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 .
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) 1-15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Dong et al. (US 9,725,398).
The claims are drawn to a process comprising initially charging an olefin; adding a ligand of formula (I); adding a compound comprising Pd; adding an alcohol; feeding carbon monoxide and hydrogen, wherein the pressure of hydrogen is at least 0.6 MPa (6 bar); heating the reaction mixture to convert the olefin to an ester.
Dong et al. teach an alkoxycarbonylation reaction, wherein an olefin is added to a solution comprising a disphosphine ligand and a Pd compound, the ligand is preferably a compound of formula (1); adding an alcohol, feeding carbon monoxide, and then heating the reaction mixture to convert the olefin to an ester. The alcohol is preferably methanol or ethanol. Carbon monoxide is fed at a partial pressure of between 0.1 and 10 MPa (1 to 100 bar). The process is conducted with the addition of an acid, preferably a Bronsted or Lewis acid. Suitable Bronsted acids include, inter alia, p-toluenesulfonic acid, PTSA (col. 5, line 46 to col. 6, line 55; col. 9, line 25 to col. 11, line10).
Dong et al. further teaches that the alkoxycarbonylation reaction may be conducted in the presence of small amounts of hydrogen. As an example, the reference teaches methoxycarbonylation of ethene using ligand 1, wherein a reactor is charged with Pd(acac)2, ligand 1, PTSA, and methanol. Ethene is then transferred into the reactor, followed by the introduction of hydrogen (3 bar) and carbon monoxide (30 bar). The reaction is conducted at 80°C for 20 hours, thereby producing methyl propionate at a 99% yield (col. 23, lines 1-22).
The difference between Dong et al. and the present invention is that the reference teaches hydrogen being added to the reaction at a pressure of 3 bar, while the present invention feeds hydrogen to the reaction at a pressure of at least 6 bar.
The examiner does not find that this difference represents a patentable distinction, absent a showing of some unexpected result. Dong et al. teaches that the alkoxycarbonylation reaction may be conducted in the presence of small amounts of hydrogen. The reference teaches feeding hydrogen at 3 bar of pressure and ultimately produces an ester at a 99% yield. The examiner therefore finds that the instant claims are rendered obvious over Dong et al., as a person having ordinary skill in the art would adjust the pressures of hydrogen and carbon monoxide fed to the alkoxycarbonylation reactor through routine experimentation in an effort to obtain desirable yields of the ester product.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SIKARL A WITHERSPOON whose telephone number is (571)272-0649. The examiner can normally be reached M-F 9am-9pm IFP.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/SIKARL A WITHERSPOON/Primary Examiner, Art Unit 1692
Prosecution Insights