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 .
Status of the Application
Claims 1-14 are pending and under current examination.
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 1-14 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 pre-AIA the applicant regards as the invention.
Claims 1-14 are indefinite as:
Claim 1 recites “a process for recovering---direct esterification---distillation---said process”. This is because it is unclear which process applicant refers in “said process”. Is it a recovery process or esterification process or distillation.
Claim 1 is indefinite as the claim recites “the esterification reaction”, which lacks antecedent basis.
Claim 1 is further indefinite as it is unclear if purification column is same as distillation column and where is such purification column present. Is it present before distillation column and what is fed to such purification column.
Claim 2 is indefinite as the claim lacks antecedent basis for said recycled cracking products.
Claim 4 is indefinite as the claim recites “drawn off laterally” whereas claim 1 recites side outlet. Applicant is suggested to keep same terminology in the entire set of claims.
Claim 4 is also indefinite as the claim recites “is recycled to a distillation column” and it is unclear if this distillation column is same as referred in claim 1 or different and if different where this column is present considering that the stream is recycled.
Claim 5 is indefinite as the instant claim first recites in step (ii) what has been done with the bottom stream and then recites completely different step (iii) what is done with the bottom stream.
Claim 5 is indefinite as the claim lacks antecedent basis for the evaporator.
Claim 6 is indefinite as the claim recites “drawn off laterally”, which lacks antecedent basis.
Claim 7 is indefinite as the claim recites cracker head stream. However, claim 5 recites at top, a stream and at bottom, a stream from cracker. Applicant is suggested to keep same terminology in entire set of claims.
Claim 7 is indefinite as the claim recites “the side drawn off washing step”, which lacks antecedent basis.
Claim 10, 11 and 12 are indefinite as these claims recite cracker head products. However, claim 5 recites at top, a stream and at bottom, a stream from cracker. Applicant is suggested to keep same terminology in entire set of claims.
Claim 10 is indefinite as the claim recites evaporator head products. It is unclear where the evaporator is present and its head products.
Since the dependent claims doesn’t cure the above deficiencies, these claims are also indefinite.
Appropriate correction required.
Claim Rejections - 35 USC § 102
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 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 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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-4 and 13-14 are rejected under 35 U.S.C. 102(a)(1) and 102 (a)(2) as being anticipated by Yada (US 20040267045 A1).
Yada discloses a process for producing C4-C10 acrylic ester, such as n-butyl acrylate, 2-ethylhexyl acrylate, free of acidic impurities by direct esterification of acrylic acid with an alcohol followed by recovery/purification and further comprising a thermal (pyrolysis/cracking process) process comprising:
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Subjecting the esterification crude reaction mixture obtained from a direct esterification process to a acrylic acid separation column (a distillation column) with a side draw off for acrylic acid rich stream originating from the esterification reaction, which is recycled to the esterification reactor; at the top a stream comprising unreacted reagents, such as alcohol and at the bottom a stream comprising desired ester and heavy byproducts
subjecting the bottom stream to heavy matter separation column (distillation column), wherein top stream comprising light compounds recycled to esterification reactor and at bottom heavy matters; part of heavy byproducts is eliminated;
and rest of heavy matters separated through the bottom of the purification column of (ii) is supplied to thermal (high boiling) decomposition reactor (cracker) and decomposed leading to cracking products or decomposition products; the decomposition products are separated by an evaporator or distillation column to separate at the top stream of value, which is recycled to the esterification reactor and a bottom stream residue stream eliminated or sent for further treatment (entire application, especially abstract, Figures 2 and 3; 0006-0068, 0129-0208 and Examples 1-14).
The cited prior art further teaches that part of the steam (equivalent to stream drawn off laterally) comprising unreacted reagent and ester is subjected to an extraction column with an aqueous stream:
-producing an aqueous phase comprising alcohol, acidic impurities and the aqueous phase subjected to further treatment for separation of alcohol and recycling of alcohol;
- and an organic phase comprising desired ester and heavy products and traces of reagents is subjected to low-boiling separation column (distillation column), wherein a part of low-boiling separated from the top is circulated in the process and the crude acrylic ester is subjected to acrylic ester purification column, wherein acrylic acid having high purity is separated from the column top and the bottom comprising acrylic acid is circulated in the process (entire application, especially abstract, Figures 2 and 3; 0006-0068, 0129-0208 and Examples 1-14). The cited prior art further discloses recycled cracking products as olefins, such as beta-acryloxypropionic acid etc. The cited prior art discloses that cracker reactor or thermolysis or pyrolysis reactor is tubular reactor or a jacketed stirrer reactor and the decomposition is carried out at 160C, 200C etc. in presence or absence of catalyst (entire application, especially abstract, Figures 2 and 3; 0006-0068, 0129-0208 and Examples 1-14).
Since the cited prior art reads on all the limitations of the instant claims 1-4 and 13-14, these claims are anticipated.
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 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 of this title, 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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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 1-6, 8, 9 and 13-14 are rejected under 35 U.S.C. 103 as being unpatentable over Moreliere (US20170267624 A1) and Yada (US 20040267045 A1) in combination.
Determining the scope and contents of the prior art
Moreliere teaches an improved process for producing C4-C10 acrylic ester, such as 2-ethylhexyl acrylate, free of acidic impurities by direct esterification of acrylic acid with an alcohol followed by recovery/purification comprising the steps of:
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Which is exactly same steps as step (i) (other than side draw off, a stream rich in acidic impurities) and (ii). The cited prior art also discloses preferred embodiment, wherein step (i) of the cited prior art also adjusted to comprises- side draw off, a stream rich in acidic impurities and a stream drawn off having acid impurities is subjected to washing step and organic phase from this step is recycled into the topping column.
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(entire application, especially paragraphs 0009-0023; 0036-0090, examples and claims).
Yada discloses a process for producing C4-C10 acrylic ester, such as n-butyl acrylate, 2-ethylhexyl acrylate, free of acidic impurities by direct esterification of acrylic acid with an alcohol followed by recovery/purification and further comprising a thermal (pyrolysis/cracking process) process comprising:
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Subjecting the esterification crude reaction mixture obtained from a direct esterification process to a acrylic acid separation column (a distillation column) with a side draw off for acrylic acid rich stream originating from the esterification reaction, which is recycled to the esterification reactor; at the top a stream comprising unreacted reagents, such as alcohol and at the bottom a stream comprising desired ester and heavy byproducts
subjecting the bottom stream to heavy matter separation column (distillation column), wherein top stream comprising light compounds recycled to esterification reactor and at bottom heavy matters; part of heavy byproducts is eliminated;
and rest of heavy matters separated through the bottom of the purification column of (ii) is supplied to thermal (high boiling) decomposition reactor (cracker) and decomposed leading to cracking products or decomposition products; the decomposition products are separated by an evaporator or distillation column to separate at the top stream of value, which is recycled to the esterification reactor and a bottom stream residue stream eliminated or sent for further treatment (entire application, especially abstract, Figures 2 and 3; 0006-0068, 0129-0208 and Examples 1-14).
The cited prior art further teaches that part of the steam (equivalent to stream drawn off laterally) comprising unreacted reagent and ester is subjected to an extraction column with an aqueous stream:
-producing an aqueous phase comprising alcohol, acidic impurities and the aqueous phase subjected to further treatment for separation of alcohol and recycling of alcohol;
- and an organic phase comprising desired ester and heavy products and traces of reagents is subjected to low-boiling separation column (distillation column), wherein a part of low-boiling separated from the top is circulated in the process and the crude acrylic ester is subjected to acrylic ester purification column, wherein acrylic acid having high purity is separated from the column top and the bottom comprising acrylic acid is circulated in the process (entire application, especially abstract, Figures 2 and 3; 0006-0068, 0129-0208 and Examples 1-14). The cited prior art further discloses recycled cracking products as olefins, such as beta-acryloxypropionic acid etc. The cited prior art discloses that cracker reactor or thermolysis or pyrolysis reactor is tubular reactor or a jacketed stirrer reactor and the decomposition is carried out at 160C, 200C etc. in presence or absence of catalyst (entire application, especially abstract, Figures 2 and 3; 0006-0068, 0129-0208 and Examples 1-14).
Ascertaining the differences between the prior art and the claims at issue
Moreliere teaches an improved process for producing C4-C10 acrylic ester, such as 2-ethylhexyl acrylate, free of acidic impurities by direct esterification of acrylic acid with an alcohol followed by recovery/purification comprising the steps same as steps (i) and (ii) and washing steps of the instant claims, but fails to teach processing of bottom stream of the rectification column through thermal decomposition in a cracker.
In the same field of endeavor, Yada discloses a process for producing C4-C10 acrylic ester, such as n-butyl acrylate, 2-ethylhexyl acrylate, free of acidic impurities by direct esterification of acrylic acid with an alcohol followed by recovery/purification and further comprising a thermal (pyrolysis/cracking process) as in the instant claims 1-4 and 13-14, but fails to teach arrangement of the process steps (i) and (ii) of the instant claims 5.
Resolving the level of ordinary skill in the pertinent art
With regards to the above difference-With the guidance provided by Moreliere and Yada, it would have been prima facie obvious to a person of ordinary skill in the art with a reasonable expectation of success that heavy byproducts obtained from Moreliere process may be treated undergo thermal treatment as taught by Yada to produce useful products that may be recycled to the process to increase overall yield of the process as taught by Yada. Further, a person of ordinary skill in the art would have been motivated to combine steps of Yada with Moreliere process to increase yield and to make process more cost effective.
Based on the above established facts, it appears that the combination of teachings of above cited prior art read applicants’ process.
Therefore, all the claimed elements were known in the prior art and one skilled person in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination would have yielded predictable results to one of ordinary skill in the art at the time of the invention.
Considering objective evidence present in the application indicating obviousness or nonobviousness
To establish a prima facie case of obviousness, three basic criteria must be met: (1) the prior art reference must teach or suggest all the claim limitations; (2) there must be some suggestion or motivation, either in the references themselves or in the knowledge generally available to one of ordinary skill in the art, to modify the reference or to combine reference teachings; and (3) there must be a reasonable expectation of success; and (MPEP § 2143).
In this case, Moreliere teaches an improved process for producing C4-C10 acrylic ester, such as 2-ethylhexyl acrylate, free of acidic impurities by direct esterification of acrylic acid with an alcohol followed by recovery/purification comprising the steps same as steps (i) and (ii) and washing steps of the instant claims and Yada discloses a process for producing C4-C10 acrylic ester, such as n-butyl acrylate, 2-ethylhexyl acrylate, free of acidic impurities by direct esterification of acrylic acid with an alcohol followed by recovery/purification and further comprising a thermal (pyrolysis/cracking process) as in the instant claims 1-4 and 13-14).
So, the combination of prior art read applicants claims.
In KSR International Vo. V. Teleflex Inc., 82 USPQ2d (U.S. 2007), the Supreme Court particularly emphasized “the need for caution in granting a patent based on a combination of elements found in the prior art,” (Id. At 1395) and discussed circumstances in which a patent might be determined to be obvious. Importantly, the Supreme Court reaffirmed principles based on its precedent that “[t]he combination of familiar elements according to known methods is likely to be obvious when it does no more than yield predictable results.” (Id. At 1395). See MPEP 2143 - Examples of Basic Requirements of a Prima Facie Case of Obviousness [R-9].
In this case at least prong (E) “Obvious to try” – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success would apply.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense. In that instance the fact that a combination was obvious to try might show that it was obvious under § 103.”KSR, 550 U.S. at ___, 82 USPQ2d at 1397. If any of these findings cannot be made, then this rationale cannot be used to support a conclusion that the claim would have been obvious to one of ordinary skill in the art. It is well within the skill of the organic chemist to recognize the fact that applicants claimed process is nothing but the combination of known individual chemical processes. Further, there is a reasonable expectation of success that cracking step may be included in the process of production of acrylic ester to increase the yield and making process more cost effective and can be made by combination of the above cited prior art.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention by taking the advantage of the teaching of the above cited references and to make the instantly claimed process with a reasonable expectation of success. Modifying such parameters is prima facie obvious because an ordinary artisan would be motivated to develop an alternative process for economic reasons or convenient purposes from a known individual reaction steps, and to arrive applicants process with a reasonable expectation of success, since it is within the scope to modify the process through a routine experimentation.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-6, 8, 9 and 13-14 are rejected under 35 U.S.C. 103 as being unpatentable over Moreliere (US20170267624 A1) and Yada (US 20040267045 A1) in combination.
Claims 1-6, 8, 9 and 13-14 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-19 of U.S. Patent No. 9975842B2 (US20170267624 A1) and over claims 1-10 of U.S. Patent No. 12122746B2 in view of Yada (US 20040267045 A1), discussed in greater detail above. Claims 1-19 of U.S. Patent No. 9975842B2 (US20170267624 A1) and claims 1-10 of U.S. Patent No. 12122746B2 teaches an improved process for producing C4-C10 acrylic ester, such as 2-ethylhexyl acrylate, free of acidic impurities by direct esterification of acrylic acid with an alcohol followed by recovery/purification comprising the steps same as steps (i) and (ii) and washing steps of the instant claims and Yada discloses a process for producing C4-C10 acrylic ester, such as n-butyl acrylate, 2-ethylhexyl acrylate, free of acidic impurities by direct esterification of acrylic acid with an alcohol followed by recovery/purification and further comprising a thermal (pyrolysis/cracking process).
For the reasons set forth above concerning the obviousness that the cracking step may be included in the process of production of acrylic ester of U.S. Patent No. 9975842B2 (US20170267624 A1) and U.S. Patent No. 12122746B2 to increase the yield and making process more cost effective. Thus, the instant claims are obvious.
Conclusion
No Claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to PANCHAM BAKSHI whose telephone number is (571)270-3463. The examiner can normally be reached M-Thu 7-4.30 EST.
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/PANCHAM BAKSHI/Primary Examiner, Art Unit 1623