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 1-4 and 6-8 are pending and under current examination.
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 1-4 and 6-7 are rejected under 35 U.S.C. 103 as being unpatentable over Yokomori (US6365783B1).
Determining the scope and contents of the prior art
Yokomori teaches a process of making aldehydes comprising reacting monoolefins, (branched or straight chain with 3-20 C atoms (encompass diisobutene), such as butene, isobutene, 3,4 dimethylhexene, 2,3,4-trimethylpentene, 2,3,5 trimethylhexene (isomer of diisobutene)) with CO and H2 in presence of cobalt based catalyst comprising:
Stage 1-allowing above reaction until a conversion reaches 50-90% with examples allowing 75% reaction and conversion to aldehyde;
Step 2- separating unreacted olefin from a reaction product in the first stage;
And Stage 2-a step of allowing unreacted olefin to react with CO and H2 in the presence of cobalt based catalyst at concentration (24g containing ~90%monoolefin and ~10%paraffins; 24g-2.4g=21.6g monoolefin =21.6g/1000 =0.0216 Kg and 0.08g of cobalt catalyst; thus cobalt catalyst concentration based on monoolefin g/Kg= 0.08g/0.0216Kg=3.703g/Kg=y) (meets limitation of y) and at temperature 120C (less than 180C) (meets limitation of x of the instant claims 2, 3, 6 and 7).
The cited prior art further provides advantage of carrying the process in two stages is to suppress production of alcohol and/or improving aldehyde/alcohol production ratio with several examples (entire patent, especially abstract, col 3-14, examples 1-5 and claims).
Ascertaining the differences between the prior art and the claims at issue
Yokomori teaches process of making aldehydes comprising reacting monoolefins, (branched or straight chain with 3-20 C atoms (encompass diisobutene), such as butene, isobutene, 3,4 dimethylhexene, 2,3,4-trimethylpentene, 2,3,5 trimethylhexene (isomer of diisobutene)) with CO and H2 in presence of cobalt based catalyst, with same reaction conditions, stages, and catalyst as in the instant claims with improvement in aldehyde/alcohol production ratio but fails to teach example wherein the olefin used is diisobutene, DIB.
Resolving the level of ordinary skill in the pertinent art
With regards to the above difference, Yokomori teaches process of making aldehydes comprising reacting monoolefins, (branched or straight chain with 3-20 C atoms (encompass diisobutene), such as butene, isobutene, 3,4 dimethylhexene, 2,3,4-trimethylpentene, 2,3,5 trimethylhexene (isomer of diisobutene)) with CO and H2 in presence of cobalt based catalyst, with same reaction conditions, stages, and catalyst as in the instant claims with improvement in aldehyde/alcohol production ratio. Thus, with the guidance provided by the cited prior art, it would have been prima facie obvious to a person of ordinary skill in the art with a reasonable expectation of success that any monoolefin, branched or straight chain with 3-20 C atoms, may undergo reaction as taught by the cited prior art. Further, the cited prior art provides examples of reaction of 2,3,5 trimethylhexene (isomer of diisobutene), which further make prima facie obvious to a person of ordinary skill in the art with a reasonable expectation of success that DIB may reacts in similar manner. Importantly, a person of ordinary skill in the art would have been motivated to use process of the cited prior art to make aldehyde to reduce alcohol side product and to achieve selectivity in the process.
Additionally, Case law has established that it is prima facie obvious to substitute one known element for another to obtain predictable results. KSR Int'I Co. v. Teleflex, Inc., 550 U.S. 398 (2007).
Case law has also established that it is prima facie obvious to simply employ a different starting material in a generally old reaction. In re Farkas and Sorm 152 USPQ 109 (1966).
Further, compounds which are position isomers (com-pounds having the same radicals in physically differ-ent positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In reWilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious).
Based on the above established facts, it appears that the 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 modified the elements as claimed by known methods with no change in their respective functions, and the modification 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, Yokomori teaches process of making aldehydes comprising reacting monoolefins, (branched or straight chain with 3-20 C atoms (encompass diisobutene), such as butene, isobutene, 3,4 dimethylhexene, 2,3,4-trimethylpentene, 2,3,5 trimethylhexene (isomer of diisobutene)) with CO and H2 in presence of cobalt based catalyst, with same reaction conditions, stages, and catalyst as in the instant claims with improvement in aldehyde/alcohol production ratio.
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. Further, there is a reasonable expectation of success that any olefin with 3-20 carbon atoms and/or any isomer of diisobutylene may be used as starting material and can be made by teachings 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.
Claims 1-4 and 6-8 are rejected under 35 U.S.C. 103 as being unpatentable over Yokomori (US6365783B1) and Springer (US 2007/0265467 A1) in combination.
Determining the scope and contents of the prior art
Yokomori teaches a process of making aldehydes comprising reacting monoolefins, (branched or straight chain with 3-20 C atoms (encompass diisobutene), such as butene, isobutene, 3,4 dimethylhexene, 2,3,4-trimethylpentene, 2,3,5 trimethylhexene (isomer of diisobutene)) with CO and H2 in presence of cobalt based catalyst comprising:
Stage 1-allowing above reaction until a conversion reaches 50-90% with examples allowing 75% reaction and conversion to aldehyde;
Step 2- separating unreacted olefin from a reaction product in the first stage;
And Stage 2-a step of allowing unreacted olefin to react with CO and H2 in the presence of cobalt based catalyst at concentration (24g containing ~90%monoolefin and ~10%paraffins; 24g-2.4g=21.6g monoolefin =21.6g/1000 =0.0216 Kg and 0.08g of cobalt catalyst; thus cobalt catalyst concentration based on monoolefin g/Kg= 0.08g/0.0216Kg=3.703g/Kg=y) (meets limitation of y) and at temperature 120C (less than 180C) (meets limitation of x of the instant claims 2, 3, 6 and 7).
The cited prior art further provides advantage of carrying the process in two stages is to suppress production of alcohol and/or improving aldehyde/alcohol production ratio with several examples (entire patent, especially abstract, col 3-14, examples 1-5 and claims).
Ascertaining the differences between the prior art and the claims at issue
Yokomori teaches process of making aldehydes comprising reacting monoolefins, (branched or straight chain with 3-20 C atoms (encompass diisobutene), such as butene, isobutene, 3,4 dimethylhexene, 2,3,4-trimethylpentene, 2,3,5 trimethylhexene (isomer of diisobutene)) with CO and H2 in presence of cobalt based catalyst, with same reaction conditions, stages, and catalyst as in the instant claims with improvement in aldehyde/alcohol production ratio but fails to teach example wherein the olefin used is diisobutene, DIB; and oxidation of obtained aldehyde to acid.
Resolving the level of ordinary skill in the pertinent art
With regards to the above difference of DIB, Yokomori teaches process of making aldehydes comprising reacting monoolefins, (branched or straight chain with 3-20 C atoms (encompass diisobutene), such as butene, isobutene, 3,4 dimethylhexene, 2,3,4-trimethylpentene, 2,3,5 trimethylhexene (isomer of diisobutene)) with CO and H2 in presence of cobalt based catalyst, with same reaction conditions, stages, and catalyst as in the instant claims with improvement in aldehyde/alcohol production ratio. Thus, with the guidance provided by the cited prior art, it would have been prima facie obvious to a person of ordinary skill in the art with a reasonable expectation of success that any monoolefin, branched or straight chain with 3-20 C atoms, may undergo reaction as taught by the cited prior art. Further, the cited prior art provides examples of reaction of 2,3,5 trimethylhexene (isomer of diisobutene), which further make prima facie obvious to a person of ordinary skill in the art with a reasonable expectation of success that DIB may reacts in similar manner. Importantly, a person of ordinary skill in the art would have been motivated to use process of the cited prior art to make aldehyde to reduce alcohol side product and to achieve selectivity in the process.
Additionally, Case law has established that it is prima facie obvious to substitute one known element for another to obtain predictable results. KSR Int'I Co. v. Teleflex, Inc., 550 U.S. 398 (2007).
Case law has also established that it is prima facie obvious to simply employ a different starting material in a generally old reaction. In re Farkas and Sorm 152 USPQ 109 (1966).
Further, compounds which are position isomers (com-pounds having the same radicals in physically differ-ent positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In reWilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious).
With regards to the above difference of oxidation of aldehyde to acid-, Yokomori teaches process of making aldehydes comprising reacting monoolefins, (branched or straight chain with 3-20 C atoms (encompass diisobutene), such as butene, isobutene, 3,4 dimethylhexene, 2,3,4-trimethylpentene, 2,3,5 trimethylhexene (isomer of diisobutene)) with CO and H2 in presence of cobalt based catalyst, with same reaction conditions, stages, and catalyst as in the instant claims with improvement in aldehyde/alcohol production ratio. The deficiency of oxidation of obtained aldehyde by process taught by Yokomori is cured by Springer.
In same field of endeavor, Springer discloses a process for producing 3,5,5-dimehylhexanoic acid (also known as isononanoic acid) comprising oxidation of 3,5,5-dimehylhexanal, especially wherein the starting material 3,5,5-dimehylhexanal is obtained as a reaction product of oxo/hydroformylation process of diisobutylene (encompass process as in the instant claim 1) (entire application, especially abstract, page 5-7, paragraphs 0057, 0114-0136) example 2 and claims).
Thus, with the guidance provided by Yokomori and Springer, it would have been prima facie obvious to a person of ordinary skill in the art with a reasonable expectation of success that aldehyde obtained by any oxo/hydroformylation process, including Yokomori’s process, may be oxidized further to obtain corresponding acid. Thus, the cited prior art meets limitation of the instant claims.
Based on the above established facts, it appears that the 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, Yokomori teaches process of making aldehydes comprising reacting monoolefins, (branched or straight chain with 3-20 C atoms (encompass diisobutene), such as butene, isobutene, 3,4 dimethylhexene, 2,3,4-trimethylpentene, 2,3,5 trimethylhexene (isomer of diisobutene)) with CO and H2 in presence of cobalt based catalyst, with same reaction conditions, stages, and catalyst as in the instant claims with improvement in aldehyde/alcohol production ratio. Springer discloses a process for producing 3,5,5-dimehylhexanoic acid (also known as isononanoic acid) comprising oxidation of 3,5,5-dimehylhexanal, especially wherein the starting material 3,5,5-dimehylhexanal is obtained as a reaction product of oxo/hydroformylation process of diisobutylene. Thus, combination reads instant 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. Further, there is a reasonable expectation of success that any olefin with 3-20 carbon atoms and/or any isomer of diisobutylene may be used as starting material and can be made by teachings 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.
Response to Arguments
Applicant’s remarks and amendment, filed on 02/17/2026, have been fully considered but not found persuasive.
Applicant argued that objective of the cited prior art is different from the instant claims:
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This is not found persuasive and the instant claims stand rejected. This is because (1) Yokomori teaches same method of making aldehyde including the steps as in the instant claims and thus objective, such as improving production of aldehyde or suppressing production of alcohol of claims 6 and 7 is expected to be achieved; (2) Importantly, Yokomori not only teaches same method of making aldehyde including the steps as in the instant claims but also objective of improving production of aldehyde or suppressing production of alcohol of claims 6 and 7. Just because the title states “Process of producing alcohol”, doesn’t implies that the cited prior art only teaches production of alcohol. In fact, the cited prior art teaches objective of improving production of aldehyde or suppressing production of alcohol of claims 6 and 7 with examples:
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Applicant argued that starting olefin DIB is not taught by the cited prior art.
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This is not found persuasive and the instant claims stand rejected. This is because (1) the cited prior teaches same method of making aldehyde as in the instant claims; (2) Yokomori teaches process of making aldehydes comprising reacting monoolefins, (branched or straight chain with 3-20 C atoms (encompass diisobutene), such as butene, isobutene, 3,4 dimethylhexene, 2,3,4-trimethylpentene, 2,3,5 trimethylhexene (isomer of diisobutene)) with CO and H2 in presence of cobalt based catalyst, with same reaction conditions, stages, and catalyst as in the instant claims with improvement in aldehyde/alcohol production ratio. Thus, with the guidance provided by the cited prior art, it would have been prima facie obvious to a person of ordinary skill in the art with a reasonable expectation of success that any monoolefin, branched or straight chain with 3-20 C atoms, may undergo reaction as taught by the cited prior art. Further, the cited prior art provides examples of reaction of 2,3,5 trimethylhexene (isomer of diisobutene), which further make prima facie obvious to a person of ordinary skill in the art with a reasonable expectation of success that DIB may reacts in similar manner. Importantly, a person of ordinary skill in the art would have been motivated to use process of the cited prior art to make aldehyde to reduce alcohol side product and to achieve selectivity in the process.
Additionally, Case law has established that it is prima facie obvious to substitute one known element for another to obtain predictable results. KSR Int'I Co. v. Teleflex, Inc., 550 U.S. 398 (2007).
Case law has also established that it is prima facie obvious to simply employ a different starting material in a generally old reaction. In re Farkas and Sorm 152 USPQ 109 (1966).
Further, compounds which are position isomers (com-pounds having the same radicals in physically differ-ent positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In reWilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious).
Thus, teaching of Yokomori enables a person of ordinary skill in the art with a reasonable expectation of success that isomer of 2,3,5 trimethylhexene (such as diisobutene DIB), may react in same manner and preferentially provide aldehyde as taught by the cited prior art; (3) if the cited prior art would have provided DIB, the rejection would have been anticipation and not obviousness rejection; (4) Further, case law has established that it is prima facie obvious to simply employ a different starting material in a generally old reaction. In re Farkas and Sorm 152 USPQ 109 (1966).
Applicant argued that DIB unexpectedly produces less alcohol.
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This is not found persuasive and the instant claims stand rejected. This is because applying different starting material and obtaining different result is not unexpected but expected.
Rest of applicant’s argument is moot in view of new rejection as set forth above.
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.
Conclusion
No Claim is allowed.
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/PANCHAM BAKSHI/Primary Examiner, Art Unit 1623
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