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 .
The examiner has considered the response filed by applicants on February 4, 2026. Applicant’s arguments were not persuasive; as such, the following rejection has been maintained.
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) 1-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nagy et al. (10,710,004).
The instant claims are drawn to a process for treating an alkyl aromatic oxidate stream used for alkylene oxide production, the process comprising:
PNG
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304
628
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Greyscale
The claims are also drawn to a process for the co-production of an alkene oxide and styrene monomer, starting from the oxidation of ethylbenzene.
Nagy et al. teach a process for upgrading a waste stream in a propylene oxide/styrene co-production process. The waste stream is generated from a POSM process, wherein ethylbenzene is oxidized to form ethylbenzene hydroperoxide (presence of a small amount of alkali may be used to improve oxidation rate and selectivity); the hydroperoxide is reacted with propylene to form propylene oxide and 1-phenyl ethanol. Propylene oxide and 1-phenyl ethanol may be separated, and the latter can be dehydrated to produce styrene monomer. A heavy organic sodium containing low value product stream resulting from such separation processes is used as the waste stream to be treated according to the invention (col. 11, lines 34 to 60).
According to the invention, the waste stream is contacted with water and carbon dioxide, whereby sodium is extracted from the organic stream, followed by separation of an aqueous sodium salt-containing slurry phase from an organic phase comprising a reduced sodium content relative to the organic stream. Contacting the waste stream with water and carbon dioxide mya be done at a temperature in the range of 20 to 100°C, at ambient, or above ambient pressure (col. 5, line 57, to col. 8, line 48). The method may include repeating the contacting (washing) and separating steps one or more times on the organic phase (abstract).
The process taught by Nagy et al. does not actively comprise a step wherein an alkyl aromatic oxidate stream is contacted with an aqueous alkali solution prior to washing and separation cycles in the presence of water and carbon dioxide. However, Nagy et al. teach, by way of reference, that in the POSM process, various distillation steps are employed to separated unreacted reagents, as well as various product streams, and one or more caustic treatment steps may be employed in order to reduce the acidic characteristics of various streams. During such processes, a heavy residue stream containing relatively high amounts of sodium compounds is formed (col. 1, lines 25-40).
In view of this disclosure by Nagy et al., it would have been obvious to a person having ordinary skill in the art that a product stream resulting from a POSM process may undergo a step, wherein the stream is contacted with an aqueous alkali solution, e.g., a caustic solution, in order to reduce any acidic characteristics of such streams, prior to being subjected to the one or more washing steps in the presence of water and carbon dioxide, taught by Nagy et al., for reducing the sodium content in the organic phase of a POSM process.
Response to Arguments
Applicant's arguments filed February 4, 2026 have been fully considered but they are not persuasive. Applicants argue that there is no teaching, suggestion, or motivation in the Nagy reference to support the examiner’s position that it would have been obvious to provide an alkylaromatic oxidate stream comprising (i) an alkyl aromatic hydroperoxide compound, (ii) at least on undesired compound, and (iii) an organic solvent; and then contact such a stream with an aqueous alkali solution to form a mixture.
The examiner respectfully disagrees with applicant’s argument. Nagy et al. teach a process for upgrading a waste stream in a propylene oxide/styrene coproduction process (e.g., a POSM process). A stream from a POSM process would comprise ethylbenzene hydroperoxide, ethylbenzene, propylene oxide, and organic sodium compounds. Nagy et al. does not teach an example wherein such a stream is contacted with an aqueous alkali solution; however, the reference expressly teaches that in the POSM process, one or more caustic treatment steps may be employed to reduce acidic characteristics of various streams (col. 1, lines 32-36), and that in conventional process for removing sodium from waste streams produced in POSM processes, one or more caustic treatment steps are often utilized (col. 4, lines 38-40).
In view of these teachings from Nagy et al., the examiner contends that the rejection of record is proper.
THIS ACTION IS MADE FINAL. 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 SIKARL A WITHERSPOON whose telephone number is (571)272-0649. The examiner can normally be reached M-F 9am-9pm IFP.
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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.
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/SIKARL A WITHERSPOON/Primary Examiner, Art Unit 1692
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