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 .
DETAILED ACTION
Claims 1-6, 8, 9 and 11-22 of M. Abolhasani et al., US 18/577,060 (Jul. 7, 2022) are pending and rejected.
Claim Interpretation
Examination requires claim terms first be construed in terms in the broadest reasonable manner during prosecution as is reasonably allowed in an effort to establish a clear record of what applicant intends to claim. See, MPEP § 2111. Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. See MPEP § 2111.01.
Interpretation of the Claim 1 ‘wherein clauses’
Claim 1 recites the following two ‘wherein’ clauses:
Claim 1 . . .
[first wherein clause]
wherein the contacting of the olefin with the H2 and the CO in the presence of the catalyst solution at:
a temperature ranging from 95 °C to 130 °C,
a carbon monoxide partial pressure (PCO) ranging from 110 psia to 350 psia, and
a hydrogen partial pressure (PH2) ranging from 20 psia to 150 psia,
produces a ratio of linear aldehydes to branched aldehydes (l/b) of less than 1.0; and
[second wherein clause]
wherein the contacting of the olefin with the H2 and the CO in the presence of the catalyst solution at:
a temperature ranging from 60 °C to 100 °C,
a PCO ranging from 5 psia to 150 psia, and
a PH2 ranging from 100 psi a to 350 psia,
produces a l/b of greater than 1.0.
1. The Claimed l/b Ratio
Regarding the claimed l/b ratio, the specification teaches that:
[0068] Generally, in hydroformylation processes, a transition metal-organophosphorus ligand complex catalyst produces an isomeric mixture comprising a linear (l, normal, or n-) aldehyde and one or more branched (b, iso-, or i-) aldehydes. A ratio of the linear aldehyde to the sum of the branched aldehydes, calculated by molar or by weight, is often described as l/b selectivity or l/b ratio. Since all isomeric aldehydes produced from a given olefinically-unsaturated compound have an identical molecular weight, the molar lib ratio is identical to the weight l/b ratio. For the purposes of this disclosure, an l/b selectivity of a catalyst refers to the l/b ratio obtained from hydroformylation of an olefin unless otherwise stated.
Specification at page 13, [0068] (emphasis added).
Similarly, the art teaches that hydroformylation is the catalytic addition of synthesis gas (“syngas”, a mixture of CO and H2) to olefins. R. Franke et al., 112 Chemical Reviews, 5675-5732 (2012) (“Franke”). Franke teaches that the reaction leads to a mixture of isomeric products, n-aldehydes (linear), and isoaldehydes (branched). Franke at page 5675, col. 1. Franke further teaches that because double-bond isomerization of the substrate olefin may occur prior to the hydroformylation, different branched aldehydes can be formed even when a single terminal olefin has been subjected to the reaction. Franke at paragraph bridging pages 5675-5676.
Franke summarizes in Scheme 1:
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Franke at page 5676, col. 1 (Scheme 1). Franke teaches that the ratio of the isomers (regioselectivity) is therefore an important parameter of each hydroformylation. Franke at page 5676, col. 1.
The art teaches that hydroformylation of terminal alkyl-alkenes shows a preference towards linear aldehyde formation, and with the correct ligands, near-perfect linear selectivity can be obtained. L. Iu et al, 58 Angew. Chem. Int. Ed., 2120-2124 (2019) (see page 2120, col. 1). Lu teaches that the industrially important branched aldehyde isobutanal requires the very challenging (branched) isoselective hydroformylation of propene. Id.; see also, P. Dingwall et al., 139 Journal of the American Chemical Society, 15921-15932 (2017) (“[e]xtensive studies, albeit generally devoted to discovering more linear selective catalysts, show that the linear isomer is preferred in nearly every case when alkyl alkenes take the form XCH2CH=CH2 (X can be any carbon chain)”); A. Phanopoulos et al., ACS Catalysis, 5799-5809 (2018) (“[t]o date, few examples of catalyst systems capable of performing branched-selective hydroformylation of nonactivated terminal olefins have been reported”).
2. Broadest Reasonable Interpretation of the Two Claim 1 ‘wherein clauses’
It is noted that all the claim 1 ranges of temperature, PCO and PH2 overlap within one another between the two ‘wherein’ clauses. In any case, the plain meaning of the bolded/underlined conjunction “and” requires that both ‘wherein’ clauses must be satisfied to meet claim 1.
Claim 1 is drafted using ‘wherein’ language rather than standard method-step language. MPEP § 2111.04(I). Claim scope is not limited by claim language that suggests or makes optional but does not require steps to be performed. MPEP § 2111.04(I). The determination of whether a ‘wherein’ clause is a limitation in a claim depends on the specific facts of the case. MPEP § 2111.04(I).
The issue here is whether: (1) both ‘wherein’ clauses are actual physical method steps that both must be practiced to meet claim 1 (i.e., two separate runs of claim 1 are required, at a different temperature, PCO and PH2, each giving a different l/b ratio within the recited range); or (2) the two claim 1 ‘wherein’ clauses are not required method steps, but rather functional language (an intended result) that is achievable by correctly adjusting the temperature, PCO and PH2 of the claimed system, according to the specification guidance.
Here, the practice of each required ‘wherein clause’ necessarily results in a manipulative difference in the claim 1 “contacting” step because a different l/b ratio must result. In this regard, the specification gives specific guidance on adjusting the temperature, PCO and PH2, in the hydroformylation of 1-octene, such that the recited l/b ratio may be obtained. Specification at pages 29-32 (working Example 1).
In view of the foregoing, claim 1 is reasonably interpreted, consistently with the specification, in that both ‘wherein’ clauses are actual physical method steps that both must be practiced to meet claim 1.
That is claim 1 requires two separate runs of:
Claim 1 . . . contacting an olefin with hydrogen (H2) and carbon monoxide (CO) in the presence of a catalyst solution, the catalyst solution comprising: a hydroformylation solvent; a rhodium (Rh) source; and a fluorophosphite ligand of formula (I) . . .
each at the recited temperature, PCO and PH2 of the respective ‘wherein clause’, each separate run giving a l/b ratio within the respective ‘wherein’ clause’s recited range.
The ‘wherein’ clauses of dependent claims 2-5 are similarly interpreted.
Rejections 35 U.S.C. 112(b)
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.
Pursuant to 35 U.S.C. 112, the claim must apprise one of ordinary skill in the art of its scope so as to provide clear warning to others as to what constitutes infringement. MPEP 2173.02(II); Solomon v. Kimberly-Clark Corp., 216 F.3d 1372, 1379, 55 USPQ2d 1279, 1283 (Fed. Cir. 2000). The meaning of every term used in a claim should be apparent from the prior art or from the specification and drawings at the time the application is filed. Claim language may not be ambiguous, vague, incoherent, opaque, or otherwise unclear in describing and defining the claimed invention. MPEP § 2173.05(a).
The Claim 9 and 11 Limitation Rhodium to Ligand Ratio is Unclear
Claims 9 and 11 are rejected pursuant to 35 U.S.C. 112(b), as indefinite because the limitation of the claimed ratio of rhodium to ligand of formula (I) is inconsistent with the specification.
Claim 9 recites:
9. The process of claim 1, wherein the ratio of Rh to the ligand of formula (I) ranges from 10: 1 to 400: 1.
However, the specification teaches the reverse ratio is intended (i.e., ligand to Rh):
[0092] The ratio of gram moles fluorophosphite ligand of formula (I) to gram atoms transition metal may vary over a wide range, e.g., gram mole fluorophosphite:gram atom transition metal ratio of 1 :1 to 400:1. For rhodium-containing catalyst systems, the gram mole fluorophosphite:gram atom rhodium ratio in some aspects of the present disclosure is in the range of 1: 1 to 200: 1 with ratios in the range of 1: 1 to 120: 1.
Specification at page 18, [0092]. This is the reverse of the ratio that is claimed. That claims 9 and 11 incorrectly recite the reverse of the ratio intended is further evidenced by the specification’s working examples; for instance, in working Example 1 “L was added at a 10: 1 L:Rh ratio” (specification at page 29. [00123]); in working Example 2 “The L:Rh ratio was increased to 2000: 1” (specification at page 32, [00129]); in working Examples “a pre-activated Rh/L catalyst at the L:Rh ratio of 40: 1” was employed (specification at page 34, [00137]); see also, data in Table 1 at page 43. In sum, teaches a reverse of the ratio that is set forth in claim 9. Claim 9 is therefore indefinite because the recited ratio does not make sense in view of the specification teachings. Rather, the specification indicates the reverse ratio of claim 9. The same issue is present in claim 11.
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.
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 AIA 35 U.S.C. 103(a) 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.
Claims 1-6, 8, 9 and 11-22 are rejected under AIA 35 U.S.C. 103 as being unpatentable over Y. Liu et al., WO 2009/085160 (2009) (“Liu”) alone or in further in view of T. Puckette et al., US 5,840,647 (1998) (“Puckette”).
Y. Liu et al., WO 2009/085160 (2009) (“Liu”)
Liu discloses fluorophosphite hydroformylation ligands having the structure of formula (I) provide high catalyst activity. Liu at page 4-5, [0010-0012].
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Liu teaches that rhodium is the metal to form the hydroformylation catalyst complexes with the disclosed fluorophosphite ligands. Liu at page 12, [0024].
Liu teaches that the partial pressures of the ratio of the hydrogen to carbon monoxide in the feed can be selected according to the linear: branched isomer ratio desired. Liu at page 15, [0031]. Liu further teaches that with the fluorophosphite ligands described herein, the ratio of linear to branched products can be varied widely by changing the partial pressures of the carbon monoxide in the reactor. Liu at page 15, [0031].
Liu teaches that in the case of propylene, the normal- and iso-butyraldehydes obtained from propylene are in turn converted into many commercially valuable chemical products such as, for example, n-butanol, 2-ethyl-hexanol, n-butyric acid, isobutanol, neo-pentyl glycol, 2,2,4-trimethyl-1,3-pentanediol, and the monoisobutyrate and di-isobutyrate esters of 2,2,4-trimethyl-1,3-pentanediol. Liu at page 1, [0002].
Liu discloses Ligand C (Ethanox 398™) and Ligand D were tested in hydroformylation working Examples.
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Liu at page 19, [0043] (Ligand C)1; Liu at page 20 (Ligand D). Liu ligand D falls within the claimed ligand of Formula (I) for each of claims 1-6, 8, 9, 11-20 and 22. Liu ligand C falls within the claimed ligand of Formula (I) for claims 1-6, 8, 9, 11-19, and 21.
In comparative Examples C1 to C-6 (Ligand C) and Examples 11-13 (Ligand D), Liu teaches hydroformylation of propylene with hydrogen and carbon monoxide in the presence of rhodium/Ligand catalysts complexes to produce butyraldehydes. Liu at pages 21-24 (data in Table 1). Liu teaches that Comparative Examples 1-3 were taken directly from Puckette, Halophosphite Ligands for the Rhodium Catalyzed Low-Pressure Hydroformylation Reaction, in Catalysis of Organic Reactions, 31-38 (S. Schmidt ed., 2006). Liu at page 22, [0047] (see, Puckette at page 35, Table 1). Liu teaches that Comparative Examples 5-6 (Ligand B) and Examples 7-10 (Ligand A) were carried out in the same manner as Comparative Example 4. Liu at page 23, [0051]-[0052]. Liu neglects to state the procedure employed for Examples 11-13 (Ligand D). Liu at page 25, lines 1-4. One of ordinary skill would presume that Examples 11-13 were also carried out in the same manner as Comparative Example 4. Liu Table 1, summarizing the Examples, is reproduced below.
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Liu at page 24 (Table 1). Liu teaches that “Examples 11 through 13 illustrate the desirable nature of Ligand "D". Liu at page 25, line 1. As can be seen from Table 1, the catalyst activity, in case of ligand D, increases as the ratio of ligand to rhodium is increased from 5:1 to 30:1. Liu reports catalyst activity in units of kilograms butyraldehyde/gram of rhodium-hour. Liu at page 24 (Table 1).
Liu’s Table 1 “N/I Ratio” defined as follows:
The ratio of the amount of the normal aldehyde product to the amount of the iso aldehyde product typically is referred to as the normal-to-iso (N:I) or the normal-to-branched (N:B) ratio.
Liu at page 1, [0002]. Liu’s “N/I Ratio” directly corresponds to claim 1’s l/b ratio.
Differences between Liu and Claim 1
Liu differs in not teaching the first claim 1 ‘wherein clause”:
Claim 1 . . . wherein the contacting of the olefin with the H2 and the CO in the presence of the catalyst solution at:
a temperature ranging from 95 °C to 130 °C,
a carbon monoxide partial pressure (PCO) ranging from 110 psia to 350 psia, and
a hydrogen partial pressure (PH2) ranging from 20 psia to 150 psia,
produces a ratio of linear aldehydes to branched aldehydes (l/b) of less than 1.0.
It is noted there that Liu clearly teaches the following claim 1 limitations:
Claim 1. A process for preparing linear and branched aldehydes, the process comprising: contacting an olefin with hydrogen (H2) and carbon monoxide (CO) in the presence of
a catalyst solution, the catalyst solution comprising:
a hydroformylation solvent;
a rhodium (Rh) source; and
a fluorophosphite ligand of formula (I) . . .
Liu also does teach one of ordinary skill the claim 1 second ‘wherein clause’:
claim 1 . . . wherein the contacting of the olefin with the H2 and the CO in the presence of the catalyst solution at:
a temperature ranging from 60 °C to 100 °C,
a PCO ranging from 5 psia to 150 psia, and
a PH2 ranging from 100 psi a to 350 psia, produces a l/b of greater than 1.0.
because each of Examples 11-13 were conducted at temperature of 95 °C, presumably according to Comparative Example 42, using equal ratios of H2 to CO (each at a partial pressure of 130 psi)3, where the l/b ratio is respectively 1.41, 1.94, and 2.72, which, per the second claim 1 ‘wherein clause’, is “greater than 1.0.”
T. Puckette et al., US 5,840,647 (1998) (“Puckette”)
Puckette teaches that fluorophosphite diester compounds of formula (I) are useful as ligands in catalyst systems for the conversion of olefins to aldehydes. Puckette at col. 1, lines 59-60; Id. at col. 3, lines 20-25. Puckette teaches working examples involving hydroformylation of olefins to aldehydes using ligand 2,2'-ethylidene bis(4,6-di-tert-butylphenyl) fluoro-phosphite (which is the same Ligand C (later to be commercially distributed as Ethanox 398™) of Liu discussed above).
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Puckette’s ligand C falls within the claimed ligand of Formula (I) for claims 1-6, 8, 9, 11-19, and 21. Puckette at col. 11, lines 40-55. With respect to the
The partial pressures of the ratio of the hydrogen to carbon monoxide in the feed is selected according to the linear : branched isomer ratio desired. Generally, the partial pressure of hydrogen and carbon monoxide in the reactor is maintained within the range of about 1.4 to 13.8 bars absolute (about 20 to 200 psia) for each gas. The partial pressure of carbon monoxide in the reactor is maintained within the range of about 1.4 to 13.8 bars absolute (about 20 to 200 psia) and is varied independently of the hydrogen partial pressure. The molar ratio of hydrogen to carbon monoxide can be varied widely within these partial pressure ranges for the hydrogen and carbon monoxide. The ratios of the hydrogen to carbon monoxide and the partial pressure of each in the synthesis gas (syngas-carbon monoxide and hydrogen) can be readily changed by the addition of either hydrogen or carbon monoxide to the syngas stream. We have found that with the fluorophosphite ligands described herein, the ratio of linear to branched products can be varied widely by changing the partial pressures of the carbon monoxide in the reactor.
Puckette at col. 9, lines 37-56 (emphasis added).
In working Example 1, Puckette teaches hydroformylation of propylene with the Ethanox 398™/rhodium catalyst complex, at a temperature of 115 °C, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate as solvent, reactor pressure (260 psig) and having the following partial pressures (psia) in the feed to the reactor: hydrogen = 96 psia; carbon monoxide = 96 psia; nitrogen= 29 psia; and propylene = 54 psia. Puckette at col. 11, lines 35-67. Puckette teaches that the reaction was carried out under the above flows for 5 hours and the butyraldehyde production rate for the last 3 hours of operation averaged 92.5 g/hour for a catalyst activity of 5.86 kilograms butyraldehyde/gram of rhodium-hour and the product N:Iso ratio was 3.3:1. Puckette at col. 12, lines 1-5.
In working Example 5, Puckette teaches hydroformylation of a mixture of cis- and trans-2-octene with the Ethanox 398™/rhodium catalyst complex, at a temperature of 110 °C, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate as solvent, reactor pressure (300-400 psig). Puckette at col. 13, lines 15-35. Puckette teaches that gas chromatography of the recovered liquid revealed that 71 mole percent of the octene had been converted to a mixture of nonyl aldehydes, where the nonyl aldehyde product had a normal to branched isomer ratio of 0.63:1. Puckette at col. 13, lines 33-37.
Obviousness Rationale
One of ordinary skill in the art to develop workable or optimum ranges for result-effective parameters. MPEP § 2144.05; see also, In re Boesch, 617 F.2d 272,276 (CCPA 1980); In re Aller, 220 F.2d 454, 456 (CCPA 1955). Generally, with respect to optimization of result-effective variables, changes to the prior art involving degree is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions. MPEP § 2144.05(II)(A) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955); In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929). Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. MPEP § 2144.05(I) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955)).
Claims 1-5 are obvious for the following reasons. One of ordinary skill is motivated to synthesize mixtures of isobutyraldehyde and n-butyraldehyde from propylene by hydroformylation using either of Ligand C or Ligand D complexed with rhodium as a catalyst, in view of Liu’s and Puckette’s teaching that the normal- and iso-butyraldehydes obtained from propylene are in turn converted into many commercially valuable chemical products. Liu at page 1, [0002].
One of ordinary skill is thus motivated to practice the following claim 1 limitations, as taught by either of Liu or Puckette:
Claim 1. A process for preparing linear and branched aldehydes, the process comprising: contacting an olefin with hydrogen (H2) and carbon monoxide (CO) in the presence of
a catalyst solution, the catalyst solution comprising:
a hydroformylation solvent;
a rhodium (Rh) source; and
a fluorophosphite ligand of formula (I) . . .
Regarding the following two claim 1, ‘wherein clauses’:
claim 1 . . . wherein the contacting of the olefin with the H2 and the CO in the presence of the catalyst solution at:
a temperature ranging from 95 °C to 130 °C,
a carbon monoxide partial pressure (PCO) ranging from 110 psia to 350 psia, and
a hydrogen partial pressure (PH2) ranging from 20 psia to 150 psia,
produces a ratio of linear aldehydes to branched aldehydes (l/b) of less than 1.0; and
wherein the contacting of the olefin with the H2 and the CO in the presence of the catalyst solution at:
a temperature ranging from 60 °C to 100 °C,
a PCO ranging from 5 psia to 150 psia, and
a PH2 ranging from 100 psi a to 350 psia, produces a l/b of greater than 1.0.
and similar clauses recited in dependent claim 2-5, the following applies. One of ordinary skill is motivated to practice the propylene hydroformylation, using either of Ligand C or Ligand D complexed with rhodium as a catalyst, by optimizing or developing workable ranges of temperature, PCO (CO concentration) and PH2 (hydrogen concentration) because both Liu and Puckette teach that these are optimizable, result-effective variables that control the l/b ratio. Liu teaches that the partial pressures of the ratio of the hydrogen to carbon monoxide in the feed can be selected according to the linear: branched isomer ratio desired. Liu at page 15, [0031]. Liu and Puckette both teach that with the disclosed fluorophosphite ligands, the ratio of linear to branched products can be varied widely by changing the partial pressures of the carbon monoxide in the reactor. Liu at page 15, [0031].
With respect to temperature, Liu teaches:
[0030] The reaction conditions for the process of the present invention can be conventional hydroformylation conditions. The process may be carried out at temperatures in the range of 20° to 200°C, in some embodiments the hydroformylation reaction temperatures are from 50° to 135°C. In some embodiments, reaction temperatures range from 75° to 125°C.
Liu at page 15, [0030].
With respect to ratios and pressures of H2 and CO, and their partial pressures, Liu teaches that:
[0031] The hydrogen : carbon monoxide mole ratio in the reactor likewise may vary considerably ranging from 10:1 to 1:10, and the sum of the absolute partial pressures of hydrogen and carbon monoxide may range from 0.3 to 36 bars absolute. The partial pressures of the ratio of the hydrogen to carbon monoxide in the feed can be selected according to the linear : branched isomer ratio desired. Generally, the partial pressure of hydrogen and carbon monoxide in the reactor can be maintained within the range of 1.4 to 13.8 bars absolute (20 to 200 psia) for each gas. The partial pressure of carbon monoxide in the reactor can be maintained within the range of 1.4 to 13.8 bars absolute (20 to 200 psia) and can be varied independently of the hydrogen partial pressure. The molar ratio of hydrogen to carbon monoxide can be varied widely within these partial pressure ranges for the hydrogen and carbon monoxide.
Liu at page 15, [0031]. Puckette provides similar teachings regarding Ligand C.
Liu’s disclosed temperature, H2 partial pressure (PH2) range; and CO partial pressure (PCO) range all overlap with the ranges of claims 1-5, except the claim 4 limitation of “a PCO ranging from 5 psia to 10 psia”, which is lower (but close to) Liu’s lower limit of “20 to 200 psia”. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP 2144.05 (I). Similarly, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. MPEP 2144.05 (I). Here the claim 1-5 temperature, H2 partial pressure (PH2) range; and CO partial pressure (PCO) ranges are obvious variations of Liu because Liu teaches that each of these is a result-effective, optimizable variable, where “[t]he partial pressures of the ratio of the hydrogen to carbon monoxide in the feed can be selected according to the linear : branched isomer ratio desired”.
Claim 6 and 8 are obvious because the above § 103 rationale proposes propylene as the olefin.
Claims 9 and 11 are obvious subject to the § 112(b) rejection above. Liu teaches that:
The ratio of gram moles fluorophosphite ligand to gram atoms transition metal can vary over a wide range, e.g., gram mole fluorophosphite:gram atom transition metal ratio of 1 :1 to 400:1. For rhodium-containing catalyst systems, the gram mole fluorophosphite:gram atom rhodium ratio in some embodiments is in the range of 1: 1 to 200: 1 with ratios in the range of 1: 1 to 120: 1.
This a similar range to that taught in the instant specification. Specification at page 18, [0092]. However, per the § 112(b) rejection, claim 9 recites the inverse range.
Claim 12 is obvious because Liu teaches that the solvent may be toluene. Liu at pages 13-14, [0027].
The structural limitations of claims 13-20 and 22 are met by Liu Ligand D.
The structural limitations of claim 13-19 and 21 are met by Liu Ligand C.
Conclusion
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ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 Liu has a typographical error in depicting the structure of fluorophosphite Ligand C (Ethanox 398™) in that it is missing two oxygen atoms. Liu at page 19, [0043] (depicting an incorrect structure of Ethanox 398™/Ligand C). The correct/intended structure is drawn by the Examiner above. This typographical error is clearly evident to one of ordinary skill in view of Liu’s cited reference: Puckette, Halophosphite Ligands for the Rhodium Catalyzed Low-Pressure Hydroformylation Reaction, in Catalysis of Organic Reactions, 31-38 (S. Schmidt ed., 2006) (depicting the correct structure of Ethanox 398™); see also, WO 2017/044277 (2017) at page 8.
2 Liu neglects to state the procedure employed for Examples 11-13 (Ligand D). Liu at page 25, lines 1-4. One of ordinary skill would presume that Examples 11-13 were also carried out in the same manner as Comparative Example 4.
3 Comparative Example 4 teaches that the reactor pressure control was set at 17.9 bar (260 psig). Using H2/CO at 260 psi in a 1:1 ratio, the partial pressure of each gas is calculated by the Examiner to be 130 psi (Pgas = mole fraction [Symbol font/0xB4] psi).
Prosecution Insights