dehydration of ethanol to ethylene (paragraph [0002]) comprising the following steps (see Figure 1 and corresponding paragraphs [0023]-[0027]) in a multistage adiabatic reactor (paragraphs [0015]-[0017]):
a) splitting a stream 1 comprising ethanol to produce a stream 3 comprising ethanol (first oxygenate instant claims 1 and 77) which enters the first reaction stage 6A and reacts to produce a first effluent stream 10 (first reaction mixture) (paragraph [0025]). The temperature in reaction stage 6A ranges from 300-550°C (paragraph [0025]), which is identical to the first temperature range of 300-550°C of instant claims 1 and 77.
b) passing the effluent stream 10 and a second stream 8 comprising ethanol (second oxygenate) to the second stage 6B and reacting to produce an second effluent 15 (second reaction mixture) (paragraph [0026]). The temperature in second stage 6B ranges from 300-530°C (paragraph [0026]), which is within the second temperature range of 300-550°C of instant claims 1 and 77.
c) passing the effluent stream 15 and a third stream 13 comprising ethanol (third oxygenate) to the third stage 6C and reacting to produce a third effluent 19 (third reaction mixture (paragraph [0027]). The temperature in third stage 6C ranges from 290-520°C (paragraph [0027]), which overlaps the range of 300-550°C of instant claim 2, rendering the range prima facie obvious.
Taheri teaches the feed stream comprises hydrous or anhydrous ethanol, and is silent regarding the presence of any other oxygenates (paragraph [0024]). Thus, the first and second oxygenates do not comprise methanol and as such methanol is not introduced to the reactor upstream of the first reaction stage as in instant claims 1 and 64, the first and second oxygenates are the same (instant claim 22), and the first and second oxygenates comprise a predominant oxygenate which is ethanol, where ethanol is present in a greater weight percent than any other oxygenate in the first and second oxygenates, as in instant claims 24, 27, 28, and 77.
Taheri does not specifically teach adding an olefin stream to the feed to the first reaction zone.
Graziani teaches a process for conversion of lower aliphatic alcohols to olefins (column 1, lines 8-10) in a multi-stage adiabatic reactor (column 2, lines 3-4). Graziani teaches the process comprises feeding a light olefin along with the alcohol feed in order to improve reactor stability and controllability of the process (column 4, lines 40-43 and 55-56), where the alcohol feed can include ethanol and the olefin cofeed is produced in-situ during the process and recycled (column 14, lines 54-57).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to recycle a portion of the ethylene produced in the process of Taheri as olefin cofeed (one or more first olefins which is recycled ethylene instant claims 1, 77, and 87) as taught by Graziani, because each of Taheri and Graziani teach conversion of oxygenates including ethanol to olefins including ethylene, and Graziani teaches that recycle of olefins produced in the process as olefin cofeed improves reactor stability and controllability of the process (column 4, lines 40-43 and 55-56).
With regard to claim 10, Taheri teaches the process has a 99% selectivity to ethylene (paragraph [0030]). Thus, the olefin present in the product is understood to be predominantly ethylene. Graziani teaches recycling an olefin produced in the process as olefin cofeed, where the olefin can be ethylene (column 15, lines 42-45 and 54-57). Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention that the first olefin is predominantly ethylene, as claimed, because Graziani teaches producing and recycling an olefin from the process which can be ethylene, and Taheri teaches that the product olefin is predominantly ethylene.
With regard to claim 50, Taheri teaches heating the ethanol feed before splitting the feed and introducing into the reactor (paragraph [0024]).
With regard to claim 76, Taheri teaches a system comprising the multistage adiabatic reactor (Figure 1), which is a system comprising the multistage adiabatic reactor of claim 1 as claimed.
Claim 30 is rejected under 35 U.S.C. 103 as being unpatentable over Rothaemel et al. (US 2010/0234655) or Taheri et al. (US 2013/0178674) in view of Graziani et al. (US 4,542,252) as applied to claim 1 above, and further in view of Ramello et al. (WO 2010/097175, cited on IDS of 06/11/2024).
With regard to claim 30, Rothaemel teaches the process above, where the multi-stage adiabatic reactor produces a product comprising C2-C4 olefins (Abstract) and Taheri teaches that the process having the multi-stage adiabatic reactor is 99% selective to ethylene (C2 olefin).
Rothaemel or Taheri fails to teach passing the product from the multi-stage reactor to a single stage reactor comprising one or more catalysts and producing an output stream comprising one or more product olefins.
Ramello teaches a process for producing liquid hydrocarbons comprising olefins, where the process comprises passing an oxygenate feed comprising alcohols to a first reactor to produce light olefins, and then feeding the product from the first reactor directly to a second reactor comprising a catalyst to produce heavy olefins (page 24, claim 1). Ramello teaches the second reactor is a tubular reactor comprising a fixed catalyst bed (page 15, line 12). Thus, the second reactor is a single stage reactor comprising a catalyst, as claimed. Ramello further teaches the product comprising olefins is desirable for making fuels such as gasoline, kerosene, and diesel (page 15, lines 2-5).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to pass the product from the adiabatic reactor of Rothaemel or Taheri to the second reactor of Ramello, because each of Rothaemel, Taheri, and Ramello teaches producing light olefins from alcohols in a reactor, and Ramello teaches that passing the product directly to a second reactor provides a product comprising olefins which is useful for making desirable fuels including gasoline, kerosene, and diesel (page 15, lines 2-5).
Claims 67 and 72 are rejected under 35 U.S.C. 103 as being unpatentable over Coupard et al. (US 2015/0368215) in view of Buchold et al. (US 2011/0288358).
With regard to claims 67 and 72, Coupard teaches a process comprising dehydration of ethanol to ethylene in two adiabatic reactors (multistage adiabatic reactor) (paragraph [0070]) comprising the following steps:
a) providing an ethanol feed to the first reactor (paragraph [0075]), where the ethanol feed comprises 35 wt% or more ethanol (paragraph [0027]) and an additional alcohol which is methanol in an amount of less than 10 wt% (paragraph [0029]) (first oxygenate comprising ethanol and methanol, where the first oxygenate comprises predominantly ethanol). Coupard further teaches reacting the ethanol with the catalyst bed in the reactor at a temperature from 340-500°C (paragraphs [0075]-[0076]), which is within the first temperature range of 300-550°C of instant claim 67.
b) providing the effluent from the first reactor to a second adiabatic reactor and contacting the second catalyst bed at a temperature of 340-500°C (paragraphs [0077]-[0078]), which is within the second temperature range of 300-550°C of instant claim 67.
Coupard fails to teach adding a second oxygenate to the first effluent when passing it to the second catalyst bed, where the oxygenate is methanol, ethanol or a combination thereof.
Buchold teaches a process for conversion of methanol and ethanol in an adiabatic multistage reactor (Abstract). Buchold further teaches that adding ethanol (second oxygenate instant claims 67 and 72) to each reaction stage allows the conversion of ethanol to take place without any further reaction to undesired secondary products (paragraph [0014]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to add the feed of Coupard comprising ethanol to each reactor in the adiabatic series, as claimed, because each of Coupard and Buchold teaches the reaction of ethanol and methanol to olefins in an adiabatic multistage reactor, and Buchold teaches that passing the ethanol to each reaction stage allows the conversion to take place without further reaction to undesired secondary products (paragraph [0014]).
Claim 88 is rejected under 35 U.S.C. 103 as being unpatentable over Coupard et al. (US 2015/0368215) in view of Buchold et al. (US 2011/0288358) as applied to claim 67 above, and further in view of Graziani et al. (US 4,542,252).
With regard to claim 88, Coupard in view of Buchold teaches the method above.
Coupard in view of Buchold does not specifically teach adding a first olefin to the oxygenated feed.
Graziani teaches a process for conversion of lower aliphatic alcohols to olefins (column 1, lines 8-10) in a multi-stage adiabatic reactor (column 2, lines 3-4). Graziani teaches the process comprises feeding a light olefin along with the alcohol feed in order to improve reactor stability and controllability of the process (column 4, lines 40-43 and 55-56), where the alcohol feed can include ethanol and the olefin cofeed is produced in-situ during the process and recycled (column 14, lines 54-57).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to recycle a portion of the ethylene produced in the process of Taheri as olefin cofeed (one or more first olefins instant claim 88) as taught by Graziani, because each of Coupard and Graziani teach conversion of oxygenates including ethanol to olefins including ethylene, and Graziani teaches that recycle of olefins produced in the process as olefin cofeed improves reactor stability and controllability of the process (column 4, lines 40-43 and 55-56).
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.
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, In Suk Bullock can be reached at 571-272-5954. 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.
/Alyssa L Cepluch/Examiner, Art Unit 1772
/Renee Robinson/Primary Examiner, Art Unit 1772
Prosecution Insights