DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Status
No claims are amended or cancelled.
Claims 1-20 continue to pend for examination below.
Response to Arguments
Applicant's arguments filed 16 December 2025 have been fully considered but they are not persuasive.
Applicant argues on page 7 of the Remarks that the function of the solvents in Dunlop and the solvents in Pierotti are different, and thus one of ordinary skill in the art cannot apply the motivation of Pierotti of efficient and extractive distillation as motivation to use the solvents of Pierotti, because one of ordinary skill in the art cannot know whether the solvent in Pierotti is useful as the solvent of Dunlop.
In response, the Examiner respectfully disagrees. Dunlop generally teaches ketones and alcohols are useful as the solvent for dissolving the cuprous salt (column 4, lines 2-5). Pierotti teaches monoketones as a mutual solvent (column 4, lines 50-51) and amino-alcohols as a selective solvent (column 4, lines 8-9) in the solvent mixture. Thus, one of ordinary skill in the art would reasonably expect that both the ketone and alcohol portions of the solvent mixture of Pierotti would function as the ketone or alcohol solvent in Dunlop. Pierotti also further teaches that the combination of amino-alcohol and mono-ketone allows the extractive distillation of unsaturated compounds to be economic and efficient (column 1, lines 29-30). As both Dunlop and Pierotti teach that the composition is used for extractive distillation of unsaturated compounds, one of ordinary skill in the art would continue to expect that the motivation of Pierotti would apply to the combination of Pierotti and Dunlop, as argued in the Rejection.
Applicant argues in the first full paragraph of page 8 of the Remarks that Dunlop does not disclose or teach a general range of a ratio of solvent to copper salt, instead only teaching example ratios using different solvents which are not ketones, one of ordinary skill in the art would understand that weight ratios in a composition depends on the types of the species, and thus the Examiner’s calculation of a range of solvent to copper salt is improper.
In response, the Examiner agrees that the solvents in the Examples of Dunlop are not ketones or amino-alcohols. However, the Examiner disagrees with the Applicant’s conclusion. The Table shows that Dunlop tested a variety of weight ratios for each solvent (see column 5). Thus, the weight ratio of solvent to copper salt is not clearly tied to the type of solvent, but instead is a parameter that Dunlop varied across the examples. Thus, the Examiner continues to use the range of weight ratios in the Table of Dunlop as a reasonable expectation for the weight ratios of the copper salt to the solvents of Pierotti, absent any evidence that the weight ratios in the Table are not suitable.
Applicant also argues in the middle of page 8 of the Remarks that Pierotti does not disclose the lower limit of 0.01:1 mentioned in the rejection, merely stating that the ratio not greater than 1:1 by volume, thus the Examiner’s calculation using a lower bound of 0.01:1 is incorrect
In response, the Examiner did not clearly state the explanation of the selection of the lower bound, and agrees that the calculation using the lower bound is incorrect. However, even using only the upper bound of 1:1 by volume recited in column 6, lines 3-4 of Pierotti, the calculated ranges continue to overlap the claimed ranges (see new calculation in the Rejection below), and thus the obviousness of the ranges is properly maintained.
Applicant further argues on page 8 of the Remarks that using the ratio of Pierotti to convert the total solvent of Dunlop is not reasonable, because Dunlop only teaches ketones dissolving the cuprous salt, and thus the amino-alcohol of Pierotti would not be expected to function as a solvent in Dunlop.
In response, the Examiner respectfully disagrees. Dunlop teaches ketones and alcohols as options (column 4, lines 4-5). Pierotti teaches a mixture of ketone and amino-alcohol, which has the alcohol functional group. Thus, both solvents of Pierotti are expected to function as the solvent of Dunlop, thus the Examiner’s calculation is proper.
Applicant continues to argue on pages 8-9 of the Remarks that Dunlop only teaches the use of both ketones and alcohols together as a united solvent, thus the mixture once adding Pierotti would contain further alcohol solvent that is not accounted for in Examiner’s calculation.
In response, the Examiner respectfully disagrees. As explained above, the amino-alcohol of Pierotti has alcohol functionality and would be expected to function as an alcohol solvent, as taught by Dunlop. Alternatively, the Examiner also disagrees with the Applicant’s interpretation of Dunlop. The section of Dunlop reciting the solvents states “many other polar organic solvents lend themselves equally well…among those being isobutyronitrile, acetonitrile, the xylenes…ketones and alcohols, tertiary butyl toluene…and sulfides. Mixed solvents such as…propionitrile and methyl ethyl ketone; propionitrile and isopropyl alcohol…are useful as solvents.” (column 4, lines 1-10). Thus, Dunlop clearly contemplates alcohols or ketones as an option for the solvent, as the listed mixtures only include one or the other. Thus, one of ordinary skill in the art would conclude that ketones or alcohols could be used in the alternative, not requiring both.
Applicant argues on page 9 of the Remarks that Pierotti does not disclose the number of carbon atoms in the ketones, only disclosing the range of about 3 to 8 carbon atoms for the ethers, citing column 4, lines 50-54, and also notes that an example ketone of Pierotti is diisobutyl ketone which has 9 carbon atoms.
In response, the Examiner respectfully disagrees. The phrasing of Pierotti is “mono ketones, alcohols, and ethers containing from about 3 to 8 carbon atoms”. One of ordinary skill in the art would reasonably interpret this phrasing as saying each of the mono ketones, alcohols, and ethers have about 3 to 8 carbon atoms. As such, it remains obvious to select a ketone having 7-10 carbon atoms from the list of monoketones having 3 to 8 carbon atoms explicitly recited by Pierotti.
Applicant additionally argues in the middle of page 9 of the Remarks that the claimed process provides synergistic results which are unexpected, based on the Examples and Comparative Examples in the instant specification.
In response, the Examiner respectfully disagrees that the Examples provide evidence of unexpected results, because the Examples are not commensurate in scope with the claims. The claims recite a mixture of “alcohol-amine, saturated monoketone of 7-10 carbon atoms, and monovalent salt of Group IB metal”. These are broad categories, whereas the Examples in the instant specification (paragraph [0064]) only use a single example mixture comprising a single compound (ethanol-amine, 2-heptanone, and cuprous chloride) selected from each category. There is no evidence that any results for the exemplified mixture necessarily hold across every possible mixture of compounds formed by the broad categories of instant claim 1, and thus there is no evidence of unexpected results.
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.
Claims 1-5, 7, 10, and 12-17 are rejected under 35 U.S.C. 103 as being unpatentable over Dunlop et al. (US 3,401,112) in view of Pierotti (US 2,455,803).
With regard to claims 1, 2, and 4, the phrase “alpha-olefin extractant” is an intended use of the claimed composition, which does not result in a structural difference to the composition and, thus, does not add patentable weight to the composition claim. See MPEP 2111.02(II).
Dunlop teaches a composition for separating unsaturated hydrocarbons from saturated hydrocarbons (column 1, lines 13-15) comprising cuprous trifluoroacetate (salt of Group IB metal instant claims 1 and 4) (column 3, lines 48-49) in the presence of a solvent for extractive distillation including ketones and alcohols (column 3, lines 66-68 and column 4, lines 2-5).
Dunlop does not specifically teach a combination of an alcohol-amine and a saturated monoketone having a carbon chain length of 7-10 as the solvent for the extractive distillation.
Pierotti teaches a solvent mixture for extractive distillation of mixtures having differing degrees of unsaturation (column 3, lines 3-5) comprising a selective solvent and mutual solvent (column 1, lines 2-5). Pierotti further teaches the selective solvent can include mono, di, and tri ethanol amines (alcohol-amine instant claims 1 and 2) (column 4, lines 8-9) and the mutual solvent can include saturated mono-ketones having a carbon chain length of 3 to 8 (column 4, lines 50-51), which overlaps the range of 7-10 of instant claim 1, rendering the range prima facie obvious. Pierotti further teaches the mixture of solvents allows the extractive distillation to be economic and efficient (column 1, lines 29-30).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use the solvent mixture of Pierotti in the composition of Dunlop, because Dunlop and Pierotti each teach a composition for separating saturated and unsaturated compounds, Dunlop teaches suitable solvents include ketones and alcohols, and Pierotti teaches that the specific mixture of monoketone and alcohol amine provides the benefits of economic and efficient extractive distillation (column 1, lines 29-30).
Pierotti further teaches the ratio of mutual solvent (monoketone) to selective solvent (alcohol-amine) is up 1:1 by volume (column 6, lines 3-4), which using the density of the solvents 2-heptanone or 2-octanone for the ketone (mutual solvent) and monoethanol amine, diethanol amine, or triethanol amine for the amino-alcohol (selective solvent) is equivalent to a ratio of up to 0.8:1 by weight (see calculation details below). Dunlop teaches the weight ratio of solvent to copper salt in the Examples ranges from 0.75:1 to 5.25:1 (column 5, Table).
Given that the weight ratio of ketone to amine-alcohol is up to 0.8:1 and the ratio of total solvent to salt is 0.75-5.25, the ratio of ketone to salt is up to 2.31:1, and the ratio of amine-alcohol to salt is at least 0.42:1 (see calculations below). If the amount of salt in the weight ratio of claim 1 is set to 1, the ratio in claim 1 is transformed to be (1.5-20):(1.33-15):1 (see calculation below). The ranges of the amount of alcohol-amine of at least 0.44 and the amount of monoketone of up to 2.31 overlap the transformed ranges of 1.5-20 and 1.33-15 of instant claim 1, respectively, rendering the ratios prima facie obvious.
Calculations
Density of 1-heptanone = 0.82 g/mol
Density of 2-heptanone = 0.82 g/mol
Density of monoethanol amine = 1.02 g/mol
Density of diethanol amine = 1.1 g/mol
Density of triethanol amine = 1.13 g/mol
Given a volume ratio of up to 1:1 ketone to alcohol-amine, the weight ratio is up to
0.82
1.02
=
0.8
:
1
,
0.82
1.1
=
0.75
:
1
, or
0.82
1.13
=
0.73
:
1
for each alcohol amine, respectively.
Given the weight ratio of up to 0.8:1 and the total solvent to salt ratio of 0.75-5.25, the ratio of ketone to salt is calculated using the following:
m
a
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m
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m
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+
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=
0.8
1.8
=
0.44
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a
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s
o
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v
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n
t
=
5.25
x
0.44
=
2.31
. Thus, the ratio of ketone to salt is up to 2.31:1
m
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n
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m
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m
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a
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+
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=
1
1.8
=
0.56
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a
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s
o
l
v
e
n
t
=
0.75
x
0.56
=
0.42
. Thus, the ratio of amine to salt is at least 0.44:1
To set the salt in the ratio of claim 1 equal to 1, everything in the ratio is divided by (0.1-0.6)
0.9
-
2
0.1
-
0.6
=
1.5
-
20
0.8
-
1.5
0.1
-
0.6
=
1.33
-
15
With regard to claim 3, Pierotti does not specifically teach the monoketone having a chain length of 7 or 8 is 2-heptanone or sec-octanone. However, one of ordinary skill in the art would understand there are a finite number of monoketones having 7 or 8 carbon chains, including the listed options, and would be motivated to select 2-heptanone or sec-octanone from the finite list without undue experimentation and with a reasonable expectation of success because Pierotti teaches the general category of monoketones (column 4, lines 50-51).
With regard to claim 5, Dunlop in view of Pierotti teaches the composition above. Dunlop further teaches a method for separation of hydrocarbons comprising:
passing the mixture of hydrocarbons to an extractive distillation tower 12 and contacting with the copper salt solution (extractant of claim 1) to produce an overhead stream (raffinate) 14 and a solvent stream comprising the unsaturated compounds 17;
passing the stream 17 to a solvent stripper 24 to recover the desired unsaturated compound overhead and the solvent mixture (extractant) 13 at the bottom (Figure and column 4, lines 43-65).
Dunlop further teaches the mixture can be used to recover monoolefins by separation of monoolefins from paraffins (column 1, lines 23-24) and Pierotti also teaches separating olefins from paraffins (column 2, lines 46-47). Dunlop and Pierotti do not specifically recite alpha olefins as the olefins. However, one of ordinary skill in the art would find it obvious to use the process of Dunlop with the composition of Dunlop in view of Pierotti to separate alphaolefins from alkanes, as claimed, because alphaolefins are a specific olefin which are known to be a valuable product, and Dunlop generally teaches monoolefins separation from paraffins.
With regard to claim 7, Dunlop teaches the extractive distillation tower (column) 12 and the solvent stripper (refining column) 24 (column 4, lines 44 and 50).
Dunlop is silent regarding conditions outside of a single example which is outside the scope of the claimed invention.
Pierotti teaches the temperature and pressure of the extractive distillation column is -50 to 350°C and the pressure is 0.1 to 500 psi (0.69 to 3447.68) (column 5, lines 68-71). These overlap the ranges of 45-56 kPa and 45-125°C of instant claim 7, rendering the ranges prima face obvious. Pierotti further teaches the temperature should be above the bubble temperature of the mixture and below the boiling temperature of the solvents under the pressure and temperature conditions maintained in the extractor and that the pressure can be adjusted to keep the mixture thermally stable (column 5, lines 40 and 60-65).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to select a temperature and pressure within the range of Pierotti that overlaps the claimed ranges of 45-56 kPa and 45-125°C for the column of Dunlop, because Pierotti teaches wide ranges which encompass the claimed ranges and further teaches that one of ordinary skill in the art is capable of selecting the desired temperature and pressure based on the solvent system used (column 5, lines 60-65).
With regard to claim 10, Dunlop teaches heating the feed mixture to a vapor or just below the boiling point (column 4, lines 25-27) and introducing the solvent mixture after preheating (column 4, lines 31-33). While Dunlop does not explicitly teach heading the feed (raw material) to 65-100°C and the solvent mixture (extractant) to 55-85°C, one of ordinary skill in the art would understand that suitable temperatures for the preheating are based on the specific composition of the feed (raw material) and solvent mixture (extractant), as different components would have different boiling points. Thus, the temperatures of the preheating are result-effective variables, and can be optimized.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to preheat the feed to 65-100°C and the solvent mixture to 55-85°C, as claimed, since it has been held that discovering an optimum value of a result effective variable involves only routine skill in the art. See MPEP 2144.05(II).
With regard to claims 12, 14, and 16, Pierotti teaches the temperature of the extractive distillation column is -50 to 350°C (column 5, lines 68-69). This overlaps the ranges of 45-65°C, 75-95°C, and 95-125°C of instant claims 12, 14, and 16, respectively.
With regard to claims 13, 15, and 17, Dunlop in view of Pierotti does not specifically teach the bottom temperature of the extractive distillation and stripping (refining) columns. However, the bottom temperature of the column is understood in the art to be adjusted based on the composition of the mixture to be separated, the solvent composition, and the temperature of the overall column, in order to get the desired separation. Thus, the bottom temperature of each column is a result-effective variable, and can be optimized.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to adjust the bottom temperature of the extractive distillation column to 55-59°C, 84-88°C, or 110-114°C and the bottom temperature to 58-62°C, 87-91°C, or 113-117°C, as claimed in instant claims 13, 15, and 17, since it has been held that discovering an optimum value of a result effective variable involves only routine skill in the art. See MPEP 2144.05(II)
Claims 6 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Dunlop et al. (US 3,401,112) in view of Pierotti (US 2,455,803) as applied to claim 5 above, and further in view of Boudreau et al. (US 2003/0125599) and Quann et al. (US 4,686,317).
With regard to claim 6, Dunlop in view of Pierotti teaches the method above, where the mixture to be separated is an olefin and paraffin mixture.
Dunlop in view of Pierotti does not specifically teach the mixture can be a Fischer-Tropsch synthetic oil.
Boudreau teaches separation of mono-olefins and diolefins from paraffins with a copper salt in a solvent (paragraph [0022]). Boudreau further teaches the oils produced in a Fischer-Tropsch process have a large amount of alpha-olefins which should be separated, and that the alpha-olefins can be separated by extractive distillation with the copper salt solution in an inexpensive manner (paragraphs [0026] and [0030]).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to use a Fischer-Tropsch oil as the source of the hydrocarbons in Dunlop in view of Pierotti because Dunlop in view of Pierotti teaches separation of olefins from alkanes, and Boudreau teaches it is desirable to separate alphaolefins from a Fischer-Tropsch mixture by contact with a solvent of copper salt, and teaches that extraction is inexpensive (paragraph [0030]).
Dunlop in view of Pierotti and Boudreau does not specifically teach deacidification and deoxygenation of the Fischer-Tropsch mixture.
Quann teaches a process for removing oxygenated hydrocarbons from hydrocarbon streams (Abstract) where the oxygenated compounds include acids (column 19, claim 1) and the hydrocarbon stream is preferably a Fischer-Tropsch product (column 1, lines 11-13). Quann further teaches that the olefinic feedstocks are useful for further processing (column 2, lines 9-15).
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to deacidify and deoxygenate the Fischer-Tropsch product before separating the desired alphaolefins, because Dunlop in view of Pierotti and Boudreau teaches separation of alphaolefins from Fischer-Tropsch products and Quann teaches removing oxygenates from Fischer-Tropsch products before further uses (column 2, lines 9-15).
With regard to claim 11, Boudreau teaches that the Fischer-Tropsch oil comprises about 75 wt% alpha olefins (paragraph [0030]), which is within the range of 70-75 parts of instant claim 11. Thus, the remaining products can include up to 25 wt% alkanes, which overlaps the range of 20-25 parts, rendering the range prima facie obvious.
Claims 8, 9, and 18-20 are rejected under 35 U.S.C. 103 as being unpatentable over Dunlop et al. (US 3,401,112) in view of Pierotti (US 2,455,803) as applied to claim 7 above, and further in view of Zubir et al. (Systematic design of energy efficient extractive distillation column for azeotrope mixture).
With regard to claims 8, 9, and 18, Dunlop teaches the mass ratio of extractant to feed ranges from 1.3 to 14 (column 6, Table), which overlaps the range of 2.5-3.5 of instant claim 8 and the amount of 3 of instant claim 18, rendering the range and amount prima facie obvious.
Dunlop does not teach the number of plates, feeding position of feed or extractant, or reflux ratio of the extractive rectification column or the number of plates, feeding position, or reflux ratio in the stripping (rectifying) column.
Zubir teaches a process for designing extractive distillation columns (Abstract). Zubir further teaches that design variables such as reflux ratio, feeding position, and minimum number of stages (plates) can be determined by a driving force diagram which can be plotted using known data for the components of the solvent mixture (Section 2, paragraph bridging pages 2637-2638). Therefore, Zubir teaches that the reflux ratio, feeding positions and number of plates are all result-effective variables, and can be optimized.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to adjust the extractive distillation column to have a plate number to 34-36 or 35, the raw material feeding position to plates 24-26 or 25, the extractant feeding position to plates 3-5 or 4, and the reflux ratio to 3.3:1 to 3.7:1 or 3.5:1 (instant claims 8 and 18); and the rectifying column to have a plate number of 39-41, a feeding position at 27-29, and a reflux ratio from 2.5 to 3.5 (instant claim 9), as claimed, since it has been held that discovering an optimum value of a result effective variable involves only routine skill in the art. See MPEP 2144.05(II)
With regard to claims 19 and 20, Dunlop teaches heating the feed mixture to a vapor or just below the boiling point (column 4, lines 25-27) and introducing the solvent mixture after preheating (column 4, lines 31-33). While Dunlop does not explicitly teach heading the feed (raw material) to 68-72°C and the solvent mixture (extractant) to 58-62°C as in instant claim 19, or the raw material to 93-97°C and extractant to 78-82°C as in instant claim 20, one of ordinary skill in the art would understand that suitable temperatures for the preheating are based on the specific composition of the feed (raw material) and solvent mixture (extractant), as different components would have different boiling points. Thus, the temperatures of the preheating are result-effective variables, and can be optimized.
Therefore, it would have been obvious to one of ordinary skill in the art at the time of the invention to preheat the feed to 68-72°C or 93-97°C and the solvent mixture (extractant) to 58-62°C or 78-82°C, as claimed, since it has been held that discovering an optimum value of a result effective variable involves only routine skill in the art. See MPEP 2144.05(II).
Conclusion
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 ALYSSA L CEPLUCH whose telephone number is (571)270-5752. The examiner can normally be reached M-F, 8:30 am-5 pm, EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, In Suk Bullock can be reached at 571-272-5954. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Alyssa L Cepluch/Examiner, Art Unit 1772
/IN SUK C BULLOCK/Supervisory Patent Examiner, Art Unit 1772
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