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 amendment filed by applicants on March 2, 2026. In light of the amendment, the examiner has withdrawn the rejection(s) of record. However, the following new rejection is being made.
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.
Claim(s) 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Bartish (US 4,230,641) in view of del Rio et al. (J. Chem. Soc., Dalton Trans., 2001)
The claims are drawn to a process for preparing an aldehyde by hydroformylation of anolefin in the presence of a solvent and a transition metal-based catalyst composition comprising at least one bisphosphine ligand represented by general formula (1). Further limitations limit the ligand used in the present invention to specific stereoisomers and to the aldehyde product having a specific iso-selectivity.
Bartish teaches a process for the hydroformylation of olefins, e.g., propylene, to form saturated aldehydes, wherein the catalyst used is a complex of a chelating phosphine ligand and a rhodium compound (abstract). For example, the reference teaches a process for the hydroformylation of 1-octene, and propylene, respectively, wherein the olefin is reacted in toluene (solvent), a rhodium compound, and phosphine ligand, at a temperature of 91°C. The reference further teaches that bis(diphenylphosphino) propane (dpp), and bis (diphenyl phosphino) pentane are used as phosphine ligand (example 1, table 1, example 3, table 5). .
The ligands used in the process taught by Bartish, e.g., dpp, appear to be racemates of the specific ligands. A person having ordinary skill in the art would have known that a racemic compound comprises a mixture of stereoisomers, and such as person would know how to resolve/isolate a particular stereoisomer, if so desired.
With regard to the iso-selectivity of the aldehyde produced, the reference teaches that the selectivity to the normal isomer decreases with increased solvent polarity; selectivity to the normal isomer also decreases with increasing temperature and rate of reaction (col. 4, lines 12-45). Therefore, a person having ordinary skill in the art would have been able to adjust reaction parameters such as temperature, reaction rate, and/or solvent polarity, in order to arrive at a product having a desired distribution of normal and/or iso-aldehydes.
The claims as amended teach that R1 is selected from substituted and unsubstituted alkyl groups containing 1-20 carbon atoms, meaning that the alkyl groups linking the two phosphorus atoms are substituted at least at the carbon atoms directly linked to phosphorus.
Bartish does not expressly teach this limitation. For example, one of the ligands taught, bis (diphenyl phosphino) pentane may present as an unsubstituted pentane linking the two phosphorus atoms. However, del Rio et al. teach diphosphine rhodium systems in asymmetric hydrogen formulation of styrene, wherein one ligand used with the rhodium-based catalyst is [(2S,4S)-bis(diphenylphosphino) pentane], BDPP, wherein the ligand contains a propyl linking group substituted by methyl groups at the 1- and 3- position (scheme 3). The instant claims are therefore rendered obvious by the reference’s teachings since del Rio et al. teach that a ligand having bis (diphenyl phosphino) pentane as a structure, includes a compound that has methyl-substituted linking groups.
Claim limitations wherein R2 are methyl are deemed obvious, absent unexpected results, as a person having ordinary skill in the art would reasonably expect the rhodium-bisphosphine ligand catalyst composition to effectively catalyze the hydroformylation reaction regardless of the substitution on the alkyl groups linking the two phosphorus atoms of the ligand together.
Response to Arguments
Applicant’s arguments with respect to claim(s) 1-20 have been considered but are moot because the new ground of rejection relies on a combination of references not relied on in the prior rejection of record.
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 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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/SIKARL A WITHERSPOON/Primary Examiner, Art Unit 1692
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